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June 18, 2026 - Podcast

Million Dollar Founder Explains How To Avoid Burnout In 2026 | 133

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Why did this founder fire himself from his own company? That’s what I wanted to find out when I sat down with Steve Kamb, founder of Nerd Fitness. We’ve known each other for a long time, and I’ve watched him build an incredible audience and business. But then, to my surprise, he “fired” himself – twice! Steve shares the surprising truth about chasing growth, the pitfalls of wearing the wrong hat in your own business, and how he rediscovered his passion for writing. His journey is a powerful reminder that sometimes, the true path to fulfillment means stepping away from the very thing you’ve so diligently built.

Timestamps:

00:00 Introduction
01:10 Firing myself (twice!) from Nerd Fitness
05:37 The five years I spent in the wrong seat
07:20 The “If you’re not growing, you’re shrinking” myth
10:37 How I realized writing is what lights me up
12:55 When to double down on strengths vs. fix weaknesses
18:19 The curated “all I do is win” internet vs. real life
20:20 Sharing my failures: cancer, Google changing, divorce
23:09 The overwhelming positive response to vulnerability
24:06 How my book was born and evolved
30:17 My visit to the Museum of Failure
33:55 My PACT framework: Pause, Accept, Change, Try
40:22 Everything old is new again in content
49:00 The value of Craft + Commerce and community
56:14 Longevity in creative work: falling in love with the craft
1:02:43 How to Try Again: Where to find the book

Learn more about the podcast:

https://nathanbarry.com/show

Follow Nathan:

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Kit

Follow Steve:

How To Try Again (Book)
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Nerd Fitness

Featured in this episode:

Kit
How to Try Again
Nerd Fitness
The Museum of Failure

Highlights:

01:10 – Sometimes you have to make the hard choice to step aside from a role you’ve created to allow your business to grow into its next phase, even if that person is you.
07:20 – Steve shares his take on the “If you’re not growing, you’re shrinking” myth.
20:20 – The internet is full of “all I do is win” stories. Steve shares his real-life struggles including his cancer diagnosis, Google algorithm changes, and going through a divorce.
33:55 – Steve shares his PACT framework: Pause, Accept, Change, Try.
56:14 – How to find longevity in creative work: falling in love with the craft.

Transcript:

[00:00:00] Steve: Overnight, the business exploded. All of a sudden, I found myself in charge of a team of 40 to 45 people. And then you fired yourself. Yeah.

[00:00:08] Nathan: Steve Kamb built Nerd Fitness into a 40-person company, and spent five years chasing the wrong goal with the wrong metrics.

[00:00:14] Steve: You can keep playing this position over here that you’re not actually good at, or you can accept reality.

[00:00:20] And there’s actually something powerful, too, about saying like, “”. Oh, I love that.

[00:00:25] Nathan: He fired himself twice, both times on purpose, and what he found on the other side was a return to writing, a better business, and a book called How to Try Again.

[00:00:33] Steve: You wake up every day, “I’m already behind. I have more to do.”

[00:00:37] Instead of trying to get better at juggling chainsaws, maybe it’s okay that you stop juggling chainsaws. Yeah.

[00:00:42] Nathan: If you’ve ever built something successful and wondered why it still doesn’t feel right, this one’s for you.

[00:00:47] Steve: There’s a dream that people want to sell you. When you sign on to Instagram, you see the best version of everybody else, and the story that you’re seeing is not real.

[00:00:54] Nathan: In this episode, Steve walks through a framework for recognizing when you’re optimizing for the wrong thing, and how to make the move once you know.

[00:01:01] Steve: This is not, like, a top secret protocol, but it’s something you will remember. That

[00:01:05] Nathan: is

[00:01:05] Steve: so powerful

[00:01:10] Nathan: Steve, I’ve known you for a very long time, and I’ve watched you build Nerd Fitness to hundreds of thousands of subscribers, millions in revenue, and then you

[00:01:19] Steve: fired yourself. Yeah. What?

[00:01:22] Nathan: Uh- What happened there?

[00:01:24] Steve: Yeah. Uh, so it’s been 17 years-

[00:01:27] Nathan: Yeah …

[00:01:28] Steve: since I made Nerd Fitness my, my thing. I actually demoted myself once- Okay

[00:01:33] and then I fired myself. Oh, okay. So it was two steps.

[00:01:36] Nathan: Yeah. Performance improvement plan. And then didn’t, didn’t meet it, and you

[00:01:39] Steve: were out. Yeah, I had to talk to myself. It got super awkward.

[00:01:42] Nathan: Full HR.

[00:01:43] Steve: It was a whole thing.

[00:01:44] Nathan: Yeah.

[00:01:44] Steve: It was a whole thing. Um, no, essentially what happened was I started Nerd Fitness as a side hobby.

[00:01:50] Mm-hmm. I love… Well, I didn’t realize it at the time, but I love writing.

[00:01:55] Nathan: Right.

[00:01:55] Steve: I didn’t know what to do, but I stumbled across this guy. I had this idea for helping nerds get fit. I Googled nerd and fitness. Nothing popped up.

[00:02:05] Nathan: Yeah.

[00:02:06] Steve: So I bought nerdfitness.com, and- Great

[00:02:08] Nathan: domain …

[00:02:09] Steve: had no idea how I was gonna make money with it or anything, but I stumbled across a guy named Chris Guillebeau-

[00:02:13] Nathan: Yep

[00:02:13] Steve: who was making money on the internet as a writer. Okay, cool. I’ll start writing. And just kinda put my head down. I wrote two articles a week every week. Is that because Chris wrote two articles a week? Every Monday and Thursday, 100%. So shout out to Chris G. Yep. Um, and I wrote those essays and accidentally, you know, built, built a following, and then started to build a business and hired employees and things kept growing, and then I needed to hire more people, and then things grew.

[00:02:45] And then, uh, I kept going, and then during the pandemic, everything shut down.

[00:02:52] Nathan: Mm-hmm.

[00:02:53] Steve: People couldn’t go to gyms, and Nerd Fitness happened to be the number one search term for online coaching on Google. Oh, wow. So overnight, the business, like, exploded because nobody could go to a gym, and they wanted- Right

[00:03:06] a trainer. So all of a sudden, I found myself in charge of 40, 45, a team of 40 to 45 people. Um, and I wasn’t writing anymore. I was… I started to avoid work-

[00:03:20] Nathan: Mm-hmm …

[00:03:21] Steve: because I realized I was sitting in the wrong seat in my own company. And, like, I kinda sucked the fun out of why I started doing it in the first place- Mm-hmm

[00:03:31] which was to write fun essays about helping people So I said, “Okay, there’s somebody who’s second in line, and hey, I want you to take over and run this business. I’m gonna demote myself to chief marketing officer. That sounds like a semi-important title- Right … and people will like it, and that seems reasonable for my business.”

[00:03:54] And I think I made it about a month as the chief marketing officer of Nerd Fitness and realized like I’m terrible at this too. I’m still managing people. I’m still spending all of my time dealing with meetings, and, um, spreadsheets, and optimization, and A/B split testing, and, uh, rewriting essays for search engine optimization, all of this stuff.

[00:04:14] And I realized that I was, again, sitting in the wrong seat in my own business. I wasn’t doing any of the stuff that I liked. So I made the essentially extreme decision to fire myself from Nerd Fitness. I said, “You’re now in charge. I’m available on Mondays, but for my mental health and my life, I have to go do the thing that I’m actually really good at, which is writing.”

[00:04:40] And that led me down the path to, you know, hopefully write another book.

[00:04:45] Nathan: Yeah. Wow. So I mean, a lot happened in that, and I feel like there’s all these founders who are very attached to founder and CEO, and like those go hand-in-hand. Sure. But they don’t have to. And so there’s a lot of these people that I really respect, like Dharmesh Shah, who’s the founder and CTO of HubSpot, and I’ve known him for, I don’t know, 12, 13 years, and he has no direct reports at HubSpot, right?

[00:05:10] He’s the largest shareholder, uh, ’cause he invested money when it started, all the stuff, right? The largest individual shareholder of HubSpot. No direct reports, does not have any sh- you know, he messes around with code, the future of the company, AI, agents, and all that, right? He fired himself from basically the whole executive team.

[00:05:27] He’s like, “I live over here.” And it- he’s like, “Look, I’m, I’m way happier doing that.” And so I love that you did the same thing, and it worked out. Y-

[00:05:37] Steve: yes, but it took me five years-

[00:05:39] Nathan: Yeah …

[00:05:39] Steve: of sitting in the wrong seat-

[00:05:40] Nathan: Right …

[00:05:41] Steve: before I, I finally accepted it. Mm-hmm. I remember I just moved to New York City and sat down with our mutual friend, Ramit Sethi- Mm-hmm

[00:05:48] and said, “I’m gonna grow, I’m gonna grow this business.” And he essentially said, “All right. Get, get ready to eat shit for about three years- Mm-hmm … and maybe you’ll come out the other side.” So it’s, it’s-

[00:05:59] Nathan: When I feel like at, at that time, everybody was scaling- Oh, yeah … their content businesses. So if we go to these different phases, I wanna go back to the beginning-

[00:06:06] Steve: Sure

[00:06:06] Nathan: when we met, uh, in a little bit, but the stage you’re talking about of living in New York City, it’s like Ramit had a huge team. Derek Halpern was scaling up. You know, so many people were, like, reaching the pinnacle. You know, before it was like, oh, you could make 50 or grand a year or something writing, and that’s incredible.

[00:06:22] It’s like, now people are making millions or tens of millions-

[00:06:25] Steve: Yep …

[00:06:26] Nathan: off of these, uh, basically media companies. And so that’s the world that you surrounded yourself with, right?

[00:06:33] Steve: Yeah, and I think y- we all know this, but our environments shape- Mm-hmm … our decisions and- I think for me, moving to New York, like, as a 29-year-old- Yeah

[00:06:43] everybody has that idea of, “I’m gonna put my dent in the universe.”

[00:06:47] Nathan: Mm-hmm.

[00:06:47] Steve: And I didn’t probably also listen to myself. I also didn’t have the skill set, um, probably like the CEO of HubSpot who says, like, “I want no direct reports,” and also, “I’m… I can build the right team.”

[00:06:59] Nathan: Right.

[00:06:59] Steve: Or the, uh, the… And the right environment.

[00:07:01] There’s certainly luck involved, and I’ll s- I’ll get into, you know, certainly some challenges that we faced as a business- Mm-hmm … between SEO, ChatGPT, Google changing algorithms and adding more blue links, and all of that fun stuff- Right … um, came after the decision for me to step back and then away.

[00:07:19] Nathan: Mm-hmm.

[00:07:20] Steve: But yeah, it’s really alluring to say more, more, more, bigger.

[00:07:24] Nathan: Mm-hmm.

[00:07:24] Steve: Because that’s what people do. And especially in New York City, that’s, that’s kind of what everybody does. Right. How can you not do that? You need to be aspirational.

[00:07:34] Nathan: Where’s your ambition?

[00:07:35] Steve: Where’s your ambition? Right. And, um, you think, like, if you’re not getting bigger, then you’re falling further behind.

[00:07:41] Mm-hmm. If you’re

[00:07:41] Nathan: not growing, you’re shrinking.

[00:07:42] Steve: If you’re not growing, you’re shrinking. Exactly. And, um, you know, there’s actu- like, there’s a topic I talk about in my book, but everybody thinks, like, if you’re not making progress, then you’re falling further behind. Mm-hmm. And, like, the reality is, like, the opposite of progress isn’t stagnation or staying the same.

[00:07:57] The opposite is regress and making things worse. So, like, in that instance, like, a cool small business that is profitable and healthy is, like, an unbelievable place to be, and it doesn’t have to always be bigger, bigger, bigger- Right … because that can introduce some challenges that you might not be ready for, that you’re unable to handle, or society or some aspect of the internet changes, and all of a sudden you catch yourself flat-footed because you have this much bigger ship that you have to turn around.

[00:08:25] Nathan: So I wanna ask about the identity side of it, because I feel like if I were to step back, like, I’ve tied up so much identity in the company that I’ve built, team, like, all of those things, that even if I wanted to fire myself from it, then I’d be like, “Oh, I’d be so tied up in it.” And I talk to people who have sold their companies, and they’re just like, so many of them spend years where they’re, like, list- listless or unhappy in some way because they’re like, “Oh, that was everything.

[00:08:48] I miss having the team, the platform.”

[00:08:50] Steve: Mm-hmm.

[00:08:51] Nathan: You know, that w- like, the founder of that, like, that’s who I was.

[00:08:53] Steve: Yep.

[00:08:54] Nathan: Um, how did you navigate the identity side?

[00:08:57] Steve: Like I said, it took me five years to navigate it. Yeah. Because I, I love people. Mm-hmm. I mean, probably to a fault. Have cer- certainly have people-pleasing tendencies, and I like people to like me.

[00:09:07] But- I like you, Steve. Thanks, man. Really means a lot. Really needed that. I’m gonna tell my therapist about this next week. Yeah, exactly. Um, it took years. Mm-hmm. Because I told myself I had to be in the trenches, and I had to be a great leader, and I had to be involved. Right. So I was burning myself out sitting in the seat in my own company.

[00:09:26] Nathan: Mm-hmm.

[00:09:27] Steve: Not only that, but, um- I think my identity had certainly been tied up in that idea of being bigger and having this team and hiring all these people But the reality was like, man, I’m a writer. I love writing.

[00:09:46] Nathan: Yeah.

[00:09:46] Steve: The most fun I had at Nerd Fitness was when it was me and, like, a few part-time people, and we were just building small things and, and working on it.

[00:09:55] So I had to accept that You can keep playing this position over here that you’re not actually good at, or you can accept reality, which is this is your skill set. This is what you actually love to do. And there’s actually something pretty powerful, too, about saying, like, “I am not the person for this role.

[00:10:16] Somebody else is better at it than me, and as a result, I can double down on my, my actual strengths, which will, in the long run, end up being better for both myself and for Nerd Fitness.”

[00:10:26] Nathan: Mm-hmm.

[00:10:27] Steve: You have to, but you have to be willing to d- h- do the uncomfortable work of asking those questions. It’s probably therapy.

[00:10:34] It’s probably journaling. It’s all of the unfun stuff of sitting with your uncomfortable thoughts and saying, like, how do I… What act- what parts of this actually light me up? Yeah, so how did you get to the point where you realized that writing is what lights you up and that all these other aspects don’t?

[00:10:51] There’s no right answer here- Mm-hmm … for what people are doing. I, I think a lot of it comes out of really, really getting to know yourself. Um, I think about this, uh, everybody’s probably read, there’s this great Neal Stephenson essay, the… He’s a science fiction author. And he has this great essay that says Why I’m a Bad Correspondent.

[00:11:10] And he says, “I am unable to respond to emails and go give talks because, uh, I need four hours of uninterrupted time to write. If I have two blocks of two interrupted hours-” Mm-hmm … “it’s not nearly as good. For me, I need four hours.” So some people might be thinking, like, “Okay, I then need four hours to write to be the best writer.”

[00:11:30] Mm-hmm. Um, I talk about this, uh, in the book too, but there’s, uh, Ian Fleming, who wrote the James Bond novels. Yeah. Every winter, or January, would fly to Jamaica and go to his compound called Goldeneye- Oh, naturally … and he would type on a gold-plated typewriter every morning, and then go swim in the ocean, and then make a cocktail, and then edit his essays, and that’s how he wrote his books.

[00:11:54] Mm-hmm. Meanwhile, you have Agatha Christie, who wrote, I don’t know, something like 60-plus books- … and short stories, sold over a billion copies of her books worldwide. And in her autobiography, she talks about how her friends never knew when she wrote because she would step away- Mm … and write in 30-minute bits, um, 30-minute bursts, and retire to a secret room.

[00:12:15] She didn’t ever have a place to write.

[00:12:17] Nathan: Mm-hmm.

[00:12:17] Steve: You know, she didn’t know where she was gonna be writing that day. All three of those strategies worked.

[00:12:22] Nathan: Mm-hmm.

[00:12:22] Steve: But they worked for the right person. And for me, I think with my stuff, I started writing as a means to an end. I don’t know what this Nerd Fitness thing is.

[00:12:32] I’m gonna start writing and kind of figure it out. Hopefully, I can make a business out of it. But once I started writing and fell in love with the research process and, um, curios- you know, chasing my curiosity, all of a sudden, the writing became the point. And I just fell in love with it. And I came to realize that that is not- how I feel about these other aspects of the business.

[00:12:55] I tried them. They were fun little experiments. Some of them went on a little too long for me. But eventually I realized, like, hey man, this is the thing that you’re really good at that doesn’t, I don’t wanna say doesn’t feel like work, ’cause it’s really challenging to write- Yeah … and to write a book. But it’s so helpful when you can be honest with yourself and say, like, if I do the thing that I’m uniquely gifted at, it makes so many other parts of this a lot easier, and you actually enjoy it.

[00:13:21] And as a result, you know, I’m so enthusiastic. When I’m doing something I love, like, man, I will run through a brick wall to make it happen.

[00:13:28] Nathan: Uh-huh.

[00:13:29] Steve: But if I’m not excited about it, like, oh man, I’ll rearrange my bookshelf. I’ll do

[00:13:34] Nathan: anything- You’ll

[00:13:35] Steve: do anything … I’ll do anything other than those things. And after five years of hitting myself over the head with this reality, I finally accepted it.

[00:13:42] Nathan: So I think conventional wisdom is that, you know, you find what you’re good at, and then also what the company needs. And so whether there’s a gap there, if, if the company needs something, you either hire for it or you level up in those areas. Yep. And that’s something that I’ve seen you do in your life so much, right?

[00:13:57] Where, you know, you’re leveling up all throughout. You have a book about this. Uh, and in this case, you’re taking a different approach. Like, how do you know when it’s time to be like, “Oh, I don’t enjoy this ’cause I’m not doing it the right way, or I don’t have the skill, so let me level up in that area,” w- instead of saying, “Oh, let me just do the opposite,” and say, “I don’t wanna do that.”

[00:14:14] Steve: I think it’s really easy to see what other people are doing-

[00:14:18] Nathan: Mm-hmm … and assume

[00:14:19] Steve: that either you can do it or that it’s something that you must get good at.

[00:14:23] Nathan: Okay.

[00:14:26] Steve: And especially with all of us in small business, we all see the opportunities available to us, and we see the holes in our business or the holes in an industry where we can fill a, we can fill a need or, or serve a new set of customers.

[00:14:39] And it’s really easy to then spread yourself or move into that area and to do the next thing and to force yourself to put your head down and level up at that skill and then hire for it. I’ve tried that across all sorts of skills. In some ways, and sometimes it filled me up and it lit me up. Writing is, again, I keep coming back to this, but it’s the thing that, like, I want to get better at.

[00:15:03] Mm-hmm. And when I get better at that thing, everything else gets easier. And then in other areas, I would try to shore up all of my weaknesses so that I could be a better manager and a better leader, and I put all my time into those things. And essentially, I was really just kind of becoming less… a less crappy manager and a less crappy leader and a less good, you know, like, just slightly elevated- Yeah

[00:15:28] version of that, which wasn’t moving the needle, which wasn’t lighting me up, which kept me from doing the thing that I think I could, again, double down on and get better at, all because it’s so alluring to see the opportunity- Mm-hmm … and not have the, maybe the discipline or not being able to try it and then say, “Mm, this doesn’t feel right.

[00:15:50] It’s not for me,” or, “We’re gonna keep our focus on these things.” Right. I’m really like, “Oh, look at all these shiny objects. I have to do all of them.” Mm-hmm. “And then I’ll just figure it out along the way.” Eventually, you know, that, that kind of catches up to you.

[00:16:02] Nathan: Yeah, so this, this trade-off between doubling down on your strengths and what you truly love and shoring up your weaknesses.

[00:16:07] ‘Cause I think we all have things that we’ve started to do, did not enjoy them, decided we should anyway, and then it turns into something that you love. And it’s a- it’s such a hard thing of like what, what is worth pushing through and getting to the point where you’re like, “Oh, actually, the first two weeks in the gym were not enjoyable, but now that we’re eight weeks in- Yeah

[00:16:25] or that sort of thing, I’m like, I actually kind of miss it if I don’t go.”

[00:16:28] Steve: Yeah.

[00:16:28] Nathan: Versus like, “Oh, no, I shouldn’t be doing this.” Yeah, I, I think you really

[00:16:32] Steve: have to know yourself.

[00:16:33] Nathan: Mm-hmm.

[00:16:33] Steve: Um, I’m a big fan of, you know, creating little, creating experiments and trying- Mm-hmm … thinking, having like a really curious mindset for I wonder if this will work for me.

[00:16:43] Mm-hmm. I wonder if this idea is something that I could get interested in. And it happens to us at Nerd Fitness all the time. It’s people that are like, “I’m trying to lose weight,” or, “I wanna get in shape for something,” and then they start exercising, and a few weeks later they start to look forward to the gym.

[00:17:01] Mm. And they kind of realize, “Oh, like I don’t know how it happened, but I actually look forward to doing my workouts now.” Right. It’s no longer about the end goal. Now it’s like, what am I capable of? And when I take that same principle and apply it back to me and my writing, it’s like, oh, the end goal might have been to build a business, but now it’s, oh, like a perfectly crafted sentence or the weird idea that my brain comes up with.

[00:17:32] Like, there’s some magic happening there that I can’t ignore. If I’m really honest with myself, if I am journaling, having conversations with friends that are really good at their respective things and realizing how much that lights them up, like accepting that for myself and saying like, “Dude, I, I don’t think the sign from the universe is any brighter than it can possibly be right now,” than like this is what you’re meant to be doing.

[00:17:58] Right. And if you double down on it, those weaknesses no longer have to be the thing that you’re focused on. Mm-hmm. This is actually the path forward and how it’s going to make every other part of this engine, your life, better because you’re doing the thing, you’re, you’re exponentially improving at the thing that, that uniquely, that you’re uniquely gifted at.

[00:18:17] Nathan: Yeah. That makes a lot of sense. Something that I think about watching everyone on the internet is r- right, we know we get to see the most polished versions of everyone else’s life and their business and their huge wins and the launch they just did and, and whatever else. It reminds me of probably my favorite, uh, Jimmy Fallon clip, which is Jimmy Fallon and Emma Stone doing a lip sync battle, and they go back and forth, and it’s competitive and all that, and then Emma Stone comes out with All I Do Is Win and just absolutely crushes it.

[00:18:44] It’s the best clip on the internet. But that’s, like watching everyone else’s life, you’re j- it’s, they’re just, all I do is win.

[00:18:50] Steve: Yep.

[00:18:50] Nathan: And you’re like- Well, I ha- I have had wins, but I don’t feel like all I do is win.

[00:18:57] Steve: Sure.

[00:18:57] Nathan: And so it’s really hard to compare in that, in that area. And when you s- in the book, How to Try Again, you dive in and you’re just like, “Here’s all the failures.

[00:19:08] Here’s, here’s when life, like, completely fell apart.”

[00:19:11] Steve: Yeah. It’s so alluring to, for… There’s a dream that people want to sell you. Mm. Right? When you sign on to Instagram or, you know, you open up which- whatever app is on your phone, that whichever social media platform of, of choice you like to-

[00:19:24] Nathan: Yeah …

[00:19:24] Steve: doom scroll through-

[00:19:26] you see the best version of everybody else- Mm … selling you the one thing that will solve all of your problems. And, uh, in the book, I talk about, I call, like, a doom loop, where it’s like, “Oh, I don’t feel good about myself. Oh, but this person is selling me the one thing. Clearly this is it. This will solve it.

[00:19:44] They have it all figured out. I’m a mess. They have it all figured out.” And then they try to do that thing, and they either give up because it wasn’t made for them, or they try it and they don’t get the same results because they’re in a different life situation. Right. They have kids, they have, um, they just went through a restructuring at work, they have an aging parent with dementia, like who…

[00:20:04] They’re doing all these other things and they’re beating themselves up that they can’t follow- Mm … this great protocol. They don’t feel like they’re winning all the time, and they’re beating themselves up. So I wanted to write this book, and started out by saying, like, “Hi, I’m Steve. Here’s all the things I failed at recently.”

[00:20:23] And the only reason I was able to write this book is ’cause of some of those failures. Um, and, like, we’ll get into it, the… You know, a- a- I realized early on, like I said, five years ago at this point, that I wasn’t the guy to be running-

[00:20:36] Nathan: Mm-hmm …

[00:20:36] Steve: my business, but I wanted to write. And I went to go, uh, work with my book agent and get to work on this next book.

[00:20:43] And meanwhile, while that happens, I get the, I get a book deal that I’m super excited about, and immediately felt imposter syndrome first, which was great. Like, “Oh, God, now I have to write a book. Oh, no.” Uh, that’s, that’s interesting how I’m feeling about the thing that I wanted to be doing. Okay, we’ll come back to that.

[00:21:02] And then I found out I had a skin cancer diagnosis on the top- Yeah … of my head that was, uh, they had to, like, scoop it out of my scalp and then kind of suture my head shut so I don’t have a bald spot. Yep. Um, that’s from having a buzz cut as a little kid growing up, uh- And then, um, Nerd Fitness, we ran into some, some headwinds that were- Right

[00:21:22] uh, pretty dramatic. Uh, like everybody knows, Google is not the Google that it used to be.

[00:21:30] Nathan: Right.

[00:21:30] Steve: And we went from, you know, getting a million and a half hits of free Google traffic a month. And all of a sudden, we were still maybe the number one search term for online coaching, but it was underneath 10 blue links-

[00:21:43] Nathan: Right

[00:21:43] Steve: paid.

[00:21:44] Nathan: All the sponsors.

[00:21:44] Steve: Paid, yep. And then ChatGPT, and LLMs, and Google Gemini.

[00:21:50] Nathan: Mm-hmm.

[00:21:50] Steve: And w- we watched as 80% of our traffic-

[00:21:54] Nathan: Mm-hmm …

[00:21:54] Steve: went away. It’s like, oh, okay. Cool. The thing I have been building, um, is no longer… Like, that, that avenue is now changed, and we have to make some dramatic changes at Nerd Fitness.

[00:22:07] Meanwhile, all this is going down. I’m working on writing a book on what to do when life doesn’t go according to plan. And, um, I went through a heartbreaking but amicable divorce. Mm-hmm. Uh, all of this happening, like, at the same time while I’m writing a book about life not going according to plan, and what to do after a failure.

[00:22:27] Nathan: Yeah.

[00:22:29] Steve: It sucked. Mm-hmm. All of this sucked, and it all happened, like, pretty close together. And I had to rethink a lot, and it took a lot of courage to share these things- Oh, yeah … and a l- a lot of stuff ’cause I just… I’m, I’m me, and I’m as honest as I can possibly be, and I wanted people to know, like, “Hey, w- d- we don’t have it all figured out.”

[00:22:53] Nathan: Right. ”

[00:22:53] Steve: And the story that you’re seeing on Instagram is probably not real, and it might not work for you. That doesn’t mean that you’re broken. It means that it doesn’t work for you. Like, we need to find a different path that accepts all of the challenges that you’re facing, that doesn’t beat you up for struggling with what- whatev- whatever you’re struggling with, and honors this life that you’re trying to live in a world that is changing faster than anything.”

[00:23:21] Mm-hmm. And as soon as I was able to share these things with my audience, uh, which took months and months of working up the courage to share a lot of this stuff, um, the response was overwhelming positive. People shared their own stories because they now felt comfortable enough to say, like, “Oh, okay, cool.

[00:23:41] Steve’s not perfect. He’s not… Y- he’s somebody that I can relate to. I no longer feel as bad that I navigated this,” or, “I went- Mm-hmm … struggled with this other thing.” It’s been really helpful, or it’s been really encouraging to hear everybody kinda being like, “Hey, man. Like, cool. We’re all in this club together of kinda weirdos that are trying to navigate life that refuses to d- follow the plan that we want for it.”

[00:24:05] Nathan: Right.

[00:24:06] Steve: So

[00:24:06] Nathan: how did the… Well, like, what book did you sell to a publisher?

[00:24:09] Steve: Sure. And then how did that evolve into How to Try Again? Yeah. So the… Well, okay, the initial premise I sold, uh, I talked to my book agent on January 1st of 2020- three, I think Yeah Maybe 2022. Either way, um, I said, “Hey, I’ve been running Nerd Fitness for 15 years.

[00:24:29] What we do better than anybody else is we help people, like, after they’ve given up on a workout plan- Mm … or they’ve bailed on their New Year’s resolution, we help them, we help them restart.”

[00:24:40] Nathan: Yeah.

[00:24:41] Steve: Actually, the word I used was respawn, like a video game term. Video… Oh, yeah. And, uh, David, my book agent, was very polite in saying, “Mm, maybe we don’t use the word respawn.

[00:24:49] Maybe we pick something- … a little more, a little more approachable for

[00:24:53] Nathan: everybody.” Also, to be clear, David Bugay, your agent, is also Andy Weir’s agent from The Martian-

[00:24:58] Steve: Yes …

[00:24:58] Nathan: Project Hail Mary.

[00:24:59] Steve: Right. So imagine- … the guy representing, like, the nerdiest author on the planet telling me, “Mm, maybe this is- “Maybe it’s a little-”

[00:25:04] a little too

[00:25:04] Nathan: nerdy.” “You’ve gone too far, Steve.”

[00:25:08] Steve: Right. So tells me to reel it in. So I said, “Okay, fine. How about restart? This is what we do better than anybody.” Yeah. We’ve trained, we… You know, we’ve had 50,000 customers- Yeah … using the Nerd Fitness Academy, which is this course we had back in the day. 20,000 people have gone through Nerd Fitness coaching.

[00:25:22] Mm. So we know our audience, and we know how people work. We know exactly, like, three weeks in, life is gonna happen.

[00:25:31] Nathan: Right.

[00:25:31] Steve: They’re gonna beat themselves up, and they’re gonna want to give up, or they’re gonna give up on their first thing and say, “Fantastic. Welcome to the club. Let’s do things differently.”

[00:25:40] Mm-hmm. So I sold the book as Restart. I have an audience of nerds. I have this company that I’ve built.

[00:25:45] Nathan: Mm-hmm.

[00:25:46] Steve: These are the tips and tactics that we’ve used to help 20,000 normal, busy, burned-out people who- Yeah … who feel really bad about themselves because they can’t follow the Instagram influencer. They don’t relate to the 4:00 AM protocol, ice bath- Mm

[00:26:03] whatever. They don’t like… You know, like, that’s not them. They have jobs and f- families and obligations and things. So that was the premise, and then I went through all of these things, and the book evolved from just like, “Hey, after you’ve given up on a resolution, here’s what to do next,” to, “Hey, if you have failed and you feel like a failure-” I want you to pick up this book.

[00:26:29] Mm. I’m… I wrote the hell out of it. Here’s how I’ve failed. Here’s some famous failures in history. Here’s a protocol that you can follow so that you don’t get caught in this loop in your brain of, “I’m a loser, I can’t follow through.” And we’re gonna get through this together, you and me, uh, you the reader, me the author.

[00:26:49] Mm-hmm. We’re gonna find a way to have some fun with it. We’re gonna stop beating ourselves up, and you’re gonna come out the other side with a better understanding so that when the next failure happens, it’s no longer life-altering. It’s no longer-

[00:27:02] Nathan: Right …

[00:27:03] Steve: uh, it’s no longer self-judg- you don’t have to judge yourself anymore.

[00:27:05] You can just say like, “Okay, that happened. We’re gonna, we’re gonna try again, but we’re gonna try again differently, and we’re gonna move through life with this new kinda life philosophy that honors the weird life that we have to live, the complete uncertainty that life is, and the things that make us who we are.”

[00:27:23] Nathan: Yeah. I feel like the first version of the book maybe that you sold, it has more of a you’re in the mud and I’m the guide kind of feel to it. Sure. And the book that I read is like, I am right in it with you side by side, and let me… You know, it’s just, it’s so much more raw and real, and it’s like, oh, okay, Steve’s been through sh- some shit.

[00:27:45] Yeah. I have too. All right, let’s try again.

[00:27:48] Steve: Yeah. And, and I wanted to, I wanted the stories in the book to, to reflect that too, right? Like, I share this really fun story about, um, Ken Burns, the amazing documentarian. Mm-hmm. You know, everybody knows the story. He talks about how he spent, you know, 10 years making, uh, the Civil War and, uh, however many years it was to be, to do these amazing documentaries.

[00:28:09] And he talks about how it takes, you know, 40 gallons of sap to make one gallon of maple syrup. Mm-hmm. And he has these y- ar- these amazing archives and, um, and hours of footage that he then condenses into, like, the two hours or the 10 hours of amazing… Like, the most amazing documentary you’ve ever seen.

[00:28:27] You know, never moved to New York City. He stayed in, I think he’s in Vermont or New Hampshire. He’s up in New England. And in the story… You know, I’m like, I’m loving this guy. He’s gotta have a great work-life balance, and he’s, he’s got his head screwed on straight, and all of these things. And I was listening to a podcast with him, and the host said something like, “Ken, you’ve had all these accomplishments.”

[00:28:48] How do you keep such a great work-life balance? And he said, “You’ll have to ask my two ex-wives about that.” And it was just, like, this amazing, honest moment- Mm-hmm … from a guy that was like, yeah, man, one, like, life and relationships are hard.

[00:29:03] Nathan: Right.

[00:29:03] Steve: Two, what you see or, like, the narrative you’ve already decided my life is- Mm-hmm

[00:29:08] isn’t the real picture. And also, like, there are some real consequences or things that come from being the best at something.

[00:29:15] Nathan: Right.

[00:29:16] Steve: Sometimes it’s okay to not want to be the best or be a top performer. Like, everything these days is everything must be top, elite, optimized. Mm-hmm. And in these instances, sometimes it’s totally okay that you’re not optimizing and doing all of the things or trying to be the best at something because there are some very real consequences that come with it.

[00:29:36] So for my book, I wanted to be honest about all this stuff.

[00:29:39] Nathan: Right.

[00:29:39] Steve: It takes a lot of work to write a book. It takes a lot of work to have six-pack abs. It takes a lot of work to build a business or run a marathon. Like, it’s totally okay if some of those things are not your thing. You just have to be able to say, like, “I don’t wanna do that.”

[00:29:54] What

[00:29:54] Nathan: were some other big failures that you put into the book of, like… or the fail- failures from history? ‘Cause there are some- Oh … you have some great ones in there where it’s just like, oh, man, I can’t believe that, one, was ever an idea, or two, you know, someone failed that much before actually- Sure

[00:30:07] finding the thing.

[00:30:07] Steve: Yeah. So there’s a, there’s a traveling museum called The Museum of Failure.

[00:30:11] Nathan: Okay.

[00:30:12] Steve: And I went to it in New York City, and it’s… I think it’s, uh, Dr. Samuel West, I believe. Um, it’s just some of the world’s, like, most greatest failures, flops, and, and frauds. Um, some of the things you’ll… that were in there, I think you’ll be…

[00:30:27] you’ll, you’ll remember. You know, like, a Microsoft Zune player was in there. Oh, yes. Yep. Remember the Zune MP3 player? Yep.

[00:30:32] Nathan: Oh, yeah. Yep. The iPod killer.

[00:30:33] Steve: iPod killer. Didn’t, didn’t, didn’t quite work out that way.

[00:30:37] Nathan: The iPod did get killed- … but by the iPhone- Yes … years later, not by the Zune.

[00:30:41] Steve: Right. And everybody talks about, like, oh, Apple cannibalized its own product.

[00:30:44] It’s like, yeah, but with, like, a more expensive, better product. So actually, it kind of worked out. Like, that was, like, baller move. Yeah. But Apple was also in the Museum of Failure. Mm. They had a, a video game console called the Pippin. I’ve ne- I… Before reading the book, I had never heard of this. I had never heard of it.

[00:31:00] I, I grew up as a gamer. Right. Like, that was my life. Um, and

[00:31:04] Nathan: I never- You have video game references for all, all through all of your writing.

[00:31:08] Steve: And I had- Never heard of it … never heard of the Pippin. Um, Nintendo had the Virtual Boy in there- Okay … which was this red, black and red headset that, like, strained kids’ eyes and was discontinued after a year.

[00:31:19] Um, I think my favorite was, uh, Hooters Air. I just think about this all the time

[00:31:27] Nathan: This is an airline.

[00:31:28] Steve: It’s an airline from the, the restaurant- … that sold chicken wings. Like, think of how many people had to say yes to, “Hey, like, we make chicken wings.”

[00:31:40] Nathan: Mm-hmm.

[00:31:41] Steve: How hard could it possibly be to run a profitable airline?

[00:31:44] Right? Like, whenever I’m feeling bad about a decision I’ve made or something I’m struggling with or a project didn’t go according to plan, I’m like, “Well-

[00:31:54] Nathan: It wasn’t

[00:31:55] Steve: Hooters Air … it wasn’t Hooters Air. And honestly, like, whoever came up with it and got that across the finish line, like, honestly, more props to you.

[00:32:01] Like, you must be a hell of a salesman. So, uh, it’s funny. Th- this museum is full of these things, and it’s traveling around the world, so it might be in a city, um, you know, I’m not sure which city it is, but it’s called The Museum of Failure.

[00:32:13] Nathan: Yeah.

[00:32:13] Steve: The best part of this museum is on the way out, they had this wall called The Wall of Failure, and it was a kaleidoscope of Post-it Notes.

[00:32:24] Nathan: Okay.

[00:32:24] Steve: Everybody was encouraged to write down their biggest failure on the Post-it Note and put it up on the wall And you look at, it’s multicolored, it’s from one corner to the other, and it was, like, the most uplifting thing I’ve ever seen. Not because, like, Hooters air. I’m not thinking like, “Oh, it could be worse.”

[00:32:41] But rather, like, it made me feel so, so much less alone-

[00:32:45] Nathan: Mm …

[00:32:46] Steve: with the things I was struggling with or the failures I had. You know, there were signs that said three failed businesses, two failed marriages. Um, two… My favorite one was, uh, tried to cut my own bangs. And then you can

[00:33:02] Nathan: visualize it. You’re just like-

[00:33:03] Steve: You’re like, “Yep, I get it.”

[00:33:04] Yeah. And then the last one said, “I farted in yoga.” Like, that poor person probably has never gone back to a yoga class ever again.

[00:33:12] Nathan: Yep.

[00:33:12] Steve: But I’m looking at this wall of failure and it was so uplifting- Mm … because it made me realize that the failures I had or the business struggles I went through was, like, the most human thing- Right

[00:33:23] I could have possibly done at that time. So- Mm … um, failure is something that it, uh, has b- you know, started maybe in draft one or two, was towards the middle of the book. Like what- Yeah … happens after your next failure? And eventually became chapter one. Like- Mm-hmm … welcome to failure. We’re all here. Let’s talk through it.

[00:33:41] Like you said, we’re all in the mud together. Right. We’re gonna, we’re gonna lock arms and we’re gonna crawl through this sludge. Um, I’m gonna tell you some pretty funny jokes along the way that she’ll make you roll your eyes, and we’ll get through this together. And once we kind of fix failure- Mm-hmm … we can then talk about, okay, that happened.

[00:33:58] What do we do? What do we do next?

[00:34:00] Nathan: Yeah,

[00:34:01] Steve: I love that. Okay. So I don’t wanna give away the whole book ’cause it’s totally worth reading. Sure. But the PACT framework. Yes. Like what is, what… When do you apply that and what is it? Sure. So I wanted to come up with something, like, this is not like a top secret protocol.

[00:34:16] Nathan: Yeah.

[00:34:17] Steve: It’s not like the thing that will solve all of your problems, but it’s something you will remember. Mm-hmm. So I, I think of it as you make a pact with yourself. Mm-hmm. So P stands for pause, AKA step one. Like, don’t make things worse. Or-

[00:34:31] Nathan: If you, if you’re digging your own grave- Yeah … stop digging.

[00:34:33] Steve: Yeah.

[00:34:33] Right. There’s that great quote from CS Lewis. I think he says something like, uh, you know, the, if the n- if you realize the next step for you or you’re on the wrong path, the next step, the next correct step is back towards where you came. So for me, I’m like, that’s true, but also actually the next step is to stop walking.

[00:34:51] Nathan: Right.

[00:34:52] Steve: We need to pause first-

[00:34:53] Nathan: Mm-hmm …

[00:34:54] Steve: and figure out like, am I doing the thing- I- is this working? Or do I actually want to train for a 5K again even though I don’t like 5K? Or I’m trying to make this, I’m trying to make Instagram work, which I keep trying to do. Uh, and I’m like, “I don’t like it.” Okay, cool.

[00:35:11] We’re gonna pause. Step two is accept, so A is for accept, and that’s essentially accepting reality. Like, hey man, you have kids. You have a, a life to manage. You have, um… Maybe you have a husband or a wife or a spouse that, um, works two jobs and your time is limited. Like, it’s essentially being honest with yourself, which is so hard, and accepting what’s happening in your situation.

[00:35:41] Um, C is for change. So if you just try, try again the same way, you’ll probably fail, fail again the same way, right?

[00:35:50] Nathan: Yeah.

[00:35:51] Steve: So essentially you’re gonna look back at how you failed in the past with no judgment. Mm-hmm. That was, that was an old version of you. Like, that’s okay. Yeah. But something has to be done differently.

[00:36:01] So how do we look at this like a fun, curious experiment and change something for this next attempt? And then T, obviously the most important word, is for try. Mm. Like, so pause, accept, change, try. And for the try- It’s not just, like, put your head down and do it. Mm. But rather be okay starting ugly, accept the signals life is giving you as you’re trying, and then at the end of your experiment, decide if this is a great path for you.

[00:36:32] Or cool, back to the beginning. Pause, accept, and just navigate this, this framework so that you don’t get caught in this negative cycle in your head, beating yourself up, trying things that are not right for you. You’re actively picking a different path each time, kind of like solving a maze, right? You’re picking a different path until you find the one where you find that strength that you want to double down on and get excited about continuing to do that thing.

[00:36:57] Nathan: I like that framework. I mean, the, the pause and accept, just focusing on that for a minute. There’s so many things that if you understood the full picture of what’s going on in someone’s life, like, you’d be like, “Oh, that’s why you made that decision or, or those things.”

[00:37:11] Steve: Mm-hmm.

[00:37:12] Nathan: You know, like I think about even for my own life, there’s all of these opportunities that I wanna capitalize on, whether it’s, uh, events to go to or business opportunities or ways to scale or get new customers on Kit or things like that.

[00:37:23] Yeah. But I recently had to go through that of, like, the pausing and realizing, okay, a bunch of w- how I’m spending my time isn’t working because of things that my family needed from me. Like what, you know, w- um, what’s going on with my kids, th- where the stage that they’re at and everything like that. And so getting to the point where you’re like, “Oh, okay, I have to…”

[00:37:42] Except, like, I, I can’t change that. Those aren’t things within my control. Sure. You know? It’s like, “Oh, don’t worry about it, we’ll just fix that,” you know, or something like that. You can’t. And so then, like accepting, oh, oh, this season that we’re in, whether it’s for a few weeks or a few years, like, I’m going to have to show up differently.

[00:37:59] Steve: Yeah.

[00:37:59] Nathan: And so then saying, okay, I’m actually… You know, uh, and let me just accept that. I, I can’t force it to be differently. And so then I’m gonna change the way that I show up. Sure. And, uh, you know, I found myself going through the exact same framework and realizing, okay, and here’s the different things I’m gonna try as far as certain interactions or, or a different schedule or, or those things.

[00:38:19] And, like, you just hold it really loosely.

[00:38:21] Steve: Yep.

[00:38:22] Nathan: And I think that’s such an important thing. And it- Well, I

[00:38:24] Steve: was, I was gonna say- Go ahead … not only that, um- I think there are parts of life and times or phases in life, uh, I, I refer to as, like, treading water.

[00:38:33] Nathan: Mm-hmm.

[00:38:33] Steve: You know, you’re doing just enough to stay afloat-

[00:38:35] Nathan: Yeah

[00:38:36] Steve: so that you can survive until tomorrow. Not that you think help may be coming or not, but sometimes if you’re sprinting on writing a book or navigating something in your personal life, or you have young kids, like, maybe half-assing a workout- Right … or working out once a week is, like, the most you can do, and you’re just treading water on that activity.

[00:39:00] You can do that for weeks- Mm … months, years. Like, what’s the least amount I can do to tell myself, like, I’m not giving up, right? We talk about, oh, if you’re not making progress, you’re falling behind. It’s like, actually treading water instead of swimming in the wrong direction, like, is actually, like, the next best option.

[00:39:16] Right. And you can do that forever. While writing this book, I half-assed my workouts for years I own a fitness company. And I felt okay with that- Right … because, like, this is the amount of, um, this is the amount of energy mentally, physically, that I can give to this right now. I’m okay with that. But I had to accept that I’m not gonna be getting stronger.

[00:39:38] Nathan: Right.

[00:39:39] Steve: I had to accept that I’m not making progress in these other ways, but it’s allowing me to focus on the one thing for me that’s the most important, which was getting this book done, healing, like, taking care of myself- Mm-hmm … and what’s going on in my life. Uh, but you have to accept there are constraints that are actually really helpful to acknowledge and accept, ’cause it stops you from always feeling…

[00:40:01] Like, you wake up every day- Yeah … I’m already behind. I have more to do. I’m a failure or a loser because I can’t… In the book I say, like, instead of trying to get better at juggling chainsaws, like, maybe it’s okay that you stop juggling chainsaws, like, for now. Right. You can come back to it later. But for now, you can’t do it all, and that’s okay.

[00:40:22] Something that I’ve noticed in

[00:40:24] Nathan: a lot of our friends who have been doing this for a long time is sort of this idea of everything old is new again. Like, we built these businesses in order to have, uh, to scale it up to a certain level, to make this money, and then we could do the thing that we really love.

[00:40:39] And so many people end up in a similar place to you where, where it’s like, oh, I am not actually… I don’t actually enjoy the scale side of it, I enjoy the writing side of it. Um, and before we dive into that, what I’m curious about is just talking more about those early days. Oof. Right? Chris Guillebeau. Yep.

[00:40:56] So I was in the same position where I think I’ve read a guest post that he wrote on Tim Ferriss’ blog. So I’d read Four Hour Work Week.

[00:41:03] Steve: Yep.

[00:41:04] Nathan: And then I found this Chris Guillebeau guy, and then I think I read his entire site- … cover to cover as if it was a book- Yep … but it was a blo- it was, like, three years of blog posts.

[00:41:15] Steve: Yep.

[00:41:15] Nathan: And then I saw that he was coming to Boise on his book tour in, like, five days, and I went to that. I didn’t end up… He was promoting the first World Domination Summit-

[00:41:25] Steve: Okay …

[00:41:25] Nathan: which you went to.

[00:41:26] Steve: Yep.

[00:41:28] Nathan: And I didn’t go that first year, but I went the second year.

[00:41:30] Steve: Yeah.

[00:41:31] Nathan: And that’s where I met, you know, where we met you, and James Clear, and Corbett Barr, and, you know, uh, Caleb Wojcik, and just- Yeah

[00:41:37] tons and tons of people. Um, but I wanna go back to that early… Like, what was the point where you realized, like, “Oh, I love to write, and I could actually make money doing this”?

[00:41:46] Steve: Sure. I remember the first six months of writing, I think, and I didn’t even know… I don’t even think I had an, an email list yet.

[00:41:53] Nathan: Mm-hmm.

[00:41:54] Steve: I had 100… After six months of writing, I had 100 RSS subscribers. That’s how old school this is. Yeah. My bones are grinding to dust over here- … as a dinosaur. I had 100 RSS subscribers. Yep. And then I saw that Chris had a newsletter, and he sent, like I said, Mondays- Yeah … and Wednesdays. Or Mondays and Thursdays, excuse me.

[00:42:14] So I, I switched my writing. At the time, I didn’t love it. I was writing super short articles that were timely about time-sensitive, you know, something that happened that day or that week, because that was the prevailing wisdom- Right … back then. Oh, man. This… Oh, man, we’re… I’m gonna bring this… I’m gonna land this plane, dude.

[00:42:32] Yeah. Don’t you worry. Uh, talking about old is new again. So back then, short form content was the king. Yeah. You had to write short or… ‘Cause nobody had the time or attention. This is in 2009, dude. People were saying nobody has the time, or energy, or attention span to read longer articles.

[00:42:49] Nathan: Mm-hmm.

[00:42:50] Steve: And then I found Chris, and then I found Brett McKay over at The Art of Manliness.

[00:42:54] Nathan: Yeah.

[00:42:55] Steve: And he wrote long articles full of research, and quotes, and references, and I said I think I wanna try that.

[00:43:03] Nathan: Mm-hmm.

[00:43:03] Steve: And same Adam Baker, who ran- Yeah … Man vs. Debt, wrote an article called How to Not Suck at Blogging, and I read it and I said, “Oh, crap, I suck at blogging.” And I changed it. I started writing longer articles.

[00:43:17] I put way more of my personality into it. Mm. It was evergreen. It was full of nerdy references, thing that most people wouldn’t understand. And to this day I still remember, I got my first comment from a guy. His name was Evan. I have no idea where Evan is these days, but I hope he’s doing well. Evan was the first, like, random stranger who read my site, left a comment, and said like, “Oh, I really like this article about Legend of Zelda,” or something.

[00:43:41] It’s like, “Okay, we have a reader, and we have people signing up for my newsletter.” And then I kept writing, and when I was writing these longer articles, chasing curiosities about big, deep, you know, long-form content, it started to pick up traction. Mm-hmm. And back then it was links on Twitter actually worked, and- Yeah

[00:44:00] my essays started to get bounced around. Brett from Art of Manliness reached out and said, “Hey, I like your website. If you ever wanna write a guest post for me, let me know.” And you know how it i- right? Like, back then a guest post-

[00:44:14] Nathan: Oh, yeah …

[00:44:14] Steve: was like you made it. You won the lottery. It’s like, okay. I spent, I think, six weeks working on this essay for The Art of Manliness, ’cause I loved that website.

[00:44:24] Oh, yeah. And still do. Brett’s, Brett and Kate are amazing. So I, I write this guest post, and then I woke up one day- And I thought my site had got hacked because Google had just put out, like, their Penguin update or some, some SEO algorithm update, and my traffic, like, 100X’d in a day. I legitimately thought it was hacked, and I didn’t know.

[00:44:48] Yeah. So I asked on Twitter, “Something is wrong with my site. Does it… Can anybody tell me, like, am I being hacked or something?” I don’t, I didn’t know what the heck. I didn’t know what SEO was.

[00:44:58] Nathan: Right.

[00:44:59] Steve: I wasn’t writing for SEO. I didn’t know, but all of a sudden, some of my articles jumped to the front page or the top search term for, for Google, and all of a sudden, traffic was, like, just kind of jumped in there.

[00:45:10] So there was something with my writing that kept people reading. Mm. It was e- when I could write in an entertaining way, as you’ve just read in this book, like, I have to make it entertaining. Yeah. Uh, otherwise, it’s not fun for me. So I make it entertaining and realize, like, “Oh, this is what I want to be doing.”

[00:45:30] Yeah, it kind of feels like homework in some ways. I have to publish on Mondays and Thursdays, but those constraints really helped, too- Mm … for my overactive brain. Uh, and I just put my head down for, like, geez, like, a decade. Mm-hmm. And just focused on writing and the craft of writing and getting better, building that audience.

[00:45:50] And speaking of old is new, back then also, the other thing that was really helpful, going to conferences- Yeah … and spending time with people in person. Yeah. So it felt very much like long form blogs- Mm … connecting with people in real life. I mean, think of how many of our friends came from that first or second or third World Domination Summit.

[00:46:08] Nathan: Oh, I mean, dozens.

[00:46:10] Steve: Dozens. Like- And we’ve all been through it, and we all kind of like, oh, shared experience. So, uh, I, like, old is new, man. Oh, short form content is the only thing that works now. Uh, online, it doesn’t work the same way and- Right … um, everything is AI and work remotely, so, like, don’t worry about getting together in person.

[00:46:30] Mm. Go the exact opposite direction on all of those things. Right. Feels like a return to form. For me, it feels like return to home. Mm. It’s like getting back to doing the things and connecting with people in a, in a great way. Yeah, and that’s

[00:46:43] Nathan: what I’ve noticed is it worked back then and it works now of if you write something that’s really valuable- And it’s not in a generic way, but you put your heart and soul or, or your unique voice into it, then people will say like, “Wow, I learned something I didn’t know.

[00:47:01] I learned it from someone that I like and respect, and I learned it in an interesting way. Like, I’m all in.” Yeah. “Just give me a… You know, however I follow you, whether it’s on a social platform or a newsletter, like absolutely.” And then ultimately people are like, “And you know, I got to meet up in person at a book launch party or at any of these other things.”

[00:47:20] Like, community still really matters, and, um, it’s amazing to see like that still work and that still be rewarded.

[00:47:29] Steve: Yeah, I, I think about this a lot. Even with, I think with, with more and more content, the internet getting flooded with more and more content. We love humans, and we love learning from other humans, and we can tell…

[00:47:45] I mean, at least, I, I think I can tell when somebody really put their heart and soul-

[00:47:49] Nathan: Yeah …

[00:47:50] Steve: into something. Mm-hmm. Like, the people that, like, agonize over, like, the placement of, uh, certain words or phrases. Um, I have a section in the book, I talk about comedy and there’s this great quote from Mike Birbiglia who said something like, “Stand-up comedy is, like, the art of it is making it seem like this…

[00:48:10] Make it seem like something that you just came up with and, like, you’re kind of surprised by it.” But really, like, you’ve been practicing it and you tested intonations and you’ve changed words and phrases because they care that much about the craft. Uh, I’m trying to apply that to writing. And similarly, I’ve seen that…

[00:48:28] I got a chance to attend Craft and Commerce last year. Yeah. And that was the first conference I had been to probably since, uh, World Domination Summit a decade earlier or whatever. Right. And I saw the attention to detail. I saw all of my old friends who are still like, “We’re still here.” Mm-hmm. Whether they’re treading water or working on the next activity or working c- with a completely different set of bloggers or YouTubers or whatever.

[00:48:55] It’s like, oh, like, shared experiences. Other people that have been through the mud.

[00:49:00] Nathan: Yeah.

[00:49:00] Steve: Like, we have some people still in the mud and trying to crawl out. Some people that maybe, like, tried the online thing and it didn’t work, but they still want to come see their friends. Like, that community is so powerful, and for me to show up last year, it was truly, like, life-giving.

[00:49:15] Mm. So y- you and your team put on an amazing conference. Um- Thank

[00:49:19] Nathan: you …

[00:49:19] Steve: it inspired… I’ve now attended, like, five conferences in the past year. And, uh, I, I was saying earlier, it kind of feels like college and like, oh, yeah, people that I haven’t seen in a few months- I now just like, “Oh, hey. Hey, Nathan. What’s up, dude?”

[00:49:34] Like, I haven’t seen you in months, but I saw you yesterday- Right … or the day before. And it just felt like I had just seen you a few days prior. Um, it’s so… I think that’s the only way we’re all gonna get through this is relationships, doubling down on your strengths, and, um, finding that craft, that part that you’re, like, willing to obsess over the details on in a way that, like, you just love.

[00:49:57] You cannot help yourself. That’s me and writing. And I, I, I wish I had just stuck with it longer or rather hadn’t kinda taken that detour. Right. Um, because it worked 15 years ago.

[00:50:10] Nathan: Mm-hmm.

[00:50:10] Steve: Going to conferences and writing longform. And now I’m going to conferences and writing longform, in book form or newsletter form.

[00:50:19] Nathan: And it works.

[00:50:19] Steve: And it not only d- it works, but I’ve tried to do so many things recently where- Mm-hmm … like, I’m willing to do this so that I can stop doing it.

[00:50:28] Nathan: Oh, yeah. It’s a means to an end.

[00:50:30] Steve: It’s a means to an end, and I just don’t wanna… Okay, fine. I’ll try it, and I’ll do it, but my whole goal is to stop doing it.

[00:50:36] Like, that’s not a great reason to start doing something. But writing, like, the goal is to keep writing.

[00:50:42] Nathan: Mm-hmm.

[00:50:43] Steve: So many people have asked me, “Oh, you wrote a book. What’s your back, what’s the backend funnel?” Or, “Are you gonna go on a speaking tour?” I’m like, “No. The goal is to write- Write … write more, to write the next book.

[00:50:53] Hopefully, to have an opportunity to do that because I’m getting to do the thing that I love, and that is the means, the end is the means here. Yes, you. Go to Craft and Commerce. Uh, I’ll be there, and, uh, I plan on coming every year, so get used to it.

[00:51:08] Nathan: I love it.

[00:51:09] Steve: Uh, I came last year, and I was like, “Yep, these are my people.”

[00:51:11] And it felt like World Domination Summit back in the day, and I loved it. So if you’re thinking about it, uh, make the trip. Also, Boise is incredible. I had never been. It’s pretty great. Like, oh, I get it. Oh, these mountains- … are so beautiful, and everybody’s hiking, and everybody’s hap… Like, this is great. So,

[00:51:30] Nathan: um, well done, sir.

[00:51:32] That is so special to hear about Craft and Commerce because when World Domination Summit came to an end, we really wanted to make sure that we had… We’re trying to create the successor to that, of, like, this, this place that everyone could come back to, uh, be human, connect with each other, learn, have shared values.

[00:51:53] And so it was so special, like, to see you there, to see Caleb Wojcik there, like, all of these people. Uh, Josh Kaufman is coming. He just told- Yes … said yesterday that he’s coming. Yes. And then, like, we’re even hanging out right before recording this, you know, and, uh, with Sam Vander Wielen, and, and, and she says goodbye before we sit down to record this.

[00:52:10] And we’re like, and we’re all like, “Well, see you in two months,” you know? See you

[00:52:12] Steve: in two months. Um, also, I’ve… Can I tell a quick, funny story about Josh Kaufman?

[00:52:15] Nathan: Yes.

[00:52:16] Steve: Yes. So I met Josh a decade ago. Mm-hmm. Um, James Clear had put together a little writer group back, way back in the day, and I met Josh. I was like, “Okay, this dude is nerdy and a little weird, and I love him.”

[00:52:32] And I came to Craft and Commerce last year, and I was talking with Tim Grahl.

[00:52:36] Nathan: Yep.

[00:52:37] Steve: And had… Who is, I know, a frequent guest on your podcast. Yes, he

[00:52:40] Nathan: is. I think he’s the most-

[00:52:41] Steve: Yep …

[00:52:41] Nathan: most frequent

[00:52:41] Steve: guest. Oh, man. He’s the best, and he lives three minutes from me in Nashville. So I see him all the time. Um, but I was talking to Tim and saying, “Gosh, like, my publisher, like, they’re really happy with the book, but there’s some part of it that just isn’t fitting for me.”

[00:52:55] Mm. And I said to… And Tim said, “You know Josh, right?” I said, “Yeah, I love Josh.” Josh says… Or Tim said, “Josh is the man. Like, he can help. Like, what do you- Mm. And I really struggle asking for help-

[00:53:08] Nathan: Yeah …

[00:53:08] Steve: for anything, which has been weird promoting a book. But, uh, he said, “Just text…” So I texted Josh, and he said… I said, “I, I could use your help.

[00:53:17] Can I get some of your eyes on this book?”

[00:53:19] Nathan: Mm-hmm.

[00:53:19] Steve: And he said, “How soon can you be here?” So I changed my flight. Mm. On the morning home from Craft and Commerce, I flew home a day ear- and I flew directly to, to hang out with Josh.

[00:53:29] Nathan: Yeah.

[00:53:30] Steve: And while I played video games with his son-

[00:53:33] Nathan: Yep. His son’s name is Nathan.

[00:53:34] Yep. I’ve played video games, played Zelda with Nathan before.

[00:53:39] Steve: Um, while playing video games with Nathan, uh, Josh read my book, and he said, “Oh, I got it. This is you. This is the part where it’s maximum Steve.” Mm-hmm. “This is the part where you’re trying to probably sound a little bit too much like James Clear.

[00:53:56] This is the part where you’re trying to sound a little bit too, like, too much like Mark Manson-

[00:54:00] Nathan: Yeah …

[00:54:01] Steve: too much like Oliver Burkeman or Morgan Housel. But this, these parts and this chapter goes, like, this is it, man. This is your book.” And, uh, it was so helpful to have that 10 years of ex- You know, I’ve known him for- Mm

[00:54:16] a decade, and we’ve spent enough time together, even though we don’t live in the same place- Yeah … so that I could text him at a moment’s notice, and he was like, “How can I help?”

[00:54:25] Nathan: Right.

[00:54:25] Steve: Um, and I’m so, so appreciative for that, and I think I ended up with a better book because of it, because I was willing to ask for help.

[00:54:31] Nathan: Mm-hmm.

[00:54:32] Steve: Because of had I not come to Craft and Commerce, I don’t know. Tim might not have had that idea. Right. And I never would’ve… I was like, “I’m struggling with these chapters.” And I was like, “I just need a few more months.” And he said, “You’ve been struggling with the order of those chapters for six months, dude.”

[00:54:46] Nathan: Two more won’t do

[00:54:47] Steve: it. “Tim, maybe you accept that you can’t figure it out right now, and you need some help.” Mm-hmm. And accepting that and having the courage to ask was g- a game changer. So I’m so appreciative to Josh, and that is all downstream of coming to conferences in person, connecting with the right people, and being willing to be, I think, vulnerable in some ways and accepting kind of, like, the challenges that maybe you’re facing and where other people are actually really good at what they do.

[00:55:15] Maybe they can help you do

[00:55:16] Nathan: those things. Maybe. Shocking, I know. Oh, I love that. I actually have a very similar Josh story. But from 24 hours ago. And that is where I also have this book that the publisher says, “Yeah, we’ll do a final copy edit. It’s good to go.” And I’m like, “It’s not yet.” And getting people to review it in detail, like that’s a big ask and all that, so I’m very hesitant to do that.

[00:55:41] Steve: Yep.

[00:55:41] Nathan: And, uh, then yesterday I was like- Josh, would you be, would you, would you help me out on this book? And he’s like, “Send it to me. I’ll, I’ll have it done. I’ll read it on the plane.” You have to go

[00:55:52] Steve: play video games with him. That’s the rule. He will also cook you a lovely smoked brisket from the backyard.

[00:55:57] And then, and then you have to play video games, yeah.

[00:55:59] Nathan: Yes. And so that, yeah, I’m excited for him to dive into my book and, give him-

[00:56:05] Steve: Poor Josh, we’re gonna blow him up here,

[00:56:06] Nathan: but. Give him the Josh Kaufman treatment. He’s like, “I’m trying to write my own book,

[00:56:11] Steve: but all

[00:56:11] Nathan: my

[00:56:11] Steve: friends-”

[00:56:11] Nathan: He’s gotta take all these distractions to help other people with their books.

[00:56:14] Yeah, exactly. Oh, Josh, he’s the best. So I wanna, uh, I wanna wrap up on the idea of, like, longevity and endurance. Sure. So you and I have been doing this for a long time. We met 14 years ago. Y- when I came into this world, you were one of, like, the six people that I knew who was, like, earning a full-time living.

[00:56:32] Y- you know, it’s like you, and Chris, and Liam Abatta, and Josh, um- Yep … Adam Baker. You know, like-

[00:56:37] Steve: Yeah …

[00:56:38] Nathan: this, uh, this small group. And we’ve touched on a few of them already, but I’m curious, what are the things that stand out to you most in the how do you make sure that you can be doing this creative work?

[00:56:49] I’m not even gonna call it, like, as a creator, ’cause that implies the business side of it. Sure. But that you can be doing this creative work 10 years, 20 years

[00:56:56] Steve: from now? Yeah. I think you have to either fall in love with the … It sounds so cliche, right? And I don’t mean like chase your passion and follow your dreams.

[00:57:06] Like, there’s no vision board or m- or whatever. I mean, like, we’re all, we all get a chance to try different aspects of- Mm … this online business thing, and that is the experimentation part. You have to be willing to also then realize, like, oh, something about this path maybe feels a little different. Mm. And then not burning yourself out going down that path.

[00:57:28] I had no problem writing two articles a week for a decade. Yeah. Because it didn’t … I don’t wanna say it didn’t feel like work, but I loved getting better at it. I really, really enjoyed it. The, this other part felt like I was, you know, uh, the, the trying to force myself to become a boss of a bigger company.

[00:57:46] Mm-hmm. And spending my time in, like, leadership training and reading leadership books and all of that, it felt like, it felt like a lot of work. Mm. And it felt like I was struggling through all of it. And after years of this, I finally accepted or finally said to myself, like, “Hey, this other part-

[00:58:04] Nathan: Mm-hmm …

[00:58:04] Steve: you could do that for the rest of your life.”

[00:58:06] Nathan: Right.

[00:58:06] Steve: You get the thing that you’re doing, the goal is to, that you get to keep doing it. Um, so you either have to fall in love with maybe there’s some aspect of the business, or you fall in love with, like, I love taking this from zero to one and handing it off to somebody- Mm … that is more capable of it.

[00:58:23] I love that part of it. I think there is some longevity there. Uh, and there … I won’t tell the story, but there is a story about, um- The worst vacation ever that I start my book with about treading water where a guy falls off a boat in the middle of the night. Um, turns out humans can tread water for quite a while.

[00:58:43] And I’m thinking about this longevity here. You know, the goal is to not just to win, but to not lose, right? Mm-hmm. Like, how can you, how can you be around long enough? Back then we were making, you know, a few bucks and writing, but our expenses were less- Right … than our, um, than our cost of living. Um, or rather the, you know, our revenue was higher than our expenses, and we could write, and you could build a little audience.

[00:59:07] And that, I think, is what’s sustainable because you can stay lo- You don’t have to start making short-term decisions. You can think longer. Yeah. So for me, it was like I’m going to take a few years to go write this book because I’m planning for the next 15, 20 years. I’ve… This is what I’m meant to be doing.

[00:59:24] Nathan: Mm-hmm.

[00:59:25] Steve: I’m willing to tread water on so many other parts of my life, maybe this other business, because I can focus on the thing that will provide that longevity.

[00:59:34] Nathan: Yeah. I think it’s that falling in love with the craft and then surrounding yourself with people who have fallen in love with their craft as well.

[00:59:41] Steve: With their craft. That’s the most important part. And

[00:59:42] Nathan: it doesn’t have to be the same craft. Something that stood out to me once, I was at this entrepreneur, a creator entrepreneur event in Malibu, and it’s this fancy thing, all these investors and, you know, all of that. And people were going around the room, maybe 20 people are all introducing themselves.

[00:59:59] And someone’s like, “Well, I’m a serial entrepreneur,” this and that, “and I’ve got a big YouTube audience, and, you know, I’ve written two books.” Or, uh… Then they’re listing all these things and get around. And it c- gets to Ryan Holiday’s turn, and he goes, “I’m a writer And he just sort of gestures to the next person.

[01:00:14] Yep. And you- And I know his business, like he’s done really a lot of things, but at his core, he is a writer. That is what he wants to do. And he wants to get his message out there to a lot of people. He works with a team so that, you know, he can build a very large email list and all these other things. But at his core, he wants to write.

[01:00:34] And that’s the thing that I’ve seen from, from Ryan, from Mark Manson, from you, is this obsession with the craft of writing. Yep. And just saying, “Oh, so you wrote a book so that you could…” And he’s like, “No, no, I wrote a book because

[01:00:49] Steve: that’s what I’m trying to do.” Yeah. “I wrote a book because I wanna write and I wanna tell these stories, and I wanna impact people in this way.”

[01:00:54] Uh, so I was at a, a s- a similar small group in, I think it was 2020. Mm-hmm. And Ryan was talking about opening his bookstore.

[01:01:01] Nathan: Yeah.

[01:01:01] Steve: But I was also sharing, like, “Man, I’m struggling. I got this team and I wanna do this,” and he was just very plain. He was just like, “Sounds like the decision’s made, dude. Like, what are you, what are you doing?

[01:01:14] Like, go…” Like, he was legitimately confused. I know, yeah. He’s like, “It sounds like you want to write, and you’re not writing, and you have this thing that you don’t want to do, but you’re doing it.” “It sounds like there’s a pretty simple solution here.” And that was February of 2020. Mm-hmm. So, uh, he then went home and obviously opened his bookstore and-

[01:01:34] uh, has been crushing it. Uh- I

[01:01:36] Nathan: think he might have regretted the bookstore for a little bit in the pandemic. And then was like, “Okay, now it’s doing amazing.”

[01:01:41] Steve: Right. Um, but I thought about that a lot, and that group was so helpful. Again, a small group of creative people that care about the craft. Yeah. Right?

[01:01:50] And I took that to heart and came home and said like … Kinda like I said, like, I need to make changes, but then the pandemic, business doubled and was like, “Oh, God.” “Um, okay, uh, well, we’re gonna come back to that later.” But, uh, it was the return to craft- Mm-hmm … and caring about it. Yeah. Like that Mike Birbiglia quote and, um, it’s so, so, so valuable to find other people that most people don’t get the opportunity-

[01:02:13] Nathan: Mm-hmm

[01:02:13] Steve: to find their craft and to care about it enough to be successful We’re lucky, right? I, I feel so lucky that we can be in the room with people that have found it, that feel that enthusiasm, and I feed off of that.

[01:02:26] Nathan: Yeah.

[01:02:26] Steve: And I feel it similarly when I’m doing my craft. And the goal with this is so that I can keep writing.

[01:02:33] Hopefully, it’s been, whatever, 18, nine- 17 years since I started writing, and I hope it’s 17 plus more- Yeah … that I get to keep doing this because it’s truly, like, what I actually enjoy to do.

[01:02:43] Nathan: That’s amazing. Well- It shows in the book, How to Try Again. It’s fantastic, available- Wherever books are sold

[01:02:50] Steve: Everywhere.

[01:02:51] All

[01:02:51] Nathan: right. Around the world. Uh, where should people go to follow your stuff?

[01:02:55] Steve: Yeah.

[01:02:56] Nathan: Read the book, all of those things.

[01:02:57] Steve: So simple. It’s go to howtotryagain.com.

[01:03:00] Nathan: What a great URL.

[01:03:01] Steve: So … Can I tell one final quick story? Yes, let’s do it. Okay. So the working title was Restart-

[01:03:06] Nathan: Uh-huh …

[01:03:07] Steve: through the first two years of writing it.

[01:03:09] And I went to visit my brother in San Diego, and he’s got a lovely niece, and I got sick. She’s, you know, two, is like a walking, walking germ. Uh, so I got sick. I came back to Nashville, lying in bed, couldn’t type, full of, you know, cough medicine, and it just popped into my head. Mm. I was like, I, I knew Restart wasn’t it, but I couldn’t- Yeah

[01:03:27] come up with a title. And then I thought back to t- talking, uh, to, or James, and James is like, “If you can find a title that tells you what the book does-” Mm … and a hook that tells them the, the, the premise of the book. Um, and How to Try Again popped into my head. Mm. So I went on Amazon, and I typed in How to Try Again.

[01:03:47] This sounds very similar to Nerd Fitness. Yeah. I typed in How to Try Again, and nothing popped up. I went to howtotryagain.com, available. Immediately bought. $9. Haven’t even talked, haven’t even talked to my publisher yet. I just bought it. Yeah. And I bought, you know, uh, bought the domain, and then I told the publisher, “Hey, I got this idea for a title.”

[01:04:05] Um, and then I’d like to share so-

[01:04:07] Nathan: Yeah …

[01:04:08] Steve: this is the, the first line on the front of the book is the first line of my book proposal.

[01:04:13] Nathan: Okay.

[01:04:14] Steve: And it, the publishers, it was their idea. A shout-out to St. Martin’s Press. It was their idea to put this on the cover. Um- Some people wake up at 4:00 AM, run 15 miles barefoot, and take an ice bath.

[01:04:25] This book is for the rest of us.

[01:04:27] Nathan: Mm.

[01:04:27] Steve: So this book, um, I wanted the premise to tell you exactly what it does.

[01:04:33] Nathan: Yep.

[01:04:34] Steve: And I wanted the tagline to sell- tell you, like, what kind of humor it is and who exactly it’s for. And, and then I could spend all of my time crafting and working on the, the… what chapters go where- Right

[01:04:45] with Josh’s help. Which words go where, and working my way through it. Um, I’m so proud of it. But if you go to howtotryagain.com, um, it’s available there and literally everywhere books are sold. And I got to read the audiobook, which was a delight. It’s so good. It…

[01:05:00] Nathan: I listened to the audiobook. It makes me so happy- Yes

[01:05:02] to hear you tell your own jokes, laugh at your own jokes and all of that.

[01:05:07] Steve: Thank you very much. I worked really hard on it. I’m so proud of it, and I think it’s gonna help people. That’s amazing. Well, go check out the book. Steve, thank you so much for coming on. Thanks, man.

[01:05:15] Nathan: If you enjoyed this episode, go to YouTube and search The Nathan Barry Show, then hit subscribe and make sure to like the video and drop a comment.

[01:05:23] I’d love to hear what some of your favorite parts of the video were, and also just who else you think we should have on the show. Thank you so much for

[01:05:30] listening.

I’m Nathan Barry. I’m a creator, author, speaker, blogger, designer, and the founder of Kit.

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June 4, 2026 - Podcast

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