I am 64, and worked in many startups, from 1988 through 2013. My main criteria for evaulating a startup were interesting work, and potential financial reward. I would also try to avoid companies whose business model didn't make sense to me. This worked out pretty well. I started out on an academic path, went to an industrial research lab in the 80s, and this led me to the startup world, where some ideas in software research were used as the basis of innovative products. I wasn't comfortable as a pure academic, and I loved writing software, so this was the right path for me.
At each new company, my thought was: if the business fails, at least I've had fun and worked on interesting software. And this often worked out very well:
- Startup 1: The company was building an innovative product, really a new category of software. I was given responsibility for one huge part of it, and this was my first job ever in which I was being paid to create software (as opposed to research). The company had a modest IPO. Nice payout. In my last couple of years, I started a new project which was rejected by the company. But this led to ...
- Startup 2: I took a summer off, built software based on my ideas, and merged with a startup that had complementary ideas. We needed each other. So much fun. This company was acquired toward the end of the dotcom bubble. Nice payout.
- Startup 3: Post bubble explosion, my choices were a consumer startup or interesting tech at a non-startup. I chose the consumer startup. Pretty dull, although fascinating from a sociological point of view. I left when I got bored and tech startups were happening again. Minor payout a few years later when they were acquired.
- Startup 4: My favorite. Fascinating project, three key pieces, I built one of them. I also really enjoyed building the tools to support the development and troubleshooting work. Acquired by a huge company. Nice payout.
- Startup 5: Really interesting idea. I loved the idea so much that I missed the fact it should have been a feature of a product, not a product by itself. Oops.