Having been at three "failed" startups in my 15 year (to date) career, I guess I can provide a data point.
I've been involved in the staff and eventual senior management (but not founding) of three small companies in my career: two began as bootstrap startups that morphed into relatively successful lifestyle companies once it became clear we had no scalable product/market fit. They settled into hardware or software consulting, one is pretty sizeable now (a few hundred strong), the other remains under a hundred employees. The final one got to Series B funding but tanked after burning through $15 million.
To summarize, all were highly intense and emotional experiences. I compressed 2-3x the amount of learning I would have otherwise had in most other jobs, particularly in areas where you don't usually get exposure to as a young geek: business development & sales, marketing, HR, finances, etc., and I also became a much better software developer.
That said, small companies, especially if you're involved with steering them, are very personal affairs, and are extremely sensitive the founders' personality quirks while they're under 50 employees. They were hard to work for after a while.
So, in sum:
- Working in a startup is a great experience if you're not in it to get rich, but rather to improve your career by compressing your learning & working on something that inspires you
- Get involved with senior management if you want the experience, but be prepared for the emotional/health toll
- Luck is important, but not just any luck, you want luck that helps you survive - a good market being most important.
I've been involved in the staff and eventual senior management (but not founding) of three small companies in my career: two began as bootstrap startups that morphed into relatively successful lifestyle companies once it became clear we had no scalable product/market fit. They settled into hardware or software consulting, one is pretty sizeable now (a few hundred strong), the other remains under a hundred employees. The final one got to Series B funding but tanked after burning through $15 million.
To summarize, all were highly intense and emotional experiences. I compressed 2-3x the amount of learning I would have otherwise had in most other jobs, particularly in areas where you don't usually get exposure to as a young geek: business development & sales, marketing, HR, finances, etc., and I also became a much better software developer.
That said, small companies, especially if you're involved with steering them, are very personal affairs, and are extremely sensitive the founders' personality quirks while they're under 50 employees. They were hard to work for after a while.
So, in sum:
- Working in a startup is a great experience if you're not in it to get rich, but rather to improve your career by compressing your learning & working on something that inspires you
- Get involved with senior management if you want the experience, but be prepared for the emotional/health toll
- Luck is important, but not just any luck, you want luck that helps you survive - a good market being most important.