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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 paid" as they they say in sports.

If you want to read about people with legit gripes about expiring options and lack of liquidity in an under-performing company, google any story about Palantir from the last five years.



> 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 notable difference being that AirBnB actually makes money. That said, AirBnB has lots of issues to be worked out before I would consider them a "wildly successful company" in the sense that they are not doing remotely as well as they should be considering how many years their competition was paying regulatory taxes and they weren't. Based on anecdotal evidence, their dark patterns are making their users grow to hate them more every day (not a great sign before an IPO) and they're making weird moves in the hotel space - that industry they were supposed to replace instead of become. And now they have real competition from HomeAway and others and I just don't see a growth trajectory for them anymore - honestly I see them shrinking in a few years. The fact that it took them until 2017 to generate a profit in a space where they own nothing, rent nothing, and have no expensive infrastructure in an enormous market where they didn't pay competitive taxes (but managed to win a local election despite this clusterfuck https://slate.com/business/2015/11/airbnb-defeats-prop-f-in-...) is a fucking alarm bell. More cities across the world are starting to ban their service, and laws are being created to actually enforce this. I am certain if this comment gets seen by many people I will get replies telling me why AirBnB is healthy, and all is well, and I just don't understand - just like I did all those years ago with Uber.

I'm not convinced AirBnB is going to exist in 10 years (for many more reasons than I listed in the paragraph above). Maybe I'm wrong. But until AirBnB is a public company for ~6 months and we can see their financials, watch the stock price fluctuate, and see how many people jump ship the moment their equity vests...well it's just another unicorn story where the VCs are pumping up the price to dump the stock.


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.


Uber the company will probably never make money. But you would have likely made plenty post-IPO


Are the golden handcuffs even off yet? There's still months to go for the shares to fall...


If all you want to do is make money, you should enter finance instead of tech.


This entire post is about making money. If you’re positing that your post was just about how you turned down Uber because the company wasn’t profitable then your comment has no relevance to this thread.


My entire post is about considering whether or not companies are going to succeed and thinking about that before accepting a job. You shouldn't blindly assume unicorns will be successful or would even be considered positive steps in your career (despite the money I turned down I am still incredibly happy I never worked at Uber).


The OP is about stock options going worthless. Uber’s most definitely did not do that. Really not sure what you’re getting at.


Uber employees still can't sell their stock for nearly 2 months, and it's on a downward trajectory. I think many employees are going to be upset with their "reward" for joining the ubercorn when they realize their shares are not worth what they were told (this is very different from being told they're worthless, however).

You are right though that my original comment is a bit of a tangent, so I apologize if I wandered a bit too much.


All good. For what it’s worth I also turned down Uber about 5 years ago and am damn glad I did.


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


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




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