Both times the founders had developed an incredibly negative relationship with their dev shop. Hell, the company with the Series A was withholding payments, the preseed company at least paid their bills.
I naively thought “of course they hate working with a dev shop, the incentives are wrong. I’m FTE with percentage points equity. I’ll fix it.”
Of course, things got better, but growth stalled or never happened, blame gets shifted, suddenly that founder who was excited to hire top tier talent is very disappointed in the very equity and salary expensive engineer you are. You end up being the new target of their animosity. You start to empathize with the folks in India, China, Ukraine or Argentina whose history lingers in the git blame. They’re not stupid, the incentives were just wrong!
The thing is…the CEO who failed to find a technical co-founder, retain them, or replace them with the same equity agreement has already demonstrated their inability to work with technical people. If they are coming from tech, the fact that they couldn’t convince a former colleague to work with them means they’ll be a terrible manager. If they come from finance, as many founders do, you are a line item.
At the end of this, hopefully sooner than later, you’ll quit, you’ll get fired, or you’ll collect paychecks while looking for the next better thing.
As an engineer, stay away from mediocre CEOs.