One Year of Betting on Myself

The fears, the math, and the part nobody tells you about getting over the edge.

A year ago I left a job I’d held for over a decade.

InsideTracker had been the constant since 2014, the floor underneath everything else I was building on the side. For The Long Run since 2019. Long Run Labs coming soon. The Huddle taking shape. A few angel checks here and there. But the W-2 was the thing that made all of it feel safe to attempt, and the day I gave it up was the day I lost the ability to hide from whether any of the rest of it actually worked.

I’m writing this mostly for the version of me who hadn’t jumped yet. The one doing the math at the kitchen table, refreshing the spreadsheet, trying to talk himself into it and out of it on the same afternoon. If you’re standing where I was standing, this is the honest account I wish someone had handed me. Not advice. Just what one year actually looked like, including the parts I got wrong.

I had decided I was ready sometime in early 2025. Desire turned out to be the easy part. I’d been talking about leaving for so long, with so many people I trust all nodding along and telling me to go, that the talking had become its own kind of stalling. Everyone agreed I should do it. I still couldn’t make myself do it.

What finally moved me wasn’t more encouragement. It was a forcing function. I was planning to stay with my friend Vivek in Tahoe that June, and I told him not to let me in his house unless I’d quit my job first. I needed a door I couldn’t walk back through. And I knew he’d hold me to it, like any good friend would.

A couple of years earlier, Tony DiPasquale had come on the show. Tony had left a high-paying job as a developer to go out on his own as a videographer, and he said something I didn’t understand at the time: at some point, the cost of staying becomes higher than the cost of leaving. I asked him what that actually felt like, how you’d know. He just told me that when I knew, I’d know. It sounded like a non-answer. It wasn’t. By the spring of 2025 the cost of staying had crept above the cost of leaving, and Tony was right, I knew.

If you’re the person I was a year ago, refreshing the spreadsheet, let me save you the discovery: the math was never the problem. You’ve run the math a hundred times. The thing standing between you and the leap isn’t information, and it isn’t permission, and it definitely isn’t one more person telling you that you’ve got this. It’s a forcing function, and the only one that works is the one you build for yourself, designed specifically to defeat your specific way of talking yourself out of things. Mine was a locked door in Tahoe. Yours will be something else. But you’ll have to build it, because the encouragement of everyone who loves you will carry you right up to the edge and not one inch over.

Here is what I was afraid of, in the order the fears arrived.

First, the obvious one: that I couldn’t piece together enough work to pay my bills. That the income wouldn’t add up and I’d have to crawl back, calling the experiment “fun” but a failure.

Second, and somehow more daunting than it should have been, health insurance. The unglamorous logistics of being a person without an employer.

And third, the fear I didn’t say out loud to many people, because it was the one that actually scared me. I was afraid that going all in would make me lose my edge.

Here’s the thing I’d tell pre-leap me about that whole list, though. I spent all my energy bracing for the money fear, and the money fear was real, but it didn’t show up the way I expected. The hardest part came earlier, and it wasn’t on the list at all: simply making myself jump. The leap turned out to be more survivable than I feared. Deciding to leap was the wall.

What I couldn’t see clearly from inside the fear was how bounded the downside actually was. The CEO of a company I admire was the one who walked me through it. He had me look at where I was spending my time honestly, and pointed out I was living in the most dangerous quadrant, good at the work, but not the work only I could do. And then he did the math with me on the other side: if I left and made no money at all for three to six months, what actually happened? The answer was that I had savings, and the worst case wasn’t ruin. It was going back to get a job. That was it. The parachute I was about to jump with turned out to be far better packed than the free fall in my head had let me believe. The risk was real, but it was a defined, survivable risk, not the bottomless one fear had been selling me.

For years I never needed the sponsorship. That was the whole secret. I could walk away from any deal, any brand, any conversation, because none of it paid my mortgage. That freedom was the source of my best work. I could be honest, I could be patient, I could say no. I could even return a check, as I once did, after their flagship product left me with GI issues I couldn’t ignore. I wasn’t going to promote something my own gut was telling me, literally, not to. The terrifying part of going all in wasn’t that I might fail. It was that succeeding would require me to need the thing I used to be able to walk away from, and I worried that needing it would make me worse at getting it.

That fear was correct, by the way. I want to be clear about that, because the easy version of this essay pretends the fears were silly and they melted away. They didn’t. The fear was right. The edge is real and it is losable. What I got wrong was assuming the only outcome was losing it.

Q1 2026 is when the money fear stopped being hypothetical, and it arrived as something I hadn’t braced for. The way the money moves in this business, the big payments (and opportunities) land between the spring and beginning of winter, which means January through March is a valley. The pipeline and contracts existed. The cash didn’t, not yet at least. And here’s the thing nobody tells you about running a network: contracted and collected are completely different animals, and a good chunk of what eventually moves through your accounts was never yours to keep anyway. It belongs to the shows. So the number at the top can look healthy while the cash in hand is doing something else entirely. For a stretch of weeks I watched the account draw down each month, spending more than was coming in, holding the line on a buffer and a spreadsheet that promised April would arrive. I knew the money was real. It’s a very different thing to know that and to watch your balance shrink anyway, in the quiet, with no employer behind you and the one check still landing a fraction of what I was used to. It’s not the fear of failing outright, but the specific low hum of waiting for contracted money while your own math gets tighter every week. I got through it because I’d put a buffer in place before I needed it. If I could hand pre-leap me one practical thing, it would be that: the buffer is not optional, and the valley is not a sign you were wrong. It’s just the shape of the year.

So, a year in, here is what surprised me.

The revenue came together in a shape I didn’t predict. For The Long Run direct sponsorship landed roughly where I expected. No surprise there, I’d been doing that math for years. The network was the first real surprise: Long Run Labs came in beyond what I’d modeled, and the part that matters more is that I can see the opportunity as far higher than where it is now. There’s a lot of room left in that one. And then the surprise I didn’t know to predict at all, the consulting work, which was something I’d always wanted to do, but wasn’t sure how to actually execute.

One of the workstreams on the consulting side has become market research. This started because Allison from AmazFit asked if I could help her execute a project.

The AmazFit Partnership: What We Built, What We Learned, and What Comes Next

The project itself was a research question dressed up as a campaign. The brand wanted to understand its market gaps and positioning opportunities, where the product could go next, how to keep innovating toward something better, and use data to back up opinions. So we put two watches in the hands of fifty runners, one model or the other, and had them test the watches in their actual training and post about it organically. Not an ad buy. A study with a social footprint. What came back wasn’t impressions. It was signal about how real athletes used the thing, what they reached for, what they wished it did, and what gaps (or opportunities) existed.

Partway through I realized I’d walked through a door I couldn’t see from inside my old building. I wasn’t selling ads against an audience anymore. I was running market research, and I was uniquely set up to do it: I have speed, I have reach into more types of runners than almost anyone, and I lean on AI to handle the infrastructure and the trend analysis so that one person can credibly run something that would normally take a team or far more time than it has taken me. I’m able to fill these opportunities within a day or two, not weeks. The network wasn’t only a media channel. It was a research instrument, and that was a far more valuable thing to be. And watches were just the first version of it. The same setup can test a message, a price, a positioning question, almost anything a brand actually loses sleep over, which is a far bigger surface than one product study made it look.

The proof it was real came later, quietly. Allison told me the work gave her evidence for a case she’d been trying to make inside her own company for a while. That’s the thing I keep coming back to. The deliverable wasn’t a report. It was ammunition for someone trying to move her organization. A few months later I ran a different version of this for Mount to Coast, an ultra running shoe brand, and somewhere in the middle of it the principle finally came into focus: do something that is uniquely this brand, not a thing any brand could run. That became the spine of how I think about this work. We’re running the AmazFit study again now, a tighter version, twenty people around Western States, built on that framework. The campaign any brand could buy is a commodity. The project that only makes sense for one specific brand is not. That second thing is what I want to be in the business of.

You cannot see these doors until you’ve left the building. That’s the part I’d underline for the kitchen-table version of me. The work I was afraid I wouldn’t be able to piece together turned out to include kinds of work I didn’t know were available to me, and the only way to find them was to already be out there, saying yes, paying enough attention to notice when a favor was actually an opening.

The capability story is the same lesson wearing different clothes. A year ago I had a podcast. Now I have a set of properties that feed each other, and the system is worth more than the sum of the parts. None of it existed as a system a year ago. They were just things I was doing. The thing I’d tell pre-leap me is that you can’t design the flywheel in advance. You build the pieces one yes at a time, and at some point you look up and they’re feeding each other.

I’ve also realized that much of what I’ve built and put together suits me and my work-style perfectly. I have ADHD and that brings a whole host of strengths and weaknesses. I’ve been able to mold my day to day (and the tools I use) to take specific advantage of the strengths, and avoid/delegate/enhance the weaknesses in other ways. If you’ve struggled with this and are curious, I’d be happy to share more or chat directly.

And the piece I underrated most was this one. The podcast and this Substack: I thought of them as outputs, things I made on top of the real work. They turned out to be the proof-of-thinking layer, how a partner sees how I think before we ever get on a call. And there’s a longer version of that I only see now. For years the show looked like content. It was really me asking the people I respect how they did the hard things I hadn’t done yet. In 2025, if you were listening closely, I kept circling the same question with nearly every guest who’d built something alone: how did you break stasis, how did you move when moving was terrifying. I told myself I was being a good interviewer. I was interviewing my way toward my own decision. The proof-of-thinking partners value now is just the residue of me trying to learn in public.

I won’t oversell the tidiness. The friction of running a network didn’t disappear, communication and data collection are still hard, and some of that is just the cost of the model. But the work I’m most excited about is the work that didn’t exist for me a year ago: moving past coupon codes into contributing to a brand’s actual business. The two I keep coming back to are the HDYHAU (how did you hear about us) post-purchase survey and the Centium sentiment analysis, and the honest, slightly thrilling part is that the Centium piece isn’t even fully deployed yet. Every brand I’ve shown it to is interested, and nobody else is doing it. The most exciting thing I can offer is still in front of me, which a year ago would have terrified me and now just feels like runway.

So, did I lose my edge?

No. But not because the fear was wrong. The edge is real and losable, and protecting it is now part of the job in a way it never used to be. I just never got pushed to the place where I’d have to find out what desperate felt like, because the work stayed good enough, and good work compounds. The parts I love most, the live podcasts and the panels I get to do so much more often now, are exactly where the edge lives. I didn’t lose it. I followed it.

I keep being asked when I knew it was going to work, and I keep reaching for an answer. Early fall, maybe. But the truth is I’m not sure, and I’ve stopped needing to be. I’m having fun. I feel like I’m making a real contribution to a lot of people. I get to stand on stages and have the conversations I care about, more than I ever did before. Somewhere along the way the question stopped being load-bearing. That, more than any number, is how I know.

One thing hasn’t resolved at all. When someone at a party asks what I do for work, I still don’t know how to answer. A year in, profitable, happy, and the most common question in the world still stumps me.

I’ve decided that’s fine. The people doing the most interesting things rarely have a clean answer to that one either. I’d rather be hard to explain than easy to summarize.

I’ll read this again in a few years. I’m curious which of these fears I’ll have forgotten I ever had.

And if you’ve read this far, thank you. Some of you have been here since the early episodes, when this was a side project I wasn’t sure I’d ever bet on fully. Some of you found it this year. Either way, you’re the reason any of this works. The reading, the listening, the replies, the people who took a chance on the shows and the work, you’re not the audience for the thing I built. You’re part of the thing I built. The thing we’ve built. Thank you for being here for year one. We’re just getting started!

And a special shoutout to my parents for being the entrepreneurial inspiration I’ve seen modeled my whole life!

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This Substack is free and it’s going to stay that way. The paid tier is a tip jar, plain and simple. It’s a way to say this was worth something, and I read every one of those as exactly that. What’s surprised me is who’s hit the subscribe button. Brand marketers have subscribed and told me it’s helping them make better calls. Solo operators have subscribed because the frameworks, especially the AI pieces, actually moved something for them. Others just want to “fill the tip jar.” If you’re one of those people, or you just want to say thanks, that’s what it’s for. And if you never do, you’re still part of this. I’ll see you for year two.