Drew Houston: evaluation

Transcript context

…What helped you come to that place? Because that sounds like a very hard place to get to and a very important place. Was that Bill Campbell advice? How long did it take you to go from this is not going well and life sucks to, okay, let's look at it this way? I think there were a couple unlocks that were pretty fast, but I think again, this was not like, oh, then I felt better and we lived happily ever after at all. There were some moments of recognition where I was able to, I always try to get away from the mayhem or the whirlwind and recenter myself and do think weeks and things like that. And so those were really helpful because I felt when I diagnosed, well, when I'm on this treadmill and just firefighting or how did I miss this important thing? It's like, well, basically the root causes of being on the treadmills, I was too busy firing to aim, and then I thought I would do my aiming on vacations and things like that. But no, I need to get off the treadmill every now and then and make the space to really address some of these bigger questions. Because it's not like I didn't forget about them. They just were always below the fold on my to-do list to deal with. And then until a few years go by and you're like, wait. Yeah, we really were just strategically out of position. The other way I came to some of these conclusions is a combination of things. So I think picking up a meditation or mindfulness practice, having therapists personally, having coaches, having friends and mentors, other founder friends. And so I wouldn't say it was any one thing, but I think you have to build this whole ecosystem of support around yourself and recognize no one's going to do that for you. And it's super important. And then to Bill's other point, he was like, yeah, Microsoft wasn't killing us, we were killing ourselves, I think having to ask some hard questions to myself of, yeah, some of these wounds were self-inflicted. As much as there might be, I could look at this and say, oh, Microsoft is mean, or Google was mean, or Apple was mean, but I'm like, I drove the ship towards these rocks. So that's one downside of being founder, CEO. You can't blame the last guy. I think one of the big questions every founder has to figure out is not just, how do I have equanimity? What's my purpose? But then also, what am I doing that is destroying the company? Because everybody's got strengths and weaknesses, but as CEO, both your strengths and your weaknesses are massively amplified and a lot of blind spots in your personality can become huge cultural dysfunctions in the company. And so step one to dealing with that is building awareness. And one thing that floated around the company for a while was the Enneagram, which on the surface is a personality typing thing like Myers-Briggs. I often describe it as it's like Myers-Briggs, but actually useful. The way it works is it's a personality typing system. You get a number from one through nine that's your dominant... Or there's nine types that are numbered. It's similar to Myers-Briggs in that Myers-Briggs has 16 types of letters like ENFJ or different things. But I find that Myers-Briggs is more descriptive. So it tells you, okay, you're an introvert, not an extrovert or vice versa. n that Myers-Briggs has 16 types of letters like ENFJ or different things. But I find that Myers-Briggs is more descriptive. So it tells you, okay, you're an introvert, not an extrovert or vice versa. You're judging instead of perceiving. But I could never really work out what that meant. And so it's descriptive versus predictive or causal. Enneagram I find is the theory that is really about your fundamental motivations. What are you running towards and what are you running away from? And the theory goes through some combination of your wiring from your genetics and your early childhood. Your autopilot is fixed after your childhood in that you just have instinctive responses to things. Now it's autopilot. It doesn't mean it's your destiny. You could override it, but it's super important to become aware of what are you running from and towards. And the Enneagram gives you a really good map to do that. And so I'm reading this book and it starts by you type yourself, and I'm rolling my eyes. I'm like, okay, I'm a seven. What's a seven? And then you read, each type has its own chapter and you read the chapter and I was like, oh my God, this completely describes who I am down to my core. And I was almost looking over my shoulder. Who the hell did this? I thought I was a special snowflake, but apparently not. Okay, I'm listening. And [inaudible 00:45:16] with a lot of my early coaching experiences, which are, you do a 360, your coach sits you down, they're like, here are your strengths. In my case, it would be things like, oh, you're really creative and you like new ideas. That's okay. And second, you really love people. You build great relationships with people. I'm like, okay. Uh-huh. Third, you're really comfortable in chaos and resilient. I was like, this coaching thing is great. See, yeah, that was my first coach. And then you flip to your development areas because no one calls them weaknesses. It's like, all right, one is you're bored by routine and really undisciplined. Second is you're really conflict avoidant. And third is you're intuitive, but you're also pretty chaotic and don't create enough structure for people so they're mostly confused. And when you pair the two together, you're like, oh, wait. Yeah, I'm creative and like new ideas, but I'm bored by routine and I'm a bit of a space cadet. All right, you love good relationships with people, but you don't want to make them unhappy so you don't tell them the truth basically about things that are difficult to hear. And it's going to be a similar map of things depending on your personality type or circumstances. But the Enneagram was that map for me to be like, okay, I've got these things that are genuinely great, but I need to address these downsides of the company's conflict avoidant, so we're not telling the truth and then making a bunch of predictable mistakes, or I'm creating this really chaotic environment where people don't know what they're supposed to be doing. That's a problem. My personality is quite directly, I'm going to torpedo the company unless I do something about it. The same is true for any founder. And I'm a type seven, it's the enthusiast.…

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