understood - and glad to be discussing this. From the lack of other responses, it seems to be a niche interest topic :) Sorry for the length - please don't feel you have to respond to every aspect of the text below, I'm just trying to answer some of the questions you pose.

To answer your FreedomFirm vs rest: the primary goal I would have is to deliver all of the compensation of Silicon, Inc, in different packaging (ex: forgivable loans instead of salary, equity in the group, etc) but with better chance that the firm would succeed in the longer run and that the equity would be worth something one day. Plus, on the margin, a bunch of more negotiable items that are essentially impossible in ordinary employment relations:

- More moonlighting options in exchange for rougher RIF circumstances. Maybe instead of a RIF, the parent company stops funding one of the subsidiaries for a while but doesn't seek to shut it down or take away its license to certain IP. (more details below)

- More control in being able to market that subsidiary's IP or services to others (building businesses within businesses), within the bounds of the overall group's objectives/sensitivities. (say, maybe NetflixFreedomFirm would have a subsidiary that marketed its infra services, rather than give them all away as OSS for cachet or hiring lead-gen)

- More cash, say, in exchange for getting one's own health insurance on market terms rather than have the "company benefits" package - but with the option to get more equity instead.

- Less onerous "HR training" requirements in exchange for being directly responsible for one's corner of the enterprise etc. Groups could share materials about how to comply reasonably but not seek to have the total uniformity of current workplaces.

- Opportunities to invest more capital or buy-in, subject to qualifications for accredited investors and the like.

The key goal is reducing the drag on getting from startup to default-alive - the vast majority of businesses fail, so whatever one can do in the early stages to get them to default-alive, is probably worth it unless it gets too egregious (contract law being the more rough-and-tumble boundary). Existing labor laws try to some of this but they have poor proxies for default-alive like @wmf's example about of companies avoiding exceeding 50 employees. Perhaps once a company feels like it's at "default-alive" levels, it starts to roll things up into a more standard structure.

My belief is that this structure would appeal to:

(a) founders+employees who believe that with less intervention they can generate more value and who are frustrated with the tradeoffs of current labor arrangements - but who are willing to do some more private negotiating (ex moonlighting, side business, etc).

(b) former employees who are entrepreneurial, have enough knowledge to negotiate with founders/business partners (and value that aspect of work), and have appetite for more risk but without going all the way to starting their own fully stand-alone business.

(c) former employees who are interested in being/becoming independent actors - maybe building indy businesses in parallel or down the road, freelancing/consulting, etc.

Just to expand on an example I touched on previously: say the groupco co-founds a JV with a small set of engineers instead of hiring them directly. Maybe the engineers are the team who are going to build a new part of the groupco's product or will provide a broad service to the groupco (dev tools, say). When they form the newco with the engineers as founders, perhaps the groupco contributes some cash, some shares in the groupco, and some IP licenses to the groupco's existing systems; the engineers bring expertise. Over time, the engineers get more of the groupco shares as they deliver value. But then, groupco falls on bad times and would have laid off the newco team if they were traditionally employed. Instead, maybe they negotiate that newco can keep going, but doesn't get fresh cash from the groupco for some time. But - the shares in groupco that have been earned still belong and are apportioned to the founding team. newco engineers are a functioning team and can do projects for others to bring in cash, but groupco retains (say, limited-time) option to re-integrate them in exchange for granting them license to some of the base IP that they've been using to build some of the lowest layers of their dev tools. In time, groupco is able to re-integrate the team; maybe they've created independent value in that time that is acquired or negotiated over.

I hear your point that this path can create structures in which more sophisticated people could potentially take advantage of the less sophisticated. That's probably not easily fixable; similar to what happens if you get yourself into certain kinds of crypto or multilevel marketing. It could probably be mitigated to a degree with standardization, if the overall approach proves useful.

The flip side is: we don't really know at this point how much cost the current employment system imposes and how valuable the benefits it affords truly are, because we have no real counter-factual. If we gave looser structures an opportunity to develop, we might be surprised at how much real drag we're imposing at the early stages. FWIW, other countries do this regionally - they'll setup a "special economic" zone where the rules for commerce or business are just different, if you're operating in that area. Perhaps that would be one way of implementing something like this more narrowly.

PS: BTW (I am not a lawyer), but I do believe that even if you tried to pay everyone with Ethereum smart contracts, you might get drag-netted into de facto employment relationships. I think that's sort of what's being adjudicated with the Uber lawsuits in California and in other places.