Why? An honest question. I generally do not care how many people work at the company. If someone organizes and builds something useful, something profitable or something beautiful why does it matter (much) whether he built it alone or hired 20 people to do it.

For example, I found that two of my favorite software products were built by a single person (I assumed medium-sized team for each). That, if anything, made me appreciate them more. My 2c.

When I hear “self-employed” I imagine contract gigs like websites.

When I hear “one man startup” I imagine a monthly SaaS product.

Seems like a reasonable distinction to me.

Digital nomad? OPC? Forward deployed engineer? Generalist? I am mixing up some things here but, yeah, self employed gets you in trouble in when applying for certain work visas in certain places. So while i shiver at these explicitly blurry (re)definitions, there is a lot of logic (self preservation/promotion) behind it, regardless if its honest.

Why? if he's selling his labor, then it's self employed. Selling a product, that's a proper business.

Still better than the linkedin's special: "CEO, CTO, CFO @mybullshitstartup.ai"

Isn't this the entrepreneur-or-freelancer divide? Is the thing you're working on making you money while you sleep (entrepreneur, "startup" is appropriate) or do you only get paid when you work (freelancer, "self-employed" is appropriate).

Not saying this distinction is useful, but at least it's a common way of talking about the various forms of "being your own boss".

The funny thing about this is that it's actually easier to set up and manage a startup without any employees (and worry about how to pay yourself down the line, if and when there's actually enough money in the bank) than it is to set up a self-employment operation.

The personality disorders behind these decisions would never settle for that.