Asked about what sorts of feedback mechanisms he tries to put in place, He says,
I really think it’s too early to answer that, in the sense that I can tell you what I think today and the changes we’ve made over the last year and things like that. Stripe has been a thousand-person organization … or has been a more-than-500-person organization for just over a year. We’re beginners at this! Three years ago, Stripe was under 100 people
Again, pointer from Tyler Cowen.
It sounds as though Stripe has only recently gone from being sub-Dunbar (fewer than 150 people) to super-Dunbar (more than 150). That is a really challenging transition. In a sub-Dunbar organization, informal communication channels work best. In a super-Dunbar organization, much more structure is required. As a result, it feels as though the organization is becoming stale and bureaucratic.
I joined Freddie Mac late in 1986, not long after the company moved definitively into the super-Dunbar range. Some people who operated effectively in the sub-Dunbar phase became dysfunctional in the super-Dunbar phase, and even those who were still effective often were less happy. I think even the CEO felt less comfortable with the larger organization.
Great long form mag-style post on Stripes origins and growth.
Very important difference between start-up flexible speed & bigger, slower companies:
the dissatisfying situation where you have to make a highly consequential decision [and] there’s a lot of uncertainty. “We could have less uncertainty, we could take steps to mitigate that, but we just don’t have time to.”
Unspoken is that, for many decisions, a quick, reasonable but sub-optimal decision is better than spending time to choose a better decision. NOT making a decision leads to the creation of more problems, faster than making a weaker decision — as long as it’s not a bad, or very bad, decision.
(As I live blog the read, Patrick says this, more relevantly)
I now just place more value on decision speed. If you can make twice as many decisions at half the precision, that’s actually often better. And then, given the fact that the rate of improvement of decision making with additional time almost necessarily
tends to flatten out, I think that most people—certainly that Patrick of five
years ago and partly from Patrick of today included—should be operating earlier in that curve. Make more decisions with less confidence but in significantly less time.
I was in a sub-Dunbar (~15 people) startup company when we brought in a very successful manager from a super-Dunbar organization. It was a disaster. We didn’t have the sorts of communications bottlenecks that he was used to fixing (or exploiting, as need be).
Worse, he alienated our main investor by high-balling his budget request by a factor of about 4. In his native environment, that would have been an effective starter for negotiations. Our angel investor saw the huge cost increase and shut us down. If you’re used to an organization where decisions take months, you’re probably not prepared to manage a stakeholder who can make an adverse decision immediately.