Drew Houston Interview | The Tim Ferriss Show (Podcast) | Transcription

Transcription for the video titled "Drew Houston Interview | The Tim Ferriss Show (Podcast)".

1970-01-01T03:33:12.000Z

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Introduction

Intro (00:00)

At this altitude I can run flat out for a half mile before my hands start shaking. Can I answer your personal question? No, it is the end of the big time. What if I did the opposite? I'm a cybernetic organism, living tissue over a metal endoskeleton. League Ten, Paris, Seoul. This episode is brought to you by 99designs. Whether you need a logo, custom website, app, book cover, or anything else, 99designs was created to make great design accessible to everyone, that's you, and to make the process as easy as possible. I've used 99designs for years now. I've used them for book covers, some mockups for the 4-hour body, which went on to become a #1 New York Times bestseller, illustrations of all different types for the multi-volume The Tau of Seneca, which you can check out, and other graphic design projects for a long time now. And I've been very impressed by the quality of their designers and illustrators, and you don't have to take my word for it. 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This is Tim Ferriss, and welcome to another episode of The Tim Ferriss Show, where it is my job to deconstruct world-class performers, people who are exceptionally good at what they do, to tease out the routines, habits, favorite books, and so on that you can hopefully test and apply to your own lives. And my guest today is none other than Drew Houston, H-O-U-S-T-O-N, @drewhoston on Twitter and elsewhere. He's the co-founder and CEO of Dropbox. Since founding the company in 2007 with Arash Ferdowsi, Drew has led the company's growth from a simple idea to a service used by 500 million people around the world. You can let that number sink in. Drew received his bachelor's degree in electrical engineering and computer science from MIT in 2006. I think I've heard of that place. After graduating, he turned his frustration with carrying USB drives and emailing files to himself into a demo for what then became Dropbox. Today, Dropbox is one of the world's leading business collaboration platforms with 11 million paying subscribers and 1,800-plus employees across 12 global offices. Drew, welcome to the show. Thank you. You know, I've wanted to have an excuse to ask you for your life story and all these details, because we've known each other quite a while, but it's super weird to sit down with a glass of wine at a dinner table or something like that and just start asking you for your Dr. Evil story. So this is a fun opportunity for me to dig in. So I appreciate you taking the time. Awesome. Yeah, me too. It's great to be here. And I thought we would start with some of the backstory that I do not know, and that is your childhood. And perhaps you could just begin by telling us how you would describe yourself as a kid. I mean, let's just call it kind of three to sixth grade or any time, really. What type of kid were you? So, yeah, going way back. Well, first I was definitely that kid who was on computers. So my parents, I remember just like toddling into my living room and seeing this glowing orb and all these buttons, and those were two things I really liked when I was three. I guess still do. So for sure, I was super interested in computers and technology and started out by playing computer or video games, basically. That was like the first interest. And then I wanted to make my own computer games. I thought that my career was going to be starting a computer game company, and I thought that there would be nothing better than that. But I was that kid. I learned programming at an early age. I grew up just outside of Boston, so I grew up in New England. And then on my way to MIT, I really liked math, science. So kind of out of central casting in terms of being a computer science student.


Professional Journey And Influential Books

The transition from babysitting to programming. (07:15)

And then my first career was babysitting, but then I discovered that you could be paid to program, and then that caused a bit of a career shift, which we can talk about, as much as I enjoyed the babysitting lifestyle. You get like three bucks an hour, eat some Pringles, watch some HBO. It's not that bad. But programming was even better. Anyway, so in middle school and in high school, I ended up getting a bunch of programming internships or summer jobs at startups, basically. One of them was remote. Most of them were local. But then that got me on a path of starting companies and being involved in startups. But I would say those are probably the biggest, when it comes to Dropbox and everything, that kind of followed after from my childhood. It was a happy childhood, lots of--I would say it was still pretty balanced, but programming and engineering was for sure my first love.


Drew's reticence over the years. (08:32)

And were you a shy kid, an extroverted kid, played sports, kind of kept to yourself at recess? What would somebody looking in from the outside--how would your third grade teacher describe you in that capacity? Yeah, I think somewhere in the middle. So I wasn't reclusive. I had a really great group of friends. I wasn't captain of the soccer team either. I did academic decathlon, which is just a fascinating thing that it exists. But more of a mathlete than an athlete. I was not super social, but I had a good group of friends. And then for sure as I went into college, I became a lot more social and just curious about humans and human behavior.


The start of the folding chair education - selling test prep materials (09:32)

But otherwise, I think people--I would have been known in class as always doing--I think there were those superlatives in yearbooks. I think I was most likely to start a company. So they pegged it pretty early. Yeah. I was doing homework for this, which I always enjoy doing when it's someone I know because I dig up all these bits and pieces that I then want to ferret out and explore a bit. So I came across this line that described folding chair on top of fraternity at MIT and that you would go up there with piles of books and read these books. Could you place us when that was in your undergrad career and how you chose the books and why you did that? Yeah. So it was about my junior year of undergrad. I took a leave of absence because I had an idea for a startup that I wanted to pursue. So I took a year off to do that. What I noticed was that the--this was back in 2004, so I was maybe 21, and the SAT was changing. I started an online SAT prep company because what the opportunity was was the SAT was changing in 2004, 2005, from 1600 points to 2400 points. So suddenly all the course material overnight was going to be obsolete. And so I saw an opportunity to maybe develop not just a course for the new SAT but an online course, and I teamed up with a former teacher from my high school who had his own little cottage SAT prep company. And I'm like, "Hey, if we come together, we can put this thing online and we'll be on an even playing field because all those 800-page books that have been printed about it are now obsolete, and who really wants to go to some classroom at 8 in the morning on Saturday?" Anyway, we can build a much better experience if we do it online. So I was really excited about starting a company, and we jumped into it. I think we met in a Chili's and we're planning world domination and figuring out how do you incorporate a company. So it was a really great introduction to the world of starting companies. And then it also, the more I learned about the mechanics of starting a company, the more I realized I didn't know about business. And I knew a lot about engineering and programming, and I had worked at startups. But when it came to—but it was kind of that there was a fog beyond just building the product. And so I was like, "All right, we're going to need—I know sales and marketing and strategy, these are all things, and all I know is I don't know a lot about them." So I had the highly scientific method of—I just was like, "All right, I'm just going to go on Amazon, type in sales, buy the top three or four books, and just do that for every category." And then I had a couple book recommendations from one of the founders of one of the companies where I worked as well. But it was great. And it was an important combination. So one was actually starting a company gave me motivation to really learn the stuff, because I think a lot of times when you're reading, it can just be like entertainment, basically. It's like something where you just read the book, you're like, "That's interesting," but then don't use the knowledge. But if you're actually starting a company, then you really have an excuse to internalize and really study the material. So there's a big difference between reading the material and studying it. Totally. But I was pretty systematic about it. I'm like, "Okay, here's all the stuff that I don't know, and then reading is going to be a good way to get me introduced to all these topics."


Sales, marketing, leadership, and these lessons (13:32)

And all of that, maybe the first instance of that was when—I went through my high school, and there were a lot of great books that you read as part of your high school curriculum. But then I stumbled across a book, Emotional Intelligence, by Daniel Goleman. And I was like, "Oh, my God, this is just like—I mean, it's nonfiction, but it spelled out something that I just didn't know you could kind of break down in a logical way." And suddenly I have this understanding about the world that I didn't have before. And so that was important because it was sort of one of a bunch of early examples that anything is trainable, and it got me on a path to developing what we'd now call a growth mindset. And realizing that it's possible to learn about these things where you have no experience or where it's easy to be like, "Oh, I don't know about that," or "I'm just an engineer. I'm not a businessperson," and kind of shatter that misconception. Do you think that you were open to all these different categories of learning because of the necessity vis-à-vis starting the company? The reason I ask that is that it's not across the board, but some people with engineering chops seem to have a learned or intrinsic disdain for sales, marketing, these different bits and pieces of businesses that are a little softer, let's say, less quantifiable in some respects. Was it simply the motivation in building this company where you had to wear all those hats that kind of drove you into these different categories, or were you intrinsically—using that word quite a bit—but interested in learning more about these different buckets through these different books? I think it was a little of both. So certainly starting the company made it a necessity and created a lot of additional motivation. But the experience—I also found these other topics just as interesting as the engineering. And I think it's a big culture when engineers start off by being dismissive or defensive about the technology is all that matters, or if it doesn't have a triple integral in Greek letters, it doesn't count. It's like a cultural meme at MIT, and I think it just creates a huge blind spot for people, both because it makes them less effective, but it's also—the stuff is actually really interesting. But I kept having experiences like that. Emotional intelligence was just one example, but I took a class on negotiation at MIT, which sort of opened my eyes a notch further on this kind of thing, where I'm like, "All right, negotiation, I go into that class, I don't know a lot about it." I'm like, "Whoever yells louder, lies more, smacks the table harder, I guess that's what makes you a good negotiator." And then this class—those are tactics. But the class has these frameworks where, OK, smart people have thought about this and they've broken it down, and it turns out that there's a whole process of uncovering mutual interests and figuring out what your leverage is and your best alternative, and spelling it out in a way where I was like, "Actually, this is a lot more straightforward than some of the theoretical math classes I have to take, and it's a lot more applicable to my daily life." And so I really appreciated learning a little bit about a lot of different disciplines, and just putting up a folding chair on my roof was the first thing that came to mind as far as how I could actually do that. Were there any other books, besides Emotional Intelligence, during that period that really had an impact on you?


Standout books across sales, marketing, and leadership (17:31)

Yes, so in that negotiation class there's a book called Getting to Yes, which is about principal negotiation. And I still think about and apply a lot of those concepts today. So part of it was just doing a random walk on Amazon, but I also became friends with the founders of the companies where I worked. And during lunch breaks or other times I'd go chase them down and bug them and ask them questions about, "Hey, how do you start a company? Do you have any book recommendations?" Just taking advantage of being the bright-eyed, bushy-tailed intern and shaking down my boss or the founder or my mentors for advice. And so two of the books that were really instrumental, the first one is Innovator's Dilemma by Clay Christensen. It's a book about how businesses get disrupted and a lot of those themes are why startups can succeed and thrive even when there are big competitors who you would think would just wipe them out. And so how that cycle works. And there's a book called Crossing the Chasm, which is another classic. It's a book on marketing, technology marketing. It's like how do technology products make their way from early adopters to the mainstream? And have you found yourself revisiting those books, or were they a point in time during that rooftop Amazon education period? I have. I'd say you read a lot of books. Not all of them are as good as the Innovator's Dilemma. But then it also helps to revisit some of the classics. Innovator's Dilemma, actually both of those books are good examples. So yeah, I do revisit them because again, when you're 21 and you've never had a real job, you're reading this book and you sort of get a general sense for things, but you don't really deeply understand the concepts. And then coming back five years later, ten years later, you can really absorb a lot more of the material. So I read a lot of books in general and then when I'm reading a book, I'll triage. I'm like, "Okay, is this something I need to study? Is it something that's interesting or that I might need to know something about or is it just fun?" And if you study it, if I'm like, "Oh, I need to study this book," then I approach it pretty differently than if it's just entertainment. And for those people who haven't read Getting to Yes, when you were leading into that with some of the concepts from the class, I thought to myself, "I bet that was part of the class or one of the books you read because you had best alternative." And there's a term I do recommend also people read Getting to Yes, BATNA, Best Alternative to Negotiated Agreement, which is a really important concept to grasp. And there's another book that I might recommend to people. I think it was written later by one of the co-authors of Getting to Yes called Getting Past No. I think they go together really, really nicely. If you were teaching, say, a freshman class or senior class, undergrad, to let's just say smart but non-technical people, and you were assigning books to read, and they could be part of the class or things that could be read in advance.


The High Output Management for freedom thinkers. (21:07)

If you were to pick, I'm just pulling this out of thin air, but three to five books that would be the core of your reading list, do any come to mind that we haven't talked about? Yeah. So for the sake of starting, or if the subject of the class were starting a company or evolving from being an engineer to being a businessperson, I have a handful of books that I really love and the concepts that I use and think about every day. So probably my two favorites are High Output Management by Andy Grove, which Andy Grove was the CEO of Intel, which was kind of the Google of its time, particularly back in the '80s and early '90s. So Andy was one of the founding engineers and then rose the ranks at Intel and became CEO, so he's lived his path. When I read about this book, or I heard about this book and it was introduced to me as the best book on management ever written, and I agree, and it just breaks down all the mechanics of how do you run a team, how do you break down a goal into sub-goals, 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 you, 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, like to confuse motion for progress, but it's really about that idea. So how do you know if you're being effective, what practices, 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 covers a lot of that ground. Those 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 the, a favorite book that's more about the experience of running a company is Ben Horowitz's book, Hard Thing About Hard Things. Which just kind of just shows you kind of a mess and adventure and the crazy highs and lows of, and like 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. And 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 grow wisdom or grow judgment quickly? Poor Charlie's Almanac is a great example of the book. 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. And he argues that a lot of really wise and effective people develop or 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 do you apply them in life. So for example, the concept of a BATNA, like in 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 particularly avoid terrible decisions, but really how do you 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. Yeah, Pearsig. Yeah. 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 an appreciation for both, or 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 falling into these if this and 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 kind of engineering bag of tricks. So I think developing both of those, developing both sides of your brain or developing an appreciation for both is really valuable. Maybe one more, so Principles by Ray Dalio, who I know was a recent guest, I think he's got really concise and good thoughts for like, alright, how do you sort of approach all the, how do you approach life? So I would include a mix of different kinds of things. I'd have more instructional books, more philosophical books, more story and history kind of books. Man, I want to take your class. Number one, so consider me pre-registered or pre-applied. I want to make a couple of comments on these books that you mentioned because I am very fond of all of these books and I'll just add a couple of notes because they tie together also really nicely. High Output Management by Grove was out of print at one point and then became so popular in Silicon Valley that a new edition was printed and the forward, I believe, was from Ben Horowitz, who wrote another book that you had mentioned. You know, the, what is it, the Hard Thing About Hard Things? Right. And Ben Horowitz of Andreessen Horowitz and many other things prior to that. So that book, and there's of course a selection bias here since I have a limited data set, but the startups that I've been involved with that have done best, have kind of returned the fund many, many, many times over, almost without exception have all read High Output Management and have a copy of it in their offices.


Reference, hard things about hard things. (30:01)

Now, I'm sure there are many unsuccessful CEOs who also have that book, but nonetheless. The Effective Executive, actually I'm going to leave that one for last. So Par Charlie's Almanac is a great book and I want to underscore something that you said somewhat in passing, which is really important and I know you know it's really important, which is the avoiding of making really bad mistakes. And one thing that Munger emphasizes a lot, you know, the right hand of Warren Buffett, and Warren Buffett I guess has said he has the best 60 second mind he's ever met.


The lattice, mental models of thought. (30:43)

And I'm going to butcher this I'm sure, but it's something that I think of a lot because I have some tendencies that are unhelpful in trying to be really smart and come up with clever solutions. And I revisit this quote, somebody could find the right version, but it's Munger who says, "It's amazing how successful you can become if you just consistently avoid being stupid versus trying to outsmart everybody else." And I think a lot about that because it's so true. It's like, God, yeah, if you just kind of watch your chips and know your downside and don't make, you know, consistently make rational decisions with these lattice works and these heuristics that you mentioned, super, super helpful. And The Effective Executive. So The Effective Executive I want to come back to for a second. And you mentioned Nuts and Bolts. So The Effective Executive I've read probably 10 or 12 times. I love this book and it's very short too. It's easy to read. And you mentioned the sort of nuts and bolts. So I'm going to use this and then we'll probably jump around chronologically. But you, if I'm remembering correctly, have a label in your email called OPP. Could you explain for people what this means? Yes. So originally, 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. Like, 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. Right. But then to the OPP thing, I'm like, wait, then what are these things? Like, what am I doing? And you realize that, like, 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 where you're basically your to do list is a composite of other people's to do lists. And your calendar and your email can often reflect that. And tying it to another, so one of the most important concepts is focus. Everybody understands, like, yeah, yeah, focus. And I imagine something we'll probably talk more about here. But there are so many forces. People love the idea of focus. And when it was interesting, just going back to Warren Buffett. So Warren Buffett and Bill Gates did an interview. I think it's on Netflix. There's like a Warren Buffett documentary, which is great. I also recommend. But 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's like seems so obvious, we all know why focus is like, we don't need to be told why focus is important. But then, and one of the things that the effective executive highlights is there's so many like the default for pretty much anything is to unfocus you.


The Opportunity Folder (34:29)

And that's true of your inbox. Your inbox is not prioritized. It's just going to like you basically 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. But 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, but then like involve other people and actually helping. So I have a whole team of people who can help me respond to those those kinds of requests. So now the OPP folder, it's not this it's not necessarily a black hole. It's not an indefinite archive necessarily, but it's when I'll get around to it. Do you have a set schedule for looking in the OPP folder or having other people do that for you? And what are the criteria, right? Is it that anything that doesn't come from say, a direct report, or an investor or a family member goes into OPP? Or what are the guidelines? Yeah, so the I think some people would say, feel a call even when I'm 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 weeks, sometimes it's months, sometimes sometimes you'll get a response that's like, Oh, yeah, it's seven months later. It's like, Oh, here's, do you still need this? But so I would I think it's if it is something from a person you have a relationship with, I would say you and there's probably other factors, but it's like, okay, is this someone who I know and where I where I personally would be really helpful. And they have done their homework. And it's like, 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, cold call, if it's like some 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 I need a mentor, or how do I raise money? Or you can often tell by the question, like as a person, 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 like not how you want to spend your life. So you have to, you know, I don't think there's a magic formula, but I think you want to just keep what you want to do is keep that budget of your time constrained to something small. Or at least, small or big, you should just 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 knowing no one is doing the things on their to do list. Right. One thing you said about people doing their homework reminded me of this quote from Maria Popova, who writes Brain Pickings, which is this incredible site, millions and millions of readers and really long form, smart writing. And at some time, I think she changed it to be a little more maybe sunny seeming, but she had a quote, I'm pretty sure on her Facebook page as the graphic, as the header at one point that said, "If you haven't done or if someone hasn't done the homework to determine whether it's a fit or not, it doesn't warrant the energy to explain why it isn't a fit or something like that." Which I think is a great commandment or guideline to use because so much of it, when you reinforce that type of behavior by trying to be helpful, they just come back, people tend to come back with equally nebulous or unthought through questions.


Email and technology (39:03)

Do you have any other best practices or dos or do nots when it comes to managing email? Or not using email? Yeah, I try not to use a lot of email because often if it's, I think email is good for quick, discreet 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 broadcast, like if you have something, 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, I mean it's sometimes really fun and indulgent to get into these big flame wars. 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 quick 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 slightly wrong, you're totally upside down. So this is a really valuable exercise for anyone, but actually keeping a log of where you spend your time and categorizing it. I remember the first time I did this, I was like, alright, I'm running the company, things are going well, I probably, what do I spend my time on? Back then I was like, oh, I spend my time on product and recruiting and da da da, 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, just like 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 what you find is you write down your priorities and you look at your time and you find that 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 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 to be in this permanently reactive state, whether that's because you're getting emails that are other people's requests or your calendar says one thing. Usually when your to-do list gets too long, you just sort of do things randomly or just do whatever the last thing, you 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 setting your own priorities and measuring yourself against them. And 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's necessary, you can't not put out the fires. But then the important stuff, I'd say Eisenhower had this. Exactly. Yeah, the matrix, the quadrants, I guess it was four. That you elbow out time for 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 this happen, or why this happened because of that, well, 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 days kind of doing the equivalent of paying down a lot of like high interest credit card debt with your time by just fighting all these fires and not actually putting them out at their root.


CONCEPT: No-meeting Wednesdays. (44:11)

Right. 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 have half-heartedly adopted that for a while. But 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 that were 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, like, please don't schedule stuff on Wednesday, like it's really important that I work on this particular project and, you know, 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. 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, like, but it's not. And so I was like, look, just 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 and adopting No Meeting Wednesday was utterly transformative in terms of actually being able to think and make progress on the most important things. And so as you just, you lift up your head and you find like six months have passed on some important, unquote, 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 out the time for you to think and set direction. I think that's probably one, that's 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, that stuff doesn't make progress with a half hour slot in a meeting of, or in a day of 10 hours of half hour meetings. Like you, 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, great conceptual foundations in Effective Executive about your time and effectiveness and disambiguating busyness from effectiveness. And then the concept of leverage and high output 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. Yeah, we're going to talk about the practice quite a bit I think also in this conversation. I want to circle back to a few things you mentioned because I think they're really important. The first is the Eisenhower Matrix, I think it might be referred to as, which people can look up on their own time. But the correlating in some respects maybe exercise that I think Drucker brings up in the Effective Executive is the jar or mason jar. And people can visualize this very easily, but if you have a mason jar and next to the mason jar you have a handful of large rocks that can fit into the jar, then you have a bunch of smaller pebbles and then you have a pile of sand.


The Eisenhower Matrix and the Mason jar. (47:31)

All of which has come out of the jar. If you put in the big rocks first, i.e. your most critical tasks which may or may not be urgent, then you can fit in the pebbles, then you can fit in the sand and you screw on the top and it's nice and neat. But if you put in the sand first, the whole thing falls apart. You cannot take the same volume of rocks and pebbles and sand and get it into the jar. Which visually, from an imagery standpoint, is very easy to understand. The time audit, as you described, is so important for people to do because very often even your calendar is not a good reflection of how you in fact spend your time. If you look at self-reporting in dietary studies, where they're observational and people are going home and then coming back and reporting every two weeks or something like that, if you ask people to estimate their caloric consumption, it's almost always 30-40% off. It's not a small difference and I think the same thing happens with time really routinely. The blocks of time, actually, you know what, I'm going to make a reading recommendation and then I'm going to come back to this name which of course you're going to be very familiar with. For people who really want to also get a teaser for what you'll read more about in the Effective Executive, there's an essay. I might be getting the headline slightly off, but you'll be able to find it. "Maker's Schedule, Manager's Schedule" by Paul Graham. And the legendary PG, who we're going to come back to, is a good place to start.


Dropbox Beginning And Y Combinator Experience

The end of SAT Prep Tests (49:12)

But I want to rewind the clock for a second and ask you, why did you stop the SAT online prep company? 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. 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 just harder and harder to make progress on the SAT prep 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 don't know whether it was because I felt like I was pedaling harder but not getting anywhere, but over time it took a lot more willpower to work on it. And so I found myself procrastinating with all these side projects. And 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 concern to things that are more worthwhile. But then I was worried because I'm like, "Oh my God, I'm so unproductive and I'm wallowing in this guilt." I was raised Catholic so this Catholic guilt of, "I'm not working hard enough, this company is not successful enough..." And it's 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 started working on this poker bot that started and it played with real money. I got past the security on the poker client, this is 2006. So I figured out how to make all that work and then watch 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 totally false. But I was possessed. Were you winning? Was Frankenstein's monster winning? 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." But it was scaring my family because I was living in Boston, but then we have a little summer place in New Hampshire. And 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 three monitors and all these computers. And this is like a little cottage on a pond. It's not set up to be mission control. So I'm putting monitors on the stove and my parents are like, "What are you doing?" They were kind of used to me having all these side projects, so they're just like, "I hope it's not illegal." Unfortunately, that side project had to stop because of that. In the fall of 2006, it went from borderline to very illegal to do online poker. So that project ended. So what's that about?


Side-projects (53:00)

What I took from that was like, "Well, first, 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 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 sort 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 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 back up the SAT prep company, kind of all of our files, to a server. And then eventually I was like, "All right, well, I want to--" I graduated from college. It was about 2006, late 2006. A lot of my friends had lived in New York, and they were 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 ten hours. Ten hours should be enough time to do what I need to do." You know, all 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. So-- - Problem, yeah. - Yeah, back to self-flagellation. I'm like, "Ugh, 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. Like, 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 it 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 opened up the editor and started writing some code in Python that basically was this seed that sprouted into Dropbox. And I was just totally possessed with that problem. Because I'm an engineer by upbringing. My favorite classes at school, other than some of the stuff we've talked about, are algorithms, distributed systems. And I found myself at a crossroads where I'm like, "I love standardized tests as much as any human possibly can, I guess." But a couple things happened. So, one is I paused and I'm like, "Okay, I'm working on this company. I'm kind of burning out." Part of why is because I thought about, "Even if all of my dreams come true and everything we hope for happens with this SAT prep company, then I'm like, 'Then what?'" And I'm like, "King of SAT prep." Right. 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 cardboard crown." 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 PokerBot, but then even more so with Dropbox. So sometimes it's hard -- like, 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.


Y Combinator and Paul Graham. (57:27)

Mm-hmm. So I want to bring this back to the dot, dot, dot that I left after Paul Graham. And we can certainly go in any possible direction you want to take it. But for people who don't know Paul Graham, maybe you could describe Paul Graham. Certainly as close to a demigod as one can probably get among many, many young entrepreneurs and older entrepreneurs in Silicon Valley. Who is Paul Graham? What is Y Combinator? And can you describe your first meeting with Paul Graham? Yes. So Paul Graham is best known as one of the founders of Y Combinator, 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 Y Combinator, he had written -- he was an entrepreneur himself. So he started a company called ViaWeb 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 it was very early in the conversation around using Bayesian methods, using this kind of math to do 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 I -- 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 of 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 -- Wait, hold on. Hold on. Pause. Why didn't the virtual meeting go well? Well, we didn't really virtually meet. It was just sort of like -- it was like a college admissions thing. It's open application. Anybody who wants to submit an application kit for the Summer Founders Program, which basically it was like the same thing as Y Combinator. You get a little bit of money and they all come together. It was sort of Y Combinator version one. 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 -- So 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 my 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 like a much faster trajectory because of YC. And I'm like, oh, my God, I want something like that. But then I -- so I started thinking about applying for YC with Dropbox. And one of the good 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 had just started this news site called Hacker News, which is kind of like Reddit for startup news. And I'm like, what is -- and I thought -- 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 on Hacker News, maybe I can get in front of the dean of admissions here, 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 Guerrilla Marketing, which is like how do you get attention and users for your product if you have no -- Yeah, it's like Jay Conrad Levinson or something like that. Something like that. It's like how do you do that when you have no money? And so there are all these -- so the tactic of putting a video on Hacker News or creating a viral video is -- that was a seed that was planted by reading Guerrilla 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 ship 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.


Persistence and video in raising interest for Dropbox. (01:02:54)

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 long time to be on the top of Hacker News. That can't happen anymore because -- for a bunch of reasons. But it was like -- I was pretty happy about that. And then I'm like, okay, this is -- so far the plan seems to be working. I'm just like keep hitting refresh on my inbox. I'm like maybe -- I wonder if Paul has seen it. And then lo and behold, I get an email from Paul Graham saying like, hey, it looks pretty cool, but you need a co-founder. Because they did -- 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 problem -- 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 like, hey, I know you're not dating anyone, but you need to get married by me. And so hilarity ensued. But then I was -- I flew out to San Francisco. I'm like 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. And so -- but I found another friend -- 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. My flight -- it's a Tuesday at like 1 p.m. My flight back to Boston leaves at like 10 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 like pitch Paul. Maybe that would work. I get to Zipcar. I like fly down 101. And like the plan was like 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 like knock on -- 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 to show you something I'm working on. And he's like, nope, I'm busy. And I'm like, okay, look, I can almost see your screen. I know you're just like reading Hacker News right now. I'm actually busy. 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 talk 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 is 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 -- it'll be fine. So I go back in there and it's like detonation. It's like I said, 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 randos like you don't just like show up here and bother us. It's like, no, please leave. And so I'm like, okay, thanks, Jessica. Thanks, Paul. I'm like, ooh, like my friend, that's -- I'm like, this is not going to be good. I'm like, this is a rough return to San Francisco. So needless to say, the co-founder situation did not work out. You were like, Paul's thinking about it. Let me get back to you. I did meet with the dean of admissions. He just thinks I'm an asshole. So -- I think he's coming around. Let me get back to you. That was a tough plane ride home. But it's good training. This is like the new normal if you're starting a company.


First meeting with Arash after the failed first YC interview. (01:07:39)

Let me just hit pause for one second. What were you saying to yourself on the way back? Like what was the self-talk on the plane ride back? I was like, I have -- I could not have like effed this up any worse if I had tried. Because like now I don't have a co-founder and I'm like I might have been able to get in if I just like hadn't like maximally pissed off Paul. Anyway, now I have no co-founder, no YC and probably no company and I have like two weeks left to like resolve this. Or maybe a week left to resolve them. But anyway, not a lot of time. So it was bad. Yeah, I was like I don't really see how this all kind of lives happily ever after either. So then what happened? So then -- but my kind of shaking the trees in San Francisco did help. So I met -- it turned out I met a guy named Kyle, Kyle Voigt, who I had met at the MIT Entrepreneurs Club. So he's an MIT student. He dropped out. He had just dropped out to do Justin TV, which became Twitch. And then Kyle then later started Cruise, which did great. So Kyle has done well. And then I was complaining to Kyle. I'm like, hey, Kyle, I need a co-founder. Is there anyone you'd recommend? And he recommended me to -- it turned out that Kyle and Arash were floor mates at East Campus at MIT. And so he's like, oh, you should talk to Arash. And then a day or two later I got an email from Arash saying, hey -- he was like a senior undergrad at MIT, a computer science student. And he was like, hey, I got this email from Arash and said, hey, I saw your video on Hacker News and Kyle said you were looking for a co-founder. Maybe we should talk. And then it was kind of insane. We met in the student center. Maybe we got coffee one more time. And then he drops out of school. He's like a senior. He drops out with a semester left. I was thinking this is going to be a process. I'm going to have to talk to his parents and reassure them. But no, we hang out for two hours and then the two of us commit to spending most of our waking lives together for the foreseeable future. I don't think either of us really understood that at the time. Fortunately it all has worked out great. But against all odds, so Arash and I team up. I think Paul forgot about his meeting with me or didn't put the two together. So we did our interview and we got into YC. And it was funny because we were doing the YC interview. We're milling around waiting for – we go down in the morning. We go get lunch. We come back to the car. Our car got broken into and our laptops got stolen. Oh, God. But fortunately all of our stuff was on Dropbox. So we were like patient zero for all this. And then we got the happy phone call from Paul saying, hey, we want to fund you guys. I mean, I don't know. It was nuts.


When did Drew get along with Paul Graham? (01:11:04)

So I don't know if this has changed, but for some period of time, I think it's probably still the case, but you could correct me if I'm wrong. I mean, Dropbox was far and away the most successful investment that Y Combinator had ever made. Certainly, Dropbox has done incredibly well. At what point did you go to Paul's office, knock, knock, "Hey, Paul," in brackets, "Now we're friends"? By any chance do you remember when I came in during Tuesday, on a Tuesday not too long ago, did you ever bring that up with him or did he learn about it through some other means? I like to remind him about it every year or two. I mean, first, he's like totally embarrassed. He didn't put any of these things together. He didn't know. He didn't remember it. He's like, "I was so awful at this half." So mostly, it's just they both, Paul and Jessica, turn bright red and they don't like to talk about it, which is why I like to keep poking at it every now and then. It's all good. I would have done this thing for him. Well, he did tell you I'm busy, right?


Dropbox Name & Trademark Challenges And Mental Health

The story behind the Dropbox name and how they got the domain. (01:12:21)

Yeah, I was super obnoxious. Was Dropbox the original name of the company? Yeah. It was. Wow. So just from day one, you had the name that stuck for you. No, but getting the domain, it was getdropbox.com. Getting the dropbox.com domain name was, oh my God, that was a journey. So there was a, I don't know, I'm like starting to shake a little bit going, I don't know how illuminating this story is, but it didn't – No, let's talk about it because people run into this stuff. I'm sure we can pull some lessons from it. Yeah. So I – I remember getdropbox. Yeah. So Arash and I fell in love. So the name Dropbox, actually, the behind the music version, the story behind the name is also probably unintuitive or not what you'd expect. So you asked what was I like in high school, and the answer is basically he's a huge nerd who likes computer games, and that's true. One of the things we would do is we'd all bring our – we would like – a bunch of friends and I would bring our computers to someone's house and we'd play games. And so back in the day, these things were called LAN parties. They are about as cool as they sound, and you all show up and play till sunrise and so on. But you bring a bunch of people together and often someone doesn't have the right maps or the right patch or the right whatever, and so we had a convention.


land partiers? (01:14:00)

Like you just create a folder called your Dropbox that's shared and writable by anyone, and that's how we would exchange files so that people could play games. And then it's – I remember this. It was like Christmas 2006. I'm trying to come up with a name for Dropbox. I didn't have a name then. The initial name, I had like some – the name before – I was busy Photoshopping a logo. The initial iteration of it was folder anywhere, which – Catchy, catchy. Yes, which just was – which was probably the first indication that I had a brilliant future in marketing and talent for this. And then – so I'm like in Photoshop trying to make a logo for folder anywhere, and I'm like – of course, probably the logo is like a literal folder or something, like totally inane. And then I start – and I'm like – and I – believe it or not, folderanywhere.com was actually available, so I was the proud owner of folderanywhere.com. Then I did a search, and I found – there's a company called Files Anywhere, and I was like, no. Like, I can't – now I can't name it folderanywhere. And so I'm sort of – I'm on aim talking to one of my friends from high school, and I'm like, God, I don't know what to call this thing. You know, folderanywhere is taken. Like, maybe I should just – you know, maybe I should call it Dropbox, like from the – you know, from high school, from land parties. And he's like, okay, whatever. And then – and then at Dropbox.com, not available, so I got getdropbox.com. But then – so we just lived with getdropbox.com for a while. I tried to – you can sometimes look up who owns a domain and contact them, and so I actually did. I managed to give the guy a call, and I'm like, hey, dropbox.com, you know, are you using it? And the guy was like, yes, I'm using it for a project. I'm like, okay, well, do you have any interest in, like, selling it or, you know, coming up with some kind of arrangement? He's like, no. I'm like, okay, cool. So that's February 2007. And then we get distracted with the whole getting into YC, finding a co-founder, all that, doing YC. And then I land, and then we moved to San Francisco in September, and I'm like, we really need to get this domain name. And unfortunately, Arash and I had totally fallen in love with it, so we weren't really – we kind of only had one plan. By the way, that's called a great negotiating position. Yeah, awesome. It worked about as well as you'd expect. So I'm like, well, since we finished Zipcar and show up at someone's house, it worked so well the first time, we're going to do it again. So it turned out the guy lived in Pleasanton, and he was an entrepreneur. Here's someone who's nearby who should be sympathetic to our cause, at least to some extent. And I call him, and I'm like, how's that project going? Because there's obviously no project. And he's just kind of being difficult. And so I'm like, okay, God damn it. So we get off the phone, and I'm like, all right, Arash, let's just show up at this guy's house. Let's just see what happens. So I jump in another Zipcar. We go to the corner store and get their most expensive bottle of $20 champagne we could get. Get in the Zipcar and go to his house. And it's like 9 at night, so this seemed like a good idea at the time. So we show up, and then he was kind of shocked, kind of amused, like lets us in. We start talking. We're like, hey, look, we're pretty serious about this thing we're doing. If it's true that you're not actually doing anything with the domain, help us understand what you're trying to accomplish. Not in a obnoxious way, but at least consider this alternative where we use Dropbox.com. We've got some really good folks who are excited about this and involved, whether it's Ycomdator. We've just gotten funding from Sequoia, our first venture capital investor, who's one of the best in the world. So we're like, Sequoia investing. Are you told in that? Yeah. It's really building up our leverage here. This would be called hemorrhaging leverage. At the same time, the frameworks don't completely account for everything. Sure. Because if you don't actually help them understand why they should be interested, and you hold all your cards to the vest, then nothing happens. And that's what we've experienced over the last seven months. So at least sketch out a case that a reasonable person would look at and be interested in. And then he's like, "Cool. It's interesting. I've got to talk to a friend. Why don't we touch base soon?" And I'm like, "Great." It was like a Friday night, I think. And I'm like, "We'll be back on Monday." And we're on the ride back going over the Bay Bridge, and I'm like, "Holy shit. We might actually be able to get this thing. This guy's been impenetrable and so difficult. We're both kind of in awe. This is such a positive thing." So we go back on Monday, and he's just like, "Yep. Thought about it. Not interested. Thanks. Bye." And we're like, "Are you kidding? Is this for real?" I'm like, "Where's this going to go? Are you going to bequeath this domain to your children? What the hell?" But he was just like, "Totally wouldn't budge." And so that was a much sadder drive back. So then this guy... And then there's just kind of nothing for a couple years, or for a year. And then we launched Dropbox publicly, and then all these confused people start going to Dropbox.com and presumably start trying to get into the beta. So this is later in the year. So he starts getting all these emails from people, I think probably March 2008, who were looking to get into the Dropbox beta. And then he does... God, and I'll end the story in a reasonable amount of time. So then he kind of goes dark. He puts a privacy shield up on the domain, then puts up an AdWords landing page. So like Dropbox.com, it went from a GoDaddy parking page to a Google AdSense for domains page, which was a problem. Because then we're like, "Oh my God, now this guy is totally cashing in." It's basically... You go to Dropbox.com, it was basically AdWords for all of our competitors. Oh God. And so I'm just thinking of like, "What the hell are we going to do about this?" Our investors think we're idiots for not changing the name. We're doing all these pointless branding exercises that did not go well to try to find an alternate name. So I'm just like, "Oh my God, what are we going to do?" And the answer was, "Read the federal copyright code and trademark code." And I became kind of an expert in cyber trademark law. I got an armchair expert in this stuff. And it turns out you can't just get a domain from someone for no reason.


Trademark challenges. (01:22:08)

You can't just be like, "Oh, you're not using it, so therefore it's mine anymore." You can be like, "Oh, you're not using that land. Give it to me." Right. But it is also illegal for someone to intentionally confuse your customers. So I can't just say that we're... I can't sell paper towel or towel... Or I can't sell Kleenex with three E's to confuse people or whatever. Intentionally confusing consumers is a problem. And we had another whole odyssey trying to get the Dropbox trademark, which that's not as interesting. But I'm like, "We had a problem. We didn't actually have the registered trademark either." But he was now making money from infringing on our common law trademark rights. And so I'm working with this crazy trademark and domain attorney. And so we sue him for trademark infringement. And so that got his attention, which we would not have done. We weren't just trying to push him around. He was trying to profit off of confusing our customers. So we got on our high horse after that. And that was a comical whole experience. But eventually he's like, "Okay, okay, okay. There's no point to have this lawsuit. I'll sell you guys the domain." I'm like, "Okay, well, we can offer you stock or cash." He's like, "I'll just take cash." So we paid him 300 grand, got the domain, lived. Sending that first email from Dropbox.com to Paul and Jessica was a huge triumph. We offered him stock at that seed round. It would be worth multiple hundreds of millions of dollars to them. I think what you can take away from this is there's just no manual for that. You've got to wing it. There are a lot of things that are the equivalent. Even today, I'm just getting in the Zipcar with a bottle of champagne and hoping for the best. Sometimes you'll get really good cards. Sometimes you'll get really bad cards. But you've just got to roll with it. So between finding a co-founder and getting the domain, each of those are definitely memorable points along the journey. We were chatting a bit before we started recording about the psychological aspects of, say, prepping for starting a company. I want to tie that to a company you mentioned earlier, which is Reddit. You mentioned that Hacker News is Reddit for the computer science/hacker subset. I remember having Alexis, the co-founder, on this podcast. He told me about meeting really early on with an executive at Yahoo. They were really excited. They went in and they shared their numbers. The executive said something along the lines of, "Oh my god, you're just a rounding error for Yahoo." It was so insulting that Alexis took "You are a rounding error," and put it on the wall in the office to motivate. But that is one of several different responses that are possible. There are certainly people who would be crushed by that. It could be the end. I don't remember exactly where this quote is from, but I want to talk about when this came out and what the self-talk was.


Early Dropbox feedback and hate. (01:26:01)

There's an article being written about Dropbox. I think the quote was, "Fortunately, the Dropbox founders are too stupid to know everyone's already tried this." When did that happen, and how did you and anyone else involved respond to it? That was very early. I would say it was probably within the first year. I think even back to that first video that I put on Hacker News, actually a lot of the commentary was positive. People were like, "I would use something like this. It's good." That was really encouraging. On the one hand, half the peanut gallery is saying that. The other half is saying, "Listing all these reasons why it's been tried before and won't work." Then even if it does work, like Microsoft, Google, everybody's going to kill us. Here's why it's never been a business, and here are all these other ones that have never succeeded. The thing is, I agreed with them. I was like, "Yeah, you're probably right." I don't really see how we survive in 2007. I don't see how we make it through to Mount Doom. That's our little plucky band of the two of us. Invariably, every investor we talked to would raise similar concerns, so the feedback was all pretty negative. It's easy to say, "Oh, just ignore it all," but you have to be balanced. On the one hand, we did get encouraging feedback in the beginning. People were like, "Drop this. It's cool. I will use this. It sounds great." I knew that I needed it. I wasn't trying to create a billion-dollar company. I was trying to just solve a problem. I think setting your sights low in the beginning, ironically, can be helpful, because you're not putting so much pressure on yourself. I was just like, "Look, if I build a cool thing, this is just another side project and a number of side projects. Let me not suffocate it by putting all these crazy expectations on it." I think that's pretty important. Then people were like, "When did you know it was a success?" It was like the goalposts for success kept successively moving back. Even just having a video was a big milestone and launching a private beta was a big milestone. There were a bunch of milestones. It was sort of a continuous process more than, "Oh, it was just one moment in time." But, yeah, there were people who had very good arguments about why this wasn't going to be successful. That's why I think you have to have both thick skin and thin skin. You have to get that balance right, because if you just ignore all of the feedback and dismiss it all, then you're probably going to have some kind of blind spot, and you're going to miss some important information. Just because they came to that conclusion doesn't mean that their assumptions were all correct. That's why you also need to have enough thick skin to know when to be a little bit dismissive or not listen to everything. Part of what helps with that is having conviction, and conviction that comes from being able to think from first principles. Pay less attention to the outputs of people's conclusions as much as the inputs into those conclusions. What does that mean? People said that, "Okay, Dropbox is not going to be successful because people have tried it a million times." That is true. That's factually true. You can't debate that. But that would have been true for mobile. Every mobile thing before the iPhone or every mobile software company, every app was a total failure. Before the iPhone, world changes. Suddenly, it's the right time. If you study history of technology or history of business, you realize that argument is not in and of itself causal. What you want to answer is, "Why is that incorrect?" It's like, "Well, actually, there are a lot of good ideas that are bad ideas for a while because the timing is wrong, but then the timing becomes right because of some discontinuity in tech." What's like the innovator's dilemma or others will illustrate that. That's why it's important to build these mental models because you were like, "All right, this is my framework for how the world works, and I keep refining it." What these people are missing the key conclusion from that. That just because something has failed before doesn't mean it will always fail in the future. It can still fail, but that kind of conviction came from an understanding or a belief in a worldview and framework of, "Here's how I think business works," or, "Here's how to think about an idea like ours." But that said, I think there's a how you receive advice and how do you develop first principles thinking, which we talked about. That doesn't make it feel any better when people are like, "Your idea sucks and you're going to fail." Or even worse than that, like, "You are stupid."


Managing your psychology. (01:31:29)

It's really super ad hominem. Right. First of all, I think you have to have a sense of this is normal. Just don't take it too personally. You want to receive the feedback and try to extract the kernel that's useful from it, but not feel obligated to accept the whole thing. I think more broadly, you just have to, whether it's getting criticism or just a lot of the thing. I think one of the harder things about running the company in general was I just remember being in the beginning being like, "Oh my God, Sequoia has decided to invest in our company." Against the odds, now Sequoia has decided to invest. They're writing us a check for a million dollars. I hope they realize that I haven't really done this before. And like, "Oh God, that million dollar, it's great to kind of cash that check, but oh man, they're going to be looking for that money back at some point. What are we going to do?" There were probably a lot of things going on in my head at the time. And then like, "Oh my God, I've never really built a successful company before. I've never managed people really. The idea of Dropbox being a 100 person company is terrifying. This treadmill is just going to go faster and faster until I'm violently thrown off of it. How am I going to deal with that?" And a lot of me also felt like, "Okay, well I'll just build the company until it's successful enough or makes enough money where I just don't have to worry about money anymore." And then as soon as I get to that, I don't know, this was just some kind of theory. I'm like, "All right, as soon as I get to that level of success, I'll just stop just so I don't screw it up." But then interestingly, that goalpost kept moving back and moving back and moving back. It's never really been about the money, but you can read in the Y Combinator application, that's now public, where you put that out there. If I had a million dollars after taxes for six months of work, I'd consider that a pretty good deal. But more on just what do you do when you're like, "Oh my God, this is pretty uncomfortable. I've never done anything like this before. I might screw it up." So your instinct will be to run away from that feeling, and what you need to learn to do is run towards it. Because that's just going to keep happening and keep happening. I'm like, "We're going to show up at this guy's house. Maybe we'll get arrested, but we're going to do it." I don't think that's the best example. There are just so many things where you've just got to figure it out and keep going. One of the great things that Ben wrote in his book, The Hard Thing About Hard Things, is the hardest part of being a CEO is managing your psychology. I didn't really know what that meant at the time. I think I have a much better sense now. So I think the first thing is being comfortable with being uncomfortable. You think about principles, like Ray Dalio's book, he's like, "Pain plus reflection equals progress." People love the progress part, or they love growth, but they don't love the pain part, and they don't bother to do the reflection part. So understanding that that is—and zooming out and understanding it, depersonalize it. It's not really you. This is just the process of growth. It will be painful. Think of your journey as more of an adventure rather than a final exam where you have to get everything right and you only got one shot.


Taking care of yourself. (01:35:15)

I think that's pretty important. And then second is, all right, you have to—now everybody likes the idea of growth and pushing yourself, but you also have to take care of yourself. You have to find ways to metabolize stress and avoid burnout. And for some reason, people just—they just use the one tool of pushing themselves harder, and then they break. And you wouldn't do that to your car, you wouldn't do that with a musical instrument, so why would you do that to yourself? Just to pause for a second, I recall very distinctly, every time we've stayed at the same hotel or been at the same event and I've gone to the gym, I've almost always seen you in the gym. It seems like you have, just as a component of that, a physical practice to care for the machine, so to speak. Yeah, I wouldn't say I'm the best athlete by any stretch, but it's really important. You have to do enough so that you don't break down. And you've got to figure out what that is for you. And I know that's something you really care about, and the advice you have to offer your readers is going to be much better than whatever advice I have. But you need to do something, some kind of routine, and stick to it. But just the basics of—I think some of the dumbest advice that people get is not sleeping or wearing—or just pursuing this idea that successful people somehow work 70, 80-hour weeks, and that's the norm. There are a number of problems with that. First, it's usually not true. It's usually more of an indication of the person's either lack of awareness about where they're spending their time or lack of effectiveness if their only tool in the shed is work more hours. Because just think about that. That has a ceiling in terms of how much of an advantage that can give you. Like, yes, you want to work hard, but if your only advantage is being able to work 20 percent more hours than someone who's merely very committed, then you're not going to have outsized results. Anyway, I think this meme that successful people work 100-hour weeks or something is both false and super harmful. The most successful people I know actually work—I mean, they have crunch times where they're super busy, but they otherwise have a work week that looks more normal than not. And so that was something I didn't realize when I was starting out. But the basics of sleep, eating well, self-care, exercise, putting it on your calendar, not just wishful thinking and hoping it'll sort of happen in the spare moments. Like, if you can't see these things on your—if you can't see your priorities on your calendar, if you can't see your gym time on the calendar, it doesn't exist. Totally. And so—and then I think self-awareness—there's probably a lot more we could talk about how to metabolize stress and avoid burnout. But I think having—taking care of the basics, having a good foundation and setting healthy boundaries is pretty important, and having a sustainable workload.


Abstract Conversations And Living Your Truth

Why coaching has been helpful. (01:38:35)

So self-awareness is pretty important, and being willing to shine a hard light on yourself and embracing that. So for me, coaching has been super helpful. Coaching meaning you have an executive coach or— Yeah. I've had different ones over time. And really, I go through that experience, and I'll give this a shot. Some of my friends have spoken positively about it. But it's a little—I remember my first coaching experience, and they do the 360, and then you sit down and you do your review of your results. So sorry to pause. Yeah. And then I'll give you a shot. So I'll give you a shot. Yeah. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot.


So-noymanet [phonetic44:53] (smoke-karta44:55)? (01:40:40)

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At what time yung? (01:43:41)

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One Megan Monologue (oh and some monsters in the background) (01:44:09)

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Living Your Truth: Check In With Those That Matter & Drop The Rest (01:44:59)

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Ready To Rebuild Relationships That Matter & Healthily Let Go? (01:45:54)

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Career Advice And Final Thoughts

A money-saving travel tip and expedient tracking software. (01:47:35)

So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So I'll give you a shot. Okay. So this idea of life unfolding infinitely in front of you is actually not really true. And so it's really important to not just make every day count, but also understand that think of life more as an adventure or a story more than how you think about life when you're graduating college, which is life up until you graduate college is just like a series of checking off boxes and getting ready for stuff and performing. And all of your worldly achievements are averaged into a GPA. And so every mistake brings that number down and it's something you have to obsess over. And then college graduation is the first day where that's not really true anymore. You don't really have a GPA anymore. You're not an average of all your successes and failures. You should change your mindset to life and also just think of it more. Just making a story that's interesting, not trying to be perfect, because I think it's a trap that a lot of people fall into.


One of the biggest traps college graduates fall into. (01:49:25)

So anyway, when I thought about if you were to play everything over again 100 times, who knows what would happen. But if I could just hand back a cheat sheet, that's what I would put on it. That's what you'd put on it. Tennis ball, circle, and the number 30,000. Well, Drew, I know you have a very, very busy time ahead of you and I'm sure today is no exception. So I want to let you get back to your day. Do you have any closing comments, asks, suggestions, or anything else for people who are listening to this? Any parting comments before we wrap up?


Final thoughts. (01:50:05)

Let's see. So I think don't forget to have fun. And I think at the end of it, there's an obsession with avoiding failure. And if you think of it more as the failures aren't really that important, it's more how you respond. What you want to do is write an interesting story, not a perfect story. Yes. Yes. And the first thing they do with, well, I shouldn't say this so definitively, but it's like a lot of screenwriters who are experienced will say you have to create characters, the protagonist who on some level the audience really cares about and then torture them. And then they come out the other side. That is one of the recipes for writing a successful screenplay. And if you're part of the human condition, it seems like that is going to be a component. One way or the other. Well, Drew, thank you so much for the time. I always enjoy chatting and hopefully we get to hang again in person sometime soon. But I appreciate you carving out as much time as you did to share your stories with everybody. For sure. Well, thanks Tim. It was a lot of fun. And for everybody listening, we will have links to all of the books mentioned, everything else that Drew may send our way as well in terms of resources, all the things that we discussed, Hacker News, et cetera, in the show notes, which you can find as always at Tim.blog/podcast with all the other episodes. And until next time, thank you for listening.


Five Bullet Friday [Obsolete] (01:51:47)

Hey guys, this is Tim again. Just a few more things before you take off. Number one, this is Five Bullet Friday. Do you want to get a short email from me? Would you enjoy getting a short email from me every Friday that provides a little morsel of fun before the weekend? And Five Bullet Friday is a very short email where I share the coolest things I've found or that I've been pondering over the week. That could include favorite new albums that I've discovered. It could include gizmos and gadgets and all sorts of weird shit that I've somehow dug up in the world of the esoteric as I do. It could include favorite articles that I've read and that I've shared with my close friends, for instance. And it's very short. It's just a little tiny bite of goodness before you head off for the weekend. So if you want to receive that, check it out, just go to 4hourworkweek.com. That's 4hourworkweek.com all spelled out. And just drop in your email and you will get the very next one. And if you sign up, I hope you enjoy it.


WordPress.com [Obsolete] (01:52:52)

This episode is brought to you by WordPress.com. I love WordPress. I have used it for so many years. It's my go-to platform for blogging and creating websites. I use WordPress.com for everything every day. My site, tim.blog, is built on it. The websites for my books, including Tools of Titans, Tribe of Mentors, it's all on WordPress.com. And the founder, Matt Mullenweg, one of my close friends, has appeared on this show many times. Just search Matt Mullenweg to Keila Farris for quite an exciting time. Whether you're looking to create a personal blog, a business site, or both, you can make a really big impact right out of the box when you build on WordPress.com. And you'll be in good company. It's used by The New Yorker, Jay-Z, Beyonce, FiveThirtyEight, TechCrunch, TED, CNN, and Time just to name a handful. And one of my friends at Google, she'll remain nameless, has told me that WordPress.com offers the "best out of the box SEO imaginable." And it's one of the many reasons that nearly 30% of the internet is run on WordPress. You do not need experience or to hire someone. That's perhaps the best part. WordPress.com guides you through the entire experience. They have hundreds of designs and templates that you can use. And it's easy to get started. There's no need to worry about security, upgrades, hosting, any of that. They offer 24/7 support. And they're very, very responsive to your questions. They go right back to you. And this allows you to create the highest quality with the least amount of headache and friction. So if you're building a website, period, and my friends come to me and ask what I use, what I recommend they use, the answer is WordPress.com. So check it out. If you want to get started today, learn more with a 15% discount off any new plan, go to WordPress.com/Tim to create your website and find the plan that's right for you. So learn more. Take a look. WordPress.com/Tim for 15% off your brand new website.


Obsolete References

99designs [Obsolete] (01:54:54)

Check it out. This episode is brought to you by 99 Designs. Whether you need a logo, custom website, app, book cover, or anything else, 99 Designs was created to make great design accessible to everyone, that's you, and to make the process as easy as possible. I've used 99 Designs for years now. I've used them for book covers, some mock-ups for the 4-hour body, which went on to become the number one New York Times bestseller, illustrations of all different types for the multi-volume The Tao of Seneca, which you can check out, and other graphic design projects for a long time now. And I've been very impressed by the quality of their designers and illustrators. And you don't have to take my word for it. You should check out some of my projects at 99designs.com/Tim. I really encourage you to take a look, because you will be impressed. 99designs.com/Tim. 99 Designs has freelance experts in more than 90 design categories. And their platform lets you work directly with one designer that you choose, if you like their stuff, which is what I did for The Tao of Seneca. Or you can get concepts from multiple designers and then pick your favorite. So whether you're starting a business or just looking for extra design help, resources, et cetera, 99 Designs has a solution. Right now, you guys, my listeners, can receive a free $99 upgrade on your first design. To check out your first free upgrade, please visit 99designs.com/Tim and click the link on the landing page. You can also find there samples of projects from you guys, listeners, who have used 99 Designs for logos, apps, even product packaging. So check it out. 99designs.com/Tim. 1 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16


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