And while they may not have anyone with the job title CTO, I'd be very surprised if DHH was anything other than the de facto CTO.
However, if you want your company to grow into a Groupon or Zynga, and you have the rapidly expanding demand to support that, then you need to scale. I don't think Groupon could run on 26 people, so they needed to scale to get to such massive revenue figures.
I specifically didn't use Facebook as an example because I know your feelings about them. I figured Groupon at least has the revenue to support their valuation :)
You can't "want" your company into becoming a Groupon or a Zynga by design a certain organizational structure. Startups try that all the time by preemptively hiring tons of people to sit around and wait for the hockey stick growth that never comes.
Well let me ask you this. When is it the right time to reorganize and evolve from the flat structure because you are growing like gang-busters and can't keep up with the pressure on all areas of the company (support, development, sales, etc.)
I think if I already had a business of 10-15 people this would be a good model to attempt to follow. If I had a business of 40+, I would be far more wary; the question of scale is for those who may try to fit the model to their existing business.
The assumption when you publish an article is that you're doing it to provide examples to others, not just talk about how good you are. In that situation, I think it's fair to point out the limitations and areas where this strategy might not work.
http://en.wikipedia.org/wiki/Ricardo_Semler
Their industrial democracy approach has scaled quite well, with 3000 employees.
http://en.wikipedia.org/wiki/Worker_cooperative
I think the biggest reason most companies don't recreate Semco's example is that nobody wants to think of themselves as expendable, especially people who can decide whether they're expendable or not, as the top management positions of a company are in a position to do so.
By saying "yes, our employees can make these decisions without us, we just have to give them the structure and support to do so", people at the top are admitting that they're not as important as our society tells them they are.
In Semco's case, Ricardo Semler was happy to admit that, because he felt the stress of running the business was killing him, and he welcomed the idea. A lot of people in his position would take anti-anxiety medication and something for acid reflux, and keep going, convinced that their position holding the reins is indispensable.