I think you raise a valid point overall, which is that a lot of VC money gets invested very quickly into businesses with unproven models. That, in and of itself, is a real problem. Ralph Lauren started his multibillion-dollar clothing empire as a door to door tie salesman. He built his business one store sale at a time. Why can't today's entrepreneurs in the clothing space start small and grow organically? Is a startup in the bra market really in need of tens of millions of dollars in order to hit necessary traction? Is rapid, overnight growth really the best way to build a clothing brand? All very reasonable inquiries.

That said -- and I say this as respectfully as possible -- you're applying 20/20 hindsight in many of your examples. Fact: many women in this country, perhaps even a majority, have bras that don't fit correctly. Fact: women's boobs are highly variable, and do not actually fit into the standard cup size / chest size system that we've been using for the last 50 years. (An algorithm may be an over-engineered way to approach this problem, but the current model is far from perfect). Fact: men's razors are ridiculously expensive, and the razor & blades model is ripe for disruption. Theory (perhaps more viable than you might think): curated boxes of goods may, indeed, drive lead-generation and discovery, opening up new markets for apparel and home furnishings businesses.

I don't think it's remotely fair to look at the present-day struggles of companies like Dollar Shave Club or Trunk Club and declare, ipso facto, that their business models are fundamentally unsound. Perhaps their business operations are unsound. Perhaps their business strategies are unsound. Perhaps even wildly so. But the addressable markets seem reasonable in both cases.

Finally, I think you're cherry picking some examples and using them to draw a larger condemnation of the whole system. If we're going to declare that the system is rotten, then we need to begin with a macro-level evaluation of the system.