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What do you think would happen at Acme Inc., a company with more than 1000 employees, if one division suddenly demoted/relieved the manager, gave each teammate a gratuitous sick/vacation policy, and rotated frontline employees through the management roles?
I work at a company of over 300 employees, where we implement many of these kinds of ideas: we don't count sick or vacation days, our management hierarchy is extremely flat, and we have no policy about what time people come in to work. Despite that, I think this method of management-via-non-management is not something that every company can try on. It has to be built into the culture from day one. DHH is really only describing the trappings of a fun company culture, not the core of it.
You can't take the outward symbols of that culture and pin them on a company which doesn't approach employee trust and management in the same way.