This proves it's possible, even when you're young, stressed and unprofitable.
You say that as if it was a bad thing.
People need fun. It makes them feel better. People who feel better work better and are more productive. I wouldn't be surprised at all to find out that an extra day of fun makes the four days more productive than the five days of work.
Hours worked is a lousy way to measure the contribution a person makes to the organisation.
Maybe you need to get out of the office more, bud.
What I think happened here is that you did a number of things right which affords you this flexibility in hours. I would say the real story is that you made something of value vs the free-but-pointless model we read about much more often these days. You built a business around something valuable with a relatively high price point that makes it less of a victim of the kind of scalability issues that "general public" web based services are dealing with.
I think the bigger take away would be: If you make something awesome for the general public that millions of people will be using all day long, plan to work seven days a week 'round the clock and there's no guarantee you'll ever see a penny. If you come up with something valuable that people would be willing to pay $25-$50 a month for, your life will be much, much more enjoyable and you might actually get to watch your kids grow up and/or have some time left for your hobbies.
I don't know how he did it, but his posts suggest he built the company this way, not just introduced it as a working practice later on. Maybe some employees will post here what they actually worked... although I don't doubt there were weeks that were more than 4 days.
But that aside, I have my own project, I won't call it a startup yet. I work on it evenings and weekends, maybe that adds up to 2 days per week total, the rest of the time I freelance to earn $.
So for me, Ryan is not just providing an aspiration of work/life balance, but actually that you can build a company in the first place without having to work 7 days per week.
It's easy to think this is impressive, but the reader forgets about the number of years Ryan has worked on creating businesses. He has made awesome stuff, but all that time can't be ignored. The suggestion that others can easily do it too if only they were less "messed up/caught up in old manufacturing ways", is some smug shit.
These crazy hard-working Americans are trying to figure out their first startup, with very limited resources. It's a different game, and they are in a different place in the food chain.
I am sure if they too have sold multiple companies and worked in the industry for 10+ (?) years, they too would adopt all kinds of relaxed ways of working and running firms. I agree that if they still work long hours after that, it is misguided as you point out.
But lets not get carried away with how the 1% works. How many days a week did you work on your first company?