My experiences:<p>1. Had my own startup, I was CEO. At one point we had a good LOI-valuation, I was a paper-millionaire. In the end we failed to raise, failed and I didn't make any money. But at least I didn't invest/lose any of my own money, and exited without screwing anybody over. Only lost money on oppty-cost, ie. money that I could have made if I had a regular job.<p>2. Worked at a resonably successful startup for 3 yrs, started in 2012. When I left in I exercised 10,000 pieces of stock for $5,000. It's now 10 yrs after my start date, no liquidity in sight, company is not doing so great. Probably what those 10,000 pieces stock will be worth is 1 month of my current salary, so it's irrelevant now.<p>3. Worked at Facebook for 18 months (London, E5). Vested arond $100k of stock, payed ~55% taxes, sold stock right on vest date, made around $45k. If I would have kept it and sold at the highest point of the stock, it could have been ~$150k. Today it'd be worth around ~$75k (FB stock was cut in half in the last 6 months).<p>The upside of stocks: I do know people from Facebook who got early stock, and Facebook is the last job they'll have...<p>4. Worked at a delivery startup. At this point I was smart enough to ignore the stock and negotiate strong on the cash salary, so I made good risk-free money every month, but still vested a lot of stock. In the end the company failed, technically the stock was re-valued, so all my stock was worth something like $0.01. I did a great job managing my expectations, so I wasn't unhappy (I knew the CxOs are crooks and it's unlikely the company would be successful).<p>5. Current job at a non-tech BigCo doesn't have a stock component, just a high base salary, and no taxes (Dubai). This is the way.<p>6. The funniest stock story I have is from a job offer I didn't accept. This company gave me a reasonbly good offer with a stock component, where the stock contract had this specific language:<p>> ... shares issued under this Plan shall be "hypothetical" stock, which means that the Company gives the Employee the benefits of owning stocks in the Company without actually
giving the Employee stocks or shares certificates ...<p>The contract had 3-5 clauses in there which said that the CEO could essentially decide to void my stock at any time for any reason. I told the CTO that these are red flags, he told me he agrees, he had the same concerns, but blah. In the end the structure of the stock plan was one of the reasons I declined, it was a red flag for company culture.