[3pt14159]

I've started and sold a bootstrapped company. My partner and I sold for $2m, and I ultimately regretted it.

I would focus on how much money you make on deal close. You might think to yourself, "Hey, I'm totally going to vest that 2 year period, why wouldn't I?" But the post acquisition phase can be extremely depressing and stressful. I developed bruxism and ended up leaving in less than a year. My health is more important to me than my bank account balance, but it still stings only vesting 18% of a deal. If it weren't for the cash on close provision, we'd have made much less.