Very interesting to get a data point on this. It takes a new employee 18 months to adapt to this work style, and then 25-30% never adapt. I'd imagine that is impossibly impractical for most companies, ignoring even the cost of moving your company to such a system in the first place.
I could also see the much more limited decision space being a factor in this. You're talking about when to put in money, when to take it out, where, and how much. And you can clearly see how well it worked out in the end. I wonder how effectively such a system works when applied to the software space.
I do believe that the principles he talks about as being very valuable, so actively stress testing all of your beliefs, and then collective decision-making (sounds like wisdom of crowds). And I guess you'll never truly reach idealized collective decision-making unless you implement a system like this. So if you decide that's the most important thing, and the majority of the impact of your work is in the decisions that you make (e.g. once you decide to purchase this stock, implementation is trivial), then I guess it makes sense. But I think in software, the ratio of decision-making to implementation is skewed heavily in the opposite direction, lots of decisions are being made in parallel by your thousands of employees, and the impact of each individual decision is much smaller than at his hedge fund. Getting into the habit of pulling multiple to a whiteboard might already get you close enough for such circumstances.
There also seems to be an aspect of judging each other on the company's key values. So then you can get constant feedback from every meeting you're in, how much you live up to the values that your company believes in, and your opinion is then weighted based on how well you match those values. Again, I would question how valuable it is to do this and in what contexts. I personally tend to believe more in the idea of leaders espousing company vision and values, almost like a preacher in a church.