Ask HN: Crashed founders, what was the point of failure?

I've had some ideas for inventions or companies over the years. They fail before they ever get off the ground because I don't have the flexibility to quit my stable job (or I was a little kid). They likely weren't good or unique ideas anyways.

There’s a pretty big opportunity cost to your time in life. It’s easy to get in sunk cost traps, including bad marriages and startups.

Life is short. Sometimes (as I learned) you need something new. Sometimes it just doesn’t seem to be working and being a kajillionare isn’t what’s most important in life. Sometimes whatever mission or product isn’t what you prioritize or even believe in anymore.

And that can be a good thing!

There’s nothing wrong with regularly reevaluating priorities. In fact too many people say they’re being “persistent” when they’re really just on autopilot and never gaining perspective. Some people are masochistically entrepreneurial by nature, and just go on autopilot doing that when it’s not a healthy thing for them to keep taking extreme professional risks all the time.

Knocking down assumptions and attacking your ideas is a great thing. Very useful when done right but most ideas are shit and will collapse under careful analysis so people dont do it as much because it can be discouraging. But this thing has a formal name - Red Teaming. DoD wrote a great memo on how to do it right. There are other tools to solidify and stress test ideas such as simulation and game-play. I came across these while reading Farsighted. Excellent book.

Serial founder here.

Actual Points of Failure

1) First Company: When I realized the business couldn't scale on my expertise and hours alone. I would never be able to bootstrap enough money to hire/train my first employee. I saw myself charging hourly for this highly-specific and difficult work, forever. I packed my bags and literally moved out-of-state to get a fresh start after realizing this. The company was very profitable until the day I stopped answering calls.

2) Next Company: I couldn't find product market fit. It was cool tech, but there was no income after 6 months of work, no customers, and no foreseeable way to monetize the idea without a miracle. Running a simple business plan is difficult enough; there's no reason to think some Rube Goldberg type of business plan is going to work.

3) Next Company: I found product market fit after 6 months. There were paying customers, a scaleable business model, but I had to be careful how I operated and the industry was dangerous. I figured out exactly what I had to do to succeed and made a pretty penny finding product-market fit, but then quit cold-turkey once things were crystal clear this was the product/service direction.

Failure is just a step in the learning process. Here are some hard-learned lessons:

a) If you build it; nobody will care. If you market it, nobody will care. If you try to give it away for free, nobody will care. EVERYTHING in this world is this difficult. You basically have to sell a commodity that has current demand if you want to get anywhere. If you don't see other businesses that sell your product or service it's because people won't pay for it.

b) I hate saying this: you NEED a business partner. If you build the product; the other person needs to talk to customers and sell it. You don't have enough time to handle everything when customers start calling. Forget this grand idea of training a handful of employees and letting your startup bootstrap itself. The person or people you work with need to be as invested as yourself.

c) A note on the business partner: This needs to be a very special kind of person. You WILL blow up on each other. You WILL have arguments. You WILL consider walking away from the entire business and them. This kind of person needs to be someone where if this happens; you both understand each other, can call each other an idiot, but you will ALWAYS be able to (eventually) drop the issue or figure out a solution.

d) After years of failure it's a little jarring hitting success. All of the sudden you are doubling-down on the business model instead of brainstorming the next pivot. You begin working out sticky scalability issues and operate in partial-failure mode as things start to accelerate and break, while your attention is on the biggest fire.

Final advice: become a cockroach. Blow past the end of your runway and keep going. You'll still be alive when you run out of cash, so get creative and keep moving forward. What would you expect it to cost to build a successful company? It takes everything you have to give, for decades. Just keep pivoting.

I screwed up my life pretty badly by sticking with my startup for more than a decade. All that stuff about "Winners never quit..." I should have quit.

I kept it going in part because I had personally backed a large loan, which came due all at once when we finally folded. That was a very, very bad day for me. I managed to salvage it -- part of the reason I was able to last so long was that I'd had some successes during the dotcom boom. I lost all of that.

I failed to fail fast, which is easy to say in retrospect, but I would have been equally tsked at if I'd let it go without trying harder. Beyond a certain point (a few years) it was clearly just inertia and depression, and bad advice I got from people I brought in to be CEO.

We quit for real when our solitary customer dropped us. They never really understood what we were good for -- a story that I never managed to tell really well, despite still believing in it. The world went in exactly the opposite of the direction we aimed at: high quality data with powerful semantic reasoning.

I did everything wrong, and was really bad at it, including knowing when to quit. My life is going great now, and I'm incredibly fortunate, but if I had two pieces of advice it would be "Don't" and "Listen to your friends who tell you you're being stupid."