The Substack Podcast

We spoke with Kevin Muir of The MacroTourist, a newsletter about trading and investing that aims to make finance fun.

Formerly a proprietary trader, Kevin quit his job at a bank in the early 2000s to start working for himself, and he still trades his own capital to this day. Kevin started keeping a journal about trading, but so many people asked for his opinions that he decided to share his writing publicly. Today, he shares his passion for the markets with a loyal following of paid readers, who love his almost-daily updates on his trading portfolio and breezy, irreverent writing style.

We talked to Kevin about his motivation to write about markets, how he differentiates his content from others in the finance blogging world, and how he transitioned to a 100% paid newsletter.

Links

The MacroTourist, Kevin’s newsletter

Kevin on Twitter

The Reformed Broker on CNBC, a finance blogger who uses Twitter effectively

Highlights

(04:26) The world of finance blogging

(06:06) How Kevin uses Twitter as a tool for blogging

(08:23) The start of Kevin’s writing journey and how he grew his readership

(15:19) Why Kevin’s writing style is distinct in the world of finance blogs

(26:13) How Kevin came to Substack after experimenting with other writing platforms, including WordPress, Squarespace, and Mailchimp

(35:02) Why Kevin decided to switch to 100% paid subscriptions

(42:27) How paid subscriptions allowed Kevin to learn more from his readers

On getting started:

The one piece of advice I'd give is, just keep producing content, and it's going to go slow at first. But then the power, as I say, the power of compounding will cause it to accelerate.

On keeping a writing schedule:

I always tell them [new writers] to write and write on a regular basis, because one of the things that a lot of people do is, they go and they start writing and then they fall off. They don't bother with the discipline of it. A lot of times people are desperate for content, but what they don't want is for you to go away for two months and then you're back for two episodes and then you're gone. So I always told people to make your schedule and stick to it.

On giving and receiving from readers:

I realized that as people started reading it [my newsletter], it ended up being something I could give, so that I could receive back some information. And that's how it really kind of morphed for the longest time, I said, “I'm just going to write this thing, put it out there, and then I'm going to receive back as much as or all the effort that I'm putting into it.” I felt like it was coming back at me, in more than enough, to pay for itself that way.

Transcript

Nadia (00:27):

You write The MacroTourist, which you described as an almost daily email about markets. From my poking around, it kind of looks like finance with a bunch of memes involved, and very breezy, irreverent style that definitely caught my eye. And it seems like that breezy fun style has also sort of dictated your career path. From what I can tell, you've kind of had a very interesting path of getting here from trading for other people, trading for yourself, and now also writing about trading. So yeah, just diving right into, what is your day job right now? How did you end up here?

Kevin (01:02):

Okay, well, in the nineties, I actually was an equity derivative trader at a Canadian large bank. And so, what they do is, we sit around and we make markets for institutions like pension funds, and we trade blocks of stocks. And in my case, I actually traded ETFs like index derivatives and other fancy stuff like that. And I was very fortunate because I got that job in the nineties when I was actually...I hadn't yet finished university. And I got the job because, as my boss told me at the time, there was guys better at computers and there was guys better at trading, but I was the right mix of both.

Kevin (01:46):

And back then there was very little computerized trading. And what I was...I had that ability to kind of bridge the gap. And so, I was hired to handle all the index clients and it was a very entrepreneurial firm. And before I knew it, they had gone from me just covering clients, to me trading for the bank, meaning taking positions, until finally I was the basically head risk-taker for the equity derivatives for most of the late nineties, during the dot-com bubble. Then what happened was our daughter was born and she was born with a heart defect that was fixed at birth.

Kevin (02:25):

It was one of these things, the wonderful doctors came in and they operated laparoscopically and fixed her problem. But it was one of these moments in life where you kind of sit back and wonder what's important in life. And I decided that there was more than just trading and I wasn't having as much fun because the bank was becoming increasingly like a bank, and less entrepreneurial. So before the market crashed in 2000, I hung up my skates, and I kind of semi quit/retired. So I came home and I thought to myself, "I can go work for a hedge fund or do something like that, but I can also go try trading for myself. And if it doesn't work a year from now, I could go back and work for a bank or a hedge fund and nobody will remember that year."

Kevin (03:14):

Well, one year turned into two. And then turned into five. And next thing I know I've gone 15 years, just trading for myself with another guy. And during those periods, it was kind of lonely at times. So I started writing a blog, or it was actually more of a journal when I first started, because one of the things they encourage traders to do is write down your thoughts. And people would phone me up and say, "What do you think of the market?" And I would just say, "You know what? Here, I'll send you off what I wrote to myself." And that's how the MacroTourist was born. And for the longest time it was just a free thing I like to... because I don't work for a bank anymore. And because most research is often boring and not very kind of fun to read, I do like to make it a little more fun. So at the very least, I always say to people, "I hope to make you smile."

Nadia (04:06):

I definitely, going through some of your posts, I was giggling to myself... and I don't even understand finance, so it was great. Your goal has been achieved. What is the world of finance blogging? I don't even really necessarily know, is that the right term that you'd use? There are other people that write like you, but what you're doing is so different.

Kevin (04:26):

For sure. There are a lot of blogs out there. And one of the things that a lot of people as well do in finance, is that we're big Twitter users, and it ends up being that Twitter is the perfect vehicle for traders and investors, because what you want is basically real time information flowing back and forth. So there's many people that will be on Twitter posting kind of long form, string together 20 tweets that they kind of give their views, and they include charts. And then there's some that go off and actually go and create full-on blogs. There's a very famous guy called The Reformed Broker that's on CNBC, and he originally started as just a broker that wrote a blog, until he parlayed into a million plus Twitter followers, and a job on CNBC.

Kevin (05:16):

So it's definitely something that's out there. One of the problems that occurs is that anybody who works for a large firm is often hindered by compliance. Compliance basically means legal sign off, because if you're registered as an investment advisor, it's difficult for you to write. So there's a whole slew of guys and women very similar to me, in that they don't work for anyone but themselves, and are posting information out there like my blog. Although I would say that my style's a little unique, the fact that I'm writing a finance blog is by no means unique.

Nadia (05:57):

Did you.... because it seems like you're somewhat active on Twitter as well, did Twitter come before blogging? Did blogging help with Twitter?

Kevin (06:06):

No, so I hated Twitter. When I first turned on Twitter, it felt like a fire hose coming at me and I didn't really understand how to use it. And then for the longest time I would write my blog, and I would just put a link to it on Twitter just because I felt like I had to. And then I noticed that some guys would be taking my blog, and taking a couple of charts from there and putting a little sentence or two on it. And they would be getting all these retweets and all this information. And I realized that it was kind of a tool that I could use to promote myself a little bit. And it is frustrating, Twitter is, it's a great tool and then it's also a great kind of almost drug, that you have to be careful of, because you can find yourself getting sucked into a lot of holes that waste a lot of time for no productive use.

Kevin (06:57):

So, the way I use Twitter is, originally, it was just a way to get my brand out there. It's still that way. I do say that having a large Twitter following is actually beneficial to traders, because when I need some information or interested in a point of view, I might just throw it out there and say, "Hey, does anyone have this report?" Or, "Does anyone know what's going on with this stock?" And it's really quite helpful that way, Twitter.

Nadia (07:30):

Do you find that the people you're talking to on Twitter are similar to the people that are also following your blog, or is it different sort of?

Kevin (07:35):

So I have a lot more people that will follow me on Twitter than the blog. So I do find that they are often different, but there is also some huge overlap, but Twitter ends up being a little more fast moving information, where the people that are reading my blog are probably not the type that are interested about every tick and staring at Twitter all day. So, there's kind of more traders that are glued to screens, I would say on Twitter, and then on the blog it would be more, there's still some traders reading it that way, but there's a lot more kind of serious, longer term investors.

Nadia (08:16):

If you started writing before you're using Twitter, how did you get anyone to read in the first place? How did you end up growing your audience?

Kevin (08:23):

Well, so when I first started writing, I just... as I said, I wrote it for myself, and I just ended up putting it out there because a couple of guys asked for it. And then I said... they kept phoning me back and saying, "Can you send me what you wrote today?" And I said, "You know what? I'll just put it on the internet." And although I had always kind of in the back of my mind said, "It'd be great, if I could do this kind of, and actually people would read it." It was never originally something that I set out to do.

Kevin (08:57):

And there hit a point where after doing it, I realized that it was actually, people were reading it and it was just getting passed around kind of by word of mouth, that I kind of understood that it was not only could it eventually be something like what it's turned into, a letter that people pay for, but it was also a great tool in the meantime to network and to learn about markets, and to be able to talk to different people.

Kevin (09:23):

So I really used it as a communication tool, because one of the problems was, when I used to work at a big bank, people would give you a fair amount of kind of just, I don't know, respect is the right word, but at least you had a certain sort of authority because you worked at a bank. When all of a sudden it's just a couple of guys sitting around an office banging around SMPs, it doesn't actually air itself to somebody that, if you wanted to talk to an economist at a bank that anyone would bother talking to you. So, I realized that as it kind of, people started reading it, it ended up being something I could give, so that I could receive back some information.

Kevin (10:03):

And that's how it really kind of morphed for the longest time, I said, "I'm just going to write this thing, put it out there, and then I'm going to receive back as much as all the effort that I'm putting into it." I felt like it was coming back at me, in more than enough, to pay for itself that way. And so in terms of, how did I do it? It's just slowly. I still remember going from 100 to 200 Twitters and I remember it crossing in a thousand. And I'm sure for... I don't have that many really, when you look at people with a hundred thousand or a million. But it’s just kind of one of those things that the power of compounding just ends up working.

Kevin (10:44):

And one of the advice I always give people when they say, "How did you go about doing it?" I always tell them to write and write on a regular basis, because one of the things that a lot of people do is, they go and they start writing and then they fall off. They don't bother with the kind of discipline of it. And so people want to... a lot of times people are desperate for content, but what they don't want is for you to go away for two months and then you're back for two episodes, or three episodes and then you're gone. So I always told people to make your schedule and stick to it.

Kevin (11:17):

And in fact, when I first started, I forced myself, at a certain point when I realized it was real, something that I wanted to develop, I forced myself to write every day, no matter if I didn't have anything to write about, I just figure out something to write about. And I remember reading Jonathan Coulton, he’s this kind of independent music guy, and he did an experiment where he forced himself to write, I can't remember, it was like 52 songs in 52 weeks. And he just... he would put it out there for free, and it was something. And I kind of took inspiration from that, because nothing like a deadline of having to write something and publish that day, to force you to come up with some ideas. And not only that, it ends up making you a better writer.

Nadia (11:59):

So true. I find myself often telling other writers also, consistency is the most important thing and it sounds really boring, because it just means you have to get into it for a while until someone notices. But it's when people start following you, they want to know that they're going to keep getting something. And personally, I only commit to a monthly newsletter because I can't bring myself to write every day. They really admire that. I think it's like, I imagine if you're writing everyday kind of takes the pressure off too, because you're like, "Well, if this one's okay, then maybe the next one's better or something like that."

Kevin (12:29):

Well that's true. You're absolutely correct, that if you do, you're going to have some doubts and then you're going to have some great ones. And the other thing that I've found over the years is, I can't even predict my good ones. Like the ones that seem to resonate with people. There's ones that I have spent ages on, worked hard on, thought, "This is the greatest thing I ever write." And then I send it out there and it's crickets. And then there's something else that I just kind of have a whim and I just polish off something, and it's all of a sudden, everyone's going like, "Oh, that's so amazing. It's so like a different way to think about it." So, it's difficult and I completely agree with you. Just the discipline of doing it, whatever your timeframe is, whether it's a monthly, weekly, daily, just do it and do it consistently.

Nadia (13:09):

Do you ever feel like... I guess, who is agreeing to get an email every single day for me in their inbox?

Kevin (13:17):

I don't know. Well, maybe it's different, in finance we get inundated with tons and tons of research emails. So, it's actually not that unusual to have somebody write every day. And in fact, there are guys that are right on, even way more than every day. So, it's really... like when we go look, if you were what's called a buy-side trader, meaning a client that's getting serviced by all the big brokers, your email, you might get 500 emails in a day. So, one of the things that I was always amazed about, is that when I would go look at people that would take the time to read it, I was always thankful and very appreciative, because I understood how much competition there was out there, and how many other people were reading it. So, that's one of the things that I never want to take for granted, because there’s so many different people out there that offer such great products, great services and stuff like that. So you should always be appreciative of the people that spend the time to read your stuff.

Nadia (14:25):

It kind of takes me back to just thinking again about your writing style and again, not having read a lot of other finance things, but it definitely stands out and it's definitely memorable, because it is just so fun and light and easy to read. And you were saying that, when you went sort of more independent, you had room for yourself, it was another way to help build credibility, which I think is so true. Like when you don't have a company, brand or something behind you, then it's sort of, well my writing and my voice is sort of like your portfolio and builds your credibility, is a culture of people that are into your stuff, I guess I'm sort of surprised that on the one hand it's sort of building your credibility. On the other hand you have this incredibly irreverent style. And so, is it just that people enjoy reading that sort of humor? Do you think like... are you operating in a more buttoned-up kind of world? Is it a corner of finance that's a little bit less buttoned-up?

Kevin (15:19):

So, I would say that most finance is less buttoned up than it seems. And especially on the trading side, in fact you would almost argue that there are a bunch of bores, and this is more how you would talk, like how you would speak to each other at bars and how when your traders are speaking. And so one of the things that I guess my writing is also more real. It's almost like the difference between seeing an essay that you hand your professor versus a note you send to your friend. And that's kind of how I would say... and one of the things I will say, is that I've noticed a change in style. So when I first came up with, I put a picture with a meme on the front of each and every one of my posts.

Kevin (16:11):

And I took that idea from another guy's blog in Canada, that wrote kind of a real estate blog, but he didn't put any kind of... he didn't tie it into his article and he didn't put any writing over it. He just took a funny picture and put it at the beginning. And I thought, "Well, that's a great idea, but really you should tie it in and try to figure out a way to make it kind of feed into the article." And when I first did it, it was something that very few people in finance, I don't think I'd ever seen apart from this one guy's real estate blog, I'd never seen anyone do it.

Kevin (16:41):

And I've noticed that there's more and more people doing it, and to the point where you're even seeing banks and they're kind of the last to do it, they're doing kind of more funny things. So like that, I definitely kind of sense a different tone in terms of, people have become less buttoned-up and there's less formal writing style. And the whole world is going more casual, and finance was probably one of the ones to be last to do that. But I do definitely notice that there's been a trend in that direction.

Nadia (17:14):

Has anyone ever been surprised when they meet you in real life versus you in writing stuff?

Kevin (17:20):

Well, so my wife always tells me, she says like, "You don't swear in real life. Why do you swear in your thing?" And then she always says, "It's almost like you're trying to be cooler on the writing than you actually are." So she definitely kind of laughs at me about that way. And I don't know, other people read it and they say, "Oh no, that's just like Kevin." So I don't know, maybe I portray something different to my wife than to the guys on the trading desk. But I do think that it's... I think people find it refreshing, because it's definitely more honest and more real than most writing that they're getting.

Nadia (17:59):

I can definitely see it also just being the kind of thing that people want to share around, and talk about and forward to their friends and things like that. Do you feel like you have a sense of this point of... how did your list grow to the size that it did? How are people finding it now? Is it now that you do have a more active Twitter presence? Is it through that, how do you find subscribers?

Kevin (18:23):

So I do also a bunch of... I have a podcast, there's a bunch of different media type, alternative media finance stuff. And I was lucky enough to get involved in that, and people would phone and ask for me to appear on their podcast. And I remember I was so scared the first time I did it, and I stumbled, and I thought to myself, "I'm never going to be asked again." And then luckily enough, they took pity on me and they asked me to come back. And I just... for the longest time I said to myself, "Just keep doing it until you get better at it." Just like my writing, I felt like the same way, I was like, "Keep doing it until you get better at it, and you will get better. It's like anything else, you practice long enough and you get better at it."

Kevin (19:08):

And I forced myself, people would see it and I'd force myself to say yes to radio interviews. So I remember I would go down, and it didn't matter if it was a Saturday morning show, that probably only 200 people were listening to. I forced myself to do it, just so I would get practice speaking. So I've been lucky enough to have a presence in this kind of alternative finance community, that's helped me with getting exposure. And so, that's one of the big things. And the Twitter, I kind of figured by now, everyone that follows me on Twitter, probably knows about what I do. It's not like it's going to be a surprise that they kind of find that I write this letter, but it's just... what it does is, every now and then on Twitter, I'll do something.

Kevin (19:56):

I remember I made this one tweet storm, I was on vacation, I had this real big view about something and I made this tweet storm and I made it funny. It's kind of almost like one of my letters, but I did it on Twitter and it went viral. It just got over a hundred thousand people passing it around. And all of a sudden, somebody that had a radio show on SiriusXM, asked me to come and talk about it. And so I went on to that, and then it just kind of, then you get more and it just kind of builds on itself that way. So, the one piece of advice I'd give is, just keep producing content and it's going to go slow at first. But then the power as I say, the power of compounding will cause it to accelerate, and then all of a sudden your first from 100 to 200 Twitter followers is tough. But then from 1000 to 2000 is actually almost easier.

Nadia (20:54):

It's interesting to think about all these different interviews, or sort of public artifacts that you're leaving around. It's like people end up finding those later, right? Like someone is probably always discovering some interview you did that was pretty popular. And so every time they find that, it's almost like a passive income for getting more subscribers or something because they're just littered around the internet.

Kevin (21:15):

Right. And you know what the problem is? I did this one, it was called Interview With Traders, and I am hesitant to say, because everyone's going to go listen to it. And it was one of my first ones I did and I really wasn't very comfortable. I didn't know how to speak properly. Not that I'm great now, but I was really bad then. And I just... even now, I cringe as I think about it, but I didn't realize it. When afterwards I asked the fellow, "How many people do you have listen to this?" He goes, "I don't know, 60, 80,000." I was like, "What?" I was like, "I just spoke to a football field. Right?"

Kevin (21:47):

And to this day, I still have people coming to me and saying, "I just stumbled upon your interview chats with traders." And I completely agree with your analysis that those kinds of things, when you get those opportunities, it stays on the internet forever. They say, what goes on the internet never leaves and stuff. I guess, there's terrible things when something bad stays on the internet, but there's also good things when something good like that stays on the internet.

Nadia (22:15):

Do you ever find that you hit plateaus with growing your lists? You were saying, 100 to 200 is hard, getting from a thousand to thousands is easy. Is there a point where just like ... I think we've talked a fair amount now about how to get your first hundred subscribers on it, because it comes from friends and family and you're sort of just passing things around, but then sort of that longer term growth, was there a point where you were just like, "I don't actually know how to get more people coming in?"

Kevin (22:47):

I didn't actually think about it like that. I just kept thinking about doing what I do, and I just thought, "Okay, I'm going to do things that interest me and I'm going to continue doing it and hopefully it interests other people." And I just always would say yes to any opportunities and it's definitely lumpy. It doesn't come in a nice smooth, steady plateau, like that one chance freak, tweet storm that I did that. Then I got on to SiriusXM and I was shocked. My Twitter exploded, my followers exploded from that. You'd be surprised. I might've been sitting around kind of incrementally going up, up, up a little bit, a little bit, a little bit, and then there's this one opportunity and then all of a sudden, boom, it accelerates from there again. And now it’s sideways again, blah, blah, blah.

Kevin (23:31):

And then the next thing will happen. And maybe one day it'll stop growing, and they'll plateau. And that's so be it and that's life. But at the end of the day, I don't actually sit around trying to do that too much because the way I operate it, I write stuff that I would like to read. And I'm almost just doing it for myself, and then hoping that I'll find my audience that also likes to read it. And I really think that's important because there's lots of times that I've kind of been tempted because I've seen, "That article there, if I did that, I bet you I could get a lot of people that would follow me."

Kevin (24:12):

But then I wouldn't really be doing it, things that I'm truthful for and it's not something that would be really me that would be almost like a business that's like, I don't know. I wouldn't want to have my name on that. I don't know how to describe it, but I want to do stuff that I'm proud of, that I believe in. And hopefully, if I keep putting it out there, people will find it and other people that kind of feel the same way as me. I'll find my audience.

Nadia (24:37):

I really love that. I think it's also, I feel like having that sort of attitude is what will keep people writing in the long-term as well. Because once you're... if you're thinking about in terms of, well what am I going to do, that's going to get a big hit? Or what are we going to do that other people are going to like? Versus, "I like doing this thing, and I'm just going to keep doing it and write the things that I want to read." And you could do that indefinitely. Right?

Kevin (25:00):

Right, yeah. And if my list goes down, like so far I've been lucky that it hasn't, but if it goes down, so be it. And those are my crew. And those are the people that I'll write for. I can't tell you how many times I've been writing. And I'm glad that you find it fun, because I also find it fun and I'm laughing as I write it sometimes, in there thinking about it, I'm like, "I'm making a funny picture." And it just makes me laugh, and I just, I get joy from it. And ultimately, I think that comes through. I think people see that I enjoy doing it and that's important. And above all else, I don't want it to be a job that I'm like, "I got to write again."

Nadia (25:37):

Right.

Kevin (25:37):

And the moment it does that, I'm probably not going to be writing stuff that people really want to read.

Nadia (25:44):

Yeah, I love that. And curious, you've been writing since before Substack existed. And now you're on Substack. But when you started, it sounded like it was something you were doing for friends. And so, I guess sort of from an infrastructure perspective, what were you using to ... at what point did you even start collecting email addresses, and how did you start managing that? And then, at what point did you decide to move over to Substack?

Kevin (26:13):

Okay. So, you're right. I've done a variety of different platforms. I think, let's go through them all. Probably started on WordPress, moved to Squarespace, eventually went to Jekyll, which is a static blog, and wrote our own... I had my old business partner who would write code for me. Most of the time with the emails, I think I exclusively used Mailchimp. I would tie it into the websites. And so, that was kind of the tool that I used for the longest time, whether it be a WordPress, Squarespace or our own Jekyll kind of statics blog, we would usually send out the emails via Mailchimp.

Kevin (27:00):

Now Mailchimp is fine when you've got a small little list that you're doing for friends and family. Once you get to a larger number, it starts costing and it actually starts costing a lot. And it's one thing to write and spend your time for free. It's another thing to be sending out this list and shelling out 200 bucks a month, for something that you're giving away. And so, this is one of the things that I found. I was actually, I hit this point where, I kind of was looking for alternatives to Mailchimp, because I found Mailchimp very expensive and not everything I was hoping for in terms of ease of use.

Kevin (27:43):

And I went and looked, and I experimented with Sendy, which is in a platform using Amazon's email sending, but that's complicated. You had to go make Amazon, kind of, instance in the cloud. And although I did figure it all out, it wasn't something that was easy. Then I went and looked at, there was another one that I can't remember what it was called, Sendmail. There's a variety of different, cheaper ones that I kind of looked at. And I'll be truthful, this is how I came upon Substack.

Kevin (28:16):

One of my buddies writes a blog on here, and he had sent me something and I liked the looks of the email that he sent and I kind of looked at it and I was like, "What's this all about?" And I read about it, and then I saw that you guys offered the ability to go and to send emails for free. And I thought to myself... And I was like, "You guys said it right there." You said, "Look, if you never charge for your letter you can still send it." And I guess I'm going to end up being proof that your marketing strategy works, because I ended up choosing you guys. That's how it started.

Kevin (28:55):

I sent you off my list, and I imported it and I started sending, using your Substack to send off my emails because I was looking for an inexpensive way to send it off. When I first sent you the list, I had unfortunately at one point gotten, I don't know how to describe this. Some Chinese like bot program imported, it went bananas one time and my email list went from 10000 to 30000. And then I thought I cleaned it out, but I hadn't cleaned it out properly. And so when I imported it all, and then sent out my first email list, your tech staff looked at it and said, "A whole bunch of these aren't working right." They were going to some weird address. And I was shocked because here I was, I wasn't paying you guys anything and you guys were taking the time to come and say, "Look, there's something wrong here. There's all these crazy bot ones. Why don't we clean this out for you?"

Kevin (29:54):

And I was like, "I really like these guys. This is terrific." And I was just shocked, because literally I didn't ask you, you guys came and said, "This will work a lot better this way." And I thought, "What a great firm." And so I kept looking, and then I hit this point where I decided I was going to pay for it, charge for my letter. And so I had gone back and forth between maybe using Ghost, which is kind of a WordPress platform, that also includes the ability to send off emails. And I was going and looking at it and then I was looking at the whole, how I would go about taking payments. And then I looked at your solution and I thought to myself, "I've already been impressed with their service. Here it is. These guys seem to really know what they're doing, and I can go and turn this on basically overnight, really easily turn this on. And they'll handle all of the billing and all that stuff."

Kevin (30:52):

And I think it's more than a fair price. How much you guys take. I think it's completely fair and I thought, I'm giving you guys the benefit of the doubt. I'm going with you guys. So, your marketing of giving this wave, allowing people to send free emails worked completely with me, because I ended up using you in the long run for it. And I can tell you, I've been nothing but ecstatic about the way that you've helped me go through this whole process. I've never charged for anything, so I had no clue when the Stripe payments started coming in. I was nervous about stuff.

Kevin (31:25):

Somebody emailed me back and said, "No problem." I had some problems with some visas not going through. I emailed, and it was again taken care of right away. It was a wonderful experience, and I can't tell people enough how pleased I've been with Substack as a kind of a model for me. Because one of the things is that, I'm a single in terms of, I don't work for a firm. I just work for myself. And the time, in terms of billing and all that stuff, is really important to me. I don't have time to do all this. And so, I found it a seamless, wonderful experience, and I'm just so pleased that I chose Substack. I know that sounds a little like I'm doing a sales pitch, but it's true.

Kevin (32:16):

I remember one time somebody said, they emailed me and said, "I see you on Substack. Do you mind if I talk about it?" And I say, "You can talk about it anytime you want, because I'm so happy with these guys." It's been so great from that experience. Listen, I still have, just to show that I do have my complaints. The fact that I have to put Substack in the... I can't have a custom domain. I'm sure you guys hear that all the time.

Nadia (32:42):

We've heard it, once or twice.

Kevin (32:46):

So, I will say, that is my one huge kind of... listen, I actually thought about it long and hard because of that custom domain. And I ultimately said, "You know what? I'm going to not bother. I'm going to live with the domain." And I would highly suggest everyone else do the same and not worry about it. But if we're chatting now, here's another vote for a custom domain.

Nadia (33:11):

It is definitely something we've heard from a lot of people, and something that we're trying to solve.

Kevin (33:14):

Yeah, fair enough. I get it. There's some bigger issues and it's not easy to kind of do that, but anyway, it's been-

Nadia (33:24):

Good to hear, despite that you're still with us, which is awesome.

Kevin (33:27):

Yeah.

Nadia (33:27):

We're really glad.

Kevin (33:28):

Listen, at the end of the day, adding a Substack isn't that big a deal. Just for those technically inclined, I just really pointed, I forwarded the domain so that when you do go to my root domain, it actually goes to the root domain.substack.com. So, it's not like people had to redo their links and stuff like that, it actually can still work. It just doesn't work as clean as it might be.

Nadia (33:58):

That's all right. Yeah. Because you used to have the macrotourist.com which was... you had your blog hosted on a separate website. Right?

Kevin (34:05):

That's correct.

Nadia (34:05):

And then you also did your email newsletter through Substack. And then when you decided to go pay it or add paid subscriptions, you decided to just sort of combine those two things together.

Kevin (34:18):

That's right. I just didn't want to bother, I wanted to keep it all one and the same. And I've been really happy with the whole experience. I find it very pleasing to the eye, and it's easy. It's not too complicated. It's very snappy. Some of the, like when you get a WordPress that has too many plugins and stuff, it very quickly kind of blogs down. I've found none of that. I've had no problems with any sorts of not saving, writing half a post and losing it. That hasn't happened at all. It's been nice, it's clean, and it works. And that's the most important thing. It allows me to spend more time writing, and less time worrying about technology, which is ultimately what I was looking for.

Nadia (35:02):

That's exactly what we aim to do. I would love to hear more just about, I mean, you decided to launch paid subscriptions, I mean really you just switched completely to paid, pretty recently and so, yeah, I'm curious, after years of writing for free, what made you decide, “screw it, I'm going to go add paid subscriptions?”

Kevin (35:23):

So, I did it for a variety of different reasons. I guess at a certain point, I kind of felt like, "Okay, I'm offering enough value that I feel like I should get paid for it." So, and I looked at a lot of times, other people would send me notes and say, "Listen, I'm doing this for... I'm making money on this and you're doing this for free. Can you stop it?" They were like kind of mad at me. So, and it was increasingly taking time, and that was the other thing, as I did it more and more, took time. And I found that there was more and more people that were kind of contacting me as I did it. Whereas at first, it was great when they were contacting me and I'm still appreciative of everyone that ever contacted me.

Kevin (36:09):

But it was getting to the point where I was having... I was becoming overwhelmed with the amount of contact that I had, and I had a choice. I could either just stop, start ignoring people, which I don't really like doing, or I could turn this into a business, which was always kind of my dream and my goal. So, I decided just to take the leap of faith and to turn it into a paid subscription. And so far so good. There's been a lot of long-term, long time MacroTourist readers that were very supportive and I'm appreciative of all those who just immediately signed up.

Kevin (36:46):

And if they're listening now, thank you very much for your business. It enables me to actually focus more time on it. I feel like my last posts have been better than they ever were, because now I feel like it's a job and I can actually devote more time without worrying about having to make a living as much on the side.

Nadia (37:06):

Can you talk to me a little bit of your thinking of ... so a lot of writers that add paid subscriptions, also continue to have some free posts, but you went 100% paid and you just said, "You know what, it's just entirely a fee." I think you used the term a fee-based newsletter. What was your thinking on that, of did you consider doing some free posts?

Kevin (37:25):

Right. So, I did listen to that. In fact I see that you guys actually encourage writers to do that. I chose not to, and I'll tell you why. I also chose to do no discounts. And I know that your system offers discounts, and I just said, "No, this is the deal, I don't want people to sign up for a letter and then feel like, if they waited six months, they would've got a better price." So I committed that there's nobody who's going to get a better price, wasn't going to be offering deals later to get more subscriptions.

Kevin (38:07):

And then in terms of the free stuff, although I haven't completely kind of eliminated it, I don't think that it's fair to those who are paying for me to do it, in terms of giving it away. And so, it just kind of, it was what made me feel comfortable. It's like I was kind of thinking about it from a point of view of, if I was buying the product, what would I want? And I'd want it to be an exclusive service that I've paid this money for, and I don't want it going out to the other people for a lesser price.

Nadia (38:44):

Yeah, that was really cool. And I think it makes sense too, given your particular audience. And it sounds like it's... I mean, I love the phrasing of your announcement too, where you started in respecting your readers’ time. It really came from, to me it seemed like it came from a place of understanding what your readers wanted, what they valued, and doing it in a way that was uniquely yours, and unique to your audience. And it seems to be going really well. So...

Kevin (39:07):

Well, yeah, I promised them, I said, over the years when I've collected the emails, I've often said, "You will not get spammed by me. If you're like, basically, I'm either going to be sending you content that I'm proud of or that's it." And so, when I went kind of pay, I decided to send one announcement. I said, "This is the announcement. I'm doing this, these are the reasons I'm doing it. This is what I hope to make better." And I went through my list of kind of improvements, I was going to make to my letter and then I said, "And I won't be bothering you again with, about this."

Kevin (39:43):

Because one of the things that really bothers me, as someone who's signed up for these, are those emails that are basically nothing more than just kind of marketing material. And they're kind of half written articles that just end up being teasers, to try to get you to pay for the whole thing. And that just always left me with a bad taste in my mouth. So, I vowed that I was never going to do it. And I've stuck to that philosophy and that promise I gave to my readers.

Nadia (40:17):

Love that. How did you decide on pricing? People are paying $35 a month, is that right? For ...

Kevin (40:24):

Yeah, so it's $35 a month or $350 for a year. I looked at other people's, basically the competition and even at that price, some of my buddies that also write letters told me I was too low. I did want to go... I didn't want to start too high. I figured that this is the way I thought about it. I can always raise, I don't want to ever lower. So, I kind of thought I'm going to go to my level, that at that point, if it doesn't work at that price, then I don't want it, then that's, I don't want to do it for money. And so, it doesn't matter. And that's how I looked at it.

Kevin (41:05):

Now you have to realize though, that my audience is a little more niche than other people, so I'm never going to get the million subscribers. This is just never going to happen for me. It's like I write about very... you have to be very interested in markets to read my letter. And so for me to price at a level where I'm going for a million people, it's just never going to work. I'm just not going to get it. So, I would rather pick something that I think is fair. And as I said, I ended up choosing a level that was comparable. I picked other newsletter writers that do it, and I said, "Okay, that's where they are. I'll go on the lower end." And as I say, I can always increase it later if it's successful.

Nadia (41:54):

And it sounds like writing for a smaller niche. It's almost like one of your goals. At least from reading your announcement where you mentioned, you're able to add comments now, because before, when you had free posts, you didn't really want random people kind of coming in, or just sort of having this fire hose of commentators, and feeling sort of overwhelmed by reader requests. And so, having this, having paid subscription sort of, it allows you to sort of focus on this smaller audience of people that are more dedicated, I guess.

Kevin (42:27):

That's for sure. And one of the things that I like to say is, that was again, a reason I chose Substack is I was like, "Look, they have comments. It's easy." And in my post that you read, I obviously, I said why I previously didn't have comments because free comments, there's a very famous website in the financial community called Zero Hedge. And Zero Hedge has got many, many, hundreds of thousands of readers. And he used to go and republish my pieces. And over the years, I would often let a lot of people republish it. I was basically, "Yeah, sure. It's free, more exposure for me the better." And so, when I would go look at the comments I was horrified, and it wasn't just my articles.

Kevin (43:13):

It was just like, in general, comments, just like, I don't know. It seems to be, it's even worse than Twitter. It was just horrifying. It was like... and although I try not to let it bother me, I'm still human. And so, I never turned on comments because it seemed too easy for the trolls to come out. And so now I was like, "Okay, if somebody's paying and they have an issue with me, then I don't mind them putting in the comments. I don't mind us talking about it as adults and respectful adults." And I think you get rid of all the trolls. And it's not to say people won't disagree with me. I have never had a problem with people disagreeing with me, or wanting to present a different view.

Kevin (43:56):

It's just those people that almost just seem like they want to fight for the sake of fighting. And generally those people that do that, they're not willing to pay per month for it. So, one of the things was, it was a pleasure to turn on the comments and I've loved it. It's great. And I get to interact, and get to see some feedback and stuff, with my readers and it's been terrific that way. And it's actually, it's been a kind of, one of the better parts of going to paid, is that I've been able to turn on the comments.

Nadia (44:27):

Yeah, that makes perfect sense. Definitely something we've heard from other writers as well.

Kevin (44:32):

That's good. Yeah.

Nadia (44:34):

Yeah. There's something about adding. If you care enough to pay and comment, then you're probably a different kind of person than that.

Kevin (44:41):

Right, yeah. I just didn't see us getting rid of the trolls, and that's all... that was just basically it, as much as I try to not let them bother me, they just do. And you're just like... and I do have a funny story though, about trolls on Twitter. So a lot of people block on Twitter. And the thing about when you block is that the other guy knows the other person knows that you blocked them. And I refuse to let anyone know that they've gotten to me. So I just mute them. So, meaning that I don't see what they're doing. So they're just kind of yelling at me and doing it. I kind of get a chuckle thinking about them just yelling into a void.

Nadia (45:17):

Love it.

Kevin (45:19):

Because if you block them, then they know they got to you. So nobody ever knows who I've viewed it or not.

Nadia (45:26):

I was talking to somebody who says he does the soft blocking a lot on Twitter, where you just, you force someone to unfollow you. And then they get really frustrated. Because they're like, "I thought I followed this person. And then they keep getting unfollowed." But it's not like blocking. It's like, this person blocked me.

Kevin (45:39):

I didn't know. You could force unfollow?

Nadia (45:43):

Yeah.

Kevin (45:44):

I didn’t know that!

Nadia (45:44):

I think it's like, you block and then you immediately unblock. I've done it with a couple of people on Twitter.

Kevin (45:48):

I didn't know that.

Nadia (45:49):

And then they're not following anymore. So, if you want a new, subtle trolling patrol strategy.

Kevin (45:55):

That's it, there we go.

Nadia (45:58):

Yeah, I mean, so just to sort of wrap things up, is there anything you've discovered since getting paid that was surprising to you? Is there anything you're going to change based on reader feedback? What are your plans for the future?

Kevin (46:11):

Well, has anything changed? Well, there have been some things, unfortunately I went paid right in front of this financial crisis, which is kind of like some people said, "Terrible timing." And other people said, "Great timing." And I will tell you that, I have been completely, unitedly going crazy from the markets, because this is really unprecedented times. It's been a hundred, it's been a century since we've had a pandemic. And the markets just don't know how to deal with it. So it's been very busy that way.

Kevin (46:46):

And so, I haven't had a chance to really do some of the things that I wanted to do, in terms of putting portfolio recommendations and stuff like that. So, although I've turned on comments and I've done a few other things that I said I wanted to do, my full kind of move into, my kind of end version of my letter is not quite there yet, but having said that, the comments have been very helpful. It makes me understand what people are interested in reading. So, there's been a couple of ideas. I have a list of posts that I want to write, and I kind of just write them down quickly. It's been great kind of... one of the things is that a lot of these people that used to email me and I would take the time to email them back,

Kevin (47:30):

I said, "Listen, why don't we do this so everybody can read it?" And it’s not just me and you that are conversing, and everyone can gain from the knowledge. Because a lot of times, listen, the people that are reading my letter are often smarter than me, and actually have much more knowledge, especially about certain industries or certain parts of the market. For me, I call myself the MacroTourist. And the reason is that, for those who don't know finance, it's actually a derogatory term.

Kevin (47:57):

And what it means is, it used to be traders that would come in and just kind of wander into something, not really knowing what they were doing, a big macro trade and then they were tourists, and then they would make a mess and then leave. And so, it was kind of part of myself, making fun of myself kind of style, to call myself that. But one of the things is that, when I write about such a variety of different topics, meaning that, I don't just stick to one topic, I basically work on a whole bunch of different things, that there's people who know more and they might read my letter and kind of comment, and give me ideas or give me some more kind of color, in terms of how it's working.

Kevin (48:39):

And sharing that with the kind of my reader and my community actually really helps everyone, not just me. So that's, again, why I like the comments so much. And in terms of other things that I'm going to do, no, I actually just... I can't tell you how much I've just been pleased, how easy it was, how great. I'm just going to continue doing what I love doing, which is writing posts and letting you guys handle all the back office stuff.

Nadia (49:08):

Sounds good to us. Where should people find you if they want to check out and follow your work?

Kevin (49:13):

Well, so I guess, I should give you my Substack email. I mean, our Substack kind of domain. And so, it's themacrotourist.substack.com. And if you want to follow me on Twitter, you can go ahead @kevimuir. You're from San Francisco, so you know all about John Muir.

Nadia (49:32):

That's right.

Kevin (49:33):

And so, I can always tell people from the West, because they always ask me if I'm related to John Muir.

Nadia (49:38):

And what's the answer?

Kevin (49:40):

No, you know what? Muir is a pretty common last name, so I don't think so. It is always fun though, going and seeing your woods and-

Nadia (49:49):

Yeah, you got to pretend ...

Kevin (49:51):

Yeah, that's right.

Nadia (49:53):

These are my woods. Awesome, thanks for joining and chatting with me. It's a really great conversation.

Kevin (50:00):

Well, thank you very much for having me and thanks for the great product. I really appreciate all your hard work, and I look forward to being part of your community for some time to come.

Nadia (50:08):

Thanks.

Get on the email list at on.substack.com

We spoke with Erin Cook of Dari Mulut ke Mulut, a publication covering news across Southeast Asia.

Erin started her newsletter early in her career while working for a daily newspaper in Jakarta, Indonesia. After she found that broader regional news was lacking, she decided to expand her focus across the ASEAN region.

We spoke to Erin about how international journalism has changed over the years, how independent writing helps her be more nimble as a reporter, and why it pays to have friends that tell you to charge more.

Links

* Dari Mulut ke Mulut, Erin’s newsletter

* Indonesia, dll, Erin’s podcast, co-hosted with Hayat Indriyatno, about Indonesia

* Ayolah, Erin’s spinoff newsletter covering the Indonesian elections

* How Walt Hickey of Numlock News expanded to multiple newsletters

Highlights

* (07:37) How international journalism is changing

* (14:29) Balancing newsletter writing, podcasting, and a weekly column

* (18:43) Finding and reporting on stories in low-coverage regions

* (25:29) How she grew her list

* (27:58) How she thinks about paid subscriptions

* (34:44) Starting a spinoff newsletter, Ayolah, to focus on the elections

* (37:21) Subscription pricing for an international audience

On covering regions that are overlooked by newspapers:

It's hard for the big mastheads to take a punt on a country like Laos or an issue like coronavirus in Laos. But for me, I already know that my audience is interested. They've signed up specifically for news on countries like Laos. So for me it's easy to sneak under the radar and I know people are interested, so it's a no-brainer for me.

On the importance of building an audience before charging:

...you can't just be like, "I'm doing this and here's the paywall." No, you do have to establish that very quickly. And if you're someone like Matt Taibbi, he's got his credibility built in. But if you're someone like me, you've got to just hustle it out for a little bit longer than maybe you'd like to.

Transcript

Nadia: (00:35)

You write a publication called Dari Mulut ke Mulut. Did I say that correctly?

Erin: (00:40)

Pretty close, yeah.

Nadia: (00:41)

- which is a shortcut to Southeast Asia, you report on news and analysis and features from across the region.

Erin: (00:50)

Yes.

Nadia: (00:50)

All right. I thought it was cool that you mentioned the meaning of your publication.

Erin: (00:58)

It's such a great term, it comes from Indonesia. And Indonesia has all these brilliant idioms. So Dari Mulut ke Mulut literally translates to, "From mouth to mouth," but it's used more as both word of mouth and gossip, so I thought it was perfect for what I was wanting to do.

Nadia: (01:16)

Yeah, I think it plays really well into this very conversational writing style which you have, which actually feels like someone is just learning from someone on the ground the gossip, but then with a deeper reporting lens.

Erin: (01:27)

Yeah, well, that's definitely the aim.

Nadia: (01:30)

It's coming across great. I’d love to hear just a little bit about your background and how you got here. I know you've had experience writing and covering the Southeast Asia region for a while.

Erin: (01:40)

Yeah, I started the newsletter very early on in the career, actually. I was initially, probably like a lot of Substack users, started off on a Tinyletter years ago. And I was working for, in Jakarta, one of the English daily newspapers there. And it was really interesting to be in what's probably one of the biggest cities in the world in such a fascinating region, and really struggling to find news from elsewhere within southeast Asia. So that inspired it, so I was just reporting on Indonesia, but there'd be all these links between Indonesia and Singapore or Malaysia or the Philippines. But you'd have to go to a Singapore news website to find out more about that aspect, or a Filipino news website to find out more about them. So I really just wanted to bring it all together in one place so it's easier for everybody else.

Nadia: (02:36)

Can you give us just a little bit of, I guess, context for people that don't live in Southeast Asia? What is the coverage like there right now?

Erin: (02:44)

No, that's a good question. I'm very shorthand about it now after a few years. So it's based around the ASEAN bloc, which is the Association of Southeast Asian Nations, which is vaguely the European Union of southeast Asia. And that's, I can list them all if you like?

Nadia: (03:04)

Curious, yeah, why not?

Erin: (03:06)

Yeah, so we go Indonesia, Philippines, Singapore, Malaysia, Thailand, Brunei, Cambodia, Laos, Vietnam, Myanmar. And I also include Timor-Leste in there, which is not yet a member of ASEAN, but I really hope one day they will be. So yeah, like to include them in there as well.

Nadia: (03:28)

So you're in Indonesia but you're covering Southeast Asia. Are there other outlets that do this sort of regional focus? How did you decide where to narrow or expand your scope, since you could be reporting just on Jakarta, you could be reporting on the whole region?

Erin: (03:43)

I think Jakarta is really interesting because it's home to ASEAN. So it's got the Secretariat there, and the areas that I've lived in in Jakarta is very close to there. So ASEAN is probably more prominent in Jakarta than it is anywhere else in southeast Asia, so that really piqued my interest. I'm from Australia, and we don't really hear that much about ASEAN. So I just followed that for a while, and then was a bit half-interested and half just seeing that there was a gap there that a newsletter could fill.

Nadia: (04:23)

Do you feel... I guess I'm just imagining if you were a newspaper employing 50 people or whatever, you'd be able to cover an entire region. For you personally as an independent writer, how are you finding new sources and things to write about in areas that you aren't physically in?

Erin: (04:39)

It's really, really difficult. So I've been doing this now for about four years, I think with the last 2 1/2 on Substack. So the first year was really, I'll never go back and reread old newsletters. It would be a cringe.

Nadia: (04:55)

Never read your own writing.

Erin: (04:55)

Exactly. But I've been lucky to be in the region when there have been momentous occasions. So I've been here for huge elections and important movements with the ASEAN bloc. So there's always something happening, and when that's reported on by some of the brilliant journalists from across the region it paints a broader picture of how the region got here. And I'm very lucky that I get to travel so much because of how close-knit ... Well, until recently, of course, because of how close-knit the region is. It's really easy to get from Jakarta to Singapore, to Singapore to Bangkok, or over to Manila just for a couple of days. It feels exciting, everybody wants to talk about what they're covering, what they're reporting on, what they're reading. And just buy a couple of beers and soak that up. Yeah.

Nadia: (05:57)

I'm picturing almost like really a literal manifestation of the name of your publication.

Erin: (06:03)

Pretty much, yeah.

Nadia: (06:04)

Sort of like passing on through word-of-mouth from friends and things in different countries.

Erin: (06:07)

Exactly. And it's really cool because it just starts up being journalists whose work I've noticed over the years and will go now on my way to ... If I see their byline I'll definitely be clicking on it and reading that. And everybody's so nice and friendly. So just send an email, "Hey, I'm coming to KL," and they'll be like, "Great. See you on Wednesday."

Nadia: (06:29)

Do you find that process of getting new information and talking to people and having sources, is it different from ... Do you approach it differently as it's your newsletter, you can write about what you want, versus working as a journalist at a newspaper?

Erin: (06:44)

No, definitely. I think that more traditional ... I've been thinking about this recently as the industry changes dramatically over the last few weeks. I don't think, yeah, it doesn't compare to regular on-the-ground report…

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com

We spoke with Erin Cook of Dari Mulut ke Mulut, a publication covering news across Southeast Asia.

Erin started her newsletter early in her career while working for a daily newspaper in Jakarta, Indonesia. After she found that broader regional news was lacking, she decided to expand her focus across the ASEAN region.

We spoke to Erin about how international journalism has changed over the years, how independent writing helps her be more nimble as a reporter, and why it pays to have friends that tell you to charge more.

Links

Dari Mulut ke Mulut, Erin’s newsletter

Indonesia, dll, Erin’s podcast, co-hosted with Hayat Indriyatno, about Indonesia

Ayolah, Erin’s spinoff newsletter covering the Indonesian elections

How Walt Hickey of Numlock News expanded to multiple newsletters

Highlights

(07:37) How international journalism is changing

(14:29) Balancing newsletter writing, podcasting, and a weekly column

(18:43) Finding and reporting on stories in low-coverage regions

(25:29) How she grew her list

(27:58) How she thinks about paid subscriptions

(34:44) Starting a spinoff newsletter, Ayolah, to focus on the elections

(37:21) Subscription pricing for an international audience

On covering regions that are overlooked by newspapers:

It's hard for the big mastheads to take a punt on a country like Laos or an issue like coronavirus in Laos. But for me, I already know that my audience is interested. They've signed up specifically for news on countries like Laos. So for me it's easy to sneak under the radar and I know people are interested, so it's a no-brainer for me.

On the importance of building an audience before charging:

...you can't just be like, "I'm doing this and here's the paywall." No, you do have to establish that very quickly. And if you're someone like Matt Taibbi, he's got his credibility built in. But if you're someone like me, you've got to just hustle it out for a little bit longer than maybe you'd like to.

Transcript

Nadia: (00:35)

You write a publication called Dari Mulut ke Mulut. Did I say that correctly?

Erin: (00:40)

Pretty close, yeah.

Nadia: (00:41)

- which is a shortcut to Southeast Asia, you report on news and analysis and features from across the region.

Erin: (00:50)

Yes.

Nadia: (00:50)

All right. I thought it was cool that you mentioned the meaning of your publication.

Erin: (00:58)

It's such a great term, it comes from Indonesia. And Indonesia has all these brilliant idioms. So Dari Mulut ke Mulut literally translates to, "From mouth to mouth," but it's used more as both word of mouth and gossip, so I thought it was perfect for what I was wanting to do.

Nadia: (01:16)

Yeah, I think it plays really well into this very conversational writing style which you have, which actually feels like someone is just learning from someone on the ground the gossip, but then with a deeper reporting lens.

Erin: (01:27)

Yeah, well, that's definitely the aim.

Nadia: (01:30)

It's coming across great. I’d love to hear just a little bit about your background and how you got here. I know you've had experience writing and covering the Southeast Asia region for a while.

Erin: (01:40)

Yeah, I started the newsletter very early on in the career, actually. I was initially, probably like a lot of Substack users, started off on a Tinyletter years ago. And I was working for, in Jakarta, one of the English daily newspapers there. And it was really interesting to be in what's probably one of the biggest cities in the world in such a fascinating region, and really struggling to find news from elsewhere within southeast Asia. So that inspired it, so I was just reporting on Indonesia, but there'd be all these links between Indonesia and Singapore or Malaysia or the Philippines. But you'd have to go to a Singapore news website to find out more about that aspect, or a Filipino news website to find out more about them. So I really just wanted to bring it all together in one place so it's easier for everybody else.

Nadia: (02:36)

Can you give us just a little bit of, I guess, context for people that don't live in Southeast Asia? What is the coverage like there right now?

Erin: (02:44)

No, that's a good question. I'm very shorthand about it now after a few years. So it's based around the ASEAN bloc, which is the Association of Southeast Asian Nations, which is vaguely the European Union of southeast Asia. And that's, I can list them all if you like?

Nadia: (03:04)

Curious, yeah, why not?

Erin: (03:06)

Yeah, so we go Indonesia, Philippines, Singapore, Malaysia, Thailand, Brunei, Cambodia, Laos, Vietnam, Myanmar. And I also include Timor-Leste in there, which is not yet a member of ASEAN, but I really hope one day they will be. So yeah, like to include them in there as well.

Nadia: (03:28)

So you're in Indonesia but you're covering Southeast Asia. Are there other outlets that do this sort of regional focus? How did you decide where to narrow or expand your scope, since you could be reporting just on Jakarta, you could be reporting on the whole region?

Erin: (03:43)

I think Jakarta is really interesting because it's home to ASEAN. So it's got the Secretariat there, and the areas that I've lived in in Jakarta is very close to there. So ASEAN is probably more prominent in Jakarta than it is anywhere else in southeast Asia, so that really piqued my interest. I'm from Australia, and we don't really hear that much about ASEAN. So I just followed that for a while, and then was a bit half-interested and half just seeing that there was a gap there that a newsletter could fill.

Nadia: (04:23)

Do you feel... I guess I'm just imagining if you were a newspaper employing 50 people or whatever, you'd be able to cover an entire region. For you personally as an independent writer, how are you finding new sources and things to write about in areas that you aren't physically in?

Erin: (04:39)

It's really, really difficult. So I've been doing this now for about four years, I think with the last 2 1/2 on Substack. So the first year was really, I'll never go back and reread old newsletters. It would be a cringe.

Nadia: (04:55)

Never read your own writing.

Erin: (04:55)

Exactly. But I've been lucky to be in the region when there have been momentous occasions. So I've been here for huge elections and important movements with the ASEAN bloc. So there's always something happening, and when that's reported on by some of the brilliant journalists from across the region it paints a broader picture of how the region got here. And I'm very lucky that I get to travel so much because of how close-knit ... Well, until recently, of course, because of how close-knit the region is. It's really easy to get from Jakarta to Singapore, to Singapore to Bangkok, or over to Manila just for a couple of days. It feels exciting, everybody wants to talk about what they're covering, what they're reporting on, what they're reading. And just buy a couple of beers and soak that up. Yeah.

Nadia: (05:57)

I'm picturing almost like really a literal manifestation of the name of your publication.

Erin: (06:03)

Pretty much, yeah.

Nadia: (06:04)

Sort of like passing on through word-of-mouth from friends and things in different countries.

Erin: (06:07)

Exactly. And it's really cool because it just starts up being journalists whose work I've noticed over the years and will go now on my way to ... If I see their byline I'll definitely be clicking on it and reading that. And everybody's so nice and friendly. So just send an email, "Hey, I'm coming to KL," and they'll be like, "Great. See you on Wednesday."

Nadia: (06:29)

Do you find that process of getting new information and talking to people and having sources, is it different from ... Do you approach it differently as it's your newsletter, you can write about what you want, versus working as a journalist at a newspaper?

Erin: (06:44)

No, definitely. I think that more traditional ... I've been thinking about this recently as the industry changes dramatically over the last few weeks. I don't think, yeah, it doesn't compare to regular on-the-ground reporting, in that the people that I call up and have quick conversations with are always academics who have covered a particular niche for decades, or other journalists who are just pointing me in the right direction of which books to be catching up on. It's not so much getting out there and talking to regular people, which is one thing that I genuinely miss. And it's not so much ... I don't know, it's not as grinding, which is good. It's not the same, deadlines are self-imposed so it can be a bit more flexible.

Nadia: (07:37)

You mentioned everything that's been happening in the past couple weeks as you were explaining that. Which obviously can refer to a lot of different things right now, given that we're in the middle of it all. I don't know if you've seen, just because I live in my own bubble of, at least here in the US there's been a lot of talk just about media outlets shutting down and laying off workers and stuff. Is that something that is also being experienced abroad? Is the world of foreign news and journalism different in any way from ...

Erin: (08:04)

Yeah, from what we've seen, foreign journalism I think probably caught a bigger hit from the more broad collapse of print media in the last decade or two decades, or however long it is now, than it will during this particular crisis. There used to be dozens of foreign journalists in all of the major cities in Southeast Asia, and that's not really a thing any more. Which is a bummer, but on the other side of that, I think we're also seeing Western outlets, and I say that with US, Australian, and European ones particularly, that are a lot more ... And I think it's pushed by editors, a lot more interested and more trusting of having local reporters report on their own countries, which is a brilliant thing for someone like me who wants to really get to know the news.

Erin: (09:05)

It makes a lot more sense to have someone who's from Jakarta, speaks fluent English and fluent Indonesian, and knows the back story of every politician to be covering Indonesian politics than someone that's just been dropped in for three years and then moved on to wherever else is next. Which isn't to say that there isn't brilliant foreign reporting coming out of us foreigners, I think some of the most interesting stuff comes out of, when you arrive in a new place and you can truly see how different something is. Which I think is a problem that I face when I try to report on Australia. I think it's a problem a lot of people face when they report on their own thing. But I think we are heading into a really, really exciting time for Southeast Asia journalism, where yeah, there's just going to be more and more brilliant local journalists rising. And I think that should be applauded.

Nadia: (10:06)

This might be a really dumb question, but it's only because I don't know anything about this topic. Why didn't they employ more local correspondents before, or why is that a shift?

Erin: (10:17)

No, I think that's a fair question, because I think it's probably a diverse answer. So I think Southeast Asia, I definitely can't speak for anywhere else, but because of how ... This is a pretty deep one. Because of how colonialism worked across the region, there are some countries that are much more coveted in speaking other languages, like Singapore's language is English and Philippines, great English because of the Americans. And Malaysia because of the English. But then for countries like Indonesia, where there was, not everybody spoke Dutch anyway and English was great, but it's not at the same level that it is now, it would have been seen as a much better move for desks back in the olden days to send journalists from London or Sydney over to do it and work with local reporters who probably could have just done it themselves, to be honest.

Nadia: (11:22)

Got it. As I asked the question I realized I was probably walking into a history lesson.

Erin: (11:26)

There's so much interesting conversations that come out of that, because all around the region, so many of my good friends that I catch up with across the whole place are Thai or Indonesian or Filipino, and they have the most brilliant takes on this sort of stuff. So yeah, if any listeners are interested in that, search out more, because there's a lot of brilliant conversation around foreign journalists, foreign correspondents, and who can do it and who should be doing it.

Nadia: (12:00)

How are the newer correspondents making themselves known?

Erin: (12:06)

It's tough because especially in the very, very big cities, especially in Manila and Bangkok and Jakarta, where it's tough to rise to the top just because the pool is so big, but I think the answer is the same everywhere, and it's Twitter, which is for better or worse.

Nadia: (12:24)

The magical piece, yes. You see so many Substack writers that come in from these other public platforms where they've built an audience on Twitter, or we've seen Instagram, LinkedIn, surprisingly.

Erin: (12:40)

Oh, whoa, yeah.

Nadia: (12:42)

Just wherever. So you're building this audience elsewhere and then people are excited and engage with you there, and then Substack becomes this place to say, "Okay, I have a following, I have fans, and come talk to me over here in this more semi-private place." I see it as, one step leads to the other, which is nice.

Erin: (13:02)

Yeah, no, that's always amazing. Any time I see someone announce their new Substack they'll get hundreds and hundreds of retweets. I'm like, "Damn, all right, go for it."

Nadia: (13:14)

Yeah, really. More of that's happening lately too, which is great.

Erin: (13:19)

Yeah.

Nadia: (13:20)

So you write a newsletter, but then you also have a weekly column, and then you also have a podcast, is that right?

Erin: (13:25)

Yes, podcast is on hiatus at the moment, just because I've had to come back to Australia and it is pretty crazy over there in poor Jakarta, so we're just on break for a moment. But we'll be back.

Nadia: (13:41)

Got it.

Erin: (13:43)

And yet the weekly column with The Diplomat is very similar to the Substack publication, actually, but just with less jokes and a bit more serious.

Nadia: (13:55)

It's your professional face.

Erin: (13:56)

Yeah, exactly.

Nadia: (13:57)

Do you like having this balance of lots of different projects? That's something I really like about a lot of writers. You can express yourself in lots of different ways.

Erin: (14:05)

It's fun, isn't it? I feel like, what's that thing, you can't half-ass two things, you have to whole-ass one thing? I think I got too excited when I first realized that you could do all these cool things out there. Once I spent a year just working solely on the Substack, that's when it was much easier to turn these other projects into actual things. And it was so much better, actually worked out that time, yeah.

Nadia: (14:29)

How do you feel about expressing yourself through writing in a newsletter and speaking on a podcast? How do those two things compare for you?

Erin: (14:38)

Oh, I think it's very different. I think I'm always just going to be a natural writer. It's just easier to self-edit and work out what you're saying. And even with the podcast that I do with my friends at General Media, which is Indonesia dan Lain-Lain, they'll kill me if I don't shout it out. Even then it's very ... I don't know, just very nervous. But when you write you don't have that. You sit in your bedroom, and if it didn't work out you can just restart and send it an hour late.

Nadia: (15:14)

It's true. I do feel like, I don't know if other people feel this way, but I feel like I can ... So many people are either one or the other of, they really love expressing themselves through words and typing and really love expressing themselves in speaking in person. I tend to get a lot more tongue-tied speaking, which makes writing a lot more appealing.

Erin: (15:32)

Oh, for sure, for sure. I think it's a total skill to be able to just do that natural-sounding podcast thing. I'm not there yet. I'd like to be there, but I don't know.

Nadia: (15:42)

We're getting there.

Erin: (15:43)

Yeah.

Nadia: (15:46)

And on Dari Mulut ke Mulut you also have different kinds of posts, right? So you have the Monday email that goes out that's keeping people informed about the news, and then you have these dedicated feature posts that you send out. How did you decide on this editorial strategy of different types of posts for different types of readers? How does that work for you as a writer and for your audience?

Erin: (16:08)

This is going to sound like I'm probably sucking up a bit too much to Substack.

Nadia: (16:13)

Oh, please.

Erin: (16:15)

So the Monday one, that's usually really, really long and quite intensive. That takes me a full day to write, and it's still a bit fun, but it is very serious ... Because a lot of the stories, even with the last few months with the pandemic, prior to that a lot of the stories in the region are horrible atrocities. And that makes it really difficult to write about. So things like that, very serious in tone, and that's pulled out for ... That's a premium one for the paid subscribers. And when I was trying to work out how I wanted this to look exactly, it was right at that time that I think Hamish sent out a big email recommending the best way to do it for everybody, the scheduling, where it was something like one premium and then two free ones a week. And that's what I've been aiming for since, and that's been perfect, I think that's worked really well. With the pandemic, though, I'm trying to publish at least three times a week, and that's mostly just free, because it's so important.

Nadia: (17:28)

Yeah, I'd love to hear more about that, just because the pandemic's affecting a lot of people in different ways. I've noticed you've done more COVID related reporting now. Does it feel like it's just another hot issue that maybe has an extended period of coverage, or does it feel like you're actually having to think about things in a different sort of way?

Erin: (17:46)

That's interesting, because when it first started, southeast Asia was the first region outside of China to have known cases. So that began for us, I think, in January Thailand confirmed its first case, late January. And then the Philippines was the first death outside of China. So it's a beat that this region's been on for probably a few weeks sooner than New York, but it feels like a lot longer. And initially it seemed like it was just another big, big story and it would be something that I'd be covering for the next few months, but alongside the regular news that we get out of here. And then it very, very quickly just dominated everything. And I don't see it coming back from that for a few more months yet.

Erin: (18:43)

Which is interesting, because then you've also got some really important stories that are just being totally buried by this that is hard to ... I know it's out there, but you can't find it because the reporting isn't there, which is a bummer, but I understand. So that's part of the reason why I've started commissioning original pieces from other reporters in the region, particularly for areas that are under-reported completely. Because we do see a lot of areas that, they just aren't, there's either horrible media restrictions or they're just seen as too small, too insignificant, I guess, to be covering. Yeah, so I've started commissioning pieces around coronavirus in those sorts of areas to fill that gap.

Nadia: (19:39)

That's really interesting. I saw that you did one in, I think, Laos, is that right?

Erin: (19:43)

Yes, yeah, I've got another one from that same writer running today, which is amazing, because Laos is, alongside North Korea, one of the only two media black spots in Asia. Which is weird, because it's still got bigger press freedom ... Larger? I don't know. Stronger press freedoms than Vietnam, but still, that's what that reporter says. And it's just really, really hard to get a real idea of what this pandemic actually looks like out there.

Nadia: (20:21)

You call them media black spots in the sense that there just isn't enough coverage for the region?

Erin: (20:24)

Yeah, just nothing coming out of there. They've got, Laos is probably the hardest one to cover. Because there's Radio Free Asia, which has been there for a while, but there's also a bit of ... Some people don't really enjoy having Radio Free Asia speak for countries like Laos, given its history. But at the same time, it's one of the only ones there that can report on some of these huge stories. Laos is integral to China's dominance in the region, and if Radio Free Asia is the only one that's going to do it, or Voice of America, then that's just the way it has to be. Because there's no local media, or at least not large local media, I should say, rather.

Nadia: (21:14)

Do you think there are ways in which being an independent writer and an independent reporter can be an advantage in this sense? Because I know you said this correspondent is anonymous, which I don't know if that's for specific reasons or not, so without revealing the identity of this person or anything like that, is there an advantage to, "Okay, well, I know someone who lives in this region that's being under-reported, but I have a following, I have an audience, and we can directly pipe this in," instead of trying to go through these outlets that...

Erin: (21:45)

Yeah, very easy to sneak under the radar. Plus, it's hard for the big mastheads to take a punt on a country like Laos or an issue like coronavirus in Laos. But for me, I already know that my audience is interested. They've signed up specifically for news on countries like Laos. So for me it's easy to sneak under the radar and I know people are interested, so it's a no-brainer for me, I think.

Nadia: (22:19)

Yeah, that's really cool. Do you, because you are serving readers in a bunch of different countries, even if it is all the same region, do you find that readers are interested in stuff from different countries, or do they just want to hear from their own country?

Erin: (22:32)

That's an interesting question. I did a bit of a shout-out, well, not a shout-out, I don't know if that's the right way to put it. I sent an email around to premium subscribers last week or the week before, because I noticed that I hadn't sent a premium one, like members only one, for a few weeks, because it's all been coronavirus. And I said, "I want to keep reporting for the premium audience, so what is it that you're interested in? What do you want to be hearing about at the moment?" And it was really interesting that the array of people who responded, I think, is probably pretty representative of my audience. So it was a couple of Australians that have lived and worked in the region for a long time, a few young ASEAN nationals who have studied abroad and have since returned to the region or are still studying, and just a couple of friends, just be like, "Oh, hey, yeah, sounds cool."

Erin: (23:34)

And that was really interesting, because it was mostly just like, "I want to hear what's happening with human rights, I want to hear about, is there ..." I think we were seeing this around the world, but some not-so-great politicians using the pandemic as a cover to force through some more ... I don't know, some problem ... How do I put this? Some draconian laws, or exploiting this to stamp out and demonize dissidents, which we see in a couple of countries in the region a lot anyway. So this is an easy way to exploit that crisis. Or more about the bloc itself as a body. Which was interesting to me, there was nothing about, "What is it like for expats in Hanoi?" Or, "How do I get home from Singapore?" Or whatever. I really appreciate that my audience is very interested in the region, not in how the region affects them in their own country.

Erin: (24:56)

And that goes as well for readers that I know are ASEAN nationals. It's not, "How does Indonesia perform compared to Thailand?" Or whatever. It's very, "What is my country's place in this region and what does that look like overall?" I think that's very cool, I'm very grateful for that.

Nadia: (25:18)

Sort of an advantage of having this regional focus too, that allows you to zoom out and be a little bit more holistic in the stories that you talk about.

Erin: (25:25)

That's a good way to put it, yeah, definitely.

Nadia: (25:29)

You mentioned the responses you got as this microcosm of what you see on your list, which reminded me I haven't even asked you, how did you grow your list early on?

Erin: (25:39)

I know, it cracks me up because it's literally by word of mouth, and that's the name of the newsletter.

Nadia: (25:44)

Right, everything comes back to the title again.

Erin: (25:47)

When I first started, and I think I was still ... I don't know, I still think of myself as a bit of a baby journalist, but I was very much a baby journalist then. Less than two years in Jakarta, no idea what I was doing, sort of thing. So I didn't have all that much credibility then. So initially the list was just friends and friends of friends, I think, especially friends like Australian friends, who have studied or traveled or lived in the region. They were particularly interested, most other people weren't. But I think the biggest thing for me was the consistency, to be pumping it out continuously and just getting a bit better at it. Because it's not just getting better at getting it out in time. You just have to know your s**t a little bit better each time as well. And that was a tough thing. There is a lot of learning curves when you'll hit 11 different countries, all with incredible histories and incredible presence.

Erin: (26:52)

And once that started building credibility a little bit, it got pushed by a few people that were really, really helpful. So especially Alan and Richard from Splice Newsroom, which is a Singapore media. They do original reporting about media in the region, or help newsrooms in the region brand membership programs and that sort of thing. And I think having their stamp of approval really helped a lot in establishing that credibility. As well as a few of the think tankers and foreign corrs who have shared it on Twitter. Every time that happened there'd be 100 new people on it, which is good.

Nadia: (27:38)

Yes, always a great strategy.

Erin: (27:42)

Yeah.

Nadia: (27:44)

So you started in 2016, is that right?

Erin: (27:47)

Yes. Yeah.

Nadia: (27:48)

And then you went paid, or you added paid subscriptions about two years into that, which I think was around the time you also joined Substack.

Erin: (27:56)

Yeah.

Nadia: (27:58)

What made you decide to go ...

Erin: (28:00)

Well, this is weird, because I started, I hadn't heard of Substack until a very good friend of mine, who used to work for Coconuts Jakarta but has since moved back home to the US, and he started Indonesia Intelligencer with them, which is a paid subscription looking at Indonesia very, very in depth. And I hadn't heard of Substack, and he told me about, and I was like, "Oh, s**t, I'm doing that." And I just jumped straight over. And I've since taken over his job, so thank you, Aanant, twice. And I think it got to the point where I was doing so many and I was getting consistent and I was learning so much and I was working very, very hard that it became a bit of a ... I was like, do I really want to be working on this 20 hours a week for nothing? Apart from a bit of credibility when I pitch somewhere? So I think I came to Substack at the perfect time for leveling myself up.

Nadia: (29:07)

Did you find that there was maybe a trajectory of, you mentioned you started when you were super early in your writing, in your journalism career, and I guess there was some sort of mutual transference of credibility as you were writing more and having this newsletter, and then there is this point, it sounds like, where it was like you've gotten some measure of credibility early on, but then it's this next phase of, "Well, now if I'm putting 20 hours a week into this, then maybe there's something ..."

Erin: (29:38)

That's it.

Nadia: (29:38)

Performance.

Erin: (29:40)

Yeah, turning it into a part-time job as opposed to just something you do. Instead of a hobby, I guess.

Nadia: (29:50)

Right, yeah, it's just interesting to think about, there's this reputational or credibility benefit that comes, and then at some point it's like, "Okay, I get that, but I'm still putting a lot of time and work into this."

Erin: (30:03)

Yeah, this is like anti-advice, because I think this is where a few newsletters might go a bit wrong, where it's like there's ... And I love the advice that Substack gives about this, because you can't just be like, "I'm doing this and here's the paywall." No, you do have to establish that very quickly. And if you're someone like, I'm going to say his last name wrong, Matt Taibbi?

Nadia: (30:26)

Taibbi, yeah.

Erin: (30:27)

Taibbi. He's got his credibility built in. But if you're someone like me you've got to just hustle it out for a little bit longer than maybe you'd like to.

Nadia: (30:39)

Yeah, absolutely. I'm really glad to hear you say that, because that's not anti-advice, that's good advice.

Erin: (30:44)

Good.

Nadia: (30:47)

Because we see all sorts of people come to Substack, and some people have huge audiences elsewhere like I mentioned, of big Twitter followings or whatever, and then they come here. And this is just the natural next step, and they've already built that audience somewhere, and that audience, some portion of that audience is going to follow them to Substack.

Erin: (31:01)

Yeah.

Nadia: (31:02)

But then some people join Substack and are really just starting from scratch and building a list from literally zero. And the way that they need to think about growing their publication is just going to be different from Matt Taibbi or whatever.

Erin: (31:20)

Absolutely, yeah. And what I really like about Substack is that it's not just like, "Okay, here's your platform, go have fun now." I feel like Hamish is in my inbox more than anyone. And you now.

Nadia: (31:31)

Mine too.

Erin: (31:35)

It's not just about ... I don't know, I really, really appreciate that there's so much helpful advice and ideas about how you can build it and work out what it is exactly that you want from it. Because it'd be so easy to just be like, "Okay, this is the platform to use." But I really appreciate that, it's definitely helped me a lot.

Nadia: (31:57)

Cool, I'm glad to hear that. You're now also being a part of it.

Erin: (32:01)

Yes, I've made it. But I think that's actually ... More unsolicited advice, actually read the emails from Substack. That helps a lot.

Nadia: (32:12)

Yes, I will support that as an occasional writer of those emails. Please read our emails, they're important.

Erin: (32:17)

And the threads, threads are amazing. For one, it's incredible to read what all these different people are doing with their newsletters. Some of them are so obscure and amazing, so much helpful advice from a lot of people that have been in the same position.

Nadia: (32:33)

Yeah, it's funny, after having conversations with writers we start to hear ... When you said “be consistent” I smiled to myself, because it's something that I've heard a lot of people say, and I feel like it's really an intangible thing, where someone's trying to grow their list and they're like, "What, just keep writing? That's not the answer." But it's like, no, that actually is a huge part of the answer. And it's funny that so many different people arrive on that in their own separate ways, regardless of what they're writing about. It is a really big thing.

Erin: (32:59)

Yeah.

Nadia: (33:00)

Yeah, it's funny, I actually just did a thread this morning, today or something like that, and I saw two folks I know, that they each write newsletters about watches, like timekeeping watches. And they found each other on the thread and I was like, "Oh, yay."

Erin: (33:14)

That's awesome, bringing people together, yeah.

Nadia: (33:17)

Yeah. So people read about all sorts of things, which is great.

Erin: (33:19)

Yeah. It's so cool.

Nadia: (33:21)

How did you decide, you were talking about paywall stuff, so how do you decide which of your posts you're going to make free and which ones are going to be paid? Where the value lies? Or did you experiment with different things before?

Erin: (33:32)

Yeah, and I'm lucky, I've got a very smart, angry friend who's a businesswoman. So she was really like, "This is what you've got to do." So thank God for her.

Nadia: (33:43)

Fantastic. We all need a friend like that.

Erin: (33:47)

Exactly. And it was very clear to me that the ... I think I had to work out what my base was, what my audience is. And the people that pay, overwhelmingly, are people that work somehow in the southeast Asia area. So that's either people that work at think tanks or academics or risk analysts or whatever. They're the ones that pay, so it made sense once I had talked it out with my pal that the really in-depth, long-ass one on Monday, which goes into every big story of every country, would be the one that's actually ... I shouldn't say actually valuable, but the one that people will pay for. And then the side ones are more just stuff that I'm really interested in for one day. So that's just how I broke it down.

Nadia: (34:44)

I'd love to hear you talk a little bit more about the side projects. You did this spinoff newsletter, Ayolah, that ...

Erin: (34:52)

Yeah, Ayolah.

Nadia: (34:54)

My pronunciation here, but just to cover the Indonesian elections, and then it sounded like the elections happened and then you were like, "I'm going to keep this spinoff project to continue to cover other elections," which I thought was cool. We don't have a ton of examples, but I love finding examples of writers that are doing spinoff newsletters. So yes, please inspire other people to do it.

Erin: (35:16)

Yeah. Well, I liked it, and then the Indonesian election happened, and then that was it. I was like, "Okay, that's the last election for a while in the region." So that's very much on hiatus at the moment. Because last year was a big year. Indonesian election happened around the same time as the Philippine midterms, which is huge, and the Thai election, which was very complicated and messy in a different way. So between the three of them, those elections were taking up way too much space in the regular newsletter. So it just made a lot more sense to just pull it out and do it somewhere else. Because there'd be days, weeks where it'd be like 3,000 words, which is double what I aim for, just because so much happened in Indonesia in the last four days on the election. I'm like, "Oh, God." So pulling it out made a lot more sense.

Erin: (36:11)

And it's something I want to continue doing, but I don't know. It's going to be weird, we don't really have ... We've got two elections this year, one's definitely happening, one I'm not sure about in Myanmar, and that'll definitely be coming back.

Nadia: (36:27)

I see, interesting.

Erin: (36:28)

But that one's totally free as well. I don't think that's worth ... I see that more as feeding people towards the main one rather than a stand-alone side project, if that makes sense.

Nadia: (36:42)

Right.

Erin: (36:42)

Yeah.

Nadia: (36:43)

Yeah, totally. We have another writer, Walt Hickey, who does, he has his main newsletter, which is a data lens on the news, and then he does a whole bunch of different side projects and is very vocal about this being a really great thing.

Erin: (36:56)

Yeah.

Nadia: (36:56)

Which I think is a great thing. And he talks about it in a similar way, of these side projects feed in mutual directions back to my main list. And the nice thing about having a main list and then spinning off with a side project is, you automatically have an audience of this side project.

Erin: (37:12)

Yeah. Absolutely. Oh, all right, I'm going to search him out.

Nadia: (37:17)

Oh yeah, we actually have a post about it, I'll send it to you.

Erin: (37:18)

Oh great, cheers.

Nadia: (37:21)

Where he talks about this. Oh, no worries. And how did you decide on pricing for Dari Mulut ke Mulut? We have a minimum price, but then I'm sure for pricing for different markets that aren't necessarily, they might just have a different scale. Yeah, how did you work that out?

Erin: (37:42)

No, that's a good point. I started off with the ... I'm not sure if it's still the default, but I started with the $5, $50 thing. And then that same angry, this woman friend, told me to put it to $7 and $70. But that seemed crazy to me so I just split the difference and went $6, $60.

Nadia: (38:00)

You really split the difference.

Erin: (38:05)

But I agree, I think pricing people out of the market's a bummer anyway. It's especially so in southeast Asia, where I don't want southeast Asian people to not be able to read about their own region. So I've left it at $6, but any national from an ASEAN country or Timor-Leste under 30 gets a free subscription. So that just worked out easily for me.

Nadia: (38:35)

And I saw student subscriptions as well.

Erin: (38:39)

Yeah, and that's also, I think somebody at ... It's always funny, I can always tell when somebody at a university's mentioned it because I'll just get 40 requests all within an hour. I'm like, "Oh, great, Hong Kong University's given me a shout-out, cheers."

Nadia: (38:56)

Do you know how they're giving you ... Is it they're sharing it somewhere in a publication?

Erin: (39:01)

I don't know. Sometimes I ask, because some people are ... I don't know, sometimes students seem a bit scared, like, "Hello, I am so-and-so and I study this." I'm like, "Oh, thanks." And sometimes they're a bit more chatty and I'm like, "Hey, where did you find out about this?" And they'll just tell me. And usually it's just been shouted out in a lecture or something like that, Facebook groups.

Nadia: (39:24)

That's great, again, speaks to the power of word of mouth.

Erin: (39:26)

Yeah, totally.

Nadia: (39:29)

So you've been writing the newsletter for a long time, well before they were cool, which I think is awesome. Since newsletters have become this more of a trend and more of a thing that people understand in the past year or two, how have you seen things change? Did you find that people thought or talked about your newsletter differently early on? And has it changed your writing style at all as expectations have changed?

Erin: (39:54)

Yeah, I think people have stopped calling it an email blog now, which is cool. Yeah, and I think there's a lot more ... I talk about this all the time. Isn't it so weird that email is cool now? Do you remember five years ago getting an email and you're like, "What is this?"

Nadia: (40:11)

People thought email was dead, they're always saying it's dead, but right now it's definitely not dead.

Erin: (40:15)

No, it lives again. Yeah, it's interesting to see that people are so willing to pay for an email newsletter. I didn't really think that was a thing, but yeah. I don't know.

Nadia: (40:34)

Because you did this in 2018, which was, I think, basically when Substack started.

Erin: (40:40)

Yeah.

Nadia: (40:41)

And it really wasn't a thing. Even now it's often difficult to explain to people that this is a thing that you pay for it. So you really saw it at the early days, I think, when people weren't ...

Erin: (40:51)

Yeah, there's an Australian that lives in London, I can't remember her name, but she sent out a newsletter for years and years, and I think she's old school, am I allowed to say MailChimp on the podcast? Old school MailChimp one.

Nadia: (41:04)

Yes, you can say anything you want to.

Erin: (41:07)

So I was a bit like ... And I think initially mine was modeled on hers, where it was very like, "These are some interesting links I read this week." And that's how it started. But I don't know. There's just so much room for creativity on it that I think didn't exist a few years ago, or some of the ideas just never existed. And this thing now with popping in audio as well, that's crazy to me. You're developing so quickly.

Nadia: (41:39)

Yeah, hope so. Yeah, it is funny, I feel like links were the gateway drug for a lot of newsletter writers, where ... I have a newsletter that I don't write nearly as frequently as yours, but I think early on I also thought of it as, this is just where I share, I dump a couple links when I've written something or whatever, and then I think at some point there's this mental transition that happens where you're like, "Oh, I have this platform and people are opening my email." And then start talking a little bit more because you're on stage, you might as well be saying things. And then it develops into this narrative style.

Erin: (42:16)

Yeah, that's exactly it, yeah.

Nadia: (42:19)

Yeah. It's really cool. Well, cool. Thank you for joining and chatting with me. Is there anything else that you want to mention here for people that are just starting to write on Substack?

Erin: (42:30)

Oh, I don't know, that's a good question. Because I think the best thing that I did was sign up to just about every free list on Substack I could find. A lot of the political reporting on there is American, which is, unless you're American, probably too much American news. But signing up and reading as many other newsletters as I could was probably one of the most helpful things I did in addition to reading the Bangkok Post every day and all that. Learning to do it by watching other people do it has been really, really valuable. And I think not only is it interesting and you learn so much interesting stuff reading other people's, but it gives you a bit of inspiration and a bit of, some ideas about how you can use your own, develop your own, which I find really valuable. I still do it. I've been doing this for four years and I still read everybody's to see what's ...

Nadia: (43:37)

That's impressive. Lot more to keep up with now.

Erin: (43:41)

Oh my gosh, yes. It's interesting, I feel like they're getting longer as well. The length of an email, I swear, used to be like 700 words max. And now I sit there reading Hell World for an hour or two. I'm like ... Huge.

Nadia: (43:55)

It's true, I think it's that stage mentality again, we're like, "Oh, I'm still holding the mic, so better keep going longer and longer." People keep reading it.

Erin: (44:04)

Exactly, exactly. Yeah.

Nadia: (44:08)

Cool. Thank you. And where should people find you if they want to check out your work?

Erin: (44:11)

Darimulut.substack.com, which ... I almost regret giving it that name because it's D-A-R-I-M-U-L-U-T.substack. And there I think you can find links to everything else I do as well.

Nadia: (44:27)

Yes, we'll link to it in the show notes.

Erin: (44:30)

Brilliant.

Nadia: (44:31)

Awesome. Thanks, Erin.

Erin: (44:32)

Thank you so much.

Get on the email list at on.substack.com

We spoke with Nikhil Krishnan of Out of Pocket, a newsletter that’s tackling healthcare with an entertaining and approachable voice.

While working on the healthcare research team at CB Insights, Nikhil started an industry newsletter that grew to 90,000 people. He then worked at a clinical trial company and now writes about healthcare full-time on his own newsletter, which he started earlier this year.

We spoke to Nikhil about why he’s trying to make healthcare more interesting, his early paid experiments, and how to grow a thoughtful reader community, one person at a time.

Links

* Out of Pocket, Nikhil’s newsletter

* Get Real, Nikhil’s online community experiment

* Matt Levine’s daily finance newsletter, Money Stuff

* Nikhil on Twitter: @nikillinit

Highlights

* (04:31) On making healthcare feel accessible to more readers and how to value expertise

* (10:39) Being a writer vs. being a practitioner

* (19:15) How he grew his list on Instagram, Twitter, Slack, and LinkedIn

* (29:56) Experimenting with different paid offerings for readers

* (37:27) Building a community that maintains high-quality conversations

* (43:03) Subscription tiers and price differentiation

On figuring out which experts to trust:

I think the key is really finding people who are flexible experts. Like people who have studied their field for a long time, but also still remain default skeptical of their field. And once you find those people, really attaching yourself to them, I think is really important. I try to use those people to spitball thoughts off of pretty frequently.

On writing about healthcare:

[Matt Levine’s] newsletter is literally one of the funniest things I've ever read. He's so masterful and I don't care about finance, just to be clear, but he makes me care about finance, because it's so good, funny, and well written. And I'm thinking to myself like, "If finance can do this, healthcare can do this."

Transcript

Nadia: (00:23)

You write Out of Pocket, which has one of my favorite one-line descriptions, which is “healthcare, but funny.” And you have this sort of elaboration that US healthcare is a joke, and it may as well get funny.

Nikhil: (00:35)

Yeah, exactly. I think people in the US probably empathize with that. I try to keep it as short and punchy as possible.

Nadia: (00:44)

Yeah, I was thinking maybe people outside of the US don't find healthcare funny, but if you're in the US, you immediately understand the appeal of this newsletter.

Nikhil: (00:51)

I think it's one of those things where in the US, it's gotten so absurd that it's now funny. You know how when movies are so bad that they're good? But if you're watching from the outside, you're like, "What is going on?"

Nadia: (01:05)

Exactly. Or from the inside.

Nikhil: (01:06)

Right.

Nadia: (01:06)

So you started this pretty recently, just this year and it seems like the response has been great so far. I know you have a long history of doing healthcare research previously. So we'd love to hear a little bit about how you got here and why you ended up starting a newsletter about healthcare.

Nikhil: (01:21)

Yeah, definitely. So for some background, after college, I went to a company called CB Insights for about four and a half years. For those people who don't know, CB Insights basically tracks tech trends, just generally starting with private markets and kind of data happening in the startup universe and then expanded into kind of just tech in general.

Nikhil: (01:42)

One part of the CB Insights kind of business is the research team, which I was a part of and helped to build out and more specifically helped build out our healthcare research team. So I was doing that specifically for about three years or so. Part of I guess our growth strategy at CB Insights sites was to create these newsletters using the data that we had and put interesting things together. And so when we were building out the healthcare research side of things, one of the things I had to do was basically create our healthcare specific newsletter. And I was trying to think how I could make the newsletter different.

Nikhil: (02:20)

We had some data, which was interesting, but there were a lot of healthcare newsletters that had data in it. So I figured what I could do better than other people in the kind of health care newsletter landscape was be funny, which is pretty low bar and health care. So I was like, "I could definitely be funnier than these people." I started to kind of inject humor into the newsletter and that was pretty on brand for the rest of the CB Insights newsletter. It was kind of this snarky, humor-filled kind of content.

Nikhil: (02:52)

And we realized pretty quickly that it filled I think a really big niche for people. I think generally people are looking for tools and content, etc in the business world the same way they consume it in their regular lives and having a funny industry-specific newsletter sort of filled into that.

Nikhil: (03:10)

So anyway, I wrote that newsletter and I got to about 90,000 people by the time I had left. And after that, went to a company called TrialSpark where I was on the partnerships and business development team, basically creating new business lines and types of partnerships. And it's a clinical trial startup for anyone who's curious. And then yeah, about two and a half months ago or so, decided to leave to pursue Out of Pocket full-time.

Nikhil: (03:39)

I'm actually doing two newsletters, funny enough. One is sort of a side project called Get Real, which I'm happy to talk about later, but the main one I'm working on is Out of Pocket. So I saw the need for kind of funny, approachable, digestible healthcare research. I think a lot of people... I think it's really exacerbated now during kind of the COVID endemic that there really aren't that many good approachable sources of information for people and we're really seeing the divide of "healthcare experts" and then "healthcare novices".

Nikhil: (04:13)

And I think there isn't a good way to bridge people from knowing nothing about healthcare to learning about healthcare, it's a very uphill battle and I want Out of Pocket to kind of be an easier way for people to get involved in healthcare and then level themselves out. That's the long spiel of my life.

Nadia: (04:31)

I love it. It's funny. It feels like we've seen on the Substack, there are all these sort of drier industries like... Well, I think they're dry. Like finance and trading, healthcare in your case, venture capital. And so they're sort of attracting these meme makers. It's always just sort of something dry but then also made funny and entertaining and approachable.

Nadia: (04:59)

For me, coming from the world of open-source software, there were people that were developers on the ground and then there were also people like Tim O'Reilly, who were sort of translating what was happening there to a broader audience. Do you feel like your audience attracts mostly healthcare nerds and insiders, or is it people that are interested in understanding healthcare? Do you have to be a healthcare nerd to get the jokes?

Nikhil: (05:22)

What I try to do with the newsletters is make it understandable for average people regardless of their healthcare knowledge or experience, but I do like to insert some deep-cut references for the people who are pros. I tried to kind of bridge both worlds. I think the other reality is, most people in healthcare are usually experts in their own domain within healthcare. Healthcare is a lot of different industries: it's pharma, it's hospitals, it's insurance, etc. I think for a lot of people, they might know their own specific domain really well but are still novices when it comes to the rest of healthcare.

Nikhil: (06:02)

The goal for me is to make sure that I was approachable as possible for anybody. And I try to do as best of a job as I can for giving all the context you need within kind of the realm of one given newsletter. So, try to explain all the acronyms that are relevant, provide one-mind contextual sentences that are helpful about other par…

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com

We spoke with Nikhil Krishnan of Out of Pocket, a newsletter that’s tackling healthcare with an entertaining and approachable voice.

While working on the healthcare research team at CB Insights, Nikhil started an industry newsletter that grew to 90,000 people. He then worked at a clinical trial company and now writes about healthcare full-time on his own newsletter, which he started earlier this year.

We spoke to Nikhil about why he’s trying to make healthcare more interesting, his early paid experiments, and how to grow a thoughtful reader community, one person at a time.

Links

Out of Pocket, Nikhil’s newsletter

Get Real, Nikhil’s online community experiment

Matt Levine’s daily finance newsletter, Money Stuff

Nikhil on Twitter: @nikillinit

Highlights

(04:31) On making healthcare feel accessible to more readers and how to value expertise

(10:39) Being a writer vs. being a practitioner

(19:15) How he grew his list on Instagram, Twitter, Slack, and LinkedIn

(29:56) Experimenting with different paid offerings for readers

(37:27) Building a community that maintains high-quality conversations

(43:03) Subscription tiers and price differentiation

On figuring out which experts to trust:

I think the key is really finding people who are flexible experts. Like people who have studied their field for a long time, but also still remain default skeptical of their field. And once you find those people, really attaching yourself to them, I think is really important. I try to use those people to spitball thoughts off of pretty frequently.

On writing about healthcare:

[Matt Levine’s] newsletter is literally one of the funniest things I've ever read. He's so masterful and I don't care about finance, just to be clear, but he makes me care about finance, because it's so good, funny, and well written. And I'm thinking to myself like, "If finance can do this, healthcare can do this."

Transcript

Nadia: (00:23)

You write Out of Pocket, which has one of my favorite one-line descriptions, which is “healthcare, but funny.” And you have this sort of elaboration that US healthcare is a joke, and it may as well get funny.

Nikhil: (00:35)

Yeah, exactly. I think people in the US probably empathize with that. I try to keep it as short and punchy as possible.

Nadia: (00:44)

Yeah, I was thinking maybe people outside of the US don't find healthcare funny, but if you're in the US, you immediately understand the appeal of this newsletter.

Nikhil: (00:51)

I think it's one of those things where in the US, it's gotten so absurd that it's now funny. You know how when movies are so bad that they're good? But if you're watching from the outside, you're like, "What is going on?"

Nadia: (01:05)

Exactly. Or from the inside.

Nikhil: (01:06)

Right.

Nadia: (01:06)

So you started this pretty recently, just this year and it seems like the response has been great so far. I know you have a long history of doing healthcare research previously. So we'd love to hear a little bit about how you got here and why you ended up starting a newsletter about healthcare.

Nikhil: (01:21)

Yeah, definitely. So for some background, after college, I went to a company called CB Insights for about four and a half years. For those people who don't know, CB Insights basically tracks tech trends, just generally starting with private markets and kind of data happening in the startup universe and then expanded into kind of just tech in general.

Nikhil: (01:42)

One part of the CB Insights kind of business is the research team, which I was a part of and helped to build out and more specifically helped build out our healthcare research team. So I was doing that specifically for about three years or so. Part of I guess our growth strategy at CB Insights sites was to create these newsletters using the data that we had and put interesting things together. And so when we were building out the healthcare research side of things, one of the things I had to do was basically create our healthcare specific newsletter. And I was trying to think how I could make the newsletter different.

Nikhil: (02:20)

We had some data, which was interesting, but there were a lot of healthcare newsletters that had data in it. So I figured what I could do better than other people in the kind of health care newsletter landscape was be funny, which is pretty low bar and health care. So I was like, "I could definitely be funnier than these people." I started to kind of inject humor into the newsletter and that was pretty on brand for the rest of the CB Insights newsletter. It was kind of this snarky, humor-filled kind of content.

Nikhil: (02:52)

And we realized pretty quickly that it filled I think a really big niche for people. I think generally people are looking for tools and content, etc in the business world the same way they consume it in their regular lives and having a funny industry-specific newsletter sort of filled into that.

Nikhil: (03:10)

So anyway, I wrote that newsletter and I got to about 90,000 people by the time I had left. And after that, went to a company called TrialSpark where I was on the partnerships and business development team, basically creating new business lines and types of partnerships. And it's a clinical trial startup for anyone who's curious. And then yeah, about two and a half months ago or so, decided to leave to pursue Out of Pocket full-time.

Nikhil: (03:39)

I'm actually doing two newsletters, funny enough. One is sort of a side project called Get Real, which I'm happy to talk about later, but the main one I'm working on is Out of Pocket. So I saw the need for kind of funny, approachable, digestible healthcare research. I think a lot of people... I think it's really exacerbated now during kind of the COVID endemic that there really aren't that many good approachable sources of information for people and we're really seeing the divide of "healthcare experts" and then "healthcare novices".

Nikhil: (04:13)

And I think there isn't a good way to bridge people from knowing nothing about healthcare to learning about healthcare, it's a very uphill battle and I want Out of Pocket to kind of be an easier way for people to get involved in healthcare and then level themselves out. That's the long spiel of my life.

Nadia: (04:31)

I love it. It's funny. It feels like we've seen on the Substack, there are all these sort of drier industries like... Well, I think they're dry. Like finance and trading, healthcare in your case, venture capital. And so they're sort of attracting these meme makers. It's always just sort of something dry but then also made funny and entertaining and approachable.

Nadia: (04:59)

For me, coming from the world of open-source software, there were people that were developers on the ground and then there were also people like Tim O'Reilly, who were sort of translating what was happening there to a broader audience. Do you feel like your audience attracts mostly healthcare nerds and insiders, or is it people that are interested in understanding healthcare? Do you have to be a healthcare nerd to get the jokes?

Nikhil: (05:22)

What I try to do with the newsletters is make it understandable for average people regardless of their healthcare knowledge or experience, but I do like to insert some deep-cut references for the people who are pros. I tried to kind of bridge both worlds. I think the other reality is, most people in healthcare are usually experts in their own domain within healthcare. Healthcare is a lot of different industries: it's pharma, it's hospitals, it's insurance, etc. I think for a lot of people, they might know their own specific domain really well but are still novices when it comes to the rest of healthcare.

Nikhil: (06:02)

The goal for me is to make sure that I was approachable as possible for anybody. And I try to do as best of a job as I can for giving all the context you need within kind of the realm of one given newsletter. So, try to explain all the acronyms that are relevant, provide one-mind contextual sentences that are helpful about other parts of the industry. But the idea is that every newsletter should theoretically stand on its own and you should be able to read it as kind of a lay person. What I'll probably end up doing as the newsletter develops is having more backlinking to sort of primer style posts. So if you're confused about something, you can kind of backlink your way into the stuff to give you context.

Nadia: (06:48)

Can you talk a little bit more about this expertise issue of... I think this is especially true in healthcare where there's this fear, especially for people that aren't necessarily familiar with healthcare, they're not exactly sure who to trust, and I think there's maybe some especially tension with this and the cross over to tech where at least my experience of tech being that a lot of people emphasize an amateur point of view and saying, "You don't have to be this credential expert in order to speak authoritatively about what's happening." But I think there's a fear for people that are consuming that information of like, "What if I'm trusting the wrong person?" And like, "I don't have the context to necessarily understand which thing is good and which thing is not." From your position, how would you counsel I guess, a reader to think about that? And then also from your position, how do you balance the things that you know about versus the things you don't know about?

Nikhil: (07:43)

Yeah, totally. I think healthcare field is probably more acutely than any other field because it's very heavily kind of credentialed as a whole. I get it. Most physicians are spending decades of their lives to become experts in their field and to have someone who's kind of armchair epidemiology stating things when they've learned it for two weeks, you can probably understand why someone who studied this for 10 years might be a little peeved or kind of like skeptical. At the same time, I think some of the most interesting observations have come from people who are outside of the healthcare industry, even if there's like a higher noise-to-signal ratio.

Nikhil: (08:29)

I think the problem is that the two sides have acted very antagonistic towards each other as opposed to hearing each other's arguments and kind of finding interesting middle ground. I think there's still a lot of room there. So to answer your question a little bit more specifically about if you're a reader and you're thinking about healthcare, what in healthcare information to consume and digest, I think for one, there are obviously credible and less credible sources. And I think part of what I've been trying to do is follow people where networks of people I find credible also find those people credible.

Nikhil: (09:10)

If there are people who I've seen consistently seem to have really interesting thoughts historically and have trended towards correct, and then they endorse other people or their work, then I view it with a higher level of credibility. So it's a little bit more about focusing on the people specifically.

Nikhil: (09:32)

And then, for me, personally, in terms of things I know and don't know, I really try to try my best to build my own base knowledge first and then consult with people who I think are experts in their given field on where they think improvements can be made. I try and poke around the edges a little bit based on what I know is kind of like a novice in a lot of these areas and see how they respond. But I think the key is really finding people who are flexible experts. Like people who have studied their field for a long time, but also still remain default skeptical of their field. And once you find those people, really attaching yourself to them, I think is really important. I try to use those people to spitball thoughts off of pretty frequently.

Nadia: (10:19)

I really like that. It sounds like there's one aspect of it that's about using people you trust almost as credentials. And then, how to find those people sounds like part of it is just looking for people who are inherently skeptical, but also well-read and understand what they're doing.

Nikhil: (10:37)

Yeah, exactly.

Nadia: (10:39)

Do you find that you're in a different position to understand this kind of stuff? Because you're sort of looking more broadly at research and overall trends as opposed to being a specific practitioner, for better or for worse?

Nikhil: (10:51)

Yeah. I think there are pros and cons to the place where I sit. I think for one, I think I understand the worlds of healthcare and tech, a little bit better than anyone who sort of siloed in each of their specific domains. And then two, one thing that I really appreciated about my time at CB Insights is that actually when I started, I was covering healthcare but I was also covering consumer packaged goods, construction, agriculture and autonomous vehicles, which is mile wide, half an inch view on any of these. What was really, I guess nice about that is that you can actually see interesting trends across industries and do better compare and contrast of why different things happened when they did.

Nikhil: (11:40)

So for example, if you look at autonomous cars and you see the relationship between kind of like OEMs, manufacturers, etc, and you look at Pharma and try to understand what the difference is between the manufacturers and supply chains, you can see really super different dynamics at play, because of how patents work, of how consolidated the supply chain is, how specialized it is, etc. So it was nice actually seeing a lot of industries concurrently because it became easier, it became more interesting to kind of view them in parallel with each other.

Nikhil: (12:16)

I don't view that as very differently than when I'm viewing different parts of healthcare itself. So even looking within healthcare to see how health insurance works, versus how maybe auto insurance works, for example. They're very different dynamics. Health insurance is way more proactive in terms of trying to deliver care to patients versus auto truly access, catastrophe insurance.

Nikhil: (12:46)

I think being able to kind of sit at a bird's eye view makes that really fun and interesting, but simultaneously, there's going to be a lot of frontline really nitty gritty stuff that I'm going to miss out on. One piece of advice a mentor sort of gave me which I think was really useful was to try and alternate your career between really macro and then really micro viewpoints. And so at CB insights I was obviously sitting in a more macro stage, and then at that TrialSpark, it was working on really nitty gritty problems and really being on the front lines of things. And now I'm kind of oscillating back to the macro side. And so both gives you kind of like a industry lens on how your industry is changing, but then you can see on the ground, how does that actually impact the day to day operations or something. That's-

Nadia: (13:36)

I really love that. There's sort of a parallel there to the blogging versus building thing that I've also heard of. Sometimes it's really good to be zooming out and thinking about stuff and sometimes it's really good to be on the ground and they inform each other. I found this for people doing any sort of independent research or writing really deeply about a topic. It's so important to get both those things and a lot of people don't necessarily get the luxury of being able to do both.

Nikhil: (14:00)

Yeah. A hundred percent. I think being forced to write for a long time really made me realize actually how difficult the process of crystallizing your thoughts really is. And then, also feeling confident enough in the stuff you write to put it out in the public sphere, knowing that there's a high chance you'll probably get roasted over something you got wrong, which is just like reality of putting stuff in public but being confident enough in yourself to put that stuff out is really important.

Nadia: (14:29)

How does writing a newsletter at CB Insights compared to writing one on your own now? Are there tradeoffs here with editorial independence versus reach?

Nikhil: (14:40)

Yeah. I mean, there's definitely a lot of differences. One, when I was at CB Insights, my only job was to create the analysis. Now, we're doing my own. Writing is one portion of it, but other portions are like, how do I market this properly? How do I come up with the drip campaigns for people who are... There's a lot of logistics stuff in the back end. And then also, thinking about product roadmap is very different. Because obviously at CB Insights, we had an entire product team and the CEO is obviously very... Had his own vision for the product and the target customer was Fortune 500 and the goal was to sell more of the CB Insights data product. So, obviously very different motivations.

Nikhil: (15:26)

On being on my own, one had to think about different monetization channels. And then therefore, what does the product roadmap look like for a different channel? That's definitely different. And then editorial independence wise, there's obviously writing on your own, you definitely can write as much as you want. One thing I will say that I miss is... When I was at CB Insights, two things that were really helpful were one having really good editors. I can't stress enough how much having good editors really leveled me up as a writer and an analyst, because it forced me to basically distill my thoughts into things that people who are not healthcare people could understand. And that was really important.

Nikhil: (16:13)

Obviously, there's also the copy editing stuff, which I'm awful at, which, as anyone who's on these newsletters has probably seen at this point. And then the second thing was having co-workers to balance ideas off of was really useful. And obviously, being a solo writer, that poses its own challenges. And it's important, I think to create your own networks to bounce ideas off of other people as you're writing them. That was another I guess, struggle of going solo.

Nadia: (16:43)

Can you talk a little more about that? Just about how... Does having the newsletter now, has it led to you finding people that you can talk to about this kind of stuff?

Nikhil: (16:54)

Oh, yeah. Definitely. I mean, not only will I say that... I think I've built a network in healthcare people that I feel like I can balance ideas off of pretty regularly to fact check myself as well as come up with new ideas, but the newsletter itself is actually drawn an interesting kind of cross-section of people in health care who are masters of domains in their own area and are very willing and happy to chat about any topic that they feel like they're experts in which is awesome, because one thing about healthcare especially and I'm sure this is the case in a lot of other "legacy industries" is there's all these just like layers to it, that I still to this day I'm learning exist.

Nikhil: (17:40)

You'll discover there's some random industry that sits between two healthcare players and actually, billions of dollars pass through it. I'm like, "Wow! I just never knew these people existed." Once they... A lot of people will reach out and be like, "Hey, I work at this company. We do X, Y, Z thing. We're the wholesaler to wholesalers." I'm like, "What? How is that even an industry?" And then, will kind of like lead me to the rabbit hole of either chatting with them pretty quickly or looking into it myself and just learning way more just because they made their presence known as part of the industry, a part of the chain that exists.

Nikhil: (18:23)

It's been great to kind of riff with these people who are kind of masters of their domain. The other thing I will say is also people who at least for now, opt into reading out of pocket are typically the kind of people who wants to be kind of flexible experts. And so the nice thing is that it sort of creates this self selection mechanism of people who sign up for the newsletter and then also are motivated enough to actually reach out and say, "Hey, I really like this. Here's a quick paragraph on things I'm interested in and we're building here. I think you might be interested." There's a higher likelihood that those people are the flexible experts I was talking about before. And so I'm always very happy to chat with them and understand how they're thinking about their field.

Nadia: (19:15)

How did you grow your list for Out of Pocket? How did these people find you initially?

Nikhil: (19:20)

Yeah. I mean, I will say that I think I sort of built a following on Twitter to begin with by again, sort of shitposting my way to glory on the healthcare side of things. Definitely the initial cohort was people who were following me on Twitter or LinkedIn or something like that. And then since then, I've basically been reaching out either cold to people in different industries. I started an Instagram. My first ever Instagram, I'm not on Instagram personally so this is a journey and a half for me, I really truly feel like a total Luddite when I'm trying to use Instagram, but trying my best there.

Nikhil: (20:02)

But yeah, a lot of cold outreach. I think I'm going to be doing a lot of interviews with some people who have their own followings too. And well, I have been also asking people to post it in different kind of healthcare specific Slack channels, etc. So, really just trying to find any area where there seems to be healthcare interested people who kind of want to level themselves up or are interested in following trends in healthcare, etc. The pandemic has obviously proven to be an interesting kind of environment to do this in, because I think there are a lot more people who are now interested in learning how healthcare works. And so I've been trying to ride that trend a little bit.

Nadia: (20:45)

Are there a lot of pockets that already have, since... I don't know anything about the world health care of people that already sort of clustering and talking about this in different forums, if you're sort of I guess, looking to borrow or siphon off parts of other people's audiences?

Nikhil: (20:58)

Yeah. I mean, there's definitely a lot of people... There are definitely a lot of healthcare channels where people are talking about things. Lots of healthcare Slack groups, lots of other newsletters that are just generally about health care. Lots of, just I guess, different audiences. I think I'm the only person who's specifically trying to use humor and memes and stuff as their differentiating factor.

Nikhil: (21:25)

Those definitely exist. I think that a lot of this is for... I don't know how many of these communication channels are specifically targeting people who are not healthcare experts who want to learn about healthcare. I think a lot of these channels target people who are already in the industry and the whole point of Out of Pocket is sort of to make it more accessible for people. I usually have to find some other channels or partner with people who are also just attracting people who want to learn more generally and maybe it's not healthcare specific, it's just, "Hey." These are ambitious autodidactic folks who want to learn more about how the world works, not necessarily about healthcare, but those are I think, also good audiences to kind of show my wares basically.

Nadia: (22:23)

Can you talk a little bit about writing about healthcare on Twitter versus Instagram, which sounds like it's a new format for you and then also on Substack of just... how do the means transfer on Instagram versus on newsletters? Do you prefer one over the other?

Nikhil: (22:38)

It's so fascinating to see how... I mean, this is more of my anecdotal experience. I don't know if this was true for everything or not, but the audiences are so different, I will say. I think part of it is just... And it makes sense. People are going to these different avenues for different reasons. If you've opted in to sign up for an email newsletter, there's way more flexibility into the amount that you can write for the newsletter, obviously.

Nikhil: (23:08)

I take liberty with that and I try to create emails that are long and kind of in-depth. Because the format sort of allows for that. And I want people also to forward it and share it with other people because they thought it was informative. Twitter, I think people want to just bite size pippy anecdotes or stories. They want just the interesting part of the entire newsletter, they don't necessarily want all the context that's associated with it. And then for Instagram, it's almost entirely visual. There just aren't... There's no text.

Nikhil: (23:45)

Even trying to use Instagram for the first time, it's so funny because I'm like, "Man, why can't I link my newsletter in this?" And then my friends are like, "Dude, you only get one link." I'm like, "Oh, okay. This is very different." I'm trying to figure out... I think it's funny because I think memes are the great lowest common denominator across all of them. People just like memes. And I also think that if you can have basically a meme summarize whatever your main point is, and it helps I think solidify the takeaways for a lot of people, but they work well across different platforms.

Nikhil: (24:23)

And then the last thing I will say is that my whole shtick in life is trying to blend my personal and professional worlds very closely together. I think I'd like to reduce the delta as much as possible from who I am as a professional to who I am as a person where I think a lot of people try to keep those worlds separate. And so I think me posting on LinkedIn as if I'm a individual who's again making trash memes on the internet makes me seem a little bit more humanizing and I am not kind of writing this LinkedIn poetry about things. I'm trying to just be who I am as a person on LinkedIn, which I think maybe is not normal for a lot of people. But yeah. Anyway, I think there's a lot of medium differences but I'd like my style and tonality and personality to kind of show up no matter where it is.

Nadia: (25:18)

I didn't realize you're also on LinkedIn. You've really hit every channel possible.

Nikhil: (25:22)

I'm trying. I'm trying out here.

Nadia: (25:26)

There are actually a number of Substack writers that have built their audiences on LinkedIn. And then are also building on Substack. And I guess for me, I didn't realize there was so much going on but it sounds like it's become more attractive as a platform for sharing things in the past couple of years. Am I crazy? Where did this come from?

Nikhil: (25:43)

I think a lot of industry people still use... I think a lot of people who are, who are deep in their industries still use LinkedIn a lot. I was talking to a friend once and we were talking... The conversation of default social networks came up and he said LinkedIn and he to this day still gets roasted over it. I don't think people would ever out word me in the middle out of this and I also think, candidly I think anecdotally there seems to be a bit of also an age gap and difference or also a role difference and gap.

Nikhil: (26:12)

If you're... I think primarily, in a lot of sales marketing roles, LinkedIn is really important. I think it really just depends on the channel you care about. I will say that, I found that LinkedIn is a... So two things. I think one, LinkedIn is a great place to shill your wares to coworkers that you used to work with who maybe you're not... You don't have personal... You're not connected with on personal social networks. And then the second thing is, I think LinkedIn has a way higher noise to signal ratio or quality of readers just generally. So it really depends on what your goal is as a writer.

Nikhil: (26:54)

I think if you just want to get eyeballs on your stuff, then LinkedIn is great for that. I think if you're trying to do more interesting things with your readership specifically, then I think it's a bit of a crapshoot to get people from LinkedIn.

Nadia: (27:13)

Actually, I wonder about something related, which is, did you feel like when you had a newsletter, you're writing at CB Insights that it could be, I guess, as much of a calling card for lack of a better term versus Out of Pocket in that both are technically these branded newsletters that are... It's not like it's your personal newsletter or anything, that you're just kind of writing about whatever you're thinking about. Like they have a very specific focus. But in one case, it feels like you're, I guess writing for a company versus something that you've spun up yourself. Do you feel like one attracts more people to you than the other?

Nikhil: (27:48)

Yeah. I mean, I think the CB Insights brand was really strong. And so that definitely helped open a lot of doors both in terms of getting new readership because it was very it easy to sort of be like, "Hey, you've seen the CB Insights newsletter? We're doing the same thing with healthcare." People understood then what they're kind of getting into versus Out of Pocket, which is sort of a new approach to it that I have to sell a little bit more. And then the other thing is there's a lot more cross posting on the CB Insights newsletters too.

Nikhil: (28:23)

If you're interested again, in general corporate strategy, and you're a healthcare person, then you're probably signed up for the main CB Insights newsletter, and we'll tell you about the healthcare one, and you're probably interested in that. So there are definitely benefits to that. I think writing as a person has, I really have to focus a little bit more on selling me the person as opposed to any brand that I'm associated with. And that's definitely harder, but it's also something that I've tried to do a little bit more deliberately through the course of my life, especially just writing on my own personal blog and trying to build up my Twitter followers and posting on LinkedIn and all that kind of stuff.

Nikhil: (29:08)

I want people to know that I do know what I'm talking about a little bit as an individual and so, there hopefully is some merit to me writing as a solo person. I'll also say I've also leaned very heavily on people who I think like deeply believe in the stuff that I'm doing and writing about and working on as an individual to be a lot of the early evangelists of stuff. Having that support from people is really helpful especially in the early days. That's one of the benefits of also writing as a person as opposed to a brand is, I'm really leveraging my relationships to kind of help with distribution.

Nadia: (29:56)

Makes sense. I'd love to talk about the paid Slack experiment that you announced recently, which I thought seemed cool. It sounds like it's available only to people that subscribed out of pocket and sort of building upon this list that you're creating. Why did you decide to go with a paid Slack as your first paid product experiment?

Nikhil: (30:14)

Yeah. For some context, I'm doing a paid private Slack for Out of Pocket members where you have to fill out a form, I'm vetting the people who are coming in, then charging per month and also having a very heavy hand in sort of helping a moderate both in terms of... Mostly in terms of discussion starters and kind of curating events and some homework for people to do, etc.

Nikhil: (30:41)

So, that's the first product. I think there's a few reasons why I went down this route. I think a lot of people on Substack, probably their default monetization path is, "Hey, let me monetize the Substack." And I totally get it. But for me, like I said, the goal here is to help people are healthcare curious, get more involved in healthcare. And I think by forcing people to pay for the Substack, that kind of goes against the general principle of trying to get newcomers into healthcare. I wanted to try some other monetization experiments before I went down that route.

Nikhil: (31:19)

The reason I decided to do a kind of paid Slack channel is one, I think there's still a gap to having... There's still a gap right now of a really small group of healthcare operators specifically, who are building things, want to share tactics and advice and also are really, really interested in not just kind of asking for favors from a Slack channel, but more building a real community and kind of actually being somewhat friends with each other. If you were to go to a city and someone in that Slack channel, actually lived there, would you hit them up? And trying to actually get that happening. So stuff like that.

Nikhil: (32:04)

I also think that having a curated group of people, and understanding their thoughts about the industry is really important for me to understand for in terms of future things I'd like to write. And also in the future, I'd hope to use this kind of vetted group of people to, I don't know, either put out surveys and get their general sentiment on things and really get a true understanding of what I think they're happening in the ground. I think there's still a lot of room to build good healthcare communities. And I think this Slack is sort of one step to that.

Nikhil: (32:43)

It's probably worth also just explaining a little bit about what I hope Out of Pocket is in the future and how the Slack kind of fits into that. I really would like Out of Pocket to essentially be the onboarding mechanism for people who are interested in getting involved in healthcare. And so understanding trends and what's going on in the industry is one part and that's where the newsletter fits in. But I'd like to actually help people learn from nothing to being an expert. And that can start with basically crash courses. Eventually going to a three day intensive to help understand exactly how this part of healthcare works, maybe it's clinical trials or how does health insurance reimbursement work.

Nikhil: (33:27)

So that's where you learn about a really specific slice of healthcare, the newsletters to help understand trends in the industry broadly. And then once you're sort of in the weeds of healthcare itself, how do you connect with other people who are also in the weeds of healthcare, and that's where the Slack channel fits in. That's kind of the overarching product thought process.

Nadia: (33:48)

You refer to sort of this being a way for people to... Out of Pocket, in general being a way for people to familiarize themselves with the world of healthcare. There's still some self selection, I guess, or is there, around... It's not just necessarily someone who has zero... It's just sort of a casual, like I would love to learn a bunch more. Are there people that are coming at it from maybe like an investor perspective or an analyst perspective where they kind of need to get up to speed with healthcare? Or are you aiming for an even more general audience than that?

Nikhil: (34:23)

I think it's a little both. I think it's... Even when I think especially for a lot of startups, and I've seen this across a lot of friends who have joined startups, a lot of them join these companies maybe from... They go from tech to a digital health startup or something. And there isn't a great onboarding process in a lot of cases to understand how their industry works normally, and then how the startup works differently and what pain points they're trying to address.

Nikhil: (34:48)

So I kind of think of this actually as like almost external bootcamp to understand how your industry works also. So it could be from an analyst side of things, it could be from an actual operator side of things. It's funny because I went to... I did a Wall Street financial modeling boot camp just kind of for s***s and giggles, maybe six months ago or so. And it was funny because people went around the room to introduce themselves and basically every single person who was there because their company paid for them to be there as part of their onboarding process, whether that was onboarding into a new team, or onboarding into like an investment bank or etc. And then they got to me and it was like, "Hey. Yeah, I'm just here just because..." And it made me realize that like, "Oh, there's a lot of people here," just because their company doesn't do their training internally. They do their training largely externally.

Nikhil: (35:44)

When I was at TrialSpark, and I joined, I really wanted to understand the nitty gritty parts of the process of how clinical trials worked. And there are a lot of courses that are either really cheap online and $50, but no real accountability into like, learning in and they're really dry and boring, or there's these two-week fully immersive $10,000 courses and it's like, that's also not what I needed. I sort of taught myself and asked a lot of questions with people at the company internally, but I think it would have been really useful if even before I had started working to do like a three day intensive to learn the process. I'd like Out of Pocket to eventually move there.

Nadia: (36:31)

Had you thought about doing video courses or some sort of educational content? It's just interesting. A discussion group is so different from that.

Nikhil: (36:40)

Yeah. I think that's eventually where I'll move. But the discussion group is more just because... And frankly, it's one because I think corporate budgets for education are just way lower now, given it's a pandemic. And two, I think the audience was self selected into the Out of Pocket's Slack/my general I guess friends and followers are usually more deep in healthcare. And so this seems like actually just an easier to lift to start with. But eventually I would like to go into this educational component to get people leveled up either through video courses, or maybe it is in person boot camps or something. But yeah, basically moving into that area.

Nadia: (37:27)

And so you had this like... You touched us a little bit, but you had an application process. It's capped at max 15 people, there's homework. It's like, the bar is high. And you make that really clear to people that are I guess, thinking about applying it. Like, this is something that they should take seriously. Is there's maybe some crossover here with Get Real, which you mentioned early on about your experiment to create more authentic connections? I'm assuming all this is sort of done to keep Slack conversations interesting because they sort of die, they often die after the initial launch and everyone being sort of excited. I think that fear keeps a lot of people including myself from starting to Slack. What are some of the things that you've learned either from Get Real or from doing this, of just how to keep conversations interesting and at a high bar?

Nikhil: (38:18)

Yeah, totally. And you sort of have, I think, seen the connection here, but get real has been my community building experiment on the side. And again, for context, if anyone's interested, I was going through my quarter life crisis three years ago, so I started this newsletter where I ask a question each week, I answer it and then I get other people's thoughts and post my three favorite answers the next week. And that's sort of the gist.

Nikhil: (38:46)

What I've learned about good communities, I guess it's they hinge on a few things. One, you need really active key members/moderators. There's always a few people that you need to be constantly kind of keeping the conversation up and engaging people, other people in the group. And it usually has to be more than one person. I would say it's one, two, maybe three people who are really, really active participants and group members to kind of normalize the idea of participating regularly. That's one thing.

Nikhil: (39:21)

Two, is you can't scale it very fast. I think this is a trap that most people fall into, especially when you're monetizing directly off the people who are in the community or whatever is you start a community, a few people join and you seem to have a really high-quality group, then you raise a seed round or a series A round and then you just put all that money into paid marketing or whatever, and just dramatically increase the size, but then the quality drops inevitably.

Nikhil: (39:53)

You have to be, I think, really deliberate about how you grow the community and I think it's very tempting to just grow very fast. But I've never once seen a community that grows fast that managed to keep the community feel. And then the third thing is, I think by requiring work from the members, people are more invested in the community itself. I think generally, the internet community is at least in V1, and maybe this is changing a little bit, but most internet communities, they try to lower the friction joining as much as possible to get as many members as they can, usually because they're volume-based communities.

Nikhil: (40:38)

I'm trying to actually increase the friction so that the people who join the community really are serious about it. And if you... It's a lot... It's going to be work. Like you said, there's some homework, there's as an application. If you are willing to jump through all of those hoops, then you're someone who probably cares enough about this and you will find other people who care enough about this that I think that will select for people that are wanting to be a part of a good community and then therefore will be better members of the community. I'm trying to increase friction and make it harder to be a part of this community, but make the reward, I guess more worthwhile.

Nadia: (41:19)

I like that. It makes sense with all the different places that you're writing about this stuff that... It's sort of like there's this drip filter of someone might just casually follow you on Twitter, and then they might be like, "Oh. I'll sign up for this newsletter." And they're like, "Oh, maybe I'll try out the Slack." And it's like... It's sort of cultish in a way of thinking something like level zero, level one, level two or something, of getting all the way up to like that, paying money to talk to you.

Nikhil: (41:48)

Yeah. For one, I promise it was not as engineered as you make it seem. It was just very random. And two, I'm totally cool with being friends with people for free. You don't have to pay to be my friend, but I think of it a little bit more. I think the tiering thing is right. I think the sense of... I want people to opt into whatever level they feel like they want to give the commitment to, which is why this is... There are different products that are targeted towards different levels of like, I don't know, healthcare experience and commitment.

Nikhil: (42:30)

So, if you're someone who is just healthcare curious, I don't want you to have to do a lot of work to be a part of... To get something out of this, out of Out of Pocket. There's a level that works for you too. But if you're someone who is really trying to meet people who are just as ambitious as they are in terms of stuff they're trying to build in healthcare or just as deeply knowledgeable, then there's something for you too. So I'm really trying to like create products for those different tiers of kind of expertise and interest.

Nadia: (43:03)

It feels like that's one of the most important shifts from, for lack of better terms, “volume-based” monetization versus “context-based” monetization, where I guess just think about advertising or this sort of core belief that you have to make money off everybody that's looking at your stuff. Whereas, I think one of the cool things that you can do by having these more filtered places is... It's fine if 90%, or 95, or whatever, most of your people are just completely reading all the free stuff and you make nothing off of them. And that's fine, because there's some smaller group that's willing to pay a lot more that sort of subsidizes it for everyone else.

Nikhil: (43:45)

Yeah. I think that's totally right. I think one interesting thing, for Get Real, I don't really treat that as much as a business right now. It's more of a side project, but I started a Patreon for it because obviously there are some costs associated with just even running it. But I went with a tipping based business model because I think one of the interesting things is people get different levels of utility out of any product or any, I think even any newsletter.

Nikhil: (44:15)

When you create... When you don't have tiers of subscription, I actually think that you kind of have a cut, like a loss. You either have a... listen man, I'm blanking on-

Nadia: (44:30)

Deadweight loss kind of-

Nikhil: (44:31)

Yeah, yeah. Deadweight loss. Thank you. I'm getting PTSD from Econ 101.

Nadia: (44:36)

Me too.

Nikhil: (44:37)

You have like a deadweight loss basically. People who actually probably would have been willing to pay more because they got more utility. And then you also lose a lot of people who probably were willing to pay less, but still get some value out of it. And the price point you picked is just a little bit outside of their range. And so I think that... I think having the tiering is really important because you want people to sort of stay in your universe, per se. And then pay the level that they care about or the level they get utility from to minimize that deadweight loss.

Nikhil: (45:09)

And I think if you just pick, one specific price point for one product, etc, then you're... I think you're doing yourself a disservice. So, yeah. I'm interested to hear how other writers have thought about different product tiering if they have, but that's sort of the way I've thought about it.

Nadia: (45:28)

It seems especially relevant for people where's someone who's paying might be paying... I guess they have access to a corporate sponsor or whatever. They could charge it to some sort of corporate expense account. And then you also probably have people that are just sort of casually interested and want to do it for themselves. So you're sort of catering to a lot of different budgets as well.

Nikhil: (45:51)

Yeah. I also think... One thing I've noticed, at least one thing I've noticed is that there are some people who are just like voyeurs for the most part who are just consuming content and maybe don't necessarily want to be a part of a community, etc, but when you start talking about topics that those people are specifically experts in, it's awesome to have them as part of the newsletter so that they can chime in.

Nikhil: (46:14)

And so the problem is when you, I don't know, maybe do like a weekly... When you do like a monthly recurring revenue business, there's some people that are not going to get as much value every month that they do, but you don't want to lose them because in the months where they are specifically experts in that area, then it's awesome to have them there. And they can chime in when they feel like it. And so I really like those people really on the edge who are on the fence about getting involved or not because I think when they do... When it is something relevant to them, their contributions are awesome. I wouldn't want to exclude them, if that makes sense?

Nadia: (46:57)

Yeah. How did you decide on your pricing for the Slack group? It's a good price. $20 a month?

Nikhil: (47:06)

I got to tell you, there is no science to this one. I have some people that are like, "Man, that's like really high. I spend this much per month on Netflix and this is double that." And then I have people on the other end being like, "Dude, you're charging too low. People are looking for this. Their willingness to spend is probably way higher." And I'm like, "Wow. I really, really don't know what the answer is." And so, I'm being totally honest with you, it's random. It's very random. It's what I feel like I would have paid if I wanted to join Slack that was valuable. And the pricing is probably going to change over time.

Nikhil: (47:48)

There's going to be probably different... Some people may be grandfathered in until this pricing, maybe they'll have to drop it or increase it. It's weird because it's kind of like the in between of what an individual willingness to pay would be like, which is a little higher than that and then it's probably way lower than what a corporation would pay. And so I'm curious to see what this kind of middle of the lane pricing looks like. It's an experiment. We'll see. We'll see how it goes.

Nadia: (48:20)

Yeah, I love that. I love that you're just sort of taking this very experimental approach to absolutely everything that you're doing. It feels like you're building this sort of mini media empire, but you're testing out all the different waters and seeing which things resonate, which is really cool.

Nikhil: (48:35)

My third or fourth newsletter was about experiments with too many confounding variables. And the irony is that I think... I don't know if I'm going to do that, but we'll see.

Nadia: (48:48)

If you had to point to like, I guess to get philosophical as we're wrapping up here, what would you say is sort of the center of that whole brand or empire, all the things you're trying like? Is it you as an individual and your reputation? Is it like a certain content format that you're sort of the bread and butter of everything?

Nikhil: (49:06)

I think it's a combination of the two. I think it's really just about me as a entity that sort of informalizes healthcare, using humor, using very everyday language, etc. I think that just the world of non-healthcare and healthcare has gotten so divergent that there have to be more channels to bring them together and make people who are not in healthcare understand how healthcare works, people in healthcare to be better about explaining what they're doing.

Nikhil: (49:38)

And I guess one of like one of the people who are doing that, and so this may be right now at least centers on a lot of the stuff I'm doing but I'd like you to expand past just me. I'd want more people to kind of get involved to be. Maybe it's people within the Out of Pocket community who are teaching other people about areas that they're experts in but doing it in a way that is sort of on the same kind of brand of accessible funny, informal like this is me teaching you as an individual if we were at a bar or getting a drink, rather than, "Hey, I'm giving you like a corporate pitch presentation about what we do."

Nikhil: (50:20)

So, yeah. The goal for Out of Pocket generally is just in formalizing healthcare a little bit, and I hope more people are interested in doing that.

Nadia: (50:33)

Great. It reminds me of talking to folks in the finance Twitter kind of world who say that there was a time when not many people were doing that and now it feels like a lot of people are doing it. So it seems like you are sort of at the beginning of that with healthcare.

Nikhil: (50:46)

I think it's really funny you mentioned that because finance in particular, I think, has this amazing army of this pseudo anonymous, hilarious, but very highly analytical and technical group of people. Even just whether it's on Instagram or Twitter, a lot of the fintech anonymous accounts, they're really smart and they're very funny. And actually, the inspiration for Out of Pocket came from Matt Levine.

Nikhil: (51:14)

And I think his newsletter is literally one of the funniest things I've ever read. And he's so masterful and I don't care about finance, just to be clear, but he makes me care about finance, because it's so good, funny, and well written. And I'm thinking to myself like, "If finance can do this, healthcare can do this." And so yeah, it's funny you mentioned finance, because that's exactly the trajectory I hope this takes.

Nadia: (51:40)

Me too. It's been really fun to watch so far.

Nikhil: (51:43)

Thanks.

Nadia: (51:44)

Thanks for joining in chatting. Where should people find you if they want to check out your work?

Nikhil: (51:49)

Yeah. You can come to the Out of Pocket Substack which is https://outofpocket.substack.com. I write about the things on my personal blog. It's https://nikhilkrishnan.com. And if you're interested in joining Get Real, it's https://getreal.club because you can do cool things with URLs now. And also on Twitter @nikillinit. That's basically where my most half-baked thoughts are. So happy to chat with anyone who's interested in learning more about healthcare.

Nadia: (52:21)

Awesome, thanks.

Nikhil: (52:22)

Thanks so much.

Get on the email list at on.substack.com

For our inaugural Season 2 episode of the Substack Podcast, we’re pleased to chat with Tony Mecia of The Charlotte Ledger, a publication focused on local business news in Charlotte, North Carolina in the United States.

Tony started as a regular journalist who decided to strike it out on his own. He started a newsletter and spread it the old-fashioned way, relying on word-of-mouth from friends. Today, The Charlotte Ledger is a full-fledged business: when we spoke, Tony had just started hiring freelancers and adding new contributors to his team.

We spoke to Tony about the local news ecosystem, the freedom that comes with writing for a subscriber audience, and his mission to create the sort of local news publication he’s always wanted to read.

Links

* The Charlotte Ledger, founded by Tony

* Facebook’s announcement about giving grants to 400 local newsrooms to support COVID-19 reporting, including Charlotte Ledger

* City Hall Watcher, a publication about the Toronto City Council

* Importantville, a publication about Indiana politics

Highlights

* (04:38) How Tony uses a personal angle to differentiate from other local news outlets

* (10:58) How he grew his list, despite the challenges of a geography-based audience and not having a big name initially

* (16:49) The local news ecosystem in Charlotte, North Carolina

* (22:41) How he launched paid subscriptions

* (33:55) Bringing on freelancers, growing Charlotte Ledger to multiple contributors and writers

On getting started:

I just started out like most people would. I worked here for the paper for 12 years. I left in 2009. It's not like I had a massive social media following or that I was some well-known name in Charlotte by any stretch of the imagination….The piece of advice that I liked from Substack was like, "Okay, look, you can sit around, you can plan this all you want, but actually, why don't you start writing? Just start doing it?"

On the freedom that comes with writing his own publication:

I feel like I'm doing some of the best work in my career. I feel like I'm making a difference just hearing from people, making connections with people, and working with people I want to work with. It's been really exhilarating.

Transcript

Nadia: (00:39)

You write The Charlotte Ledger Business Newsletter, which you describe as, "Fresh and real Charlotte business news that makes you smarter." This is Charlotte, North Carolina, by the way, for people that are listening. I would love to dive –

Tony: (00:53)

Yeah, a lot of times people get Charlotte confused with Charleston, which is in South Carolina, or Charlottesville, which is in Virginia, but no, Charlotte is in North Carolina. You're right.

Nadia: (01:00)

It's funny. All of the Southern states picked their cities to start with Cs.

Tony: (01:05)

Right.

Nadia: (01:08)

I would love to dig into your background. Before this, you worked at The Charlotte Observer, which is a local newspaper, and then you freelanced for a while. Then, you started The Charlotte Ledger about a year ago, and so I'd love to hear a little bit about that trajectory and how you went from being a full-time journalist to… Well, now you're also a full-time journalist who's working for yourself.

Tony: (01:32)

Yeah, sure. Well, I'll just start talking and if you have any questions, just feel free to interrupt me.

Nadia: (01:37)

Sure.

Tony: (01:37)

My background is a journalist. I worked at a newspaper, The Charlotte Observer, for about 12 years. Left there in 2009 as many newspapers around the country started downsizing, buyouts and that kind of thing. Freelanced for a while. I was on staff for The National Magazine for a couple of years. It folded a little over a year ago, and so I started looking around and I said, "Well, gosh, I guess I could go back to freelancing for freelance national publications or websites or what have you."

Tony: (02:07)

I started looking around in Charlotte and realized, well, the scene for local news was really... The newspaper had shrunk a lot. There weren't a whole lot of innovative new digital publications, but I felt like there was still this appetite for local news. I figured, "Okay, look, I have some skills I can bring to bear." Just your normal reporting skills, such as they are, calling people up. What's a news story? What's interesting to people? Writing things in a way maybe that's a little bit interesting. I said, "Well, maybe I could start something up that sort of helped address this issue of a lack of local news?"

Tony: (02:50)

You see this around a lot of communities. I mean, yes, nationally, okay, if you're in New York or Washington or Los Angeles or San Francisco, there are any number of publications, national and local, but some of the mid-sized cities like Charlotte and smaller cities, I really feel like that local news has really taken a beating over the last 10 years. I said, "Look, I've got some skills I could bring to bear. Maybe I could start something up that sort of addresses this need."

Tony: (03:19)

Started looking around. I don't remember how I first saw Substack, but I came across Substack and I started thinking, "Wow, maybe I could start something up", because I had seen all of these national newsletters. You see Axios and The Hustle and The Skim. These were all nationally sort of business-y focused. Because I do that on the local level, just focused on Charlotte. Charlotte, just so you know, it's in a metro area of about 2.5 million people and the City's about 900,000 people.

Tony: (03:52)

I figured, "Okay, maybe I can just kind of give this a go and sort of see if there's a market for this. Is this something that people would be interested in?" The thinking would be use sort of old-school journalism, making it fact-based, making sure it's accurate. Having those be important values, but then also making it kind of punchy and lively and easy to read with a little bit of a voice. The idea was not super long sort of thumbsuckers in the business. Not these really long articles that people have to wade through, but, "Hey, can I do something that's sort of punchy?" I figured, "Okay, so take those skills, put them in this kind of new format, focus it on Charlotte, and then see if there's an interest and kind of see where that goes."

Nadia: (04:38)

I found this really interesting because you went with this newsletter format and you talk about Charlotte Ledger as a newsletter even though it sounds like you were inspired by these national newsletters and you're applying that to a local market. Are there any other sort of local newsletters that you know of in Charlotte or elsewhere as you've been doing this? Have you found inspiration from other people who are trying similar things with local news?

Tony: (05:03)

Yeah, that's a good question. I can tell you locally in Charlotte it's a little bit different than what other people are doing. The traditional model on a newsletter that the main newspaper and the other media in Charlotte do is they use the newsletter as a way to drive people to their website, which a lot of news organizations do. The different here is that I am saying the newsletter is the product. I don't really need you to click anywhere. I think it can create some bad incentives.

Tony: (05:33)

If my model is that I'm selling advertising on a website and I need you as a reader to go to that website and I'm giving you a newsletter, then the incentive is create a bunch of sensationalistic articles and teaser headlines and clickbait to get you to click through to go to that website so that I can sell advertising off of it. I don't like that model as much. I would just prefer to actually just do responsible journalism, put that in the newsletter, and whether you click on... I have a lot of links, the things that I reference, but whether you click on it or not, it's sort of immaterial to me. It's really more about if the goal is to serve your readers and develop this connection with your readers, then I want to serve the readers.

Tony: (06:22)

I want to do what's best for them. I don't want to necessarily…

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com

For our inaugural Season 2 episode of the Substack Podcast, we’re pleased to chat with Tony Mecia of The Charlotte Ledger, a publication focused on local business news in Charlotte, North Carolina in the United States.

Tony started as a regular journalist who decided to strike it out on his own. He started a newsletter and spread it the old-fashioned way, relying on word-of-mouth from friends. Today, The Charlotte Ledger is a full-fledged business: when we spoke, Tony had just started hiring freelancers and adding new contributors to his team.

We spoke to Tony about the local news ecosystem, the freedom that comes with writing for a subscriber audience, and his mission to create the sort of local news publication he’s always wanted to read.

Links

The Charlotte Ledger, founded by Tony

Facebook’s announcement about giving grants to 400 local newsrooms to support COVID-19 reporting, including Charlotte Ledger

City Hall Watcher, a publication about the Toronto City Council

Importantville, a publication about Indiana politics

Highlights

(04:38) How Tony uses a personal angle to differentiate from other local news outlets

(10:58) How he grew his list, despite the challenges of a geography-based audience and not having a big name initially

(16:49) The local news ecosystem in Charlotte, North Carolina

(22:41) How he launched paid subscriptions

(33:55) Bringing on freelancers, growing Charlotte Ledger to multiple contributors and writers

On getting started:

I just started out like most people would. I worked here for the paper for 12 years. I left in 2009. It's not like I had a massive social media following or that I was some well-known name in Charlotte by any stretch of the imagination….The piece of advice that I liked from Substack was like, "Okay, look, you can sit around, you can plan this all you want, but actually, why don't you start writing? Just start doing it?"

On the freedom that comes with writing his own publication:

I feel like I'm doing some of the best work in my career. I feel like I'm making a difference just hearing from people, making connections with people, and working with people I want to work with. It's been really exhilarating.

Transcript

Nadia: (00:39)

You write The Charlotte Ledger Business Newsletter, which you describe as, "Fresh and real Charlotte business news that makes you smarter." This is Charlotte, North Carolina, by the way, for people that are listening. I would love to dive –

Tony: (00:53)

Yeah, a lot of times people get Charlotte confused with Charleston, which is in South Carolina, or Charlottesville, which is in Virginia, but no, Charlotte is in North Carolina. You're right.

Nadia: (01:00)

It's funny. All of the Southern states picked their cities to start with Cs.

Tony: (01:05)

Right.

Nadia: (01:08)

I would love to dig into your background. Before this, you worked at The Charlotte Observer, which is a local newspaper, and then you freelanced for a while. Then, you started The Charlotte Ledger about a year ago, and so I'd love to hear a little bit about that trajectory and how you went from being a full-time journalist to… Well, now you're also a full-time journalist who's working for yourself.

Tony: (01:32)

Yeah, sure. Well, I'll just start talking and if you have any questions, just feel free to interrupt me.

Nadia: (01:37)

Sure.

Tony: (01:37)

My background is a journalist. I worked at a newspaper, The Charlotte Observer, for about 12 years. Left there in 2009 as many newspapers around the country started downsizing, buyouts and that kind of thing. Freelanced for a while. I was on staff for The National Magazine for a couple of years. It folded a little over a year ago, and so I started looking around and I said, "Well, gosh, I guess I could go back to freelancing for freelance national publications or websites or what have you."

Tony: (02:07)

I started looking around in Charlotte and realized, well, the scene for local news was really... The newspaper had shrunk a lot. There weren't a whole lot of innovative new digital publications, but I felt like there was still this appetite for local news. I figured, "Okay, look, I have some skills I can bring to bear." Just your normal reporting skills, such as they are, calling people up. What's a news story? What's interesting to people? Writing things in a way maybe that's a little bit interesting. I said, "Well, maybe I could start something up that sort of helped address this issue of a lack of local news?"

Tony: (02:50)

You see this around a lot of communities. I mean, yes, nationally, okay, if you're in New York or Washington or Los Angeles or San Francisco, there are any number of publications, national and local, but some of the mid-sized cities like Charlotte and smaller cities, I really feel like that local news has really taken a beating over the last 10 years. I said, "Look, I've got some skills I could bring to bear. Maybe I could start something up that sort of addresses this need."

Tony: (03:19)

Started looking around. I don't remember how I first saw Substack, but I came across Substack and I started thinking, "Wow, maybe I could start something up", because I had seen all of these national newsletters. You see Axios and The Hustle and The Skim. These were all nationally sort of business-y focused. Because I do that on the local level, just focused on Charlotte. Charlotte, just so you know, it's in a metro area of about 2.5 million people and the City's about 900,000 people.

Tony: (03:52)

I figured, "Okay, maybe I can just kind of give this a go and sort of see if there's a market for this. Is this something that people would be interested in?" The thinking would be use sort of old-school journalism, making it fact-based, making sure it's accurate. Having those be important values, but then also making it kind of punchy and lively and easy to read with a little bit of a voice. The idea was not super long sort of thumbsuckers in the business. Not these really long articles that people have to wade through, but, "Hey, can I do something that's sort of punchy?" I figured, "Okay, so take those skills, put them in this kind of new format, focus it on Charlotte, and then see if there's an interest and kind of see where that goes."

Nadia: (04:38)

I found this really interesting because you went with this newsletter format and you talk about Charlotte Ledger as a newsletter even though it sounds like you were inspired by these national newsletters and you're applying that to a local market. Are there any other sort of local newsletters that you know of in Charlotte or elsewhere as you've been doing this? Have you found inspiration from other people who are trying similar things with local news?

Tony: (05:03)

Yeah, that's a good question. I can tell you locally in Charlotte it's a little bit different than what other people are doing. The traditional model on a newsletter that the main newspaper and the other media in Charlotte do is they use the newsletter as a way to drive people to their website, which a lot of news organizations do. The different here is that I am saying the newsletter is the product. I don't really need you to click anywhere. I think it can create some bad incentives.

Tony: (05:33)

If my model is that I'm selling advertising on a website and I need you as a reader to go to that website and I'm giving you a newsletter, then the incentive is create a bunch of sensationalistic articles and teaser headlines and clickbait to get you to click through to go to that website so that I can sell advertising off of it. I don't like that model as much. I would just prefer to actually just do responsible journalism, put that in the newsletter, and whether you click on... I have a lot of links, the things that I reference, but whether you click on it or not, it's sort of immaterial to me. It's really more about if the goal is to serve your readers and develop this connection with your readers, then I want to serve the readers.

Tony: (06:22)

I want to do what's best for them. I don't want to necessarily be having them have to navigate to websites and go to a bunch of different places. I want to establish myself as, "Hey, The Charlotte Ledger is giving you everything you need to know. If you want to know more, you can click here and go to the other sources, but you don't have to do that." I think that's important is that if your customer is your reader, then that suggests one way to go, but if your customer is really your advertisers, then that creates a different way to go and you're not necessarily always your readers. I guess I would make that point.

Tony: (06:57)

Then, as far as, are other people nationally doing this? I talked to the people at Substack and they gave me a few names of people who are doing similar things. I talked to a guy in Toronto, we emailed. He's doing one called City Hall Watcher, which is not on business. It's focused on, as the name suggests, on municipal government in Toronto. It goes through lobbying reports and he talks very specifically about what's going on in Toronto city government and developed a following out there.

Tony: (07:32)

I've read some of the other ones on Substack. There's one I think it's called Importantville, which I think is on Indiana politics. I looked at that a little bit. It's my impression that there are not a lot of newsletters that are just squarely focused on local news and using the newsletter as the main platform for local news. There are a few other, I guess, examples here and there, but there aren't a whole lot that I've found.

Nadia: (08:04)

Do you ever find yourself having to explain this when you're reaching out to people for interviews or comments? Or, when you are the publication breaking news – and it sounds like you've broken a bunch of news in Charlotte – how do you position yourself to people that might not necessarily be familiar with the model?

Tony: (08:19)

Yeah, that's a good question –

Nadia: (08:19)

Or do people not even notice the difference?

Tony: (08:21)

Yeah, I mean, some people don't really understand the model. Of course, then, when you're starting up, most people have probably never heard of you, so if I say, "Oh, yes, I'm calling from The Charlotte Ledger", people are like, "Okay, what is that? I don't know what that is." Then, it's, "Oh, it's an E-newsletter", and in their minds they think, "Oh, it's like a small-time thing." It suggests that it's pretty small, and yes, compared to the circulation of the main metro daily newspaper, it is fairly small.

Tony: (08:50)

Then, I've had people say, "Oh, hey, here's something that would be good for your blog." It's like, well, I understand, it's written in a blog-y, sort of conversational style, but I have to constantly explain like, "No, the product is", I say this a lot, "The product is the newsletter. I'm not trying to sell you or get you to go somewhere else." It's like, "The newsletter is what I'm delivering to you and that's what I really want you reading."

Tony: (09:20)

Even though, obviously, Substack does back up to a website and people do get their information in different ways and some people probably just get it from the Substack site and some people get it through the email, that is a question I get. It's like, "Well, why are you doing this as a newsletter? Why wouldn't you just set up a website like most people?" It's like, "Well, there are a lot of good reasons, I think, not to just have it be website-based and that if you're website-based, you're having to drive people to that website.

Tony: (09:54)

The way you typically do that is through social media. You go on Twitter, you go on Facebook, and I think as we all know as anybody who's looked at the publishing industry in the last few years knows, those big tech companies, they really kind of cut you off at the knees. You post something, if you have 2,000 followers, you don't know how many of those 2,000 followers are really going to see it. You're kind of dependent on those tech companies and the social media companies to drive people there. When you have a newsletter, you have a direct connection to your audience. I've got their email addresses, Substack has their email addresses. It just goes directly into their inbox and it shows up there until they opt out of it and say they don't want to receive it.

Tony: (10:34)

It's harder to acquire those customers. It's a little trickier than just getting them to click. You have to get them to put in their email address and some people don't want to do that for understandable reasons, privacy reasons or whatever, but once you have those, you can develop a good relationship with those people. You're deepening that relationship. You're not just kind of saying, "Oh, I just want you to click and move on to the next thing."

Nadia: (10:58)

Makes perfect sense. How did you seed your initial email list? I feel like this is an interesting question for you in particular because your ideal niche audience is a geographic one and not to say like an online interest or community. When you're doing something that's online, how do you reach all of these people who care about Charlotte, the physical location?

Tony: (11:21)

Yeah. No, that's a good question. Well, I just started out like most people would. I worked here for the paper for 12 years. I left in 2009. It's not like I had a massive social media following or that I was some well-known name in Charlotte by any stretch of the imagination. You see like The Athletic, their model is to peel off the best-known sportswriters from the papers and hire them onto The Athletic and to get all of their Twitter followers. That doesn't describe me at all. What I did was I did what most people would do. I started up... The other piece of advice that I liked from Substack was like, "Okay, look, you can sit around, you can plan this all you want, but actually, why don't you start writing? Just start doing it?"

Tony: (12:01)

I didn't plan it out that much. I had kind of a concept in my head. I did one, I did a couple maybe, and then I went on LinkedIn, since it's sort of a business publication, LinkedIn was I think kind of helpful, Facebook, Twitter, and just said, "Hey, friends. I've started this newsletter. It's focused on Charlotte business news. I'd love for you to check it out. Let me know what you think. It's an E-newsletter. Here's how you sign up for it. We're going out three days a week." That kind of thing.

Tony: (12:31)

Right off the bat, I had probably a couple of hundred free subscribers I think in the first three or four days. Then, I just kept producing content, kept producing newsletters. Was doing three days a week, Monday, Wednesday, Friday, just a variety of things and, again, trying to do it in a way that not everybody else in town was doing it. It was important that I have content that was differentiated.

Tony: (12:54)

There wasn't just the same thing that the main newspaper and the alt-weekly, and the digital entertainment publication and everybody else was doing, but it was actually trying to break news or tell you something you didn't know or identifying a trend and then trying to do it also with a very Charlotte kind of voice. This isn't something that could just have been produced in New York or Chicago or wherever, but this is actually specific to Charlotte and it's making reference to things that people know in Charlotte, those touchstones in Charlotte.

Tony: (13:25)

Just started doing it, put it on social media, and then kept producing content. Then, asking people, "Please, if you like it, please tell your friends." It was a lot of word of mouth, and then also as I would report stories and talk to people, interview them, would follow up with them afterwards, send them the articles. Say, "Hey, I quoted you in this article. Let me know what you think. If you like it, feel free to sign up for the newsletter and tell a friend." That kind of thing, so it's sort of on the front end and on the back end, trying to just build it. Over time, it took a while but people kept reading and the free list kind of kept growing from there.

Nadia: (14:06)

It's actually really incredible. I had no idea it just started truly from friends and family kind of start since you've had such awesome list growth since then.

Tony: (14:18)

It's been encouraging.

Nadia: (14:19)

How do people continue finding it? I know you mentioned in your writing that it's just sort of word of mouth. Do you have any sort of like shape around that? Or is it just sort of like somehow it's spreading between people that are reading it?

Tony: (14:34)

Yeah. You know, I don't really have great visibility into that. If you have a website, the metrics that you have on a website, you can see all kinds of things like, who are the readers? How did they get there? Substack has some of that, but oftentimes when somebody signs up, all I really have is the email address for the most part. I don't necessarily know how they got there, whether it's a friend of mine telling the friend, or whether they happen to Google a topic and came across it and signed up. I don't have a lot of visibility into that, so I can't really tell you. I just kind of know what I've done and I can tell you that I believe is kind of word of mouth.

Tony: (15:16)

Then, occasionally, a lot of it is content-driven, too. Not all of it, but if I have a big story, if I'm able to break a story and beat the competition on a story and then they recognize that it's a story and write about it and happen to credit me as breaking it, that is helpful, too, sort of leveraging those audiences who have bigger audiences. If the audience of The Charlotte Observer sees, "Oh, this was first reported in The Charlotte Ledger", well, they're much bigger than I am, and so if somebody reads that and says, "Well, what is The Charlotte Ledger? Let me check that out." That can be very helpful, too.

Tony: (15:52)

It's not just about the content because a lot of times, I think, you can have really good content and nobody will see, it, but there are ways to kind of... Partnerships are kind of a big thing in a lot of these circles to help leverage someone else's audience to grow your audience. Then, you mentioned them and it helps their audience. It's not exactly everybody scratching each other's back kind of a thing, but it can oftentimes sort of work out that way. I mean, there are different partnerships that I've kind of developed that I think have been helpful, but it's not like there's just one major one.

Nadia: (16:28)

That makes sense. It feels like those two things almost go hand-in-hand of having really great content and then also doing that extra work to make sure that you're maximizing the surface area of people that are going to be able to discover it, but if people are discovering it and it's not good or you write good stuff and no one's discovering it, then it's not going to work out either way. It definitely seems like you've got both.

Nadia: (16:49)

I'm curious, as you're talking about making reference to local news in Charlotte, I confess, I really just don't know very much at all about the world of local news except that I hear headlines that it's dying. I'd love to hear a little more explicit of your take on within Charlotte, who are the major players or institutions? Within that, what is local business news like since you focus specifically on business news? Does it have the same sort of trajectory that we're hearing about local news? Is there a different sort of revenue model? Is there anything different about that sort of space?

Tony: (17:27)

Yeah. Well, I can just tell you a little bit about Charlotte, and I hope that doesn't bore people, but it just kind of helps you understand the competitive environment here. Obviously, the biggest player for many, many years was the big metro newspaper, which in our case was The Charlotte Observer, where I used to work. When I was there, we had a print circulation of 250,000 people. That was about 15 years ago. Now, the print circulation is more like 60,000. It went from a newsroom of 250 journalists to now a newsroom of 40 journalists over the span of 15 years. You can see that the main metro newspapers are shrinking and so they can't do the sorts of things that they used to be able to do even though there's still an audience for the kind of work that they used to do. That's sort of the main one.

Tony: (18:09)

As far as business, we have a business journal, The Charlotte Business Journal. They have a print product. It's weekly. They have, obviously, a digital product. They do a lot of events. They channel a lot towards events and awards and sort of selling ads to the business community. There's a new-ish digital publication in town called Charlotte Agenda. It's entirely online, started five, six years ago. It's received some national attention. I mean, a lot of their coverage traditionally has been on dining and entertainment, sort of geared toward Millennials, the people in their 20s and 30s who are just moving to town and want information. Mostly directed at that group. They've made some moves in the last few months. Hired a journalist from The Charlotte Observer. They brought in another one from The City Magazine. They're trying to bulk up sort of their journalism chops a little bit.

Tony: (19:22)

Obviously, you got the public radio station. I've got a partnership with them, actually, where I'm on the air once a week talking about Charlotte business news, so that's sort of a nice little thing where it kind of gets me a little bit of exposure and gives them insight into the business news and they don't really have a business reporter for the most part. You have the TV stations. That's I think a little bit of a different audience there. They still have a fair number of people watching TV news.

Tony: (19:51)

Then, there are a number of other publications. There's the alt weekly, there's The Charlotte Magazine, there's any number of other, and I'm probably leaving some off, but a number of smaller publications. It's not that there's no coverage of local news in Charlotte. There definitely is, it's just it's a big city and the number of journalists working in Charlotte has definitely declined over the last 10 or 20 years. I think there's room to be doing more things. As it relates to business journalism, the big players often is thought of being The Business Journal, and circulation-wise, I think their print circulation is somewhere between 10 to 12,000 or something like that. Actually, I'm not exactly sure. Maybe I'm confusing that with their digital circulation. They're sort of the big player.

Tony: (20:46)

I'm trying to do content that's different than they do. I'm trying to sort of make it a little bit punchy, trying to make it a little bit fun, shorter, kind of quick hit pieces. Again, my audience is the reader. I am not dependent on advertising sales to big companies, so I don't have to soft pedal it toward big companies, for example. If I'm working for the reader, I can be truly kind of independent and I sort of live or die on what the readers think, so for journalists, that's always sort of what you want is to be working for the readers. That's just sort of the lay of the land here.

Tony: (21:37)

I think just generally a lot of people I talk to in Charlotte, they sort of lament the decline of local news and they say, "Oh, this is great that you're doing this. Charlotte needs something like this. Good luck to you. I hope you can grow it. I think it's a good thing." It's probably a little bit of self-selection bias that they like what I do and they tell me they like it. I'm sure there are people that don't like it, but you don't have to please everybody. The numbers are such, to make this work as a viable business, you don't need 200,000. If you can just kind of sort of do the math and say, "Okay, if I have a thousand people and they're paying a hundred dollars a year, well, you can do the math and say, 'Well, okay, that's how much money this brings in.'"

Tony: (22:24)

The numbers are not as big or as daunting. I think you're finding that probably not from other Substack writers that there's a saying that, "All you need is a thousand dedicated fans who are willing to pay you", and you can make a living off of that. I think that's definitely true.

Nadia: (22:41)

I'd love to dig into this model a little bit more for you.

Tony: (22:44)

Sure.

Nadia: (22:45)

You went paid pretty recently, actually, adding paid subscriptions to The Charlotte Ledger. I think it was like a year into you were starting to write. Did you know that you were going to eventually make this a paid thing when you started it? Did it start out as just as like, "I'll see where it goes and if I can get enough people to sign up"? Why did you finally decide to go paid?

Tony: (23:07)

Well, yeah. When I started, I mean, I knew Substack's model and I knew that that ultimately would probably be the endgame. When I started it up, I said, "Well, let's just see if there's a market for this." I didn't really know and you never really know when you start. I figured, "Well, if I start it and nobody really reads it, then, okay, maybe I'll sort of move on to something else and figure something else out." It kept growing and I kept adding free subscribers. It was about the rate of maybe 200 to 300 free subscribers a month or so. It was fairly consistent numbers on that.

Tony: (23:43)

I kept it free for a fairly long period of time. I know Substack probably would have recommended a shorter period for that, but I really wanted to get the free numbers up because I perceived that it might be harder to kind of keep growing that free list once you switched to paid. I really wanted to get that number up. I had initially thought, "Oh, it'll be great if I could get to 10,000 free subscribers." I had no idea how long that would take and I never got anywhere near that, but after about eight months, I was at about, I don't know, 2,000, 2,500 free subscribers or so. This was I think back in November. I think it was about 2,000 free subscribers back in November.

Tony: (24:26)

I said, "Okay, well, here's what I'm going to do." I put out a post and said, "I'm going to go to a paid subscriber model starting in late winter/early spring and here's why. Here's the rationale." It's all of the things that if you read anything that Substack puts out, it's all the same sort of thing, direct connection with the reader, develop a community, giving you important insight, if you value it you should pay for it, those kinds of things. That's a little tricky, too, to tell people. A lot of times people are used to getting news, especially local news, for free. We can get a lot on the internet. You can watch it on TV. It's like, "Well, what are you adding that is making it that I should pay for it?"

Tony: (25:07)

Again, the argument I was trying to make was, "I'm giving you something you literally cannot get anywhere else. If you want to know about the Trump Administration and what they're doing, you have dozens and dozens and dozens of potential sources for that, but if you want to know what's going on in South Charlotte on this particular plot of land where developers are wanting to build a shopping mall, you're not going to get that anywhere else except for The Charlotte Ledger." It was making those sort of arguments. I did that in November, announced that in November, and then in late February, I did another couple of posts. I said, "Okay, we're going to a paid subscription model. Here's how it is. Here's how much it works, or here's how much it costs, here's how it works."

Tony: (25:47)

I said, "$9 a month or $99 a year." Then, I also had a premium tier that I aimed at companies and people who wanted to give more. It was $379 a year. I sort of laid that out there. By that point, I had about I guess around maybe a little more than 3,000 people on the free list. The first day, it was great to see. I put it out there and then, boom, it just started coming in. After being like basically at zero revenue for 10 months, to actually have some money coming in, I can tell you, Nadia, it was just a great feeling to be able to do that and say, "Okay, this is very validating here." It's personally validating to know that people want to pay for what you produce, but it's also nice to have some money coming in. I've used a few freelancers and kind of gone out of pocket for. It's just nice to be able to kind of get some of that money in.

Tony: (26:54)

The first few days, there was just a pretty big spike and I basically left open this two-week window where I said, "Okay, I'm going to switch to paid subscriptions", but then the first paid post was going to be March 11th, sort of ramped up. I had a bunch of good content lined up. I had some good freelancers who had written some really smart things. Just try to take advantage of that two-week period as much as possible. Got a bunch of people signing up. Money kind of came in. Did that first paid post March 11th. Again, I saw a pretty good increase. You all had said... I had talked to Chris or Hamish and they had said, "Well, you can probably expect at the beginning you'll see a rush and then at the end you'll see a rush", and that's exactly what happened.

Tony: (27:43)

We did that first paid post March 11th, and then I was thinking, "Okay, I'll have some money coming and I'll kick back and sort of figure out the next step." Of course, that's right when this coronavirus stuff started hitting. I mean, my timing on switching to paid was actually pretty fortunate in the sense that if I had waited any longer, it would have gotten completely lost in all of the coronavirus stuff that's going on. The timing wound up being pretty good.

Nadia: (28:10)

Did you find that... You started reporting also, obviously, on how the crisis has been affecting Charlotte. You got this awesome grant from the Facebook Journalism Project to focus on reporting about the crisis in Charlotte. Did you find on balance that the crisis has been... I don't know exactly how to –

Tony: (28:39)

I understand what you're saying.

Nadia: (28:40)

Yeah.

Tony: (28:42)

Yeah. I initially was going three... well, I'd gone three mornings a week and then right before I announced that I was going to start switching to a paid subscription, I added a fourth day a week on Saturdays, which I had envisioned as I'm going to basically kind of roundup the news of the week and also use that as a way to point people toward the paid content that free subscribers wouldn't have seen. Saturday was going to be it's a free content day. The paid days would be Wednesdays and Fridays, and so the free days would be Mondays and Saturdays. The Saturday one was going to be a roundup, pointed people toward the paid content so the free subscribers could see and say, "Oh, wow, that sounds really good. I should subscribe."

Tony: (29:24)

That was my initial conception. Then, the coronavirus thing hit and I kind of had to make a choice. I could either sort of lay back and kind of stay on that schedule of what I was doing and keep the focus on business news as I had been, but I kind of felt like if I did that, it would... It's hard to write about just business stories when you have all of this stuff going on locally in which you don't really have enough journalists in town to cover it all. I kind of made the decision. I'm like, "Okay, we're going to ramp this sucker up. We're going to go from four days. We're going to come out now as much as we can." We've been going... As we're talking, this is recorded in the second week of April, and we've been going every day for the last month pretty much, seven days a week and a lot of that's with freelancers. I can't crank out that much content.

Tony: (30:22)

That's just saying, "Okay, look, this coverage is not necessarily business coverage, but it's important to the community. A bunch of the businesses are kind of shut down anyway, so let's just do good coverage." I've always thought, "Let's just do good material that's local rather than say, 'Oh, well, that's not a business story so I'm going to ignore it.'" It was sort of that decision where it's like, "Okay, let's go to seven days a week." It's not like there's any shortage of things to write about. It's not like some artificial thing where I'm saying, "Oh, we need to go to seven days a week. What are we going to put in tomorrow." There are multiple things going on every single day, so I sort of decided to do that.

Tony: (31:08)

Then, actually, the number of paid subscriptions throughout, they've continued to come in. I mean, it's not like they were during that two-week period where I had announced the paid subscription but hadn't turned it on yet, but we'd be getting a few every day. That's been positive. The nice thing about this model is that if you do good work and people like it, they subscribe. That's just very validating. That's just a very positive, positive thing, I think, not just for The Charlotte Ledger, but I think it's positive for the community.

Tony: (31:44)

That's one of the arguments, too, is that, "Look, this is a community good. This is something that actually Charlotte needs and it is good for Charlotte." That's really the motivation in starting it up. It wasn't like, "Oh, how can I make a bunch of money? Oh, I'm going to start a local media company. That's a genius move. That's a way to like cash in or whatever." I wouldn't advise people if they're in it for the money, starting up a local media company is probably not where you want to be just generally. Go into like Fintech or something like that. If you do the work... I think our work is good and I'm happy there are paid subscribers who agree.

Nadia: (32:28)

It's cool hearing the story about how you started to add in more coronavirus coverage to your business coverage because, to me, it feels like the kind of thing that having this more independent model is better suited for it. People are subscribing because they care about your perspective and you're offering them this point of view and this style of writing that they're not going to find anywhere else. Yes, you are a business newsletter and you're focused on writing about business news, but when something crazy sort of like once in a century happens, it's also possible to write about those things and have people say, "I'm here because I love your perspective on things. I want to hear what you think about all of these things." Right?

Tony: (33:09)

Yeah. That's been kind of interesting, too. If you come from a traditional journalist background, you're sort of programmed to just be completely neutral, right? I tried to have a little bit more opinion and a little bit more edge. I find that people... I don't know. I know that people tend to read and tend to consume what they agree with, but I get nice notes. I got one the other day from somebody saying, "Hey, I completely disagree with you on this, but I love The Ledger. I think you're wrong on this, just so you know." That kind of thing, which is kind of a nice... You can have like a respectful dialogue. It's one of these things that you kind of always want to have, that sometimes you hear about people trashing each other on social media or whatever. It's actually kind of nice. That's kind of been positive, too.

Nadia: (33:55)

As you were bringing on, you mentioned that you've had freelancers who are also helping to write for The Ledger. You recently announced that you brought on a managing editor and you have a contributing editor and you have like a whole kind of staff now that you're spinning up. You've got swag I saw, which seemed great. It's starting to be like more of this thing now. Given that part of the origin was you had this sort of specific voice and perspective that people are subscribing to, what is it like bringing on more people in that sort of context going from just you writing to people writing or whatever number of people writing? How do you sort of manage that?

Tony: (34:39)

Yeah, that's a good question because when I started this up, I kind of didn't really know like, "Okay, well, I'll just kind of try this on a lark." Then, you kind of do it and you get kind of locked in where it's like once there's a little momentum behind you, it's hard to just say, "All right, I want to do something else", and pull the plug. There are actually now a whole bunch of people who are reading and then they got freelancers and all of this. No, I basically said I was going to bring in... I knew when I was ramping up to paid that it would be nice to have some other content and other people providing content to take the burden off of me.

Tony: (35:12)

There are a number of journalists in town who have left the newspaper or are available who are now freelancing that I knew and that I could reach out to. I knew I would have this money coming in as soon as I turned on the paywall, so I was able to basically kind of borrow against that, pay some of the freelancers to do a little bit of work. It's like on the one hand you want to kind of keep the voice and keep the kind of tone and attitude. Sort of as you grow, I don't necessarily want to force people who are writers to just develop my tone and my attitude. I still try to write as much as I can, but during this whole coronavirus issue, it's like I definitely need freelancers to do that, to help out with that coverage.

Tony: (36:08)

As you mentioned, I did apply for a grant from Facebook and they came through and they've been funding a bunch of local news initiatives related to coronavirus. I got a $5,000 grant from them, so that helps pay freelancers, which is a big help. I just brought on this week, as we're talking here in the first part of April, a managing editor. It's someone I've known for 20 years who was at The Charlotte Observer. She decided to leave and come onboard with The Ledger, which is great. That is something that you kind of have to manage a little bit, again, but if the proposition is we're telling you things that you don't know and we're breaking news and we'll maybe give you some feature stories here and there, I think it's okay to have a few different voices.

Tony: (36:54)

There's this whole thing now where people sort of identify with personalities. I've never really been comfortable kind of being like the front person on this or my face associated with it or whatever, but I acknowledge that's sort of the reality now. I think it's okay to bring in multiple people. I think the results, I hope, will speak for themselves.

Nadia: (37:20)

They definitely do. Something I really love about just reading some of your writing is that this like heart and this mission really come through. You do explicitly say that you're doing this because you really want to offer something new and not just provide yet another kind of local news option. You're really trying to push the medium forward and push the conversation forward, which I think is just so awesome.

Nadia: (37:42)

It's made me kind of think like, you know... Maybe this is sort of like more of a philosophical question, but do you think of The Charlotte Ledger as... Would you put it in the bucket of a newspaper? Or a newsletter? Or is it like you and a bunch of other awesome people who are essentially freelancing with a platform? As you think about your plans for the future, as you think about growing, what sort of bucket do you mentally put it in?

Tony: (38:11)

Yeah, that's a really good question. I think the important thing and sort of the philosophy I have behind it is like I just want to tell you stuff that you don't know and stuff that makes you smarter. I think what Substack has proved is that there are multiple audiences for many, many different things, whether it's feminist poetry or 15th century literature or current events or tech or whatever, there are multiple, multiple audiences. What I'm trying to do with this is say, "Okay, my audience is people in Charlotte who are interested in their city and what's going on in their city and want to learn stuff about it and get insights and information that they can't get anywhere else."

Tony: (39:00)

As long as we're kind of doing that, whether it's my voice or whether it's someone else's voice or whether it's a combination of voices, I feel like that's going to be okay. I think that's going to kind of work itself out. I just want to constantly be doing just smart stories and sort of things that aren't obvious. I think we're going to be able to do that even as we have different people providing that information. I guess it's sort of a hybrid of all of those things that you mentioned, so it's sort of like a newspaper in that sense, but it's also kind of like a blog in the sense that it's kind of chatty and conversational.

Tony: (39:45)

It's also very kind of staccato. We're not doing a whole bunch of long-form stuff. I mean, we could. There are ways to do that. We could put a long-form thing on the website and excerpt it in the newsletter. There are all kinds of possible combinations. It's sort of a mixture of all of the above, but I'm trying not to make it just purely opinion thing. What I really wanted to do is not just be reactive to what everybody else is reporting, but I really want to do original pieces and have people talking about us and looking to us as a source of information.

Tony: (40:23)

The other part of it is, if you're serving your reader, you can kind of be above the fray. I don't mind if The Charlotte Observer or Charlotte Agenda or The Charlotte Business Journal, if they've got a good story, I don't mind mentioning it and saying like, "Hey, you should check out this thing in The Charlotte Business Journal they had on how many people are paying their rent this month during the coronavirus", or whatever, and you could link to it. I want to establish us as a trusted source that is sort of agnostic about where the information comes from.

Tony: (40:54)

A lot of places, that's not a traditional news mentality. The mentality traditionally, certainly in local news, is, "Hey, if you have a story, you promote that story and you kind of pretend that like nobody else exists." That just doesn't reflect reality. I have no problem. If somebody has a good story, I'd like to send them to the story because I'm working for the reader. If I can say to the reader, who is my customer, "You should go check out this story over here", then that serves my reader. It might give a click to this other publication, but that's fine. It's just kind of a different mentality, so I don't really know quite what bucket to put it in, Nadia, but it's kind of a hybrid, I guess.

Nadia: (41:38)

What is it about, I guess, everyone else's model that makes it harder for them to do that? Is it just because they are more about driving readership numbers and having exclusive information does that better?

Tony: (41:53)

Other models that are out there, I think... I just really like the model. I like having that direct connection with readers. It's just very simple, it's very straightforward. It's like in pretty much any other industry that if you find value in something, you pay for it. I think in media, a lot of times that can get very confused if you're very dependent on advertising.

Tony: (42:14)

I think it can be kind of confusing toward readers toward, are your interests in looking out for the readers? Or are they in looking out for the advertisers? Is this paid content? Are advertisers paying for this content? Or is this legitimately your honest opinion? I think it can get very confusing, I think, for readers. I don't care for those models as much. I would prefer to do what I'm doing with a direct connection to the readers. I think it's a little bit cleaner.

Nadia: (42:43)

This has made me wonder how you decided on your pricing, especially given that for local news, I guess, people are sort of mentally used to maybe more of an advertising model. How did you come up with your numbers?

Tony: (42:55)

Well, I had months and months to kind of think about this and work on this. I'd loved to tell you there's some scientific reason I settled on $9 a month or $99 a year, but it was really just sort of... A lot of people said, "Don't underprice." I had a few people who had newsletters that told me that. Then, the other part is if it's a business publication, and I sort of straddle that line between just doing pure sort of business stuff and things that are little more sort of direct to consumer, general kinds of things. I said, "If you're a business publication, you can probably command a little bit of a higher price because people are going to be able to expense for this business." They can put it on their company credit card and they can write it off as an expense if they're a small business owner.

Tony: (43:44)

You can kind of capture some of that. I think the minimum on Substack was $5 or $6 or something like that, but I said, "Okay, let's go up to nine. Part of it was also kind of marketing, thinking, "Okay, like when you go buy gas, it's like $2.19 and nine-tenths. I was like, "Let's keep it under 10. Let's go nine", and then same thing on the yearly." I said, "Let's go 99 because it sounds cheaper than a hundred I think mentally." That's sort of like I said not really scientific but that's sort of what I landed on.

Nadia: (44:23)

Makes sense. Just to sort of wrap up the conversation a bit, now that you've been doing this for a while, I'm wondering just from the personal side, what has it felt like to write for essentially yourself or for the reader versus writing for The Charlotte Observer versus the tine that you spent freelancing? You've really seen all different aspects, I guess, of doing local journalism and the good and the bad. Just would love to hear from a personal side, how does it compare?

Tony: (44:55)

That's a really good question. There's positives and negatives. The one thing is, it's extreme... Well, I mean, let's just break it all down. It's extremely liberating to just be able to kind of write whatever you want to write on the one hand. You have a whole bunch of freedom that if you're coming from a traditional media organization, you might not have if you have an editor that doesn't want this kind of story but wants that kind of story. I can pretty much do what I want to do, on the one hand.

Tony: (45:26)

Now, on the other hand, I don't really have, or I haven't had until lately, really an editor. Editors can actually make stories better. If you have a good editor, that can really make all of the difference in the world. On the one hand, the good news is I didn't have an editor. The bad news is, I don't have an editor, so that's kind of a plus and minus. The other thing I'll say is that since I'm sort of doing this for myself, I'm a lot more invested in it and I'm willing to spend more time in it than I would if I were just an employee of somewhere. This is kind of my baby.

Tony: (45:59)

Fortunately, there is something like Substack that allows you to do something like this, but it's like I was able to create this, and so I'm invested in it and I'm invested in its success. That is very motivating. It makes me spend a lot of time on it because I want it to be good. I don't just want to do it kind of halfway. I really want it to be good. The downside of that is I wind up spending a lot of time, a lot of late nights, a lot of getting up early in the morning, a lot of kind of extra phone calls, a lot of things.

Tony: (46:35)

It's tremendously fun and exhilarating and there's a whole strategy side of it that I haven't really had to deal with before but that's kind of interesting and neat. It's not just the writing, but there's the whole marketing side and the business side and all these kinds of partnerships and things like that. That's tremendously fascinating and it's also a little daunting because it's like, "Do I really know what I'm doing here?"

Tony: (46:56)

There are pluses and minuses, and I'm sure you hear this from a lot of other Substack writers, but it's like you can spend a lot of time. You can really pour your heart into something and spend a lot of time doing it because you want it to be good, and so that's just sort of a consideration. I guess if you're just somebody who wants to kind of occasionally write, it might not quite be the thing for you. There are a number of pluses and minuses, I guess.

Nadia: (47:28)

Sounds like an adventure.

Tony: (47:31)

Definitely an adventure. It's been a lot of fun. It's been really tremendous and it's been great. I feel like I'm doing some of the best work in my career. I feel like I'm kind of making a difference just hearing from people, making connections with people, and working with people I want to work with. It's been really exhilarating. It's been a lot of fun.

Nadia: (47:52)

That's a great note to end on. Thank you, Tony, for joining and chatting with me.

Tony: (47:57)

Thanks, Nadia.

Get on the email list at on.substack.com

We invited Delia Cai, author of Deez Links, to speak to an audience of Substack writers in New York about how she grew her newsletter to 2,700 signups. Delia started her daily media newsletter as an intern at Atlantic Media.

This transcript has been lightly edited for readability. You can also check out the slides from Delia’s talk..

Takeaways

* Be your newsletter’s wingman. Talk it up to everyone.

* Borrow other people’s audiences to reach new readers.

* Build credibility by getting other people to write about you.

Why Delia started a newsletter

I write a newsletter called Deez Links. It’s basically a daily-ish media newsletter that sends you a link to something worth reading, tied to the larger media industry.

I started Deez Links four years ago, when I was just out of college. I had an internship at Atlantic Media that was cool, and not cool, in that I spent all of my time just reading news about the industry, and I was writing corporate memos. It was cool because I was learning a lot about digital media, but I was also just sitting in a cubicle all day, not interacting with other humans. 

This was 2015, 2016, around when newsletters like Today in Tabs and Ann Friedman's newsletter were getting a lot of hype. I was reading those and I was like, “This is so cool. I want to try to do this. I want to try to write in some kind of outlet that isn't just in corporate memo speak and maybe I can just do this for my friends and it will just be a funny thing that I do during the work day.”

So I started Deez Links. It was on TinyLetter. I made the logo in three seconds in MS Paint. It was an extremely lo-fi situation.

I sent it out to my friends, friends from college, and friends that I worked with and I was just like, “I'm going to do this every day. Let me know if this is interesting.” I had no real aspirations for it other than just getting in the practice of writing about something every day.

Deez Links grew to about 500 subscribers by 2018, which was fine. It was mostly people that I'd met on the internet, or just people that I knew personally. Then I moved it to Substack in 2018, and since then it's gone through this amazing growth trajectory to where I had 700 subscribers and got a shout-out in New York Magazine and Vanity Fair. We're also doing this merch store which is really cool, which has taught me a lot already about ecommerce and supply chains.

Deez Links was mostly people that I'd met on the internet, or just people that I knew personally. Then I moved it to Substack in 2018, and since then it's gone through this amazing growth trajectory to where I had 700 subscribers and got a shout-out in New York Magazine and Vanity Fair.

Looking back over those four years, it seems like there's this very calculated path to growing the newsletter, and I have to be totally honest and admit there was not. I was just bumbling along. This was my passion project. I just tried a bunch of things, so I’ll share with you the three buckets of things that have worked out for me.

Be your newsletter’s wingman

So the first one is super obvious. It's just to be your newsletter's wingman.

I think the really wonderful thing about newsletters is they're so personal. They're tied to you and your name most of the time. Bring it up to your friends, your work friends, while applying for a job. I put my newsletter in my resume. And I was like, “I don't know if this is work appropriate, but this is what I got.”

When you start a newsletter, you may not have a lot of cred to go off of. You don't have a built-in audience unless you're already a writer on other platforms, and I didn't have that. I was just out of college.

Your first 500 subscribers are going to be the people who are just naturally invested in you, your friends and your mom. So you should make your newsletter an extension of yourself and bring it up all the time when you're talking to people in your circles.

I think the trick to this is always consider how to widen that personal circle, whether it's going to meetups, going to hangouts, or interacting with people on Twitter and making Twitter friends, which is my favorite thing. That way you're always adding to the circle and you're being your own best advocate for the newsletter.

Then at the end of the day, after you've bonded and had a normal human social exchange, you can say, “Yo, I have a newsletter. I write about X, Y, and Z. I would love to know what you think about it.” Telling them to Google it, or even texting them the link, is super easy. That way, you’re treating it as a way to stay in touch with people that’s less weird than, “Can I add you on LinkedIn?” It's like “Hey, we bonded. Do you want to support my art a little bit?”, which feels like a more natural ask.

Borrow other people’s audiences

The second tactic  I stumbled upon was borrowing, or being exposed, to other people's audiences. I think this is the most effective one.

I ended up coming across this tactic in three different ways. One was with classifieds. When I first started out, I was thinking, “I'm a young woman in media. I feel like other young women in media would like this newsletter, what are they reading right now? What am I reading right now?”

I loved Ann Friedman's newsletter. She had this huge subscriber base, mostly women, and her newsletter is tied to current events and news as well. I feel like that's my audience. And she does this thing where she’ll place classified ads on her newsletter. It costs $50 to write a 140-character line about why you should subscribe to Deez Links and put the link in there. So that went out in her newsletter and I got 70 subscribers from doing this, which doesn't sound amazing, but when I first started out, it was like great. I didn't have to meet 70 people to do this. I just put an ad in this newsletter with a very loyal following.

The other tactic that I accidentally came across, in terms of borrowing other people's audiences, was doing weekly Q&As. I first had this idea in 2018 where I was like, “I'm just going to do a Friday Q&A with someone in media, just ask them questions about their job.” Like if you cover Congress, what do you have to wear? What does that mean? Or if you do PR for the avocado industry, do you get free avocados? Just dumb questions that I would ask my friends anyway.

I started doing them with my friends, and then once I ran out of friends to bug, I started branching out to people I really admired on Twitter, people I knew from work. And just realized this golden rule of how the internet and media works: if you interview someone, they're very likely going to share it with their following, and that's how you get exposed to their audience.

If you interview someone, they're very likely going to share it with their following, and that's how you get exposed to their audience.

For example, I did an interview with Alana Hope Levinson, the Deputy Editor of MEL magazine earlier last year. When it came out, she shared it with her followers. And she had a huge Twitter following. Then MEL magazine tweeted out to all of their readers, and I was like, “Oh, this is how it gets done.” With each weekly interview I do, I've noticed I get a handful of followers, especially when it's someone who has a very loyal following and audience of their own.

Finally, honestly, the single biggest boost I got in terms of sign-ups was through a newsletter swap with this lifestyle site called The Good Trade. I wasn't super familiar with them, but their managing editor reached out to me at some point last year. I don't know if she found me through the classifieds, but she was like, “I love your newsletter. We have one, too, it's called The Daily Good. It seems like maybe we would have the same kind of audience. Let's do newsletters.” And I was like, “Yeah, sure.” But I had no idea what that even meant. I was just like, “I'm open to anything.”

What I found out it meant was basically just plugging each other's newsletters. They wrote their own line and I put it in mine. So I wrote, “If you love a good…

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com

We invited Delia Cai, author of Deez Links, to speak to an audience of Substack writers in New York about how she grew her newsletter to 2,700 signups. Delia started her daily media newsletter as an intern at Atlantic Media.

This transcript has been lightly edited for readability. You can also check out the slides from Delia’s talk..

Takeaways

Be your newsletter’s wingman. Talk it up to everyone.

Borrow other people’s audiences to reach new readers.

Build credibility by getting other people to write about you.

Why Delia started a newsletter

I write a newsletter called Deez Links. It’s basically a daily-ish media newsletter that sends you a link to something worth reading, tied to the larger media industry.

I started Deez Links four years ago, when I was just out of college. I had an internship at Atlantic Media that was cool, and not cool, in that I spent all of my time just reading news about the industry, and I was writing corporate memos. It was cool because I was learning a lot about digital media, but I was also just sitting in a cubicle all day, not interacting with other humans. 

This was 2015, 2016, around when newsletters like Today in Tabs and Ann Friedman's newsletter were getting a lot of hype. I was reading those and I was like, “This is so cool. I want to try to do this. I want to try to write in some kind of outlet that isn't just in corporate memo speak and maybe I can just do this for my friends and it will just be a funny thing that I do during the work day.”

So I started Deez Links. It was on TinyLetter. I made the logo in three seconds in MS Paint. It was an extremely lo-fi situation.

I sent it out to my friends, friends from college, and friends that I worked with and I was just like, “I'm going to do this every day. Let me know if this is interesting.” I had no real aspirations for it other than just getting in the practice of writing about something every day.

Deez Links grew to about 500 subscribers by 2018, which was fine. It was mostly people that I'd met on the internet, or just people that I knew personally. Then I moved it to Substack in 2018, and since then it's gone through this amazing growth trajectory to where I had 700 subscribers and got a shout-out in New York Magazine and Vanity Fair. We're also doing this merch store which is really cool, which has taught me a lot already about ecommerce and supply chains.

Deez Links was mostly people that I'd met on the internet, or just people that I knew personally. Then I moved it to Substack in 2018, and since then it's gone through this amazing growth trajectory to where I had 700 subscribers and got a shout-out in New York Magazine and Vanity Fair.

Looking back over those four years, it seems like there's this very calculated path to growing the newsletter, and I have to be totally honest and admit there was not. I was just bumbling along. This was my passion project. I just tried a bunch of things, so I’ll share with you the three buckets of things that have worked out for me.

Be your newsletter’s wingman

So the first one is super obvious. It's just to be your newsletter's wingman.

I think the really wonderful thing about newsletters is they're so personal. They're tied to you and your name most of the time. Bring it up to your friends, your work friends, while applying for a job. I put my newsletter in my resume. And I was like, “I don't know if this is work appropriate, but this is what I got.”

When you start a newsletter, you may not have a lot of cred to go off of. You don't have a built-in audience unless you're already a writer on other platforms, and I didn't have that. I was just out of college.

Your first 500 subscribers are going to be the people who are just naturally invested in you, your friends and your mom. So you should make your newsletter an extension of yourself and bring it up all the time when you're talking to people in your circles.

I think the trick to this is always consider how to widen that personal circle, whether it's going to meetups, going to hangouts, or interacting with people on Twitter and making Twitter friends, which is my favorite thing. That way you're always adding to the circle and you're being your own best advocate for the newsletter.

Then at the end of the day, after you've bonded and had a normal human social exchange, you can say, “Yo, I have a newsletter. I write about X, Y, and Z. I would love to know what you think about it.” Telling them to Google it, or even texting them the link, is super easy. That way, you’re treating it as a way to stay in touch with people that’s less weird than, “Can I add you on LinkedIn?” It's like “Hey, we bonded. Do you want to support my art a little bit?”, which feels like a more natural ask.

Borrow other people’s audiences

The second tactic  I stumbled upon was borrowing, or being exposed, to other people's audiences. I think this is the most effective one.

I ended up coming across this tactic in three different ways. One was with classifieds. When I first started out, I was thinking, “I'm a young woman in media. I feel like other young women in media would like this newsletter, what are they reading right now? What am I reading right now?”

I loved Ann Friedman's newsletter. She had this huge subscriber base, mostly women, and her newsletter is tied to current events and news as well. I feel like that's my audience. And she does this thing where she’ll place classified ads on her newsletter. It costs $50 to write a 140-character line about why you should subscribe to Deez Links and put the link in there. So that went out in her newsletter and I got 70 subscribers from doing this, which doesn't sound amazing, but when I first started out, it was like great. I didn't have to meet 70 people to do this. I just put an ad in this newsletter with a very loyal following.

The other tactic that I accidentally came across, in terms of borrowing other people's audiences, was doing weekly Q&As. I first had this idea in 2018 where I was like, “I'm just going to do a Friday Q&A with someone in media, just ask them questions about their job.” Like if you cover Congress, what do you have to wear? What does that mean? Or if you do PR for the avocado industry, do you get free avocados? Just dumb questions that I would ask my friends anyway.

I started doing them with my friends, and then once I ran out of friends to bug, I started branching out to people I really admired on Twitter, people I knew from work. And just realized this golden rule of how the internet and media works: if you interview someone, they're very likely going to share it with their following, and that's how you get exposed to their audience.

If you interview someone, they're very likely going to share it with their following, and that's how you get exposed to their audience.

For example, I did an interview with Alana Hope Levinson, the Deputy Editor of MEL magazine earlier last year. When it came out, she shared it with her followers. And she had a huge Twitter following. Then MEL magazine tweeted out to all of their readers, and I was like, “Oh, this is how it gets done.” With each weekly interview I do, I've noticed I get a handful of followers, especially when it's someone who has a very loyal following and audience of their own.

Finally, honestly, the single biggest boost I got in terms of sign-ups was through a newsletter swap with this lifestyle site called The Good Trade. I wasn't super familiar with them, but their managing editor reached out to me at some point last year. I don't know if she found me through the classifieds, but she was like, “I love your newsletter. We have one, too, it's called The Daily Good. It seems like maybe we would have the same kind of audience. Let's do newsletters.” And I was like, “Yeah, sure.” But I had no idea what that even meant. I was just like, “I'm open to anything.”

What I found out it meant was basically just plugging each other's newsletters. They wrote their own line and I put it in mine. So I wrote, “If you love a good semi-spicy newsletter, subscribe to Deez Links and you get a daily-ish link to something gossip worthy happening in the media industry.” And that was it.

As soon as their newsletter went out, my inbox was just completely spammed and I got 400 sign-ups in one day from this. And I was like, this is really crazy. I didn't even know this community, this audience existed.

Get credibility

The third bucket of tactics is to get institutional cred. I mean that in very loose terms. One of the biggest things that worked out for Deez Links was when this email platform called Revue wanted to do a survey of the top media newsletters in the industry. It was a very unscientific poll. They were just reaching out to people in newsletters and saying “Hey, can you plug this poll? We just want everyone to take this survey.”

So I put it in my newsletter at the time and said, “Hey guys, if you like this newsletter could you vote for Deez Links in this survey?” I only did it because I thought maybe it would be really funny if we got in the running. But it turned out that enough of my subscribers voted for Deez Links that it showed up in the top five between America Press Institute and Digiday Media, really legit places.

When this came out I was like, “Oh my God, this makes us so legit.” And so again, people in industry were talking about it, there was a lot of buzz. A lot of people were like, “What is this one that I don't recognize? I'm going to Google it and subscribe and see what the deal is.” So when that came out I got about 200 subscribers.

Finally, the one that I'm most proud of is when Deez Links was named in Vanity Fair. I'm going to be totally candid and tell you it's because the editor who wrote this piece is a friend from college. When she was researching this piece, she talked to me and was like, “What do you think? What are some people that you think would be good to talk to?” And so I was like, “You should talk to the Substack people. You should totally mention these newsletters.” We just bounced ideas off each other. Then she just did me a hugely gracious favor and quoted me directly and included Deez Links in this piece about the state of newsletters. That was huge, because it felt like this vote of confidence. When this piece went out, I got around 200 or 300 subscribers and bragging rights forever.

I do want to acknowledge that there was a huge advantage in terms of starting my newsletter when I had a day job in media, and still do, and it automatically exposes me to this whole network of people with these followings and power, like the way the Vanity Fair writer had when she was writing this piece.

I also want to acknowledge that there is nothing that media people love talking about more than their own industry. So that also was a huge help. But nevertheless, I do think that no matter what industry your day job is in, no matter what your newsletter is about, it's a really good exercise to just think about, “Who is my intended audience? What do I think that they're listening to or reading now? And how can I find these middlemen or platforms that can serve as a megaphone for reaching this audience?”

Growing your subscriber base is like making friends

It's like when you move to a new city and you don't know anyone. You can go and try and meet people one-on-one, but it would take a long time. The better route is to call up your super-popular, super well-connected friend in the city and be like, “Hey, can you introduce me to all of your friends?” And they do, and that's just so much faster. You get exposed to these various communities a lot quicker, and you come with this vote of confidence from your popular friend.

It's cheesy to think about growing your subscriber base in terms of making friends, but I do think that it speaks to this very personal nature of newsletters. You're sliding to their inbox every morning, or every week, and your subscribers can just hit respond and tell you what they think. That's something really precious and beautiful. It does take longer to build up in ways that, say, maybe blogs were different. But I do think it's worth investing in those relationships, because once you become friends with these people, they’re there for you forever. They'll introduce you to their friends, and then your community just keeps on growing.

For more advice on growing your newsletter, check out how Sarah Noeckel's Femstreet went from zero to 5,000 subscribers.

Photo by Bess Adler

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We invited Emily Atkin, author of Heated, to talk to an audience of Substack writers in New York about how she successfully launched paid subscriptions. Emily left her job at The New Republic to start Heated, which offers original reporting and analysis on the climate crisis. Her newsletter is now her full-time job, bringing in six figures of revenue.

This transcript has been lightly edited for readability.

Takeaways

* Focus on building your free signup list first.

* Announce a paid launch date.

* Offer a discount for early birds.

* Every day during your launch week, give people a different reason to subscribe.

* A day before your first paid post, make a final pitch.

I write a newsletter called Heated. It’s been in existence for five months now, and it’s going well. It’s my full-time endeavor.

Being able to make a living off my writing has always been my dream since I was in college and I took my first journalism class. Eight years and a lot of failures later, Substack provided me with a platform to be able to succeed. It’s honestly allowed me to achieve my dream. I make more money now than I had at any salaried journalism job.

I make more money now than I had at any salaried journalism job.

I’m going to talk about how to grow your free newsletter into a paid newsletter. At this point, you’ll already have had a newsletter for a while. You’ll have enough subscribers that you think you can convert some to paying. You’re ready to go.

I’m going to share the tactics I used. You can adapt these however you like. I only launched my paid newsletter a little over two months ago, and I’m already in the six-figures range. I’m not a genius; I just followed a formula.

Make your newsletter free for as long as you can

Step one is to make a free newsletter, and make it original. Make it consistent. I think consistency is really important; that’s something I’ve heard from a lot of my subscribers. I have a little over 20,000 signups on my free list and a little over 2,000 on my paid list, including subscriptions I’ve given away.

Give your newsletter away for free for as long as you possibly can. Especially if it’s getting a lot of traction off the bat, and people are like, “I would like to pay you for this. Can I pay you for it?” Don’t let them. Hold on for as long as you possibly can, because almost all the paid subscriptions you’ll get will be conversions from your free list.

People don’t just sign up and pay. They want free content first, so they can decide if they want to pay. From my analysis, the average amount of time that people take to convert from free to the paid list is about a month, although I don't have much data yet.

Give your newsletter away for free for as long as you possibly can. People don’t just sign up and pay. They want free content first.

Foster your community. Make people want to pay for your stuff. Market your newsletter in a way that will almost make you uncomfortable, because it sounds like you're just talking and promoting yourself all the time.

Announce you’re going paid

So you've done all that, and you're ready to launch your paid subscription. Don't just put a paywall up. Give your readers at least a week's notice.

I write my newsletter four days a week, Monday through Thursday. So, two weeks before I put up a paywall, I said, “Okay, guys. Now's the time. It's been three months. Next week, I'm going to give you the ability to pay.”

I wrote that on the bottom of a Thursday newsletter, the last one of the week. I told my readers that I've written this newsletter for free because I wanted to demonstrate its value first. I said that next week, I’ll start accepting payments, and I'll announce the rates then, but it’ll still be free all of next week.

Once you turn on payments on Substack, the format changes. You unlock the ability to write preambles to your newsletter. That's where I did my marketing. I went personal on it. I was like, “Guys, I'm scared. I quit my job to do this. Please don't let me fail.”

That's another thing about newsletters. You can get personal. I did some positive marketing for this, too. I was like, “If this works, imagine how many more people we can reach; if I can hire a research assistant; if I had a copy editor...”

Kick off a paid launch week

The next week is your paid launch week, where you remind people every day that you’re going paid, but you still keep all your content free.

Make sure your content is really good all week. Put in extra work. Every day, in your preamble, try to give a different reason why people should subscribe.

Set your price high – higher than you’d think. During your paid launch week, offer a discount. I did 25% off the first two days and then 20% off the second two days so I could say, “All right, you missed 25% off, but you still have 20% off”. Then the price goes up from there.

For day one, I focused on a personal appeal and giving a discount. I made it feel like: “Today’s a special day, cue the air horn sounds!” Especially after you've been giving stuff away for three months, you've built up a community, so it should feel like, “Yay, now it's your turn.”

I made a personal appeal there that was, “I gave this to you for free, but it's not sustainable for me. I want to be able to do this every day. I want this to grow. I have so many aspirations for this. We, together, can make this a thing. Let's make it a thing.” People are like, “Yeah, let's make it a thing!”

I also do this thing where for every 100 people who sign up, I'll give 10 subscriptions away to people who need it. It helps. It's good because it helps grow your paid list, but it also gives your stuff to people who can't afford it. People are like, “Oh, okay, if I can afford it, I’d also like your writing to go to somebody else.”

For day two, I used the excitement from day one for momentum. You can send different emails to your free and paid list. So I sent an email to those who’d paid on day one that was like, “Guys, you signed up. Yes. Thank you so much. You're amazing.”

Then I sent an email to my free list that said, “If you're getting this message, that means you didn't sign up. How dare you? After all I've done for you.” But then I said, “This is the last day you can get 25% off, so you're going to want to do it today.”

Build upon your momentum from day one. Include quotes from people on Twitter who are signing up for your newsletter, even if it's just one of your friends.

For the next two days, experiment with different tactics. You know your community, so you’ll know best what would appeal to them.

For day three, I tried this messaging about how the fossil fuel industry poured billions of dollars into disinformation. My newsletter is about climate change, but it's specifically about powerful people and climate change. So for day three, I used that angle. I was like, “Let's combat this with information. Let's produce journalism that makes the truth louder than their lies. That can only happen with your support.”

On day four, I didn't do any marketing. I just did an ‘Ask Me Anything’ [AMA]. I used the discussion threads feature on Substack, which is a way to interact with your subscribers. On that day, people had a lot of questions about the paid launch, so I was able to go in there and answer their questions.

I did five newsletters this week instead of my usual four, because I just wanted more opportunities to promote my launch. I decided to make my last day something big, to demonstrate the value of this work that your money would buy.

On the last day, I launched a project I had been working on for a long time. I published a large anthology of fossil fuel advertisements. There was an embargoed study in there, some interviews, all this stuff. Instead of having my marketing preamble at the beginning, this time I did it at the end. I said, “This is an ongoing project. There's so much we're going to do, but it can only happen with your support.”

Make your final pitch

By the end of this week, you've asked people to pay you every single day. It’s now the weekend. Take a brea…

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit on.substack.com