I’ve failed a lot, more than most people would care to admit, and I’m proud of it. Everything below is something I bet on myself to build, and most of it didn’t work. That’s the point. Each failure taught me something a steady paycheck never could. My day jobs as an engineer and manager aren’t on this list, only what I built for myself.
2010-2013 · pro gaming. Semi-pro League of Legends. I started on top lane, then switched to jungle and climbed to around 2750 elo in Season 2, good enough to solo queue against pros and scrim with pros and semi-pros. I wanted to make it work, but the pieces never quite fit. Pro gaming was an opaque path back then with no clear way in, and I couldn’t make a convincing case for it. My parents didn’t see it as a real career, and I wasn’t able to explain it well enough to change their minds. By Season 3 I put more into school, and that was that. It didn’t pan out as a career, but that’s around when I started learning to code. Lesson: talent without a path to get paid is just a hobby. I was early to a real industry, but being early without the conviction to back it is the same as being wrong.
2015-2022 · writing. Writing tech articles, tutorials, and listicles, paid through the Medium Partner Program. That was the gig, and for a while it actually paid the bills. Then Medium lost ground in tech and the payouts dried up. The platform got flooded with low-effort, mass-produced filler, and the good writing drowned in the noise. Lesson: if you build your income on a platform you don’t own, you’re renting it. When Medium’s economics changed, mine did too, and I had no vote.
2018 · startup 1. A recipe site (lol). I wanted to learn Meteor.js and scratch my own itch: I wanted to cook more but never knew what to make, so I built a site to browse recipes. I shut it down not long after. The space was saturated with established brands that already owned the search rankings, and I had no edge to take them on. Lesson: know how it makes money before you build it. A content site needs enormous traffic just to clear minimum wage, and I’d confused shipping something with building a business.
2018 · startup 2. Linktree, but for crypto addresses. I branded it at the time as one payment link for all your crypto: you put every address under a single link and shared that. I had no idea how to monetize it and wasn’t business-savvy enough to figure it out. Lesson: a free utility anyone can clone is a feature, not a company. “Useful” and “fundable” are different questions, and I never asked the second.
2019 · startup 3. A mashup of LinkedIn and Crunchbase. One place to look up a person and the company behind them at once: who works where, who raised what, who to reach out to. Handy for sales and recruiting on paper. In reality the data was a pain to keep fresh, I had no distribution, and I drifted off before working out who would actually pay for it. Lesson: reselling data you don’t own is a treadmill, not a moat. The build was never the hard part. Distribution and a reason to pay were, and I’d skipped both.
2022 · startup 4. Reddit, but for podcasts. You could submit podcast links, upvote and downvote them, and leave comments, so the best episodes would rise to the top instead of getting buried in someone’s feed. I liked the idea of a community-curated front page for audio. It never reached the critical mass a voting site needs: with too few users there was nothing to vote on, and with nothing to vote on nobody stuck around. A classic cold-start problem, and I had no plan to solve it. Lesson: a community product is worthless until it’s crowded, so the only question that matters is how you get the first thousand people. I had no answer.
2023 · startup 5. Burned out on tech, so I pivoted to fashion design and launched two brands: a clothing label and a 3D-printed jewelry line. It actually went well for a while, but I shut both down. Not enough traction to justify keeping at it, and not enough passion to push through that. Lesson: work on something you care about deeply. Passion is the fuel for the unglamorous middle, and without it even a business that’s working won’t hold you.
2023 · startup 6. A text-based dating site. I was in a relationship at the time, but I still thought there was a market for something more conversation-first than the swipe apps. I built it and then never launched it, because I didn’t want my name attached to the dating scene. Lesson: if you won’t put your name on it, you’ve already decided. I just figured that out after building it instead of before.
2024 · startup 7. A hiring platform for developers. You could filter jobs by the tech stack you actually work in to find roles that fit, and build a profile so companies reached out to you instead of you applying to them. Too much competition in the space, and not enough passion on my end to outlast it. Lesson: entering a crowded market without an unfair edge is volunteering to lose slowly. “Better” isn’t an edge, “different in a way that matters” is.
2025 · startup 8. A dashboard for engineering managers to run their org. It tracked the metrics that actually tell you how a team is doing: cycle time, how long code takes to ship, PR review turnaround, deployment frequency, change failure rate, and lead time for changes. I gave up before launch. Somewhere along the way I realized I wasn’t passionate about the problem, and forcing it felt worse than walking away. Lesson: only build problems you’d happily live inside for a decade, because you’ll have to. I quit before launch, and quitting early beats quitting late.
2025 · startup 9. You’d tell an AI what you wanted to learn, and it would point you to vetted resources and courses instead of the pile of low-effort tutorials out there. I built my own vector database stuffed with the good stuff to power the recommendations. I closed it because AI search got too good too fast: Perplexity, Claude, and Google now do the same thing well enough that there was no room to compete. Lesson: don’t build in the path of where the giants are already heading. When your core feature is a roadmap item for Google and OpenAI, you’re a placeholder, not a competitor.
2026 · startup 10. 0xinsider, the intelligence layer for prediction markets. A coworker got me into it. In a random conversation she mentioned her husband builds Polymarket bots, and I wanted to see what all the fuss was about. I went down the rabbit hole and never came back. I’m still building it, I love it, and I plan to be at this one for many years. After everything above, this is the one I’m all in on. Lesson: everything before this is why it’s different. A market I’m obsessed with, a clear way to get paid, an edge in the data, and the conviction to stay. The failures weren’t detours, they were tuition.