Joined a company as a very early employee. The company became successful (200+ employees, mid 8 figures revenues), but founders just won't sell it: instead of humbly admitting the luck we had (it's always about luck, I was in the front row seat the whole time so I can definitely and objectively state it) and take risk off the table, they are doubling down trying to make it much bigger (targeting mid 9 figures revenues, and they just took a HUGE investment round with a stellar valuation, which essentially prices us at beyond-perfect execution, so it's significantly risky). In the meantime, I am completely burned out and would just like to put an end to this adventure which lasted 5+ years, but I can't.

I can't leave due to my stock options otherwise expiring (standard 90 days window), and I don't want to put the liquidity necessary to exercise them and leave, too risky due to the appreciation of those shares, nor I want to take out a loan or stuff like esofund which will eat into 50% of my profits, and would still leave me with a taxable event if the company went belly up and the loan was forgiven. So, I'm a typical example of "golden handcuffed".

So, my "never again": never again work for founders who are already rich and are not looking for a reasonably early exit in case of success. My fault for not checking during the interview process, but I was young and naive.

If the founders were not already extremely affluent, I could assure you they would have already sold the company by now (probably at the 2-3 years mark), very likely realizing low 8 figures profits for themselves (and low 7 figures profits for me), whereas they are now shooting for high 8/low 9 figures for themselves, "hurting" me by exposing me to insane time cost opportunity, and also making the whole thing much riskier since as you grow your acquirer pool shrinks dramatically.

Realistically, I end up being a rest and vest employee, meaning I don't do much work these days, and I likely won't get fired since I have so much context, so I spend a lot of my working time avoiding getting burned out and mostly learning about new technologies, but it's still much less than ideal and it's hurting both me and the company.

At the same time, my emotions these days are very weird and nothing I ever thought I would ever experience: I am usually equally happy if the announced quarter results are a big win (meaning my equity valuation is preserved) or a big loss (meaning we are approaching the end of this company so I'll be free without having to voluntarily forfeit a potentially large payout).