[jjav]

> Imo early exercise doesn’t make a ton of sense when the company no longer qualifies for qsbs

I strongly disagree, early exercise is always optimal if the cost makes sense to you.

The primary reason it is so valuable is so that you don't lose everything if you have to change jobs for whatever reason before a liquidity event. If you join a startup and don't early exercise, now you are going to have to work there for however long it takes for liquidity, which could be many many years. Maybe your life changes and you have to change jobs, but you're trapped, or lose everything you worked for.

Always early exercise! If the startup doesn't allow it, find a different startup.

Edit: I should add that by not early exercising you can still lose a lot even if there is a liquidity event while you're still there! I lost a staggering amount of money on my first startup due to not early exercising even though it went through an IPO while I was there. But later I left (lured to another startup) so I had to excercise (same day sell) all the option in the typical 90 day window after quitting. Had I early exercised years before when I joined, I could've held those shares for 15x returns.

[dilyevsky]

See my point about long exercise window - 5-10y is not uncommon now. I’d rather have that even though it converts to PSOs than gamble ~50k + amt on early exercise. Unless you’re super early ofc which changes the math

[jjav]

> 5-10y is not uncommon now

Is it?

I'd be curious on survey data on that if something is available.

Personally I've never encountered a startup that had anything other than the standard 90 day after you quit exercise window. I know these long exercise windows exist but as far as I knew they are pretty rare.

> gamble ~50k

That's a huge number though, I'd never gamble that much either.

I'm talking about very early in the startup. If the strike price is above a few pennies, it's too late (although of course depends on the number of options and your personal budget).

[dilyevsky]

Anecdotally, i've received more offers in the last ~5 years with extended window. I think it's just natural evolution due to increased competition for talent with high-paying public companies. Here's an incomplete list btw[0]. There are usually some strings attached - e.g additional cliff to qualify (like 2-3 years with the company) and you need to sign a separation agreement when leaving, etc

> That's a huge number though, I'd never gamble that much either.

I've been offered early exercise of 25k options with a $2 strike price. Series B startup. So yeah...

[0] - https://github.com/holman/extended-exercise-windows

[jjav]

> https://github.com/holman/extended-exercise-windows

This is a nice list, thanks!

No idea how complete that is, but it lists roughly ~160 companies. Which is nice, but according to [1] there are about 71K startups in the US. (Of course both of these counts might be wrong but let's go with these numbers.)

So about 0.2% of startups have extended exercise windows. Not a lot ;-(

[1] https://github.com/holman/extended-exercise-windows