Training Data · Tuesday, September 15, 2026
In a lighthearted exchange, the podcast host and Aaron Levie discussed the concept of 'pain and suffering' in business strategy, humorously relating it to root canals. Levie expressed willingness to discuss difficult topics.
“I am wondering though, I know this is a different podcast, but when do you talk about root canals in this? Oh my gosh. Are we going to call Doug Leone? I don't know if we figured out how to weave that in yet or not? I mean, I'm happy to talk about different kinds of pain and suffering that I've been through. We should just do this pod with with a live root canal. Let's do it. Actually, that would be hot ones, but you get a root canal and you have to talk about your strategy while you're in a dentist chair. And Doug is just on the other end of it. Amazing, amazing. Doug is so pleased with himself by the way right now. Oh my gosh, he's very pleased with himself.”