Ask HN: Should I quit starting companies?

5 points by failedagain 282 days ago | 10 comments

I'm 31. I've started 4 companies, 2 with VC. All of them have failed with middling levels of success. Internally, I am unfazed and my top priority in life is to build cool shit until I die. Externally, I think I look like a confused loser burning my bridges.

For context:

- No formal education, no big logos, but worked my way up in design/eng at VC-backed SaaS for most of my 20s, then:

- 1st company was a simple consultancy. Did modestly well for myself. I shut it down to start the next startup.

- 2nd company was a consumer SaaS app. Had a fantastic launch, made enough to pay me, but I raised a pre-seed, got a cofounder, hired a team, and we fizzled out doing performative hyperscale bullshit (should've just kept doing what worked).

- 3rd company was a design agency. Actually did really well, consistently $3m+/year with <10 people until covid turned us upside down, we never recovered. Shut down last year.

- 4th company was a b2b SaaS app. Raised pre-seed and started to raise seed. Did well in our niche but when momentum slowed, domain expert co-founder threw in the towel and the rest of us couldn't maintain it. Shut down 6 months ago.

My team is loyal to the game, they won't quit until I do. We're now hacking on edge-level RL & robotics and we're close to having a rad demo. But after being modestly rich for years, I'm now 6 months from total broke. A lot of people tell me to take a high paying full-time job to stabilize my career, but I can't give a fuck about comfort when it feels like we're on the edge of something great. Nonetheless, I have to figure out my runway asap. Trailer park is looking like the top option.

We need a lab and at least a million to survive working on this. I'm close with all my VCs, but I'm still their serial loser, and now I'm playing in capital-intensive hardware instead of the internet hypeware I have experience in. Also this isn't like an obvious $100m ARR in 24 months thing. I'm just a weird founder doing weird things. But my only interest is grinding out a robotics platform that I think paves the road for the next million (robotics) devs.

- Has anyone else failed VC backed startups 3+ times?

- After 2 VC failures should I just get a job?

- How fucked am I in general?

leakycap 282 days ago |

Working for others is a great way to support yourself while you build the framework of skills and routines that can support a business.

Freelancing or building your own businesses is more exhausting than having a job, so if you're feeling like a job might provide some relief - at least apply and try to get some interviews. You might be happier.

Don't be too hard on yourself in the meantime.

failedagain 282 days ago | |

Thanks. I think this is what I would advise anyone else. My judgment is surely clouded by fear. My worry is having a job will take away my time for hacking on novel stuff. But perhaps I should consider that the cost of capital.

leakycap 282 days ago | | |

We don't often take our own advice for others because it is easy to think we're different.

Security of income from a job and and ability to explore and build something in your time outside working hours might be what you need. A lot of the companies we all think of as successes started as side jobs at first, it is more than just possible.

~~~

As an aside, if you believe in the numbers game/batters odds "failedagain" as a username is to be expected - just don't be hard on yourself, learn what works and what doesn't and go forward honestly based on what you learned.

bix6 282 days ago |

By my read you’re gonna lose your mind if you get a corporate job. Keep hacking and make something sick. I’d focus on getting some income so you and your team can eat. Then build from there.

Do you really need a mil and a lab? If so maybe an accelerator. SOSV has Hax for example.

failedagain 281 days ago | |

Fair assessment. I will try to spin up my agency to get my people some cash flow and bridge the gap to where an accelerator becomes a good fit.

JohnFen 282 days ago |

It sounds to me like you had two successes out of four attempts. That's actually an unusually high success rate!

If I'm reading it right, your two "failures" (scare quotes because I'd count the 2nd company as a half success) are the VC backed ones. VC backed companies are a particular kind of business -- maybe that's not the style that works best for you? But that's not the only (or necessarily the best, depending) approach to starting a business.

failedagain 282 days ago | |

Encouraging words, well received.

I realize I'm a diva about VC. I definitely prefer capital upfront and a mission to shoot for the moon, but I have to admit that I've only demonstrated success when bootstrapping and running customer dev from the start.

Further thoughts on your point, I seem to have an expectation that I deserve free money to run a science experiment with low chance of big result, with little proof. This isn't how VC works in practice, so if I want funding, I should have built the case for it, or start now.

If it was SaaS, I'd advise bootstrapping product dev with consulting, but I don't see a path to do that with a robotics SDK. The only bootstrapping strategy I can think of is like robotics-for-coders courseware. Not a bad strategy, but that won't keep the lights on.

fuzzfactor 281 days ago | | |

>I seem to have an expectation that I deserve free money

That would be some of the most expensive money of all, and most subject to loss.

>to run a science experiment

That's the entire thing my business was based on, using tonnes of electronics and instrumentation it was very hardware-oriented.

That was my life's work beforehand anyway, I knew I could make money the same old way if I didn't come up with enough new stuff to be able to monetize a solid 1% of it.

I still wouldn't use "other peoples' money" aka capital because the people who wanted to put up money, it was their retirement funds and stuff.

You can't be a capitalist without capital so I've always been a mere entrepreneur and used my own money.

I was wondering what the hardware was but looks like you've got robot-dependent software, if you're not competeing in hardware, and your SDK applies to a robot from only one company, talk to them.

It your technology applies to more than one company, talk to them all.

sunscream89 282 days ago |

Don’t be silly.

Did anyone die?

Did you cheat or deceive anyone?

If you fed yourself and others and did not run afoul of any condemnable laws, YOURE DOING GREAT!!!

ARE YOU F-ING WITH IS ALL RIGHT NOW?

YOU HAVE A TALENT!

Keep shit rolling!

Things fail all the time. Keep failing forward. You definitely need a side kick or competent action based partners.

If you’re getting yourself and other people paid

YOU’RE THE WINNER!

failedagain 282 days ago | |

I used to bring bread to my team, but now I'm driving the team broke. These are married adults.

But this is unexpected and impactful encouragement. Thank you. The pressure to save the day is overwhelming, but this is helping me get clarity and motivation for the mission.