Do we have a term for this phenomenon yet? Airbnb is a great example. Uber is another. Regulatory loopholes are the way that these companies actually make money, but they call it "technology" and everyone kind of shrugs.
The regulation that came after has in my personal experience privatized airbnb and now it's hard to find a private renter, when I started using it that was the standard.
Nobody cares about small tech companies breaking the law for a few users.
Everyone cares about {insert bad outcome from mass regulatory avoidance}.
(Also, of the 3 airbnb founders, one has delusions of being the next Steve Jobs and turning it into an everything app (Chesky), another now works for DOGE (Gebbia), and the last is sucking up to Chinese government data requests (Blecharczyk)... so, yeah, not exactly the sort of folks that should be trusted with light regulation)
More examples include Uber to bypass taxi regulation, and generative AI to bypass copyright regulation (as well as consumer protection regulation in both cases as well as labor protections).
I am under no illusion that if a user of AI requests an image of Indiana Jones and uses it in their art, the rights holders will issue a takedown an would succeed. The AI company that owns the model that generated the model will however not face any consequences, and have therefor successfully have bypassed copyright protections.
Similarly, in unregulated free market capitalism, there would be no copyright to bypass.
I am not trying to argue that either of these area panaceas but I feel like we are often in denial about how much collectivism is involved in the things we don't like about capitalism.
Yes ofc, on one specific aspect of regulation - the total qty of cars allowed - they did an end-run. But regulating the total # of taxis was always just a way of trying to limit land consumption by cars, rendered ineffective by only applying to cars used as taxis instead of all cars, all vehicles. So yeah, they benefited from a titch less regulation, but land in cities is so valuable that to give it away for free dwarfs the value gained from skirting any other regulation, so IMO it's still largely a collective non-market endeavour, just organized for the benefit of ppl in cars, rather than the public at large.