The Pioneer
The frontier and an appetite for the unknown, goes first.
Stewart Butterfield emerges in this interview as a Pioneer, someone who has repeatedly navigated the frontier of technological transformation and carries hard-won pattern recognition about how new platforms reshape work and human behavior.
“Almost everyone in the room, I had personally convinced that they should come work at this company, that they should accept our stock options, that they should believe in the project, that they should believe in me. And so it's... Like it's humiliating.”
“I think we were. You go through a trauma with a group of people and you really get bound to them. It makes you very close. And so I think we all wanted to continue to work together.”
“I said that there were good parts as well. And I got to say, you know, I use the bootcamp analogy in a deliberate way. I learned an amazing amount. Some of it was negative lessons, like, you know, don't do this. But a lot of it was positive lessons. And it also was just really eye-opening.”
“Yeah, they had restored an old lock cabin that was built around the turn of the last century. Didn't have running water until I was three, didn't have electricity until I was four. It was actually a funny story of my mother's father who came from Poland to Montreal in between World War I and World War II, coming to visit them.”
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