[sulam]

Almost certainly a mistake. The only way I can imagine is if the company was pulling a fast one on employee taxes. If you’re a 1099 contractor, you pay your own taxes and are not eligible for ISOs.

Did you get W-2s with withholding at this place?

[hamburglar]

Yes. I wonder how this would have turned out differently if I'd had ISOs. I exercised them all and paid taxes on the difference between the strike price and the 409(a) valuation, treated as income, and the company did me a favor by arranging for me to sell a small number of shares to one of their investors at much higher than the 409(a) valuation to cover my tax bill (the agreed-upon price was close to, but not quite, what they were planning to raise their next round at). I thought this was a pretty classy way to solve the liquidity problem for an employee that owed taxes, and I would like to see something like this become standard.

[sulam]

Sounds like you got pretty much exactly what you would have in an IPO (presumably at a lower valuation of course) if you'd decided you were bullish on growth and didn't want to diversify.

The main thing you missed out on was the ability to 83(b) exercise. If you don't know, that is something you can do in the first 90 days following the stock grant, where you write a check to the company (usually some administrator the company designates) that exercises at the same value as what the grant was written at. That means you 1) don't have any capital gains to worry about, which with AMT can be a big deal, similar to NSO treatment and 2) start the long term capital gains clock, so you are potentially taxed at a lower rate than ordinary income.

Since it sounds like this startup went out of business (?) I think you were essentially treated as well as possible.

[hamburglar]

No, it's still going and quite profitable. They never even took their next round, so dilution has been minimal. Edit: still private, though, so no liquidity on what I own. Patience.