#334: Drew Houston — The Billionaire Founder of Dropbox

"Write an interesting story, not a perfect story." — Drew Houston Drew Houston (@DrewHouston https://twitter.com/drewhouston) is co-founder and CEO of Dropbox https://www.dropbox.com/. 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. Drew received his bachelor's degree in Electrical Engineering and Computer Science from MIT in 2006. After graduating, he turned his frustration with carrying USB drives and emailing files to himself into a demo for what became Dropbox. Today Dropbox is one of the world's leading business collaboration platforms, with 11 million paying subscribers and 1,800 employees across 12 global offices. Enjoy! This podcast is brought to you by 99designs http://99designs.com/tim, the global creative platform that makes it easy for designers and clients to work together to create designs they love. 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Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:01Speaker 00

  At this altitude, I can run flat out for a half mile before my hands start shaking. Can I ask you a personal question?

• 0:08Speaker 01

  No, we're just seeing an appropriate time.

• 0:12Speaker 00

  I'm a cybernetic organism, living tissue over metal endoskeleton.

• 0:23Tim Ferriss?

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• 1:04Tim Ferriss?

  subscription purchase. So learn more, check it out, go to drinkag1.com/tim. That's drink A G one, the number one, drinkag1.com/tim. Last time, drinkag1.com/tim. Check it out.

• 1:24Tim Ferriss?

  Hello, boys and girls. 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, at Drew Houston on Twitter and elsewhere. He's the co-founder and CEO of Dropbox. Since founding the company in 2007 with Arash Fardozzi, 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.

• 2:07Tim Ferriss?

  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.

• 2:28Speaker 03

  Thank you.

• 2:29Tim Ferriss?

  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, this is a fun opportunity for me to dig in. So I appreciate you taking the time.

• 2:51Speaker 03

  Awesome. Yeah, me too. It's, uh, it's, it's great to be here.

• 2:54Tim Ferriss?

  And, uh, 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?

• 3:17Speaker 03

  So yeah, going, going way back. Um, well, I, first I was, uh, I was definitely that kid who was on computers. So we, my parents, I remember, uh, just like, 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. Um, I guess still do. Um, and, um, so for sure, I was, I was super interested in, in computers and technology and, um, started out by, by playing computer or video games, basically. That was like the first interest. And then I wanted to make my own computer games. Um, I thought that my career was going to be, uh,

• 4:02Speaker 03

  starting a computer game company. And I thought that was, uh, that there would be nothing better than that. Um, and, uh, so I, but I, but I was that kid. So I learned programming at an early age. Um, I grew up in, uh, just outside of Boston. So I grew up in New England. Um, and, uh, and then on my way to MIT, I, I really liked math, science. Um, so, uh, kind of out of central casting in terms of being a computer science student. Um, and then, yeah, and then, then. I got, 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.

• 4:43Speaker 03

  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, uh, but programming is even better. Anyway, so, um, so, uh, so, but in, in, in middle school and in high school, I ended up getting, um, a bunch of programming internships or, or, or summer jobs, um, at what were, at startups, basically. One of them was remote, uh, most of them were local, but then that got me on a path of, of starting companies and, and being involved in startups.

• 5:24Speaker 03

  But, um, I would say those are probably the, um, the biggest, when it, when it, when it comes to Dropbox and everything that kind of followed after the, from my childhood, it was a happy childhood, lots of, um, uh, I'd say it was still pretty balanced, but I, I did, I, I like, programming and engineering was for sure my first, my first love.

• 5:46Tim Ferriss?

  And were you a shy kid, an extroverted kid, uh, played sports, kind of kept to yourself at recess? What was, what would somebody looking in from the outside, like, how would your, how would your third grade teacher describe you in that capacity?

• 6:02Speaker 03

  Yeah, I think somewhere in the middle. So I, I wasn't, um, reclusive, um, I had a really great group of friends. Um, I wasn't captain of the soccer team either. Um, I think I did, I did academic, I did academic decathlon, which is just a fascinating thing that it, it exists. Um, but you know, more of a mathlete than.

• 6:25Tim Ferriss?

  Right, than an athlete.

• 6:28Speaker 03

  An athlete, so, um, but, uh, and I was, I, I, yeah, I was not like.

• 6:35Speaker 03

  A super social, but I had a good group of friends and um and then for sure as I went into college, I became a lot more social and and and just curious about humans and human behavior. But uh but otherwise, I think people like the I would have been known in class um as always doing, I think there were like those superlatives in yearbooks. I think I was like most likely to start a company or.

• 7:03Tim Ferriss?

  They pegged it pretty early.

• 7:06Speaker 03

  Yeah.

• 7:07Tim Ferriss?

  So I was doing homework for this, which I always enjoy doing when it's 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. So I don't I could you place us when that was in your undergrad career and how you chose the books and why you did that?

• 7:41Speaker 03

  Yeah, so I it was about my junior year of 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 the I was maybe 21 and the SAT was changing. I started an online SAT prep company and 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

• 8:26Speaker 03

  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, you know, all those 800 page books that have been printed about it are now obsolete. And who really wants to go to some classroom at eight in the morning on Saturday? Anyway, like 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. And I think we we met in a Chili's and like we're.

• 9:02Speaker 03

  Planning world domination and like figuring out how do you incorporate a company? And so it's a really great introduction to the world of starting companies. And then it was, it also, the more I learned about the mechanics of, 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'd been, I'd worked at startups. But when it came to, but it was kind of, there was a fog beyond just like building the product. And so I was like, all right, we're gonna need, I know like sales and marketing and, and strategy, like these are all things and all I know is I don't know a lot about them.

• 9:47Speaker 03

  So I had the highly scientific method of, I just was like, all right, I'm just gonna go on Amazon, type in sales, buy the top three or four books and just do that for every like category. And then I had a couple of book recommendations from one of the founders of one of the companies where I worked as well. But, but it was great and it was, it was, it was an important combination. So if one was, one was actually, starting the 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 like, read the book, you're like, that's interesting, but then don't use the knowledge. Right. But if you're actually starting a company, then you really have an excuse to internalize and really study the material.

• 10:32Speaker 03

  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, and then reading's gonna be a good way to get me introduced to all these topics. And all of that, maybe the first instance of that was when, you know, I went through my high school and I was, and there were a lot of great books that you read as part of your, you know, high school curriculum. But then I stumbled across a book, Emotional Intelligence by Daniel Goleman.

• 11:07Speaker 03

  And I was like, oh my God, like this is just like, it's nonfiction. But it spelled out something that was, 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'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 business person. And kind of shatter that misconception.

• 11:52Tim Ferriss?

  Do you think that you were open to all these different categories of learning because of the necessity vis a 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 write or rather wear all those hats that kind of drove you into these different categories?

• 12:34Tim Ferriss?

  Or were you intrinsically, using that word quite a bit, but interested in learning more about these different buckets through these different books?

• 12:43Speaker 03

  Well, 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, yeah, it's a big culture flaw 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.

• 13:15Speaker 03

  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 like the stuff is, is actually really interesting. And, but I kept having experiences like that. And 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 like yells louder, lies more, smacks the table harder, I guess that's what makes you a good negotiator. And then this class, like, I mean, those are tactics. But like, the class has these frameworks where like, okay, smart people have thought about this and they've broken

• 13:56Speaker 03

  it down. And you, 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, da, da, da. And so, 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'm, I have to take. And it's a lot more applicable to my daily life. And so I started to, I really appreciated like learning a little bit about a lot of different disciplines and, 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.

• 14:38Tim Ferriss?

  Were there any other books besides emotional intelligence during that period that really had an impact on you?

• 14:46Speaker 03

  Yes. So in that negotiation class, there's a book called Getting the Yes, which is about principled negotiation. And I still think about a lot of those, I still think about and apply a lot of those concepts today. And then some of the, so part of it was just like kind of doing a random walk on Amazon. But I also became friends with the founders of the companies where I worked. And I went during lunch breaks or at other times, I'd go like chase them down and bug them and ask them questions about like, hey, how do you start a company? Like, do you have any book recommendations? Just making that, you know, kind of taking advantage of being the bright eyed, bushy tailed intern

• 15:27Speaker 03

  and shaking down my boss or my mentor, or my, 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

• 15:43Speaker 03

  And what, and it's a big, 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.

• 15:58Tim Ferriss?

  Yeah.

• 15:59Speaker 03

  It's a book on marketing, technology marketing. It's like, how do you, how do technology products make their way from early adopters to the mainstream?

• 16:06Tim Ferriss?

  And have you found yourself revisiting those books? Or were they a point in time during that rooftop Amazon education period?

• 16:18Speaker 03

  I have. I mean, I'd say there are a lot of, you read a lot of books. Not all of them are as good as The Innovator's Dilemma. But then, yeah, it also helps to revisit some of the classics. Innovator's Dilemma is, 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 know, you're reading this book and you sort of get a general sense for things, but you don't, you don't really deeply understand the concepts. And then, coming back five years later, 10 years later, you can really absorb a lot more of the material. So, I do, I read

• 16:59Speaker 03

  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 like, interesting? Or is it that I might need to know something about? Or is it just fun? And if you study it, if I'm like, I need to study this book, then I approach it pretty differently than if it's just like entertainment.

• 17:19Tim Ferriss?

  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.

• 17:50Speaker 03

  Yeah.

• 17:51Tim Ferriss?

  And I think they go together really, really nicely. If you were teaching, say, we're just going to stick on books for a little bit, because I know you read so much. If you were teaching, say, a

• 18:04Tim Ferriss?

  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. If you were to pick, I'm just pulling this out of thin air, but three to five books that would be sort of the core of your reading list, do any come to mind that we that we haven't talked about?

• 18:35Speaker 03

  Yeah, so I for this for the sake of starting or if the subject of the class were starting a company.

• 18:43Tim Ferriss?

  Yeah.

• 18:45Speaker 03

  Or evolving from being an engineer to being a business person. I have a few, I have a handful of books that I really love and the concepts I still 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 back in the, particularly back in the 80s and early 90s. So he, Andy was an engineer, one of the founding engineers and then rose the ranks at Intel and became CEO. So he's led this path. And

• 19:28Speaker 03

  when I read about the, 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, okay, how do you run a team? How do you break down a goal into into sub-goals? How do you, just the one-on-one of running a team and running an organization and a focus on output and results and how do you measure people? And just a lot of things that you, nuts and bolts things that you, challenges that you encounter when you're, 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

• 20:13Speaker 03

  Core of that book is really about, 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, how do you know if you're being effective? What practices, there's a bunch of practices that you can adopt that, 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?

• 20:57Speaker 03

  So The Effective Executive is, it covers a lot of the ground. That's another, 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 others, 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. Right. Which is 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 of favorite books are Poor Charlie's Almanack by Charlie Munger.

• 21:41Speaker 03

  So Charlie Munger is Warren Buffett's longtime business partner. And, 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 the, so it's like, how do you, how do you grow wisdom or grow judgment quickly? Poor Charlie's Almanack is a, is a great example of books.

• 22:24Speaker 03

  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

• 22:40Speaker 03

  He argues that a lot of really wise and effective people develop, or they basically build a catalog of mental models, where, 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. And so, for example, the concept of a batna, like, and leverage, that might be a concept that can be applied in all kinds of different situations. Or comparative advantage from economics, or, and,

• 23:14Speaker 03

  or, you know, 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, and then how do you avoid, how do you particularly avoid terrible decisions? But really, how do you build enough of, get enough of these, he calls it a latticework. 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?

• 23:51Tim Ferriss?

  Yeah, Piersek.

• 23:53Speaker 03

  Yep.

• 23:55Speaker 03

  So you talked about engineers who, like, dismiss, like, all these things that can't be fit into an algorithm, or, or, you know, that don't have some kind of, like, mathematical rigor underpinning them. Zen and the Art of Motorcycle Maintenance is about that, like,

• 24:14Speaker 03

  just that question of, okay, you have, like, this whole rational world, which can explain a bunch of stuff, but then you have the whole aesthetic world, which can't be boiled down to a formula. And they both exist, and they are both useful in different cases, but they don't tend to get along. And so, how do you, like, so what's up with that? And then, it's a really great book about those kind of concepts. And I think developing an appreciation for...

• 24:39Speaker 03

  For both, or developing both your left and right brain, you know, to, to, to use that analogy, I think is really important if you're, 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, and sort of like, and a lot of things like strategy or the engineering are kind of fall 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

• 25:20Speaker 03

  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, to the more rational or like kind of engineering bag of tricks. So I think developing both of those, developing both sides of your brain or developing an appreciation for, for both is really valuable. Maybe one more, so Principles by Ray Dalio, who was, I know was a recent guest. I think he's got really concise and good thoughts for like, all right, how do you sort of approach all the, how do you approach life? So it's, I would include a mix of, of, of different kinds of things.

• 26:03Speaker 03

  I'd have like more instructional books, like more philosophical books, more story and history kind of books.

• 26:10Tim Ferriss?

  Man, I want to take your class.

• 26:13Speaker 03

  Yeah, that's pretty, that's pretty good.

• 26:16Tim Ferriss?

  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, 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. So 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 foreword, I believe, was from Ben Horowitz, who wrote the, another book that you had mentioned, you know, the, what is it? The hard thing about hard things?

• 26:53Speaker 03

  Hard things.

• 26:54Tim Ferriss?

  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. That's 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 Partrali's Almanac is a great book, and I want to underscore something that you said

• 27:38Tim Ferriss?

  somewhat in passing, or 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 fat, the best 60-second mind he's ever met, 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 so I revisit this quote, somebody could find the right version, but it's Munger who says, you know, it's amazing how successful you can become if you just consistently avoid

• 28:21Tim Ferriss?

  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 latticeworks 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, 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

• 29:03Tim Ferriss?

  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?

• 29:22Speaker 03

  Yes, so orig- I think originally, well, yeah, it was, it stood for other people's problems. Um, although I made it a little nicer later, other people's priorities.

• 29:37Speaker 03

  Um, and because I have a vendetta against email, which we can, um, we can, we can dig into. But I, I mean, 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.

• 30:04Tim Ferriss?

  Right.

• 30:05Speaker 03

  But, but then to the OPP thing, I'm like, wait, then what are these things? Like, what am I doing? And then you realize that like, you're just basically checking off items on other people's to-do lists. Where there's, there's, you know, sort of in the abstract, there's nothing wrong with that. And it's important to be helpful and we all are, 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, and your calendar and your email can often reflect that. And, uh, and tying it to another, so one of the most important concepts is focus. Everybody understands like, yeah, yeah, focus.

• 30:50Speaker 03

  And I imagine this is something we'll probably talk more about here.

• 30:54Speaker 03

  But there are so many forces, it, it, well, people love the idea of focus. And, and, and when, it was interesting, just going back to Warren Buffett. So Warren Buffett and Bill Gates did an interview. It's on, I think it's on Netflix, there's like a Warren Buffett documentary, um, which is great. I also recommend, but anyway, they, they, 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, Bill said focus.

• 31:27Speaker 03

  And so if we all, and it's like, seems so obvious, we all know why focus is, is like, we don't need to be told why focus is important. But then, uh, 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. And that's true of your inbox, your inbox will just, is not prioritized, it's just gonna like, You basically get all these requests that are other people's priorities. If you're working within an organization, pretty much everybody will be pulling on you to kind of feed the beast of the organization. And so it becomes very hard to do a few things well. And so, I mean, there's a lot of great things about that book.

• 32:07Speaker 03

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

• 32:29Tim Ferriss?

  So now, the OPP folder, 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?

• 32:56Speaker 03

  Yeah, so the... I think some people would say it's a black hole even when I help. So, I'm not great at responding to these things. So, I mean, it might be... If it's something that's not a priority, then I'll try to respond in days, but sometimes it's weeks, sometimes it's months. Sometimes you'll get a response that's like, "Oh, yeah, it's seven months later." It's like, "Oh, here is... Do you still need this?" But, so, I would... I think it's if it is something from a person you have a relationship with. I would say, and there's probably other factors, but it's like, okay, is this someone who I know and where I personally would be really helpful?

• 33:41Speaker 03

  And they have done their homework, and it's like, I think there's a certain first-pass filters like that. I would say...

• 33:51Speaker 03

  There is no commandment from God that you have to respond to every email you receive. So if it's like a cold email, or if it's like from someone I don't know, or it's like a sales thing, or whatever, then it just goes into the black hole. Or if it's something like, you know, there's a lot of folks who are like, "Hey, I need a mentor," or "How do I raise money?" 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."

• 34:34Speaker 03

  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 just keep that budget of your time constrained to something small.

• 35:03Tim Ferriss?

  Yeah.

• 35:04Speaker 03

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

• 35:18Tim Ferriss?

  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.

• 35:58Speaker 03

  Yeah.

• 36:00Tim Ferriss?

  Which I think is a great commandment or sort of 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. Do you have any other best practices or do's or do-nots when it comes to managing email?

• 36:25Speaker 03

  Yeah.

• 36:26Tim Ferriss?

  Or not using email?

• 36:27Speaker 03

  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 to like 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 like flame wars, but often the best way

• 37:10Speaker 03

  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's 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 and early understanding where your time goes. And it is kind of shocking and hilarious, but really tragic, that we all think we know

• 37:53Speaker 03

  exactly where our time goes, but then when you measure it, you're not usually just like slightly wrong, you're like totally upside down. So this is a really valuable exercise for anyone, but actually like keeping a log of like 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, oh, 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, like, I was spending like no time on those things. I was spending, there was a lot of, yeah, a lot of OPP back then, like, just like responding to, like,

• 38:38Speaker 03

  following up on favors or speaking engagements that didn't really do anything for the company. And there wasn't like a lot of, like, total fat like that, but, but it just might, 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, 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 gonna tend, and then you also want to offset the tendency for, to be in this permanently reactive state, which, whether that's because you're getting emails that

• 39:23Speaker 03

  are other people's requests, or your calendar says one thing. Usually, when you're too, this gets too long, you just try to, 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, you know, hour. And that's not, that's not effective, compared to having, 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, you're gonna, the fires will get dealt with

• 40:06Speaker 03

  first, and that's, that's not a bad thing, or that's like necessary, you can't not put out the fires. But then, the important stuff, the, or I'd say Eisenhower had this

• 40:16Tim Ferriss?

  Exactly.

• 40:17Speaker 03

  concept of important versus urgent.

• 40:18Tim Ferriss?

  Yeah, the matrix, the quadrants, I guess it was for, yeah.

• 40:22Speaker 03

  The two by two, is it important and urgent, like, you're just, and eliminating stuff that's not important, not urgent, but, but really, the biggest prior, crisis of prioritization is like, how do you make sure that you do? 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 like, cut those down as much as possible. Because otherwise, a lot of the fires, if you actually do a root cause analysis. Think about like, why was this fire in the first place? When you kind of climb that ladder a couple of rungs, like, why did this happen? Why did this happen? Or why did this happen because of that? Well, why did that happen because of that?

• 41:05Speaker 03

  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 doing, fighting all these fires and not actually putting them out at their root. So, something I do on that front now is I have a, there's a concept called No Meeting Wednesday, which I think is popular around the valley. Maybe it originated Facebook, I'm not sure. But we've sort of half-heartedly adopted that, and I half-heartedly adopted that for a while. But I remember there was a, I'm like, I really want to do this because there's all this

• 41:47Speaker 03

  planning and like, all these things that are important that, where the cost of me not creating clarity for my team is super high. And I sat down with my assistant at the time and I was like, hey, I need to, like, please don't schedule stuff on Wednesday. Like, it's really, 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, 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.

• 42:28Speaker 03

  I'm like, this is all important, like, but it's not. And, and so...

• 42:36Speaker 03

  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. So otherwise, you just, you lift up your head and you find like six months have passed on some important, quote, "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.

• 43:20Speaker 03

  And one of the concepts from Effective Executive is like, a lot of that stuff only makes pro, that doesn't, 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, great conceptual foundations in Effective Executive about your time and effectiveness, and disambiguating busyness from effectiveness. And then the concept of leverage and high open management, and a focus on output. So those two books have pretty much, conceptually, everything you need, but then implementing it in practice is a lot harder.

• 44:00Tim Ferriss?

  Yeah, we're gonna 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 if 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

• 44:41Tim Ferriss?

  into the jar, then you have a bunch of smaller pebbles, and then you have a pile of sand, 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 scroll on the top and it's nice and neat, but if you put in the sand first, the whole thing falls apart, right? 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. And the time audit, though, as you described, is so important for people to do, because

• 45:25Tim Ferriss?

  very often, even your calendar is not a good reflection of how you in fact spend your time. And if you look at, say, 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 like 30 to 40% off, right? It's not a small difference, and I think the same thing happens with time, really, 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, but for people who really want to also

• 46:09Tim Ferriss?

  get a teaser for what you'll read more about in The Effective Executive, there's an essay, I might be getting it, the headline's slightly off, but you'll be able to find it, Maker's Schedule, Manager's Schedule? Yep. By Paul Graham. And the legendary PG, who we're going to come back to, is a good place to start. But I want to rewind the clock for a second and ask you, why did you stop the SAT online prep company?

• 46:35Speaker 03

  So I started the SAT Prep Company in 2004 and then I went back to school, finished my undergrad and then a couple of things happened. So I was still, I was, after graduation, I started working as an engineer at a network security company and I was still moonlighting on the, on Accolade, the SAT Prep Company. But I found myself in a situation where it was like, it was just like 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 was just, it took more and more willpower to like pedal, or I felt like, I don't know whether it was

• 47:20Speaker 03

  because I felt like I was pedaling harder but not getting anywhere, or one way or another, but over time, it took a lot more willpower to work on it. And so I found myself procrastinating with all these like side projects. And I mean, now I recognize all this as burnout and, and a positive, there aren't a lot of good things about burnout, but sometimes the positive element is to consider your attention to things that are more worthwhile. But then I was worried because I'm like, oh my God, I'm like so unproductive and I'm wallowing in this like guilt. I was raised Catholic, so like this Catholic guilt of like not, you know, I'm not working hard enough, this company's not successful enough, all my da-da-da-da-da, and it's just

• 48:05Speaker 03

  like totally not helpful. But, and so I'm like, oh my God, am I broken? Like, am I not capable of working hard? What's wrong with me? But then I would, like, one good news, I started working on this like poker bot that started, and it played with real money, like I got past the security on the poker client, this is on six. So I figured out how to like make all that work and then watch, it's kind of my Frankenstein moment, as the bot comes to life and starts playing on real poker tables. And so this idea that you can't have poker bots was like totally false. But, and, but I was possessed. It was like...

• 48:45Tim Ferriss?

  Were you winning? Was Frankenstein's monster winning?

• 48:48Speaker 03

  Well, I mean Frankenstein was like not too smart in the beginning. So like there's some... The thing starts moving the mouse and playing the hand, then gets confused because it has there's some like 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.

• 49:16Speaker 03

  But it was scaring my family because I was... I was living in Boston, but then we have a little summer place in New Hampshire. And I was like, my family's like, okay, you know, come up this weekend. We're all gonna be at the lake. And I'm like, okay. And then I get to the lake and I start unpacking my trunk. And I've had like three monitors and like all these computers. And I'm like, I mean, this is like a little cottage on a pond. It's not set up to be like mission control. So I'm like putting monitors on the stove. And my parents are like, what are you doing? They're kind of used to me having all these side projects. So they're just like, I hope it's not illegal, just...

• 49:59Speaker 03

  Unfortunately, that side project had to stop because of that. Like in the fall of 2006, it became like, went from like kind of borderline to like very illegal to do online poker. So that project ended. But so what's that about? What I took from that was like, well, first I'm like, I'm not broken. I'm super capable of working hard. It's just like, I need to find something that I'm really motivated by. And so that was a relief. And then along the way, so I continued to work on the SAT prep thing. But then the kind of the founding story of Dropbox was, well, I had to use...

• 50:41Speaker 03

  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 because... or collaborating with him because we didn't have an office. Well, we bootstrapped the company, so we didn't raise any money. And we didn't have an office. We didn't work out of the same place. And we didn't have servers. We didn't have anything. So we would just like 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 our, the SAT prep company, kind of all of our files to a server.

• 51:21Speaker 03

  And then eventually, I was like, alright, well, I wanna, I graduated from college, it was about 2006, late 2006. A lot of my friends had lived in New York, and they're like, "You gotta come out, it's a lot of fun here, you know, just come out for the weekend." And I'm, I have a dilemma, because I'm like, "Well, I, I need to get some stuff done for my company, but I also wanna go to New York." And I'm like, "Maybe if I take the Chinatown bus, or if I ride the bus, I can get, I can have four and a half hours each way, so then I'll have 10 hours, 10 hours should be enough time to do what I need to do." You know, you know, the elaborate rationalizations we, we come up with, and so I'm like, "Okay, if I take the bus, I'm, I'm green light to go to New York."

• 52:04Speaker 03

  Then I get on the bus, and I've forgotten my thumb drive. So, and then back- Problem, yeah. Yeah, back to self-flagellation, I'm like, "Oh, I can't, I'm like, I keep doing this, I suck, you know, 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." I'm like, "I know, this is so stupid, like, I'm so sick of like, email, like emailing myself a file." Like, what is the question for which, there's no question for which that's the right answer. I'm like, "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 like, manage our files."

• 52:49Speaker 03

  That, carrying around a thumb drive, all the things we used to have to do. And I'm like, "I never wanna have this problem again." So, I, on the bus, I opened up the editor and started writing some code in Python that basically was this seed that sprouted into Dropbox. But, it's weird, and I was just like, totally possessed with that problem. Because I'm an engineer, again, I'm, I'm like, an engineer by upbringing, my favorite classes at school, other than some of the stuff we've talked about, was, are like, algorithms, distributed systems, you know, and I found myself at a crossroads, where I'm like, "Look, I love standardized tests as much as any human possibly can, I guess." But, it was, a couple things happened.

• 53:33Speaker 03

  So, one is I like, pause, I'm like, "Okay, I'm, I'm working on this company."

• 53:38Speaker 03

  I'm kind of burning out. Part of why is because I thought about like, even if all of my dreams come true and like everything we hope for happens with this SAT prep company, then I'm like, then what? And I'm like, I'm like king of SAT prep.

• 53:56Tim Ferriss?

  Right.

• 53:57Speaker 03

  And there's nothing, I mean, I think that's fine and like people need help with these things and but I'm like, that's not what I want to do. I'm just picturing this kind of like 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. And so sometimes it's hard, you know, 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.

• 54:41Tim Ferriss?

  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, 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?

• 55:18Speaker 03

  Yes. So Paul Graham is best known as the, as one of the founders of Y Combinator. So they are, which is an incubator for startups and they were our first investors and they also invested in a lot of great companies, including Airbnb, Stripe, a lot of them. And Paul was, before starting 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.

• 56:00Speaker 03

  That gained a big following. And he was also one of the creators, or at least was very early in the conversation around using Bayesian methods, using this kind of math to do 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.

• 56:41Speaker 03

  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-

• 56:59Tim Ferriss?

  Wait, hold on, hold on, pause. Why didn't, why didn't the virtual meeting go well?

• 57:02Speaker 03

  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 for, for the Summer Founders Program, which is basically, it was like the same thing as Y Combinator. Like you get a little bit of money and all come together. It was like 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. And then, but a couple of 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,

• 57:46Speaker 03

  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-

• 58:17Speaker 03

  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, alright, well, maybe to get in, 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 new, this news site called Hacker News, which is kind of like Reddit for startup news.

• 58:57Speaker 03

  And, and I'm like, what is, I thought, I'm like, I had a, 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 just 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 then go from there. It actually worked. So, I made, and, and, I, 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? Yeah, something like that. It's like, how do you do that when you have no money?

• 59:40Speaker 03

  So, and so, they're like, all these, so there's, 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, 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. 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 at 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.

• 1:00:25Speaker 03

  And then, I'm like, okay, this is, so far the plan seems to be working. And I'm just like, keep hitting refresh on my inbox, I'm like, maybe, I wonder if Paul has seen it? And then, low and behold, I get an email from Paul Graham, saying like, hey, it looks pretty cool, but, you need a co-founder.

• 1:00:44Speaker 03

  Because they didn't, especially at the time, they didn't like single founders applying and I didn't have a co-founder yet. This was, this was before I met Arash. So I was like, oh god. Because the only problem was, I agreed with him. The only problem was the application deadline was, 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. Right. And so hilarity ensued. But, but then I was, I flew out to San Francisco. I'm like, I'm like trying to shake the trees for any co-founder candidates I hadn't thought of

• 1:01:28Speaker 03

  because for one reason or another, all of my close friends and people that would have been the, 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, I found, another friend of, I was actually getting, 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 1pm. 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.

• 1:02:12Speaker 03

  Maybe I could just like drive down to Mountain View and just like pitch Paul. Maybe that. I get to Zipcar, I like fly down 101. And like, the plan was like working pretty well. I got it, I, I got to YC, I went in the office. As expected, people were just chilling and kind of, there was some downtime. And so, and so I go like knock on, like I go, I go to Paul's office and sure enough, he's in there, he's just chilling. I'm like, hey Paul, do you have a minute? I just wanted, you know, I just wanted to show you something I'm working on. And he's like, nope, I'm busy.

• 1:02:57Speaker 03

  And I'm like, okay, look, I'm like, I can almost see your screen. I know you're just like hitting, you're just like reading Hacker News right now. Actually busy.

• 1:03:08Speaker 03

  But it's like awkward. So I step outside and I talked to Jessica, who was his partner in co-founding YC together and his wife. And I talked to Jessica, I'm like, hey, look, Jessica, and I had met Jessica before. So I'm like, Jessica, I'm really sorry to bother you guys. I just have a co-founder who was like looking for some feedback from Paul to make his co-founder decision. You know, I got a flight back in like four hours. I 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, Drew, of course, like, no problem. Like, Paul's not doing anything. Just like, just, it'll be fine.

• 1:03:51Speaker 03

  So I go back in there. And it's like,

• 1:03:58Speaker 03

  detonation. It's like, I say like three words and Paul's like, no. He's like, I'm not going to see your stupid demo. The whole reason we have an application process is so that randos like you don't just like show up here and bother us. It's like, no, please leave.

• 1:04:15Speaker 03

  And so I'm like, okay, thanks, Jessica. Thanks, Paul.

• 1:04:20Speaker 03

  Like, my friend, that's, I'm like, this is not going to be good. I'm like, this is a rough, rough return to San Francisco. So needless to say, the co-founder situation did not work out.

• 1:04:30Tim Ferriss?

  You were like, Paul's, Paul's thinking about it. Let me get back to you.

• 1:04:34Speaker 03

  Well, I did, I did meet with the dean of admissions. He just thinks I'm an asshole. So.

• 1:04:42Tim Ferriss?

  I think he's, I think he's coming around.

• 1:04:44Speaker 03

  That was a tough plane ride home. But it's good training. Like, this is, you know, this is, you gotta, this is like the new normal. If you're starting a company.

• 1:04:54Tim Ferriss?

  Let me, let me just hit pause for one second. What were you, what were you saying to yourself on the way back? Like, what was the self-talk on the plane ride back?

• 1:05:02Speaker 03

  I was like, I have, I could not have like F'd this up any worse if I had tried.

• 1:05:10Speaker 03

  Cause like now I'm a co-founder and I'm like, I might've been able to get in if I just like, hadn't like,

• 1:05:20Speaker 03

  maximally pissed off Paul.

• 1:05:24Speaker 03

  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. 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. 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.

• 1:06:07Speaker 03

  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, like I need a co-founder. You know, is there anyone you'd recommend? And he recommended me to, it turned out that Kyle and Arash were floormates 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, he was a senior undergrad at MIT, computer science student. And he was like, hey, I got this email from Arash and said like, hey, I saw your video on Hacker News and Kyle said you're looking for a co-founder.

• 1:06:52Speaker 03

  You know, maybe we should talk. And then it was kind of insane. Like, 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. You know, I was figuring this is going to be like a process, right? I'm going to have to like talk to his parents and like reassure them. But no, like we hang out for like two hours and then he, then like, then we, the two of us commit to like 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 so, but against all odds, so Arash and I team up.

• 1:07:35Speaker 03

  I think Paul forgot about his meeting with me, or didn't like, put the two together. So we did our interview, and we got into YC. So, and it was funny, because like, we, and then we're 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, our car got broken into and our laptops got stolen.

• 1:08:02Tim Ferriss?

  Oh, God.

• 1:08:03Speaker 03

  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, from Paul saying, hey, we want to fund you guys, and, and did it up. I mean, I, I don't know, it was, it was nuts.

• 1:08:18Tim Ferriss?

  So, I, I don't know if this has changed, but for some period of time, I think it's probably still the case, but, 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.

• 1:08:37Tim Ferriss?

  And, but, I mean, certainly Dropbox has done incredibly well. At what point did you go to, go to Paul's office, knock, knock, hey, Paul, like, in brackets, now we're friends?

• 1:08:52Tim Ferriss?

  By any chance, do you remember when I came in during Tuesday, on a Tuesday, not too long ago, da, da, da, da? Did you ever bring that up with him? Or did he learn about it through some other means?

• 1:09:06Speaker 03

  I like to remind him about it every couple, every year or two. I mean, first, he's like, totally embarrassed, like, he didn't, like, he didn't put any of these things together, he didn't know, he didn't remember it.

• 1:09:19Speaker 03

  He's like, I was so awful at this app. So, the, the, mostly, it's just, they, they, both Paul and Jessica turned like, bright red, and they don't like to talk about it, which is like, why I like to keep poking at it every now and then. It's all, I mean, it's all good. I would have done this.

• 1:09:32Tim Ferriss?

  Yeah, of course.

• 1:09:33Speaker 03

  For him, like, God.

• 1:09:33Tim Ferriss?

  Yeah, yeah. Well, he did tell you, I'm busy, right?

• 1:09:36Speaker 03

  I was super obnoxious, but, you know.

• 1:09:39Tim Ferriss?

  Was Drop, was Dropbox the original name of the company?

• 1:09:43Speaker 03

  Yeah.

• 1:09:44Tim Ferriss?

  It was, wow. So, so just from day one, you had the name that stuck.

• 1:09:48Speaker 03

  Oh, but getting the domain, it was GetDropbox.com. Getting the Dropbox.com domain name was, oh my God, that was, that was a journey.

• 1:10:01Speaker 03

  So there was, I don't know, I'm like, I'm like, starting to shake a little bit going, I don't know, I don't know how illuminating this, this story is, but it didn't-

• 1:10:11Tim Ferriss?

  No, let's talk about it, because people, I mean, people run into this stuff, I'm sure, I'm sure we can, I'm sure we can pull some lessons from it.

• 1:10:18Speaker 03

  Yeah, so I-

• 1:10:19Tim Ferriss?

  I remember GetDropbox.

• 1:10:21Speaker 03

  Yeah, so Arash and I fell, so the, the, the name Dropbox, actually, the behind the music version, like, the story behind the name is also probably unintuitive, or like, not what you'd expect, so, um, you ask, what am I like, what was I like in high school, um, and the answer is like, basically, he's a huge nerd who likes computer games, and that's true. Uh, one of the things we would do is we'd all bring our, uh, we would like, a bunch of friends and I would bring our computers to someone's house and we'd play games. And, um, so back in the day, these things were called LAN parties, um, they are about as cool as they sound, um,

• 1:11:00Speaker 03

  and, uh, and, you know, you all show up and play till, you play till sunrise and, and so on, but you bring a bunch of people together and often someone doesn't have the, the right maps, or the right patch, or the right whatever, and so we had a convention, like, you just create a folder called your Dropbox, that's shared and writable by anyone, um, and that's how we would exchange files, um, so that people could play games. Um, and then it's, I remember this, it was like, Christmas 2006, I'm trying to come up with a name for Dropbox, or didn't have a name then, I, uh, the initial name, I had like, some, uh, what, the name

• 1:11:42Speaker 03

  before, I was, I was busy photoshopping a logo, the initial iteration of it was Folder Anywhere, which-

• 1:11:50Tim Ferriss?

  Catchy, catchy.

• 1:11:51Speaker 03

  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 like, like, of course, the probably logo's like a literal folder or something, it like, totally inane, and then, I start, and I'm like, and I, you know, believe it or not, FolderAnywhere.com was actually available, so I, I was the proud owner of FolderAnywhere.com. Then I realized, then I did a search, and I found, there's a company called Files Anywhere- And I was like, no. Like, I can't, I, that's, it's, like, I can't, now I can't name it Folder Anywhere.

• 1:12:35Speaker 03

  And so I'm, 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, Folder Anywhere is taken. Like, maybe I should just, you know, maybe, maybe I should just call it Dropbox, like, from the, you know, from, from high school, uh, from LAN parties. And he's like, "Okay, whatever." And, and then, um, and then at Dropbox.com, I'm not available, uh, so I got GetDropbox.com. But then, um, so, we just lived with GetDropbox.com for a while. I tried to, you, you can sometimes look up who owns a domain and, and contact them. And so I tried, I actually did. I managed, I managed to give the guy a call. Um, and I'm like, "Hey, are you Dropbox.com, you know, are you, are you using it?"

• 1:13:19Speaker 03

  And the, the guy was like, "Uh, 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, uh, 2007. And then, then we, then, then we get distracted with the whole getting into YC, finding a co-founder, all that, doing YC. And then I land in, then we moved to San Francisco in September. And I'm like, "We really need to get this domain name." Um, and unfortunately, Arash and I had totally fallen in love with it, so like, uh, we weren't really, we kind of only had one plan. By the way, that's, that's called a great, uh, negotiating position.

• 1:14:04Speaker 03

  Yeah, awesome. It worked out as well as you'd expect. So we, I'm like, "Well, since loving a Zipcar and show up at someone's house worked so well the first time, we're gonna do it again." So it turned out the guy lived in Pleasanton, um, and he was an entrepreneur. Like, here's someone who's like nearby, who should be sympathetic to our cause, at least to some extent. Um, and I'm like, and I call him, and I'm like, "How's that project going?" 'Cause there's obviously no project. And, and he's just kind of being difficult. Um, and so I'm like, "I'm like, okay, goddamn it." We, we get off the phone, and I'm like, "All right, Arash, let's just, like, show up at this guy's house."

• 1:14:46Speaker 03

  Let's just see what happens. So, jump in another Zipcar. We go to the, we drop, we go to like the, the corner store and get their like most expensive bottle of $20 champagne we could get.

• 1:15:00Speaker 03

  Get in the Zipcar and go to his house. And it's like 9:00 at night, so...

• 1:15:09Speaker 03

  I don't know, this seemed like a good idea at the time. So, we, we, we show up and, and then he was kind of, I think he was kind of shocked, kind of amused, like lets us in.

• 1:15:19Speaker 03

  We have, we start talking, he's like, we're like, "Hey, look, you know, we're, we're, we're pretty serious about this thing we're doing, you know, we'd love, you know, if, if it's true that you're not actually doing anything with the domain, you know, like, help us understand what you're trying to accomplish." Not in a monochious way, just like, you know, but at least consider this alternative where, you know, we use Dropbox.com, you know, we've got some really good folks who are excited about this and involved, whether that's Y Combinator, we just got funding from Sequoia, our first venture capital investor, who's one of the best in the world. And so, we're like, "Sequoia is the best thing."

• 1:15:55Tim Ferriss?

  Oh, you, oh, you told them that?

• 1:15:56Speaker 03

  Yeah. Right, yeah, I'm just really building up our leverage here.

• 1:16:01Speaker 03

  So, this would be called hemorrhaging leverage. Although, at the same time, you know, these, these, the frameworks don't completely account for everything, because if you don't-

• 1:16:12Tim Ferriss?

  Sure.

• 1:16:13Speaker 03

  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, we're like, "Okay, so like, at least get, sketch out a case that a reasonable person would look at and be interested in." So, and then he's like, "Cool, it's interesting, I gotta talk to a friend, and, you know, why don't you, why don't we touch base soon?" And I'm like, "Great." Well, it's like Friday, I'm like, it was like a Friday night, I think. And I'm like, "We'll be, we'll be back on Monday."

• 1:16:49Speaker 03

  And we're in the ride back going over the Bay Bridge, and I'm like, "Holy shit, we might actually be able to get this thing. Like, this guy's been impenetrable and so difficult." Like, we're both kind of in awe, and just like, 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."

• 1:17:11Speaker 03

  And we're like, "Are you kidding? Is this for real?" Like, no, I'm like, "Where's this gonna go? Are you gonna like, are you gonna bequeath this domain to your children? Like, what the hell?"

• 1:17:23Speaker 03

  But he was just like, totally wouldn't budge, and so that was a much sadder drive back.

• 1:17:30Speaker 03

  So then this guy, and then there's just kind of nothing for a couple of years, or for a year. And then we launched Dropbox, we put a, we launched Dropbox publicly,

• 1:17:43Speaker 03

  and then all these confused people start going to Dropbox.com

• 1:17:50Speaker 03

  and presumably start trying to, and they wanted 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 are looking to get into the Dropbox beta. And then he does, god, he, and I'll end the story in a reasonable amount of time, but we like, 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, like it went from like a GoDaddy parking page to like a Google AdSense for domains page.

• 1:18:28Speaker 03

  Which was a problem, because then we're like, "Oh my god, now this guy is like totally cashing in." Like, 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, I'm like, "What the hell are we gonna do about this?" Like, our investors think we're idiots for not changing the name, we're doing all these like pointless branding exercises that

• 1:18:52Speaker 03

  did not go well, like to try to find an alternate name, so... I'm just like, oh my god, like, what are we gonna 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 arms care expert in this stuff. And it turns out, you can't just like, get a domain from someone for no reason. Like, 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.

• 1:19:30Speaker 03

  But, it is also illegal for someone to intentionally confuse your customers. So, I can't just like, say that we're, you know, I can't sell paper towel, or I can't sell like, Kleenex with three E's to confuse people, or whatever. So, 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 our common law trademark rights.

• 1:20:11Speaker 03

  And so, I'm working with this crazy trademark, like, trademark and domain attorney. And so, we sue him for trademark infringement. And so, that got his attention. And, which we would not have done. Like, we weren't just trying to push him around. I mean, it was really, he was trying to profit off of confusing our customers. So, we were... For sure. Got on our high horse after that. And, I mean, that was a comical whole experience, but, eventually, he's like, okay, okay, okay. You know, I'll, like, this is no point to have this lawsuit. You know, I'll give you guys, or I'll sell you guys the domain. I'm like, okay, well, like, we can offer you stock or cash. He's like, I'll just take cash.

• 1:20:55Speaker 03

  So, we paid him 300 grand, got the domain, lived. I mean, that was such a, like, sending that first email from Dropbox.com to Paul and Jessica was a huge triumph. But, what, even, we offered him stock, at that, like, would have been at the seed round. Oh my god. Which would be worth, like, multiple hundreds of millions of dollars today.

• 1:21:26Speaker 03

  I think what you can take away from this is like, there's just no manual for that, right? You gotta just kind of wing it. And there are a lot of things that are the equivalent, even today, of just kind of getting in the zip car with a bottle of champagne and hoping for the best. And, you know, sometimes you'll get really good cards, sometimes you'll get really bad cards, but you just gotta kind of roll with it. And so, between finding a co-founder, getting the domain, each of those is definitely, those are definitely memorable points along the journey.

• 1:21:59Tim Ferriss?

  Well, we were chatting a bit before we started recording about the psychological aspects of, say, prepping for starting a company. And I want to tie that to a company you mentioned earlier, which is Reddit. And so you mentioned that Hacker News is sort of Reddit for the computer science slash hacker subset, right? And I remember having Alexis, the co-founder, on this podcast, and 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. And the executive said, wow, something along the lines of, oh, my God, you're just a rounding error

• 1:22:41Tim Ferriss?

  for Yahoo. And it was so insulting that Alexis took, like, you are a rounding error, I think it was, and put it on the wall in the office to motivate, right? But that's, that is one of several different responses that are possible, right? I mean, there are, there are certainly people who'd be crushed by that. It could be the end. And I don't, I don't remember exactly where this quote is from, but I want to talk about when this came out and how you, what the self-talk was. So the, okay, there's an article being written about Dropbox, and I think the quote was, quote, "Fortunately, the Dropbox founders are too stupid to know

• 1:23:25Tim Ferriss?

  everyone's already tried this," end quote.

• 1:23:28Speaker 03

  Yeah.

• 1:23:29Tim Ferriss?

  So, when did that happen? And how did you and anyone else involved respond to it?

• 1:23:41Speaker 03

  Yeah, so that was very early. I would say it was probably within the first year. And probably the most... Well, I think what happens is you'll get... I mean, I just think even back to that first video that I put on Hacker News. A lot of the... Actually, a lot of the commentary was positive. People like, "I would use something like this. It's good." And it was really... And that was really encouraging. So on the one hand, half the peanut gallery is saying that. The other half is saying, like, listing all these reasons why it's been tried before and won't work. And then even if it does work, like Microsoft, Google, everybody's gonna kill us. And here's why it's never been a business, and here are all these other ones that have never succeeded, da-da-da-da.

• 1:24:25Speaker 03

  And the thing is, I agreed with them. I was like, "Yeah, you're probably right." Like, I don't really see how we survive as... I mean, in 2007, I don't see how we kind of make it through, you know, to Mount Doom. You know? As our little, like, plucky band of the two of us. And then invariably, every investor we talked to would raise similar concerns. So the feedback was all pretty negative. So it's easy to say, like, "Oh, just ignore it all." But you kind of have to... You have to be balanced. So on the one hand, we did get encouraging feedback in the beginning. So people were like, "Drop it. This is cool. I would use this. It sounds great."

• 1:25:10Speaker 03

  And I knew that I needed it. And then I wasn't, like, trying to create a billion-dollar company. I was trying to just, like, solve a problem. And so 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, it'll be one of... This is just another side project and a number of side projects. And like, let me not suffocate it by putting all these crazy expectations on it." So I think that's pretty important. And then people are like, "Oh, when did you know it was a success?" It's like, well, it was sort of a different point. It was like the goalpost for success kept successively moving back. So even just having a video was a big milestone, and launching a private beta was a big milestone, and there are a bunch of milestones.

• 1:25:52Speaker 03

  But so it was sort of a continuous process more than, like, "Oh, is this one moment in time?" But yeah, there were people who had very good arguments about why this wasn't gonna be successful. And that's why I think...

• 1:26:07Speaker 03

  You have to have, you have to sort of have, you have to have both thick skin and thin skin. You have to have, kind of get that balance right. Because if you just have, if you just ignore all of the feedback and dismiss it all, then you're probably, you're probably gonna have some kind of blind spot and you're gonna, you're gonna miss some important information. So, just because they came, but, but just because they came to that conclusion doesn't mean that their assumptions were all correct. And that's why you also need to have enough thick skin to know when to like, when to be a little bit dismissive or not listen to everything. And part of what helps with that is having conviction.

• 1:26:48Speaker 03

  And conviction that comes from being able to think from first principles. And pay less attention to people's conclusion, like the outputs of people's conclusions as much as the inputs into those conclusions. So what does that mean? Well, people said that, okay, the Dropbox is not gonna be successful because the people have tried it a million times. And that is, that is true. And anybody who, that's like factually true, it's not, you can't debate that. But that would have been true for mobile. Like every phone, every mobile thing before the iPhone, or every mobile software company, every app, like was a total failure. Before the iPhone, world changes, suddenly it's the right time. And so, if you study history of technology or history of business, you realize, okay,

• 1:27:31Speaker 03

  that, that argument is not in and of itself causal. So, what you want to answer is like, oh, why is that incorrect? It's like, well, actually, there, there are a lot of good ideas that are, are bad ideas for a while because the timing is wrong, but then the timing becomes right because of some discontinuity in tech and like, and, looks like the innovator's dilemma or others will illustrate that. And so if you really understand these, if you understand, that's why it's important to build these mental models, because you were like, alright, 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 happened before, like has failed before, doesn't mean it will always fail in the future. Can still fail, but...

• 1:28:14Speaker 03

  But that kind of conviction came from an understanding or a belief and a worldview and framework of like, here's how I think business works, or here's how to think about an idea like ours. So, but that said, it's not, so I think there's a, how do you receive advice and how do you sort of develop first principles thinking, which we talked about, but then like, that doesn't make it feel any better when people are like, your idea sucks and you're gonna fail. Or even worse than that, like, you are stupid, right? It's really at, super ad hominem. Right. Yeah, people are not, so, first of all, I think you have to have a sense of like, this is normal, like, just don't take it too personally, because that's the thing, you want to take

• 1:28:59Speaker 03

  it, you do want to take, you want to receive the feedback and like, try to extract the kernel of, that's useful from it, but not feel obligated to, 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, like, alright, now we, like, Sequoia has decided to invest in our company, against the odds, now Sequoia has decided to invest, they're, they're writing us a check for a million dollars, I hope they realize that, like, I've never, I've not, I haven't like, really done this before, and like, oh god,

• 1:29:43Speaker 03

  like, that million dollar, it's great to kind of cash that check, but, oh man, they're gonna be looking for that money back at some point, like, what are we gonna do? And so, that's not, there wasn't, I mean, there were probably a lot of things going on in my head at the time, but, and then like, oh my god, I've never really built a successful company, or I don't, I've never managed people, really, you know, the idea of Dropbox being a hundred person company is like terrifying, like, I'm, this treadmill's just gonna go faster and faster, until like, I'm violently thrown off of it, like, how am I gonna deal with that?

• 1:30:18Speaker 03

  And a lot of me also felt like, okay, well, I'll just like build the company until it's like successful enough or makes enough money where I just don't have to worry about money anymore. And then I like, as soon as I get to that, I don't know, this was just like some kind of theory. I'm like, all right, as soon as I get to that level of success, I'll just stop and like, just so I don't screw it up. But then interestingly, that that goalpost kept moving back and moving back and moving back. So I think it's never really been about the money, but you can read in the Y Combinator application, like that's now public, where you put that out there. And I'm like, I would, if I had a million dollars after taxes for six months of work, I'd consider that a pretty good

• 1:30:58Speaker 03

  deal. So, but more on just like that, what do you do? And you're like, oh, my God, this is like, pretty uncomfortable. I've never done anything like this before. I might screw it up. You need, so your instinct will to be to run away from that feeling. And what you need to learn to do is run towards it. Because that's just gonna keep, keep happening, keep happening. I'm like, you know, we're gonna drive, show up at this guy's house. I don't know, maybe we'll get arrested. But we're gonna do it. I don't think that's the best example. There are just so many things where it's like, you just gotta kind

• 1:31:37Speaker 03

  of figure it out and keep going. And Ben, one of the great things from, that Ben wrote in his book, The Hard Thing About Hard Things, is the hardest part of being a CEO is managing your psychology. And I didn't really know what that meant at the time. I think I have a much better sense now. So I think first thing is being comfortable with being uncomfortable. Because, and 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, so understanding that that is, and sort of zooming out and understanding, like, depersonalize it. It's like, it's not really you. This is just like the process of growth. It will

• 1:32:21Speaker 03

  be painful, or think of your journey as more of an adventure, rather than like a final exam where you have to get everything right. And you only got one shot. I think that's pretty important. And then second is, all right, you have to, now, it's, everybody likes the idea of growth and pushing yourself, but You also have to take care of yourself, like you have to find ways to metabolize stress and avoid burnout. And for some reason, people just, they just use the one tool of like pushing themselves harder and then they break. And you know, you wouldn't do that to your car, you wouldn't do that with like a musical instrument. So, why would you do that to yourself, right?

• 1:33:05Tim Ferriss?

  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.

• 1:33:28Speaker 03

  Yeah, I wouldn't say I'm the best like athlete by any stretch, but I, but it's really important, you have to do enough so that you don't break down. And so, and you gotta 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 gonna 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, you know, I think some of the stupid, the dumbest advice that people get is like, you know, not sleeping or wearing, like, or just pursuing this idea that, that successful people somehow work like 70, 80 hour weeks and that's the norm. There are a number of problems with that. First, it's like usually not true, it's usually more of an indication the person's either

• 1:34:13Speaker 03

  lack of awareness about where they're spending their time, or lack of effectiveness if they need, if their only tool in the shed is like work more hours.

• 1:34:23Tim Ferriss?

  Right.

• 1:34:23Speaker 03

  Because, just think about that, like you, you know, that is, that has a ceiling in terms of how much of an advantage that can give you. Like, yes, you wanna work hard, but if your only advantage is like being able to work 20% more hours than someone who's merely very committed, then you're not gonna have outsized results. And you also, I mean, there's, so there's, anyway, I have a, I think this meme that people, that successful people work 100 hour weeks or something is both false and super harmful. Most of the most, the most successful people I know actually work They have crunch times where they're super busy, but they otherwise have a work week that looks more normal than not.

• 1:35:06Speaker 03

  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 in your calendar, if you can't see your gym time on the calendar, it doesn't exist.

• 1:35:28Tim Ferriss?

  Totally.

• 1:35:29Speaker 03

  So, and then, and then I think like self-awareness, there's probably a lot more we could talk about how to metabolize stress and avoid burnout. But I think having, like taking care of the basics, like having a good foundation and setting healthy boundaries is pretty important and having a sustainable workload. Self-awareness is pretty important and being willing to like shine a hard light on yourself and embracing that. So for me, coaching has been super helpful.

• 1:36:03Tim Ferriss?

  Coaching meaning you have like an executive coach?

• 1:36:06Speaker 03

  Yeah, I've had different ones over time. And, and really, and like I go through that experience, I'm like, I'll give this a shot. Some of my friends have had, have spoken positively about it. But it's a little, it's, well, I'd say the first part, I remember my first coaching experience and like getting, they do the 360 and then you sit down, you do your review of your results.

• 1:36:30Tim Ferriss?

  So, sorry to pause. So 360, for people who don't know, is where you have any superiors, peers, employees, et cetera, people who know you really well, interviewed about your strengths, weaknesses, and so on. Would you, is that fair to say?

• 1:36:44Speaker 03

  Yep. Well, you get all this feedback from all these, you know, everybody you work closely work with, so it's kind of overwhelming. Cause you get a lot of it. And it's not all good. So.

• 1:36:59Speaker 03

  And actually, to this day, like, opening those documents and like, reading all the 360 feedback is one of the most painful, like, human experiences you can have. Maybe that's a little hyperbolic, but, but it's not fun. It's at least not fun. It's not something that I look forward to. But it's important. So, because you need to know. Like, it's much better to just, like, know and be able to do something about it. Like, Ben, Ben's been a great friend and mentor. And he's like, he was reflecting, he told me a quote that one of his mentors told him, which is like, "God gave us all weaknesses. It's a blessing to find out about them." Hmm. You know? Sobering. You know? But, so, but I went through, yeah, I just remember my first, first coaching experience,

• 1:37:44Speaker 03

  briefly, like, you know, I sit you down, they're like, first page is usually like, "Here are your strengths." And I'm like, "Okay." He's like, and my coach was like, "You are really, you really, really care about people. You love building great relationships." And I'm like, "Yep, okay, yeah, that sounds, that sounds good. You're really creative, you like new ideas." I'm like, "All right, I'm enjoying this coaching thing so far." He's like, "You're really comfortable in chaos, like, it doesn't bother you that this stuff is like, so crazy." I'm like, "Yep." It's like, "Okay, da-da-da." And then flip to the next page. Right now, like, it's never weaknesses, development areas. That's right, or opportunities for improvement. Yeah. So I'm like, "All right, so let's hear about some opportunities."

• 1:38:27Speaker 03

  He's like, "You are really conflict avoidant. You don't make hard people decisions. People don't know what you, like, where they stand." I'm like, "Okay." He's like, "You're unreliable, you drop, you drop balls. You're not paying enough attention to the things that are important." I'm like, "Okay." And he's like, "And you suck at planning. People are confused about what to do." And I'm, I'm like, "Okay." And then he's like, "Look, okay, you're good with people, so, and you like people to be happy, so you avoid conflict. You are creative, you like new ideas, so you don't, you don't pay attention to the routine stuff. You're comfortable in chaos, so you don't plan."

• 1:39:12Speaker 03

  Like, these strengths are all like, their own weaknesses in disguise, like, so, and there's no one who's like, 10 out of 10 on everything, and that's, that's why. So...

• 1:39:24Speaker 03

  You know, there's a lot of different philosophies on what do you do with the feedback? And, you know, do you play more to your strengths? Or do you, I think you need at least to get your weaknesses to a point where they're not like destroying the company. But generally, you want to play to your strengths, and that's one of the key effective executive tenets. But, other than that, I think just self-aware, like trying to understand yourself on all kinds of different dimensions is really valuable. I talked about the Enneagram in your book. Yeah. And that's, it's sort of like, I would call it like a useful Myers-Briggs. So, most people are familiar with Myers-Briggs. It's a personality typing system, but then you read it, and it's like reading a personality quiz on the internet. You've sort of, you remember, you had some letters, and there's like some stuff, but you don't actually do anything with it.

• 1:40:08Speaker 03

  I found Enneagram to be similar in terms of it's a, there are a limited number of personality types, but it's much more a theory about what fundamentally motivates people, what demotivates them. And so, I know we don't have a ton of time, so I just say like, "Check it out." Enneagram is very valuable. Like, I do it. My, I was, I was super skeptical. I was like, "This sounds like a cult." And it kind of is. But, it's been very helpful, both to do individually and with your team. Because it just, you sort of, what you learn is like, "Okay, here are the, here are my blind spots." I was like, "Sorry, I'm an Enneagram seven." These are like totally textbook strengths and weaknesses of a seven, that they like, they like new things, they like, they're comfortable in chaos, but then they can become

• 1:40:53Speaker 03

  distracted and, you know, and unreliable. Conflict avoidant, things like that. So, just knowing, you always, one way or another, you always want to have an accurate map of like, what do you need to work on? How were you, how were you introduced to Enneagram? Well, so it was through my co-founder, but then Raj was introduced to it through a guy named Gentry, who was the founder of Mailbox, who worked with us for, for a while. So, it's, you know, call it three, four years ago. And then Raj was like, "You're gonna love this, it's great, da-da-da." And I'm like, "It sounds super weird." But, he was right. So, it's, it's been super helpful.

• 1:41:31Tim Ferriss?

  Awesome. Well, I know we don't have a ton of time left and maybe sometime we'll do a follow-up with some wine and I'd love to talk to you more about your cadence and so on with an executive coach. Maybe we can get to it another time. But I thought we could wrap up with another thing that you mentioned in the book, you know, Tribe of Mentors, but I'd love to hear you talk about it, which is the tennis ball, circle, and the number 30,000. Can you tell us where this comes from and what that means?

• 1:42:01Speaker 03

  Sure. So I did the commencement speech for MIT back in 2013. And I was like, the whole premise was, I'm like, all right, God, I'm like, I'm 30. I don't really, I'm like, can I wait 20 years? I'll say something like way more insightful then. But I'm like, all right, well, I gotta, the prompt, the prompt I came up was like, what do I wish I had known? What would I tell my 23-year-old self? And if I could sort of send a cheat sheet back in time, what would it have on it? And what I would put on that little cheat sheet is, as you said, a tennis ball, a circle, and the number 30,000. So the tennis ball is really about finding that thing you can become obsessed with. And so when I think

• 1:42:44Speaker 03

  about like Dropbox, or even just other side projects like the Pokerbot, like I am both most productive and happiest and most successful. And like, when all those things line up, or when the thing you're obsessed with overlaps with something the world really needs, or values. So, but like, don't settle. Like, find something that, the tennis ball, sorry, what is it? Where does the tennis ball come from? I had this like, really lazy, fat dog growing up, who would, but when you showed her food, or you showed her tennis ball, she would be, just, she would just like go nuts. And so you throw a tennis ball for her. So

• 1:43:27Speaker 03

  it was like, she was just like this, it was like watching like, like a

• 1:43:34Speaker 03

  Ham running on twigs or something. It's like super. It's just bizarre. It's just funny. And so I was like, I'm like, what you want is to have like that ridiculous expression on your face and just kind of be so obsessed with something that you just don't care about anything else. Not overdo it, but like, but the point is like, find something that, not just passionate about, but like that, just like that, that you can become obsessed with and just really love and something you would do even if you weren't, you know, even if weren't your job. Then the circle concept is really, there's a saying by a guy named Jim Rohn, that you're an average of the five people you spend the most time with. And I found that to be super true. So, and then so the, and the upshot is like, choose wisely.

• 1:44:17Speaker 03

  So whether it's the literal five people you spend the most time with, or just in the environment you're in. So being, like going to a, or just find an environment that will pull the best out of you. And so, and I think that's been true for me. Going to MIT really taught me like what a good engineer looks like. And it's both inspiring in terms of watching all these people who are super like capable, but then also you get jealous and you're like, oh, I, you know, I want to be that good. And so you want to harness that kind of negative energy into pushing yourself to work harder. So, and that's what that was true whether at school or being in Y Combinator with other founders, like friendly competition there, or with my friends who were starting companies, being in San Francisco.

• 1:45:01Speaker 03

  All of those contributed massively to, to us, to us making it. And then finally, 30,000 is really about, everybody lives on average, humans live on average for 30,000 days. I was, at first I was like, okay, yes, this is like a clinical truth, not terribly interesting. Cause I think I had just moved to San Francisco and I was, and I was just like, I couldn't sleep. So I was just like on the internet, reading stuff. And I came, came across that and I remember being like, huh, okay. And I opened a calculator and I'm like, all right, I'm 24 at the time, 24 times 365. I'm like, oh my God, I'm like already 8,000 days now.

• 1:45:43Speaker 03

  So this idea of like 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 like, think of life more as an adventure or a story more than how you think about life as when you're graduating college, which is like, life up until you graduate college is just like a series of checking off boxes and like getting ready for stuff and performing. And all of your worldly achievements can be, are averaged into a GPA. And so every mistake is like, brings that number down and like, it's something you have to like 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.

• 1:46:27Speaker 03

  You're not an average of all your successes and failures. Like, you should change your mindset to life and also just think of it more. So just making a story that's interesting, not just, not trying to be perfect. Because I think that's a trap that a lot of people fall into. So anyway, those are, when I thought about, you know, if you were to play everything over again a hundred times, who knows what would happen? But if I could just hand back a cheat sheet, that's what I would put on it.

• 1:46:55Tim Ferriss?

  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's no exception, so I'm gonna let you get back to your day. But do you have any closing comments, asks, suggestions, or anything else for people who are listening to this? Any, any kind of parting comments before we wrap up?

• 1:47:21Speaker 03

  Uh, let's see. So I, um, I think, yeah, just don't, don't forget to have, like, don't forget to have fun and like, and I, I think at the, at the end of it, you wanna have, like...

• 1:47:38Speaker 03

  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, and even, like, what you want to do is write an interesting story, not like a perfect story.

• 1:47:53Tim Ferriss?

  Yes, yes, and I mean, 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." Like, that is one of the recipes for writing a successful screenplay, and, you know, 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,

• 1:48:35Tim Ferriss?

  but I appreciate you carving out as much time as you did to share your stories with everybody.

• 1:48:40Speaker 03

  For sure. Well, thanks, Tim, it was a lot of fun.

• 1:48:42Tim Ferriss?

  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, etc., 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. 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

• 1:49:26Tim Ferriss?

  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 fourhourworkweek.com, that's fourhourworkweek.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. This episode is brought to you by WordPress.com. I love WordPress.

• 1:50:11Tim Ferriss?

  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 Tequila Ferris 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, 538, TechCrunch, TED, CNN, and Time, just

• 1:50:55Tim Ferriss?

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• 1:51:40Tim Ferriss?

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• 1:52:24Tim Ferriss?

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• 1:53:07Tim Ferriss?

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