Working at a startup is overrated, both financially and emotionally

Not even close.

You can quit and go get another job any second of any day with zero consequences.

You have zero financial responsibility or obligations to the investors.

You have zero responsibilities and obligations to clients/customers.

You have zero obligations to financial institutions (banks, loans).

You have zero or little reputation on the line in the industry being addressed. In fact, in most cases competitors will gladly hire you because you have valuable industry-specific experience and training.

I could go on. I see a bunch of comments on this thread painting founders as greedy bastards. All I can say is: I hope you can one day wear those shoes and actually understand reality.

That said, yes, there’s a startup culture that works people to death and often offers dubious outcomes. I really don’t like that at all. In technology some things are very hard. If you don’t work hard it is often impossible to achieve anything of note. I don’t have a problem with that. I am no stranger to 18 hour days, 7 days a week. I get it. A company can’t operate like that forever. If it does, there’s something wrong with it.

As a founder my standard mode of operation is simple: If I am awake, I am working. There’s no way I will demand or request such a thing from anyone else. I am the one whose all-in, not those who work for me.

NOTE: Don’t work for less than you are worth. Option are neat, they could be worth zero or a few million. More often than not they are worth zero. Get fair pay for your work. Assume options are worthless.

We're a five-person legal tech startup and the work environment is far and away the best I've ever experienced. Granted, I've only been a developer in total for four or five years now (including almost three here), but of all the jobs I've had it's the best.

My CTO/supervisor is amazing: smart, funny, likable and with a management style that works for me amazingly well. Mostly hands off, but fully available for deep dives on technical subjects when necessary. At this point I've earned enough trust to be able to just get shit done with minimal oversight, though we do check in daily at least, and keep each other apprised of what we're up to, or interesting things we've come across.

The lack of external forcing agents is probably a win for us at this point. Obviously there's benefits to having a pile of money to burn: we'd probably hire several more developers and really work to hone our product. But for a team with two full-time developers and a really great designer, not to mention extremely smart and talented leadership and sales teams, we're doing great, and ship features at a pace that seems to put to shame similar companies with much larger teams and far more money. Honestly, I have no idea what they're doing with their time.

Still working on that product-market fit though...

Anyway, tl;dr I feel like I hit the jackpot here.

That means vetting a company before joining it, pushing back during negotiations and being willing to walk away, giving necessary feedback to your coworkers regardless of their title, and personally practicing the style of leadership you expect from others.

It takes a team of people though, and if the team isn't solid then you need to either try to fix it or walk away. A good team will build individuals up and support them rather than wear down and exploit them.

I just passed the 5 year mark at my current company. When I joined there were about 30 people, and now it's probably around 400. I took 4 days off this week, but on Friday afternoon I popped into the old "office", which are some portable buildings on a cattle ranch. It turned out to be the once-every-few-years junk cleanup day, and the CEO, possibly a billionaire on paper at this point, was limping around with leather gloves and a sore back, and all he had to talk about was the recent ultrasound of his first baby, and how proud he is of how the company has grown since the last cleanup day.

Jump ship as far and as soon you can.