That's an excellent point. And Ben Thompson is super insightful as usual (I'm a huge fan of his).

I certainly do think the value prop to consumers for Zenefits' rule breaking was not very clear. However, I'd argue that lack of clarity stems from the fact that they were breaking rules in small and kind of sneaky ways, and not in a clear way baked into the core of the product.

If they were totally unappologetic about bending laws from the beginning - ie their pitch was more like "Zenefits lets anyone sell insurance and provide other services to small businesses, making these things more accessible and affordable" - then I think people would credit all benefit they get from Zenefits to its rule bending, and put up with a lot more of it.

Instead, Zenefits was kind of trying to have its cake and eat it too, which just pissed people off.

To be fair though, I suspect that creating an explicitly unlicensed insurance brokerage would be much, much harder to pull off than an explicitly unlicensed taxi service.

AirBnB might benefit the customer, but can negatively impact others in the area. For example, if someone is renting out an apartment in a secure building, just giving the keys to an arbitrary someone you're decreasing everybody else's security. Similarly for a house, if a house is being regularly rented by different people, it impacts the rest of the neighbourhood.

In my building, renting out with something like AirBnB is against their occupancy agreement. While I don't know everybody in my building, I certainly know everybody on my floor. I used to know everybody in the building, but a number of people have moved out and I haven't learnt all the new people yet. I'd be really pissed if I found out that someone was offering an AirBnB rental right next to me.