It is inevitable. The reality is that this is how a lot of regulation starts. It doesn't always come from an anticompetitive place. We just forget that we actually asked for the regulation. Once we have, it's nice to always be able to blame the government or some regulator when something goes wrong. And then someone else can come in and "disrupt" the market by using a loophole of pretending like the regulation doesn't apply to them, when it's clearly intended to.
Maybe the fact that cab drivers need a licence and are thus screened more thoroughly?
Case in point - when an Uber driver raped a woman in Delhi, this is exactly what the Delhi government did.
Chronic problems would be over charging - put it this way, the day before taxis were forced to charge a certain amount each mile, all taxis would have been free to charge different amounts as uber and lyft can.
We do ask for regulation - and always in response to symptoms. Regulation is not pre planned rational thought ...
Now it's legal because it flies under the banner of "rider sharing". But we all know that there is really no sharing to be had. It's just a for hire service. The regulation will return, eventually.
Like Zenefits, the government regulation that Lyft, Uber, and Airbnb are skirting has one important consequence: It protects the rest of us who are not their customers from them. If a Yellow Cab driver does something dumb, malicious, or against the rules, I can complain to the city regulatory authority and that agency can take action. If it fails to take action, I can pressure my elected leaders to correct that stance. If it takes action in an open way that is transparent to the populace and finds that I am not correct in my complaint, so be it. I need not be a customer of Yellow Cab to complain about the actions of one of its drivers.
Replacing public rules enforcement with "reputation systems" is completely useless if I never enter into a business arrangement with those companies. As it stands, the only way I can complain about any of them--especially with Zenefits actively working to hide its bypass activities from the relevant authorities--is to be a customer and poorly rank some allegedly-independent-contractor. Or I can use Twitter and complain publicly but get drowned out by the noise.
That's no substitute, in my opinion.
For the rest, as you state, they have been largely clear about their opposition to perceived out-of-date regulation and have worked tirelessly across the country and world to have new rules or exemptions or trials put in place.
Being disruptive isn't the same thing as breaking the law with willful abandon.
Here's a good take: https://stratechery.com/2016/zenefits-and-regulation/
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.
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.
Zenefits sells to HR departments whose raison d'être is to make sure the company complies with its duty of care to employees, including observing all the relevant regulations. The idea one of their partners might have been using inadequately trained and unlicensed insurance brokers that didn't really know what they were doing to sell their employees expensive health insurance plans is kryptonite for that partnership.
(and I say this as someone who always ran the blindingly obvious "how not to take a bribe or sexually harass your colleagues" compulsory videos in the background whilst getting on with more productive work)
Lyft and Uber skirt similar kinds of seemingly useless regulation but they're completely up front about it. They don't pretend that their drivers are licensed or get any benefit from having licensed drivers in any way. They're simply offering a different product than what taxis offer - getting a ride with a random unlicensed stranger.
Lyft, Uber, and Airbnb are betting that reputation systems (ratings, reviews, etc.) will provide assurance for consumers just as well if not better than government regulation. So far the market is showing they just might be right.
Zenefits seems to have been driven by a similar cultural distaste for onerous and probably out-dated regulation - who can blame them? But instead of letting the market decide how valuable that regulation actually is they simply cut corners when they hoped no one would find out.
That deceptiveness, more so than the regulation dodging itself, is ultimately really bad for a B2B business.