Any stories of employees with equity successfully taking home over $1m? $500k?

Hindsight is 20/20. I thought I had missed the boat in 2007 when Facebook was valued at $500 million. "Clearly they couldn't go much higher than that!" I thought.

I have a friend who got an offer from a startup in 2011 w/ 0.15% equity. He didn't take the offer. The company was WhatsApp and his equity would have been worth $27 million.

Not sure why your getting voted down but once you've experienced the ups and downs of equity value it gets to be quite noisy. So the car I sold to used car dealer which I "paid" 1.6M for was replaced by another car I had bought using some stock money I got from a company that had acquired my startup, when I sold that car 5 years later the stock used to buy the car was worth a bit less than $400. Sometimes you win, sometimes you lose, but the reality was "Hey, I've got a car and no car payments." which at the time was relevant.

The message is very much that getting "rich" doesn't really matter if you're the founder or a later employee, and its pretty random with respect to "skill". If you happened to be at Sun in the 80's and you sold your stock in the late 90's you made a lot, if you kept it until Oracle bought the remains, you made much less. Same stock different value. (and yes I had a wee bit of stock left when Oracle bought them)

What I learned from that was that making money in the stock market was about targeting a gain and capturing it. So when Facebook went public I bought some at $18 and told my financial advisor to sell it if it ever hit $36 (which it did of course). So for that part of my portfolio I made a bit more than a 100% annual rate of return for that one stock. Its up to $81 today, at some point it will likely be worthless. But for me, it took some of my money and doubled it in less than a year. Good enough for me.

But the Ask HN post is about whether or not equity compensation is "worth it" and the answer in the Bay Area has always been "yes". How much, or how little, extra it is, varies but as long as you wait to exercise and make a profit (yes you pay a bigger tax burden but its always a positive amount of money) it is just "extra" money that you got in addition to your pay. It it worth to work for stock instead of pay? That is a much riskier deal and probably not if you can't afford to pay your own bills independently. And do you have to work at a "startup" to get a big boost out of equity value? Absolutely not.

I'm now on my third startup that has IPOed (Zendesk). I've been relatively lucky, but I also tend to eschew media and gaming companies; my perception of the risk of long-term failure is higher for those. I prefer to work for B2B and infrastructural companies that serve up-market customers and provide real technological value (i.e. can't be easily copied), and my choice has served me well thus far.

It also depends on what you mean by "getting rich." If you want to make say $500k-$5M, I think that by far your best bet is to join a company that is shortly pre-IPO or shortly post-IPO that is CLEARLY valuable. Where your equity will be worth something, barring disaster.

If you want to make $10M+, then joining an already-valuable company isn't going to do it unless you can become an executive. Founding a company might do it. If you want to make $100M+, then founding a company is probably the only way you can reasonably do it (unless you're competitive for a very small number of very high end executive slots).

What is interesting to me is that I find it kind of hard to imagine many results in which it's truly worthwhile, monetarily, to be an early employee at a start-up. You are much less likely to get wildly mega-rich, like a founder -- probably at least 10x less likely -- and you're much less likely to get a medium-rich than someone who joins already-successful companies.

I say this as someone who has been an early employee at several start-ups. And really enjoyed it. But it's hard to make a financial case for it.

Maybe the answer is just that being an early employee is financially non-optimal, but some people for a variety of reasons can't or don't want to be founders, and some people for a variety of reasons can't or don't want to get a job at an already-successful company.

Yes, this is also my story from the turn of the century. I still work in startups, but also I jump out of planes for fun. Money like the kind in this thread has nothing to do with my life choices anymore.