My Failed Startup(s)

Lucky Card - Galaxy - Swizzle

Part 1: Living The Dream

I showed up to San Francisco bright eyed with an $800k pre-seed round to build Lucky Card - a credit card that let you win up to $1m every time you used it (check out hole in one insurance if you're curious how we made that work). The idea is we'd take the interchange and instead of giving 1% back, we'd give it all to one person. It was kind of a cool idea, and the BaaS boom actually made it possible for a 22 year old with 0 experience to make a credit card.

I hired a team of nice people who, like me, ultimately did not know what we were doing. After a few months of (grueling, but understandable in hindsight) compliance work, shiny object syndrome got the better of me. It started to feel like a card that paid most people nothing was objectively worse than every other option. And we'd after Synapse (lol) took their fees and cut, it was hard to see how we'd make money. It didn't help that I had no connection to the type of people who'd use it and probably wouldn't have even used it myself.

In the meantime, during this pre-launch period, I did get to larp around as a "potential billionaire" and go to some cool sf parties. I met Sam Altman. I went to expensive dinners with other founders to glaze each other about being more successful than everyone else.

Part 2: Pivot Hell

I only had one investor who gave me the correct advice, not to pivot. Unfortunately (and incorrectly) I thought I was my next idea was obviously 10x bigger and would not even be *that* hard to build. This process repeated maybe 3 or 4 times, during which I was extremely stressed doing nothing all day. At the time, I thought if I just work really really hard, if I failed I wouldn't regret "not trying." This was the wrong way to go about things. There's like 8 github repos I don't even remember of things that maybe could have worked. But I couldn't get myself to leave that early phase where an idea feels like it's perfect because you haven't actually thought about it deeply yet.

Right in the middle of this, I took psychadelics and told my girlfriend I would not be moving to NYC with her, and instead we could be in a long distance relationship while I restarted my original idea of Lucky Card. It did not work out with the credit card or the girlfriend. Lucky Card turned into Lucky Card But It's Crypto and then Lucky Card For Nightclubs and then Lucky Card Monopoly Version (?) and finally Galaxy.

Part 3: Almost There

Galaxy was kinda good. It started with one of the only good decisions I made - to take a breather. The team decided to make a video game. Hopefully we'd make some money and find a new idea organically. We made a pretty fun mobile game that made a few thousand dollars (the only money this company ever made, btw).

When we built leaderboards, tournaments, and achievements, it boosted our revenue. So we decided to sell that to other game developers. We got some customers. We gave it a pretty respectable effort. At it's peak, it had like 50 games using it and 8m users (more like a few hundred thousand active ones, but 8 million sounds better and it's true that 8 million different people interacted with it). I made myself man the booth at GDC which was 50% horrible and 50% kind of fun. I put my full effort into sales, which I wasn't very good at but I grew from it.

The issue was that ultimately the users didn't really want to buy our off-theme cosmetics and developers wouldn't pay enough for the SDK to even sustain the server costs. Leaderboards aren't that hard to build and mobile developers aren't known for their large budgets. A startup tale as old as time. We did have like 2 customers (shout out Soccer Battle and Katoa) who were genuinely sad about us shutting down, which was nice.

(Side note: We also had like 8 interns who contributed by using the extremely loud Pop A Shot I bought for the office. One of them was pretty smart, but I learned an important lesson about the value of experience.)

Part 4: The Pinch Of Death

At this point, we almost got acqui-hired by Triumph which is now worth >$1B 🫠. Our mutual investor however, was very against it. So we decided to go all in on AI.

Swizzle was the most complicated thing I've ever helped build, and probably the only idea that could have been a big company. It was a full stack app editor in the browser, powered by GPT-3. It didn't work super well, but it would have if we'd hung on until GPT-4. We put VSCode in the browser, spun up ephemeral compute environments, attached a database to each project, included an auth library, and built a pretty cool system that shared types between the frontend and backend. The AI would assist you in everything. I made a promo video of me "coding an app without my hands" by prompting it with my voice.

At this point we had payroll on the order of weeks. One of the two engineers could sense what was coming and left. I was going to keep going until the bank account was literally at $0. The other engineer was down to ride it out with me. 3 days before we ran out of money we launched on Product Hunt and hit #2. I think we signed up like 100 paid users that day.

In retrospect I probably could have kept going, but I was tired. The complexity of the product demanded an enormous amount of energy and focus. I couldn't do it alone, and my other engineer was over it too. Our last payroll had gone out, and I wanted a girlfriend again. The investor who'd been right about pivoting the first time, wanted me to take additional money at an extremely bad (but fair) price. I didn't do it which really made me feel like I let him down, but I had to do what was right for me and I knew in my heart that the money wouldn't fix the burnout. I joined Triumph as a software contractor. I very clearly remember cancelling every Stripe subscription individually, which took like a long time.

Despite a big part of shutting down being horrible, the relief of quitting was immense. Better than the breakups you want. The company had died a long time ago and accepting it was liberating. The air smelled incredible. I finally went outside and felt the sun. No more expectations or the weight of my dream on my shoulders. Just my Juul in the almost-broken BMW Z4 convertible with the top down. That was probably the happiest and most at peace I've ever felt.

Part 5: The Aftermath

I tried working at companies but I was a terrible employee. I have too many negative qualities to have a normal job. I tried working at a botfarm for a bit which was kinda fun. But alas, I am now onto my next startup.