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For Airbnb employees, dream turns into disillusionment

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Re: For Airbnb employees, dream turns into disillusionment

#41

Earlier quoted context omitted.

In addition to that, the founders are signaling their own long-term lack of confidence by selling their shares when no one else is allowed to do so. Employees are correct to pressure their employers to IPO or GTFO, especially considering that many of these companies are on a trajectory where they're worth less over time (e.g. the collapsing valuations of Uber, Lyft, Slack, "We", etc).

True in the case of wework yes but in the case of Airbnb the founders seem to have collectively cashed out only a few tens of million, which just sounds like they cashed out just enough to buy themselves nice cars or something

$7M apiece would buy you quite a nice car.

Re: For Airbnb employees, dream turns into disillusionment

#42
post #20

Hard to feel sorry for anyone there since it's extremely unlikely that Airbnb is going to leave hanging anyone with expiring options (i.e. the oldest and probably most valuable employees), and those people are almost all bound to make many, many millions of dollars. Not sure what the deal is with Chesky's hesitation to going public, but Airbnb is by all accounts a wildly successful company and folks are going to "get…

> Airbnb is by all accounts a wildly successful company I remember 5 years ago when I turned down a lucrative offer from Uber because I just didn't believe in the company. People told me I was crazy, that Uber was the future of transportation, and how could I not understand how stupid I was? I just looked the fundamentals and said it will never make money. AirBnB and Uber are very different companies, the most notabl…

Uber doesn't need to make money for you to make money from Uber stock.

Re: For Airbnb employees, dream turns into disillusionment

#43

Earlier quoted context omitted.

In addition to that, the founders are signaling their own long-term lack of confidence by selling their shares when no one else is allowed to do so. Employees are correct to pressure their employers to IPO or GTFO, especially considering that many of these companies are on a trajectory where they're worth less over time (e.g. the collapsing valuations of Uber, Lyft, Slack, "We", etc).

True in the case of wework yes but in the case of Airbnb the founders seem to have collectively cashed out only a few tens of million, which just sounds like they cashed out just enough to buy themselves nice cars or something

[deleted]

Re: For Airbnb employees, dream turns into disillusionment

#44

Earlier quoted context omitted.

True in the case of wework yes but in the case of Airbnb the founders seem to have collectively cashed out only a few tens of million, which just sounds like they cashed out just enough to buy themselves nice cars or something

Probably homes and enough to guarantee a comfy lifestyle if things went sideways.

If the founders are hedging their bets and asking (or requiring) others not to, it's a bad sign.

Re: For Airbnb employees, dream turns into disillusionment

#45

Earlier quoted context omitted.

> Airbnb is by all accounts a wildly successful company I remember 5 years ago when I turned down a lucrative offer from Uber because I just didn't believe in the company. People told me I was crazy, that Uber was the future of transportation, and how could I not understand how stupid I was? I just looked the fundamentals and said it will never make money. AirBnB and Uber are very different companies, the most notabl…

Uber doesn't need to make money for you to make money from Uber stock.

[deleted]

Re: For Airbnb employees, dream turns into disillusionment

#46
post #20

Hard to feel sorry for anyone there since it's extremely unlikely that Airbnb is going to leave hanging anyone with expiring options (i.e. the oldest and probably most valuable employees), and those people are almost all bound to make many, many millions of dollars. Not sure what the deal is with Chesky's hesitation to going public, but Airbnb is by all accounts a wildly successful company and folks are going to "get…

Airbnb employees gonna make so much. This is gonna be worth $50 billion easily

Re: For Airbnb employees, dream turns into disillusionment

#47
post #22

I spent most of my 20s (7+ years) at a startup that is currently a “unicorn”, and consequently have an ok amount of shares locked up in the same situation. As the company’s valuation grew higher and higher the equity grants became significant lower. It was balanced out by my pay becoming more and more competitive vs other large companies. But eventuality I decided ~80% was as fully vested as I’ll ever be — Not to men…

don't you owe taxes on the stock appreciation?

That’s the first question I had - is that not how it works?

Re: For Airbnb employees, dream turns into disillusionment

#48
post #20

Hard to feel sorry for anyone there since it's extremely unlikely that Airbnb is going to leave hanging anyone with expiring options (i.e. the oldest and probably most valuable employees), and those people are almost all bound to make many, many millions of dollars. Not sure what the deal is with Chesky's hesitation to going public, but Airbnb is by all accounts a wildly successful company and folks are going to "get…

> Airbnb is by all accounts a wildly successful company I remember 5 years ago when I turned down a lucrative offer from Uber because I just didn't believe in the company. People told me I was crazy, that Uber was the future of transportation, and how could I not understand how stupid I was? I just looked the fundamentals and said it will never make money. AirBnB and Uber are very different companies, the most notabl…

Great analysis. Thanks for that. I admit I'm totally just an armchair observer here.

There are the market fundamentals, and there's the reality of irrational exuberance and whatever is likely to happen in the market regardless. So I still think they'll IPO at many tens of billions and mint as many millionaires as Facebook before any potential market realities set in.

Re: For Airbnb employees, dream turns into disillusionment

#49
post #24

I spent most of my 20s (7+ years) at a startup that is currently a “unicorn”, and consequently have an ok amount of shares locked up in the same situation. As the company’s valuation grew higher and higher the equity grants became significant lower. It was balanced out by my pay becoming more and more competitive vs other large companies. But eventuality I decided ~80% was as fully vested as I’ll ever be — Not to men…

"and because I joined so early my options were cheap enough to exercise over time" --> So you were exercising regularly while the company still wasn't worth much? That's a best-case scenario. The problem comes when early employees have a low strike price but don't exercise until the valuation is high, either because of vesting or just not getting around to it. Anyone with, e.g. 50 cent Airbnb options is looking at a…

Yes, I exercised regularly so my tax bill was manageable.

The company's trajectory looked more like a hockey stick, so my taxes were negligible until later years — and by then my original grants were exercised, leaving only my relatively expensive refreshers with a lower delta to fair market value

Re: For Airbnb employees, dream turns into disillusionment

#50
post #24

Earlier quoted context omitted.

"and because I joined so early my options were cheap enough to exercise over time" --> So you were exercising regularly while the company still wasn't worth much? That's a best-case scenario. The problem comes when early employees have a low strike price but don't exercise until the valuation is high, either because of vesting or just not getting around to it. Anyone with, e.g. 50 cent Airbnb options is looking at a…

A friend was early at Square and left options on the table when he left, because the tax bill shocked him.

Yep. That's the conundrum. If the company is doing so obviously well that the shares are likely to be worth something in the future, then they are almost certainly already valued high and have a huge potential tax hit. In hindsight, most hugely successful starts were still a big gamble in their early days when the share price was low and it wasn't the smartest thing to throw thousands, tens of thousands, or even more of your own cash at them.
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