The Tim Ferriss Show - #334: Drew Houston — The Billionaire Founder of Dropbox

Episode Date: August 27, 2018

"Write an interesting story, not a perfect story." — Drew HoustonDrew Houston (@DrewHouston) is co-founder and CEO of Dropbox. Since founding the company in 2007 with Arash Ferdowsi, Drew has led the company's growth from a simple idea to a service used by 500 million people around the world.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, the global creative platform that makes it easy for designers and clients to work together to create designs they love. Its creative process has become the go-to solution for businesses, agencies, and individuals, and I have used it for years to help with display advertising and illustrations and to rapid prototype the cover for The Tao of Seneca. Whether your business needs a logo, website design, business card, or anything you can imagine, check out 99designs.You can work with multiple designers at once to get a bunch of different ideas, or hire the perfect designer for your project based based on their style and industry specialization. It's simple to review concepts and leave feedback so you'll end up with a design that you're happy with. Click this link and get a free $99 upgrade.This podcast is also brought to you by WordPress, my go-to platform for 24/7-supported, zero downtime blogging, writing online, creating websites. I love it to bits, and the lead developer, Matt Mullenweg, has appeared on this podcast many times.Whether for personal use or business, you're in good company with WordPress, which is used by The New Yorker, Jay Z, Beyoncé, FiveThirtyEight, TechCrunch, TED, CNN, and Time, just to name a few. A source at Google told me that WordPress offers "the best out-of-the-box SEO imaginable," which is probably why it runs nearly 30% of the Internet. Go to WordPress.com/Tim to get 15% off your website today!***If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts/iTunes? It takes less than 60 seconds, and it really makes a difference in helping to convince hard-to-get guests. I also love reading the reviews!For show notes and past guests, please visit tim.blog/podcast.Sign up for Tim’s email newsletter (“5-Bullet Friday”) at tim.blog/friday.For transcripts of episodes, go to tim.blog/transcripts.Interested in sponsoring the podcast? Visit tim.blog/sponsor and fill out the form.Discover Tim’s books: tim.blog/books.Follow Tim:Twitter: twitter.com/tferriss Instagram: instagram.com/timferrissFacebook: facebook.com/timferriss YouTube: youtube.com/timferrissPast guests on The Tim Ferriss Show include Jerry Seinfeld, Hugh Jackman, Dr. Jane Goodall, LeBron James, Kevin Hart, Doris Kearns Goodwin, Jamie Foxx, Matthew McConaughey, Esther Perel, Elizabeth Gilbert, Terry Crews, Sia, Yuval Noah Harari, Malcolm Gladwell, Madeleine Albright, Cheryl Strayed, Jim Collins, Mary Karr, Maria Popova, Sam Harris, Michael Phelps, Bob Iger, Edward Norton, Arnold Schwarzenegger, Neil Strauss, Ken Burns, Maria Sharapova, Marc Andreessen, Neil Gaiman, Neil de Grasse Tyson, Jocko Willink, Daniel Ek, Kelly Slater, Dr. Peter Attia, Seth Godin, Howard Marks, Dr. Brené Brown, Eric Schmidt, Michael Lewis, Joe Gebbia, Michael Pollan, Dr. Jordan Peterson, Vince Vaughn, Brian Koppelman, Ramit Sethi, Dax Shepard, Tony Robbins, Jim Dethmer, Dan Harris, Ray Dalio, Naval Ravikant, Vitalik Buterin, Elizabeth Lesser, Amanda Palmer, Katie Haun, Sir Richard Branson, Chuck Palahniuk, Arianna Huffington, Reid Hoffman, Bill Burr, Whitney Cummings, Rick Rubin, Dr. Vivek Murthy, Darren Aronofsky, and many more.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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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 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 Firdozi, Drew has led the company's growth from a simple idea to a service used by 500 million people around the world. You can let that number sink in. Drew received his bachelor's degree in electrical engineering and computer science from MIT in 2006. I think I've heard of that place. After graduating, he turned his frustration with carrying USB drives and emailing files to himself into a demo for what then became Dropbox.

Today, Dropbox is one of the world's leading business collaboration platforms with 11 million paying subscribers and 1,800 plus employees across 12 global offices. Drew, welcome to the show. Thank you. You know, I've wanted to have an excuse to ask you for your life story and all these details because we've known each other quite a while, but it's super weird to sit down with a glass of wine at a dinner table or something like that and just start asking you for your Dr. Evil story. So this is a fun opportunity for me to dig in. So I appreciate you taking the time. Awesome. Yeah, me too. It's great to be here. And I thought we would start with some of the backstory that I do not know, and that is

your childhood. And perhaps you could just begin by telling us how you would describe yourself as a kid. I mean, let's just call it kind of three to sixth grade or anytime, really. What type of kid were you? So yeah, going way back. Well, first 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 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 starting a computer game company. And I thought that there would be nothing better than that. But I was that kid. So I learned programming at an early age. I grew up just outside of Boston. So I grew up in New England. And then on my way to MIT, I really liked math science. 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 which we can talk about um uh 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 um but uh but programming was even better anyway so um so uh so but but in middle school and in high school, I ended up getting a bunch of programming internships or summer jobs at startups, basically. One of them was remote. Most of them were local. But then that got me on a path of of starting companies

and being involved in startups but um i would say those are probably the um the biggest when it when it comes to dropbox and everything that kind of followed after the from my childhood it was happy childhood lots of um uh i don't say it was still pretty balanced, but programming and engineering was for sure my first love. And were you a shy kid, an extroverted kid, played sports, kind of kept to yourself at recess? What would somebody looking in from the outside, how would your third grade teacher describe you in that capacity? Yeah, I think somewhere in the middle so i wasn't 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 exists. Um, but you know, more of a math leet than an athlete. So, um, but, uh, and I was, I w yeah, I was not like

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

which I always enjoy doing when it's someone I know because I dig up all these bits and pieces that I then want to ferret out and explore a bit. So I came across this line that described folding chair on top of fraternity at MIT, and that you would go up there with piles of books and read these books. So could you place us when that was in your undergrad career and how you chose the books and why you did that. Yeah. So I, it was about my junior year of, uh, of, of undergrad. I took a leave of absence because I had an idea for a startup that I wanted to pursue. Um, so I took a year off to do that.

Uh, what I noticed was that the, this was back in 2004, so I was maybe 21, and the SAT was changing. I started an online SAT prep company because what the opportunity was was the SAT was changing in 2004, 2005 from 1,600 points to 2,400 points. So suddenly all the course material overnight was going to be obsolete. And so I saw an opportunity to maybe develop not just a course for the new SAT, but an online course. And I teamed up with a former teacher from my high school who had his own little cottage SAT prep company. And I'm like, hey, if we come together, we can put this thing online and we'll be on an even playing field

because all those 800-page books that have been printed about it are now uh obsolete and who really wants to go to some classroom at eight in the morning on saturday um anyway like we can build a much better experience if we do it online so um i was really excited about starting a company and we jumped into it and i think we we met in a chile's's and we're planning world domination and figuring out how do you incorporate a company. So it was a really great introduction to the world of starting companies. And then it also, the more I learned about the mechanics of starting a company, the more I realized I didn't know about business. And I knew a lot about engineering and programming and I'd worked at startups.

But when it came to... But there was a fog beyond just building the product. And so I was like, all right, we're going to need... I know sales and marketing and, like these are all things. And all I know is I don't know a lot about them. So, um, I had the highly scientific method of, I just was like, all right, I'm just going to go on Amazon, type in sales, buy the top three or four books and just do that for every like category. Um, 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 it was great. And it was an important combination. 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 entertainment, basically.

It's where you just 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. So there's a big difference between reading the material and studying it. Totally. But I was pretty systematic about it. I'm like, okay, here's all the stuff that I don't know. And then reading is going to be a good way to get me introduced to all these topics. And all of that, maybe the first instance of that was when I went through my high school, and there are a lot of great books that you read as part of your high school curriculum. But then I stumbled across a book, Em intelligence by Daniel Goleman. And I was like, Oh my God,

like this has just like, it's, I mean, it's nonfiction. Um, but it's, it spelled out something that was, I just didn't know you could kind of break down in a logical way. Um, and suddenly I have this understanding about the world that I didn't have before. Um, and so that was important because it sort of, it was sort of one of a bunch of early examples that anything is trainable and, and, and it got me on a path to developing what we'd now call a growth mindset. And realizing that it's possible to learn about these things that you that were 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. 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? Or were you intrinsically, using that word quite a bit, but interested in learning more about these different buckets through these different books?

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 a big culture when engineers, um, start off by being dismissive or defensive about, oh, the technology is all that matters. Or if it doesn't have a triple integral in Greek letters,

it doesn't count. Certainly like a cultural meme at MIT. Um, and I think it just creates a huge blind spot for people, um, both because it makes them less effective, but it's also like the stuff is it is actually really interesting and but i kept having experiences like that and the 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, I mean, those are tactics. But the class has these frameworks where, okay, smart people have thought about this and they've broken it down. And it turns out that there's a whole process of uncovering mutual interests

and figuring out what your leverage is and your best alternative, dah, dah, dah. And so, and, 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'm, I have to take. Um, and it's a lot more applicable to my daily life. And so I really appreciated learning a little bit about a lot of different disciplines and just putting up a folding chair on my roof was the first thing that came to mind as far as how I could actually do that. Were there any other books besides emotional intelligence during that period that really had an impact on you? Yes. So in that negotiation class,

there's a book called Getting the Yes, which is about principle 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 um i also became friends with the founders of the companies where i worked um and i went during lunch breaks or at other times i'd go like chase them down and bug them and ask some questions about like hey how do you start a company like do you have any book recommendations um just making that you know kind of taking advantage of being the bright-eyed, bushy-tailed intern and shaking down my boss or the founder or my mentors for advice. And so two of the books that were really instrumental.

The first one is Innovator's Dilemma by Clay Christensen. It's a book about how businesses get disrupted and a lot of those themes are why startups can succeed and thrive even when there are big competitors who you would think would just wipe them out and so how that cycle works. And then there's a book called Crossing the Chasm, which is another classic. It's a book on marketing, technology marketing.

It's like how do technology products make their way from early adopters to the mainstream and have you found yourself revisiting those books or were they a point in time during that rooftop amazon education period i have i mean i'd say there are a lot of you read a lot of books not all of them are as good as the innovators dilemma but then yeah it also helps to revisit some of the classics uh innovators dilemmas actually both of those books are good examples so so yeah i do revisit them because again when you're 21 and you've never had a real job, you're reading this book and you sort of get a general sense for things, but you don't really deeply understand the concepts.

And then coming back five years later, 10 years later, you can really absorb a lot more of the material. So I read a lot of books in general, and then when I'm reading a book, I'll triage. I'm like, okay, is this something I need to study? Is it something that's interesting or that I might need to know something about, or is it just fun? And if you study it, if I'm like, oh, I need to study this book, then I approach it pretty differently than if it's just like entertainment. And for those people who haven't read Getting to Yes, when you were leading into that

with some of the concepts from the class, I thought to myself, I bet that was part of the class or one of the books you read because you had best alternative. And there's a term I do recommend also people read Getting to Yes, BATNA, Best Alternative to Negotiated Agreement,

which is a really important concept to grasp. And there's another book that I might recommend to people. I think it was written later by one of the co-authors of Getting to Yes called Getting Past No. 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 teaching say a freshman class or senior class undergrad uh 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 haven't talked about?

Yeah. For the sake of starting, or if the subject of the class were starting a company, or evolving from being an engineer to being a business person, I have a handful of books that I really love and the concepts that I use and think about every day. So probably my two favorites are High Output Management by Andy Grove, which Andy Grove was the CEO of Intel, which was kind of the Google of its time, particularly back in the 80s and early 90s. So Andy was one of the founding engineers and then rose the ranks at Intel and became CEO. So he, Andy was an engineer, one of the founding engineers, and then rose the ranks at Intel and became CEO. So he, he's lived this path. And, and when I read about that, or I heard about this book and it was introduced to me as the best book on management ever written. Um, and I agree. And it just breaks down all the

mechanics of, um, okay, how do you run a team? How do you break down a goal into sub-goals? 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, nuts and bolts challenges that you encounter when you're running a team, whether that's a company or a team within a company. The second is The Effective Executive, which does a great by Peter Drucker. And the central core of that book is really about people. It's very easy to mistake effort for effectiveness.

There are a lot of different phrases for this, like, to confuse motion for progress or, but, but it's really about that idea. So how do you, um, how do you know if you're being effective? What practices, I mean, there's a bunch of practices that you can adopt that, um, that make you more effective. And then how do you avoid the sand traps of things that feel productive, but aren't actually? Um, 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, um, than others? Why is that? And what can you do instead? So the effective executive is, it covers a lot of that ground. That's ground. Those two I think of as kind of like textbooks. You want to study them. You want to take notes. You want to really chew on the

material. Then I think there's a lot of other tactical things about starting a company. I'd say a favorite book that's more about the experience of running a company is Ben Horowitz's book, Hard Thing About Hard Things, which just shows you a mess and adventure and the crazy highs and lows and 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 Almanac by Charlie Munger. So Charlie Munger is Warren Buffett's

longtime business partner. Um, and, um, and one of the, this book is really interesting because one of the things about being a CEO, um, 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? How do you train up that skill quickly? I mean, that's really called wisdom or judgment. And so it's like, how do you grow wisdom or grow judgment quickly? Poor Charlie's Almanac is a great example of a book. So it talks about how actually a lot of what you need to know to be successful in life, conceptually, you learn it in middle school or in high school.

You just don't apply it or you don't really internalize the concepts. Um, and he argues that a lot of really wise and effective people develop or basically build a catalog of mental models, um, where, uh, 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 BATNA and leverage, that might be a concept that can be applied in all kinds of different situations. Or comparative advantage from economics. Or you could go on about these different concepts, but then figuring out how do you internalize them so well that you're able to figure out, okay, these are what matters in these situations. And then how do you 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, um, and that you find yourself most of the time being able to make good, quick decisions. Um, and then, um, also on the philosophical front, uh, so Zen and the art of motorcycle maintenance. Yeah. Piercic. Yep. Um, so you talked about engineers who like dismiss like all these things that can't be fit into an algorithm or, uh, or, or, you know, that don't have some kind of like mathematical rigor, rigor underpinning them. Um, Zen and the Art of Motorcycle Maintenance is about that, like 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 for both or developing both your left and right brain, you know, to use that analogy, I think is really important if you're running a team or growing a company, because there's a lot of stuff where it's a lot about technique and data and 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 you develop products with taste? Those are things that are not going to be where you're not able to reach as much into the more rational or like kind of engineering bag of tricks. So I think developing both of those, developing both sides of your brain

or developing an appreciation for both is really valuable. maybe one more so principles by by ray delio um who was i know was a recent guest um i think he's got really concise and good um thoughts for like all right how do you sort of approach all the um how do you approach life so it's um i would include a include a mix of different kinds of things. I'd have more instructional books, more philosophical books, more story and history kind of books. Man, I want to take your class. I'm like, yeah, that sounds pretty good. Number one, so consider me pre-registered or pre 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 another book that you had mentioned, you know, the, what is it? The hard thing about hard things?

Right. And Ben Horowitz of Andreessen Horowitz and many other things prior to that. So that book, and there's, of course, a selection bias here, since I have a limited data set. But the startups that I've been involved with that have done best have kind of returned the fund many, many, many times over, almost without exception, have all read High Output Management and have a copy of it in their offices. Now, I'm sure there are many unsuccessful CEOs who also have that book, but nonetheless, The Effective Executive, actually, I'm going to leave that one for last. So, Par Charlie's Almanac is a great book. And

I want to underscore something that you said somewhat in passing, which is really important, and I know you know it's really important, which is the avoiding of making really bad mistakes. And one thing that Munger emphasizes a lot, you know, the right hand of Warren Buffett, and Warren Buffett, I guess, has said he has the best 60 second mind he's ever met. 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 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 very short too. It's easy to read. And you mentioned the sort of nuts and bolts. So I'm going to use this and then we'll probably jump around chronologically, but you, uh, if I'm remembering correctly, have a label in your email called OPP. Uh, could you explain for people what this means? Yes. So I think originally, well, yeah, it stood for other people's problems.

Although I made it a little nicer later, other people's priorities. And because I have a vendetta against email, which we can, 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. But then to the OPP thing, I'm like, wait, then what are these things? What am I doing? And you realize that you're just basically checking off items on other people's to-do lists. Where there's sort of in the abstract, there's nothing wrong with that.

And it's important to be helpful. And we all have been helped by and help other people. But you can end up in a situation where basically your to-do list is a composite of other people's to-do lists, and your calendar and your email can often reflect that and uh and tying it to another so one of the most important concepts is focus um everybody understands like yeah yeah focus um and i imagine something we'll probably talk more about here um but there are so many forces so people love the idea of focus and and was interesting, just going back to Warren Buffett. Warren Buffett and Bill Gates did an interview. I think it's on Netflix. It was a Warren Buffett documentary, which is great.

I also recommend. Anyway, the interviewer was interviewing both Warren and Bill and was like, in a word, what has made you most successful? They both, at the same time, without missing a beat both said focus um 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 uh highlights is there's so many like the default for pretty much anything is to unfocus you um 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 um uh if you're working within an organization pretty much everybody will be pulling on you to kind of feed the beast of the organization and so it becomes very hard to do a few things well. And so, I mean, there's a lot of great things about that book. But yeah, I do have an OPP folder, which I try to keep manageable or find ways to – I think the best is if you can find ways to be helpful but and like involve other people and actually helping so i and i have a whole team of people who um can help me respond to to those those kinds of requests so now the opp folder it's not this is not necessarily a black hole uh it's not an indefinite

archive necessarily but it's when i'll get around to it do you have a set schedule for looking in the opp folder or having other people do that for you? And what are the criteria, right? Is it that anything that doesn't come from, say, a direct report or an investor or a family member goes into OPP? Or what are the guidelines? Yeah, so I think some people would say it's feeling feel a call even when I help. So I'm not great at responding to these things. 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, do you still need this um but uh so i i would i think it's if if it is something from a person you have a relationship with um i would say you and and there's probably other factors but it's like okay is this someone who uh i know and where i where i personally would be really helpful um and they have done their homework, and I think there's certain first-pass filters like that. I would say there is no commandment from God that you have to respond to every email you receive. So if it's like a cold email,

or if it's from someone I don't know, or it's like a cold email, or if it's 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. 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, go to this blog post or do this thing. And then you don't hear back from them and it turns out they just never followed up

or just didn't do it. And so after you get burned by spending a bunch of time trying to be helpful to people who don't help themselves, you realize that's not how you want to spend your life. So you have to – 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 yeah or at least or small or big you should just at least be mindful of it a lot of people just and find themselves hopelessly busy and on this treadmill responding to other people's to-do lists and knowing no one is doing the things on their to-do list right you one thing you said about people doing their homework reminded me of this quote from Maria Popova, who writes Brain Pickings, which is this incredible site, millions and millions of readers and really long form, smart writing. And at some time,

I think she changed it to be a little more maybe sunny seeming, but she had a quote, I'm pretty sure on her Facebook page as the graphic, as the header at one point that said, if you haven't done, or if someone hasn't done the homework to determine whether it's a fit or not, it doesn't warrant the energy to explain why it isn't a fit or something like that,

which I think is a great commandment or 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? Or not using email? Yeah, I try not to use a lot of email. Because often if it's, I think email is good for quick, discreet tasks

where you're holding someone up by not doing them. But if you're trying to, uh, and then I think it's also useful to like for broadcast, like if you have something, if you have some long form written, um, direction that you want to give a group of people, um, then, then, then that's a good use of it. Um, but often when people get into these long email threads, uh, it's often, um, I mean, it's, it's sometimes really fun and indulgent to get into these big flame wars. But often, the best way to, if you get a long email, often the best response is to talk to them in person. And if you're getting a lot of little requests, it's

better to just batch them up and have some kind of weekly cadence where you can deal with a lot of quick requests without having the overhead of email. And I think these are all kind of, email is just one example of a lot of different forces that can take away, that can kind of shatter your attention or take away your time. I think one of the most valuable concepts from the effective executive is measuring your time and early understanding where your time goes. And it is kind of shocking and hilarious, but really tragic that we all think we know exactly where our time goes. But then when you measure it, you're not usually just like slightly wrong. You're like totally upside down. So, so, um, this is a really valuable exercise for anyone, but actually like keeping a log of like where

you spend your time, um, and categorizing it. I remember the first time I did this, I was like, all right, I'm running the company. It's things are going well. I probably, what do I spend my time on? Oh, back then it was probably, I was like, Oh, 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, following up on favors

or speaking engagements that didn't really do anything for the company. There wasn't, like, a lot of, like following up on favors or speaking engagements that didn't really do anything for the company. And I don't, there wasn't like a lot of like total fat like that, but, um, 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, uh, to, um, to first understand where your time goes and then make sure your priorities actually match it. I think at the end of the day, that's conceptually what you want to do. And then just understand that you're going to tend,

and then you also want to offset the tendency to be in this permanently reactive state, whether that's because you're getting emails that are other people's requests or your calendar says one thing. Usually when your to-do list gets too long, you just sort of do things randomly or just do whatever the last thing, you just respond to whatever showed up

most recently in your inbox or what blinked at you or what yelled at you loudest in the last hour. And that's not effective compared to setting your own priorities and measuring yourself against them. And this is a separate topic, but I think technology needs to do a lot better job of helping us do that because it's really hard. And then especially as you're in any kind of organization um you're gonna you're gonna the the the fires will get dealt with first and that's

that's not a bad thing um or that 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 exactly versus urgent yeah the matrix the or the quadrants i guess it was four yeah the two by two is important and urgent like you just and um 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 um that you elbow out time the important not urgent stuff because the important and urgent stuff will get taken care of but then you end up with a lot of stuff that's not important or urgent not important or not important not urgent and you

really want to like cut those down as much as possible because otherwise a lot of the fires if you actually do root cause analysis think about like why did why was this fire in the first place when you kind of climb that ladder a couple of rungs like why did this happen why this happened or why this happened because of that well why did that happen because of that, you find that just a little bit of planning would have eliminated the need to fight that fire. And it's really easy to spend your days kind of doing the equivalent of paying down a lot of high-interest credit card debt with your time by just fighting all these fires and not actually putting them out at their root. So something I do on that front now is I have a – there's a concept called No Meeting Wednesday, which I think is popular around the Valley.

Maybe it originated Facebook. I'm not sure. But we've sort of half-heartedly adopted that, and I half-heartedly adopted that for a while. But I remember there was a – I'm like, I really want to do this because there's all this planning and all these things that are important where the cost of me not creating clarity for my team is super high. And I sat down with my assistant at the time, and I was like, hey, I need to, like, please don't schedule stuff on Wednesday. Like, it's really important that I work on this particular project. And, you know, it's just not going to get done unless there's some, unless I have like a full day or like many hours of uninterrupted time. And she's like, but 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. Um, and so it's dawned on me in that conversation, I'm like, this shit, this is all important. Like, but it's not. And, and so, um, I was like, look, just, I really want, if, if, 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.

Otherwise, you lift up your head and you find six months have passed on some 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 one of the biggest mistakes that people make. One of the concepts from Effective Executive is a lot of that stuff doesn't make progress with a half-hour slot in a day of 10 hours of half-hour meetings. There's a minimum quantum of time for deep thought or deep work that you need. And so anyway, there's a lot of really conceptual, great conceptual foundations

and effective executive about your time and effectiveness and disambiguating busyness from effectiveness. And then the concept of leverage and high output management and a focus on output. So those two books have pretty much conceptually everything you need, but then implementing it in practice is a lot harder. Yeah, we're going to talk about the practice quite a bit, I think, also in this conversation. I want to circle back to a few things you mentioned because I think they're really important. The first is the Eisenhower matrix, I think it might be referred to as, which people can look up on their own time. But the correlating, in some respects, maybe exercise that I think Drucker brings up in the Effective Executive is the jar or mason jar.

And people can visualize this very easily. But if you have a mason jar, and next to the mason jar, you have a handful of large rocks that can fit into the jar. Then you have a bunch of smaller pebbles, and then you have a pile of sand, all of which has come out of the jar. If you put in the big rocks first, i.e. your most critical tasks, which may or may not be urgent, then you can fit in the pebbles, then you can fit in the sand, and you screw on the top, and it's nice and neat.

But if you put in the sand first, the whole thing falls apart, right? You cannot take the same volume of rocks and pebbles and sand and get it into the jar. And 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 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, 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, uh, really, really routinely. Um, the, the blocks of time,

actually, you know what I'm going to get? 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 get a teaser for what you'll read more about in The Effective Executive, there's an essay. I might be getting the headline slightly off, but you'll be able to find it.

Maker's Schedule, Manager's Schedule by Paul Graham. And the legendary PG, who we're going to come back to, is a good place to start. But I want to rewind the clock for a second and ask you, why did you stop the SAT online prep company? So I started the SAT prep company in 2004. And then I went back to school, finished my undergrad, and then a couple things happened. 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 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, I just 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 side projects. And now I recognize all this as burnout. There aren't a lot of good things about burnout, but sometimes it can steer the positive element is a posterior 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 is not successful enough. 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 like totally not helpful um 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 um but then i would like well one good news i started working on this like poker bot um that started and it played with real money like i like got past the security on the poker client this is 2006 so i figured out how to like make all that work and then watch kind of my frankenstein moment as the bot comes to life and starts playing on real poker tables and so this idea that you can't have poker bots was like totally false um but and and but i was possessed it was like were poker bots was totally false. But I was possessed. Were you winning? Was Frankenstein's monster winning?

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

because I was living in Boston, but then we have a little summer place in new hampshire and 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 were kind of used to me having all these side projects so they're just like i hope it's not illegal just um unfortunately that side projects had to stop because of that

like the in fall of 2006 it became like went from like kind of borderline to like very illegal to do online poker so that um that project ended but um but so what's that about uh 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 – well, the founding story of Dropbox starts with forgetting my thumb drive

and going on the Chinatown bus, which I'll get to. But before that, I kept having these problems working with my co-founder because, or collaborating with him, because we didn't have an office. Well, we bootstrapped the company, so we didn't raise any money. And we didn't have an office. We didn't work out of the same place. And we didn't have servers. We didn't have anything. So we would just email stuff back and forth. And I had to work on multiple computers, so I kept carrying around this thumb drive

and having these elaborate scripts that would back up the SAT prep company, kind of all of our files to a server. And then eventually I was like, all right, well, I graduated from college. This was about 2006, late 2006. A lot of my friends had lived in New York, and they were like, you've got to come out.

It's a lot of fun here. Just come out for the weekend. And I have a dilemma because I'm like, well, I need to get some stuff done for my company, but I also want to go to New York. And I'm like, maybe if I take the Chinatown bus, uh, 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. So, you know, you know, all the elaborate rationalizations we, we come up with. And so I'm like, okay, if I take the bus,

that's I'm, I'm green light to go to New York. Then I get on the bus and I've forgotten my thumb drive. So, and then 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 hate my thumb drive. I'm like, I hate me. But I'm like, oh my God, I just cannot deal with this problem. This is so stupid. I'm so sick of emailing myself a file. There's no question for it, so that's the right answer. Think of the physical equivalent of that. Taking an envelope, putting something in it it putting your own name in the to and from putting in the mailbox and getting it back i'm like this is what we do to like manage our files um uh that carrying around a thumb drive all the things we used to have to do and i'm like i never want to have this problem again so i on the bus um i opened up the editor and started writing some code um in python that basically was a 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 like an engineer by upbringing. My favorite classes at school, other than some of the stuff we've talked about, are like algorithms, distributed systems. 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 of things happened. So one is I like pause. I'm like, okay, I'm working on this company. I'm kind of burning out. Um, part of why is because I thought about, even if all of my dreams come true and everything we hope for happens with this SAT prep company,

then what? And I'm like, king of SAT prep. And there's nothing, I mean, I think that's fine and people need help with these things. But I'm like, that's not what I want to do. I'm just picturing this kind of 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. Um, 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.

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. So I want to bring this back to the dot, dot, dot that I left after Paul Graham. And we can certainly go in any possible direction you want to take it. But for people who don't know Paul Graham, maybe you could describe Paul Graham, certainly as close to a demigod as one can probably get among many, many young entrepreneurs and older entrepreneurs in Silicon Valley. Who is Paul Graham? What is Y Combinator?

And can you describe your first meeting with Paul Graham? Yes. So Paul Graham is best known as one of the founders of Y Combinator, which is an incubator for startups. And they were our first investors, and they also invested in a lot of great companies, including Airbnb, Stripe, a lot of them. uh paul was before starting my combinator he had written uh he was an entrepreneur himself so he started a company called via web back in the dot com or the first dot com boom and sold it and then he had a lot of really provocative and insightful essays on startups that gained a big following. And he was also one of the creators, or at least was very early in the conversation around

using Bayesian methods, using this kind of math to do 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 have figured out how to get rid of spam. Um, and that's actually how I first heard about him. But then he started writing about startups and then, um, ran this experiment that became Y Combinator.

Um, but it was actually called the summer founders program. And I was digging through some old email about it because, um, I, this was the precursor to Y Combinator. Uh, I applied with my SAT prep company to that and was rejected, but then managed to get into Y Combinator a couple of years later.

So I guess the first virtual meeting of applying to be funded didn't go well. The first in-person meeting was probably... Wait, hold on. Hold on. Pause. Why didn't the virtual meeting go well? Well, we didn't really virtually meet. It was just sort of like a college admissions thing. It's open application. Anybody who wants to submit an application for the Summer Founders Program, which is

basically, it was like the same thing as Y Combinator. You get a little bit of money and all come together. It was sort of Y Combinator version one. But I applied and didn't get in and i was super disappointed um so that didn't go well and then but a couple years later i wanted to apply again with dropbox and this is skipping ahead a little bit but um i had so i i had the idea for dropbox, started working on it, and I wanted to do YC because a good friend of mine, or for many reasons, but another friend of mine, this guy Adam Smith, no relation, who was one of my friends from college, he did YC in 2006 and had an awesome experience. And I had a front row seat to that and saw how much fun they were having. And then their company was just in a much faster trajectory because of YC. And I'm like, oh my god, I want something like that. So I started thinking about applying for YC with Dropbox. And one of the good things about coming from college admissions is you learn how these admissions processes work.

And YC was not really that different. You have a lot of people applying for a few spots. And so in addition to getting the scores and the grades and everything, one of the things you can do is try to stand out and do something kind of unique. And so I'm like, all right, well, maybe to help me get into YC, I'll try to put a video out about how Dropbox works. And Y Combinator also had their own, they had just started this new site called Hacker News, which is kind of like Reddit for startup news. And I'm like, what is, and I thought,

I'm like, I had a hunch. I'm like, what does Paul do all day? I think he probably does what most of us do, which is 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 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 J. Conrad Levinson or something like that. Something like that. It's like, how do you do that when you have no money? And so they're like all these, so the tactic of putting a video on Hacker News or creating a viral video is that was a seed that was planted by reading guerrilla marketing. Um, and so, but I made a screencast, which is like a,

like a three minute demo of how Dropbox works. Cause 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 I was pretty happy about that. And then I'm like, okay, so far the plan seems to be working.

And I'm just like, keep hitting refresh on my inbox. I'm like, I wonder if Paul has seen it. And then lo and behold, I get an email from Paul Graham saying like, hey, it looks pretty cool. But you need a co-founder because they did, especially at the time they didn't like single founders applying and I didn't have a co-founder yet. This was, this was before I met Arash. Um, so I was like, Oh God. Um, because the part, 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 two weeks.

And so I needed a co-founder in two weeks. Which is like saying, hey, I know you're not dating anyone, but you need to get married by April. Right. And so a hilarity ensued. But then I flew out to San Francisco. I'm like trying to shake the trees for any co-founder candidates I hadn't thought of because for one reason or another, all of my close friends and people that would have been the folks that I would have leaned on, like the timing wasn't good. They didn't want to do it, whatever else and so um but i i found another friend of mine i was actually getting managed to get a friend of mine interested out in san francisco um 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

um and i'm like it's a tuesday my flight it's 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 maybe I could just like drive down to Mountain View and just like pitch Paul maybe that would

I get the zip bar i like fly down 101 um and like the plan was like working pretty well i got it i i got to yc i went in the office it was as expected people were just chilling and kind of um there was some downtime and so um 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 um i just wanted you know i just want to show you something i'm working on and he's like nope i'm busy and i'm like okay look we both i'm like i i can almost see your screen i know you screen. I know you're just reading Hacker News right now. I'm actually busy. But it's awkward, so I step outside and I talk to Jessica,

who is his partner in co-founding YC together and his wife. And I talk to Jessica. I'm like, hey, look, Jessica. And I had met Jessica before. So I'm like, Jessica, I'm really sorry to bother you guys. I just have a co-founder who was looking for some feedback from Paul to make his co-founder decision. I got a flight back in four hours.

I swear I won't take more than 60 seconds of Paul's time. Do you think it's OK if I go in there? And she's like, oh, Drew, of course. No problem. Paul's time. Do you think it's okay if I go in there? And she's like, oh, Drew, of course, no problem. Paul's not doing anything. It'll be fine. So I go back in there and

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

He's like, no, please leave. I'm like, okay, thanks Jessica. Thanks Paul. I'm like, this is not going to i'm like this is not gonna 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 you were like there paul's paul's thinking about it let me get back to you well i did i did meet with the dean of admissions he just thinks i'm an asshole so that was i think he's i think he's coming around yeah that was a tough plane ride

home um but it's good training like this is you know this this is you gotta this is like the new normal if you're starting a company um so 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 i was like i have i could not have like f this up any worse if i had tried um because like now i don't have a co-founder and i'm like i might have been able to get in if i just like hadn't like maximally pissed off Paul. Anyway, now I have no co-founder, no YC, and probably no company. And I have two weeks left to resolve this. Or maybe a week left to resolve it.

But anyway, not a lot of time. So it was bad. I was like, I don't really see how this all lives happily ever after. So then what happened? But my shaking the trees in San Francisco did help. So I met a guy named Kyle Vogt, who I'd met at the MIT Entrepreneurs Club. So he's an MIT student. He dropped out. He had just dropped out to do Justin TV, which became Twitch. And then Kyle then later started Cruise, which did great.

So Kyle has done well. And then I was complaining to Kyle. I'm like, hey, Kyle, I need a co-founder. Is there anyone you'd recommend? And he recommended me to, it turned out that Kyle and Arash were floor mates at his 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 a senior undergrad at MIT, computer science student. And he was like, hey, I got this email from Arash. And it said, hey, I saw your video on Hacker News. And Kyle said you're looking for a co-founder. Maybe we should talk.

And then it was kind of insane. We met in the student center. Maybe we got coffee one more time. And then he drops out of school. He's like a senior. He drops out with a semester left. 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 against all odds, Arash and I team up. I think Paul forgot about his meeting with me or didn't put the two together. So we did our interview and 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 um we come back to the car our our car got broken into and our laptops got stolen oh god but fortunately all of our stuff was on dropbox so we were like patient zero for all this and then we got the happy phone call from from paul saying hey we want to fund you guys and and i mean i i don't know it was it was nuts 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 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. I mean, certainly Dropbox has done incredibly well. At what point did you go to Paul's office,

knock, knock, hey, Paul, like in brackets, now we're friends. By any chance do you remember when I came in during Tuesday, on a Tuesday not too long ago, did you ever bring that up with him or did he learn about it through some other means? I like to remind him about it every year or two. First, he's totally embarrassed.

He didn't put any of these things together. He didn't know. He didn't remember it. He's like, I was so awful at this app. Mostly, it's just they they both paul and jessica turn 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 uh it's all i mean it's all good i would have done this yeah of course him like yeah yeah well he did tell you i'm busy right yeah i was super obnoxious but

some was drop it was dropbox the original name of the company yeah it was wow so so just from day one you had the name that stuck for you getting the domain it was get dropbox.com getting the dropbox.com domain name was oh my god that was a that was a journey um so there was a good 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 the this story is but 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 yeah so i i remember get dropbox yeah so arash and i fell out so 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 asked 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 play games and um so back in the day these things were called land parties um they are about as cool as they sound. And you all show up and play till sunrise and so on. But you bring a bunch of people together, and often someone doesn't have the right maps or the right patch or the right whatever. And so we had a convention.

You just create a folder called your Dropbox that's shared and writable by anyone, 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 what the name before i was i was busy photoshopping some, the name before, I was busy Photoshopping a logo. The initial iteration of it was Folder Anywhere. Catchy, catchy.

Yes, 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 is like a literal folder or something it like totally inane and then i start and i'm like and and i you know believe it or not folder anywhere.com was actually available so i I was the proud owner of folderanywhere.com. Then I did a search, and I found there's a company called Files Anywhere. And I was like, no. Now I can't name it folderanywhere. And so 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. Folder Any anywhere is taken. Like maybe I should just, you know, maybe I should call it Dropbox like from the, you know, from high school, from LAN parties and he's like, okay, whatever. And then at Dropbox.com I'm not available. So I got get Dropbox.com, I'm not available. Uh, so I got get Dropbox.com, but then, um, so we just lived with get Dropbox.com for a while. I tried to, you can sometimes look up who owns a domain and contact them.

And so I actually did, I managed to give the guy a call. Um, and I'm like, Hey, are you Dropbox.com? You know, are you, are you using it? And the guy was like, uh, Yes, I'm using it for a project I'm like, okay, well do you have any interest In selling it or Coming up with some kind of arrangement? He's like, no I'm like, okay

Cool So that's February 2007 And then we get distracted With the whole getting into YC Finding a co-founder, all that, doing YC And then we move distracted with the whole getting into YC, finding a co-founder, all that, doing YC. And then we moved to San Francisco in September. And I'm like, we really need to get this domain name.

And unfortunately, Arash and I had totally fallen in love with it. So we kind of only had one plan. By the way, that's called a great uh negotiating position yeah awesome about as well as you'd expect so we i'm like well since the finish zip car 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 pleasonton 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, God damn it. We would get off the phone and I'm like, okay, goddammit. We get off the phone, and I'm like, alright, Arash, let's just show up at this guy's house. Let's just see what happens. So, jump in another Zipcar. We go to the corner store and get their most expensive bottle of $20 champagne we could get. Get in the Zipcar and go to his house.

It's like 9 at night so i don't know for some 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's kind of shocked kind of amused like lets us in um we have a we start talking he's like we're like hey look you know we we're we're pretty serious about this thing we're doing you know we'd love um you know 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 obnoxious way just like you know but but at least consider this alternative where you know we use Dropbox.com. We've got some really good folks who are excited about this and involved, whether that's Y Combinator.

We've just gotten funding from Sequoia, our first venture capital investor, who's one of the best in the world. And so we're like, Sequoia's the best thing. Oh, you told them that? Yeah. All right. Yeah, we're just really building up our leverage here. So this would be called hemorrhaging leverage. Although at the same time,

the frameworks don't completely account for everything. Because if you don't actually help them understand why they should be interested, and you hold all your cards to the vest, then nothing happens. And that's what we've experienced over the last seven months. So we're like, okay, so at least sketch out a case that a reasonable person would look at and be interested in.

And then he's like, cool, it's interesting. I got to talk to a friend. And why don't we touch base soon? And I'm like, great. It's like Friday. I'm like, it was like a base, uh, soon? And I'm like, I'm like, great. Well, it's like Friday. I'm like, well, it was like a Friday night, I think. And I'm like, we'll be, we'll be back on Monday. Um, 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 has 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. And we're like, are you kidding?

Is this for real? Like, no. I'm like, I'm like, where is this going to go? Are you going to like are you going to bequeath this domain to your children? Like, what the hell? But he was just like totally wouldn't budge, and so that was a much sadder drive back. So then this guy,

and then there's just kind of nothing for a couple years, or for a year. And then we launched Dropbox publicly, and then all these confused people start going to Dropbox.com and presumably start trying to get into the beta. This was later in the year. He starts getting all these emails from people, I think probably March 2008, who were looking to get into the dropbox beta um and then he he does god he and i'll end the story in a reasonable amount of time but we like so he 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 there's a no it went from

like a godaddy parking page to like a google adsense for domains page um 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 going to do about this? Our investors think we're idiots for not changing the name. We're doing all these pointless branding exercises that

did not go well to try to find an alternate name. I'm just like, oh my god, what are we going to do? The answer was, read the federal copyright code and trademark code. And I became kind of an expert in cyber trademark law. I got an armchair expert in this stuff.

And it turns out you can't just get a domain from someone for no reason 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 but it is also illegal for someone to intentionally confuse um uh confuse customer can confuse your customer so um i can't just say that we're, I can't sell paper towel, or I can't sell 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 um but he was now making money from infringing on our common law trademark rights and so i'm working with this crazy trademark like 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. We weren't just trying to push him around.

He was trying to profit off of confusing our customers. So we got on our high horse after that. And that was a comical whole experience. But eventually he's like, okay, okay, okay. There's no point to have this lawsuit.

I'll give you guys or I'll sell you guys the domain. I'm like, okay, well, we can offer you stock or cash. He's like, I'll just take cash. So we paid him 300 grand, got the domain, lived. 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 I, we offered him stock at that, like it would have been at the seed round.

Oh my God. Worth like multiple hundreds of millions of dollars today. Oh, man. I think what you can take away from this is there's just no manual for that, right? You've got to 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 got to 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.

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 the computer science slash hacker subset. 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 something along the lines of, Oh, my God, you're just a rounding error for Yahoo. And it was so insulting that Alexis took, you are a rounding error, I think it was, and put it on the wall in the office to motivate. But that is one of several different responses that are possible. There are certainly people who would be crushed by that. It could be the end. And I don't remember exactly where this quote is from,

but I want to talk about when this came out and what the self-talk was. So there's an article being written about Dropbox and I think the quote was, quote, fortunately, the Dropbox founders are too stupid to know everyone's already tried this, end quote. Yeah. So when did that happen? And how did you and anyone else involved respond to it?

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 that 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 were like, I would use something like this, it's good.

And it was really encouraging. So on the one hand, half the peanut gallery is saying that. The other half is 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 going to kill us. And here's why it's never been a business. And here are all these other ones that have never succeeded. And the things I agreed with him. 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 through to Mount Doom. That's our little 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, oh, just ignore it all. But you kind of have to be balanced. So on the one hand, we did get encouraging feedback in the beginning. So people were like, Oh, just ignore it all. But you, you kind of have to, you have to be balanced. So on the,

on the one hand we did get encouraging feedback in the beginning. So people were like, drop, this is cool. I will use this. It sounds great. Um, you know,

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 do 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 were a bunch of milestones. But it was sort of a continuous process more than like, oh, it was just 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, um, you have to have, you have to sort of have alternate, you have to have both thick skin and thin skin or 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 going to have some kind of blind spot and you're going to, you're going to miss some important information. So, um, 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, um, when to be a little bit dismissive or not listen to everything. And part of what helps with that is having conviction,

and conviction that comes from being able to think from first principles. And pay less attention to people's conclusions, 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 going to be successful because people have tried it a million times. And that is true. And anybody who, that's like factually true.

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 um if you study history of technology or history business you realize okay that that argument is not in and of itself um causal um so what you want to answer is like why is that incorrect it's like well actually

um there are there are a lot of good ideas that are bad ideas for a while because the timing is wrong, but then the timing becomes right because of some discontinuity in tech. Quotes like The Innovator's Dilemma or others will illustrate that. If you understand, that's why it's important to build these mental models because you're like, all right, this is my framework for how the world works and I keep refining it. What these people are missing, the key conclusion from that, that just because something has happened, like has failed before, doesn't mean it will always fail in the future. It can still fail, but that kind of conviction came from an understanding or a belief 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. 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've talked about. But then that doesn't make it feel any better when people are like, your idea sucks and you're going to fail. Or even worse than that, like you are stupid, right're really yeah at super ad hominem right um yeah people are not so first of all i think you have to have a sense of like this is normal um like you just don't take it too personally because that's the thing you want to take it uh you do want to take you want to receive the feedback and like try to extract the kernel of that's the thing. You do want to receive the feedback and try to extract the kernel that's useful from it, but not feel obligated to accept the whole thing.

I think more broadly, you just have to, whether it's getting criticism or just a lot of the thing. I think one of the harder things about running the company in general was I just remember being in the beginning being like oh my god like all right now we uh 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 like that million dollar it's great to kind of cash that check but oh man they're going to be looking for that money back at some point like what are we going to do um and so that's not there wasn't the i mean there were probably a lot of things going on in my head at the time but and then like like, oh, my God, I've never really built a successful company before. 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 is just going to go faster and faster until like I'm violently thrown off of it. Like, how am I going to deal with that? And 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 had like a, 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. Um, but then interestingly that the, 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 we put that out there. And I'm like, if I had a million dollars after taxes for six months of work, I'd consider that a pretty good deal. Um, so, um, so, but, but, but more on the, the, the, the more on just like that, what do you do when you're like, Oh my God, this is like pretty uncomfortable. I've never done anything like this before. Um, I might screw it up. You need, so your instinct

will to be to, um, run away from that feeling. And what you need to learn to do is run towards it because that's just going to keep to do is run towards it. Because that's just going to keep, keep happening, keep happening. I'm like, you know, we're gonna drive and show up at this guy's house. I don't know. So maybe we'll get arrested. I don't know. But we're gonna do it. I don't think that's the best example. There's just so many things where it's like, you just got to kind of figure it out and keep going. And Ben, one of the great things from that, 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 the 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 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 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. Um, I think that's,

that's pretty important. And then second is, all right, you have to, now it's, it's, everybody likes the idea of growth and pushing yourself, but you also have to take care of yourself. Like, um, you have to find ways to metabolize stress and avoid burnout. Um, and for some reason, people just, they just use the one tool of like pushing themselves harder and then they break. Um, and you know, you wouldn't do that to your your car you wouldn't do that with like a musical instrument so why would you do that to yourself right so um just to just to pause for a second i i 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 uh Uh, I mean, it seems like you have just as a component of that, a, a, a physical practice to care for the machine, so to speak. Yeah. I wouldn't say I'm the best like athlete by any stretch, but I, but it's really important that you have to do enough

so that you don't break down. Um, and so, and, and you got to figure out what that is for you. And, um, and I know that's something you really care about. And the advice you have to offer your readers is going to be much better than whatever advice I have. But you need to do something, some kind of routine, and stick to it. But just the basics of, I think some of the dumbest advice that people get is not sleeping or wearing, or just pursuing this idea that that successful people somehow work like 70 80 hour weeks and that's the norm um 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 lack

of awareness about where they're spending their time or lack of effectiveness if they need um if their only tool in the shed is like work more hours, right? Because just think about that. Like, you know, there, that, that is, that has a ceiling in terms of how much of an advantage that can give you. Like, yes, you want to work hard. Um, 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 going to have outsized results. And you also, I mean, so there's, 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, I mean, they have crunch times or they're super busy, but they otherwise have a work week that looks more normal than not. And so that was something I didn't realize when I was starting out. But the basics of sleep, eating well, self-care, exercise, putting it on your calendar, not just wishful thinking and hoping it'll sort of happen in the spare moments. Like if you can't see these things on your, if you can't see your priorities in your calendar, if you can't see your gym time on the calendar,

it doesn't exist. Totally. So, 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. Um, the self-awareness is pretty important. Um,

and being willing to like shine a hard light on yourself, um, and embracing that. So for me, coaching has been super helpful coaching meaning you have like an executive coach or i've had different ones over time um and and and really and like i go through the experience i'm like i'll give this a shot some of my friends have had um i have spoken positively about it um but it's a little – I remember my first coaching experience. They do the 360, and then you sit down and you do your review of your results. 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, is that fair to say? Yep. Well, you get all this feedback from all these, you know, everybody you work closely with. So it's kind of overwhelming. Um, cause you get a lot of it. Um, and it's not all good. So, uh, 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 it's not fun. It's at least not fun. It's not something I look forward to, but it's important. So because you need to know, like it's much better to just just know and be able to do something about it.

Ben's been a great friend and mentor. He told me a quote that one of his mentors told him, which is, God gave us all weaknesses. It's a blessing to find out about them. Hmm. Yeah. Sobering. You know? But I went through that yeah i just remember my first

first coaching experience briefly like you know sit you down they're like first page is usually like here are your strengths and i'm like okay he's like my coach was like you are really you really really care about people you love building great relationships and i'm like yeah okay yeah that sounds that sounds good um you're really creative you like new ideas i'm like all right i'm enjoying this coaching thing so far uh 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 and then flip to the next page right now like it's never weaknesses development areas that's right or operating opportunities for improvement yeah so i'm like let's hear about some opportunities um he's like you are really conflict avoidant um you don't uh make hard people decisions uh people don't know what you do like

where they stand i'm like okay he's like uh you're unreliable. You drop, you drop balls. Um, uh, you're not paying enough attention to the things that are important. I'm like, okay. And he's like, um, and you suck at planning. Uh, 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 and you like people to be happy, so you avoid conflict. You are creative. You like new ideas, so you don't pay attention to the routine stuff. You're comfortable in chaos, so you don't plan. These strengths are all like their own weaknesses in disguise.

And there's no one who's like 10 out of 10 on everything and that's that's why um so 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 get your weaknesses to a point where they're not like destroying the company um but generally you want to play to your strengths and that's one of the key effective executive tenets um but other than that uh but then i think just self-aware, trying to understand yourself on all kinds of different dimensions is really valuable. I talked about the Enneagram in your book. It's sort of like, I would call it a useful Myers-Briggs. So most people are familiar with Myers-Briggs.

It's a personality typing system, but then you read it it and it's like reading a personality quiz on the internet. You sort of, you remember you had some letters and there's like some stuff, but you don't actually do anything with it. 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 t i was i was super skeptical i was like this sounds like a cult um and it kind of is but um it's been very helpful both to do individually and with your team because it just you sort of you what you learn is like okay here are the here are my blind

spots i was like i'm an enneagram 7. These are like totally textbook strengths and weaknesses of a 7. They like new things, they're comfortable in chaos, but then they can become distracted and unreliable. Conflict avoidant, things like that. So just knowing, one way or another, you always want to have an accurate map of what you need to work on. How were you introduced to Enneagram? Well, so it was through my co-founder,

but then Arash was introduced to it through a guy named Gentry, who was the founder of Mailbox, who worked with us for a while. So let's call it three or four years ago. And then Arash was like, you're going to love this. It's great. And I'm like, it sounds super weird. But he was right. So it's been super helpful. 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? Sure. So I did the commencement speech for MIT back in 2013. And the whole premise was, I'm like, I'm 30. I don't really, can I wait 20 years? I'll say something way more insightful then. But I'm like, all right, well, I kind of, the prompt, the prompt I came up with 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 about like dropbox or even just other side projects like the poker bot like i am both most productive and happiest and most successful and like it's like when all those things line up or when the thing you're obsessed with overlaps with something the world really needs um uh or values so um but but like don't settle like find something that uh the tennis ball is sorry like what is it where does the tennis ball come from i had this like really lazy fat dog growing up um who would uh but when you showed her food or you showed her a tennis ball, she would just go nuts. And so you'd throw a tennis ball for her. It was like watching a ham running on twigs or something.

It was just bizarre. It was just funny like 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 i'd not overdo it but like but the point is like find something that um 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 um then the circle concept is really there's a saying um by a guy named jim rohn that you're you're an average of the five people you spend the most time with um and i found that to be super true so and then so the and the upshot is like choose choose wisely 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 capable, but then also you get jealous and you're like, oh, I, you know, I, I want to be that good. And so you, 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, um, being in Y Combinator with

other founders, like friendly competition there, or with my friends who were starting companies being in San Francisco, all of those contributed massively to, um, to us, uh, to us making it. Um, and then finally 30,000, uh, is, is, 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. Um, cause I think I just moved to San Francisco and I was, and I, and I was just like, I was like, okay, yes, this is like a clinical truth, not terribly interesting. Because I think I just moved to San Francisco and I was just like, I couldn't sleep. So I was just like on the internet reading stuff. And I came across that and I remember being like, huh, okay. And I opened the 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 down. 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 um 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. You're not an average of all your successes and failures. You should change your mindset to life and also just think of it more as just making a story that's interesting, not just trying to be perfect, because I think that's a trap that a lot of people fall into. So anyway, when I thought about, you know, if you were to play everything over again 100 times, who knows what would happen. But if I could just hand back a cheat sheet, that's what I would put on it.

That's what you'd put on it. Tennis ball, circle, and the number 30,000. Well, Drew, I know you have a very, very busy, uh, time ahead of you and I'm sure today is no exception. So I'm gonna let you get back to your day, but do you have any closing comments, asks, uh, suggestions or anything else for people who are listening to this? Any, any kind of parting comments before we wrap up? Let's see. So I think, yeah, just don't forget to have,

like, don't forget to have fun. And I think at the end of it, you want to have, like, 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, what you want to do is write an interesting story, not like a perfect story.

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 uh 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 uh, uh, you know, if you're part of the human condition, it seems like that is going to be a component, uh, one way or the other. Uh, well, Drew,

thank you so much for the time. I always enjoy chatting and hopefully we get to, uh, hang again in person sometime soon, but I appreciate you carving out as much time as you did to, to share your stories with everybody. For sure. Well, thanks Tim. It's a lot of fun. And for everybody listening, we will have links to all of the books mentioned, everything else that, uh, that, that drew may send our way as well in terms of resources,

all the things that we discussed, hacker news, et cetera, in the show notes, which you can find as always at Tim dot blog forward slash podcast with all the other episodes. And until next time, thank you for listening. Hey guys, this is Tim again.

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