Rob Walling is a man of many talents. Over the course of his career he has been an programmer, a freelancer, a bootstrapper,  a business owner, an author, a speaker, a podcaster. The list goes on...

A few years back he founded  Drip (and email marketing company), which he later sold to LeadPages. It's a path that many of us aspire to.

But what I loved about Rob's story was his realization that there are different kinds of freedom, and what we think will make us happy in the beginning, almost never does, and changes dramatically with the passage of time.

We talked about the struggle of finding meaning and purpose in our lives and how that relates to our work, as well as Rob's own realizations about what really matters and why it takes so long to figure that out.

I thought we were going to talk a lot about entrepreneurship and building meaningful business. And while, we did talk about that, our conversation ended up being a littler more philosophical (which are my favorite kinds of conversations).

I hope you enjoy this episode as much as I did. There's a lot to glean here.

Happy listening!

Rob Walling: @robwallingThe Gently Mad: @tgmpodcastAdam Clark: @avclark

Matt Giovanisci is one those guys that I can talk to for hours. We have a ton in common, but just enough differences that it stays interesting.

A lot has changed since his first appearance on the show, which you can listen to back in episode ??. I feel like we've both changed in some very similar ways since then. Where last time there seemed to be a lot of doubt and questioning, now there's assurance and confidence.

And I think some of that only comes with certain amount of life experience.

We talked about all the different projects we've both been involved in and, what the ultimate point of it all is, and how all these different interests and projects are connected.

If you think of yourself as a generalist, or as the kind of person who really enjoys doing a lot of different things, this episode is for you. I'm definitely that kind of person and sometimes it can feel like I'm trying to do a million different things, and doing none of them well.

We got into that exact issue and wether or not it's even possible to do a lot of different things well. I think Matt is a clear example that it is possible. But it takes time and hard work.

He also just launched a new show, which was kind of the impetus for this conversation.

Enjoy!

Show Notes

28:28 - Chewbacca Bob

31:14 - The Hugh Hefner of pool care

47:04 - Why you shouldn't do what everyone else is doing

71:40 - What to do you when you fail

98:36 - What connects it all

122:37 - There's no such thing as a bad idea

More about Matt

Twitter

Moneylab.co

Matt's new podcast

Justin Jackson is no stranger to this show. Technically this is only his second appearance (check out his first episode nearly four years ago), but there are hours of recorded conversations floating around my hard drive.

I always enjoy talking to Justin. Despite how much we have in common, he always helps me see things from a fresh and different angle. And his episode was no exception.

Every time we talk, it's like catching up with an old friend. And even though we only just met in person for the first time at MicroConf in Las Vegas, he is indeed someone I would consider an old friend.

Justin's career has spanned the gamut of the product, start up and SaaS worlds. He's an author, podcaster, educator and most recently a SaaS founder.

There's no bonus episode this week because I decided to release the entire conversation. At just over 120 minutes, it's a long one, but worth listening to.

Our conversation ranged from parenting, to business building, to the things that hold us back as entrepreneurs, to why every entrepreneur should have a therapist, and literally everything you could imagine in-between.

These are my favorite kinds of episodes, because there's so much to glean from a guy like Justin about life in general.

I hope you love it as much as I do.

Enjoy!

Note: Yesterday I released a two-minute teaser of some of the most fun bits from the show. Here it is as well:

Show Notes

Min 25:05 - The power of podcasting

Min 38:45 - Why it’s important to evaluate what we’re putting out into the world

Min 53 - A surprising realizing about people

Min 67:22 - The time to get support is before you really need it

Min 71:12 - How Justin came back from bottoming out

Min 79:09 - Everything is a balancing act between chaos and order

Min 87:47 - How to move forward when everything falls apart

Min 92:45 - Why you're not winning

Min 101:08 - Ego is the enemy

Min 102:37 - The disaster of always running from discomfort

Min 125:52 - Maslow's hierarchy of needs for businesses

Min 128:47 - What if you had to completely start over?

Bits & Bytes Mentioned in the Show

Justin's first appearance on TGM

MicroConf

Startups For the Rest of Us

Billy Corgan on The Joe Rogan Experience

Billy Corgan Disney meme

Will Smith on Fault vs Responsibility

Cortland Allen

Indie Hackers

Corbett Barr

The Fizzle Show

Dan Harmon

Paul Jarvis

The Gently Mad is a podcast about meaning, disguised as a podcast about entrepreneurship. It’s a bright-eyed and sweary look at what it takes to make a living on the internet (and still sleep at night).

Paul Jarvis is back! This is third or fourth time I think. We always have a lot of fun and this conversation was no different. Paul is a long-time web designer turned author and product maker. He has handful of great courses you should check out.

We talked a lot about the difference between an idea and an actual business, what makes our businesses sustainable for the long haul, and the discipline it takes to do something well.

Like last week, the bonus episode was as long as the main episode and we covered the specifics of how Paul uses podcasting to grow and engage his audience. As well the specific strategies he's using to make a full-time living from his courses.

Enjoy!

If you want access to this bonus episode and all future bonus episodes, subscribe below. If you’re on your phone, you can subscribe be texting the word “TGM” to 345345.

In this week's episode of TGM, Brian and I talk about "idea fatigue", what to do when when your idea is the same as some else's, as well as why Brian believes that a productized service is *still* the fastest way to start generating revenue.

Brian has been around the block with more than a few businesses. His newest, AudienceOps, helps businesses with done-for-you written content. But he's also expanding into done-for-you podcasting.

In fact, I had a bit of a mini freakout when he first announced the new service, because it was so close to Podcast Royale (which hadn't been launched yet). We talked about that and what to do when your idea is very similar to something that already exists.

I really enjoyed the part of the episode where Brian talked about how he come up with the idea for AudienceOps and launched quickly. A lot of great inspiration in there.

Don't forget to subscribe for access to the bonus episode. We did a deep dive into productized services, podcasting, what Brian would do differently if he had to start all over, and so much more.

Bonus Episode Show Notes

0:42 - How podcasting transformed his business

4:00 - How to compete in a saturated market

7:20 - How do you manage so many different projects?

10:40 - Should you try to combine your various projects (personal writing, products, businesses, services, etc.)?

16:30 - Why Brian rebranded and reorganized all his projects

19:00 - How to increase sales of info products

29:00 - How to keep your audience engaged

34:35 - The problem with the whole “charge more” advice

41:15 - What Brian would do if starting over today

Enjoy!

If you want access to this bonus episode and all future bonus episodes, subscribe below. If you're on your phone, you can subscribe be texting the word "TGM" to 345345.

Janelle Allen is the founder of ZenCourses.co and is an expert in Instructional Design and online learning. We talked a lot about entrepreneurship and why it's so important to not only know your why, but to own it.

Don't forget to subscribe for access to the bonus episode. We did a deep dive into online course creation, what's working, what's not, mistakes to avoid, and, of course, how to create profitable online courses in 2018.

What we covered in the bonus episode

1:30 - Can someone still create a profitable online course in 2018?

5:50 - Why passive income is bullshit

8:55 - How do you resolve the disconnect between creating something once vs guided programs and ongoing

10:30 - How do you create a course that gets result?

13:10 - What do you do when your course has multiple outcomes and/or goals?

16:00 - What kind of courses work the best?

18:25 - What’s the difference between course goals and outcomes and why does it matter?

21:35 - What video link is best?

23:40 - Is it easier to sell a smaller ultra specific course or a bigger “cover-everything” kind of course?

26:30 - Why segmenting your audience is important

28 - How to know if you should change your course topic?

Enjoy!

If you want access to this bonus episode and all future bonus episodes, subscribe below. If you're on your phone, you can subscribe be texting the word "TGM" to 345345.

I’ve been a fan of Derek Webb for as long as I can remember. But’s it’s only been in the last couple years that I’ve gotten to know him a little bit more personally. He was a guest on this show a few years ago and that time we talked a lot about the music industry in general and how it’s changing (for the better) for those who want to make a living as an independent artist. A lot of sh*t has gone down since then. Both for me and for Derek. And one of the reason’s I love him and his music so much is that our stages of life seem to have a weird sort of symbiotic relationship. Usually whenever I’m going through something, Derek releases a new record and it’s exactly what I needed at that time. That’s certainly true for his latest record, Fingers Crossed. It’s an album about the loss and grief that comes with change and the hope we have to find within ourselves if we’re to grow rather than wither within the sadness of life’s turbulence. To use Derek’s own words, “It’s a sad as sh*t record”. But it’s a kind of *necessary* sadness. The kind of sadness that comes from serious soul work. And, honestly, that’s the best way I have of describing this conversation. It was sad at times, but also poignant and surprisingly buoyant with hope. Hope for what’s next, despite the pain of leaving behind the past. I hope you’ll check out Derek’s album. And I hope you get something out of this conversation. I certainly had a great time doing it. Enjoy the show.