[fizx]

It's actually easier to "invest" as an employee than as a VC. VC's have to wait until the next round, and have to compete with other VCs.

As a potential employee, you can see a company wildly succeeding (twitter in 2009, uber in 2012-13, slack, github, etc) and yet they will have <200 employees and their stock options will be granted at a 409a valuation around ~100million. Its a pretty reasonable bet at that point.

You will hit some underperformers/duds (coinbase? bird?), but you will have worthwhile stock options a good chunk of the time.

[tschwimmer]

If this is true why not just be a VC? You could pick all these unicorns at a great value. Even if you don’t put any of your own money in the fund you will make vastly more on the fund fees than you would have as even CTO.

I think you’ll find that consistently picking unicorns is essentially impossible across a long time frame.

[fizx]

If any VC could have bought $TWTR at a $280MM cap in 2010 they would have. Only employees got that deal. Twitter was already a unicorn, but the internal paperwork hadn't caught up yet.

It's arbitrage, not clairvoyance.