Me and my cofounder fantasized about something similar. An inverse-VC type setup.
When you go for a VC, you ask to exchange a small percentage of ownership for a large stack of cash. Similar with accelerators, but they’re normally selling knowledge instead of cash. However, a lifestyle venture could, with a similar fund or group of bootstrappers pooling together, crank out lifestyle businesses. Instead of pitch decks being homerun swings, they’d be founders looking to get hired to build their dream (and help others build dreams if it fails).
This definitely goes well with the blog post saying that making good money and building products people love are the important parts. Hiring a culture of learning, inspired people could produce a series of small but profitable pieces of software that make lives better.
You could have a flat or mostly-flat setup like some other businesses (Valve, GitHub, etc) where people join products to make them happen. New hires come from pitches of people wanting to build something new or join in on an existing promising or profitable product. “Management” is exchanged for experts and everybody owns a piece of the company.
Again, this is mostly just fantasizing, but the idea is to create a collaborative, communal environment where people can work on making super amazing products and grow themselves. IMO such an environment would be a success story if it can regularly pay above market value (preferrably high above) and gets known as a haven of really intelligent, passionate people that then attracts and retains the best talent.
Edit: The biggest challenge here seems to be chicken-and-egg. The idea almost precludes wealthy investors dropping in cash but also might be nearly impossible to get a group of people to build the first couple of products. Any ideas on how to get such a thing started?