How I feel quitting my own startup

I’m not a founder, but I’m the first hire and the first engineer – there since day 2. Six years in, a couple of pivots, and now we have a team of 100 people with a gigantic series A just closed and an excellent PMF. I built most of the product myself – it’s genuinely game-changing and commercial demand is through the roof. Enough equity that if we were acquired now I’d be set for life.

But I just don’t know if I can hack it anymore. The commercial and product teams are pushing wildly unrealistic timelines for new features, which then the technical teams end up the bad guys for not being able to deliver on. Internal communication is all over the place, with nobody seemingly aware of deadlines and deliverables. The CEO is pretty visibly complaining about some teams not working hard enough, because he doesn’t see them in the office or working evenings and weekends. Meanwhile I’m on 18 hour days, under pressure to squeeze performance out of a team that I already think is delivering good quality at a pretty rapid pace, and being badgered constantly to provide KPIs and metrics for them so that the C-suite can deicide if they’re pulling their weight.

It’s almost exactly the opposite of the culture I’d want to create in an engineering team. Instead of teamwork and transparency aimed at producing a cohesive vision, everyone’s pulling in a different direction. Everyone is overworked and making mistakes, and instead of trying to build systems and processes to avoid these issues, it’s become a blame game. The answer to any problem always seems to be “work harder”, rather than providing the resources and support that teams require. Features are being rolled out to customers against engineering advice before they’re finished, meaning a massive drag factor as we scramble to patch them – and engineering leadership desperately trying to protect the rest of the team from having to pay for these decisions. And there’s this message being communicated from the top that suggests technical teams aren’t working hard enough that just feels utterly toxic. I’m probably making it sound worse than it is, but for certain the last six months have stopped being “I’m excited about working on this”.

How do you make the decision that it’s time to call it a day? Is it practically possible to shift the culture? Or is it feasible to detach yourself a little bit from it – concentrate on the areas you can change, and stop caring about those you can’t? I’m a well-paid engineer in an interesting field, and I’m invested financially and emotionally. It’s hard to be objective about whether it's time to quit.

Basically I can sympathise with the emotions you’re going though and thanks for writing about it. Hang in there!

you're on the right track with the detaching yourself, but that can only get you so far. at the end of the day you still need to deliver things that sell. having people who don't know what the fuck they're talking about demand all sorts of wild shit from you is normal.

in the end, it's just difficult. you're being compensated with money and equity - if those aren't up to snuff, negotiate for more. if that doesn't work, you need to make the decision to stay or leave. there's a chance they give you what you want when you threaten to leave - and then you will have some leverage. but just realize this is not ever going to be a walk in the park. millions of dollars are on the line, people are not going to behave rationally because they see you as the limiting factor between them and their riches.

For me it was as close as I could imagine giving up a child would be like, but in hindsight it was the best choice and I grew hugely as a result.