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It sounds like you were a bootstrapped solo founder in all of these cases? That’s the riskiest path, there are lots of other ways to navigate a career in startu
by jcheng 2y ago
It sounds like you were a bootstrapped solo founder in all of these cases? That’s the riskiest path, there are lots of other ways to navigate a career in startups that are not quite so brutal in odds or in emotional toll. (In the United States at least)
I have had a decently long career in startups (closing in on 30 years) and never once was a founder, in part because I always wanted to make a decent salary. Being an early employee at a decently funded startup has been a great tradeoff for me and my family. Even if all the equity over the years had amounted to nothing, I’d still have had few reasons to regret this path.
- mittermayr 2y agoYeah all bootstrapped, that's correct. And you're absolutely right, it just makes growing/building unreasonably hard at the beginning because the only funds you have are your own, and it's prohibitively expensive to run ads for the first 100k users when self-funded. The crux with investments always seemed to be the shift of power around the second or third raise for those who weren't runaway successes, when founders start to realize that pressure is now coming from two or three sources, self-worth, investors and possibly clients that were sold on promises and now want to see them implemented. In any case, I agree that being not the first but among the first dozen of employees can be a rewarding and fulfilling choice, it shields from the harshest fire but also allows enough flexibility financially to move on the job as well as in your private life, I'd guess.