Founder Brand with Finn Thormeier

If you ever wondered if you can have fun on Linkedin AND still make it a major revenue channel for your startup, the answer is, surprisingly… yes.

Hendrik Ojamaa is the co-founder of Jungler, a GTM tool that tracks signals. He started posting in February, but it’s almost all parody content and shitposts. Today, about 8 months later, he added 10k followers, gets about 1.2m impressions a month, and drives roughly 200 free trial signups for his product from it every month.

In this episode, we we break it all down, how he does it, why he does it, why it works, so you can hopefully take a piece from it and make your own Linkedin a bit less serious and a bit more fun.

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We discuss:

* The viral cold email post that drove 100 signups over night and inspired Hendrik to get started with parody content

* How to go viral more often

* How to tie parody content to the product AFTER you’ve figured out virality *within your ICP*

* Why not all virality is created equal

* Why tagging your company is weak for driving signups, and the “PS” line that works instead

* How to be more funny

* Lessons from Matt Firestone, James Hawkins, Renée Shaw, and The Onion

* How to write 5 Linkedin posts in 2 hours: Hendrik’s process and the 50-line Google Doc behind it

* Example posts that drove the most signups

* Coping with: Will parody make your buyers & investors not take you seriously?

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SaaS & AI Founders: Want to grow faster on LinkedIn?

Thormeier.co is my LinkedIn & Founder Brand advisory where I’ve helped 30+ SaaS and AI founders grow faster on LinkedIn, build a stronger founder brand, and drive more pipeline from it.

If you want to get unblocked, book a workshop here.

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Show Notes:

Connect with Hendrik Ojamaa:

Hendrik Ojamaa’s LinkedIn: https://www.linkedin.com/in/junglerhendrik/

Jungler: https://www.jungler.ai/

Connect with Finn Thormeier:

Finn’s LinkedIn: https://www.linkedin.com/in/finnthormeier/

Thormeier.co - Founder Brand & LinkedIn Advisory: https://thormeier.co/

Mentioned in the episode:

Matt Firestone’s LinkedIn: https://www.linkedin.com/in/mfirestone1/

James Hawkins’ LinkedIn (PostHog CEO): https://www.linkedin.com/in/j-hawkins

How to Write Funny by Scott Dikkers: https://howtowritefunny.com/

The Onion: https://theonion.com/

Renée Shaw’s LinkedIn: https://www.linkedin.com/in/reneeeshaw/

Torq (Don Jeter, CMO): https://torq.io/

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Dave Kellogg is a consultant, startup advisor, and founder of Kellblog.com. He built one of the most senior audiences I’ve ever seen, which is why I’ve been wanting to have him on the show for a loooong time (thanks for the intro Tom Wentworth).

Before starting his consulting career in 2019, Dave spent over 30 years in various executive roles at enterprise software companies: CEO at Planful (then Host Analytics), SVP / GM of the $500m Service Cloud business at Salesforce, CEO of MarkLogic, and CMO at Business Objects as they grew from $30M to over $1B in revenues. He’s currently an EIR at Balderton Capital and sits on the board of various tech startups

Throughout all of this, Dave built one of the most respected executive brands in B2B software, which is what we talk about in this episode: the lessons, mistakes, and stories.

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We discuss:

* The story of Kellblog: how it started, how it’s going

* The meeting with Ben Horowitz that made Dave never “write for the algorithm” ever again

* How to build an audience of very senior executives

* Why most thought leadership isn’t

* Dave’s definition of branding (as it applies to executive/founder branding)

* How he writes: note files, outlines, AI

* Lessons on voice using Jack Daniel’s “Postcards from Lynchburg” as an example

* How to get the word out in a world of “walled gardens”: blog vs LinkedIn vs X vs newsletter

* Why chasing 100k followers would cost him the audience he has (quality vs quantity)

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SaaS & AI Founders: Want to grow faster on LinkedIn?

Thormeier.co is my LinkedIn & Founder Brand advisory where I’ve helped 30+ SaaS and AI founders grow faster on LinkedIn, build a stronger founder brand, and drive more pipeline from it.

If you want to get unblocked, book a workshop here.

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Show Notes:

Connect with Dave Kellogg:

Dave Kellogg’s LinkedIn: https://www.linkedin.com/in/kelloggdave/

Kellblog: https://www.kellblog.com/

The Metrics Brothers podcast: https://podcasts.apple.com/us/podcast/the-metrics-brothers/id1687214133

Balderton Capital: https://www.balderton.com/

Connect with Finn:

Finn’s LinkedIn: https://www.linkedin.com/in/finnthormeier

Founder Brand & LinkedIn Advisory: https://thormeier.co/

Mentioned in the episode:

Obviously Awesome by April Dunford: https://www.aprildunford.com/books

The Men That Don’t Fit In by Robert Service: https://www.poetryfoundation.org/poems/58012/the-men-that-dont-fit-in

The GitLab Handbook: https://handbook.gitlab.com/

Planful: https://planful.com/

MarkLogic: https://www.progress.com/marklogic

Pigment: https://www.pigment.com/

Ghost: https://ghost.org/

The Diary of a CEO: https://stevenbartlett.com/doac/

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Work with me: https://thormeier.co/

I help SaaS / AI founders grow faster on LinkedIn, build a stronger founder brand, and drive more revenue from it.

Track record / why I have the audacity to teach this stuff:

1. Grew my LinkedIn to 43,000 followers

2. Which to date has generated about $3.2m in revenue for myself

3. Built a LinkedIn ghostwriting agency (Project 33) to 7 people and $100k/month, where we worked with over 80 B2B tech companies

4. Closed the agency to advise founders and make the same amount of money with no employees. I advised now over 30 founders on how to grow on LinkedIn, including the CEO of a publicly-traded cybersecurity company

5. I run the biggest podcast and newsletter in this space (founderbrand.org)

6. I've interviewed over 150 of the biggest founder brands about their approach, including Jason Fried, DHH, Henry Schuck, Dave Gerhardt, Guillaume Moubeche, Adam Robinson

7. Spoke on stages about this stuff, eg. at Nathan Latka's SaaSOpen

Will be doing more of these in-depth breakdowns on content and founder brand, even installed some new tools to make them more tactical and hopefully useful to you guys.

Summary / TLDR:

* He changed from doing solo videos of just him teaching business owners how to scale their company (by sharing a tip, strategy, story, lesson) → to bringing on a real business owner, having them present their business (revenue, growth, where they’re stuck) and then basically doing a 1:1 consulting session where Alex gives them very tactical advice on how to scale their company.

* His main offer: a $5k in-person group workshop, which his company Acquisition.com hosts once a week with 70-100 business owners, where he upsells about 30% attendees into a $36k/year advisory program.

* The math: 70 x $5k = $350k per event for just the workshop tickets, which is $1.4M per month, given that they do it every week. Upsells: 20 x $36k = roughly $700k per event from the upsells, which is $2.8M per month, so $4.2M per month or roughly $50M per year in total for just the advisory business, not including their PE portfolio etc.

* His new style of video is hyper optimized to drive workshop ticket sales. Gotta watch the above video why. But a few notes:

* It’s just good content because it’s hyper tactical, which is what most business owners want

* It’s gamified, because they structure it like a game show, so you get emotionally involved and are more likely to watch the next video because there is continuity

* It not only shows that Alex knows how to scale businesses using his own businesses as examples, but that he ALSO knows how to coach other business owner into scaling THEIRS, which is exactly what you want to know before hiring someone as your advisor

* The winner of the “game show” is a perfect match for becoming a portfolio company of their PE arm, so all of it combined is also deal flow and filtering for them

Full Transcript:

[0:00] Alex Hormozi recently changed his content strategy, and I think it’s brilliant, but I think most people will miss it or not really notice how smart this actually is. So I wanted to break it down a little bit.

So most of his videos were just like this. It was like a 15-minute, sometimes much longer, video of just him teaching stuff. And then recently they started doing this, basically like a game show. They call it Scale or Fail. The first round of it was basically these videos where he would sit down with a business owner, and they would present their business and what they’re struggling with: revenue, growth, et cetera. And then they would have basically a one-on-one consulting session with Alex, where he would give them very specific technical advice for their business. So there were different kinds of businesses, like a theme park. I think this is a dentist or something. This is a service business, a roofer. And he would basically coach them.

[0:58] That was basically phase one. And then the best people moved on to this most recent show that they did a couple of days ago, where they basically all presented how they implemented the advice that he gave them and how much they grew. And then the people who grew the most advanced to the next stage, and from there it would progress.

[1:20] I don’t think people realize how much money he’s printing with this content. But if you look at some of the psychology, I think it’s super, super smart. So let me share some things.

[1:38] The way that Alex Hormozi makes money: obviously he owns a company called ACQ, and they have a couple of different offers. The first one is an in-person workshop that they sell for 5K. That’s a workshop. Two days. And it’s in person, at their office. That’s kind of the entry offer, right?

[2:01] Then from there, the upsell is they sell a 36K, which is basically their advisory, per year. So you pay this upfront for the full year. And this is basically a way you get access to Alex’s team, and you can ask them any question at any point. There’s a community. Alex does, I think, monthly Q&As where you can ask him questions.

[2:26] And then, I believe the main thing, and this is how he mainly started, was basically a PE firm, where they would own... I don’t know if this is disclosed. I believe it’s somewhere between 10 to 50% of companies that they own, and that’s the profit share that they get. So for the best, biggest, most profitable, fastest growing companies, they basically act like a PE firm. They get a stake in it, and from that they get a profit share.

[2:55] And so this is what he wants to sell, and then from there there’s the upsell, and then from there this basically funnels the absolute best companies, who want to get real one-on-one ongoing access to Alex, right?

[3:07] And so his YouTube channel obviously funnels people there. If you look at any of his videos, and this is more like the old style, “What type of content should you make that makes the most money”, him sitting down, sharing some advice, “How to become rich with social media”, the call to action is always to their lead magnet. So it’s basically a lead magnet. You get your free personalized roadmap, you put in your information, and you get it sent to your email.

[3:41] From there, once you get that lead magnet, the next pitch is basically: hey, if you like this resource and you want to scale your company, here you can sign up for the workshop. And their landing page is basically... if you go to acquisition.com right now, it’s the workshop landing page, with a little VSL here, “I’m ready to scale”, some testimonials, what you actually get at the workshop, more testimonials, and then a call booking form to attend the workshop. And they’re also explicit here that it’s 5K per seat. I actually attended one of these. So this is their entry monetized offer, right?

[4:27] Also, sometimes, I believe, if you look at his podcast, they directly lead you to the workshop landing page as the main CTA. This is the roadmap, roadmap, roadmap, roadmap. Here, you can see for this podcast, instead of it being the free lead magnet, the roadmap, the call to action is directly “book your spot at the two-day interactive scaling workshop”. So they’re experimenting with that.

[4:57] And I think what people are also not realizing is how much money they’re printing with this. Because it’s 5K per ticket. It’s a group workshop, right? They have about a hundred business owners there, 100 attendees at each of these workshops, in person. I would say not all of them are paid, because when you’re part of the community of the upsell, you get two of these every year for free. So let’s say 70 of these actually paid. So that is 70 times 5K, they’re making 350K per event. And they do them once per week, which means they make 1.4 million per month from just these workshops.

[5:55] But now it gets even better. So they have the 1.4 million per month from the workshops. But then at the workshop they do the upsell to the 36K advisory. And I know that they upsell roughly a third of people, so 25 to 33% of people do the upsell. So of the 70 people, let’s say, who are not yet part of the program and who actually paid at the event, a third of them buy the upsell. So let’s be conservative here and say 20 buy the upsell. 20 times 36K, what is that? That’s [720K]? That is another 700K per event. Again, they do four events every month, one per week. So this times four is, they’re making another 2.8 million per month in upsells.

[7:02] So that together is, they’re making 4.2 million per month from the workshop plus upsells, which is what? 48, like roughly 50 million. Yeah. That’s crazy. I mean, none of these numbers are confirmed. This is just me doing the math from other numbers that I know and inferring. Maybe it’s more, maybe it’s less, but this is, I think, a good ballpark number of what they’re making just from this.

[7:27] And then obviously here, the upsell is that once someone does the yearly advisory, and the company is doing really, really well, and they’re growing fast, and they’re very profitable, and they want more access to Alex, and they want Alex to sit on their board or get weekly one-on-one calls with Alex, then from there they become part of the portfolio. And then from there they get a profit share, right? And when I was at the workshop two months ago, I think the biggest company that was at the workshop was doing 40 million in revenue. So these are not just tiny, tiny companies.

[8:10] So it’s printing money. But back to the content strategy, right? What he’s optimizing for with this YouTube and podcast (they’re very overlapping, he repurposes a lot of content between those two) is how to get more people to buy the 5K workshop, ‘cause that’s the main offer that they sell. And he needs to fill anywhere between 70 to 100 slots every week, which is, let’s say, 400 slots per month he needs to sell. And so that’s what his content strategy is laid out for.

[8:50] So if we go back to his YouTube channel, here it is. If you think about the psychology of the videos that he’s putting out: the workshop is essentially a scaling workshop, right? That’s how it’s positioned. Like, hey, you’re a business owner, you’re stuck somewhere, you want to double your revenue. Come and attend the workshop, work with my team, and we’ll help you get unstuck and figure out where your bottleneck is and how you can scale your company more.

[9:17] All of his content always, even previously, these sit-down videos with just him, they’re aimed at business owners. And they’re always aimed at helping them grow their company in some way, by sharing some framework, some tips, some roadmaps, some lesson that he learned: how to sell better, how to build better offers, how to do marketing better, how to run better ads. All of that is to serve their goal of growing their company. And so you get a business owner to watch the video, and then at the end the call to action is basically: hey, you now learned some small way of how to grow your company. If you want to grow your company even more, and, you know, trust me, because you watched the video and you saw that I have smart things to say, go and attend a workshop with us, right?

[9:55] Now, this new format is, I think, that on steroids. He’s basically sitting down with a business owner and advising him or her one-on-one on exactly how they grow their company. And I think it’s so good for multiple reasons.

[10:14] The first reason is that it’s just good content. If you’re a business owner, you actually want hyper tactical stuff. I think tactical especially, the better and bigger you get as a company. You don’t need this kind of generic, like, “oh, cold email is dead, you need to do organic content”, or here’s some philosophical take on how you need to approach your company. You want hyper tactical insights on the exact little things that you need to adjust in your business. So it’s super, super tactical, and it’s essentially a game show.

[10:56] So not only is it super interesting and relevant content for exactly his audience that he’s looking to attract, but you have this kind of gamification in there. Because instead of just hearing Alex Hormozi speak and share his advice, there’s also this element of, you know, you get involved a little bit. Some of these episodes are quite emotional. Like, if I go to some of these, like this guy here, he runs a theme park [clip from the episode plays], he gave up his 401k and poured it into the business to try to save it. You know, he gets emotional here. So with some of these business owners, you get really emotionally involved.

[11:44] But this is also the game show aspect. So you have emotional involvement. But then you also start rooting for people. You have your kind of favorites who you want to advance in the game, who you want to get to the next round, and who you maybe want to not get to the next round because you don’t like them. And so you have this kind of involvement, and you also have an ongoing series, which helps with retention, right? Because instead of just having a good video, that was good, and so you subscribe to the channel because you want to get more good videos, there’s an element of, like, oh, I want to see what happens next, because I want to follow along the journey of whether this person progresses or not, and who gets eliminated in the next show, et cetera, right?

[12:27] So it’s just good content. That’s number one, and that’s the good reason why it’s just working. But I think it’s better for more reasons than that, because I think this is the kind of relatively obvious stuff.

[12:42] If you think about the psychology of the thing that he’s selling, which is the workshop and then the advisory, which is essentially a coach, right? If you’re gonna hire an advisor or coach, you wanna know two things. Number one, they know their stuff. But number two, you wanna know that they’re a good coach. Because if you’re going to play football, of course it’s going to help if the person who’s training you, and who you go to for advice, was a good football player who played in a big league and who had success, right? That builds credibility, and you’re like, oh, I want to learn from that person. But not every single football player who is a good football player is also a good coach, right? That’s a separate skill, to be able to teach people and pinpoint their exact weaknesses, et cetera.

[13:36] And so his previous videos were basically just him demonstrating that he knows how to scale businesses, right? Because he talks about his lessons, his advice, his insights, what he’s done before, stories from his past. So you’re like, okay, this guy actually knows business and has done good things. But if you’re gonna hire his firm and his company and him to advise you, you also wanna know: is he actually able to help me specifically, and sit down with me and figure out my specifics for my specific business, and then give me technical advice that I can use, and not just do this for his own companies, right? And so this new format demonstrates this very, very clearly. So I think it drives even more interest for the specific offer that they run, which is a workshop slash advisory.

[14:22] Because he essentially does that in the video, right? What you’re watching is a one-on-one advisory coaching session that he does with a business owner, and that’s the exact thing that you would want to buy. So it’s the best possible thing to advertise the thing that you’re selling. So, again, I don’t have access to any of the backend numbers, but I’m very confident that the conversion rate of views to workshop bookings is much higher, because it’s a much more natural conversion path, right? You have a business owner, which is your audience. You have a video that is super relevant and interesting to them, which is tactical advice for another business owner on how to scale their company. It’s also gamified, so you’re more engaged and more likely to come back. But then what you sell is advisory and basically coaching. So it’s a direct conversion path.

[15:11] But I think where it gets even more brilliant is... and this already is the less obvious part that I think many people don’t think about when they create their content, which is that you don’t just need content that is relevant to your audience, right? If you create content, you have your ICP, and obviously your content needs to be relevant and interesting to your ICP, because otherwise you’re not going to attract your ICP. And how are you going to sell anything if the people who watch your content are not the same people who buy your product or service, right? So this needs to align, and you do that by talking about their problems, goals, desires. And that’s how you attract them, which is what Alex does, right? His ICP is business owners. What do they care about? They want to scale their business. What are their desires? They want to make a ton of money. They want to double their revenue. They don’t know what ads to run or how to scale a sales team. So all of his content addresses all of these things, and that’s how he attracts people.

[16:19] Beyond that, what you need to do is that the problems and goals and desires that you speak to need to also be the ones that your product actually solves, right? Which seems obvious, but so many people don’t do that. Let’s say, again, my ICP is SaaS founders. So if I want to attract them with my content, I need to talk about their goals, problems, desires. But what are SaaS founders’ goals, problems and desires? There’s a ton of stuff, right? Fundraising: how do I raise my next round? There’s sales: how do I hire a sales team, how do I train my sales team, how do I do outbound? There’s marketing: how do I get awareness, or grow pipeline, or get more leads? There’s obviously HR and hiring: how do I hire and find great people and retain them? There’s operations, which is: how do I reduce my costs and improve margins, how do I build better processes, how do I leverage AI? There’s a ton of stuff. So I could speak to any of these, and it would help me attract these people with my content. But I only do one thing, which is LinkedIn and founder brand advisory. That’s the only thing I do.

[17:41] And so if I create a piece of content around “how do you leverage AI to optimize your processes and improve margins”, that might be interesting to them, but then there is no natural path to be like, “and by the way, I help people with LinkedIn and their founder brand”, because it’s not what they signed up for, it’s not what they watch me for. But where it does help is marketing, right? So if they’re struggling with how to get awareness, or how to get leads, or how to drive more pipeline with enterprise buyers, this is directly what this impacts. And so if I create content that speaks to this problem, and then presents it in a way that has to do with founder brand or LinkedIn or both, then that’s a much more natural path to then be like: “and by the way, if you found this piece of content interesting and the solution makes sense for you, then you might wanna check out what I do, because I can help you do it better and faster.”

[18:31] Which is probably what this video is, right? I speak to founders, I talk about the marketing aspect, and it’s very connected to founder brand, because it’s Alex, it’s him running it as a founder. It’s definitely not LinkedIn, this is mainly YouTube, but it’s very much organic content related. So there’s a much more natural path for me to say in this video: hey, and if this resonated with you and you want to figure out how to apply all of this to your business and your founder brand and your content, go reach out to me so I can help you.

[18:59] But I think there’s more. Because, yes, he’s creating good content that is relevant to his audience, and it’s super tactical, and there’s this game show aspect. But as I started thinking about it [a few words unclear]. There’s another super brilliant aspect of this, because they run it as a game show, right? So they now have eight of these contestants who he did the advisory session with first, and now they basically show off what they implemented and how much they grew. At some point they actually go over how much revenue they added in the 90 days after they had their one-on-one session with Alex, right? This person added 920,000 in top-line revenue. This person added 500K. This person added 1.6 million in top-line revenue in the 90 days since the advisory session.

[19:54] And so this is a prediction, because this is their most recent video, from five days ago. But my prediction is that at the end of this thing they’re obviously going to have a winner of the show, of the Scale or Fail show, which is why it’s a game show. That’s part of it, that’s why you start rooting for people. And that winner wins a golden ticket, they say, to work with Alex’s firm, which seems like a perk to the viewers, right? It’s like a promise: if you win, then you get to work with me. I’m pretty sure that whoever’s the winner, the golden ticket means you become a portfolio company, where they probably invest some amount of money into you, and then Acquisition.com and Alex get a profit share.

[20:50] And why is this so brilliant? Because it’s basically deal flow that they’re generating here, right? It’s a funnel. They get applications from people who want to participate in this game, who are all business owners, and they want to scale their business, and they look up to Alex Hormozi and they wanna learn from him. That’s why they apply. Then they pick the best ones of them, do the YouTube video with them, which creates this incredible content. And then, as people go through this process, they see how well they execute, how coachable they are, and they get an inside look into the company metrics, right? Because part of this is them sharing how much revenue they’re making, and how much profit they’re making, and how quickly they’re growing.

[21:50] And so whoever wins at the end is the winner of the show, but they’re also the most perfect fit for the portfolio. They want to learn from Alex. They’ve demonstrated that they can execute well, that they’re coachable, and they’ve demonstrated that the company is doing super well, that they’ve been able to grow it super fast, that it’s super profitable. And so this is what they want for a portfolio company, right? And so it’s a win-win at the end for both: the business owner gets even more access to Alex and gets this continuous coaching and advice, and they found a perfect portfolio company here, that is growing fast, with a founder that listens to advice and implements it quickly and is demonstrably growing revenue by a lot through it.

[22:39] Just think about what that would mean for your company, right? That would mean that you invite your ICPs. Let’s say you sell to enterprise VPs of engineering. Imagine you would be able to invite VPs of engineering who are not yet your customers, and create content with them that they find valuable, that other enterprise VPs of engineering find interesting. So it’s great content that helps you with your awareness and top of funnel, that generates leads for your company that sells to VPs of engineering. But through the process of creating this content with them, you end up with people who become direct buyers of your product by winning the show.

[23:24] And I don’t think this is random, right? I think this is an evolution of how they arrived at that. And if I had to guess how they arrived at this strategy, because it’s a lot of planning and production and getting this right, you can see gradually how they learned that this is the best format for them right now, right? They were doing these just-Alex sit-down videos, what he teaches. And then at some point they did a lot of these videos, I think it’s on this other channel, where basically they would do these Q&A clips of people who attended the workshop. Right, this is at the workshop. This is Alex at the workshop, and then this is a person who is attending the workshop, and they do a Q&A, and they would just record the Q&A and put up that video. And that content did really well.

[24:24] And then they said, okay, how can we do this better and scale it? Increase the production. So they started experimenting with this format seven months ago. You can see this is the same format. This is another video like that, eight months ago, where they had the same format: business owners come, present their business, and get a one-on-one advisory session with Alex. But it was just one-off things. And I’m pretty sure they learned that, oh my God, this... And so they’re like, first of all, how can we do this way more, instead of once a month sporadically, and make it an actual thing that we do? And then they figured out this kind of gamification, to not just do a one-off advisory session with a business owner and then peace out and never see them again, but rather make this like a progression, like a game show, where the best people progress into the next round. Here’s another one: progress into the next round. And then the winner wins the golden ticket to become a portfolio company.

[25:19] Lots of good things here. I think if I try to summarize the lessons here: you need to create content for your ICP (this is obvious) that you can tie directly to what you sell. Meaning your product or service should be a natural progression from the piece of content. So if Alex talks to a business owner about how to scale their company, it’s a natural progression to say: and if you want to scale your company more and even better, and work with us directly, attend the workshop. So you want to tie it directly to what you sell.

[26:04] I mean, if you can somehow gamify it, obviously that is amazing, and have a kind of game show continuity in there, like a progression. And they basically engineered it so that the winner of the game show is also the best-match enterprise deal. Because a portfolio company is basically like an enterprise deal for them. It’s a super long process, it’s a super low probability that someone is a fit, but if someone is a fit, it’s a very high upside.

[26:50] And so I think it’s just brilliant, and there’s a lot to learn from it, and from the constant iteration and progression that you can see in this content. Hope it was useful. If it was, you know, unsurprisingly, as I said, I do this sort of stuff. For SaaS and AI founders, I have an advisory. It’s mostly LinkedIn stuff, and how I help people do similar stuff, but on their LinkedIn: how to create better content and how to drive more revenue from it. So if that’s relevant, book a call with me. If not, I hope this piece of content was valuable.

David Fallarme is the VP Marketing at Owner.com (Series D, valued at $2.3B), an AI platform for restaurant owners. Before Owner.com, he ran marketing for Asia at HubSpot.

Owner.com built one of the most prominent founder brands and Youtube channels in B2B. They invested $1m into brand when they were still doing only $10m in ARR (now doing over $100m), resulting in 27M impressions last year, with organic generating 20% of pipeline every month.

In this episode, we talk about their approach to Youtube and leveraging the founder brand early.

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We discuss:

* How to crush Youtube as a B2B company

* The #1 mistake B2B companies make when they try to leverage Youtube

* First order irrational, second order rational: why Owner.com invests so much into brand

* How and why Owner.com CEO Adam Guild spent 10 hours every Saturday to produce videos

* Variables to success and comparing 2 videos: same title and thumbnail, one with 100k views, the other with 3.4k views (30x less)

* Brand strategy into topics into script flow

* The 5 stages of building an organic motion from scratch

* Why a great Youtube editor is worth 10-100x a good one (they pay $120-150k to people straight out of college)

* David’s advice for founders who want to build their founder brand

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Show Notes:

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Connect with David Fallarme:

David Fallarme's LinkedIn: https://www.linkedin.com/in/dfallarme/

Owner.com: https://www.owner.com/

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Connect with Finn:

Finn's LinkedIn: https://www.linkedin.com/in/finnthormeier/

Founder Brand & LinkedIn Advisory: https://thormeier.co/

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Mentioned in the episode:

Owner.com’s Youtube Channel: https://www.youtube.com/@owner-com/

Ahrefs’ Youtube Channel: https://www.youtube.com/@AhrefsCom

Owner.com Founder Adam Guild: https://www.linkedin.com/in/adamharrisonguild/

In-N-Out video: https://www.youtube.com/watch?v=gbx8EG9I0tY

Five Guys video: https://www.youtube.com/watch?v=LQnNJF79psk

NotebookLM: https://notebooklm.google/

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Jillian Richardson is a Linkedin ghostwriter and runs “Make LinkedIn Weird”. Before degenerating into Linkedin work (I’m allowed to say this because I do Linkedin work), she did standup comedy and 6 years of improv training, which is where she gets her inspiration from.

In this episode, we talk about why you should be weirder on Linkedin, how to find your flavor of weird, whether you can say the word F**K on Linkedin, and more. This one’s for you if you feel like your writing is too boring or you’re not able to get your full personality on paper.

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We discuss:

* Why “Linkedin is the fakest place on earth” is the best news for anyone willing to be weird

* The benefits of allowing yourself to be weirder

* How to find your flavor of weird

* Jillian’s envy-disgust matrix

* The three-pass editing routine (this one was eye-opening to me!!)

* Can you say f**k on Linkedin? Should you?

* How to become funnier

---

This post is sponsored by Thormeier.co

Thormeier.co is my LinkedIn & Founder Brand advisory where I’ve worked with 30+ SaaS and AI founders grow faster on LinkedIn, build a stronger founder brand, and drive more pipeline from it.

If you want to understand how I work with founders, book a call here.

---

Show Notes:

Connect with Jillian:

Jillian’s LinkedIn: https://www.linkedin.com/in/thatjillian/

Make LinkedIn Weird: https://www.makelinkedinweird.com/

Jillian’s website: https://www.thatjillian.com/

Connect with Finn:

Finn’s LinkedIn: https://www.linkedin.com/in/finnthormeier/

Thormeier.co - Founder Brand & LinkedIn Advisory: https://thormeier.co/

Mentioned in the episode:

Upright Citizens Brigade Comedy Improvisation Manual: https://ucbcomedy.com/product/upright-citizens-brigade-comedy-improvisation-manual/

The Artist’s Way by Julia Cameron: https://juliacameronlive.com/register/the-artists-way/

The Writing Life by Annie Dillard: https://www.anniedillard.com/books-annie-dillard.html

Kait LeDonne: https://www.linkedin.com/in/kaitledonne-personalbrandingexpert/

Matt Barker: https://www.linkedin.com/in/mattjbarker1/

Jasmin Alić: https://www.linkedin.com/in/alicjasmin/

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Full Transcript:

Finn Thormeier: All right, my guest today is Jillian Richardson. She is a ghostwriter for solopreneurs and executives, and she helps people be weirdo on LinkedIn, which I love. I think much needed. The platform can use it. Her message resonated with me. I found you like a couple weeks ago on LinkedIn for the first time, stumbled upon my feed. So I wanted to have her on to learn from her and maybe get a free consultation for all of us here. So Jillian, thank you for joining the pod.

Jillian Richardson: Thank you so much for having me.

Finn Thormeier: Cool. Let’s maybe start with making the case for why people should be weird on LinkedIn.

Jillian Richardson: Okay, so I’m someone, I go to a lot of dinner parties, a lot of places where I meet new people, and I say, you know, I’m a ghostwriter for LinkedIn, and the faces... It’s very telling of, I think, what LinkedIn’s brand is in the world. Like people are like, oh, LinkedIn, like LinkedIn is horrible. It’s so fake. It’s everyone just talking about how accomplished they are and their career milestones. And it’s just the fakest place on earth.

Finn Thormeier: LinkedIn invented slop before AI slop were the thing.

Jillian Richardson: Yes. Like even before AI, it was slop. Why would you ever want to write content for that platform? And so then I get to say to them, well, imagine if you didn’t fit into that mold, how happy people would be to see your content because the bar on LinkedIn is not very high and there’s so much room for creativity and humor and personal stories. And it’s pretty easy to make yourself stand out if you actually have a point of view and you have a little bit of fun with it. So that’s my case for it. Everyone knows LinkedIn doesn’t have the best reputation. And so if you can make it a little bit fun for people who are slogging through LinkedIn, trying to get a job, make a business contact, whatever, they will love you and they will remember you.

Finn Thormeier: Is it fair to say that being weirder on LinkedIn is the same thing as showing your personality?

Jillian Richardson: Yeah, I would say so. I think being weird, showing your personality, I say because I teach a class on this, it doesn’t mean you have to be posting memes every day or only telling jokes. I think everyone has their own brand of what I call weird, but it’s really just your personality. And so it might be sharing takes in your industry that a lot of people disagree with, sharing stuff about your personal life that you’re comfortable sharing, sharing hard moments in your business. But for whatever reason, the framing of weird seems to help people think about things in a new way. Yeah.

Finn Thormeier: And I mean, I would say it comes at a time where it’s most needed for the platform because there is so much AI. I think LinkedIn just won the award of the platform that has the most AI slop

Jillian Richardson: on it. Wait, what do you mean? I didn’t hear this.

Finn Thormeier: Yeah, I think someone published, I think it was some major publication that did an analysis and it was like 43% of all of LinkedIn posts was categorized as AI slop. However, that was being categorized and it was the highest compared to X and Instagram and Substack and all the other platforms. But I think having a personality, showing your personality, being willing to show up the way that you are, maybe not fully, but more so, has always worked. But now, given that there’s so much AI-generated content, which I think, one, means there’s just a lot more content and a lot of the content just looks and sounds the same, just because everyone basically has the same ghostwriter now.

Jillian Richardson: Yep.

Finn Thormeier: I guess that’s why it’s even more needed right now versus, I don’t know, two or three years ago.

Jillian Richardson: A hundred percent. And the thing on AI, I don’t know if you saw that there’s now a new button on LinkedIn. It sounds like AI slop, which is fascinating that LinkedIn decided to add that to the platform. Like three weeks ago, they had an AI rewrite feature, but, uh, If people are going to use some sort of ghostwriting tool, now that there’s that button, you have even more of a reason to work with a human ghostwriter.

Finn Thormeier: It’s almost like signaling to everyone, but just having one weird sentence in there that’s like, this is really me. I actually wrote this.

Jillian Richardson: Yes. A person wrote this.

Finn Thormeier: Now, um, you also, I think on your website, you list kind of some benefits of being weirder.

Jillian Richardson: Yeah.

Finn Thormeier: What are some of the benefits of showing up weirder?

Jillian Richardson: So honestly, the biggest one I would say is that the more fun you have with your writing, the more you are likely to actually show up because so many people ha it’s kind of like with exercise. If you do a form of exercise that you super, super, super hate. You’re going to be less likely to go to the gym than, you know, if you sign up for a Zumba class and you’re like, oh, I love Zumba and I have all my friends there and it’s my favorite part of the week. So if you can actually see it as a creative writing exercise, a way to get to know yourself, a way to get to know the world, then you’ll show up and you’ll do it more. And consistency is what builds a social media presence.

Finn Thormeier: Okay. And I guess it’s, I mean, that’s one of the benefits, consistency. I mean, the other benefit I feel like is, and again, feel free to talk to other ones, but if this is actually you, you just have stronger bonds with people, with your audience, right? Because it’s...

Jillian Richardson: I totally agree with that. Because there’s this bizarre thing on LinkedIn where... People will hire a ghostwriter and then they’ll get some sort of AI commenting tool that’s like commenting and also in their DMs. And then I’ve heard this from a lot of people I work with. They have this bizarre experience of feeling like they know a person and then they get on Zoom and they’re like, wait, this person doesn’t seem at all like the person I was interacting with. Was I even interacting with the person at all? And a lot of the times it turns out that they literally weren’t. And what a terrible way to interact with your customer, that their first impression of you is, actually, I don’t know you at all.

Finn Thormeier: Yeah. Well, it can also, I mean, it goes both ways. I think oftentimes people will realize if you don’t allow yourself to show that weird or Weird side of you or that personality of yourself that on the call they’ll be like, you’re actually more interesting than I thought. Yes.

Jillian Richardson: That’s a great point as well. That’s a good flip side of, oh, actually I enjoyed talking to you more than I thought I would.

Finn Thormeier: Yeah. No broetry. You don’t speak in one line sentences.

Jillian Richardson: Yeah. Yeah.

Finn Thormeier: Okay. I want to show, do you have a favorite example of a weird person? Post or being weird on LinkedIn. I’m going to share my screen here. I’ll just show one here. So like one example, let me make this big. Do you just see my LinkedIn now?

Jillian Richardson: Yes, I can see it. This is my like pièce de résistance.

Finn Thormeier: Exactly. Yeah. So this is kind of, it’s a good example of a weird post because it’s also your post where you make the case that people should be weird. This is the post how I found you. It started with, I am on my knees begging, be weird on LinkedIn, 10% weird, 100% weird if you had a good breakfast. It’s already clear that this post has personality. This is a hook that no one would use on LinkedIn. It’s a very bold choice to start a sentence like that and no one sees that on LinkedIn. Then also it’s like, there’s a joke here. Take that Claude, there’s personality in it, right? And I think if people just scroll through your LinkedIn a little bit, they’ll get a sense of what it means To write with personality. Break it in half and shove it into a deep grave for eternity. Like you write with color. You say things that people would say. Relax your butthole. It’s like on your banner, right? It’s like you’re almost breaking the rules of what is appropriate to say on LinkedIn, which is part of why it works. So I think this is a... Good example here. Okay, now let’s talk about how to become weirder because my assumption is there’s all kinds of different weird. So when you work with people, how do you coach them through figuring out what their flavor of weird is, how they can bring that out? And maybe use me as an example. If that’s somehow helpful, but I’m just curious how you coach people through that.

Jillian Richardson: Yeah, so when I start working with ghostwriting clients, we do what I call a LinkedIn sample pack. And so it’s essentially, I create a content strategy for them and then I write three LinkedIn posts for them so they can get a sense of, One, help them figure out what is their voice, but also do they even like the process of working with the ghostwriter? Because some people really think that they will, and then someone writes for them and they’re like, actually, I hate this so much. And part of that is figuring out who on LinkedIn or on the internet in general, do you see their content and you like their voice, you like the way they speak, you like what they stand for. And then probably more importantly, Whose content do they see online? And it kind of grosses them out. Like the exercise I do is the envy disgust matrix of like whose content are you jealous of? Which is indicative of you might want to move more towards that direction. Like they have something that maybe you’re a little afraid to do, but you want to do. And then whose content you see and you’re like, oh, like if I posted that, I would jump out a window and never return. Gives you the ick. Yeah, like it gives you the ick. That is an incredible indicator of what your voice is because you’re like, this is the line I do not cross. That’s super helpful information to know. And sometimes you don’t know that until you see something you don’t want or somebody writes something for you and you’re like, this isn’t it actually. Okay.

Finn Thormeier: So envy, I love the envy and disgust. So I assume that a lot of people who end up Working with you or reaching out to you, they like your particular brand of weird.

Jillian Richardson: Yes.

Finn Thormeier: So there is that if you weren’t ghostwriting for someone and you were just working with someone who is writing their own content, but maybe they’re a little stuck in like this idea of what they think LinkedIn should be or how they need to show up because it’s LinkedIn, they have this thing in their head. How would you help them break that and then figure out their Brand of weird.

Jillian Richardson: Yeah. So I also offer, you know, like coaching packages, like you said, for people they want to, they want to do it themselves, but they want support along the way. And often when we get on calls, like they’ll bring a few bullet points of like, Hey, here’s some stuff I want to put in this post. And I just don’t know how to make it unique or how to write the hook for it. Like, I don’t, I don’t know what the special sauce is. And literally as I’ll just have them talk about it. And as they talk, I will start to write the post for them. And sometimes that’s all they need is just realizing, oh, when I’m speaking about this in a conversational way, there’s stuff in here that does make an interesting post, but you know, they’re so in their head of what is the LinkedIn way of saying this? They don’t think about that. They can just speak like a person and you know, then I’ll be like, okay, Here’s an interesting hook to get us in and here’s your call to action that might be compelling to people to interact with you. But a lot of people really just need space to go back and forth with the human being to figure out what it really is that they want to say.

Finn Thormeier: So I imagine myself talking through a post. What are you listening for? I’m sure at this point it’s a lot of intuition. You kind of just know it when you hear or see it. But if you had to train someone on, here are the things you’re listening for. Here are the things that once you see them, hear them, make sure you include them.

Jillian Richardson: Yeah, yeah, yeah. So a big thing is I’m listening for what might be The hook of the post, because on LinkedIn, you know, you have the first two lines that you see before there’s the learn more button. And what I tell people is a really good hook is often something that’s a little bit scroll stopping. Like you said, like I’m on my knees begging. That’s not a sentence that you usually see on LinkedIn.

Finn Thormeier: It’s a pattern disrupt.

Jillian Richardson: Yeah, it’s a pattern disruptor. And then the second sentence is often something Leaves people wanting to learn more about where is this post going to go? Like you’re not entirely sure what’s going to happen next. So you want to read the rest of the post. And so that’s what I’m listening for. I’m like, oh, what is the thing that this person is saying that is not necessarily a common belief? It’s something that’s out of the norm. And how can I start the post with that in a way that piques people’s curiosity?

Finn Thormeier: But I mean, a hook is not necessarily weird, right? That’s more like what is the interesting, controversial, unusual thing in what you’re saying that we can use to hook people. But when it comes to the weirdness or the personality part on how to add flavor to it, how do you draw that out?

Jillian Richardson: Yeah. Well, one thing I think I would say that a hook kind of is quote unquote weird because it is the What is a way that you’re, what’s a point of view that you have that’s not necessarily the norm? Like I would argue that is kind of what you might say is weird. But another way I do that for the post is in the editing process where the first pass, it’s usually a more standard kind of regular, degular LinkedIn post. And then the second pass of the post, I’ll take out, you know, any fluff, any words that you might not need in there. And then the third pass of the post is where I will like to add, you know, colorful phrases, things in all caps, things that just make people laugh a little bit. And I think that’s where a lot of people miss out with their LinkedIn posts is they just, you know, they write the first draft and that’s it. And they never think about an example I like to give is just make up a person’s name. Like if you’re talking about an issue that happens in HR all the time. Don’t just say people in HR do this. Be like, have you ever had Mark from HR? He always does this thing. We, like, everyone hates Mark. Like, I guarantee if you do that in a post, the comments are going to be dudes named Mark. Like, hey, what did I do? And like, it’s going to be a fun bit that people can respond to. It’s like little things like that. People want to have fun with your post. You just have to give them something to latch on to.

Finn Thormeier: Interesting. I like that third pass, adding personality to it. How do you even come up with this idea? I love the example that you gave with Mark from HR, but maybe that’s just your unique skill and that’s what people need to hire you for. How do you even train someone to think of that? I don’t think I would think of that even once I give it a third pass and I’m like-

Jillian Richardson: I mean, part of me is like, I’m a special, beautiful genius and no one can do it like me. But in actuality, I’m like, okay, why is it that I can do that? A big thing is I have a lot of improv training. It’s just thinking of, you know, like what are jokes that you can insert here? What are interesting turns of phrase? Like I read a lot. I consume a lot of content. I know what is an interesting phrase that stands out and will get people’s attention. So. I think that’s a way that people can do it.

Finn Thormeier: So is it like learning about comedic writing, like, like learning from, I don’t know, Seinfeld or is it, is that how you would approach teaching this to someone like studying comedians?

Jillian Richardson: I think that’s one way of doing it. This is a good question because in my classes, it’s a lot about accessing your personality. Like essentially my classes are creative writing classes, but they’re not. Only teaching humor. So honestly, okay, if I was to tell someone, how do you figure out what is funny? I have two books that are underneath my computer right now. One is the Upright Citizens Brigade Comedy Improv Manual. Would very much recommend that. It’s such a stereotypical business piece of advice, but I am someone, I have done way more improv than the average person. I did improv for six years very seriously, which is a funny thing to say about comedy. But this manual, it’s a lot of exercises to help you figure out how can I think of something that’s out of the norm?

Finn Thormeier: I thought there’s two relevant books. You just said there’s two books and one of them is relevant.

Jillian Richardson: The other one is just... Honestly, actually the other one, I do occasionally mention this book in my class as well. The other one is called The Artist’s Way. Have you heard of that before?

Finn Thormeier: What’s the... Is it Austin something?

Jillian Richardson: It’s Julia Cameron is the

Finn Thormeier: author of that book.

Jillian Richardson: The Artist’s Way. This is a little bit woo, but it’s... Essentially, it’s this 12-week process of getting creatively unblocked where you are journaling three pages every day, free form, and then there’s a lot of questions and exercises to figure out, you know, like, what did you love as a kid? How did you find joy? How were you a creative person? Wait, do you have this book?

Finn Thormeier: No. Okay, no. But it made me think of that. It’s called The Writer’s Life.

Jillian Richardson: Yeah, yeah, yeah.

Finn Thormeier: The Writing Life.

Jillian Richardson: Yes. I’m sure those books would be very complementary to each other. But like, I really do think my writing classes, they’re just, They’re creative writing classes. A reason people freak out so much, particularly about LinkedIn writing and why they can’t have fun with it is because it’s like a professional platform. So there’s all this extra stuff. I want to be taken seriously and I want to be known in my industry and seen as a A trusted person. And so there’s all of these barriers to saying anything that will make you like 1% interesting. So it can take some work to unblock yourself.

Finn Thormeier: Yeah, I think part of it is just giving people permission that it’s okay to use strong language or to use all caps or to say things like butthole on LinkedIn. Do you know if there’s a line? Like sometimes I think, I don’t know, if I was in conversation with someone and we were talking about something and I hate something, I would say, I f*****g hate this.

Jillian Richardson: Yeah.

Finn Thormeier: But then as I’m writing the LinkedIn post, I’m like, first of all, f*****g hate is very strong language. Do I really want to say this? And then the second thought is like, you always hear like the random guru, LinkedIn guru who says you can’t use swear words because LinkedIn will like derank your post if you say the F word or, you know, like, and I don’t know if it’s true, but like, that’s also where my mind goes. It’s like, I don’t want to like, Shadowban my own post just because I use the word f*****g hate in the post. I don’t know. Have you found, is there a line if I say f*****g hate in a conversation? Do I just say that? Do I say frigging hate in the post? Like, what’s the line?

Jillian Richardson: So, I mean, one option is to literally just use an asterisk in place of the you. Like, you could do that. But then there’s also ways that you could use more fun language. Like, have you seen The Good Place before? No. In it, there are In like an alternate universe and they can’t swear. So instead of f**k, they say fork. And I’ve said this in a bunch of my posts. I’d be like, oh, I fork and hate this or something. And people find it so delightful. So like, you’re like, okay. I’m trying to get across this very strong language. Could I say, I freaking hate it, I fracken hate it, I forken hate it?

Finn Thormeier: So you also feel like f*****g is too hard of a word to use on LinkedIn?

Jillian Richardson: I don’t think it’s, honestly, I have swear words in my posts sometimes, but I do also have the little fear of like, oh, if I do this too much, that might be a problem. So I don’t know why my own internal line, I’m like, s**t for me is totally fine, but f**k, I get nervous. No clue why that is.

Finn Thormeier: Yeah.

Jillian Richardson: Um, so yeah, asterisk or like figure out a more fun way to get the same thing across.

Finn Thormeier: Totally. Yeah. Interesting. Okay. So taking some improv classes, reading about comedic writing and you know, the, the Upright Man’s, what was the book? The Upright Man’s?

Jillian Richardson: Upright Citizens Brigade Comedy Improv Manual.

Finn Thormeier: It’s a really

Jillian Richardson: long title.

Finn Thormeier: Who like Do you study anyone else? And this could be a creator on LinkedIn who you love or a comedian, a writer who you study and learn from?

Jillian Richardson: This is going to sound so horrible, but I’m like, honestly, no.

Finn Thormeier: Why does it sound horrible? No, it’s okay.

Jillian Richardson: I mean, I don’t know. I’ve just been a writer for so long where people are like, how do you do this so fast? I’m like, I don’t know if you do something every day for like 12 years, you’re going to be really fast at it and it’s going to come really naturally. Like that’s just how it goes. I mean, I love following creators who teach on LinkedIn because I do always have things to learn from them. Like Kait LeDonne, I love her, Matt Barker, Jasmin Alić. These are all people that they have a lot of interesting insights. But I think my unique advantage is just the personality piece, which is kind of like, it’s a little bit vibes based.

Finn Thormeier: Yeah. I think even beyond that, beyond giving people permission that it’s okay And actually works really well if you do these things. I think I just lost my train of thought.

Jillian Richardson: It’s black space. You got to give people permission to do something and then there’s something else.

Finn Thormeier: Permission. It’s okay to do it. Oh, I remember. I think part of it is also Giving people permission to actually care about how they write and how they show up. Because I think part of it is also because of the reputation that LinkedIn has, where it’s this professional platform that’s kind of sold us a little bit. You just show up there because you kind of have to and you want to get business and there’s a lot of slop, AI slop and human slop, slop and broetry and all these things that you kind of just do it because you kind of have to and therefore you don’t really care. Maybe you use Claude because it’s just easy and fast and you can prompt something and you get five LinkedIn posts out of it and people tell you that it doesn’t really matter and you just need to hope that one of your posts somehow goes viral. Part of what you’re also showing people is that if you actually care about showing up as yourself and you care about the craft of creative writing, it works. Like it actually makes it changes things.

Jillian Richardson: Yes. Like it’s more vulnerable. It’s more scary because you actually care. Like, you know, you hit post and you’re like, oh, these are my words. Now I’m looking to see if people are interacting with it. Versus if you do a Claude post and it doesn’t perform well, you’re like, well, Claude wrote it, stupid Claude, whatever. It’s a more vulnerable act.

Finn Thormeier: Which is actually a correlation to another thing because I think, and I don’t know if you see the same thing, But you got to be active on LinkedIn, right? You can’t just post something and then peace out and don’t engage, don’t reply to people. And obviously, if you wrote something yourself that you really care about, you’re naturally going to be more likely to be around and stick around and actually answer the comments and questions that you get versus if you have some generated thing You’re like, you schedule it, you peace out, you check in maybe the next day, maybe you have two comments, but you’re like, nah, I’m not going to answer those because, you know, it’s not really my thoughts anyway.

Jillian Richardson: Yep. Oh my God. That is such a good point that you, you feel more personally connected. So you’re more likely to stay and you engage with people more. Yeah, it is like this. Do you have a LinkedIn page?

Finn Thormeier: Do you have a LinkedIn routine? Do you have things that you do every day or every week besides, you know, posting that you found have a large impact on kind of how your posts are doing and how LinkedIn is working for you?

Jillian Richardson: I have a few little things that I do, which it’s funny, the things that I do, I would assume that everyone does. And then I learned that they did it. And I was like, Oh, this is maybe not as obvious as I thought it was. Uh, one example is when I get connection requests, I Respond to them. Like I don’t just hit accept. I hit accept and then I send them a message. And I like to do this in chunks because on LinkedIn you can get like freaking 500 connection requests and you’re like, ah, what do I do? So I have my little walking pad underneath me and I like to just get on my walking pad, play some music. And then I have an opening message that I use for everyone, which is now kind of a bit because people know it’s my opening message. And I just say like, hey, thank you so much for the connection request. If you found me through an embarrassing post, No, you didn’t. And the response rate for that is super good. And then people respond and I usually say like, did you follow me because you’re looking for LinkedIn support? Or are you just, you’re here for the laughs and the vibes? And the amount of business I’ve gotten, the amount of podcast invites, the amount of opportunities, Because when you accept a connection request, it just kind of goes, it files into their connections, but they don’t get a notification. So it’s like, there’s this person, they wanted to connect with me for some reason. If I don’t say something, I’ll literally never know. It’s such a wild wasted opportunity that so many people just don’t say anything.

Finn Thormeier: I don’t do it.

Jillian Richardson: Yeah. Like just, I mean, granted, it’s a little bit of effort, but

Finn Thormeier: I do it for followers. I just thought, why don’t I do it? I go through my followers almost every day, and if someone follows me, I send the connection request, and I’m like, hey, appreciate the follow. How come? What do I owe it to? And then I try to do the same with profile visitors. I try to do the same with people who engage with my content but I’m not connected with, and they kind of fit my profile of the people that I’m interested in. But I don’t do it when I accept connection requests.

Jillian Richardson: And I feel like that’s the easiest one. I feel like connection request is like the highest, not status, like highest indicator of interest, I guess.

Finn Thormeier: Yeah. Huh.

Jillian Richardson: So there you go.

Finn Thormeier: Freak business tip

Jillian Richardson: for me.

Finn Thormeier: Quick, quick tip there. Quick tip there. Okay. Anything else that you do?

Jillian Richardson: Um, anything else that I do?

Finn Thormeier: Do you have a minimum comments per day?

Jillian Richardson: I don’t have a minimum comments per day, but I do have a lot of people’s profiles double-belled, meaning I have notifications on for them for when they post because otherwise I will often forget to comment anything on anyone’s posts and so I have people in my industry who I will learn something from their posts or people who I just really enjoy what they post. So at the very least, I will do that. And then usually when that happens, I’m like, oh, right, I should probably go and comment on one or two other people’s posts. And that’s usually enough for me.

Finn Thormeier: I think I saw you post that you recommend people to comment on 10 to 15 posts a day.

Jillian Richardson: Yes, I think that’s definitely ideal, especially if you’re someone who your own posts aren’t getting that many comments yet. So the thing my students will ask is, well, how do I get my posts seen by a broader audience? Like my posts aren’t popular yet. So how do I expand that? I’m like, well, you need to tell people that you exist. And the best way to do that is go and comment on the posts of people who aren’t following you and interact with them. So I think especially when you were in the earlier stages, that is very helpful.

Finn Thormeier: It’s one of the first things I look at when someone is posting on LinkedIn. First, I look at their content and see if it’s any good, but if I feel like they’re actually posting decent things, then I look at how often they comment. Yeah. And oftentimes like, it’s like the last comment they left was like a week ago.

Jillian Richardson: Yeah.

Finn Thormeier: And so I’m like, that’s, to me, that’s often like the first thing I would fix is like, just comment on maybe not 10 to 15, maybe five posts a day and just do that for a month. And almost always the content is better.

Jillian Richardson: Yeah. And respond to their own comments. I’m like, when people post and they don’t respond to their own comments, I’m like, isn’t the whole point of this that you want people to comment and that you’re not even going to respond to them?

Finn Thormeier: No, no, no, no. The whole point is you build a machine with Claude and that automatically posts things for you and comments things for you such that you can lean back and you have just leads. Like running in your door.

Jillian Richardson: Yes. And they think that they were interacting with you and they never actually were, which is totally fine and normal for everyone.

Finn Thormeier: Yeah. Now you also ghostwrite for clients besides being weirder and kind of allowing yourself to show personality. What are some of the other things that you’ve learned or seen that oftentimes helps get better traction, have your posts do perform better or get better results from LinkedIn?

Jillian Richardson: Yeah. So honestly, I think the biggest thing with a lot of my clients and my favorite clients to work with is that they start the ghostwriting process a little bit uncertain that they have something interesting to say. Like, they’ll be like, I don’t know if I should be posting. Like, I don’t know what’s unique about me. And I really enjoy that because it’s so fun to pull out from people. What are their interesting stories? What does make them different? Because everyone has stuff to share. And most people I work with, they’re very good at communicating their thoughts on their industry. If I ask them a question, they’ve got a lot to say. It’s just figuring out. You know, how do you position this in a little snippet of a LinkedIn post? That’s just not a skill that they have, but they could talk forever. Like that’s the ideal situation. And, you know, helping them gain the confidence that people are interested in what they have to say. And I think people especially need or could benefit from a ghostwriter in those early stages where, you know, they will Post, and then they’ll be so scared they’ll just leave and then not interact with comments or anything because there’s just this fear wall that they’ve got going on. And to also just have it in the calendar every week to be like, okay, first half of the call, we’re going to edit our posts for this upcoming week. And then second half of the call, we’re going to generate new content and like They just have that so that they don’t have to do all the mental gymnastics of writing a post every day. It just lowers the barrier to entry.

Finn Thormeier: If someone wanted to get started, founder, executive, solopreneur, whatever, do you have a program or a protocol that you would tell them, like, just start with this? Meaning, do these many posts a week? Spend this much time on the platform? Do these three non-negotiable things? What’s the kind of good starting protocol?

Jillian Richardson: Yeah, it’s a good question. I feel like it’s easier said than done, but I would say three to five posts per week. Ideally five, of course. Four is better, which some people don’t agree with, but I really do think that’s true. Respond to all of your comments. Do the five comments on a post that’s just a random post not connected to you at all. And respond to all the people who are sending you a connection request and chat with them in the DMs. Even if they’re not new business, they could give you insight on your content, why they found it interesting, what they want to hear more of. I’m just shocked at the amount of people who post on LinkedIn and then do not interact with the humans who are interacting with their content. I’m like, you’re literally ignoring your business. What are you doing?

Finn Thormeier: Yeah. I think part of it, at least for me, the AI comment slop has negatively impacted that because one, obviously, if it’s a fully automated AI slop comment, you’re like, I don’t want to answer this. But then I noticed this for me where Sometimes it’s so obvious when it’s an AI comment, right? And sometimes it’s kind of on the edge where you’re like, I’m getting vibes that this might be AI, but I’m not 100% certain. So I’m like, If it’s a real person asking me an actual question, I want to answer it. But if this is just an automated thing that you generated with AI and you didn’t actually read my post, I don’t want to respond to you. There’s a little bit of this decision fatigue going on of like, do I actually want to engage with this? But yeah, it’s crazy how many people don’t reply to their comments. I think part of it is people want to skip the hard work of starting out slow and then slowly compounding over time.

Jillian Richardson: Yes.

Finn Thormeier: And so it’s like they post, they get two comments. They’re like, oh, this is not what I was hoping for. Right. I wanted to get the 50 comments. So like, I’m not going to even bother to reply to two comments, which is like, that’s how you get to the 50 comments. Right. So yeah. Okay.

Jillian Richardson: Yeah. This is another argument in favor of making your posts more fun and incorporating humor because like on my posts, it’s painfully obvious what the AI generated comments are because AI doesn’t do humor.

Finn Thormeier: They don’t get the irony. Yeah.

Jillian Richardson: And so if you have jokes in your posts and then there’s a comment that’s like dead serious, you’re like, um, Read the room. This doesn’t make any sense.

Finn Thormeier: Or they’re a tech engineer who doesn’t get humor either. Okay. Three to five posts a week, respond to all of your comments, write five comments every day, DM all of the people who send you connection requests if they’re relevant. How long do you tell people to go through that until they should expect something to happen that resembles kind of ROI?

Jillian Richardson: Yeah, yeah. I mean, honestly, I feel like even after one month, there’s no way you’re not going to have an uptick. Like most of my students, I challenge them to post every weekday. Yeah. The numbers are always so good in terms of their impression increase because they straight up were not really posting before. And so it’s like, yeah, you’re going to have like a 12,000% increase in impressions because you were going from nothing to this or like 600, 900, whatever. So after one month, if you’re actually doing a thing, there’s no way you’re not going to see an uptick in your impressions. And then from there, it’s just having that muscle of doing it consistently. Uh, which for a lot of people is really hard and which is why I recommend getting help if you can, or if your company has the money. Um, but if you’re doing it solo, like just trying to figure out again, how to make it actually fun and where you’re learning about your business, you’re learning about your customers. You have a sense of curiosity. Cause if you don’t like you’re, you’re dead in the water, you’re never going to be consistent.

Finn Thormeier: Yeah. And I think that’s also the biggest case for why posting five times a week, because there’s people who are successful posting twice a week, but you kind of got to get through that valley of figuring out what works for you and building that audience. And obviously if you post five times a week for four weeks, you have 20 goals on shot.

Jillian Richardson: Yes.

Finn Thormeier: You’re going to iterate much quicker than if you do two posts a week, at which point it takes you two and a half months to get the same shots on goal as the other person that one month.

Jillian Richardson: That’s such a good way of putting it. I’m totally going to steal that. That’s really good.

Finn Thormeier: That’s why you kind of answer the question of like, because I think it’s not, people always ask me how many months until I see results, which is like, how many hours are you spending? Because it’s like, if you’re spending an hour a week prompting Claude, Um, you know, versus someone else who spends two hours a day, they’re spending 10 hours a week. They’re spending 10 X what you’re spending. So what you learn in 10 months, they learn in one month. So it’s, that matters way more than, than just the month from when you posted your first post.

Jillian Richardson: That is such a good way of framing it.

Finn Thormeier: Anything we should have talked about that we didn’t, anything that you find yourself often repeating to clients that you wish people understood about LinkedIn or how to be weird that we should have covered?

Jillian Richardson: Okay. One thing popped to mind. This is something I seem like I hear it more from my male clients, but it’s that People in their life start making fun of them for posting on LinkedIn. They’ll get a screenshot of one of their posts in their group chat, and they’re like, dude, what the hell are you doing? This is so embarrassing. People really rag it on them. And it makes them want to stop. Which one, I’m like, your friends are being Just major dickheads. Like they’re being horrible, but like, I get it. This is kind of part of dude culture sometimes. Um, but it’s just like, you’re trying something new. You’re trying it in public and make sure you have people in your corner who are game to support it. And like, because it’s LinkedIn, it’s extra easy to make fun of it, which sucks. Uh, But you got to be able to push through that. Like you’re doing this for a reason. You’re doing it for your business. You’re doing it for your family, whatever that might be. And sometimes people are going to be mad about it. And that’s just how it goes.

Finn Thormeier: Yeah. I also where my mind went is there is a difference between uncomfortable and cringe. Yeah. And I think the whole point of what you’re teaching people is Finding their brand of weird or, you know, showing the personality that they actually have in their content.

Jillian Richardson: Yeah.

Finn Thormeier: Which might be uncomfortable because it’s new and you haven’t done it before and you might get comments from your friends. But in the end, it’s you versus if you just do something that you believe you should be doing on LinkedIn because the gurus tell you that that’s how you need to write your posts.

Jillian Richardson: Yeah.

Finn Thormeier: And it’s not you, that’s cringe, right? That’s you showing up in a way that’s not authentic to you, even though the word authentic is being overused. And I think it’s much worse to be made fun of when you’re performing in a way that’s not you just because you feel like that’s what you need to do given the platform versus you just show up how you actually are.

Jillian Richardson: Yeah.

Finn Thormeier: And that’s uncomfortable for a while because it’s a new muscle, but in the end you’re expressing yourself.

Jillian Richardson: Yeah, totally. Like you’re, you’re being yourself, you’re bringing yourself out, which I guess, I think it depends on the person is writing it yourself even more vulnerable. Like, yes. If someone makes fun of you, actually you’re writing, is that going to be harder for you? Maybe like it depends on the person, but I really feel like a thing that I like to say is just trying is sexy. Just try. I feel like with AI and just LinkedIn culture and everything is like, oh, you got to optimize it and you got to do it so it’s the fastest thing ever. Shocker, what if you actually enjoyed it and you saw it as a slow creative process where you learn about yourself, you get to meet new people, you get to have fun. What if that was actually sustainable and good for you and you like it and it’s gonna be more vulnerable and that’s just how it goes.

Finn Thormeier: Yeah, I love it. Okay, my biggest takeaway from this conversation is I’m gonna try to learn some comedic writing. I’m gonna order the Upright Citizens book and I’m gonna ask Claude what the best books are that it recommends. On, you know, learning creative writing or comedic writing.

Jillian Richardson: Yeah. And Claude’s like, don’t do it. Don’t.

Finn Thormeier: I have been trained. Cool. Thank you, Jillian, for taking the time. If people want to check you out, obviously I’ll put your LinkedIn and your website in the show notes so people can reach out to you if they want to get weirder on LinkedIn or maybe hire you as a ghostwriter. They can do that. And yeah, thank you for your time.

Jillian Richardson: Thank you so much. I had fun.

Dan Slagen is the CMO & Chief AI Transformation Officer (CAITO) at Zapier. He joined just over a year ago as SVP Marketing, and recently got promoted to own the company-wide AI transformation mandate.

Before Zapier, he was CMO at Tomorrow.io, where he helped grow the company from $2M ARR to a $1B+ valuation, CMO & Chief Culture Officer at ThriveHive, and Head of Global Advertising at HubSpot.

In this episode, we talk about the future of the CMO role, why the CMO should (?) own the company-wide AI mandate, his “red alert” for Zapier’s marketing team, strategies to speed up your team’s AI adoption, and much more.

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We discuss:

* Why Dan took on Zapier’s company-wide AI transformation mandate as the CMO

* Dan’s case for fewer CMOs

* The “red alert” he called on Zapier’s marketing team

* The first step to making your company (and marketing org) more AI-native

* Zapier’s internal AI policy

* LLM jail, automation debt, and why only 24% of GTM workflows need AI

* Why AI is causing “generation loss” & what it has to do with your approval processes

* What every CMO behind on AI should do this weekend

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Show Notes:

Connect with Dan Slagen:

Dan Slagen’s LinkedIn: https://www.linkedin.com/in/dan-slagen-718675a/

Dan Slagen’s website: https://www.danslagen.com/

Zapier: https://zapier.com/

Connect with Finn:

Finn’s LinkedIn: https://www.linkedin.com/in/finnthormeier/

Thormeier.co - Founder Brand & LinkedIn Advisory: https://thormeier.co/

Mentioned in the episode:

ZapConnect (Zapier’s annual conference): https://zapier.com/zapconnect

Dan Slagen’s “LLM jail” & “Automation Debt” post: https://www.linkedin.com/posts/dan-slagen-718675a_our-team-keeps-hearing-the-same-two-words-activity-7490753511693930499-8NRJ

Zapier’s AI Workflow Index (Q2 2026): https://zapier.com/ai/workflow-index/q2-2026-report

Tomorrow.io: https://www.tomorrow.io/

Tom Wentworth (CMO at incident.io) episode: https://www.founderbrand.org/p/the-most-ai-pilled-cmo-in-tech-shares

Don Jeter (CMO at Torq) episode: https://www.founderbrand.org/p/how-to-radically-stand-out-w-don

Torq: https://torq.io/

Paul Roetzer’s SmarterX: https://smarterx.ai/

MAICON: https://www.maicon.ai/

Clay’s AI writing policy: https://www.clay.com/blog/ai-writing-policy

Claude Code: https://claude.com/product/claude-code

Cursor: https://cursor.com/

Codex: https://openai.com/codex/

Midjourney: https://www.midjourney.com/

HeyGen: https://www.heygen.com/

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Full Transcript:

Finn Thormeier: All right. My guest today is Dan Slagen. He is the Chief Marketing and Chief AI Transformation Officer at Zapier. Zapier, I’m sure given my audience, everyone will know it’s an automation platform, or as they say, it’s the most connected AI orchestration platform. Dan joined Zapier a little Over a year ago as SVP of Marketing and recently was promoted to CMO and CAITO, Chief AI Transformation Officer, which is a very interesting combination and we’ll discuss that.

Before joining Zapier, Dan was CMO at Tomorrow.io, where he helped grow the company from $2 million in ARR to $1 billion plus valuation in five years. CMO at ThriveHive, where he led the team through a $1.3 billion acquisition. CMO at Alignable, Head of Global Advertising at HubSpot and many other roles including founder of a video tech company for a year and he was also named one of Forbes top 50 entrepreneurial CMOs of 2024.

Dan thank you for joining and anything to correct or amend there in the intro?

Dan Slagen: No, appreciate it. Very, very kind words, but happy to be here.

Finn Thormeier: Cool. What’s the story behind the new title and is it disconnected or is there a reason why the company-wide AI transformation chief officer title was given to the CMO?

Dan Slagen: Good question. So I joined Zapier about a year ago and it’s a, you know, 13, 14 year old company, a lot of history. And so, you know, first and foremost, I think they want to make sure that someone coming in at this level is not going to stick around for a little while and leave. They want to make sure that someone who’s going to be really invested in the company and all that. And so it’s funny, you know, any Any executive marketing role these days, I feel like it’s a one-year trial, essentially. It’s a test. I’m going to see if I like the company, if I like working for the CEO with the exec team, and they’re going to do the exact same thing back to me.

And so as we were nearing the one-year mark, Wade and I... Got together, Wade’s the CEO, co-founder of Zapier, and we sort of had the conversation of is this a one-year deal or do we want to try and sign a multi-year contract? What do we want to do? And we both felt like the relationship was going well and this had been a fruitful experiment so far and it felt like something we both wanted to invest in moving forward.

And so as we did that, We also sort of talked about how else could the role expand and what else could you do outside of marketing. And so I’ve been extremely fortunate in the past to work for some smaller startups that went through hyper growth where you own everything. You know, I can remember roles where I owned marketing and sales and CS, BD, like everything, just building those systems from the ground up. Certainly not at the scale that Zapier is at, but I had some good familiarity. The one common factor with all of that was growth and pushing the limits on the technology that we’re using.

And so with AI, you mentioned my last company, it was a really, really small marketing team. With a very small budget. And so when AI came out, that was an aha moment for me of being this thing that we can finally compete with the biggest companies in the world. The playing field is finally level. I can do all these things I haven’t even been able to do. I wasn’t so excited about AI at first because it made the things I was doing better. I would tell you because I could literally do things that I couldn’t do before. I just told my CEO, can’t do that, can’t do that, can’t do that unless we, you know, get headcount or budget.

So I’ve stayed really close to that. And I’ve also stayed really, really close to the culture. In another previous role, you mentioned ThriveHive, I was the chief culture officer as well as the CMO there. So I started to learn a lot about that. And at my last company, the culture team and I partnered so closely together. So I’ve had all this experience that was sort of building towards something I didn’t quite know what it was. And it fruitfully ended up being this dual role of marketing and AI transformation at Zapier.

Finn Thormeier: Do you think marketers are somehow better suited for that type of role or was it just really this unique mix that you personally had that will not apply to other marketers as related to their peer leaders?

Dan Slagen: That’s an excellent question. I truly believe that someone sitting in The head of marketing role is in the best position in the company to lead it.

However, A lot of the personas that I see within marketing either have not had the experience that I just went through or do not have the mindset to be able to do it. They’re too focused on one thing. They know how to tell a really, really good brand story, but they have no idea how to think about pipeline and demand generation or the inverse of that. And it is hard to find someone that truly can spike across all three areas. Happy to dig more into that. I think if you can find the person with the right background, someone sitting in the marketing and growth department is an incredibly dangerous persona that can help the business immensely.

Finn Thormeier: Not to go on too much of a tangent, but you said At Tomorrow.io, you had a very small team. I think I saw you gave a presentation where you had four people reporting into you and that when AI happened, you felt like you could finally do these things that you hadn’t been able to do because of lack of headcount. Are there any specific ones that you can mention here where, again, things that you wanted to do but really couldn’t and now finally you were able to do?

Dan Slagen: Sure. One example that I like to tell is, you know, when I was at the company, we got included in an RFP from a major entertainment brand. They own theme parks around the world. They have lots of movies. You can probably guess who I’m talking about. And the RFP was really, really last minute. And we had a week or two to get something to them. And we knew there were 10 other companies all pitching. And we were added late. And they’re like, what are we going to do to stand out?

What we ended up doing was we created this video using AI where we went to all of the movies that the entertainment company had created and we saw where all of the characters were impacted by weather. And we’d be like, what if they had had access to our technology? They would know when to leave the dock. They would know when to go fly. They would know when to go outside. They wouldn’t be at risk. Literally use the exact scenes from the movies and the characters and all that.

And when we showed it to them, the response was literally, we love how much you just love our brand. You stood out so much compared to everyone else. We’re going to move you guys to the next round. We haven’t even looked at your technology yet. We’ll worry about that in the next round. But just they’re one of those companies that they want to see that people love their brand and get involved in their brand.

And so, you know, that’s something that, again, I wouldn’t have even proposed that prior. And, you know, we did this when, you know, Midjourney was really getting good. The video creator was starting to get good. We were using things like HeyGen AI to do all of our product marketing videos. So we were getting good at that really, really quickly. And so, again, it was sort of a new thing we could even offer the sales team that we wouldn’t have even thought about.

Finn Thormeier: The CMO role, I’ve seen so many posts about this recently, and even Tom Wentworth, a fellow Boston CMO who sends his regards, by the way, when I interviewed him about how he thinks the CMO role is evolving, Even he said he could see a future where the CMO title or role doesn’t exist. What’s your take? Is the CMO role dead?

Dan Slagen: No, not at all. I love Tom. Look, I go back to... Honestly, I go back to a couple things. One, you look at the education system and you look at colleges and universities. And when I was in school, the truth of the matter is I didn’t have the brain to go into finance, accounting, right? These are majors where you have to know your stuff. You have to know your numbers. You can’t BS your way through a finance degree. You can’t BS your way through an accounting degree. And a lot of kids Fall into the business school because they just think that’s what I’m supposed to do. I’m going to do business. And you know, the entrepreneurial tracks, not for everyone. That’s its own thing.

And so a lot of people fell into marketing because it was seen as a little bit of a fluff experience. You could kind of BS your way through these classes. What’s creative? How do you judge creativity? What’s good? What’s bad? No college professor is going to sit there and tell a kid their creative thinking is not right. Everyone kind of got a free pass. And so one, I think you had an extremely low bar of people getting into marketing just because. And there wasn’t so much of that like rigor.

Two, how do you think about marketing? There’s so many ways to think about marketing. You can appeal to people through creative. You can appeal to people through direct response, through really good product marketing, positioning fit. Like there’s so many parts of the job and depending on where the company’s at and what they’re trying to do, you need to be able to call on different parts of those things.

You don’t see that in other roles on the C team. CFO sort of knows what to do, you know? Head of Sales kind of knows what to do. Marketing, whenever I talk to a CEO and they want a marketing lead, my first question is, well, what does the company need? You know, you would never ask that question if you’re asking about like a CFO role. You kind of know for the most part what’s going on. So there’s so much ambiguity and it’s very hard to find someone that can just run across all those things. You have to have extreme width and enough depth to be dangerous and that’s really hard for people.

Again, I think I’ve been extraordinarily fortunate the way I was raised, the jobs I’ve been able to have, where I have the analytical side, the creative side, I’m connected to the business, I know what’s going on with sales, but I can also take creative moonshots and do really silly things and turn around the next minute and do something that’s really buttoned up and directly focused on ROI. And it all lives in your head. There’s just a lot you have to think about and the composure. So it’s just a really, really hard role.

All that to say, There’s no way the CMO role is dead. It’s possible that we’ll see fewer CMOs, but I think the ones that retain the title are absolutely at the top of their game, and these companies cannot be living without them. I also think we could see a role where companies come back to wanting a CMO as well.

Finn Thormeier: I mean, that makes a ton of sense to me, and there’s obviously a lot of people doing clickbait stuff, and maybe you answered this question, but Is there a deeper reason why there’s even a conversation about the CMO role being dead or obsolete? I’ve not seen similar takes about the CFO role is dead.

Dan Slagen: One thing is I think you see way too much celebration in marketing without knowing if it improved the business. And you could have a great brand campaign. You could have an innovative way to think about positioning, but were you able to connect it to ROI? Were you able to connect it to revenue?

I remember my very, very first day at Tomorrow.io. We had got the whole team together. We were at all hands, and I’m introducing myself to the company for the first time. The first thing I said to that company was, I am a sales-oriented CMO. First and foremost. And this is coming from someone who loves big brand play. I do a ton on PR. I told you about video creation. And we’ve done a lot at Zapier this year. We did Super Bowl. I love brand.

But I am also talking to my CFO every single week. We have a shared spreadsheet with the numbers. We talk the same language. I know ARR. I know our time to close and our ACV. I know our churn rate. I am... First and foremost, living in finance world. Then I’m living in sales world. Then I’m living in marketing world. And so having that understanding, you know, my CEO can watch my CFO and I have a conversation and he knows we’re speaking the same language. There’s no confusion around that.

But I think one, not understanding the business. Two, not being real with yourself about the impact of marketing. I’ve done some campaigns in the past that looked fantastic that had no impact on the business. I’ve also done things almost in silence that have grown huge ARR. And so there’s just this notion of sort of celebrating. And then the last thing again is every company thinks what they want for marketing is different and what they need is different.

Finn Thormeier: Right. So if the CMO role is not dead, what is the future of it? How is it changing? I mean, you’ve been a marketing leader for a long time. Now at Zapier, how is the skill set changing? How is the role changing? Talk to me about the future of how you see it evolving.

Dan Slagen: Yeah, it’s a really good question. Paul Roetzer, who runs SmarterX and the MAICON Conference, has done some really, really good work around sort of how AI is impacting marketing. And he had a post sort of this week talking about the Astra release and just, you know, how his level of optimism got a little bit lower when this came out because he’s just not sure how much people are going to be able to adopt this stuff.

First and foremost, what I try and do is I think you have to call a shock and awe moment with your people. And I think you have to do a little bit of fear-based leadership, which is not my style at all. I hate it. But every once in a while, you got to wake people up and say, hey, if you don’t learn this technology, I’m genuinely not sure what the future holds for you. And I’m also not sure what the future holds for me. So... Full stop. Let’s start there.

The first thing I do is make sure anyone coming through the front door to join the marketing team now is at a level of AI that I’m comfortable with, and it’s got to be on the cutting edge. So we have an AI fluency bar that we hold people to in the interview process, and we’re pretty nuts about it. So you have to stop the bleeding of people coming into your organization that might not be at the bar that you’re trying to build into.

Two is you gotta get in with your people. And like I said, it’s gotta be a shock and awe moment. So earlier this year, You really started to see non-developers using traditional developer tools for go to market. Claude Code, Cursor, Codex. You could see where it was going quickly. And I felt like the Zapier marketing team could potentially be at risk of falling off from being the most innovative, you know, AI thinking marketing team. We were at risk of falling down at least like one rung on the ladder.

So I called a red alert, got the whole team together, and I essentially brought someone in to do a presentation and show people how they thought about the future of AI marketing, how they built their digital twin, how they were building agents, everything, the whole deal. And it was pretty technical. We were almost in a terminal the whole time. And it was a 45-minute presentation.

After that, I asked the marketing team, who’s feeling overwhelmed right now? Everyone’s hand went up. And I said, yeah, you guys didn’t know that this person existed when you woke up this morning. Like you don’t even know that you’re interviewing against this person for a future role at Zapier or for a future role that you want outside of Zapier.

You’re going to have three weeks to go learn any coding tool that you want. Cursor, Claude Code, Codex, whatever it might be. After that, we’re going to do a build-a-thon. And what I told them was, I know you’re feeling overwhelmed right now, but for the next couple weeks, I’m going to give you access to five coaches. We had five power users on the marketing team. And you can ask them any question you want. Spend as much time with them as you want. I’m not going to know who’s asking what question, what question is being asked. I have no idea. But in three weeks, you’ve got to show up ready to build.

The team did that. I think we were like 95% ready to go. The team heard me loud and clear. Then we did a two-week build-a-thon and everyone built something. At the most basic level, someone built an interactive dashboard showing leads or impressions or whatever. Other end of that, someone built a fully functioning app that our events team is using to run our ZapConnect conference, which happens later this month. It’s our big annual flagship conference. We’re now using a homegrown app to manage 100 plus speakers and the majority of the conference. Really, really cool.

It then broke the team up into essentially three tiers. Tier one, you got the most basic builders. They’re doing the dashboards. Tier two, people starting to build systems and roles. And then tier three, you got full functions and almost companies being built within the marketing team. Now I can go to each of those tiers and give them different business challenges that I would like them to solve, and each tier I’m giving them challenges that are at their level, tier one, tier two, tier three, versus just saying the whole marketing team try and get better.

First, stop the bleeding. Make sure your hiring’s in a much better place. Two, you got to get in the weeds and build with your people. You know, when I did the build-a-thon, I got about 60 plus projects that came in. Everyone recorded a two-minute Loom. I watched every single one. I gave handwritten notes to every single person. We gave awards. I also built my own thing. And that was a really, really big moment for the team. And now they are on just a different building trajectory.

So you asked about what are the skills I’m looking for? Resilience, adaptable, curious, willing to learn, willing to change. I’m not going to sit here and say that 100% of the people on the marketing team loved what I was doing. Not everyone stayed, right? We also said, hey, you might not like this new way of working. This might not be for you. The way I’m working now is so different than it was five or 10 years from now. Fully understandable if you don’t like this. But this is where we’re going. And you’re either on the ride or you’re off the ride. And it’s okay if you’re off the ride. But we have to be honest about it. So those are kind of the big, big cultural shifts that we made this year.

Finn Thormeier: How do you... I guess you just enforce it. I’m just thinking, I’m sure there’s a lot of resistance that a lot of marketing leaders will face if they will try to do this. I guess you need to get the buy-in of your CEO beforehand. How do you recommend them to think through and deal with the resistance?

Dan Slagen: It’s a good question. A couple of years ago, I would have told you top-down is the most important thing. At this point, what CEO doesn’t? We are extremely fortunate at Zapier. We have access to every single AI tool in the world. There is no So Zapier is like an AI playground where you can come in and use any tool you want. And it’s very unique, but it’s a really, really great place to be. But as long as you can give your people access to the most interesting tools that they need, that would be a good step one.

You know, two, we try and be as transparent of a company as possible. And for those that follow Zapier, you know, you’ll see us posting as much stuff about the company and what we’re seeing in benchmarks, but we also do that internally. So when I call this Buildathon, it is in the public marketing channel that anyone in the company has access to. Everyone’s project is in there. If you didn’t do a project, you’re going to be on the side of the line that says no project. And so there’s a little bit of FOMO and, you know, competitiveness that we’re driving there.

And like I said, you know, not everyone stayed and that’s okay. But the thing that I needed to solve for was I don’t want anyone in the middle. That’s the worst part where you have those people that are just kind of doing what they can to stay by, but they’re probably pretty toxic for the culture. In or out. That’s just a decision we’ve made. It’s also more fair to your A players who want those types of other peers to build and get inspired with.

So working in public is a huge, huge part of it. You know, Zapier, we go so crazy as to, we do most of our communication on Slack. And so every month we have a Slack transparency leaderboard that gets published in front of the whole company and it’s just for the executives but it shows the company what percentage of Slacks an executive did public or private that month. The reason we do it is one culturally it de-risks you from things hiding or toxic stuff or drama but on the more positive side when you’re trying to build this AI brain and institutional AI you need to have Your conversations in public so the AI can actually see it and pull from it and move it forward.

And so when I joined the company, I was about 50% public, 50% private. I’d never really measured myself. That’s just sort of where I netted out. And then I made a big, big push to change that. I’m now 98% public, 2% private each month.

Finn Thormeier: The number one exec.

Dan Slagen: They say I’m number two in the company, although we have yet to meet number one.

Finn Thormeier: You need to know who’s number one.

Dan Slagen: I know. They didn’t want to reveal themselves last month. We’ll see. But yes, by far and large, number one for how much I Slack.

The other thing we do is we built a marketing OS and marketing brain. And so every morning I ask the marketing team, this is the first thing you need to look at. It looks like an interactive dashboard, but it shows you What happened yesterday? What’s happening today? What’s happening tomorrow within marketing? What you need to care about? How are we doing against goals? And that was a change for the team. I said, you need to look at this every single morning because once you start to understand what’s going on within the business, now we can start to run agentically off this in a much more exciting way.

I have tracking in place so I know who’s looking at it and who’s not. And so it’s very easy. Again, it’s very easy for me to tell who’s paying attention and who’s not. I’m not here to Shame anyone. We’re not here to call people out, but we are here to enforce a behavioral change and you’ve got to be pretty strict on it.

Finn Thormeier: Do you, I mean, I love all of this. Do you think you’re losing something by almost, I mean, you talked about the kind of interview questions and the AI fluency score. Do you think you’re losing anything by forcing every marketer to be deeply AI native?

One of my favorite interviews I did with Don Jeter, the CMO at Torq, and I mean, They’re obviously crushing, incredible brand, very experiential. They do a lot of field marketing. And I asked him about kind of AI and he’s like, I don’t do a lot. You know, an AI, he himself, and they also have a rule that you’re not allowed to use AI to create any kind of design that’s customer facing, anything that the world sees. And they’re obviously crushing because they focus on the brand, the storytelling, the experience. Does every single marketer have to be AI native?

Dan Slagen: It’s an excellent question. I think... I’m gonna say yes. I’m gonna say yes on that one. I think it’s easy to say no. The safe answer is to tell you no.

Finn Thormeier: Yeah, yeah.

Dan Slagen: I think... And look, Zapier... We do a ton of in-person events. It’s extraordinary. We are pretty much doing an in-person event every single week somewhere in the world. I was in New York last week with 20 or 30 major companies that you’ve heard of just in a room for five or six hours just talking AI transformation. What’s going on? We love the in-person stuff. We do these amazing events called Outposts where we get people to We had them at Zion National Park. We’re at a castle in the UK this week. We do awesome stuff because we believe in communities so much.

We also have tons of checks on what actually goes out to a customer. I personally don’t write with AI, especially for internal comms. I actually think that’s a superpower now that I...

That said, the way that our company works and the amount that we can speed up when these systems are in place is so important to us that I want people that are at least curious enough to go explore that. Now, I’m willing to hire someone that’s not Currently at the cutting edge of AI. That’s fine. And we’ve done it. What we look for is what’s the thing that’s going to be your hockey stick moment to really, really make you understand how to use systems. And I think the AI thing, the terminology gets overused. It’s like, would anyone on the team want a couple more headcount to help them do things? Of course they would.

So I have someone on the team that when we interviewed, They weren’t great on AI, but man, they were curious. They were so creative. The way they thought about it was interesting. And they were like, yeah, I think I’m getting to the unlock moment. And I felt like if we can bring you into Zapier, I can very quickly get you that unlock moment. And we did. And now that person is doing so much great stuff because they are creative first. But they have access now to essentially a much bigger team and resources and output that they can get stuff done with. And they think about what the customer is going to see first, not how much the AI can generate. And so I think that’s a very important distinction.

Now I’m speaking specifically for Zapier. There’s certainly, I can imagine, other... Other companies, other industries where maybe it’s not as important, but for us it’s something that we’re currently not really willing to bend on.

The last thing I’ll say is I think you’ve got to understand something to be able to ignore it and to be able to ignore certain parts of it or speak out against what parts you think are really dangerous. Unless you really spend the time getting in the weeds of what can be done, what should be done, Then how do you really know? You’re just reading headlines and you’re getting, you know, you’re kind of being led by clickbait to some degree. So I want my team to understand the pros and cons, the inspiring, the ethical concerns, all that thing. I want them to know that and master it so then we can make informed decisions.

Finn Thormeier: I’ll have a follow-up question on that, but before that, I’m thinking on the spot here, and maybe this is a stupid question, but when we’re talking about the future of the CMO role, it definitely seems like, at least from your point of view, systems thinking will be more important because you will be working more with AI, and for that, I think systems thinking is very important.

I don’t know who I talked to. I think it was Sydney Sloan, but there’s basically three tracks towards the CMO role. There’s the product marketing track, the brand track, and then the demand gen track. And I think she said most come from the product marketing track. Will that change where maybe because of that people who have more of a demand gen background, data background, engineering background, sales engineering background, where there’s a little bit more emphasis on this kind of systems thinking, will have an easier time thriving in that new world?

Dan Slagen: To some degree, yes, but Sometimes that mindset can also stop you from doing things that don’t scale. And that continues to be an important thing. There are parts of our in-person events motions that don’t make sense from a systems standpoint. They just don’t. But I fully believe in them and I would do it. There’s parts of our brand work that doesn’t quite make sense from a systems mindset. But we do it and we think it’s a good idea. So I think the problem with systems mindset people is sometimes they’re not as flexible as you need them to be.

This is where the role gets really, really hard. You know, again, I was extremely fortunate. I think the way I was raised, like I go back to like my parents, my mother was a nurse and my father was a psychologist. It’s the perfect combination of watching two people work. One is like helping people like with their heart and the other person helping people with their brain. You could see both like the left side and the right side working and you could try and find the perfect mix.

And so if you’re only systems thinking, you might not be able to go deep enough on one part. You might not be able to go deep enough on the brand and the emotional part. Or if you’re overly thinking on that you might not be able to connect it back to the demand or the product and the positioning. So again it kind of goes back to these people that can understand what a company needs and try and harmonize what the right balance of each three might be. So it is systems thinking but it’s the ability to Work in a flexible system as opposed to a rigid system. And I do see a lot of systems thinkers be too rigid. And that’s when I think you usually see marketing really fall flat.

Finn Thormeier: To come back to the previous topic, do you guys have any hard rules or published guardrails around how you allow your marketing org to use AI? What’s allowed? What’s not allowed? I believe Clay recently published their AI writing policy. Do you guys have anything in place? And if not, what’s your personal stance on where it’s useful and where you shouldn’t?

Dan Slagen: Yeah, yeah, yeah. You got internal, external. I’ll say for internal, again, we’re almost 800 people on Slack as our primary form of communication. So there’s a lot of comms. We started to notice it earlier this year. It’s like I saw my first Harry Potter wizard fight, essentially, at Zapier. This is a while ago. But someone had their AI create a doc, and they fired it over into the channel. And the other person clearly didn’t read it. They had their agent read it, and they fired their response back. They did this back and forth three or four times. And at some point, you can tell, guys, stop. Both of you. Turn it off, go read the docs, and we’ll come back and we’ll discuss this in person. But you could just see that stuff was starting to happen. And it wasn’t malicious behavior. It’s just there’s so much going on with more things being created. You’re trying to keep up, and people are just, they think something’s good enough, and they’re doing their best there. So you can start to see it.

We did implement an internal policy. It was really just rooted in respect. And this was a while ago. But it would be things like, it started with, You need to be honest with people when you send something, whether or not you read it and who wrote it. Like, hey, because there’s times when I’ve said, hey, I took what was going on. I just tossed in this prompt here. Let’s just, I don’t even know what’s in it. Let’s just start working on it together, brainstorm. Great. Then the person or the people I send, they know where I’m coming from. In my role, if I send something, people are probably going to read it or feel compelled to read it. So out of respect for them, I need to let them know, okay, I actually took time to write this. This is real. I need you on it. Or, hey, this is just a thing I made. Let’s just, I don’t know, we’ll jam on it later. So that was good to see.

Two, we look at, for external, we look at any comms that would ever go out. And there’s a lengthy testing period. And we are more than happy to keep humans writing when and where. It makes sense. Because I think the second AI takes the excitement out is really when you start to see, I think, diminishing returns.

So yes, internal, external policies, we’re pretty rigid about it. I think we’re, on the exec team, I’ll also say, I think we’re We are perfectly honest with each other and we have no problem shaming each other when someone clearly, I’ve been shamed before, we all have. But just being honest about that right from the start was the thing that really, really quickly improved the behavior.

Finn Thormeier: Yeah, especially because AI likes to go for the 12 page report rather than the quick and concise feedback.

Dan Slagen: 12 page report, I also think there’s times when we’ll embark on A step function change in the way we operate as a team or a company and we’ll acknowledge the fact that it’s going to be really messy. And we’re looking for feedback and we say, if you ever need something, you know, just raise your hand and let’s have a real discussion about it.

But, you know, for instance, we do a monthly check of the business where we look at all the numbers, all the stuff that happens and we kind of have a mini all hands. The department leaders would sort of write their narrative and they’d get their numbers and they’d kind of all present. We moved that to an agentic motion where we just have the whole report written, sent ahead of time, and we show up and talk.

We were very honest with the company that, hey, the first time we do this, it might not work. The data might be wrong. The narrative might be wrong. But we were honest about the vision we had and where we wanted to go and why. And so if you can get people bought in as to why we’re doing this and they feel bought in, inspired, and most importantly, safe, then they’re more enthusiastic about it and they’re more willing to help improve it versus just throw stones.

Finn Thormeier: I’ve seen some of your recent posts. I’d like you to explain and or expand on a few terms. Let’s start with automation debt and LLM jails.

Dan Slagen: Sounds good. The LLM jail is one that I find happening quite a bit at the enterprise level. One of the reasons that we love Zapier and our customers love Zapier is because it gives you this notion of interoperability where, you know, one, different models are good at different things. We see that. We have our automation benchmarks where you can see certain models spike And so you want to be able to make sure that you can actually pick the right model and the right LLM for the thing that you’re trying to do.

The other thing is that you don’t feel lock-in if something happens that you don’t like, if they make an announcement that you don’t like, if they start to make an announcement that you don’t like. Make data decisions that you don’t like or you’re not comfortable with. And the other thing is that you are not bound to their rate of acceleration. You’re bound to your own rate of acceleration and you’re more in the owner’s seat there. So I think it’s pretty rare for me to meet an enterprise that says we’re going all in on this one. This notion of interoperability is pretty clear there. So that’s kind of what we meant by automation jail. You want to make sure that you’re LLM jail. You want to make sure that you’re not Not able to do things because of the system that you’ve put in place.

You know, automation depth, you know, there we really start to look at what gets automated and essentially like how deep we’re able to go. So for instance, you know, we all started by automating little things like, let’s say our communications. I now have it automated where if an email comes in, it goes into a folder, it drafts up my reply, but it doesn’t respond yet. So it’s not fully end-to-end. The depth isn’t fully realized. That will happen when I feel so comfortable with my system that I get an email in, it can craft up a reply, and it sends without me even looking at it. Now, when will that happen? This year? Next year? Never? I don’t know. It’s just kind of dependent. That’s where sort of the judgment call is. Do you want to take your hands fully off the wheel, or is that something where you do want to stay involved at the human level?

So I think the depth, one... It relies on the technology being at a place where we feel comfortable, but it also relies on the place where we have to make our own calls as humans as to what we want to still be in the loop on or fully own or turn over to AI.

I think, you know, I was on a panel last week at a conference and they’re asking about the predictions for next year. And my biggest prediction a year from now is that we’re going to see people pushing back on AI more versus AI pushing on people. Like right now, AI is pushing on all of us in the tech world and in marketing. It’s like if you aren’t up to speed on the latest model and the latest thing, it’s as if you’re going to be viewed upon as obsolete. And there’s a lot of pressure being put on you by Just the marketing campaigns coming out from the LLMs. It is rare to see marketing campaigns taken with as much... It’s as if there’s like whatever they put out is destiny and the world is responding to that. That’s what it feels like sometimes. Which we know is not the case.

And I think you’re now starting to hear and see, especially in the in-person communities, you’re starting to see the uprising. And you’re starting to see people pushing back on it and saying, you know what? Wait a minute. I don’t want to do that. I don’t think that’s the right thing to do. And it’s good to see because I think people have been getting pushed around for the last two years with this tech push. And it’s time for us to start pushing back.

Finn Thormeier: Yeah, and I think part of that automation debt was also that you guys figured out that for a lot of workflows, you don’t need any AI. And I believe in that post, you wrote about only 24% of kind of the workflows, the things that you want to automate, the things that you build in, let’s say Zapier, actually need AI at any given step, and the rest you can just do without AI.

Dan Slagen: It’s the interesting thing. We call this fluid determinism. And so one of the things that Zapier is so good at is deterministic workflows. And it’s really what the company has scaled on in a lot of ways. And now as we’ve seen so many of these agents get built, ultimately what they are is fancy workflows. And the reason that token cost is so much and they’re spinning out of control is because they’re using AI for everything where you don’t really need it. For the most part, the workflow needs to do the same thing every single time. And it needs the ability to call AI when it needs to, but not run the whole thing like that.

And so that’s where we’ve been able to improve efficiency, drastically improve costs, reduce risk. And that’s the thing that people are really starting to warm up to. And that’s one thing that’s unique to Zapier. So yeah, that’s one part where I expect to see Big area of growth and almost like a resurgence of nostalgia and almost like going back to the original reason that Zapier existed. But in this new chapter of AI, when people are starting to come back to their senses and say, OK, we need to do this in a sustainable way.

Finn Thormeier: Right. Yeah. The other term that I saw that I loved that I want you to explain is generation loss.

Dan Slagen: Yeah, this was a really interesting one. So, you know, for those of you that maybe remember old VHS tapes, like movies, people used to make copies of them. Anything you make a copy of, you know, every time you make a copy of something, the quality gets worse and worse and worse. And back in the day, it was something like if you made nine copies of the same VHS tape, by the ninth version, it was completely blurry and fuzzy. And you didn’t even know what you were looking at.

And we see this in marketing, we see this in other departments, but you start with an idea or a brief, and it goes through so many different iterations of approval processes or changes that by the time it goes live, it doesn’t even look like the idea that you had initially.

Finn Thormeier: And it took me a little too long, but just so people can see on the screen now what that looks like, what you’re talking about, the first generation of a VHS and then... Third generation, fifth generation, and by the time you do the ninth copy, you get a bunch of ghosts.

Dan Slagen: Yeah. And so... As we started to build out our marketing brain and our marketing OS, we were really worried about generational loss because what we wanted was the most honest version of opportunity for Zapier to be the thing that goes live.

And so every month we have a meeting that includes the CEO and head of sales and our product marketing leaders. And we look at the last 30 days in everything, what happened in the world, what happened inside of Zapier, outside of Zapier with competitors. What deals that went well? What deals that did not go so well? What campaigns worked? What didn’t? And then we synthesize all that, and we think about the next 30 days. And we say, how much needs to change in our go-to-market? Do we have new messaging we need to test? Did something happen that we need to go jump on? Now sometimes, nothing really changes, and the next 30 days look very similar to the last 30 days. Other times, it’s time for a big change. Starts new motions.

The output of that meeting, you can imagine getting filtered as it goes from team to team to team and finally goes live. Where you just want the most honest version of the next 30 days will be this, go. And so as we took that and mirrored it with the marketing brain and the marketing OS, what we were trying to solve for was generational loss and not having that. We want the most honest version of the outcome of that meeting to go directly into the marketing brain and OS and immediately start to power our go-to-market. The content we’re going to create, the ads we’re going to run, the emails we’re going to send, the decks we’re going to show in the next sales meeting. And that’s really what we were trying to solve for there.

Finn Thormeier: Where does your marketing OS live?

Dan Slagen: Our marketing OS, we built it on Zapier. And so essentially people log into Zapier every morning and they go through it.

Finn Thormeier: But it’s like, it’s an interactive tool that you kind of build into the platform or?

Dan Slagen: It’s an interactive, it looks, to most people, it looks like an interactive dashboard.

Finn Thormeier: Okay. And I believe part of that is also, I don’t know if this is like a separate thing, but one thing I saw that you guys built Synthetic personas, but they’re built on actual sales conversations and product, how people act, behave inside of the product that then your team can ask and prompt to kind of get feedback on marketing copy and stuff like that.

Dan Slagen: Yeah, this one, we do it. I don’t think we’re, we’re not unique on this one. And it’s helpful, but it’s not at a level where I would replace real motions. But yes, the idea being is that you can build synthetic audiences to get a sense of what’s going on.

I think where it’s been the most helpful is actually with internal... Things where, you know, if the team knows they’re gonna present something to the CEO, they present it to a synthetic CEO first, or like AI CEO first, trained on all the things that our CEO is currently thinking about, talking about, posting about on Slack, pushing team for, and you can get a sense of, hey, If I give this to Wade, how is he likely going to respond? And so that’s been very helpful for the team. Before you go to anyone at the company, but definitely the C-level or CEO, make sure you’ve run this through. These are the expected reactions. You might want to think about doing this or that. That’s been a good kind of check step for people.

Finn Thormeier: Which is, again, that comes back to the transparency score that you have. Because if you, as the CMO, write 98% of your messages in the public account, Slack channels, someone can pull out of all of that and say, you know, look at all the things that Dan has been discussing and prioritizing and then cross compare that to what I’m trying to present here and give me a sense of if this fits anywhere to where Dan’s mind seems to be at right now in the last 30 days.

Dan Slagen: Exactly. And I will say the thing that the way that that works and the reason that works is because my CEO and I have trust. Because I’m willing to have conversations in front of the whole company. I am wrong a lot of times. I have ideas in public Slack channels where the CEO or someone else will say, that’s a horrible idea, that’s wrong, no. It’s okay. We’re all here. We’re learning together. We’re building in public. That’s part of being transparent is getting more comfortable with just being honest about the fact that people will be wrong sometimes and it’s okay to correct them in public and we respect each other and we trust each other.

But if I didn’t have that kind of trust with the CEO, I’d be having those conversations in private because I don’t want anyone to see this because what if I’m wildly off about, okay, does this new product launch mean XYZ for the industry or am I wrong? I can have those conversations in public, but it all boils down to trust.

Finn Thormeier: Now, last question. Obviously, AI transformation inside of your org starts with the head of the org, with the CMO. There’s so much pressure. There’s so much FOMO. There’s burnout. If a CMO is listening to this, they acknowledge that they are behind, that they need to do more, both personally as well as for their org. And they want to spend the next weekend getting ahead. Where would you point them to? What should they do? What should they read? Which specific resources should they get into? If they had, let’s say five to 10 hours to like get kickstarted, what’s that next thing?

Dan Slagen: The thing I would do is, marketers are notorious for measuring everything. We have a dashboard, a chart, a spreadsheet for everything. AI, I have not seen as many marketers think about how to measure it.

What I would do, especially if you’re leading the team, is I would go directly to your CEO and CFO and get a real agreement and a sense of what are the things that we want to measure with AI? Do we want to look at how fast campaigns go to market or how fast we get value from things we build with AI? Our success rate of pilots, The AI fluency of our people. It’s going to be different for every single company and every single CEO. The easy ones are, okay, token usage and ROI. Fine, but what does that actually mean? Boil it down to specific metrics that you care about and build a dashboard that’s connected to your system and report on it every single week and every single month.

If you don’t have the alignment with your CEO and CFO and then you don’t put that into a consistent structure that you look at every day, your mind is just going to spin and rot around the what ifs, I’m so behind, what do they care about? You’re never going to know. And then if you can keep that updated with your CEO and CFO and say, hey, the things we measured last month were this. Are we still measuring these things? Do we still think this is the most important thing? Maybe you have a new idea. Maybe they have a new idea. But work off a numerical dashboard that everyone’s in agreement on to the best of your ability. That’s a thing that for me has allowed a lot of structure and the ability to ignore a lot of noise.

Finn Thormeier: I love that. Cool. Dan, this was amazing. If people want to learn more about you or Zapier, I’ll link your LinkedIn and the website in the show notes. Thank you so much for taking the time. And that’s it.

Dan Slagen: All right. Thank you.

Patrick Spychalski is the co-founder of The Kiln, a leading GTM engineering agency and one of only six Clay Elite Studios, their highest partnership tier. They recently got acquired by 2X.

Before The Kiln, Patrick helped Clay stand up its early social, events and partnership motions, back when Clay had just invented the term “GTM engineer”.

In this episode, we talk about the state of GTM engineering 3 years in, whether Claude Code is eating Clay’s lunch, when a startup should hire its first GTM engineer, and more.

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We discuss:

* Clay vs Claude Code

* Patrick’s top Clay / Claude workflows and agents: what he would keep if he had to delete everything else

* The newest tools Patrick is currently experimenting with

* When to hire your first GTM engineer and what makes a good one

* Into whom should GTM engineering should report into?

* Why Patrick sold The Kiln to 2X

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Show Notes:

Connect with Patrick:

Patrick Spychalski’s LinkedIn: https://www.linkedin.com/in/patrickspychalski/

The Kiln: https://thekiln.com/

2X: https://2x.com/

Connect with Finn:

Finn’s LinkedIn: https://www.linkedin.com/in/finnthormeier/

Thormeier.co - Founder Brand & LinkedIn advisory: https://thormeier.co/

Mentioned in the episode:

Clay: https://www.clay.com/

Claude Code: https://claude.com/product/claude-code

n8n: https://n8n.io/

Modal: https://modal.com/

Eric Nowoslawski (Growth Engine X): https://coldoutbound.com/

Deepline: https://deepline.com/

BlitzAPI: https://www.blitz-api.ai/

Tom Wentworth (incident.io) episode: https://www.founderbrand.org/p/the-most-ai-pilled-cmo-in-tech-shares

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Full Transcript:

Finn Thormeier: All right. My guest today is Patrick Spychalski. He is the co-founder of The Kiln. The Kiln is one of the leading GTM engineering agencies and clay partners. They recently got acquired by 2X. He also previously helped clay stand up their early social events and partnership motions. I wanted to have him on because I don’t think there’s many people who are deeper in the whole Thank you for coming on the podcast.

Patrick Spychalski: I appreciate you having me. Glad to be here.

Finn Thormeier: How would you describe the, I mean, you’ve been there since basically the, let’s say the dawn of GTM engineering when kind of Clay coined that term, which I guess has been like three-ish years, something like that. How would you describe the state of GTM engineering as of July, 2026?

Patrick Spychalski: Yeah. Yeah, I think it’s at an interesting stage right now where it’s evolved to the point where many people, I’d say even a majority in some spaces of people in marketing and sales have heard about it. They know what a GTM engineer is. It’s becoming a lot more in the vogue, a lot more prominent. Even a year ago, I would say it wasn’t a super popular job role. And now most companies, especially tech companies, are prioritizing it as kind of a core role to hire for. It’s also in an interesting state where the tool stack, I think, is shifting a little bit. Clay initially came up with the term GTM engineering. That was kind of their invention. And I’d still say they’re really core to the work that GTM engineers do. But for a while, I would say that it was really one of the only tools that people were using for a GTM engineer, at least the primary one. It’s now evolving to the point where the Claude Codes of the world, obviously N8N has come out probably into the vogue maybe a year ago or so. It’s getting to the point where the tool stack’s changing pretty significantly. And also, it’s starting to come out with sub-niches of the role where initially, let’s say the broad GTM engineer role is what everybody’s looking to hire for, but now they’re realizing that GTM engineers mean something different for every company. There’s different priorities associated with every business. Sometimes I talk to a company and their main priority is outbound, so they need a GTM engineer who’s got a lot of experience with outbound tooling and the tool stack connected to it. Really want more of like a data engineer, like someone who can go into a data warehouse and sequence all the information to something like Salesforce and create these bi-directional syncs. And so I think they’re coming to realize that, you know, different GTM engineers have different skill sets and need to be hired accordingly. So yeah, it’s at a very interesting stage right now.

Finn Thormeier: How would you describe what’s the leading edge of GTM engineering right now? I mean, I feel like three years ago, just having a clay account and having any workflow in there, that’s like the leading edge. Where are we now?

Patrick Spychalski: Yeah, so I would say like all of the most talented cutting edge UTM engineers I know are building a lot of really interesting infrastructure within Cloud Code. So I think a lot of the really talented ones that I’ve worked with have realized that, you know, you can recreate a lot of the workflows you would build in no code tools in tools like Cloud Code and save yourself a lot of money depending on what the workflow is. But they also realize that these things should not be completely agentic. So for example, if you have an enrichment workflow, the whole thing shouldn’t just be an agent going and finding information and putting it in a document. It’s a big waste of money. You’re using a ton of tokens to do that, and it’ll end up costing you actually more than a tool like Clay would. Clay, I think, is a really good combination of the agentic and the deterministic. So they have to actually rebuild the scaffolding that kind of supports a tool like Clay as well. I would say GTM engineers at a lot of startups I know are starting to try to create their own workflow interfaces and agents. This is a lot more difficult for enterprise companies because of security and compliance reasons. It’s pretty complicated to spin up your own agent and then connect it to Salesforce without there being any problems. But for companies, especially in the Seed and Series A range, I’ve seen a lot of GTMes create their own workflow scaffolding and cloud code and almost become their own host for the workflows that they’re building.

Finn Thormeier: What does switching or replicating things that maybe previously you did in Clay instead in Cloud Code, what does that unlock except maybe some cost benefits?

Patrick Spychalski: I would say the majority of it is cost benefit. There’s a little bit of added positives. I’d say one thing Clay isn’t very good at so far, and I’m sure they’ll improve this, is the relativity component. Let’s say you source Yeah. You can think when you’re using Excel or Google Sheets, you can reference another cell in a table. Clay can’t really reference another cell. So it’s really tough to do that relativity. And that surfaces in a lot of workflows. So things like that, I think, are nice to build yourself or build in something. So there is some unlocked benefit, but for the most part, I think it’s just that place changed their pricing recently. It’s a lot more enterprise forward. They’re really trying to target these bigger companies. And for people who are at Series A or C companies with pretty tight budgets, they were having a lot of trouble justifying the cost, especially to probably the founders or co-founders or CEOs. And so it’s just easier to build it, something like Cloud Code. And again, we’re not really seeing that shift on enterprise. I think enterprise companies will stick with Clay for quite a while, just due to the security constraints and the fact that it’s like a real tool you can procure.

Finn Thormeier: I mean, what is your take on Cloud Code eating Clay’s lunch?

Patrick Spychalski: I think it’s a lot more complicated a problem than people say it is. I see all these posts being like, Cloud Code is going to completely destroy Clay. Clay is dead. Clay is dead. And I really just don’t agree with that. I think Clay has built a really good platform for, and I kind of mentioned this a second ago, but combining the agentic and deterministic aspects of enrichment to create a really cost-effective platform, even with them up They still create a pretty cheap way to run enrichment, build workflows, and safely connect them to platforms. And I really think the safety part is important to hammer on because, like, if you create a Claude agent that connects to your Salesforce, there’s really no guarantee it doesn’t just, like, destroy all the data, wipe it out, not use a sandbox. There’s a million things that can go wrong. Clay really is, One of the safer ways to update your CRM or send messages through a sequencing tool or update a data warehouse because you’re able to visualize all of the outputs before sending it over. You’re not letting an agent just run crazy. It’s just a direct integration with data inputs and outputs. Yeah, I don’t see any large businesses moving over to strictly cloud code anytime soon. I still think Clay is probably their go-to, but I can totally see the justification for startups. One other thing I’ll add quickly is that I think there are some use cases There are cases that are great to be replaced with Cloud Code, and then there’s others that aren’t. So a great example of one that I’ve seen a lot of people effectively replace with Cloud Code is enrichment of lead lists. And so if you have a list of 1,000 contacts that you’re planning to reach out You just want to find their LinkedIn and their email and their phone number. You can just plug that list into Cloud Code, use a tool like an API like DeepLine or something or Blitz API and just run the whole thing and enrich the whole list and send outreach. And I’m seeing that being done really well. People like Eric Nowoslowski, who runs a really successful outbound agency, has essentially just built this huge Incredible automated system that does all of the enrichment and outbound message writing for all, all within kind of this like cloud code built infrastructure. And I think that’s a really good use case, but a bad one would be something like CRM enrichment or even like inbound lead aggregation, anything that connects to like core systems that you really care about.

Finn Thormeier: And besides, so when I asked you kind of what’s the leading edge, you kind of went, you know, a lot of people are moving to cloud code besides the infrastructure. In terms of use cases, so let’s say a very straightforward workflow you might build is you have a website de-anonymization tool, you identify people who visit your website, and then you maybe enrich them, you qualify them, and then you send them some sort of sequence. If that’s the kind of vanilla simple thing, what’s like a recent workflow or agent or clay table that you saw that blew your mind that the smartest people are doing?

Patrick Spychalski: Yeah. So I think you very accurately described the more like, let’s say basic vanilla clay tables. It’s really centered around outbound. A lot of those, like it’s just sourcing lists, doing enrichment and sending out like an automated message. Like that’s what clay was initially made for. People would use it for, for the most part. I’d say as we’re working with more enterprise companies, what we’re seeing is like a lot of these businesses don’t want to get rid of reps. And I think that’s actually the correct decision in many cases, like sales reps still have massive value for reasons we can talk about in a second. But so instead of getting rid of those reps, They’re building these kind of co-pilots that just help enable the work that they do and make them work more efficiently. So, for example, being able to create an agent or like a clawed skill that you can plug into an org and reps can use to source lead lists or run enrichment or draft messaging. You know, because like every rep right now, I’m sure whether... If they’re willing to admit it or not, they’re using a ChatGPT or a Claw to do a lot of their work. It’s helping them source lead lists and find people’s emails and then write messages. And that’s a good thing.

Finn Thormeier: Researching accounts.

Patrick Spychalski: Exactly. Researching accounts. I think it’s a good thing. I truly think that is like a massive value add and it’s gonna make them more efficient, but there’s no standardized way to do that in an org. So people are writing different messaging. They don’t know which tools to use for enrichment. There’s no like structured way to go about these things. And so I’m seeing a lot of, Enterprise.org shift to how can we create these kind of like dynamic clawed plugins that have a variety of skills underneath them that reps can access and use to make themselves more efficient. And there’s so many things that you can do. They could be after a call updating the HubSpot record with all the calls Call notes and information that you found. You could have like a pre-call prep workflow where they can call a thing. It’ll prepare them for all the calls they have coming up for that day. It can be researching accounts and contacts to see which ones are qualified and which ones aren’t. It could be drafting messaging. So there’s a bunch of things that reps can do using just one cloud plugin. And I kind of see that’s where things are going, especially for these rep-enabled workflows.

Finn Thormeier: Yeah, maybe for people listening, I recently interviewed Tom Wentworth, the CMO at Incident.io, and he showed me their cloud setup and they have an applied AI team for the go-to-market team and they’ve built a lot of these cloud skills. I mean, Fable 5 recently got unbanned. I don’t know if you’ve had a chance to play around with it much. Do you see it having any Is there a big impact on any go-to-market processes where you see it being a real game changer?

Patrick Spychalski: Yeah, it’s an interesting question because I feel like the more I think about it, there is a ceiling to the model quality necessary to perform certain tasks. You don’t need Fable 5 to do most of the things we do in go-to-market, Yeah. Yeah. Yeah. Yeah. Yeah. Outbound is inherently a competitive thing. You have to stand out from the other people sending outbound. So you have to have some sort of alpha or some sort of nuance. So I would assume these models can have some improved way of running outbound where it can write better messaging or more nuanced messaging or just have better tonality that resonates with people in that messaging. But I don’t know how much better it’s going to make it. I still think having a human touch to outbound messaging, having somebody write at least like the examples or the scaffolding that surrounds messaging is super important because otherwise it’s just going to sound like every other AI generated outbound message. So yeah, I don’t know. I don’t think it’s going to impact it a ton. It’s a crazy model. Don’t get it twisted. Like it’s an insane thing to use. Like when I’m building stuff for myself, it just can build it so much more efficiently and it can ID it so much better. But for a lot of the good market workflows we’re building for big companies, it doesn’t seem to have that big of an impact.

Finn Thormeier: So you see it more as like the model that maybe builds your, I don’t know, internal tools that you might use in GoToMarket, but the actual day-to-day execution of enrich this account, research this person, you don’t need that for it. Which model writes the best outbound messaging?

Patrick Spychalski: That’s a good question. I’ve always thought, like, you know, I know there’s a lot of debate around this. I’ve always thought anthropics models write the best outbound messaging. And the way we generally work is we don’t write each message one by one for prospects. We’ll usually write some sort of template and then have kind of variables within that template. And so I usually try to use like the highest Opus model. It’s also obviously quite good. I think it’s meant mostly for creative writing. And I would imagine, I haven’t actually used it for this yet, but I’d imagine Fable’s incredible for it because we try to just have this template be really like sound and succinct and well-written. But yeah, I honestly, We use it as a thought partner for writing copy. We’ll have an output of template. We’ll usually make edits to that template. For so long, even when we started the agency, we had copywriters writing copy for our clients for way longer than you would imagine we would because we think it’s really important to have that human nuance.

Finn Thormeier: For the bigger, it sounds like you guys are working with bigger companies now, for those bigger companies and enterprises, how important right now is to them kind of cost management around the GTM use cases when it comes to picking the right model and maybe using some of those open source models for certain tasks?

Patrick Spychalski: Yeah, so you said, sorry, just to recap, because you said cost management, right?

Finn Thormeier: Yeah.

Patrick Spychalski: Yeah, I think it depends on the business. There’s some enterprise companies we work with that are these fast-growing AI startups. They don’t care. They could care less. They’re like, whatever we got to spend to make the output good, it’s fine. But then there’s other businesses, of course, that have a lot more cost sensitivity, and they’re telling us, figure out what the best model is. If we can use API keys for any of these Clay workflows, we want to use them. We want to be really cost-effective. But it’s interesting, like when we first started as an agency, we were working mostly with startups. So we would just talk to these like series A, series B businesses. And they were all obviously, as you can imagine, super cost sensitive. They had raised a round. They want to make sure the round lasts them a while. So they were always telling us like, you know, we need to figure out what API keys to use. We need to figure out what tech to procure. Like focus heavily on cost. But then there have been some clients we’ve worked with recently on the enterprise stage where like, we’ll propose to them like, hey, if you buy this API key, it’ll save you like $5,000 a month on compute costs. And they’re like, Don’t care. We don’t even feel like going through procurement. The procurement for that is going to take so long. Just spend it. It’s worth the speed. We don’t want to have to get through procurement. It’s worth the speed of using the thing we already have. It’s interesting to see.

Finn Thormeier: I see a lot of LinkedIn posts where people talk about their personal cloud setup and they have this super complex thing. They have all the connectors and the MD files with context about them and the super... Complicated, complex, you know, context layer and all of that. I’m just curious, what do you see actually has a big impact on maybe the output that, you know, your cloud or your cloud co-worker cloud code has versus what is just, you know, people creating LinkedIn posts to get, you know?

Patrick Spychalski: Yeah, I think, you know, a good rule of thumb is probably, like, get, like, somebody, like, get the system you see somebody posting on LinkedIn and, like, decrease the complexity by probably 30 to 40%, and that’s probably the right thing to do, you know, like, even I’m also guilty. I remember back when Clay was really on the up and up, I would be posting these absurd workflows. And they’d have some practical value, but you could probably get 90% of the value by decreasing the complexity by 50%. So I was just trying to put the absolute maximum. And I think that kind of applies to a lot of cloud workflows as well. And I think a lot of those interesting things you see on LinkedIn are coming from practitioners that are working at startups or working for themselves. And so they They can create these really complicated things because they know the mapping in their head. So they know exactly how it works. And they have these MD files that kind of just like navigate their own brain mapping of how they should do work. This becomes a lot more difficult when you’re working with big companies. Like, you know, we try to make things as simple as possible. So another, just going back to the kind of the clawed plugin example, like if you’re building a clawed plugin, we’re hoping that like you only have two or three MCP is connected to a given skill. For example, if you’re running an enrichment skill, we want to find one data provider, maybe two, that can cover everything for the enrichment, because we don’t want to find Five or six. We don’t want to have like email waterfalls with like cats. It’s just a lot. Like that’d be so much complexity and so much procurement. So like, for example, like if we found a, like, I think deep lines are great, like, you know, kind of up and coming API that plugs into cloud code and they have waterfalls built in. So like it’s one API for all the waterfalls. They’re like, okay, great. So we’ll use deep line for the enrichment for this component. We try to keep things simple. We try to have one or two APIs to plug into our skills.

Finn Thormeier: For your personal setup, anything that you changed or connected or set up that you feel like actually had a meaningful lift?

Patrick Spychalski: I would say, besides the enrichment providers that I mentioned before, there isn’t anything, I’d say, insane or cutting edge about the skills that we’re building. I think we build them well. I think we have pretty strict rules for how they should work, how they should connect to systems, and that’s usually the main nuance. I don’t have any LinkedIn posts prepared anytime soon that’s like, here are the 15 MCPs that I use every day. It really is just need-based, and most of it can just be used. For example, we have a workflow internally that every time we get off a call, it’ll update the HubSpot record for that company with all the new information. What stage the deal is at, it’ll change the deal stage, it’ll update the notes, it’ll change the next steps, and it’ll do all the updating for us after the call. And it’s really helpful, but it just requires a HubSpot MCP. Crazy about it. Maybe some enrichment if we need it.

Finn Thormeier: If you had to turn off or delete every single agent, cloud, code, routine, clay table you have running and you could only keep three, which three do you keep?

Patrick Spychalski: That’s a great question. I think the first one, and this is maybe unique to us, but I’m sure some people have like kind of adjacent workflows that they use. So we create statements of work at The Kiln when we’re building engagements with prospects. Like when we propose, When we build an engagement to a prospect, we build this really in-depth statement of work about the work that we’re going to do for the prospector slash client. Let’s say, for example, we’re getting on a call with Anthropic and they want to do work with us. We’ll build out this really detailed statement of work and send it to them. We have a really well-made agent that builds the majority of the statement of work. Otherwise, it would take us so long to type all of this out. And it frankly does a better job of summarizing all the calls and emails we had and sequencing that to engagement than we could manually. And I used to have to write these manually. I used to do it myself before the models were good enough. And it took me So that’s great. That’s the first one. The second one probably is the kind of dynamic HubSpot updating skill that we have. Pretty much when anything changes with the prospect, it will now update our HubSpot. And we’re continuously building this out to make it better. But in short, like prospect sends us an email saying something about an engagement. It’ll update the HubSpot record. We have a call with the prospect to update the HubSpot record. We’ll send an email to them, whatever. Something happens, it’ll all update in the record. And that’s so nice because like most sales reps don’t want to spend time updating things manually and they’re And there’s some things that just can’t be captured in a CRM update clay table. Like a clay table doing CRM enrichment mostly is covering like firm graphics and like third party stuff, but first party like new information using an agent to do that is great. So that probably would be the second one is this like kind of dynamic HubSpot updating agent. And the third one, I’ve really appreciated our like pre-meeting prep docs being created by skills now. I don’t know. I’m sure most salespeople can relate to this and probably founders as well. But my calendar is like ridiculous. Like I have like eight hours of calls. I probably have an average of like six to eight hours of calls a day. And it’s like a lot. And many of these I don’t have time to prepare for. Like I’m not like going to sit there and look through like, okay, what did I say this was for? And what’s the background? And having a document that just gets sent to me and I can open it for 30 seconds before a call and read through it every day. Such a value add. And I’m sure it’s a value add for most salespeople who have back-to-backs all day. So those would be the three that I think have been the most valuable for me.

Finn Thormeier: Do you have like a dream agent or workflow that we’re not quite there yet to be able to do that thing, but you would love for it to exist?

Patrick Spychalski: Yeah, I think so. So all the stuff that I mentioned, I feel like is pretty... Like top of funnel. It’s generating proposals and updating HubSpot. I would love an agent that can truly Deal with the annoying logistics of a deal, which is like following up with prospects with like a well-written message saying like, hey, I wanted to follow up on this. By the way, here’s an extra piece of value add that we came up with recently. And then like if they ask us questions about procurement, being able to go into our company’s docs, like look at the procurement information and like truly like a more like agnostic AE bot would be really nice. I don’t think it’s really there and I don’t trust it. I mean, prospects... They’re valuable. I don’t want an agent even slightly messing up the wording of one of my emails, even if the content is correct. I think sales is such an art. It feels such a dance, and you have to make sure that every

Finn Thormeier: How do you think about balancing basically automation with human in the loop? Let’s say for the sales outbound prospecting thing, is this like a pure ACV question where for very high ACVs you just have more human and for very low ACV you do more automation?

Patrick Spychalski: Yeah, I actually say that’s a pretty good way of describing it. Like I’m sure there’s exceptions, right? Like where it’s important to have humans in the loop for certain industries maybe where the people aren’t as susceptible to like emails, maybe you have to cold call them, right? So you have to like cold call these large lists of people in certain industries. But for the most part, I would argue that Uh, the majority of it is ACV based. So when we work with clients who have these big whale accounts that they’re going after, you know, million dollar plus ACVs, we’re like, we’re just going to create systems that can build assets for you better, but like you should be prospecting these accounts. Like we’ll build the slide deck for you. We’ll build the PDF for you. We’ll, we’ll even draft a message that you should probably edit a little bit to make sure it’s perfect. But, um, Yeah, it’s mostly ACV based. I mean, when you’re talking to a company that’s reaching out to whatever, a hundred thousand prospects a month, what are you going to do? Like, there’s not much you can do. You got to kind of automate the message.

Finn Thormeier: So like, should every company have a GTM engineer?

Patrick Spychalski: Um, it’s a good question. I mean, in B2B specifically, I think it’s valuable to have one, but not every company should have one. I mean, especially if you’re early stage. Um, I think, um, A fallacy I see a lot of early stage founders or operators fall into is trying And I don’t even really like using this word because I think it’s a buzzword, but trying to operationalize everything in the beginning, trying to create systems and methods of attack and really try to build infrastructure before you have PMF or you’re still doing founder-led sales. In the beginning, I really think it’s a lot of just brute force and you should probably just accept that maybe your CRM data isn’t perfect, but somebody in your org has it in their brain as to what a prospect is doing and how things are going. So I think there’s a certain stage by which you should probably hire a GTM engineer. And that’s, I think, when your sales team’s becoming more developed. Like maybe, you know, founder-led sales is over. You have like three or four AEs. I think that’s when it starts adding real value. We started working. There’s a company, Modal, we worked with a while ago. And they’re a larger company now because they’re doing super well. So congrats to them. But when they first started working with us, they had like four AEs. And I felt that it was a really good time to hire us because it was like they are now starting to build the infrastructure that these AEs are working in. They kind of have to have systems. And it probably benefits them to have systems. And there’s so many leads coming in now that they have to do something about it. So it felt like a proper time to hire one.

Finn Thormeier: What do you say to the haters who say a GTM engineer is just a RevOps person?

Patrick Spychalski: Yeah, we get that one a lot. And I’d say in a way it’s kind of right. It probably should fall under RevOps if you’re hiring one. It probably should be somebody that RevOps hires. But I think the average RevOps person that you talk to doesn’t know how to use half the tools that GTM engineers use. So it’s really just a tool difference. Like, you know, if you’re a RevOps person and you learn how to use Clay and ClogCode and N8N and connect those to your existing systems, I think you’re pretty much like, yeah. I think RevOps maybe should be given a little more credit than that. A lot of stuff RevOps does is pretty creative and drives direct revenue. I think it’s just a tool difference. Maybe one day it’ll just get usurped into the same thing.

Finn Thormeier: So if we take that company that you mentioned, they have three to four AEs, which I assume that means probably they’re 50 people, maybe they’re around Series A. Would you say that that GTM engineer should report to the head of sales or the head of marketing or someone else?

Patrick Spychalski: It’s a great question, you know, because obviously they never have rev ops people at companies that big, or at least they rarely do. Like, it’s usually just a head of marketing, head of sales. In our case, it’s usually, and this is not the best answer, but it’s usually the person whose workflows the GTM engineer is working on the most. So, like, sometimes both. But a GTM engineer should be pretty... I’d say autonomous in their work. They shouldn’t be getting ordered around. I think especially at the Series A stage, they should not be getting ordered around by heads of sales and heads of marketing. They should be figuring out things to build and maybe even reporting to the co-founder maybe once a month and just saying, this is the stuff I’m building. It doesn’t seem good. It’s adding value. And you should be talking to the head of sales and head of marketing a lot, but I don’t know if they should be ordering you around because sometimes a GTME, especially a strategic one, knows better on what tools to procure and how to build systems than a head of sales or head of marketing.

Finn Thormeier: And then for the bigger companies that you’re working with, do you, let’s say you have a head of GTM Engineering, where do you think is their ideal spot to report into at that stage?

Patrick Spychalski: That’s a good question too. I’d be curious, I’d have to ask some of the people, because I mean, there are definitely heads of GTM Engineering at more mature tech companies. I know I think Cursor has a head of GTM Engineering. Cursor Anthropic probably has their own variant of that. So they have them. I would, like, hesitantly say that they should probably report into either, like, into, like, the head of RevOps, if the head of RevOps, if the RevOps store is pretty big, maybe into the head of RevOps, or into the head of Ops, actually, like, if they have a good head of Ops. The problem is, reporting to head of marketing or head of sales is a big issue, because, like, Marketing and sales notoriously clash. And so like, if you report to any of them, they’re going to just prioritize their work over the others. And they’re also probably going to, there’s always the blame game of like marketing, sending us bad leads and sales is saying that, and then marketing saying, well, sales just is just bad at closing and we’re actually sending them good leads. And so there’s always like this kind of conflict between the two. And so I don’t think you should report to either. It should probably be to somebody who’s optimizing for efficiency or well-built systems. Um, And so it’s, it’s almost like somebody either separate from them or above them. I mean, obviously like if you can get them to report to the CEO, then it’d be great too, but you know, CEO is busy. Um, but it should be somebody who like, isn’t in the middle of that battle, I think.

Finn Thormeier: Yeah. I think you guys even help place GTM engineers now with companies. What, how would you describe the, the hiring profile of the right kind of person to be a GTM engineer?

Patrick Spychalski: Yeah, I’d say it’s probably one of our most in demand services, just because everyone’s trying to hire a GTM engineer, and they’re really hard to hire for two, I think, core reasons. The first is that There’s not a massive talent pool for it. It’s pretty tough to find a really talented one. And if you want to hire one, they’re really expensive. So talent pool is pretty low, especially at the price you’re probably wanting to pay for one. And then the second is that, as kind of mentioned before, there are so many different kinds of GTM engineers. There’s ones that handle more RevOps-based work, marketing-based work, sales-based work. And so there’s no perfect profile for one, which is why we offer the service. I mean, the first thing I asked myself when we were thinking about offering this is like, Why would we do this when we need to hire GTM engineers? We’re cannibalizing our own business if we’re doing this. And then the more I thought about it, the more I was like, Like there’s a certain kind of GTM engineer that should be placed at some companies. And a lot of those are not people that work for us. And so we’re very picky about the clients we bring on. They have to be hiring a GTME that isn’t the sort of one we would hire because otherwise it’s completely a conflict of interest. Like, you know, whatever. If like, I don’t know, like Google tried to hire us to hire a GTM engineer and it was just a person who would work well for us, I’m probably going to prioritize us. And I don’t want to do that. So we have to find something to use. He’s looking for more of a specialized one. I think our people are really great all around GTMEs, but we try to find people that are hiring. We really need one for RevOps, or we really need one for sales. And the profile is usually someone who has a very hacky kind of personality a lot of the time. GTM Engineering, they don’t have a lot of... You know, well-known courses for it. It’s not something you learn in school. It’s not something you go to class for at college. So it has to be kind of a self-starter role right now. You have to kind of seek it out or have to have found out about it and decided to make the career pivot. So there’s a lot of real self-starters in GTME. The ones that we found are really great are ones that started in a technical role. They’re specifically good for rev ops based GTME roles. So people who were software engineers or forward deployed engineers and decided to become a GTME because it’s so natural for them to learn this stuff like clay is easy when you’re when you’ve learned code, like not a hard thing to learn. So, and then for more like sales-based GTM engineers, like AEs, especially like enterprise AEs who worked at a company that sells a technical thing seem to be really good. So like, you know, like I’m sure like a Databricks AE would be really good at being a GTME because they understand all the technical nuances of like a Databricks product and they have to understand that stuff and they know how to sell. So they know the plight of a sales team or a salesperson. So they tend to be really good. And then someone from MarOps who decided to become a GTME is really good, too, for marketing-based go-to-market engineering work. So somebody who worked in MarOps knows all the tool stack and then decided, I want to learn clay and cloud code and N8N seems to be quite good. So different profiles for different types of roles.

Finn Thormeier: I mean, it obviously depends on the kind of use case that you want to apply there, but it sounds like, I mean, there’s GTM and engineer, in GTM engineer, and it sounds like almost you want to lean more towards an engineering person who then learns GTM rather than a GTM person who now needs to learn systems thinking and that sort of thing.

Patrick Spychalski: Yeah, I think depending on the use case, like again, if you’re running an outbound motion and you’re hiring a GTME that’s doing outbound, Like it could be better to find an AE or an SDR who became a GTME because they understand outbound, right? But for any sort of like rev ops, like for CRM enrichment or any sort of like rev ops based work, I really find the engineers are better at figuring that stuff out because they understand systems thinking already. And for complex systems like that, it tends to work out better. So that’s why I say like there’s no one profile. I think it depends on what you’re trying to hire them for.

Finn Thormeier: I don’t know how to frame this question, but where do you think the kind of alpha or mode is? I think there’s some level of what’s happening is that GTM engineering is a buzzword. Companies just want to do it because they heard it and they’re like, we’ve got to do it, but they don’t maybe fully understand it. Where’s the alpha here? Is it just having one? I don’t know if that question makes sense to you.

Patrick Spychalski: No, I think I kind of get the idea. I think there’s an inherent issue with just deciding to hire a GTM engineer for the sake of it. That’s not, I don’t think, a good idea. And there are so many companies that I’ve spoken to and often ones that we tend to disqualify that are just like, we need AI, GTM engineers, AI, we need to hire this AI person. And usually that’s just coming from the higher ups, like whatever the board of the CEO being like, we need AI and that’s going to solve our problems. Sometimes there’s a big strategy gap. Sometimes your reps aren’t writing that great messaging or they’re not calling the right people. There can be a lot of real Creative strategy gaps in a go-to-market system that won’t be solved by a GTM engineer. When you hire a GTM engineer, you’re not hiring an AI wizard that can solve all your problems. You’re hiring somebody that can build systems to accelerate things you’re already doing well. We never work with a company. If a company comes to us and they’re like, hey, we want to build a scaled outbound motion. We want to get the messages our SDRs are writing. We want to automate that creation of the messaging. We want to send them at high volumes. It would be foolish to take that on if the messages suck and they’re not getting responses. Zero times 100 is still zero. Why would we scale that messaging? We would never take a client like that on. I think often there’s this gap problem where they just think AI will solve our problems and they likely won’t. You should probably just think a little bit more.

Finn Thormeier: Yeah. And I’m curious to get your take on this. I’ve talked about this with Tom Wentworth and he’s very deep in the whole Clay and Claude Code. His take is basically that right now it gives them an edge just because they’re deeper in it and more advanced in it than most of their competitors. They’re automating things that they’re not yet automating. They’re saving their AEs times in places where their competitors are not. Part of that is just because these tools have gotten easier. But they’re still kind of complex. But very soon this will be commoditized and it will be very easy to build any workflow and you just write one prompt and it will build you whatever you want to have. And so everyone will have access to these skills or agents or workflows or whatever it is. And then the real differentiator will be Brand or taste or whatever people say. What’s your take on that in general? Will this idea that you can build a very cool cloud code setup and clay table all be commoditized and everyone will be using the same setup and then it still just comes down to who has the better product and who has more taste?

Patrick Spychalski: Yeah, I think that’s partially correct, but I would say my overall take on this is as follows, which is that tech will always be commoditized to some extent. Whatever’s cutting edge will eventually be caught up to. The Founder Brand. I think Tom is correct in the sense that it’s a massive advantage right now for them to be doing this stuff over their competitors if their competitors aren’t doing it. And frankly, this is why we often target kind of boring industries to do our work with because if we implement it for them, it will be a massive competitive advantage for a pretty long time. I’m sure everybody’s talked to those companies that are just absolutely archaic. They haven’t moved past a certain tool in 25 years. Beating them, if you’re one of their competitors, is pretty easy if you have the right tech. But to your point, eventually it’ll get caught up and it’ll eventually get commoditized. And then in commoditized spaces, for example, SaaS is getting really commoditized with all of this. All the SaaS companies have the same tool stack at this point. They have clay, they have cloud code, and they’re all doing pretty similar stuff, depending on the SaaS, I guess, but for most B2B SaaS businesses. Then the main competitive edge is creativity. And Clay kind of had this concept marketed for a while with like GTM Alpha and the GTM Alpha is truly like your own creativity to create these like really valuable plays. And I still think that that tends to be true. You can’t have agents do this stuff for you. Like I think there is this like, I don’t know how to explain it, but like human ingenuity and intuition that can really create Outbound plays that agents never could. And so I think that’s where the real creativity lies. Like if one company is sending a pretty boilerplate outbound message just saying like, hey, I saw you raised a round recently. Here’s our offer. That’s a classic. Another company is sending this beautifully done, AI-generated, branded PDF, doing an audit of the company’s existing systems based on information that they enrich. The other will obviously win every time, and I think some variant of that is always important to keep on top of mind.

Finn Thormeier: Are there any new tools that you’re playing around right now that you’re experimenting with or that will be inside of the LinkedIn posts in six months?

Patrick Spychalski: Yeah, it’s a great question. I mean, I think I’ve always had pretty like unidimensional LinkedIn posts every time I put them up. Like in the sense that I’ve never said that there’s 50 tools you should use. Like I’ve only really ever talked about Let’s say three heavily, which is Clay, N8N, and Cloud Code. And that’s because every time I’ve used one of those three tools, it’s felt like a real paradigm shift and worth talking about. It’s not just some new data provider that’s going to give you alpha for a week. I really think that the infrastructure problems are the ones I like solved. And I really do see the future being... Like plugins to the like cloud codes and codexes and Gemini’s of the world. I still think that those plugins are going to be what’s super valuable. And right now there’s not really one that I think solves every problem. I think, you know, I’m sure Clay at some point will develop their own kind of like MCP that plugs into cloud code so you can build workflows through it. There’s again, like the deep lines and blitz APIs of the world that give you enrichment data, but there’s not like, Uh, not one great like scaffolding layer. I think that plugs in the cloud code yet. That’s really been built. So until that gets built, I have nothing new. I mean, I’ve been talking a lot about cloud code and different APIs that plug into it, but nothing like super fundamental besides the actual tech behind cloud itself.

Finn Thormeier: Now last, a selfish question, uh, as an agency owner, what, uh, can you recommend selling your agency and what tips do you have to sell your agency?

Patrick Spychalski: Yeah, it’s, I mean, I think selling your agency really has to be kind of a, like, personal decision. I actually think, like, you know, obviously there’s a lot of financial decisions that are, like, sub-decisions of the overall decision, but the question should really be, like, Fundamentally, how do you want to live your life for the next few years? What do you prioritize? And how do you see the vision of your company being materialized down the line? So for us, there was a lot of questions. The first question was, You know, like where, where do we think we could take this if we built it ourself and does it kind of align with our own goals of what the company should be? And so for us, our goal was like, let’s work with all the biggest companies in the world on doing GTM engineering and just stay at the cutting edge. I frankly never had like, at least since we started the business, a dream to hire like 500 people and have this mega agency myself. Like that doesn’t appeal to me.

Finn Thormeier: I don’t think anyone dreams of that. That sounds like the worst.

Patrick Spychalski: Maybe, but you know, the problem for me, at least, was that, like, I think we have such talented people on our team. I think, like, I get fired up when I talk to the people on our team every day because I just think they’re so good, and I frankly think they’re all better GTM engineers than me, which was my goal when I started the agency. I wanted everybody on our team to be better than me, and I think that’s truly there. And when you hire, when you have 500 people at an agency, it’s really hard to achieve that same level of quality. I mean, it’s pretty much, it’s nearly impossible because, you know, like you have to have like 500 people that you’re paying like salaries to them that they could easily go find better salaries elsewhere. So like, yeah, there’s like the competitive, like, uh, like. Who do I work with? There’s so much bureaucracy and really talented people don’t want to work in bureaucracy. They want to be free. They want to be able to do whatever they want. They want to be able to have side projects. And so you just can’t have a really well-built agency with the same density of talent I think we have. And so I came to that realization and I was like, Okay, well, like, what do I really want then? Like, and it’s probably to work with the biggest companies in the world and keep working with these really smart people and keep doing cutting edge work. That’s what excites me. Like, I think for everybody on our team, building really cutting edge stuff is what excites us. And like being at the front line of GTM engineering, I think is like a legacy we’re all trying to achieve. And so when I came to that realization, And then 2X approached us. I pretty much said, as long as you let us keep our core group, continue slowly hiring and building the agency and working with really cool, exciting companies and give us the resources to do that, it felt like an enticing opportunity, which was just like, you give us a bunch of money to grow the thing and do the things that we wanted to do. Because we were bootstrapped. When we had a marketing initiative that cost $50,000, I was like, man, I could either buy a Toyota Tacoma or I could do this marketing initiative. It’s kind of a tough one. I do really like the Toyota Tacoma. I probably won’t do the marketing thing, but when you have real budgets from a larger company that’s pushing you to do a thing, it feels a lot more powerful. We now have this larger entity backing us and allowing us to grow more. Um, at the way we want to grow and hire really talented people. And that, and so that was kind of like the lifestyle decision we decided on is like, I don’t want to be a CEO of a 500 person agency. I want to run a small core group of people that are really good at what they do. Um, and as long as I can get a decent exit outcome from it, then like, it’s, it seems like a pretty good, uh, pretty good deal. And then, and then hopefully it’s a good deal to two X. Cause you know, as long as we keep growing this thing and adding value and adding enterprise value, then hopefully they get their good end of the deal. And it ends up being hopefully like a deal for, for, for both of us and ends up working out.

Finn Thormeier: So besides that, meaning to keep staying at the leading edge, work with the biggest companies, anything else that’s kind of next for the kiln?

Patrick Spychalski: I’m unsure. I mean, our recruiting offer has been growing a good amount, so we’re pretty pumped about that. But I think... We’ve always tried to stay pretty core to our offering because I think it’s something we do really well and it’s something we’re known for. And so I’ve always been really afraid to stray away from that. Our offering is just, we’re going to give you some really talented people to build really cool projects for you. And we feel we have the best collective GTM engineering talent in the world. So we’re giving you that as essentially a service and you get to pay us monthly for it, which is a pretty good deal. Yeah. We always have people on our team who are building SaaS products internally and building cool tools and cloud code plugins. I mean, the stuff our team has built, if it ever was productized, I’m sure somebody would make a lot of money from it. But I tend to let the team develop that themselves. If they want to use it as their own product, they can roll it out. And we use it internally and we roll it out to our clients all the time. So I’ve always been really afraid to like,

Finn Thormeier: All right. This was awesome. If people want to check you out or want to check out The Kiln or 2x, all of the links will be in the show notes below. Patrick, thank you for joining.

Patrick Spychalski: I appreciate you having me. Appreciate it, Finn.

This episode is a bit different. A little over a year ago, I listened to a podcast between Jonathan and Jason Fried, the co-founder of Basecamp/37signals. I had known Jonathan for a while, and I’m a big fan of Jason Fried, but the episode was very different — it was almost like a therapy session. Jonathan had reached out to Jason for some general business and life advice, and instead of keeping it private, he decided to publish it. At the time, I got a ton of value out of it.

So in almost a “déjà vu” moment, I’m doing something similar here, but with the roles reversed: Jonathan giving the advice, instead of asking it. We recorded this a couple weeks ago when I was trying to figure out where to take Project 33. Given that Jonathan had built a large agency but then also pivoted into other, more scalable offers (he’s the CEO of AJ&Smart and facilitator.com), he felt like the perfect person to ask for advice.

And if you’ve seen any of my recent stuff on LinkedIn, you might’ve seen that I pivoted the podcast and launched my advisory firm thormeier.co A good chunk of that was kicked off and inspired by this conversation.

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We discuss:

* Why I’m the one getting coached this time

* Four ways to get a dream out of your system and “the tiniest announceable version”

* The agency/offer ladder: from DIY (do it yourself), to DWY (done with you), to DFY (done for you)

* 25% close rate: anything higher means you’re too cheap

* “If you have to sit down and do 10 hours of work to be successful, then you’re just doing stupid s**t”

* How to make a 500-listener podcast worth $100k

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Show Notes:

Connect with Jonathan

Jonathan’s Linkedin: https://www.linkedin.com/in/jonathan-courtney-4510644b/

AJ&Smart: https://ajsmart.com/

Facilitator.com: https://facilitator.com/

The Unscheduled CEO podcast: https://www.unscheduledceo.com/

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Connect with Finn:

Finn’s LinkedIn: https://www.linkedin.com/in/finnthormeier/

Thormeier.co - Founder Brand & LinkedIn advisory: https://thormeier.co/

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Mentioned in the episode:

Nat Eliason’s essay on de-atomization: https://www.nateliason.com/blog/de-atomization-is-the-secret-to-happiness

Built to Sell by John Warrillow: https://builttosell.com/

Sprint by Jake Knapp: https://www.character.vc/sprint

Skool: https://www.skool.com/

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Kyle Poyar is the founder and writer of the wildly popular Growth Unhinged, a newsletter with over 85,000 subscribers about pricing, monetization and GTM. He also has over 110,000 followers on Linkedin.

He started the newsletter in March 2021 as a side project and went all-in about a year ago. Since then, his one-person business is doing over 7-figures a year, between brand partnerships, subscriber revenue, and advisory work.

In this episode, we talk about how to build & monetize a newsletter, including how Kyle tests every newsletter idea before writing it, why Kyle’s pulling away from Linkedin, leaving Substack for beehiiv, and more.

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We discuss:

* How Kyle started & grew his newsletter from zero to over 85,000 subscribers in 5 years while having a full-time job

* How Kyle validates newsletter ideas before writing them up

* How he creates his graphics, which are a large part of his success/shareability

* Why Kyle is pulling away from Linkedin even though he has 110,000 followers

* The math behind running a 7-figure/year solo creator business

* Why he left Substack for beehiiv after 5 years on Substack

* Why subscribers you get from the recommendation feature are mostly “garbage”

---

Show Notes:

Connect with Kyle:

Kyle’s Linkedin: https://www.linkedin.com/in/kyle-poyar/

Growth Unhinged: https://www.growthunhinged.com/

Mostly Growth podcast: https://www.growthunhinged.com/podcast

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Connect with Finn:

Finn’s LinkedIn: https://www.linkedin.com/in/finnthormeier/

Thormeier.co - Founder Brand & LinkedIn Advisory: https://thormeier.co/

---

Full Transcript:

Finn Thormeier: Alright, my guest today is Kyle Poyar. He is the founder and writer of the Growth Unhinged newsletter where he talks about monetization, pricing, GTM growth and other practical advice for B2B startups. He started it in March 2021 when he was still working full-time at his job and it has since then grown into one of the most popular newsletters in the B2B space with over 85,000 subscribers. He is also a prolific writer on LinkedIn with over 110,000 followers. His background is in Venture Capital where he was an operating partner at OpenView, which invested in companies like Datadog and Calendly, as well as, found this out during research, a company called Project 44. My company is called Project 33, so clearly they have the edge on us. Matter of fact, we’re 25% worse than them. Kyle is also the host of the Mostly Growth podcast and he advises B2B startups on growth and monetization. Kyle, thank you for joining and anything to correct or amend there in the intro?

Kyle Poyar: Thanks for having me on. No, I think you got it right, but it’s been interesting that I started the newsletter while working full-time in VC, but it’s grown big enough to kind of support an independent solopreneur business, which is pretty cool.

Finn Thormeier: Nine months ago, right? Nine months ago, you went kind of fully on this business?

Kyle Poyar: Exactly. So it was August of last year, of 2025, that I made the decision and then really went in earnest in September.

Finn Thormeier: There you go. Okay, so you started it in March 2021, and then you were full-time at OpenView. In those five years, it’s about five years, you’ve grown it to 85,000 subs. Before we talk about the lessons, I’m just curious about your writing process. What does it look like? How much time do you spend on each thing? How do you pick topics? Just start where you want, walk me through your process.

Kyle Poyar: So the starting process I had is probably the most relevant for anyone that’s thinking about starting a writing practice. I began on LinkedIn actually before I ever had a newsletter — wrote long form content around COVID. Very active on LinkedIn. And I would realize I’d have these pieces. I mean, a lot of my posts would fall flat and have no engagement, but I’d have other pieces that would do quite well, but I would run into character limits, or I’d post something and then it was impossible for someone to find a couple of weeks later. I’d also get DMs from people that were smarter on a topic than I was. And so I was like, I feel really constrained by LinkedIn.

And so what I decided is not just that I would throw out LinkedIn for a newsletter, but I would test ideas on LinkedIn. I would see what my audience cared about. I would take that as signal to go write a deeper piece on a topic, or sometimes string together multiple LinkedIn posts to turn it into a piece. And then I’d promote that back on LinkedIn. And so it all became a flywheel where for me, it wasn’t like I’m going to have this brilliant idea and write about it and then post. I think about content as a place where writing and distribution need to be on equal footing, and where the best practices create a flywheel where you’re building for and with a community. And I think that’s what can make a newsletter really stand out.

Finn Thormeier: And if I remember correctly, back then when you started on LinkedIn, you were an operating partner. So you were working with the portfolio companies at your VC firm on their go-to-market strategy, pricing. And I think you were kind of talking about lessons, takeaways, insights, things that you were seeing with those portfolio companies.

Kyle Poyar: Exactly. Exactly. And so for my content calendar, and even for the LinkedIn content calendar, often it was pretty informal.

Finn Thormeier: Did you back then have like a, “I’m going to post every single day” or “I’m going to post twice a week,” or was it just completely ad hoc whenever something popped into your head?

Kyle Poyar: Back then it was pretty ad hoc. I mean, some of these people post literally daily, including weekends. I don’t know how you have the stamina to do that. I’ve always been long winded and I just don’t have enough good ideas that I want to go that deep about every single day. My cadence over time has been about two to maybe four times a week — almost never publish more frequently than that, unless something is like really wrong with me. And it’s pretty ad hoc. I like to post multiple days a week. And so if I don’t have any ideas, I might find something from my archives and kind of tweak it or tailor it. But generally it’s not super planned far in advance. I try to keep things fresh.

There’s one point in my career when I used a scheduling tool, actually the native post scheduling tool within LinkedIn. And then I realized it was either the content was outdated, or maybe it was LinkedIn penalizes you for scheduling content — I don’t exactly know what it was, but I felt like that was actually having way worse results than publishing fresh insights. I almost always post in the morning. I do find that that’s when I have my best ideas, I’m sharpest, but also that’s when people are most engaged. Sundays work surprisingly well. I think there’s just a lot less competition and you get all the LinkedIn diehards on Sunday, but then your post is the first thing people see on Monday too. So I do find that that works quite well.

And I will say one thing that works quite well for me is I think about the visual as much as the text. I spent six years in consulting and so I would make decks — I’ve always thought in terms of slides — but I would translate that to LinkedIn infographic style visuals. And that’s become a bit of a signature, a calling card for me. But those visuals perform far better than text only posts. They’re way easier to share. I think it’s partly to do with, it feels save worthy — like, oh, I should save this and maybe bookmark it for a presentation I’m working on, or I can share this with a friend or colleague. I think it’s also something that drives more dwell time. These are generally not super simple infographics. They’re pretty complicated ones, which means people are actually spending real time reading it. And that means they’re spending more time on LinkedIn, which means LinkedIn can get more ad dollars. And so they’re going to push that harder. And so these dense infographics are the starting point for most of my posts.

Finn Thormeier: How much time do you spend on an infographic?

Kyle Poyar: 30 minutes, maybe. I actually do them all by hand. I have got a Google Slides template that was made by a great designer when I was at OpenView, and I’ve kept that template and made some tweaks. But it has a couple of fonts in it that are out of the box in Google Slides, a couple of colors, nothing fancy. But I literally will make the visuals myself, which feels weird to be doing point and click in 2026. Some people would say, is that really the best use of your time? But honestly, if you get the visual right, that can make the difference between a post being viral or not. I reuse posts in speaking decks when I go out and do public speaking. I’ll put those visuals in my newsletter articles. A great visual is so valuable that it feels very hard for me to give that up. But yeah, I’m not taking hours and hours on it.

Finn Thormeier: Do you start with writing the text and then later you find a graphic that works for it? Or do you start with the graphic and then write?

Kyle Poyar: Oh no, the graphic is the starting point. And then I write something to go with it. I think of a hook that I think is useful. And then the graphic is so dense, there’s actually a lot of writing in the graphic itself. And so I often copy and paste from what I wrote for the graphic into LinkedIn. It’s kind of like, I mean, if you go on Instagram, people put captions with their posts, but realistically, you scroll through Instagram for the image or for the video. And I think people do similar things on LinkedIn where the hook has to be strong, but the visual also has to be quite strong.

Finn Thormeier: Which visual are you very proud of that we can a little bit use here as an example?

Kyle Poyar: You can take the pricing one. That’s the one you’re hovering on right now. This was a pretty basic one, but it’s rare for a pricing LinkedIn post to go viral. Over 3,500 reactions, over 200 shares. And this is something I didn’t pay to boost at all. I just was seeing people really struggle with pricing for AI. And as much as I thought I had some good guidance for people, really the reality is every company was kind of all over the map in what they were doing. And I just wanted to highlight some examples of really interesting pricing models from the big players and from others. It gets almost used as a brainstorming thing probably that a lot of teams can share internally to be like, hey, here’s a bunch of very different examples from a bunch of oftentimes well-known brands on how they do it that can get us started on how we can think about changing our pricing model.

Finn Thormeier: Plus you obviously have quite a few recognizable logos in here. So I think that also helps.

Kyle Poyar: But you can see this is not done by a designer. This is something I literally put together in Google Slides. The resolution could be higher. I actually think that overpolished stuff looks too corporate-y and people actually get turned off by that. So something that feels a little bit more rough works better.

But yeah, I mean, to me, the best content that’s going to do well has to either educate or entertain. And the entertainment is a very high bar. Some people do it extremely well. Like Elena Verna has such amazing memes and, you know, hilarious content. I’m not a standup comedian as much as I would love to be. And so for me, that educate bucket needs to be there. And so I need to fit into: this needs to be a how-to guide or something that a reader can take and immediately do something with what they read. And if I’m not at that bar, if it’s just like information, that’s maybe like, oh, I learned something — that’s not really enough anymore. News isn’t enough. Information isn’t enough. It really needs to educate and teach someone how to do something.

Finn Thormeier: What’s the correlation between — so when your process was, hey, I post something on LinkedIn that I learned working with the portfolio companies or that I kept repeating myself and this resonated, let me make a newsletter out of it and expand on it — how close is the correlation between “this did well on LinkedIn” and now expand on it in a newsletter and it did well too? Is it like 100%? I’m just kind of curious on that.

Kyle Poyar: You know, it’s a positive... I don’t know what the exact correlation would be, the R squared, maybe like 0.6. I don’t know. Don’t hold me to that, but it’s not a perfect correlation. There’s definitely things — I wrote this LinkedIn post about customer success: don’t blame customer success for your churn problem, here’s all the other things that are probably causing your churn problem. That did incredibly well on LinkedIn. I think every customer success person probably liked it so their boss would see it. None of my readers cared about it. I think maybe it was because a lot of that was not necessarily totally new information, or maybe they didn’t have a big churn problem, or they just see me as more marketing and go-to-market focused rather than customer success oriented. I don’t know what it was, but that one fell completely flat when turned into a newsletter.

I do find things that don’t resonate at all. So screening out things that no one cares about, that’s the most useful bit, because then I’m not spending hours and hours writing a full newsletter post about something I already know is not going to do well. And at the very least, even if the newsletter post doesn’t perform as well, I’m going to be able to repost that same kind of idea on LinkedIn to amplify my newsletter. And I know my second LinkedIn post will actually probably do quite well. So that correlation — if it did well on LinkedIn the first time, having it do well on LinkedIn the second time, that’s maybe an R squared of 0.9 or something.

Finn Thormeier: Is that still your process today? You said this was kind of how you got started.

Kyle Poyar: So that was my process for several years. I’m no longer an operating partner. And so I still do that sometimes, but honestly, I’ve been really disillusioned by LinkedIn. And so I’m kind of moving away from LinkedIn right now. And I also just have... I’ve published more than 200 newsletter editions. I think I’m coming up on 250. So at this point I have themes that I know my audience cares about. I try to have a mix of content that touches on different themes.

Finn Thormeier: You said you’re disillusioned by LinkedIn. Tell me more.

Kyle Poyar: I mean, LinkedIn used to be fun in 2020, in COVID times, but that’s when I really started getting active. I did it because I wasn’t going to events. I wasn’t meeting people. And I actually met real life, very smart people on LinkedIn. They would maybe show up as someone commenting on a post, or maybe they’d DM me as a result. We’d hop on a video call. Some of the best networking connections I have came from that period.

And now I’ll write something, no matter how good I think it is, the comments are like 80% garbage LinkedIn slop comments. The engagement on content has fallen a lot compared to what it was before. LinkedIn seems to be prioritizing content that is of mass appeal. I think they’re even piloting showing things like how much of your content is shown to in-network versus out-of-network. But I have over 110,000 followers. My followers don’t consistently see my content. It’s like the content is shown to random people who might or might not care about my stuff. And that means I need to have hooks that are basically bragging about myself or telling people that don’t know me who I am. I like to have 201 level content — I don’t write for a beginner audience — but to do well on LinkedIn these days, you kind of have to be doing 101 level stuff. And that’s just way less fun all around for me. And there’s not a whole lot in it, except for yes, the occasional post does quite well and it drives a lot of newsletter subscribers even still. So I’m kind of forced to be on it. I’ll also scroll it occasionally to get inspired by what’s working for other people. I’ll use that to find some experts that I’ll interview for my newsletter or some case studies to share. But even that’s gone downhill, because my feed just — I rarely see that kind of good rich post on LinkedIn anymore. I see like AI slop stuff.

Finn Thormeier: And do you think that is — I mean, there’s the kind of AI slop automated comments. I definitely see that too. And it just ruins your experience, because I feel like it makes you question every single comment. Some comments are obviously AI. Some comments are obviously not AI. But then there’s a lot in the middle where you’re like, this could be AI, but this could also be an actual person trying to ask me a question right now. And I’m trying to decipher, is this AI or not? Because if it’s a real person who wants to ask me a question, I want to answer them. But if it’s someone who automated this stuff, I don’t want to answer them. But it makes me second guess a lot of comments anyway. So that’s obviously happening. There’s a lot more content happening. And then it sounds like this algorithm change, that it’s less and less of a follower based feed and rather an algorithmically driven feed. When did that shift happen time wise, where you’re like, I’m just not enjoying LinkedIn anymore?

Kyle Poyar: Really, it’s been the last six months. I mean, I’ve always been hot and cold with LinkedIn, because there is a real creator burnout phenomenon where I could have a couple bangers in a row and be feeling on top of the world, even though I’m like, LinkedIn doesn’t matter, LinkedIn doesn’t matter. But really, from a psychological standpoint—

Finn Thormeier: The dopamine is real.

Kyle Poyar: Yeah, it has an ego effect. But then you go a couple posts that are full crickets, no one cares at all. I’m like, I have 110,000 followers, but I got like five likes on something. Did I completely lose it? But the highs and lows are really challenging to deal with. And so that’s been the case for a while, but this slop era has really been since probably January of this year. Everything’s like slop or hype posts, or they just feel — it lost the fun that it used to have. We’ll just say that.

Finn Thormeier: Given that you want to move away from it — I mean, I think I saw a newsletter by you where you talked about growing the newsletter, and I think LinkedIn was your biggest or second biggest kind of growth driver in terms of subscribers. Given that, how do you think about it? Has the newsletter now reached a scale where it’s self sustainable to some extent? Or how does that affect things?

Kyle Poyar: Yeah, you know, as much as I would love for my mental health to be off LinkedIn, it is probably the most powerful growth lever that I can control. And if you think about what options you have available to grow, there’s some platform growth opportunities. So Substack has recommendations and they have Notes, which is kind of their LinkedIn. beehiiv has a recommendations feature as well. And so that’s a core part of growing any newsletter, I think. But it’s a little bit more algorithmic. It’s tied to the platform, tied to your relationships with other authors. So definitely recommend — that’s really low hanging fruit acquisition for anyone growing a newsletter.

Then there’s paid. And so you can pay on beehiiv for boosts, or you can pay on third party platforms like Meta or like LinkedIn. I am doing some paid testing with boosts via beehiiv that are coming in at decent cost per acquisition. I haven’t really scaled that channel.

And then otherwise you’re looking at word of mouth, which is a really fantastic channel, but hard to measure, hard to control. I get a lot of growth through just readers forwarding the newsletter, dropping it in Slack organically, sharing it on LinkedIn. That’s fantastic. But I’d love for every piece I write to be a banger that people organically share, and it’s just hard to fully rely on that as a growth channel either. And so when you look at things that you can control that are not that expensive, LinkedIn is one of the few channels out there. I do think AEO and SEO has some low hanging fruit and that’s something that I neglected for a while. And then my own referral program for readers has been another area. But yeah, LinkedIn is the single largest growth driver in terms of both my direct traffic sort of attribution, and then I now have a survey of new readers when they sign up — I have a “how did you hear about us” field and LinkedIn is number one there too. And so I’m just like, that is so organically tied in with the content I’m writing. These are inherently shareable on LinkedIn. I’ve got a large LinkedIn audience. I’ve got to keep relying on that even if I hate it.

Finn Thormeier: I mean, it is interesting. I had Emily Kramer on the podcast a couple of weeks ago, who has one of the biggest Substacks, the MKT1 newsletter. And I think she said her biggest source right now is recommendations. And for her, LinkedIn is a surprisingly small part. Where she even has more subscribers on Substack than she has followers on LinkedIn.

Kyle Poyar: I would be very careful with recommendations. They’re a great source of growth. And at one point, about half of my new subscribers came that way — I had over 500 publications that were recommending Growth Unhinged. And essentially what this looks like is, in the signup flow, someone goes to sign up for another newsletter and it’s like, hey, this writer recommends these 15 other publications. Do you want to subscribe to these too? And a lot of people click select all, and then all of a sudden they’re auto subscribed to 15 newsletters they know nothing about.

It’s great for growth. Don’t get me wrong. If you care about the vanity metric of your number of subscribers, it does go up. But often deliverability is really bad with those subscribers. Unsubscribes is really high. Substack as a platform doesn’t really let you dig into unsubscribes very well or get much visibility into the subscriber quality by channel. But realistically, a lot of the recommendations oriented subscribers were garbage. And that’s why even Substack started tightening up that growth lever a bit. And that’s why I was seeing less subscribers come from it. But I also just think that was a channel that was fantastic in like 2023. And then like every channel, it kind of got saturated, where instead of you having a handful of other writers you’d maybe swap with, I see some publications that have like 60 publications they recommend, because they’re gaming the algorithm. And then there’s some reciprocity where you’re like, maybe I want to recommend them back. But show me — I want someone to show me what’s the delivery rate and the open rate among the subscribers they got through recommendations, especially for people doing this gaming. It’s a vanity metric. The reality is there’s not a lot of real quality subscribers to that channel. And your own channels — if you get subscribers through LinkedIn or direct to your website or through word of mouth, there’s an affinity to your newsletter. They subscribe purposefully for your content, and that’s going to be a way healthier subscriber.

Finn Thormeier: Now, I have similar feelings around the LinkedIn part and the algorithm, and that it’s less enjoyable. I’m just curious — so I’ve been playing a lot more with this idea of a newsletter. But I’m also aware of this idea of grass is always greener. So I’m just curious, you have the perspective on both, and actually having a big audience on both and kind of keeping the machine fed every week. Is the newsletter a more, I don’t know, sustainable, less up and down journey? Or are there just other downsides that make it net-net just as bad or just as good?

Kyle Poyar: Well, with the newsletter — I think that anyone that is trying to do any sort of creation online, whether it’s LinkedIn, Instagram, TikTok, whatever it is, the algorithms are fantastic for getting some initial reach, but they’re increasingly feast or famine. There’s no guarantee that anyone following you will see your content. Linking someone outside of the platform is really challenging. So you’re stuck within this sort of walled garden. It’s just a really challenging place to have any sort of control over your growth or what people are seeing. And so I encourage people, yeah, sure, use the algorithms, build a following there, but quickly pivot people from the closed social media platforms onto something that you control.

And what I find for the newsletter, with my control audience, views and engagement are extremely consistent. I mean, yeah, do I have some open rates or some subject lines that do better with open rates than others? Yeah, of course. But my open rates range from like 42% to 46%. It’s a pretty tight window. My deliverability is consistent. As much as people talk about inboxes being spammed, I have pretty good confidence that my newsletters are getting delivered to someone’s email, and that a lot of people are opening them. And then my views are pretty consistent from newsletter to newsletter. I mean, we’re looking at within a range of plus or minus like 15 to 20%, right? So you’ve got some good ones, you’ve got some bad ones, but it’s very consistent.

And I get a lot of replies. So one thing that’s great with a newsletter is someone can just reply and end up in your inbox. And so I also just feel a much stronger direct connection, and it’s almost always a positive connection. If someone doesn’t like a post, they’ll just unsubscribe to the newsletter. They’re not going to send me hate mail about it. If they do really like a post, they’ll reply. It’s often a great source of leads for some of the consulting and advisory work I do too. I would encourage just about anyone — a newsletter is one of the best things that you can build. The challenge though is the growth is a little bit more linear. It’s slow and steady growth. You don’t have these algorithmic highs and lows. So you have to be willing to build over the long term. And you need content that stands out, that I think needs to be so good people are willing to pay for it. Otherwise you don’t earn the right to end up in someone’s inbox week after week. And not everyone is willing to invest that much in content.

Finn Thormeier: How do you feel about saturation for people who don’t yet have a newsletter? Because obviously, similar to LinkedIn, which is getting more and more crowded, when you and Emily Kramer started on Substack five years ago, there were a lot fewer newsletters and people on Substack. How do you feel about the opportunity now for someone new starting?

Kyle Poyar: It’s funny. When I started my newsletter, I thought I was late to the game. I thought Substack was already saturated. Lenny had been on Substack for a couple of years at that point. There were already a number of newsletters that had really taken off. I felt like it was cliche in 2021 for someone who worked in VC to have their own Substack. The thing is, it’s just hard to predict with a lot of these channels. Even if something seems saturated, there’s often still room for one more. And just because something in aggregate might be saturated doesn’t mean people aren’t going to care about your content specifically. I think that there’s always space for one more.

And my advice for people though, is niche down. So yes, marketing as a concept might be a pretty saturated space, but do you work in demand gen or product marketing or content marketing or a different part of marketing? Are you an expert in like AI tooling or XYZ channel that most people haven’t really optimized for? What’s that really specific expertise? And if you can find something that maybe a thousand people care about, but those thousand people care about a lot, that gives you permission to expand from that position of strength. In my early days of writing, a lot of my writing was around pricing and product-led growth. I actually don’t have that much on product-led growth anymore. And pricing is maybe one out of five, one out of six newsletters. I’m much broader. I’ve broadened my topics. I’ve added a lot of new content pillars. But I started with a niche — I even had posts that were about pricing for product-led growth companies that were specifically B2B software, like series A through C. I don’t think that there were more than 100 companies that would really care about that content. But if you can write the best content for a hyper-specific niche, that earns you the right to grow with your audience.

Finn Thormeier: And then for people who want to do that and run it as a business, so monetize the newsletter — what’s your recommendation? There’s different levers, obviously. I think you have premium subscribers, which is $15 a month. I think you have some affiliates with companies that you recommend. You obviously have an advising practice. I think you have sponsorships and partnerships. Across these things, what advice do you have for people who want to start writing but then have a path towards actually making that a real income?

Kyle Poyar: Yeah. I mean, I pay a lot of attention to monetization. It’s where I started my career. I spent my first six years doing pricing strategy consulting work. And so monetization is near and dear to my heart. Substack will tell you that is the number one way they make money. They take a cut on every transaction from a subscriber. That is their business model. I don’t think that’s the business model for most B2B newsletters. I personally am probably going to make six to seven times as much revenue from ads as I do from paid subscribers this year. And I have a six-figure paid subscriber business. It’s just that the ads are that valuable. And that is with publishing once a week.

Finn Thormeier: And when you say ads, is that when I go to your newsletter, basically in the top, you recommend like...

Kyle Poyar: Yeah. And I’m very careful — I don’t recommend products, but in the top, I have an ad slot that’s up to a hundred words. So there’s a specific offer that I have, and yet the text is in my writing. So some of my partners like to just promote the product, other partners like to promote like, hey, we’ve got a webinar coming up, and so the offer is about attending their webinar. Or they’ve released a new content playbook about a topic and that’s the offer. But really it’s like — if you read The Economist and you read it in print, there’s the inside of the magazine cover, right? What’s that first ad that everyone sees as everyone opens to the next page? That’s how I think about the ads in my newsletter. And so that inventory is very valuable to advertisers.

Finn Thormeier: So you always do two slots per newsletter? Because I think there was beehiiv and then Monday.com.

Kyle Poyar: I do one slot, the monday.com feature. And this is, I think, something I should probably clarify for my readers. I love featuring case studies of interesting things people are doing, and that does help promote their company, but I don’t charge for that. I mean, I think the way I charge is through a lot of their time — these are very time intensive pieces. And I ask for very potentially sensitive information that a lot of brands are not willing to share publicly, but I want them to be able to share some of these next level insights with my readers. And so for people that work on collaborations with me, it’s free to collaborate — bylines, guest posts, some of these case studies. But I monetize that ad slot at the beginning.

Finn Thormeier: And so you said you have a six-figure business just from premium subscribers, which is the 15 bucks per month, and then you’re going to do six to seven times more than that from the ads.

Kyle Poyar: Exactly.

Finn Thormeier: Which, I mean, that means you do minimum 600k a year just from ads. And is it fair for me to say to just divide that by 52, if you’re going to do a weekly newsletter, to get a rough estimate of an ad spot cost?

Kyle Poyar: Yeah. People can do the math. It works out to be a little over 10 grand per slot. It’s not totally apples to apples to think of the cost per slot, because when I think about ad packages, I have multiple editions. I have minimum duration. So my minimum buy for most partners is quarterly, but I have a number of partners that actually have annual ad buys. And so there are in some ways volume discounts, but also some of these partnerships also include like I’ll speak at one of their customer events, or we’ll do a couple of webinars together, and then maybe do some LinkedIn posts around that partnership as well. And so these are partnerships that are anchored in the newsletter, but there are different packages to monetize things beyond just the ad slot.

And for my partners, that’s valuable because it’s really about maximizing that exposure over a long period of time. Because if you’re trying to promote an enterprise-grade billing software that might be six figures or maybe even a seven-figure purchase for customers, someone’s not going to see one ad slot and buy your product. That’s just not how it works. You want to stay relevant — you want them to know who your brand is and stay relevant for them, so that when that customer has the purchase need, they already trust your brand and that brand is front and center in their consideration set. And that’s where I find quarterly actually gives more time for attribution, for marketers to actually see that these ads are generating a return for them. And it also gives more time for some of the early pipeline to either close or not close, so they can ideally attribute deals. Because at the end of the day, for ad revenue, the ad business models have been about cost per impression or cost per thousand impressions. I think that is total BS in B2B, because it’s really about influence on purchasing within really target customers.

Finn Thormeier: Right. And who is your audience, right? I mean, you have a very specific audience and probably quite a few senior leaders in there. So that’s very different.

Kyle Poyar: Exactly. I think about the ceiling on how much you can charge for ads is based on what ROI you generate for your advertisers.

Finn Thormeier: Right. What part of the business is the advising, consulting? Is it a meaningful part of how you monetize having this audience, or is it something you do on the side that’s nice but not super meaningful?

Kyle Poyar: So the advising, consulting is about a third of my overall revenue. So still fairly healthy. And for that, I devote probably about half of my time to advising and consulting work. And the way I think about that — so it is healthy from a monetization perspective, I do a good business there, but realistically, it helps me stay fresh to what’s top of mind for high growth companies. And it holds me accountable to real life problems and trying to be helpful to an individual person and company on something that is hard for them to solve. And by doing that, I think that it gives me a lot better insight into what topics I should write about and how to write in a way that’s really going to speak to what people care about. And so, yes, I do monetize on the advising, consulting side, but honestly, a lot of it is picking the right companies to work with and problems to solve with them. And if I can do that, it really makes this whole thing a stronger flywheel.

Finn Thormeier: How do you think about — I’m just curious. So I have a Substack. I have 3,000 subscribers. It’s basically just my podcast. I have a podcast where I interview mostly around executive brand and LinkedIn and audience growth. It’s not monetized at all. The only way that I kind of monetize it is that I run an agency that does executive brand, but it’s very indirect. Because I oftentimes talk about things that are not at all LinkedIn or executive brand related. How should I think about — is this worth trying to turn it into its own thing that I monetize, by trying to grow it more aggressively, by trying to charge premium subscribers, which I don’t do, but trying to find advertisers, which I don’t do, but trying to monetize it in different ways? Or should I just keep it as the podcast, the Substack, that every now and then sends a person to my agency? How would you consult me through this?

Kyle Poyar: Well, so yeah, 3,000 is on the smaller side for monetization, but it’s not too small for monetization by any means, especially if it’s a very hyper-targeted audience that is at an executive level. And so if you could run your subscribers through an enrichment, or if you have a reader survey where you get a sense of who these people are — if these are executives at interesting companies, I think there could be some monetization opportunity.

A few thoughts I have for you. One is, podcasts are worth a lot more in terms of cost per impression than a newsletter ad. And I think part of that’s like, it’s a host read in your voice. Maybe people can double dip where they get promoted in your newsletter and your podcast. I think it’s also a longer ad slot usually, and so it can convey a lot more nuance and information about the company. So having ads that run in your newsletter and your podcast — I think that you could do that. And I think you could start charging — I don’t know exactly how much for them, but I think you can start charging a handful of partners.

And my personal view is that your readers and your listeners will not be fazed by it. I went five years before having a single ad in my newsletter. I was really nervous about what happened when I ran my first ad. There was zero change in terms of click-through, open rates, anything. When I partner with great brands, I actually get good feedback from a lot of my readers, because they all work in tech. They’re working in go-to-market. They’re getting exposed to tools and offers that they had not heard of before, that are going to help them do better at their job. And so for a lot of readers, if you partner with great companies and the offers are valuable, they see it as a win-win. And so in your space, if there are products that you’re regularly partnering with on your consulting work with companies and finding yourself recommending frequently — these are products you already trust, you think your readers and listeners are going to get value using — I don’t think people would be that turned off by the ad slot.

And by having the ad slot, that’s actually going to give you money that you can invest in acquisition. It’s going to give you more reason to keep doing it. You’re going to be on the hook to keep publishing. When you get busy with the consulting work, you’re not going to fall off an episode — you’re going to have a reason to do the episode. And so I would start there. I don’t think that the paid subscriber model makes as much sense for a podcast newsletter combo, but there are some things if you wanted to go paid from a subscriber standpoint. There are things that you could do, like publish somewhat regular in-depth reports, or take some of the consulting work.

That kind of has a monetization ladder to more effectively monetize different folks. And honestly, that’s how I think of paid subscribers for my newsletter. I’m not actually gating almost any newsletter post. They see the full edition. What I do is I produce these in-depth reports that are like 60 page PDF reports. And I do that once or twice a quarter, on topics that I think are really valuable to readers. And every report has a summary in the newsletter. That summary is fine for 95% of people. Maybe 5% want to read the full 60-page report. That’s worth a lot, I think. And that has a lot of my kind of proprietary expertise, that are the things that I work on on a consulting basis too. And so I charge for that. And I don’t think it hurts the free reader experience that I charge for it.

Finn Thormeier: beehiiv versus Substack. You switched to beehiiv a couple months ago after using Substack for many years. Obviously, I think you’re now a beehiiv partner, so that’s important to disclose here, I guess. But I’m curious about how you would compare them, what you like more of which, which one you think in the end is the better platform for whom?

Kyle Poyar: Yeah. So I went about five years on Substack. And then it was when I started getting serious with things like wanting to have advertising, wanting to have paid subscriptions — that’s when I started realizing all the limitations in the platform. So if you have a free newsletter, Substack has great free tools. They don’t charge a subscription fee. It’s really intuitive. There’s some built-in growth through recommendations and Notes. It’s a really simple platform to start using. But if your ambitions are much more advanced with your newsletter, I think you’re going to find a lot of limitations.

Things that I ran into with Substack that people should be aware of before getting locked into the ecosystem were: for a while, your website had very little customization abilities. I think that’s changed a little bit. It’s hard to produce ad slots that feel kind of carved out from the content, because there’s not a whole lot of customization in the editor. It’s kind of meant to look more like Substack. The emails get delivered via Substack deliverability, and so their deliverability health impacts yours. On beehiiv, you can send from your own domain.

Finn Thormeier: Have you seen a big change in your deliverability?

Kyle Poyar: So yeah, my deliverability rates were trending down to low, like 91, 92% on Substack. And when I moved to beehiiv, they’ve been at 98, 99% pretty consistently. Open rates have gone from low to mid-30s to mid-40s. So my emails are getting delivered and read at much higher rates.

Finn Thormeier: What’s the theory on the — I mean, that’s a much higher open rate, right? What’s the theory on why is that?

Kyle Poyar: So I think some of it is just the deliverability tools that beehiiv has, and also being able to deliver from your own domain. I think that actually lands in people’s inbox at a higher rate. I did a one-time cleaning of a few thousand people that had not gotten any emails in months via Substack. But that cleaning is not nearly enough to account for how big of a jump I did have and how consistent it’s been. Other things I did — I did a staged rollout. So I actually did a couple of sends to a smaller, more engaged audience before ramping up the sends to the full list. And I think that staging did really help warm up the domain and get the emails landing in the primary inbox. I’m not a deliverability expert though. That’s the kind of thing that I’m really happy for a platform to manage. I just want the emails to be in people’s inbox.

Finn Thormeier: Sure.

Kyle Poyar: But other things — analytics are totally different. So you can actually see things like unsubscribes. You can see much better analytics on the website and on the subscriber behavior via beehiiv. You also see a lot better click based analytics, where they have a distinction between all clicks and verified clicks, which is really important for advertisers, because you get a lot of clicks that are just spam platforms, even like checking your links. And so on Substack, I think it consistently misreports click behavior versus what the advertiser would see as valuable clicks. Just my opinion — I mean, I’m not an expert at all of these things. But then they have an API and an MCP, so you can access everything through Claude, which is my preferred AI tool. I connect my beehiiv with Zapier and also have a lot of automations I run within beehiiv. They also have things like digital products, and they don’t take a cut on your ad revenue.

I could go on about this stuff because I’m a nerd about it. These things are not things that you probably care about if you don’t have big aspirations to build a business, or you’re not building a really serious newsletter. And so if you just want something basic out of the box, I do think Substack is okay. But these things — I mention them both because I’m a nerd, and because I think that people that do have those ambitions, they should know about these before they maybe get locked into a platform too early.

Finn Thormeier: Do you think — Substack has this home feed with Notes and stuff. Do you think the fact that beehiiv doesn’t have that, is that a benefit or a downside?

Kyle Poyar: Oh, this is a tough question. So to me, I’ll be honest, I was a beneficiary of some of that social media feed. You do get some growth on it through Substack, through Notes, and through just your posts popping up algorithmically via the app. But what I found is that Substack kept pushing following as opposed to subscribing. And following was great for their ecosystem, not so great for you as a publisher. It had a lot of junk and noise on it and just was not super valuable. It was a lot of people posting about like, if you put your newsletter in the comments, I’ll go subscribe to it. And then those would go viral. And you’re like, I don’t need another social media platform.

The other thing that stood out to me was that I kept noticing that Substack was promoting the app. And so my readers would sometimes get automated notifications to download the Substack app. And I also would notice — I think they’ve stopped this — but they would have some tests where if your posts were going to be cut off by the email provider because they were too long, Substack was going to push you to go read the rest of it in their app. A lot of Substack’s growth is built on this idea of, the audience is Substack’s and they’re kind of locked into the Substack app and algorithm ecosystem. And that is great right now for writers, because you’re going to benefit from those readers that are locked into the ecosystem. I got worried about this being another algorithm that had control over my audience and my data that would hurt me long term. And so I did not want to be locked into another one. And that audience control was really important to me. But, you know, you do sacrifice some growth in the short term for that.

Finn Thormeier: Because of the recommendations and the notes.

Kyle Poyar: Yep, exactly.

Finn Thormeier: Yeah. I mean, one of the big reasons why I decided to go with Substack — I was overthinking it way too long — is because beehiiv at the time didn’t have the podcast hosting thing. Which seems to be a solved problem now.

Kyle Poyar: Yeah. So man, maybe you’re going to give it another look?

Finn Thormeier: How painful is the migration?

Kyle Poyar: I am a beehiiv partner. They’re great. I actually have known Tyler, their CEO, for like three years. He’d been trying to convince me to move to beehiiv for a while. And I didn’t move because of the partnership. I have plenty of other ad partners. You’re not going to switch your entire platform just because there’s an advertiser who wants to advertise. But it is very helpful that I have that direct relationship with them. I was given a white glove treatment, and I don’t know if everyone gets that treatment. I hope that they do, but it’s been amazing for me.

Finn Thormeier: I guess with 3K subscribers, I got to do some work. Cool. No, this makes sense. All right, we’re at time. Kyle, thank you so much for all of your insights. Obviously, if people want to check you out, either your LinkedIn or your newsletter, both will be linked up in the show notes. And that’s it. Thank you for your time.

Kyle Poyar: Thanks for having me on.

Adam Holmgren is the co-founder & CEO of Fibbler, a paid ads attribution tool that connects your Linkedin and Google ad accounts to your CRM and calculates influenced pipeline and revenue. They are bootstrapped, roughly 2.5 years in, and they just hit $1M ARR with a team of two. Before Fibbler, Adam was Head of Demand Gen at Rillion and GetAccept.

In this episode, we talk about how Adam batch writes five posts every Sunday night, his three content pillars, the $10-15k/month Linkedin ads engine behind Fibbler’s growth, the 100-like threshold for turning posts into ads, cold vs retargeting frequency, and the pink lion mascot that became one of their best marketing assets.

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We discuss:

* How Adam writes five Linkedin posts every Sunday night

* The three content pillars behind Fibbler’s growth

* Why almost every Adam post is an image post now (and why pure text posts stopped working for him)

* His 100-like threshold to decide which organic posts get promoted into Thought Leader ads

* Fibbler’s two-layer ad structure

* The $100,000 ad-spend post that’s been running as an ad for over a year

* Why the founder of an attribution tool ignores attribution for his own advertising

* The pink lion mascot

* Running B2B ads on Hulu & HBO Max through Linkedin CTV

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Connect with Adam:

Adam’s LinkedIn: https://www.linkedin.com/in/adam-holmgren/

Fibbler: https://fibbler.co/

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Connect with Finn:

LinkedIn: https://www.linkedin.com/in/finnthormeier/

Project 33 - LinkedIn Agency for CEOs: https://www.project33.io/ (do we want to switch this alredy to: Thormeier.co: https://thormeier.co/)

Hope you enjoy!!