Ask HN: 39, Multiple Failed Startups
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