Startup CEOs who gave up fortunes to turn employees into millionaires

It's worse than that. By the time you factor in preferred shares and other investment dilution, your 0.1% will be more like 0.00001%[+]. Few people think about that, and unless someone is actively looking out for your interests (e.g. someone giving retention grants -- or you demanding them), it's difficult to make a lot of money as an early startup employee. You can easily find yourself in a situation where you vest your grant, leave the company, and later find out that a new hire is making an order of magnitude more money than you in an exit. That's startup life.

The game here is predicting the expected value of an extremely improbable future event, and sacrificing present day money in favor of that event. There's no "fair" way to do it, so if a founder is asking that kind of commitment of you, they should be looking out for your interests over the long term as well.

[+] edit: I overstated my case here. You can probably expect 1-2 orders of magnitude dilution, but it doesn't really change the argument.

Ex. Salary & retention package for founders & certain execs while common stock purchase price is drastically reduced. (just one example)

I did some time at a large financial institution making great money, but absolutely hated how empty it all felt. Nothing got done, nothing changed, nobody listened to me.

I work at a much smaller company now, and almost everything I do on a daily basis has a measurable impact. I can literally watch the things me and my team do increase the bottom line. I derive value from this myself, as it allows me to grow my team, hire new employees, give people responsibility of their own, etc.

5MM means you're flying business/first with your family anytime/anywhere. You may have a pied a terre somewhere.

10MM means you're angel investing, vacationing, and not generally "working" anymore.

15M++ means you bank with The Private Bank of Wells Fargo, have a ridiculous line of credit // no checking account, multiple properties, trust, etc.

Without actually knowing you, I can't say what type of person you are. But I can say the type of people I've met who had similar viewpoints were very arrogant and rarely recognized the great contributions of their employees, and often took personal credit for directions or products created by others (often when they were incredibly dismissive of those ideas before a breakout success). I would ask you to re-examine your view of your employees, but if you are an example of the type I'm talking about, it most likely wouldn't do any good. Your ego will not allow you to actually recognize any contribution as anything but your own hard work. You blaming your apparent bad hiring decision on lack of talent pool rather than your own ability to seek out the best does not paint a favorable portrait.

The shit your employees have to deal with working for you just might be a magnitude order worse than what you are going through as their boss.

That's what I think solely based on your post.

Employers do take all the company's risk, however my boss (small construction company) gets to walk away with millions in savings with no personal liability. I get unemployment benefits. He gets to retire to a million dollar house, I risk losing mine.

You need to dislodge your head from your ass if you think you're the only person taking risk.

You need to realize that people are these things called humanbeings they have their own lives, their own motivations, problems and stresses. A great manager does this thing called managing where they use their knowledge of their employees to keep them motivated, something you quite clearly are not doing.

You employees sound unmotivated because you've got the attitude your company is already going to fail. FYI people can tell when a company is circling the drain and will half arse it and ride it out until the first paycheques bounce.

But the problem with your reasoning is that, in reality, growing a successful company is a team sport. No matter how brilliant you are, you alone are no match for a high-performing team. Or even a medium-performing team.

The real issue is not what you deserve should the company "turn profitable." It is that you are extremely unlikely to become successful until you figure out how to build a great team. Which is hard, by the way.

My recommendation is that, if you have established product-market fit and are now in execution/scale mode, you need to either step up as CEO and make learning how to build and manage a team to achieve real results your #1 responsibility. Or if that's not your thing, you need to accept your strengths and weaknesses and find someone else who can play that role.

If you read the article, the people in it generally liked and respected each other. That is key to making a healthy workplace. Without it you don't get nearly the output you might otherwise. My experience so far has been that when there is a lot of 'crap' that isn't getting picked up by anybody I have found issues with ownership (nobody feels like they own the results) and communication challenges.

The thing about the startup lottery is that in the small chance your startup wins it, that doesn't mean you'll also win.

Founder did take the whole company on a tropical vacation which was unexpected and even paid partially for spouses.

Go be generous with your own money, dude, and quit trying to be generous with other people's.

What really needs to happen is for new ways to organize startups to distribute the risks and responsibilities better, so that it's not up to the goodness of the founder's heart to ensure a good outcome for the employees.

Of course, this implies that the pie is being made bigger, the risks and responsibilities being spread out are actually building more value in the company so as to generate a bigger exit. So far though founder-level discipline and risk-taking is rare enough in one individual that this is the situation we have to deal with.

Not sure that "everyone talks about" it (though that applies even more so for carrentals.com, IMO). Maybe they meant "everyone in NYC talks about it".

That said, Invite Media was acquired by Google for $81MM a couple years back.

After all there is no obligation on his part to ever do another start-up, there is no obligation on those rewarded to join in the future and the incidence of 'repeat teams' is low enough that I don't think it is a factor at all.

It's being both.

But good signalling involves some additional factors. Signalling is usually used when you want to say something about yourself, but it's something that people would want to say about themselves whether it was true or not, so you have to say it in a way that is difficult or impossible to fake. A good signal is one that is highly visible (in the context where it matters; clothes are good for in-person signaling, profiles or photos are good for online signaling), and either cannot be sent without having the quality they're supposed to signify (you can't afford expensive things to show off if you don't have money), or are much easier to send if you have that quality than if you don't (it's easier to get a high StackOverflow score if you're good at programming and communicating than if you're not).

If you're giving employees extra stock to signal loyalty and trustworthiness, it's "cheaper" to do that if you actually value being loyal and trustworthy (rather than just wanting others to think that of you), because then you get value from being the sort of person you want to be and being thought well of by others. At least, that's the theory; you could just want other people to think you're a loyal person really, really badly.