Drew Houston: belief

Transcript context

…I don't know what made me want to be a founder. I just showed up that way. And so, there's probably some chemical imbalance of some form that causes people to do it, but I had a lot of insecurity about should I be a CEO? Because coming from the technical side, because I was like, I can do the engineering and technology, but all I know about being a CEO is I do not know how to do all of those things that CEOs do, and I do not look like that, I do not talk like that, it's intimidating. So I think first is it doesn't have to be an all or nothing decision. I mean, obviously it's all encompassing decision to become, to start a company, but you'll have many points along the way where you can keep calibrating. And I think the biggest thing is, or advice I got from one of the founders of a company where I worked was I was like, oh, should I be CEO? Should I not be CEO? Should I be CTO? He's like, "Look, just try it, be CEO, see how it goes." Initially, I thought I was like, all right, well I'm going to get the company to 100 million valuation and the trend will just be going faster, faster and faster, faster. And instead of just getting thrown off of it, I'll just hit stop and retire. And I thought that sounded like a great plan. But then, moving to the Bay Area, you suddenly meet, you throw a rock and hit 10 people who've done that. And what do you learn? This was just shocking to me because I talked to one of the advisors I mentioned earlier. He's like, "Yeah, the day I sold my company was the saddest day of my life." I'm like, "What?" As a 24-year-old, and he's like, "Yeah. Well, I just felt like the company had drifted away from what it was supposed to be and I just didn't like it." I think they're certain in the founder mode trough where you're like, wait, things are screwed up and it's on my watch, but I'm not really sure what happened and what do I do about it? So I think burnout is the biggest thing that will kill you. And so, I think that's why these coping methods and getting your own head is important, but if you do that, then it's also this amazing experience. And then often so many founders go back and start another company and another company. And you don't have to, but there's a reason that people do that because there's just a lot of rewarding aspects of it, building great things with great people that impact huge populations. What I found is that founders keep doing this because they love it in some way, or at least have a love-hate relationship with it or can't imagine something else that they would otherwise be doing and I'm probably the same way. But I think to get through that, you have to, Ben Horowitz also said the hardest thing for a CEO is to manage your own psychology. And we've talked a lot about, yeah, first you have to be aware of what your psychology is, and then how do you make sure you're not resenting or hating your company or yourself and view... I think the hardest thing for a founder, challenge is not optional. aware of what your psychology is, and then how do you make sure you're not resenting or hating your company or yourself and view... I think the hardest thing for a founder, challenge is not optional. You're going to be challenged, but the suffering is optional. You don't actually have to suffer. I mean, look, there's crunch periods or times where it's taxing, but it doesn't have to be this experience of suffering all the way or burning out or being really angry and sad all the time. Although certainly, in my experience that I did get in periods where I was just sad and angry all the time. So you need to figure out how do you work your way out of that. So along those lines, I'm curious, so you've shared a few things that have helped you level up as a leader and push through that. You mentioned meditation, Bill Campbell, a coach. You mentioned a few books. What has helped you continue to level up and stay ahead of where the company needs you? Sometimes you fell behind, sometimes you're ahead. What are some tips for founders that are trying to stay ahead of where things are going?…

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