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.
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/ family backup support. i don’t. They don’t share my enthusiasm and think I should quit, get a job. Any job.
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.
Applied for multiple mktg/product jobs. Told I was too senior or entrepreneurial, or another candidate had more applicable experience.
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”
Are there any other bootstrapped founders in 40s here? How did you manage? Any wise words
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.
Funnily enough there's another thread on HN for someone about to embark on this journey: https://news.ycombinator.com/item?id=23475890
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.