I am (not) a failure: Lessons learned from six failed startup attempts

There is one other way in which you are not a failure, and I am sure that I am not alone in thinking about it: I have been reading your words for 15 years, from the time I was a baby CS major. That's really true, e.g., here[1] is a comment from 11 years ago where I mentioned that a lisp you wrote for the Apple //e informed a lisp for the Apple //e that I wrote.

Especially in my college years (2009-2013, ish), the world seemed smaller, and to me, a lot of what you wrote was like looking through a keyhole into the real world. Grown-ups can apparently write lisp at JPL[2]! Google was chaotic[3][4][5][6] to work in 2000, especially if you commuted from Burbank. A name change[7]. And, variously, surveillance, more lisp stuff, etc. Now I'm an adult and I still haven't professionally written lisp, but I'm glad to have read about it anyway.

Anyway, it might surprise you to learn that when I think of your writing, though, I think of your HN comments first. There is a kind of influence that you can only get with a steady, unthanked build-up of seemingly-small contributions over a long period of time. In the right place they compound. I probably cite you to other engineers once a month or so.

[1]: https://news.ycombinator.com/item?id=6199857#6200414 ↗ [2]: https://flownet.com/gat/jpl-lisp.html ↗ [3]: https://web.archive.org/web/20080212170839/https://xooglers.blogspot.com/2005/11/hello-world.html ↗ [4]: https://web.archive.org/web/20090408003924/http://xooglers.blogspot.com/2005/11/in-beginning.html ↗ [5]: https://web.archive.org/web/20090408013612/http://xooglers.blogspot.com/2005/11/wormgear-turns.html ↗ [6]: https://web.archive.org/web/20090408003913/http://xooglers.blogspot.com/2005/11/day-one.html ↗ [7]: https://flownet.com/ron/eg-rg-faq.html ↗

That was a good read. What impressive perseverance, and also a positive outlook. But, reading it made my FOMO worse. I guess one has to experience it fully to apply it. Or maybe not.

I quit my job a year ago to pursue my own ideas. Like the author, I had made some money from a IPO. The post-IPO environment with heavy bureaucracy killed the vibe and I quit. Note that it wasn’t a Google tier company, but I made enough money that I could take a risk for some years without income.

For me it has only been a year. But I feel like a huge loser at times. In no scenario will I give up until I’m utterly defeated or captured the castle - I’m not a quitter. But this feeling gnaws at my soul.

I have failed to find a co-founder. Most of my friends are not interested in startups. So, I have had to look elsewhere. Between people who screwed me over equity, people who didn’t want to do the work, and my own imposter syndrome (I’m from a low ranked state college, and people I meet in SF are elites), I feel horrible and alone. I tried and even successfully built some projects over the past year, but ultimately nothing worked out.

Now, I’ve decided screw it. All the advice about sell first and get a co-founder - sounds great on paper. And I have some doubts around that whole belief but that’s not important.

I know actual pain points I’ve faced in my decade long career. I’ve done both highly technical and highly functional work. I’ve talked to enough people and validated my idea. I wish this thing existed and that I’d worked on it sooner instead of trying something different with randoms.

So, I’m just going to go and build it. I like building things, and I’ve gotten enough recommendations and performance reviews that point out that I’m good at delivering value for the customer and making sure my team succeeds.

So I’m building a product. I am able to dogfood my own product as I build it which is great. It’s a somewhat complex, b2b AI enterprise product, and having built multi-billion dollar enterprise software and delivered multiple multi-million dollar implementation projects, I feel that there is really no rush. Most enterprise software and organization processes are awful and not well engineered nor well thought out.

If this fails, whatever. I tried. If it works, amazing. I like building good things and have a track record of doing so, albeit for others.

But I fear I will keep feeling like a failure until it is successful. On the other hand, it would be very cool to build a solo founded enterprise product and deliver actual success.

Anyway, thought I’d share my thoughts it feels good to type it out. Thanks to the author of the article for sharing.

There are many reasons to do a startup, but people should only call it a business when the goal is either a tax deduction mitigation and or rapid entry into profit traction.

1. Don't use some clever or hard to remember name with a weird spelling. While easier to Trademark, the users and customers won't differentiate your site from the sea of attention grabbing garbage.

2. If people have zero paying customers, and zero revenue... than the hard fact is they were never in business, and should have founded a nonprofit instead (common for opensource support service entities.)

3. Often copyright and patents are infeasible for small business, and people simply can't build or defend things like a large firm. Thus, initially design products/services to last maybe a year or simply be disposable... When 270 desperate cloners show up to dilute the market sector... people quickly understand why they can't rely on Android, Steam, or Apple ecosystems to protect their bottom line.

4. There is zero loyalty without treasure. The only people that care if your firm goes into the red is you, and maybe the small-time shareholders. Most people can't take the constant adversarial posture with problematic staff, opinionated shareholders, and high-demand customers. Everyone thinks a CEO is lame till you become a CEO for a year or two... Every conversation from that point on is about money or marketing, and most people keen on building things tend to burn out of the role eventually due to social isolation.

5. No company lasts forever, if the operation is a projected liability it is your job to respond accordingly. Even if that means executing an exit strategy, and firing the entire problematic division.

6. Ask business people about their memorable experiences, and not about their money source. The superficial apparent function of a business is usually very different from the actual revenue model.

Best of luck, =3

There is currently a risk asymmetry in startup world that drives away people who could do good work.

Investors know the long odds of success, so they invest in twenty to thirty companies and wait for one to get big.

Founders and employees can't diversify like that, because you only have so many working years. To mitigate this we have decided to award successful founders with huge paydays as a lure to others to throw their hats in the ring. This has some malign effects, namely unsuccessful founders and employees get bupkis. It also attracts the wrong sort of personality to be a founder, selecting for too much risk appetite. (At least what I consider the wrong sort for building a sustainably profitable business.)

I have an idea for how to solve this and I wonder if it's already been tried or if there are holes in it. The idea is to spread the risk of starting a company across something like an accelerator class. If one company in that class gets big, it would be contractually obligated to hire and grant shares from some pool to other members of that class. This would be at the cost of the winning founders' stakes.

The upside for winners would be much lower, but the downside would be lower too. This would attract a different sort of person to this accelerator, and be a differentiator for selecting talent.

To everybody reading this and having doubts about starting your own venture: DO IT!

Yes it's a lot of risk, yes most startups fail, and yes you could make more money at FANG. However, this is one of the most exciting times to build a startup, thanks to AI.

The big winners of the all the AI advancements (especially OS) are devs and AI startups:

- No more vendor lock-in

- Instead of just wrapping proprietary API endpoints, developers can now integrate AI deeply into their products in a very cost-effective and performant way

- Price race to the bottom with near-instant LLM responses at very low prices are on the horizon

It's as if your product automatically becomes better, cheaper, and more scalable with every major AI advancement. This leads to a powerful flywheel effect: AI improves product -> better product attracts more users -> users generate more data

Besides the product perspective, AI also allows you to operate your startup a lot more efficiently.

Will we see a single-person unicorn soon? Very likely not.

Will we see very successful small and bootstrapped startups? Yes, already the case.