This is the old, "Easier to ask for forgiveness than to ask for permission"

A lot of these companies have taken this approach. Break laws until someone finally notices AND does something about it. The runway to a slap on the wrist is often times more financially beneficial to companies - there is no incentive to stop if you run a billion dollar company and breaking the law gets you a $50M dollar fine you make back in a single month.

I thought SOX (Sarbanes–Oxley Act) was supposed to prevent a lot of this, but I guess companies just continue to find loopholes to exploit.

I think sometimes people need a visceral demonstration of what bad laws are actually preventing. Uber was a pareto improvement in my view: we are in a better world both for consumers & for low-income wages having ridesharing as a backstop.

On the other hand, I've come around to the view that sports betting is a net unqualified bad -- and I didn't necessarily feel that way before the Kalshi/PM explosion.

Uber and AirBnB were things we should have taken far more seriously.

That being said, they weren't effectively offering unregulated gambling on any difference of opinion. Gambling is a vice. We've made it a regulated vice, but it's very much still a vice. If you get rid of the "regulated" part, people, including those with the ability to present a case in front of a grand jury, are going to see you as a 1980s cosa nostra capo and act accordingly.

So your two examples of this supposed bad thing are two completely unambiguous goods for the world?

What behavior from Airbnb do you think compares in criminality to running an online bookie?