Stories of equity working out well are rare in these comments. I think in part this is because contentment is silent, so I'll share a bit. I joined a private company with over $100M in revenue about 3 months before IPO. They couldn't say they were in the process when I took the job, but it was hinted at strongly. I got an options grant with normal 4 year vest that amounted to an actual face value of about $50k. Being successful, I imagined they could be worth $100k, or a $25k/year bonus on top of my salary. All of my actual negotiation was of the salary component, and I was very happy with the outcome.

The company went public, and the following year there were a couple events -- a nice earnings beat, some positive news, etc -- that pushed the stock up. Around that time I hit my 1 year cliff so I had 25% of my grant vested. I sold every vested share and used that as a down payment on a house in the bay area. I had a very large tax bill the following year that I paid by selling a bit more equity. But, I have a house that has appreciated since I purchased it, not to mention a nice place to live.

In year 2 I started receiving add'l RSU grants, and I usually sell them as they vest. Here's the test: If they gave you a cash bonus would you BUY stock? If not, sell it.

In the end, my initial option grant will end up worth $300-400k, adding almost an entire extra salary to our household income.

We've been fortunate, have given back a lot to charity and especially to family. Oh, and I've truly enjoyed working there.

What I've learned is that there is a probability curve. I chose an offer that had a high liklihood of buying me a down payment on a house but zero chance of buying me a whole house. In the end, this is a pattern I would repeat and I think if you can do go work for Uber, Pinterest, Airbnb, etc, where an IPO is very likely, go do it.