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Ask HN: Founders whose startups have failed, where did life take you afterwards?

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Re: Ask HN: Founders whose startups have failed, where did life take you afterwards?

#71
I spent 2.5 years at a startup and did some of that time working purely for equity. I'm not sure if I count as a "founder", as it was unclear where the founder/employee distinction was, and I'd say that I was probably Employee #1 or #2 rather than "a founder".

The truth? Ugh. The pitch is that, even if you fail, you'll learn a ton and be slotted into a much more senior role in your next job. The reality? Yes, you do learn a lot. However, you get the same kind of job you would've gotten before the startup. Not more. That 2.5 years you spent building a complex product from scratch? Fucking wasted. In your next job, you're still going to be assigned to legacy maintenance, and random bugs and tickets like any other junior, not given real work and a meaningful role.

I consider this pretty dangerous, because there's nothing worse than gaining 2-3 levels in ability, but having to linger at a low level because your startup's failure (which may or may not have been your fault; in my case, it wasn't) invalidates the experience completely. You might fare better, psychologically, if you don't go through the startup and gain levels of experience that you won't be permitted to use in the next job. It's easier to function if you're at-level than if you gain 5 years of experience in 15 months but no one believes you.

It's pretty humiliating and you might break. (This was my Google experience. Granted, I had a rotten manager, but the psychological load of coming off a failed startup didn't help the situation.) I think the whole "nothing bad happens when your startup fails" pitch that you hear from VCs is disingenuous. VCs fix some peoples' careers after startup failure, but that's not going to happen for an early employee (E #2, not really a founder) of a company that didn't even make it to the A round.

This isn't just an issue that I faced. I know plenty of hiring managers who worry about ex-startup people, not because they take the failure to mean anything about the person (for some good news, that stigma is mostly gone) but because they know that people who did startups are (a) a rank level or few beyond where they'd be slotted based on seniority, and (b) have chips on their shoulders. It's a valid concern. When it's an acqui-hire, the founders are usually tired of startup stress and ready to take a (still well-paid and high-status) subordinate role, but after a startup just fails you get someone who feels a need to prove himself and won't be happy being re-slotted to a second-year junior programmer.

So... to answer the question, it's not an easy road. After a short spell at Google, I consulted with a horrible startup (that I've taken off my CV, and that inspired many of my cautions about startups, see: http://michaelochurch.wordpress.com/2012/07/08/dont-waste-yo...) that wanted to hire me as VP/Eng but only if I disparaged, in writing, the work of 10 engineers, many of whose work I knew nothing about. (I turned that offer down.) Then I worked in finance for a while, did a bit of consulting (including lottery design and technology selection) and have done some R&D (new product development and data science) in Baltimore. My life has gotten better, and with the blogging and the fact that I'm starting to know a few things about in-demand fields (machine learning, Haskell, Clojure) I'm now finding reasonable demand for what I can do. It's been a lot of work to get back on track, but I have, and I'm probably stronger for having had to fight this hard.

I think that, in the long run, the experience is good for you. The year after (or few) can be hell. The pitch to the effect of "even if it fails, you'll get a great job afterward" is not really true. It's true for founders who line up with marquee investors and whom the investors really like, but in the average case and for people of average means and connections, the outcome seems to be neutral to negative.

My case is just one data point (and an atypical one) but I think that most veterans of failed startups (early employees hit the hardest, then founders, then late employees) will admit that their careers have been set back, not accelerated, by them. It's certainly not fatal, but it causes a loss of time and, as you get older, you realize just how finite that is.

Re: Ask HN: Founders whose startups have failed, where did life take you afterwards?

#72

I'm a sucker for pain, or it's in my blood, or something. Numerous failures, a few successes, just kept trying. Finally found something that really worked and still doing it, 12+ years later. I will say - I learned way more from the failures than the successes, and they massively shaped my current success. Good luck! :)

What are a few of the most important things you learned?

Re: Ask HN: Founders whose startups have failed, where did life take you afterwards?

#73
Moved to United States and abandoned all the horror stories I faced in my country after what my startup brought me to! You never know, even the failure of your dream company might be the reason you are a live or maybe your life is begging for a new beginning and failure lead to it.

Re: Ask HN: Founders whose startups have failed, where did life take you afterwards?

#74

I'm a sucker for pain, or it's in my blood, or something. Numerous failures, a few successes, just kept trying. Finally found something that really worked and still doing it, 12+ years later. I will say - I learned way more from the failures than the successes, and they massively shaped my current success. Good luck! :)

Funny you would say "in my blood"... any relation to Danny or Angus MacAskill? That last name sticks out in my mind because of those two, weird to see it pop up again. (Or is it just a really common last name?)

Re: Ask HN: Founders whose startups have failed, where did life take you afterwards?

#75

Earlier quoted context omitted.

Intrigued. Do tell more.

http://www.theverge.com/2013/5/8/4276466/jeremy-riney-everyt...

I was a user, still have it embedded on my wedding site (though dead): http://dovandrebe.com/. Hadn't followed what came of it/you. Thanks for sharing your journey!

Re: Ask HN: Founders whose startups have failed, where did life take you afterwards?

#76
post #19

I ran out of gas and left my cofounder; divorced; worked a succession of small startup jobs, some better than others; ended up back at Apple. I have ideas that I cannot express at Apple and so may end up taking another whack at the piñata, now that a) I am not in the throes of a crumbling personal relationship and b) I've gone round the carousel once, so I have some idea how the world works. I regret the way I left m…

Can you give a few quick takeaways from your experiences concerning 'how the world works?'

Re: Ask HN: Founders whose startups have failed, where did life take you afterwards?

#77
I went to work for Facebook then Dropbox, and now I'm on my second startup. We just pivoted, so it sort of feels like the third.

I've worked at a few different kinds of companies, and there are good and bad aspects of each kind of company, each stage of development.

Re: Ask HN: Founders whose startups have failed, where did life take you afterwards?

#78
post #23

Had a startup (rather, small company that was established in the hosting space), sold it when I was 19. Took that money, paid out employees, and tried to start something new and fresh. That failed. Had a co-founder that wasn't dedicated. Had some tech that I could sell and did sell, but I still considered it a failure because I never hit the mark I wanted. Consulted, took some jobs with startups here and there. Those…

You should publish your book of ideas as a GitHub repo and submit it here. It might help you find a perfect cofounder for one of your ideas, etc. Or just get general feedback. :)

Have you seen assembly.com?

Re: Ask HN: Founders whose startups have failed, where did life take you afterwards?

#79
post #31

After a previous failure, my co-founder (and co-brother) and I are moving to the bay area this month, from LA. We're keeping our expenses low and plan to drive for Uber part-time as a way of avoiding day jobs. Even though I'm married and have a newborn, we're sharing a place and living like (healthy) college students. We've both turned down huge salaries to work together indefinitely. I love creating products for peo…

Doing a startup with a sibling, that's always intrigued me. I've thought about talking to my brother about it a few times. Just feels like it might be incurring too much risk to the personal relationship. What is your experience of that aspect of doing a startup like? Kudos got knowing what you want and going for it.

I have a lot of siblings, so I know it wouldn't in most cases. But with my brother it's working great. Knowing each other so well makes it easy to cut to the truth of things. And there's a level of trust that simplifies issues that can otherwise be difficult.

Re: Ask HN: Founders whose startups have failed, where did life take you afterwards?

#80

Since 2009, I have been a founder of 3 different startups (and 10+ different side projects that I couldn't convert to successful products). All 3 failed. My problem was choosing co-founders that either did not have a passion for the idea or just weren't willing to do what it takes to run a business. Someone may be a good developer, designer, or co-worker...but that doesn't mean they will make a good co-founder. I lea…

Were the problematic co-founders you met good friends or not so close friends or acquaintances?
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