> As far as retention goes, especially for early employees: technically, you're going to be dealing with all of the bullshit the founders built into the system, and probably handling growing the team and installing processes. If you don't have some actual real stake in the value that you're creating, you are going to get jaded as the inevitable annoyances of being a startup take their toll.

Yeah, I worked at a young startup for almost 3 years, and one of the reasons I quit was because they would neither pay me market value nor give me equity. I made about 3/4 of what everyone told me an engineer of my experience in my location should be making. Hell, I didn't even get health insurance, and the company made a point of hiring most new people as contractors, so they got around Obamacare's 15-employee rule. The company was a year old when I was hired, so I was too new to be considered one of the founding members, but I was still one of the early employees, and I got to create a whole bunch of systems that were integral to the company's operation.

Over time, I got more and more bitter and jaded, and it was affecting my work. I wrote the software platform, and I was our DevOps infrastructure, but all I could think about was that not only did I get paid like shit, but they didn't value what I did enough to offer me equity. It upset me deeply that they would value me so little when I built huge parts of the company from the ground up, and I lost a lot of sleep over it. I already had a huge amount of stress in my life (this was all while I was transitioning from male to female, and I've struggled with depression for decades), and this made it all worse. By the time I quit, I had lost all motivation, and my boss was threatening to fire me because I hadn't been coming up with enough new software to write (he had stopped giving me assignments weeks before that, mind you: I think he was looking for a reason to get rid of me).

There were other reasons I was bitter, too. For example, management treated my transition horribly, and they stood by and did nothing while I was subjected to humiliation for months by building management. It ended when I got the city involved, and I had to do 100% of the work on that myself (and, even then, our CEO almost sabotaged the city's case, because he ran his mouth off on some things where he didn't know what he was talking about). Another was one senior architect making godawful design decisions and being a manipulative, condescending, immature manchild when interacting with others. My boss gave him 100% free reign and treated him as an equal (this despite my boss being the Director of Software and a founding member) and dismissed any and every criticism about him just because the guy was an old friend of his for years. That drove one of my co-workers, who was one of my best friends at the company, to quit, and then my boss proceeded to slander him behind his back just because he had the gall to criticize my boss's friend. In fact, I suspect that the reason he suddenly stopped giving me new assignments and then began threatening to fire me for not doing enough work was because I finally had enough and told him my complaints about his friend. It is entirely within his personality to go out of his way to railroad people who have offended him. Oh, and then there was the total lack of planning or release engineering, despite my best efforts to come up with written proposals on what to do...

I stayed as long as I did because a) my immediate co-workers were wonderful people I'm glad to call "friend", and b) I had come to believe that I was worthless and that I deserved to work at a company that treated me like shit. [Edit: to be fair to them, I'll add c) I actually enjoy doing this kind of work (platform/DevOps), and I really believe in their product. They make the kind of product that, if it takes off, will change a lot of people's lives for the better, and I wanted to be part of it.]

Ultimately, I started looking for a new job, and I took the first offer I got, just to get out of there. Since the new year, I now work at a 20-year-old company, I get paid what I'm worth, I'm insured, and I'm pretty happy here. Still, even after being gone for a few months, the bitterness came back last month when I found out I owed an extra $400 on taxes because I was uninsured thanks to that company. They really did a number on my mental state.