[AYBABTME]

I've seen a lot of people lose a lot of money because they bought into the "value the equity at zero" mentality. It sure sounds great and edgy to be blasé and just take your pay, but if that was true, you'd be better off working at FAANG 99% of the time.

IMO if you work for a startup company, you should only do so because you believe in it, and if you believe in it, you should exercise your option as fast as you can, perhaps with an 83b election if you can afford it. Otherwise what's the point of taking a job at a startup with a lower TC and higher risk outlook than a FAANG job?

Hence, I think:

  - only join startups you strongly believe in, 
  - only join startups that offer good equity package, have raised good rounds, have healthy cap tables,
  - get as many options as you can, 
  - exercise them as fast as you can,
  - work hard to make it worth something,
  - leave if it doesn't work out.

That's kind of the whole point of joining a startup. You're joining a bet, where you've got a significant chance of influencing the outcome.

[Jensson]

> but if that was true, you'd be better off working at FAANG 99% of the time.

Pretty sure 99% of people actually would be better off working at FAANG, or at least the 99% number isn't far off. FAANG promote quickly so salaries will climb and you'll have millions in the bank by the time a start-up would go public, I doubt many start-ups beats that.

The main reason FAANG employees don't have those millions is that they consume them as they get them rather than invest it and then get all that money at once after 6 years.

[elwell]

Sorry if this is a dumb question, but why would you want to exercise your options as fast as you can?

[rfrey]

1. You pay tax on the difference between the current valuation and your strike price. So if you exercise before new valuation events you save tax dollars, potentially a lot of tax dollars.

2. If the company gets acquired there are several mechanisms founders and investors use to wipe out options holders. It is harder to wipe out common stock owners. If an acquisition event takes you by surprise you may not have time to exercise.

3. You may get laid off, decide to quit, or get fired, and have only a limited time (3 months, often) to exercise your options. That might be a bad time for you to spend the case, so you may want to do it now while you are in a better position to do so.

[elwell]

Regarding #1, won't you have to pay tax on the gains anyways, if you ever sell the stock?

[rfrey]

Sorry, I missed this when you posted it. Yes you're right, you certainly will pay tax. But you'll have the proceeds from the sale to pay it with. When you exercise options for (possibly non-liquid) shares, you have to find money to pay the tax elsewhere.

If you can exercise and immediately sell the shares, point 1 isn't relevant.

[AYBABTME]

Good point about (2), I think that's also overlooked.

[AYBABTME]

Lower tax bill, as you need to pay taxes on assumed gain when you exercise your options, based on the latest 409a valuation of each share. The lowest such valuation in a startup is usually early in its life, and during your tenure, the valuation should go up steadily (or something's horribly wrong with the company's business) and thus your cost to exercise increases over time.

Another reason is more practical: it's much easier to exercise your options when the tax bill is lower and you just got a job/while you're employed (i.e. you're more plush with money), than when you're quitting/been fired and have 90 days to figure out where to get money from. Basically, it's better to be in control of when you buy, than being forced to buy or lose out.

[nosefrog]

You pay less in taxes if the options are valued for less, which they usually are the earlier you exercise them.