[j_baker]

Sure I agree. But on the other hand, the Joel Spolsky article I posted noted that he started having problems once he got to 17 people, which is smaller than 37signals. I was simply using Google as an extreme to illustrate my point.

> Since large organizations, if they are designed well, are just a latticework of small organizations maybe it's possible there is no upper limit.

How do you make a smaller organization though? By giving someone authority over it who can really take control of it.

> Regarding David's larger point I would add that having a boss tends to make people feel slavish and subservient to a certain extent.

Tough. That's just the way it is. You're always going to have a boss. Whether it's a manager, a C-suite executive, a board of directors, or the customer. You're never going to be completely free from someone having authority over you. It's just a matter of how they use that authority over you.

Now, I will agree that bad bosses (which are unfortunately too common) make you feel slavish. If you have a good boss (and let's give DHH credit, he sounds like he is a good boss), then they make you feel powerful. A boss's primary job is to enable you to do things either with encouragement or by taking care of the administrative details for you. Someone once said that a boss is a "secretary who can fire you."

[nostrademons]

FWIW, I've heard that Google once had no managers. The person I heard it from started around 2002, when Google was already an order of magnitude bigger than 37signals. So while it obviously doesn't work for all size companies, it seems that you can get fairly big and still do okay without managers.