If you put in 5-10 years bootstrapping and made a living, then: 1. You clearly built something of value and should have an exit coming (or already had one) 2.

If you put in 5-10 years bootstrapping and made a living, then: 1. You clearly built something of value and should have an exit coming (or already had one) 2. If you were the victim of some unfortunate circumstance that put you out of business, you probably have made friends or partners in the industry that would instantly recognize your value and bring you on board (I'd personally hire an old competitor in a second) 3. You've probably learned quite a bit that is applicable to engineering, sales, marketing — chances are you don't even identify as a software dev anymore. You might want to shoot for something c-level, exec-level, sales engineering, project management, etc. 4. At this point, you know how to negotiate and market yourself. You will not be victim to some piddling lowball offer unless you're desperate. After 5-10 years in the game, you probably won't be. If that's your only route, take the job and use it as a launchpad to something better like everyone else does. If you bootstrap for 1-12 months and quit (like 90% of my peers have), then right, you'll probably have nothing to show for it.