
Ask HN: 39, Multiple Failed Startups - rightsaidfred
I’m turning to HN for some guidance, support, and new perspective. Are you a bootstrapped founder?<p>TLDR - spent last 10 years building several bootstrapped startups. I poured everything in, sacrificed it all, obtaining valuable skills and life lessons, but all businesses succumbed and eventually went to zero.<p>Most close friends work @ startups with cushy salaries. Other founder friends raised venture, acqu-hired, or had an exit. Most of them come from privilege homes w&#x2F; family backup support. i don’t.  They don’t share my enthusiasm and think I should quit, get a job. Any job.<p>I’m the only one bootstrapping without a previous exit and privilege family support...and now 1 year away from 40. I’ve been living ramen lifestyle for most of my 30s and running low on $. I’m still eager to build, to get back up, but the mental battles are immense. Alternating between hope, perseverance, and great sadness, pressure, defeat, and frustration.<p>Applied for multiple mktg&#x2F;product jobs. Told I was too senior or entrepreneurial, or another candidate had more applicable experience.<p>I’m at a cross roads. Should I continue battling in the bootstrapped trenches? When talking with potential employers or even loose discussions with investors, I feel like a dinosaur and far removed from the “what have you done recently”<p>Are there any other bootstrapped founders in 40s here? How did you manage? Any wise words
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throwa17932
I smell a burnout, not a small one, but a late-stage one.

I am 48, working on my own bootstrapped projects for 20 years. They are
profitable and pay my rent, some travel. Life is good, but I am far from rich.

A few years ago I started to worry about the future because it is getting
harder to build something successful and I am not sure this lifestyle will
still work in the future. Next step was losing the fun on programming.
Something like a burnout started. But I still marched on hoping the next
project would not just be ok but a winner. It didn't happen but I had a heart
attack and my private life started to deteriorate.

Now I am doing nothing and try to learn stuff which doesn't have to do
anything with computers. In hindsight, I think it would have been better to do
this when I lost fun programming.

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bitcrazy
I am in the same position except 7 years earlier and on my first bootstrapped
startup. Any general advice to your younger self?

Funnily enough there's another thread on HN for someone about to embark on
this journey:
[https://news.ycombinator.com/item?id=23475890](https://news.ycombinator.com/item?id=23475890)

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discordance
> Alternating between hope, perseverance, and great sadness, pressure, defeat,
> and frustration

Sounds like the typical startup emotional rollercoaster. All I can say is,
don’t neglect your mental health for too long.

Don’t fret too much if you end up taking a job for a while. Treat it as if you
are recharging your financial and mental battery before trying at another
start up.

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Simulacrum0
i'm 48 and have run 2 startups over the past 25 years...it can be an intense
roller coaster of a journey and i empathize with your struggle. May you find
what you are seeking and may you find balance between your mental health and
entrepreneurial goals. None of this is easy nor guaranteed. Having a steady
income, safety-fund, and building towards retirement certainly is a safe and
worthy path. So is following your dreams and working towards 'creating'
something profitable or impactful. Hope you can find both;

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checker659
That's very inspiring. Could you share what you've built?

