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Drew Houston

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118
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2018-08-27
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2018-08-27
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  1. “So I go back in there. And it's like... Detonation. It's like I say like three words, and Paul's like, no. He's like, I'm not going to see your stupid demo. The whole reason we have an application process is so that Rando's like you don't just show up here and bother us. It's like, no, please leave.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  2. “But it's like awkward. So I step outside and I talk to Jessica, who is his partner in co-founding YC together and his wife. And I talked to Jessica. I'm like, hey, look, Jessica. And I had met Jessica before. So I'm like, Jessica, I'm really sorry to bother you guys. I just have a co-founder who was like looking for some feedback from Paul to make his co-founder decision. I got a flight back in like four hours. I'd swear I won't take more than 60 seconds of Paul's time. Do you think it's okay if I go in there? And she's like, oh, yeah, Drew, of course. Like, no problem. Paul's not doing anything, just like, just it'll be fine.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  3. “I get a zip bar. I fly down 101. And the plan was working pretty well. I got to YC. I went in the office. As expected, people were just chilling and kind of, there was some downtime. And so I go, I go to Paul's office. And sure enough, he's in there. He's just chilling. I'm like, hey, Paul, do you have a minute? I just wanted, you know, I just wanted to show you something I'm working on. And he's like, nope, I'm busy. And I'm like, okay, look, I'm like, I can almost see your screen. I know you're just hitting Hacker News right now Not actually busy.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  4. “Or 11. So I'm like, oh, actually, wait, this is YC has its dinners on Tuesdays. Maybe I could just like drive down to Mountain View and just pitch Paul.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  5. “And so hilarity ensued. But then I flew out to San Francisco. I'm like, I'm trying to shake the trees for any co-founder candidates I hadn't thought of because for one reason or another, all of my close friends and people that would have been the folks that I would have leaned on, like the timing wasn't good. They didn't want to do it, whatever else. But I found Another friend of mine, I was actually managed to get a friend of mine interested out in San Francisco, but he's like, okay, I'm interested. I don't know, but I want to know what PG thinks before I make a decision. So I'm like, okay, great. And I'm like, it's a Tuesday. It's a Tuesday at like 1 p.m. My flight back to Boston leaves at like 10.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  6. “To be at the top of Hacker News. That can't happen anymore because for a bunch of reasons. But I was pretty happy about that. And then I'm like, okay, so far the plan seems to be working. Because especially at the time, they didn't like single founders applying, and I didn't have a co founder yet. This was before I met Arash. So I was like, oh God, because the only problems I agreed with him, the only problem was the application deadline had already passed, I had already applied. And the interviews were in like two weeks. And so I needed a co founder in two weeks, which is like saying, hey, I know you're not dating anyone, but you need to get married by a”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  7. “Something like that. It's like, how do you do that when you have no money? And so there are the tactic of putting a video on Hacker News or creating a viral video is... That was a seed that was planted by Reading Gorilla Marketing. And so, but I made a screencast, which is like a three-minute demo of how Dropbox works because I wasn't ready to shift the code, but I wanted some feedback and I wanted to get into YC. And that video both got me into YC and it got me a co-founder. But I didn't know that at the time. So coming back to, so then what happened with this meeting with Paul? So I put the video on Hacker News. It hits the top of Hacker News for multiple days. It's a lot.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  8. “On Hacker News, maybe I can get in front of the Danube admissions here and get Paul's attention and go from there. It actually worked. So I made, and there's a concept from a book that I had read on that roof called Gorilla Marketing, which is like, how do you get attention and users for your product if you have no”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  9. “Things about coming from college admissions is you sort of learn how these admissions processes work. And YC was not really that different. You have a lot of people applying for a few spots. And so in addition to getting the scores and the grades and everything, one of the things you can do is try to stand out and do something kind of unique. And so I'm like, all right, well, maybe to help me get into YC, I'll try to put a video out about how Dropbox works. And Y Combinator also had their own, they just started this new site called Hacker News, which is kind of like Reddit for startup news. And I'm like, I had a hunch. I'm like, what does Paul do all day? I think he probably does what most of us do, which is hit refresh on hacker news all the time. So I'm like, maybe if I put a video.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  10. “But I applied and didn't get in, and I was super disappointed. So that didn't go well. But a couple years later, I wanted to apply again with Dropbox. And this is skipping ahead a little bit, but I had the idea for Dropbox, started working on it, and I wanted to do YC because a good friend of mine, or for many reasons, but another friend of mine, this guy, Adam Smith, no relation, who was one of friends from college. He did YC in 2006 and had an awesome experience. And I had like a front row seat to that and saw how much fun they were having. And then their company was just in a much faster trajectory because of YC. And I'm like, oh my God, I want something like that. But then so I started thinking about applying for YC with Dropbox. And one of the good things.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  11. “But we didn't really virtually meet. It was just sort of like a college admissions thing. It's open application. Anybody who wants to submit an application for the Summer Founders program, which is basically it was like the same thing as White Combinator, you get a little bit of money and all come together. It was sort of Y Combinator version one.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  12. “Spam filtering. So he's also one of the originals or one of the architects, or at least involved in that community of people who would figure out how to get rid of spam. And that's actually how I first heard about him, but then he started writing about startups and then ran this experiment that became Y Combinator, but it was actually called the Summer Founders Program, and I was digging through some old email about it because this was the precursor to Y Combinator. I applied with my SAT Prep company to that and was rejected, but then managed to get into Y Combinator a couple years later. So I guess the first virtual meeting of applying to be funded didn't go well. The first in-person meeting was probably...”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  13. “Yes. So Paul Graham is best known as one of the founders of Y Combinator. So they are, which is an incubator for startups, and they were our first investors, and they also invested in a lot of great companies, including Airbnb, Stripe, a lot of them. And Paul was, before starting My Combinator, he had written, he was an entrepreneur himself. So he started a company called Via Web back in the dot-com, or the first dot-com boom, and sold it. And then he had a lot of really provocative and insightful essays on startups that gained a big following. And he was also one of the creators, or at least was very early in the conversation around using Bayesian methods, using this kind of math to do.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  14. “And I'm like, and that's only if everything goes well. That's like if all of our dreams come true. So I'm like, I need to do something else. And so I ended up with these side projects and then found myself getting totally obsessed with first the poker bot, but then even more so with Dropbox. And so sometimes it's hard. How do you deal with burnout? How do you know if you're doing the right thing? These are really hard questions. I mean, for me, sort of listening, sometimes a lot of procrastination is unhealthy, but sometimes that little voice is leading you in a much better direction.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  15. “But it was a couple things happened. So, one is I like pause. I'm like, okay, I'm working on this company. I'm kind of burning out. Part of why is because I thought about like, okay, even if all of my dreams come through and like everything we hope for happens with this SAT Prep company, then I'm like, then what? And I'm like king of SAT prep. And there's nothing, I mean, I think that's fine, and people need help with these things. But I'm like, that's not what I want to do. I'm just picturing this kind of cardboard crown.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  16. “Problem, yeah, yeah, back to self flagellation. I'm like, oh, I can't. I'm like, I keep doing this. I suck. I'm not like I hate my thumb drive. I'm like, I hate me. But I'm like, oh my God, I just cannot deal with this problem. This is so stupid. I'm so sick of emailing myself a file. What is the question for which there's no question for which that's the right answer? Think of the physical equivalent of that. Taking an envelope, putting something in it, putting your own name in the to and from, putting it in the mailbox and getting it back. I'm like, this is what we do to manage our files that, carrying on a thumb drive, all the things we used to have to do. And I'm like, I never want to have this problem again. So on the bus, I open up the editor and started writing some code.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  17. “I was like, all right, well, I graduated from college. It was about 2006, late 2006. A lot of my friends had lived in New York, and they're like, you got to come out. It's a lot of fun here. Just come out for the weekend. And I have a dilemma because I'm like, well, I need to get some stuff done for my company. But I also want to go to New York. And I'm like, maybe if I take the Chinatown bus or if I ride the bus, I can have four and a half hours each way. So then I'll have 10 hours should be enough time to do what I need to do. You know, the elaborate rationalizations we come up with. And so I'm like, okay, if I take the bus, I'm green light to go to New York. Then I get on the bus and I've forgotten my thumb drive.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  18. “And then along the way, so I continued to work on the SAT prep thing, but then the founding story of Dropbox was, well, I had to use, well, the founding story of Dropbox starts with forgetting my thumb drive and going on the Chinatown bus, which I'll get to. But before that, I kept having these problems working with my co-founder because or collaborating with him because we didn't have an office, well, we bootstrapped the company, so we didn't raise any money and we didn't have an office. We didn't work out of the same place. And we didn't have servers. We didn't have anything. So we would just email stuff back and forth. And I had to work on multiple computers. So I kept carrying around this thumb drive and having these elaborate scripts that would backup the SAT prep company all of our files to a server. And then eventually...”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  19. “They're kind of used to me having all these side projects, so they're just like, I hope it's not illegal, just unfortunately that side project had to stop because of that. In fall of 2006, it became like went from borderline to very illegal to do online poker. That project ended. So what's that about? What I took from that was like, well, first, I'm like, I'm not broken. I'm super capable of working hard. It's just like I need to find something that I'm really motivated by. And so that was a relief. And then...”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  20. “But it was scaring my family because I was living in Boston, but then we have a little summer place in New Hampshire. And I was like, my family's like, okay, come up this weekend. We're all going to be at the lake. And I'm like, okay. And then I get to the lake and I start unpacking my trunk. And I've had like three monitors and like all these computers. And I'm like, I mean, this is like a little cottage on a pond. It's not set up to be mission control. So I'm like putting monitors on the stove and like things. And my parents are like, what are you doing?”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  21. “Well, I mean, Frankenstein was not too smart in the beginning. So the thing starts moving the mouse and playing the hand, then gets confused because there's some obscure multiple split pot or something that I just didn't write the code to handle that situation. So the thing crashes and folds your aces and you're like, okay, awesome. This is what AI looks like.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  22. “All that work and then watch kind of my Frankenstein moment as the bot comes to life and starts playing on real poker tables. And so this idea that you can't have poker bots was like totally false. But I was possessed. It was like, were you winning? Was Frankenstein?”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  23. “And I mean, now I recognize all this as burnout and a positive, there aren't a lot of good things about burnout, but sometimes the positive element is a consterior tension to things that are more worthwhile. But then I was worried because I'm like, oh my God, I'm so unproductive. And wallowing in this guilt, I was raised Catholic. So like this Catholic guilt of not, you know, I'm not working hard enough. This company's not successful enough. All my. And it's just totally not helpful. And so I'm like, oh my God, am I broken? Am I not capable of working hard? What's wrong with me? But then I would, one good news, I started working on this poker bot that started, and it played with real money. I got past the security on the poker client, this young six. So I figured out how to make.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  24. “So I started the SAT Prep company in 2004, and then I went back to school, finished my undergrad, and then a couple things happened. So after graduation, I started working as an engineer at a network security company. And I was still moonlighting on accolade, the SAT Prep company. But I found myself in a situation where it was like, it was just harder and harder to make progress on the SAT probe company. And I wasn't really sure what was going on because I just felt like it took more and more willpower to pedal. I felt like I don't know whether it was because I felt like I was pedaling harder but not getting anywhere or one way or another. But over time it took a lot more willpower to work on it. And so I found myself procrastinating with all these like”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  25. “Busyness from effectiveness and then the concept of leverage in high open management and a focus on output. So those two books have pretty much conceptually everything you need but then implementing it in practice is a lot harder.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  26. “Adopting no meeting Wednesday was utterly transformative in terms of actually being able to think and make progress on the most important thing. So otherwise you just lift up your head and you find like six months have passed on some important important priority of yours and there's been no progress. So think about how do you develop systems and how do you build in time for reflection and elbow at the time for you to think and set direction. I think that's probably one of the biggest mistakes that people make and one of the concepts from effective executive is like a lot of that stuff only makes progress with a half hour slot in a meeting of a day of 10 hours of half hour meetings. There's a minimum quantum of time for deep thought or deep work that you need. And so anyway, there's a lot of really conceptual foundations and effective executive about your time and effectiveness and disambiguating.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  27. “And she's like, but blah blah blah has this, and it's important. And blah, blah, blah has this, and it's important, and blah, blah, blah has this, and it's important. And I'm like, there will never be a day where there isn't something, quote, important, you know, coming up And so it's dawned on me in that conversation. I'm like, this is all important. But it's not. I was like, look, I really want, if it is important, just schedule it on Saturday. I'll come into the office. I'll do all those things. And then miraculously, those things kind of ended up doing themselves.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  28. “Kind of doing the equivalent of paying down a lot of high interest credit card debt with your time by just fighting all these fires and not actually putting them out at their root. So something I do on that front now is I have a, there's a concept called No Meeting Wednesday, which I think is popular around the valley, maybe it originated Facebook, I'm not sure. But we've sort of half-heartedly adopted that, and I half-heartedly adopted that for a while. I remember there was a I'm like, I really want to do this because there's all this planning and like all these things that are important where the cost of me not creating clarity for my team is super high. And I sat down with my assistant at the time and I was like, hey, I need to please don't schedule stuff on Wednesday. It's really important that I work on this particular project. And it's just not going to get done unless there's some, unless I have like a full day or like many hours of uninterrupted time.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  29. “For the two by two is important and urgent. Eliminating stuff that's not important and not urgent, but really the biggest crisis of prioritization is like, how do you make sure that you elbow out time the important, not urgent stuff? Because the important and urgent stuff will get taken care of, but then you end up with a lot of stuff that's not important or urgent not important or not important, not urgent, and you really want to cut those down as much as possible. Because otherwise, a lot of the fires, if you actually do a root cause analysis, think about why was this fire in the first place. When you kind of climb that ladder a couple of rungs, like why did this happen? Why did this happen? Or why this happened? Because of that. Why did that happen? Because of that, you find that just a little bit of planning would have eliminated the need to fight that fire. And so, but it's really easy to spend your day.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  30. “Usually, when you're to get too long, you just try to sort of do things randomly or just do whatever the last thing, you're just respond to whatever showed up most recently in your inbox or what blinked at you or what yelled at you loudest in the last hour. And that's not effective compared to having setting your own priorities and measuring yourself against them. This is a separate topic, but I think technology needs to do a lot better job of helping us do that because it's really hard. And then especially as you're in any kind of organization, the fires will get dealt with first and that's not a bad thing or that that's like necessary. You can't not put out the fires. But then the important stuff, or I'd say Eisenhower had this important versus urgent. Yeah, the matrix.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  31. “It I think at the end of the day, that's conceptually what you want to do. And then just understand that you're going to tend, and then you also want to offset the tendency for to be in this permanently reactive state, which whether that's because you're getting emails that are other people's requests or your calendar says one thing.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  32. “And categorizing it. I remember the first time I did this. I was like, all right, I'm running the company, things are going well. What do I spend my time on? Oh, back then. I was like, oh, I spend my time on the product and recruiting and when I actually did the inventory, I was spending no time on those things. I was spending, there was a lot of OPP back then, like just responding to following up on favors or speaking engagements that didn't really do anything for the company. There wasn't a lot of total fat like that. But it just, what you find is you write down your priorities and you look at your time and you find the things are totally mismatched. And so any mechanism you can to first understand where your time goes and then make sure your priorities actually match.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  33. “Requests without having the overhead of email. And I think these are all kind of email is just one example of a lot of different forces that can take away, that can kind of shatter your attention or take away your time. I think one of the most valuable concepts from the effective executive is measuring your time or understanding where your time goes. And it is kind of shocking and hilarious, but really tragic that we all think we know exactly where our time goes. But then when you measure it, you're not usually just like slightly wrong. You're like...”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  34. “Yeah, I try not to use a lot of email because often if it's, I think emails is good for quick, discrete tasks where you're holding someone up by not doing them. But if you're trying to, and then I think it's also useful for broadcasts, like if you have some long-form written direction that you want to give a group of people, then that's a good use of it. But often when people get into these long email threads, it's often, it sometimes be fun and indulgent to get into these big flame oars, but often the best way to, if you get a long email, often the best response is to talk to them in person. And if you're getting a lot of little requests, it's better to just batch them up and have some kind of weekly cadence where you can deal with a lot of quicker.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  35. “Or at least or smaller big, you should at least be mindful of it. A lot of people just find themselves hopelessly busy and on this treadmill responding to other people's to-do lists and no one is doing the things on their to-do list.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  36. “Or you can often tell by the question many, if not most of the requests will be something where the person could just do a little bit of homework and get a good answer. And that's troubling because at first you try to help people with those kinds of things. You're like, oh, well, you know, go to this blog post or do this thing. And then you don't hear back from them. And it turns out they just never followed up or just didn't do it. And so after you get burned by spending a bunch of time trying to be helpful to people who don't do their homework, who don't help themselves, you realize that's not how you want to spend your life. So you have to think there's a magic formula, but I think you want to just keep what you want to do is just keep that budget of your time constrained to something small.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  37. “I know, and where I personally would be really helpful, and they have done their homework, and I think there's a certain first pass filters like that. I would say there is no commandment from God that you have to respond to every email you receive. So if it's like a cold email, or if it's like someone I don't know, or it's like a sales thing or whatever, I just then it just goes into the black hole. Or if it's something like, you know, there's a lot of folks who are like, hey, I need a mentor, or how do I raise money?”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  38. “Yeah, so I think some people would say it feels cool even when I help. So I'm not great at responding to these things. So it might be, if it's something that's like not a priority, then I'll try to respond in days, but sometimes it's week, sometimes it's months, sometimes you'll get a response that's like, oh, yeah, it's seven months later. It's like, oh, here is, do you still need this? But so I think if it is something from a person you have a relationship with, I would say, and there's probably other factors, but it's like, okay, is this someone who...”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  39. “But yeah, I do have an OPP folder, which I try to keep manageable or find ways to, I think the best is if you can find ways to be helpful and involve other people in actually helping. I have a whole team of people who can help me respond to those kinds of requests.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  40. “Anyway, the interviewer was interviewing both Warren and Bill and was like, all right, in a word, what has made you most successful? And they both at the same time, like without missing a beat, both said focus. And so if we all, and it seems so obvious, we all know why focus is like, we don't need to be told why focus is important. But then one of the things that the effective executive highlights is that there's so many, like the default for pretty much anything is to unfocus you. And that's true of your inbox. Your inbox is not prioritized. It's just going to basically get all these requests that are other people's priorities. If you're working within an organization, pretty much everybody will be pulling on you to kind of feed the beast of the organization. And so it becomes very hard to do a few things well. And so, I mean, there's a lot of great things about that book.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  41. “But then to the OPP thing, I'm like, wait, then what are these things? What am I doing? And then you realize that you're just basically checking off items on other people's to-do lists. Where there's sort of in the abstract, there's nothing wrong with that, and it's important to be helpful, and we all have been helped by and help other people. But you can end up in a situation...”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  42. “Yes, so I think originally, well, yeah, it stood for other people's problems. Although I made it a little nicer later, other people's priorities. And because I have a vendetta against email, which we can dig into. But I've had this experience. I imagine anyone listening has had this experience. All right, your inbox is overflowing. You're like, I'm finally going to deal with this thing. You plow through hundreds of emails and your reward is more emails.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  43. “Developing both sides of your brain or developing an appreciation for both is really valuable. Maybe one more, so principles by Ray Delio, who was I know was a recent guest. I think he's got really concise and good thoughts for like, all right, how do you sort of approach all the mix of different kinds of things? I'd have more instructional books, more philosophical books, more story and history kind of books.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  44. “Developing both your left and right brain to use that analogy I think is really important if you're running a team or growing a company because there's a lot of stuff where it's a lot about technique and data and a lot of things like strategy or the engineering are kind of fall into these if-this then that kind of reasoning but then a lot of The hard part of the job is really about people and what motivates people how do you paint a vision of the world that's exciting for people how do you build good relationships how do you develop products with taste Those are things that are not going to be where you're not able to reach as much into the more rational or like kind of engineering bag of tricks. So I think developing both of those”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  45. “So you talked about engineers who dismiss all these things that can't be fit into an algorithm or that don't have some kind of mathematical rigor underpinning them. Zen and the art of motorcycle maintenance is about that just that question of you have this whole rational world which can explain a bunch of stuff, but then you have the whole aesthetic world which can't be boiled down to a formula and they both exist and they are both useful in different cases, but they don't tend to get along. And so how do you, so what's up with that? And it's a really great book about those concepts. And I think developing Appreciation for”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  46. “A batna and leverage that might be a concept that can be applied in all kinds of different situations or comparative advantage from economics. Or you could go on about these different concepts, but then figuring out how do you internalize them so well that you're able to figure out, okay, these are what matters in these situations. And then how do you avoid, how do you particularly avoid terrible decisions? But really, how do you build enough of, get enough of these, he calls it a lattice work, how do you build enough of a network of these mental models so that you know which ones to apply when, and that you find yourself most of the time being able to make good, quick decisions. And then also on the philosophical front, so Zen and the art of motorcycle maintenance”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  47. “How do you grow wisdom or grow judgment quickly? Poor Charlie's almanac is a great example of books. So it talks about how actually a lot of what you need to know to be successful in life conceptually you learn it in middle school or in high school. You just don't apply it or you don't really internalize the concepts. He argues that a lot of really wise and effective people develop or they basically build a catalog of mental models and concepts, whether that's something from, and basically assemble all the best ideas from all the different disciplines and then figure out how to apply them in life. And so”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  48. “Which kind of just shows you kind of a mess in adventure and the crazy highs and lows of what the human experience is of actually having to do this. And then I'd probably zoom out and get a little more philosophical. So a couple favorite books are poor Charlie's Almanac by Charlie Munger. So Charlie Munger is Warren Buffett's longtime business partner. One of the this book is really interesting because one of the things about being a CEO or taking on big responsibility for anything is you have to make a lot of decisions about a lot of different things and do it quickly and be right. And so how do you be right about tons of different things, especially if you don't have a lot of life experience? Like how do you train up that skill quickly? I mean, that's really called wisdom or judgment. And so it's like, how do you...”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  49. “There's a bunch of practices that you can adopt that make you more effective. And then how do you avoid the sand traps of things that feel productive but aren't actually? And how do you dissect or how do you unpack the case where we all have the same number of hours in a day, but some of us seem to accomplish a lot more than others? Why is that and what can you do instead? So the effective executive is covers a lot of that ground. That's two I think of as kind of like textbooks. Like you want to study them. You want to take notes. You want to really chew on the material. Then I think there's a lot of other tactical things about starting a company. I'd say some more of a favorite book that's more about the experience of running a company is Ben Horowitz's book, Hard Thing About Hard Things.”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT

  50. “Okay, how do you run a team? How do you break down a goal into subgoals? Just the 101 of running a team and running an organization and a focus on output and results and how do you measure people. And there's a lot of things that nuts and bolts things that you, challenges that you encounter when you're running a team, whether that's a company or a team within a company. The second is the effective executive, which does a great by Peter Drucker. And the central core of that book is really about people, it's very easy to mistake effort for effectiveness. There are a lot of different phrases for this. To confuse motion for progress, but it's really about that idea. So how do you know if you're being effective? What practices?”

    2018-08-27 · The Tim Ferriss Show · #334: Drew Houston — The Billionaire Founder of Dropbox · IDENTIFIED FROM THE TRANSCRIPT