#334: Drew Houston — The Billionaire Founder of Dropbox

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.

So yeah, going way back. Well, first I was definitely that kid who was on computers. So my parents, I remember just toddling into my living room and seeing this glowing orb and all these buttons, and those were two things I really liked when I was three. I guess still do. And so for sure I was super interested in computers and technology, and started out by playing computer or video games. Basically that was like the first interest, and then I wanted to make my own computer games. I thought that my career was going to be starting a computer game company, and I thought that there would be nothing better than that. So I was that kid. I learned programming at an early age. I grew up just outside of Boston, so grew up in New England. And then on my way to MIT, I really liked math, science. So kind of out of central casting in terms of being a computer science student. And then yeah, my first career was babysitting, but then I discovered that you could be paid to program. And then that caused a bit of a career shift, which we can talk about.

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

Yeah, I think somewhere in the middle. So I wasn't reclusive. I had a really great group of friends. I wasn't captain of the soccer team either. I think I did academic decathlon, which is just a fascinating thing that it exists. But you know, more of a math elite than an athlete athlete. So, but I was not like super social, but I had a good group of friends. And then for sure as I went into college, I became a lot more social and just curious about humans and human behavior. But otherwise I think people, I would have been known in class as always doing, like I think there were those superlatives in yearbooks. I think I was like most likely to start a company or most likely to be like...

Yeah.

Yeah. So it was about my junior year of undergrad. I took a leave of absence because I had an idea for a startup that I wanted to pursue. So I took a year off to do that. And what I noticed was that this was back in 2004. So I was maybe 21 and the SAT was changing, or I started an online SAT prep company. And 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 obsolete. And who really wants to go to some classroom at 8:00 in the morning on Saturday? Anyway, we can build a much better experience if we do it online.

So, I was really excited about starting a company and we jumped into it and I think we met in a Chili's and like we're planning world domination and figuring out how do you incorporate a company. And so it's a really great introduction to the world of starting companies. And then the more I learned about the mechanics of starting a company, the more I realized I didn't know about business. And I knew a lot about engineering and programming, and I had worked at startups. But when it came to one, there was a fog beyond just building the product. And so I was like, all right, we're going to need, I know like sales and marketing and strategy, like these are all things, and all I know is I don't know a lot about them. So, I had the highly scientific method of I just was like, all right, I'm just going to go on Amazon, type in sales, buy the top three or four books, and just do that for every category. And then I had a couple book recommendations from one of the founders of one of the companies where I worked as well. But it was great and it was an important combination. So if 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 like somewhere you just read the book and you're like that's interesting but then don't use the knowledge.

But 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.

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, you know, I went through my high school and there were a lot of great books that you read as part of your high school curriculum, but then I stumbled across a book, Emotional Intelligence by Daniel Goleman. And I was like, oh my god, this has just, it's non-fiction. But it spelled out something that I just didn't know you could kind of break down in a logical way. And suddenly I have this understanding about the world that I didn't have before. And so that was important because it was sort of one of a bunch of early examples that anything is trainable and it got me on a path to developing what we now call a growth mindset. And realizing that it's possible to learn about these things where you have no experience or where it's easy to be like, oh, I don't know about that or I'm just an engineer, I'm not a business person. And kind of shatter that misconception.

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 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 culture meme at MIT. And I think it just creates a huge blind spot for people. Both because it makes them less effective, but it's also like the stuff is actually really interesting. And 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 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 like 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, da da. And spelling it out in a way where I was like, actually, this is a lot more straightforward than some of the theoretical math classes I have to take. And it's a lot more applicable to my daily life. And so, I started to, 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.

Yes. So, in that negotiation class, there's a book called Getting to Yes, which is about principled negotiation. And I still think about a lot of those, I still think about and apply a lot of those concepts today. And then some of the, so part of it was just doing a random walk on Amazon, but I also became friends with the founders of the companies where I worked. And during lunch breaks or at other times I'd go chase them down and bug them and ask them questions about like, hey, how do you start a company? Do you have any book recommendations? Just making that, 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 was Innovator's Dilemma by Clayton Christensen. It's a book about how businesses get disrupted and why, 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 products. It's like how do technology products make their way from early adopters to the mainstream?

I have. I mean I'd say there are a lot of, you read a lot of books, not all of them are as good as the Innovator's Dilemma, but then yeah, it also helps to revisit some of the classics. Innovator's Dilemma actually, both of those books are good examples. So yeah, I do revisit them because again, when you're 21 and you've never had a real job, you know, you're reading this book and you sort of get a general sense for things but you don't really deeply understand the concepts. And then coming back five years later, ten years later, you can really absorb a lot more of the material. So I read a lot of books in general and then when I'm reading a book, I'll triage. I'm like, okay, is this something I need to study? Is it something that's interesting or is it that I might need to know something about or is it just fun? And if I'm like, I need to study this book, then I approach it pretty differently than if it's just entertainment.

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.

Yeah. So, for the sake of starting, or if the subject of the class were starting a company, or evolving from being an engineer to being a 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 back, particularly back in the 80s and early 90s. So Andy was an engineer, one of the founding engineers, and then rose the ranks at Intel and became CEO. So he's lived this path. And when I read about or I heard about this book and it was introduced to me as the best book on management ever written. And I agree and it just breaks down all the mechanics of, okay, how do you run a team? How do you break down a goal into sub-goals? How do you, just the 101 of running a team and running an organization and a focus on output and results and how do you measure people and just a lot of nuts and bolts things, 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, it's very easy to mistake effort for effectiveness. There are a lot of different phrases for this, like to confuse motion for progress, but it's really about that idea. So how do you know if you're being effective? What practices, and there's a bunch of practices that you can adopt that make you more effective, and then how do you avoid the sand traps of things that feel productive but aren't actually. And how do you dissect or unpack the case where we all have the same number of hours in a day but some of us seem to accomplish a lot more than others. Why is that and what can you do instead? So The Effective Executive covers a lot of that ground. Those two I think of as kind of like textbooks. Like you want to study them, you want to take notes, you want to really chew on the material.

Then I think there's a lot of other tactical things about starting a company. I'd say some more of a favorite book that's more about the experience of running a company is Ben Horowitz's book The Hard Thing About Hard Things, which is kind of just shows you kind of the mess and adventure and the crazy highs and lows and like what the human experience is of actually having to do this. And then I'd probably zoom out and get a little more philosophical. So a couple favorite books are Poor Charlie's Almanac by Charlie Munger. So Charlie Munger is Warren Buffett's longtime business partner. And this book is really interesting because one of the things about being a CEO or taking on big responsibility for anything is you have to make a lot of decisions about a lot of different things and do it quickly and be right. And so how do you be right about tons of different things, especially if you don't have a lot of life experience? Like how do you train up that skill quickly? I mean that's really called wisdom or judgment.

And so it's like how do you grow wisdom or grow judgment quickly? Poor Charlie's Almanac is a great example of 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. And he argues that a lot of really wise and effective people develop, or they basically build a catalog of mental models and concepts, whether that's something from, and basically assemble all the best ideas from all the different disciplines and then figure out how do you apply them in life. And so for example the concept of a BATNA and leverage, that might be a concept that can be applied in all kinds of different situations, or comparative advantage from economics, or you could go on about these different concepts. But then figuring out how do you internalize them so well that you're able to figure out, okay, these are what matters in these situations.

And then how do you avoid, how do you particularly avoid terrible decisions, but really how do you build enough of, he calls it a latticework, how do you build enough of a latticework of these mental models so that you know which ones to apply when and that you find yourself most of the time being able to make good quick decisions. And then also on the philosophical front, so Zen and the Art of Motorcycle Maintenance.

Mhm. Yep. So you talked about engineers who dismiss all these things that can't be fit into an algorithm or that don't have some kind of mathematical rigor underpinning them. Zen and the Art of Motorcycle Maintenance is about that, just that question of okay you have this whole rational world which can explain a bunch of stuff but then you have the whole aesthetic world which can't be boiled down to a formula and they both exist and they are both useful in different cases but they don't tend to get along. And so what's up with that? And it's a really great book about those kind of concepts and I think developing an appreciation for both, developing both your left and right brain, to use that analogy, I think is really important if you're running a team or growing a company.

Because there's a lot of stuff where it's a lot about technique and data and a lot of things like strategy or the engineering kind of fall into these if-this-then-that kind of reasoning. But then a lot of the hard part of the job is really about people and what motivates people. How do you paint a vision of the world that's exciting for people? How do you build good relationships? How do you develop products with taste? Those are things where you're not able to reach as much into the more rational or engineering bag of tricks. So I think developing both sides of your brain or developing an appreciation for both is really valuable. Maybe one more. So Principles by Ray Dalio, who I know was a recent guest. I think he's got really concise and good thoughts for, all right, how do you sort of approach all the, how do you approach life? So, I would include a mix of different kinds of things. I'd have more instructional books, more philosophical books, more story and history kind of books.

Right, and Ben Horowitz of Andreessen Horowitz and many other things prior to that.

Yes. So originally, well yeah, it stood for other people's problems. Although I made it a little nicer later, other people's priorities. And because I have a vendetta against email which we can dig into, but I 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, right?

But then to the OP thing, I'm like, wait, then what are these things? Like, what am I doing? And then you realize that you're just basically checking off items on other people's to-do lists.

Where 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 tying it to another, so one of the most important concepts is focus. Everybody understands like, yeah, focus. And I imagine this is something we'll probably talk more about here. But there are so many forces.

So, people love the idea of focus. And it was interesting just going back to Warren Buffett. So, Warren Buffett and Bill Gates did an interview, it's on, I think it's on Netflix. There's like a Warren Buffett documentary, which is great. I also recommend. But anyway, the interviewer was interviewing both Warren and Bill and was like, all right, in a word, what has made you most successful? And they both at the same time, like without missing a beat, both said focus. And so if we all, and it seems so obvious, like we all know why focus is important, but then one of the things that The Effective Executive highlights is there's so many, the default for pretty much anything is to unfocus you. And that's true of your inbox. Your inbox is just not prioritized. It's just going to, you basically get all these requests that are other people's priorities. If you're working within an organization, pretty much everybody will be pulling on you to kind of feed the beast of the organization and so it becomes very hard to do a few things well.

And so I mean there's a lot of great things about that book, but yeah, I do have an OP folder which I try to keep manageable or find ways to, I think the best is if you can find ways to be helpful but then involve other people in actually helping. So, I have a whole team of people who can help me respond to those kinds of requests.

Yeah. So I think some people would say, feel even when I help. So I'm not great at responding to these things. So, I mean, it might be if it's something that's not a priority, then I'll try to respond in days, but sometimes it's weeks, sometimes it's months, sometimes you'll get a response that's like, oh yeah, it's seven months later. It's like, oh, here, do you still need this?

But so I would, I think it's if it is something from a person you have a relationship with, and there's probably other factors, but it's like, okay, is this someone who I know and where I personally would be really helpful and they have done their homework and it's like, I think there's a certain first pass filter 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 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, you can often tell by the question, as a person, many if not most of the requests will be something where the person could just do a little bit of homework and get a good answer.

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

Yeah, I try not to use a lot of email because often if it's, I think email is good for quick discrete tasks where you're holding someone up by not doing them. But if you're trying to, and then I think it's also useful for broadcast, like if you have some long form written direction that you want to give a group of people, then that's a good use of it. But often when people get into these long email threads, it's sometimes fun and indulgent to get into these big flame wars, but often the best way to, if you get a long email, often the best response is to talk to them in person. And if you're getting a lot of little requests, it's better to just batch them up and have some kind of weekly cadence where you can deal with a lot of quick requests without having the overhead of email.

And I think these are all kind of, email is just one example of a lot of different forces that can take away, that can kind of shatter your attention or take away your time. I think one of the most valuable concepts from The Effective Executive is measuring your time or understanding where your time goes. And it is kind of shocking and hilarious but really tragic that we all think we know exactly where our time goes. But then when you measure it, you're not usually just slightly wrong, you're totally upside down. So this is a really valuable exercise for anyone, but actually keeping a log of where you spend your time and categorizing it. I remember the first time I did this, I was like, all right, I'm running the company, things are going well. What do I spend my time on? Back then it was probably, I was like, oh, I spend my time on product and recruiting. And when I actually did the inventory, I was spending like no time on those things. There was a lot of OP back then, like just responding to, following up on favors or speaking engagements that didn't really do anything for the company.

But it just, what you find is you write down your priorities and you look at your time and you find that things are totally mismatched. And so any mechanism you can to first understand where your time goes and then make sure your priorities actually match it, I think at the end of the day that's conceptually what you want to do. And then just understand that you're going to tend...

And then you also want to offset the tendency to be in this permanently reactive state, whether that's because you're getting emails that are other people's requests or your calendar says one thing. Usually when your to-do list gets too long, you just try to do things randomly or just do whatever the last thing you just respond to, whatever showed up most recently in your inbox or what blinked at you or what yelled at you loudest in the last hour. And that's not effective compared to setting your own priorities and measuring yourself against them. And this is a separate topic, but I think technology needs to do a lot better job of helping us do that because it's really hard. And then especially as you're in any kind of organization, the fires will get dealt with first and that's not a bad thing, or that's necessary. You can't not put out the fires.

Yeah, the matrix, or the quadrants, I guess it was four, yeah.

And 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 at 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, please don't schedule stuff on Wednesday, like it's really important that I work on this particular project and it's just not going to get done unless I have a full day or many hours of uninterrupted time. And she's like, but, she's like, but blah blah blah has this and it's important and blah blah blah has this and it's important and blah blah blah has this and it's important. And I'm like, there will never be a day where there isn't something quote important, you know, coming up. And so it dawned on me in that conversation. I'm like, this is all important. Like, but it's not. And so I was like, look, just, I really want, if it is important just schedule it on Saturday. I'll come into the office. I'll do all those things. And then miraculously those things kind of ended up doing themselves. And adopting no meeting Wednesday was utterly transformative in terms of actually being able to think and make progress on the most important things. Because otherwise you just lift up your head and you find like six months have passed on some important, on quote important priority of yours and there's been no progress. So think about how do you develop systems and how do you build in time for reflection and elbow out the time for you to think and set direction. And I think that's probably one of the biggest mistakes that people make and one of the concepts from Effective Executive is like a lot of that stuff doesn't make progress with a half-hour slot in a meeting of ten or in a day of ten hours of half-hour meetings. Like 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 great conceptual foundations in Effective Executive about your time and effectiveness and disambiguating busyness from effectiveness and then the concept of leverage and high-up 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.

Yep.

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, after graduation, I started working as an engineer at a network security company. And I was still moonlighting on the SAT prep company. But I found myself in a situation where it was just harder and harder to make progress on the SAT prep company. And I wasn't really sure what was going on because I just felt like it took more and more willpower to pedal, or I felt like I was, I don't know whether it was because I felt like I was pedaling harder but not getting anywhere or one way or another. But over time it took a lot more willpower to work on it and so I found myself procrastinating with all these side projects. And I mean now I recognize all this as burnout. And a positive, there aren't a lot of good things about burnout but sometimes it can steer, the positive element is it can steer your attention to things that are more worthwhile. But then I was worried because I'm like, oh my god, I'm so unproductive and I'm wallowing in this guilt. I was raised Catholic, so like this Catholic guilt of like not, you know, I'm not working hard enough. This company's not successful enough. And it's just totally not helpful. But and so I'm like, oh my god, am I broken? Like, am I not capable of working hard? What's wrong with me? But then I would like, well, one good news, I started working on this poker bot that started and it played with real money. Like I got past the security on the poker client. This is 2006. So I figure out how to 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 totally false. But I was possessed. It was like...

Well, I mean Frankenstein was like not too smart in the beginning. So like there's some, the thing starts moving the mouse and playing the hand then gets confused because 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'm like, my family's like, okay, you know, come up this weekend. We're all going to be at the lake. And I'm like, okay. And then I get to the lake and I start unpacking my trunk and I've had like three monitors and 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 you know. Unfortunately that side project had to stop because of that. It like the poker in fall of 2006 it became like went from like borderline to very illegal to do online poker. So that project ended. But so what's that about? What I took from that was like well first I'm like I'm not broken. I'm super capable of working hard. It's just like I need to find something that I'm really motivated by. And so that was a relief. And then along the way, so I continued to work on the SAT prep thing, but then the kind of the founding story of Dropbox was, well, I had to use, 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 our, the SAT prep company, kind of all of our files to a server. And then eventually I was like, all right, well, I want to, I had graduated from college. This is about 2006, late 2006. A lot of my friends had lived in New York, and they're like, you got to come out. It's a lot of fun here, you know, just come out for the weekend. And I have a dilemma because I'm like, well, I need to get some stuff done for my company, but I also want to go to New York. And I'm like, maybe if I take the Chinatown bus, or if I ride the bus, I can have four and a half hours each way. So then I'll have ten hours, should be enough time to do what I need to do. You know, the elaborate rationalizations we come up with. And so I'm like, okay, if I take the bus, that's green light to go to New York. Then I get on the bus and I've forgotten my thumb drive.

Yeah. Back to self-flagellation. I'm like, I can't, I'm like I keep doing this. I suck. You know, I'm not like, I hate my thumb drive. I'm like, I hate me. But I'm like, oh my god, I just cannot deal with this problem. I'm like, I never, this is so stupid. Like I'm so sick of like emailing myself a file. Like what is the question for which there's no question for which that's the right answer. I'm like think of the physical equivalent of that. Like taking an envelope, putting something in it, putting your own name in the to and from, putting in the mailbox and getting it back. I'm like, this is what we do to manage our files. That carrying on a thumb drive, all the things we used to have to do. And I'm like, I never want to have this problem again. So, on the bus, I open up the editor and started writing some code, in Python that basically was this seed that sprouted into Dropbox. But it's weird and I was just totally possessed with that problem. Because I'm an engineer again. I'm an engineer by upbringing. My favorite classes at school other than some of the stuff we've talked about was 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 things happened. So one is I paused. I'm like, okay, I'm working on this company. I'm kind of burning out. Part of why is because I thought about like, okay, even if all of my dreams come true and everything we hope for happens with this SAT prep company, then I'm like, then what? And I'm like, I'm like king of SAT prep, right? And there's nothing, I mean I think that's fine and people need help with these things but I'm like that's not what I want to do. I'm just picturing this kind of cardboard crown and I'm like, and that's only if everything goes well or that's like if all of our dreams come true. So I'm like I need to do something else. And so I ended up with these side projects and then found myself getting totally obsessed with first the poker bot but then even more so with Dropbox. And so sometimes it's hard, you know, like how do you deal with burnout? How do you know if you're doing the right thing? Like 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.

Yes. So Paul Graham is best known as one of the founders of Y Combinator. So they are, which is an incubator for startups. They were our first investors and they also invested in a lot of great companies including Airbnb, Stripe, a lot of them. And Paul was, before starting Y Combinator he had written, he was an entrepreneur himself. So he started a company called Viaweb back in the 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. And that's actually how I first heard about him. But then he started writing about startups and then ran this experiment that became Y Combinator. But it was actually called the Summer Founders Program. And I was digging through some old email about it because this was the precursor to Y Combinator. I applied with my SAT prep company to that and was rejected. But then managed to get into Y Combinator a couple years later. So I guess the first virtual meeting of applying to be funded didn't go well. The first in-person meeting was probably...

Well, we didn't really virtually meet. It was just sort of like it was like a college admissions thing. It's open application. Anybody who wants to submit an application can for the Summer Founders Program which is basically it was like the same thing as Y Combinator like you get a little bit of money and all come together, it was like sort of Y Combinator version one. But I applied and didn't get in and I was super disappointed. So that didn't go well and then but a couple years later I wanted to apply again with Dropbox. And this is skipping ahead a little bit but I had, so I had the idea for Dropbox. Started working on it and I wanted to do YC because a good friend of mine, or for many reasons but another friend of mine, this guy Adam Smith, no relation, who was one of my friends from college. He did YC in 2006 and had an awesome experience and I had like a front row seat to that and saw how much fun they were having and then their company was just in a much faster trajectory because of YC and I'm like oh my god I want something like that. But then I started thinking about applying for YC with Dropbox. And one of the good things about coming from college admissions is you sort of learn how these admissions processes work. And YC was not really that different. You have a lot of people applying for a few spots. And so in addition to getting the scores and the grades and everything, one of the things you can do is try to stand out and do something kind of unique. And so I'm like, all right, well maybe to help me get into YC, I'll try to put a video out about how Dropbox works. And Y Combinator also had their own, they had just started this new, this news site called Hacker News. Which is kind of like Reddit for startup news. And I'm like, what is, and I thought, I had a hunch. I'm like, what does Paul do all day? I think he probably does what most of us do, which is 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, something like that. It's like how do you do that when you have no money? So, and so there 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. And so, but I made a screencast which is like a three-minute demo of how Dropbox works because I wasn't ready to ship the code, but I wanted some feedback and I wanted to get into YC. And that video both got me into YC and it got me a co-founder. But I didn't know that at the time. 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.

That can't happen anymore because for a bunch of reasons, but I was pretty happy about that. And then I'm like, okay, this is so far the plan seems to be working. And I'm just like keep hitting refresh on my inbox. I'm like, I wonder if Paul has seen it. And then lo and behold, I get an email from Paul Graham saying like, hey, looks pretty cool. But you need a co-founder because they did, especially at the time, they didn't like single founders applying and I didn't have a co-founder yet. This was before I met Arash. So I was like, oh god. Because the only problem, I agreed with him. The only problem was the application deadline had already passed. I had already applied. And the interviews were in like two weeks. And so I needed a co-founder in two weeks, which is like saying like, hey, I know you're not dating anyone, but you need to get married by, right? And so 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 but I found another friend of, I actually managed to get a friend of mine interested out in San Francisco but he's like okay I'm interested I don't know but I want to know what PG thinks before I make a decision. So, I'm like, okay, great. And I'm like, it's a Tuesday. My flight, it's a Tuesday at like 1:00 p.m. My flight back to Boston leaves at like 10:00, 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 one. I get the Zipcar. I fly down 101. And like the plan was working pretty well. I got to YC. I went in the office. It was as expected. People were just chilling and there was some downtime. And so I go knock on, I go to Paul's office and sure enough he's in there. He's just chilling. I'm like, hey Paul, do you have a minute? I just wanted, you know, I just wanted to show you something I'm working on. And he's like, nope, I'm busy. And I'm like, okay, look, we both, I can almost see your screen. I know you're just like hitting, you're just like reading Hacker News right now. I'm actually busy. But it's like awkward. So, I step outside and I talk to Jessica, who was his partner in co-founding YC together and his wife. And I talked to Jessica. I'm like, hey, look, Jessica and I had met Jessica before. So, I'm like, Jessica, I'm really sorry to bother you guys. I just have a co-founder who was looking for some feedback from Paul to make his co-founder decision. You know, I got a flight back in like four hours. I swear I won't take more than 60 seconds of Paul's time. Do you think it's okay if I go in there? And she's like, oh, yeah, Drew, of course. Like, no problem. Like, Paul's not doing anything. Just like, he'll, 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. And so I'm like, okay, thanks Jessica. Thanks Paul. I'm like, ooh, like my friend that's, I'm like this is not going to be good. I'm like, this is a rough return to San Francisco. So needless to say, the co-founder situation did not work out.

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

I think he's coming around. Let me get back to you.