Have you tried doing this? Can you share your experience and any success/failures you have encountered along the way?
Their biggest fails came with managing the tremendous growth of the organization. Logically, technically, strategically it was all tied off very well. But relationally, even ethically there were some gigantic blind spots.
Typically an individual can deftly handle tech OR people with a high level of fluency, not both. This person was extremely good at the former. But the latter was basically the leg day that had been skipped for years.
I recommend that you think about the kind of people-powered organization you do, or don't, want to build, and how that might look in the context of this undertaking. (Maybe that's not urgent for now though)
What do you mean by ‘well implemented contingency thinking’?
"I knew people wanted to do A. But I thought it'd also be helpful if when you did A, a feature like B could be there to prevent really common mistakes. And in this other set of features over here, if an annoying thing like C ever happened, well, I put in stop-gaps D and E so it was much less of a problem."