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Re:For Airbnb employees, dream turns into disillusionment by asdfasgasdgasdg on Sunday September 22, 2019 @12:09PM (#21042042)
This is the number one reason I would not want to work for a startup. Even in the unlikely event that the company is successful, there's better than even odds that you won't be able to trade on that success for years to come. That means you're effectively locked in at the company until it suits the executives to let you out. No thanks. I'd rather have a higher salary and immediately tradable equity grants with a company that's already public.
Re:For Airbnb employees, dream turns into disillusionment by human20190310 on Sunday September 22, 2019 @12:47PM (#21042327)
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).

Re:For Airbnb employees, dream turns into disillusionment by ramraj07 on Sunday September 22, 2019 @01:02PM (#21042418)
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
Re:For Airbnb employees, dream turns into disillusionment by ummonk on Sunday September 22, 2019 @04:03PM (#21043584)
Employees would like to cash out enough to get downpayments on pricey Bay Area homes too, but screw them amirite?
Re:For Airbnb employees, dream turns into disillusionment by freyr on Sunday September 22, 2019 @01:11PM (#21042478)
$7M apiece would buy you quite a nice car.
Re:For Airbnb employees, dream turns into disillusionment by almost_usual on Sunday September 22, 2019 @01:05PM (#21042435)
Probably homes and enough to guarantee a comfy lifestyle if things went sideways.
Re:For Airbnb employees, dream turns into disillusionment by human20190310 on Sunday September 22, 2019 @01:14PM (#21042502)
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 by kjksf on Sunday September 22, 2019 @01:40PM (#21042675)
If I had 500 million in paper valuation and could turn 10 million into real dollars, I would do it and so would you. I would have to be an idiot not to do it.

Not being able to sell shares in private companies is a standard practice. There are good reasons for that. The reason public market is heavily regulated is to prevent fraud.

The fact that large shareholders can sell shares in companies is also a standard practice. You might not like it but it's not capricious either. The founders created the company, the investors put money in it. They get better kind of shares than an employee because their contribution is materially different.

Re:For Airbnb employees, dream turns into disillusionment by human20190310 on Sunday September 22, 2019 @04:29PM (#21043729)
> I would do it and so would you. I would have to be an idiot not to do it.

It's smart. That doesn't mean it shouldn't be criticized. It's forcing employees and others to take risks (specifically an equity position that cannot be partially sold to hedge against company failure) that the founders are not willing to take themselves.

Re:For Airbnb employees, dream turns into disillusionment by jmastrangelo on Sunday September 22, 2019 @01:35PM (#21042643)
Often yes but in this case I don't think so. These guys are worth _billions_. It would be financially imprudent to not cash out a little bit purely for diversification and buying a nice house or two.

If you'rea a founder in a world where you can fundraise enormous sums from private markets, why deal with the headache of going public?

Re:For Airbnb employees, dream turns into disillusionment by n7_goat on Monday September 23, 2019 @03:48AM (#21046745)
Even worse if you are acquired by another private company your shares are completely illiquid.