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

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11–20 of 181 posts

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

#11
I left my company due to cofounder conflicts and lack of traction (we had a few customers, but weren't able to raise funding and I didn't see it going anywhere). I was really depressed for a while, and for lack of a better idea started doing freelance/contract development. After a couple of years of that, I got the itch to work on a startup again and decided to come back to the Bay Area for that. I got a job at a seed-funded company as their first employee.

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

#12
post #10

Failed, consulting, startup, failed, consulting, success, failed, job, job, startup, sold, job.

This is a really interesting path. Could you supply more info for each phase? Like a sentence or two and the maybe the time you spent on each?

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

#14
post #13

I've failed myself a few times. It normally consists of a month of bouncing around doing passion projects / thinking before returning to work.

You don't find "returning to work" has a stigma with the bouncing around?

Meaning, startup to "big corp" or "any company" doesn't mind you were bouncing around.

I'm just curious how dev's go through the interview/hiring process with the jumping around like that. As a more Operations dude, it hurts me pretty badly, even though I "jump" a lot with startups. Requires more explanation.

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

#15
During the past 10 years I tried launching startups a few times, failed most of the times within 6-12 months. After each failure I spent 3-6 months trying some more relaxing things (public speaking, dancing, standup comedy), and then got back to doing startups again and again.

Right now I'm quite tired of all that, but fortunately the past micro-startup & investments brought in around $300k which would be enough to live comfortably for ~5 years in Poland.

Right now I'm 30 years old, and the plan is to keep on trying. What changed during the past 10 years is that I'm no longer striving to go all in with a financed business and spend 70-hour workweeks. I don't want to build a billion-dollar business. Instead, I want to build something much smaller which will allow me to have personal life as well.

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

#16
post #14
post #13

I've failed myself a few times. It normally consists of a month of bouncing around doing passion projects / thinking before returning to work.

You don't find "returning to work" has a stigma with the bouncing around? Meaning, startup to "big corp" or "any company" doesn't mind you were bouncing around. I'm just curious how dev's go through the interview/hiring process with the jumping around like that. As a more Operations dude, it hurts me pretty badly, even though I "jump" a lot with startups. Requires more explanation.

It all comes down to the messaging / how you position yourself when you interview. If each 1-2 year stint was a good learning experience and that made you a better ops / dev, then you need to present that on your resumes / cover letters. Also, ideally while doing startups, you've also met a ton of people where you know that if the current project doesn't work out you can always work with / for one of them!

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

#17
2002: Started a small business.

2008: Pivoted to a somewhat more scalable and clearly defined small business.

2011: Started a true startup.

2013: Realized I'd started the wrong startup. Got a job at somebody else's growth stage startup.

~2018: Will start another startup. But this time I'll have a hell of a lot more understanding, expertise, connections, and

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

#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 my startup, but at the time I was under an abominable amount of pressure outside work, and I just sort of shot out sideways, like a watermelon seed being squeezed between thumb and forefinger. I do not regret leaving Apple to do the startup, not in the least.

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

#20
post #14
post #13

I've failed myself a few times. It normally consists of a month of bouncing around doing passion projects / thinking before returning to work.

You don't find "returning to work" has a stigma with the bouncing around? Meaning, startup to "big corp" or "any company" doesn't mind you were bouncing around. I'm just curious how dev's go through the interview/hiring process with the jumping around like that. As a more Operations dude, it hurts me pretty badly, even though I "jump" a lot with startups. Requires more explanation.

You just need to be able to construct a persuasive narrative. Not, "I hated it and so I left" but more "the new gig offered me opportunities not available". I've bounced around a fair amount between long-term gigs, and it's never really been a problem.
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