The Many Voices of Justin Jackson

TGM is a podcast about meaning, disguised as a podcast about entrepreneurship. It’s a bright-eyed and sweary look at what it takes to do work that matters.

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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

Rob Walling on Finding Your Purpose and How to Actually Enjoy Your Life

I'm still alive. Hope you are too. Here's a little update.

The One About No Episode

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

Matt Giovcanisci on Getting Comfortable with Who You Are, and Making Your Own Rules

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

Justin Jackson on Therapy for Entrepreneurs, Ego, and Coming Back from the Bottom

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).

The Gently Mad Trailer

The Gently Mad

The Many Voices of Justin Jackson

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