I completely agree. I recommend selling along the way. You may lose some upside, but you definitely lose some downside.

Unfortunately, WeWork employees aren’t given that choice. They are getting fired with underwater options while Adam makes billions. I wonder how he can rationalize this to himself.

Why would he need to rationalize this to himself? He just made over a billion dollars.

He can, and will, continue to fail upwards.

With his luck he should jump in the 2020 primaries.

Just like Nelson bigetti

I can think of a Billion reasons for him to rationalize this !!!

I can think of many counter examples too. Say, Netflix, Arista Networks, Google, Facebooks, and etc. I guess the key is to pick a good company instead of avoiding options. And of course, leave a company immediately if it shows fundamentally bad signs.

The key at this point is to pick a good public company (except Beyond Meat that is highly overvalued compared to half year ago). In that case it doesn't matter that much if you're getting options or cash.

I don't see any reason for working for overvalued options at a not-early-stage private company. Also I view being an early stage employee too risky to worth it.

Meh I regret selling any GOOG in the low $200s

It was still the right move. As every poker player knows, just because you lost doesn't mean you played the hand wrong.

It wasn't necessarily the right move. He/she likely had asymmetric information about where Google was going and how likely it was to continue succeeding.

If they couldn't sufficiently exploit that, then that's on them (assuming they had access to all the relevant metrics).

It's great to diversify, but blindly selling isn't some sort of virtue to optimize for...

depend, as I wrote above. If I give you 2 options.

1) $300K in GOOG 2) $300K in cash

if you dont believe that using all of the $300K in cash to buy GOOG immediately is the smart move, yes, you should be blindly diversifying.

I think we're largely in agreement.

If you can't leverage the asymmetric information about your company to make a competent buy/hold/sell decision then yes by all means diversify it all.

I just want to make sure the point about asymmetric information is clear though. And it's more relevant in private companies than public ones.

If you're not willing to buy and hold private company equity even after having access to asymmetric information about the firm, then you should consider leaving the company entirely. If you don't then that defeats the entire purpose of taking a chance on a private company and being compensated in equity which can't be acquired through traditional means. You're accepting the equity presumably because you think it's worth a lot more based on the asymmetric information and market opportunity.

You shouldn’t. You need to sell some of the options of the company you work for to diversify. If you think you are smart enough to know the future of stock prices than you should trade stock for a living.

I remember at the start of my career selling portions of my GOOG grants like all the personal finance guides told me to do, and how shocked I was that when my coworkers would tell me they held onto all of theirs...

OTOH, it just as easily could've gone the other way, I suppose? Google truly is sui generis, and it's hard to fault me for not knowing that at 21

having $300K in GOOG and not selling it, is no different than having $300K in cash and using it all to buy GOOG.

If you wouldn't do the latter, you shouldn't do the former (but yes, if you would have invested all your cash into google, more power to you to keep all your google stock as google stock)

Same. I have enough financial exposure to the tech industry through my work that I don't want my investments to be correlated with that.