Ask HN: Employees who exersised stock options: how did it go?

I'm curious to hear about people who excersised their stock options at a startup and there was a liquidity event (i.e. acquisition, merger, IPO). How good was the RoI? Did you lose money?

Piggy backing here, I exercised options 2 years ago when quitting my job. The company had a down round and I don't believe they have much of a future so I'd like to sell my stock back to the company, the stock at least being worth more now than the $30k I paid on exercise. Has anyone sold stock back to their company? What was the process like?

The problem is that you never know when a liquidity event will happen, and not all outcomes involve you at least breaking even.

The company I have my exercised options with hasn’t gotten acquired, hasn’t gone public, it just hobbles along failing to make a profit year after year receiving round after round of funding by investors who just hope to turn the company viable.

I was only able to buy a few hundred bucks of shares, and I considered the proposition to be like a night out at the casino. Plus, I get to satisfy a little post-employment curiosity by getting to read investor information like balance sheets and income statements.

In my opinion, equity compensation and/or stock options suck. They probably only make sense for people working for Microsoft, Apple, Google, Amazon, and the like. I don’t want thousands of dollars in my investments riding on the success of one single company, especially is that company doesn’t have a street named after itself.

Joined a company 2.5 years pre-IPO, and made about ~200k pre-tax (but I waited until after the IPO to exercise as I didn't want the risk) at lock-up, with another ~400k still vesting.

Worked at another company that supposedly on the IPO track. Didn't buy my shares, and they ended up being acquired in a fire sale and gave 1 penny per share to those that did exercise. Company had gone through three rounds of layoffs ("normal trimming down before you IPO" lol), and I still had friends that exercised their shares.

For me, I'm willing to take the tax hit by waiting to exercise since I've seen so many companies fail.

Didn't exercise my options before acquisition, didn't need to. Was paid the same. (Not a life changing amount of money; roughly what I would have gotten by staying at FAANG for the same amount of time. I still consider it a good outcome.)

The only difference from not exercising was I skipped a bunch of paperwork both at exercise and at acquisition time. On the other hand, the paperwork might have been interesting to learn more about how startup acquisitions work, and might have contained numbers that I would have liked to see. So in hindsight, I wish I had exercised at least a few of my options just for the sake of participating in the acquisition process as a shareholder.

I don't know if my experience is representative, though. I can certainly imagine that some exits might treat option holders differently than shareholders. I don't know the legality of that.