He's known for a long time that he wants to quit, it's just now that he's worked up the nerve to tell you. If you're honest with yourself, I bet you've known it for a long time too.

> I argued that he still has an employee mindset. Founders don't get to quit randomly; we have a responsibility towards investors and employees who stuck with us through all this

...and this is the exact point that you blew it. Why do you think you get to tell him what to do with his life? And why should he put the interests of your empoyees and investors ahead of his own?

He's just not that into (working for) you. He's gone. Let him go and try to salvage what you can.

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.

Most of us don't do startups for the money... obviously it's hard to walk from $500k annually, but if your hearts not in it, that seems justification enough to leave.

>So, found a company yourself. See what you feel like after you've been slogging for a decade or so without any net. It is always super easy to berate the position of someone else when you yourself are taken care of.

>> You lose a bit of that "we're in this together" vibe that makes it organically motivating to work at a place.

>You lost something that you never had in the first place. Founders, employees and investors never have exact alignment of their goals.

Don't startup employees normally take below market wages and work crazy hours to get the company going? They're not in as deep as the founders but they are making sacrifices for the company.

It's not like they are talking about taking on more investment here and everyone's getting diluted. It's the founders giving themselves a little personal enrichment ahead of all the other agreements that the employees agreed to.

Why would you expect the employees to continue to make the sacrifices to keep the company going if you do this?

Wrong choices. Better to stay a few years, then start your own company or consulting business.

And in my experience large corporations, are often more progressive than most startups (work from home, technical equipment, software stack, conferences....).

Just at an FYI to the author, this is a bad idea. Once you have left a startup, your opinions are going to be valued much less by everybody still there because, well, you quit. Your incentives are now not aligned fully, you aren’t part of the mission anymore, and this was because you decided you didn’t want to be.

And from your perspective, you quit. Don’t waste your time on them anymore, fully focus on your next project.

I'm in my late 20s. I have never been a CTO. I spent three years of my life working for a perfectly normal and boring startup that eventually ran out of money and shut down. All the threading bugs I tracked down, all the packages I backported, everything was for "nothing" in the end, except what I learned. My equity vested, and was worth zero.

A few months before they shut down, I got the sense that this company wasn't what I wanted to do with my life, and it wasn't really going anywhere / the technical goals were shifting into something much less ambitious and much less meaningful, and moved across the country to work on another project with a friend (and stay part-time at the old place). I'm very glad I trusted my instincts there.

You'll find something else to do, and you're already better off than most people your age by having the experience you have. Don't hold on to sunk costs.

Been there, done that, can confirm. That was a shitty 2 years, but I’m glad I learned all these lessons in my early 20s rather than later in life (with potentially a mortgage, kids, etc)

> I told my CTO that developing and launching a big, new feature every week wouldn’t be sustainable for me long-term. He told me that that is startup life and that we could talk more about it on Friday with the CEO. On Friday I got fired for not being a good fit.

Sounds like hell, and the CEO is an asshole. Anyone who falls for that bullshit is crazy. But whatever. Young gullible optimistic folks are free to burn themselves out and waste a few years of their limited lifespan making some sociopath his billion dollars while getting paid a wage and some magic beans that might turn out to be worth damn-all.

I don't want to be that kind of founder when I grow up.

Are they really? I think they're workaholics chasing an escape. True success is the worst outcome they could imagine, because then they'd have to tend to the rest of their life. Why be a serial founder, if its so horrible and stressful? Why keep working yourself to death after your first $10M, $100M, or $1B? Why is it never enough?

People have self-destructive instincts that are disguised in socially acceptable (or worse, praised!) forms. We shouldn't ignore the actions of founders when trying to make sense of their words.

I can relate to this. No, I didn't leave my startup. I've worked with three startups altogether, including one of my own, which started off with a co-founder back in 2012. In the not-my-own ones, I was once the founding engineer, and once the fourth engineering hire.

Why didn't I leave my own bootstrapped startup despite the amount of pressure, chaos, uncertainty, and pain, all of which were setting in at the same time? Not to mention immense difficulties in dealing with co-founders and all the social pressures (home life, relationships, real day job at a fortune 500) and burning hard-earned cash to keep the thing running in the face of uncertainty and the very real likeliness of failure.

Why I nearly did walk out:

- Extremely unpleasant co-founder. Unsociable, condescending, biased - for instance I'm quite sure he perceived me as being worth less than himself because I had no wife and kids situation going on. Treating me as employee despite having equal shares in the company. - No VC capital or outside funding. The expectation of having close to 0 in the bank account once the pay-day happens from the "real" job (and rent+bills have already been covered) sucked really, really much.

A few things spring to mind as to why I did not walk out:

- Luck. We seemed to have the right timing. There were almost no products on the market which attempted to solve the problem the way we did. There was a tremendous interest in our product, but we just couldn't get any significant number of people to convert, despite seemingly offering the right product.

- Having listened to feedback and tweaking the product (most notably the pricing/business model), we managed to achieve decent market capture (it took almost 3 years from) and that came mostly as a result of persisting through the cash-burn, listening to and evaluating all customer feedback, and iterating on many aspects of the product dozens of time. Fixing broken things and solving weird edge-cases which weren't weird in retrospect pointed to the fact that we were simply inexperienced. We still pressed on and sought to break through this barrier of having no freaking clue about this emerging market.

- The real break was the actual realisation of the for-reals breakeven. It changed the game - the point at which no money needed to leave our personal bank accounts to pay for cloud services, domains, tax accountants, templates, logos, you name it, was one of the greatest feelings ever. At point-breakeven the whole thing went from a "somewhat successful side-project which has been draining our personal bank accounts" to a project which could potentially provide enduring sustenance, and we might be able to take it further. At that point it became all the more compelling to press on.

Sounds impulsive, but doesn't have to be. It's possible to make that jump after long and thorough consideration. It took me years and a couple of jobs before I finally dared to quit and start my own thing. Not everything I did with my own thing worked out well; spent a lot of time finding my own way, wasted a lot of time, made almost no money in my first year. I did some freelance work, now working on a bigger freelance gig, but I'm really hitting my stride now, and can't wait to go back to my own projects.

I'm not a natural entrepreneur. It took me ages to make this step. Nobody in my extended family has their own company; they all work for a salary. Nobody likes this kind of risk, but I love it. I love the freedom and the uncertainty. I love the risk.

It was a tough decision, and it still seems impulsive compared to a steady salary, but it was the second best decision of my life. (The best was marrying my wife, but that one was surprisingly easy.)

Many of them will have invested years of their life, during which they will have worked incredibly hard, and probably sacrificed life outside of work for their jobs in hopes of that payday to give them the freedom to do what they want to do next: you can hardly blame them.

True riches isn't money, but discretionary time. Unfortunately that discretionary time often costs quite a lot of money to realise.

If it were me I'd be seething with the board at their antics since Friday (and, obviously, for some time before that). They've gone from being one of the most successful and valuable startups in history to an absolute trash fire in the span of four days because of some ridiculous power struggle. They've snatched defeat from the jaws of victory. Yeah, you bet I'd be pissed, and of course I'd follow the person who might help me redeem the future I'd hoped for.

I understand. I'm just saying I did it and got $1m+/yr out of it. I've done startups before that lead nowhere - so I understand the feeling... It's not like joining startups at seed stage or something - I'd only join one with a $XXXm dollar valuation or greater. (And one that has gotten that valuation very quickly hopefully - not over 10 years) I left because of the horrible environment before I vested everything. I decided if I can find a job at $350-400k/yr with some minor upside and a much better culture then I'd probably be happier in the end. (I have about 8 YOE)

One reason that hasn’t been mentioned yet as of this comment: ownership. Your startup is yours. You have the vision, you run the business, and there’s nobody to blame for anything but yourself.

When I was doing game development I got frustrated with the yearly post-mortem where we’d identify what things didn’t go well and what we could do to improve, only to make the same mistakes the next year. The company was relying on ambitious and hard-working people like me to keep fixing the same mistakes and avoid having to do deep planning and make hard decisions early.

With my own company, I still made mistakes but they were my mistakes to make and fix, and I never had to pull overtime to fix someone else’s mistake. I was far happier making a lot less money. (Up to a point… you can’t live on nothing. :P)

There are other benefits like doing both customer relations and engineering, which can make you better at both, and the slim potential for a large payout of FU money, among other things. Running a business isn’t for everyone, but wanting to and being willing to take all the responsibility is one thing you can’t get as a normal employee.

This is just straight up wrong. You don't HAVE to enter the VC cycle of endless raising, and if they're wanting to replace/kick you out, what are you doing wrong?

> eventually jump ship and become a captain of your own vessel.

That's literally what being a co-founder is. You might be even split with someone, but you are still very much the captain.

Hindsight and all that. But still, don't just take on anybody as co-founder, easy come, easy go.

Super tough to read all this, I'm really sorry your hard work did not work out but you've done all that could be required of you and then some.

I very much recognize your trust issues, but over time even that will fade.

I thought this was a key insight, and I'm happy the author is frank about it. Some people enjoy building things from scratch, others enjoy taking a good idea and scaling it. IMO, both are hard problems and its good that he bailed before trying to go down that route.