The Exchanges

Q I would love to start today with a little bit of an origin story. So what was the original unique insight you had with Dropbox? How did you get it? And how did it lead to the founding of the company in a succinct two to three minutes?

A Sure. Yeah. I mean, it was, uh, kind of as a user, I kept forgetting my thumb drive. I had started another company at the time doing online SAT prep of all things. Um, but I needed to work from multiple computers. And so I had everything, all of our company's crown jewels were on this little thumb drive that I kept losing or almost putting the washing machine. Um, all the things that used to happen. And, um, it culminated in this, I was taking this bus ride from Boston to New York to visit my friends, but I wanted to get some work done for, uh, my company. And I realized when I got on the bus, I had forgotten my thumb drive. Um, and, uh, you know, I, I, I wasn't like, oh, I hate my thumb drive. I was like, oh, I hate myself. God, I'm so disorganized. I need to, You know, be more on top of this. But as I thought about it, I'm like, man, I'm just so frustrated with this. This keeps happening. I never want to have this problem again. And I started writing some code, some Python code, uh, on that ride. Cause I didn't have anything else to do. And this was like before you had iPhones and wifi on buses and things like that, but I had no idea what it would turn into, but it was really just a personal frustration.

AI assessment note: “I realized when I got on the bus, I had forgotten my thumb drive.”

Q I want to talk about your leadership. You know, I think about high performance a lot in sport, but also in business and leadership. When I say high performance to you, how do you define it, and what does it mean to you?

A Yeah. So I'm kind of, um, I come from like the Andy Grove school and he has a great book, high output management. He was the former CEO of Intel, one of the founding team in Intel became the CEO, started as an engineer, um, learned on the business, learned the business side along the way, being inspiration for me. Um, and one of the tenants of his management philosophy is, uh, a manager's performance, uh, cannot be rated higher than the output of their organization. So I think you start with All right. Do you deliver results, right? You start with the outputs for whatever you're doing. And so in sports, that might be the stopwatch or the scoreboard. It's pretty hard to argue that you're like a great, you know, sprinter if the stopwatch doesn't agree with you or that you're a winning or that you're a great team if you're, if the scoreboard doesn't agree. So I think you start with the outputs and that's the most important thing that said, you know, there are plenty of cases where, um, Or one, one issue is you don't really, in, in most of these efforts, you don't actually control the outputs directly, right? You don't, when you're like, I want to win the football games now, you're like setting the score, right? You can only control the inputs. Um, so.

AI assessment note: “a manager's performance, uh, cannot be rated higher than the output of their organization”

Q Final question before we do a quick find. I have to admit it's another one from Doug. He asked, um, have you ever had the chance to sell the company? And if so, why didn't you?

A Yeah. Um, so we, we have different, um, different points, especially early on. I think any company that's doing well, you get a lot of overtures from different folks. You know, we had, we got kind of Kicked up the, uh, kicked up the food chain to, we had a meeting with Steve Jobs at Apple after a series of other meetings. Um, how did he go? It was wild, you know, it was, uh, he, you know, he came in, he sat down, he's like, you guys have built a great product. You know, like bucket list, like under the table. I'm like, Hey, check. Steve said we have a great product. It's awesome. Um, but I was also a little terrified because I talked to a lot of other founders and the Steve stories kind of fell into one of two buckets, like either super charming, wonderful, or like the opposite, like total asshole Steve. And, you know, we didn't know which we were going to get. And so he kind of launches into this pitch. He's like, you guys should really throw in with us. We're like a startup with unlimited resources, et cetera, et cetera. And I'm like, oh, this is going to be awkward, but I'm like, Steve, like, we really love Apple, really admire everything you've done. Um, but, you know, we're really enjoying building this company and, you know, uh, I think we have a long way to go, uh, to do that. Um, I'm sure you understand, but I thought he was gonna like start throwing stuff. And then he'…

AI assessment note: “we're really enjoying building this company and, you know, I think we have a long way to go”

Q You said there about kind of mindset changing. I often find my sense change often actually in quite a catalytic way, which is like a certain event causes it to change. Like when I, I'm an investor also, when I lost a company, my mindset changed quite significantly. If you look at back on your timeline, is there one or two catalytic moments which cause your mindset to change?

A Yeah. Yeah. Um, a couple come to mind. So one, one was my first experience with executive coaching, which I highly recommend. It started off kind of pretty, you know, standard issue coaching experience. You do a three 60 with your team. You sit down, you get a little presentation of, you know, it starts with like, all right, Drew, uh, have a seat here. Page one, here are your strengths. Uh, you're creative. You like new ideas. You like people and relationships. And I'm like, okay, I like this coaching thing so far. Keep going. Uh, you know, next page, it's always your development areas, not your weaknesses, but your development areas, uh, your conflict avoidance, you're a bit of a space cadet, and maybe one of your strengths is you're comfortable in chaos, but then you don't actually create structure for your team, which is frustrating for people. The kind of unlock there was, uh, when you paired the strengths and weaknesses, they're sort of both sides of the same coin. Like if you like new ideas, then you're bored by routine and not super disciplined about little details. If you love building relationships with people and creating positive vibes, you're conflict avoidant and avoid telling people the truth. Um, so I think the most important, so the, the catalyst was like really first, just awareness of these things instead of them just being kind of in your, you're like sort of…

AI assessment note: “a couple come to mind. So one, one was my first experience with executive coaching”

Q And I spent the day crying in a corner. So my question to you is, how did you personally handle the cycle which builds you up faster than anything, magazine covers, you name it, and tears you down quicker than anything now? What would you advise me and some of the founders that are going through that?

A Well, I don't, I think there's nothing anyone can say that will make it that much easier. So just recognizing there's no like bandaid. You're like, okay, now I'm better. I feel better. Like it sucks. Um, it's really embarrassing. You know, I, I, my first company, my bootstrap company, like it never really succeeded and then it died, but like, then Dropbox was like succeeding massively and then seemed to be dying massively. And I'm like, that is way worse than any of the others. Um, so first is recognizing that it sucks. Um, second, you know, I think you need to, um, as far as how to cope with a lot of the stress and kind of manage your psychology, I think depersonalizing it a little bit and being like, wait, this is not like me specific. This is just like part of the game versus how things work, like the press. You know, it's not personal. They just, they need something that's like the little engine that could, and then at some point they need to tear it down. Like this is how it always has been and always will be. It's not really about you. And then sort of seeing it and then depersonalizing it more. I mentioned before that, like, I want to play the game really well, but I think that the game part is intentional. This is not like Life and death. Like if you sort of internalize, I think it's important to internalize the responsibility you have on your shoulders for people's liv…

AI assessment note: “depersonalizing it a little bit and being like, wait, this is not like me specific”

Q You said there about kind of mindset changing. I often find my sense change often actually in quite a catalytic way, which is like a certain event causes it to change. Like when I, I'm an investor also, when I lost a company, my mindset changed quite significantly. If you look at back on your timeline, is there one or two catalytic moments which cause your mindset to change?

A Yeah. Yeah. Um, a couple come to mind. So one, one was my first experience with executive coaching, which I highly recommend. It started off kind of pretty, you know, standard issue coaching experience. You do a three 60 with your team. You sit down, you get a little presentation of, you know, it starts with like, all right, Drew, uh, have a seat here. Page one, here are your strengths. Uh, you're creative. You like new ideas. You like people and relationships. And I'm like, okay, I like this coaching thing so far. Keep going. Uh, you know, next page, it's always your development areas, not your weaknesses, but your development areas, uh, your conflict avoidance, you're a bit of a space cadet, and maybe one of your strengths is you're comfortable in chaos, but then you don't actually create structure for your team, which is frustrating for people. The kind of unlock there was, uh, when you paired the strengths and weaknesses, they're sort of both sides of the same coin. Like if you like new ideas, then you're bored by routine and not super disciplined about little details. If you love building relationships with people and creating positive vibes, you're conflict avoidant and avoid telling people the truth. Um, so I think the most important, so the, the catalyst was like really first, just awareness of these things instead of them just being kind of in your, you're like sort of…

AI assessment note: “a couple come to mind. So one, one was my first experience with executive coaching”

Q I love that. Now, speaking of kind of stories that we have to discuss, I spoke to, kindly thanks to your suggestion. Adam, before the show, and he told me that the YC story is the ultimate story of hustle, and that I had to discuss it. So, starting there, what was the YC story that we have to hear?

A Sure. Well, Adam Smith is one of my best friends and we went to college together and he did Y Combinator and him, and he moved out to California. He got VC funding. Um, and so all of that, his experience was a big inspiration, uh, to me as, as he was going through all that. Um, and I, yeah, so I personally had a very winding road into Y Combinator myself. So I actually applied in 2005 to the first batch with that SAT prep company, Accolade, uh, and was rejected. Um, And then I was still working on it when I had the idea for Dropbox. Um, and, um, I was getting a little burned out from the SAT prep thing. I'm like, I, I don't know how many more equations, you know, Equations about parallel lines or the train leaving Memphis and, you know, just like all the things with SAT prep, you can, as passionate about it as you can be, but it kind of getting a little burned out. I recognize now. Um, uh, and I was like, Hey, this might be a good fit for Y Combinator. Um, so I wanted to apply that said, one thing that was useful from my whole, uh, test prep background was really understanding college admissions, uh, Actually pretty similar, a lot of similarities with something like Y Combinator. We have a lot of people applying for a few slots. So anything you can do to get an edge or a hook would be helpful. So to me, um, the dean of admissions here was Paul Graham, uh, the, uh, one of the fo…

AI assessment note: “I personally had a very winding road into Y Combinator myself.”

Q I want to talk about your leadership. You know, I think about high performance a lot in sport, but also in business and leadership. When I say high performance to you, how do you define it, and what does it mean to you?

A Yeah. So I'm kind of, um, I come from like the Andy Grove school and he has a great book, high output management. He was the former CEO of Intel, one of the founding team in Intel became the CEO, started as an engineer, um, learned on the business, learned the business side along the way, being inspiration for me. Um, and one of the tenants of his management philosophy is, uh, a manager's performance, uh, cannot be rated higher than the output of their organization. So I think you start with All right. Do you deliver results, right? You start with the outputs for whatever you're doing. And so in sports, that might be the stopwatch or the scoreboard. It's pretty hard to argue that you're like a great, you know, sprinter if the stopwatch doesn't agree with you or that you're a winning or that you're a great team if you're, if the scoreboard doesn't agree. So I think you start with the outputs and that's the most important thing that said, you know, there are plenty of cases where, um, Or one, one issue is you don't really, in, in most of these efforts, you don't actually control the outputs directly, right? You don't, when you're like, I want to win the football games now, you're like setting the score, right? You can only control the inputs. Um, so.

AI assessment note: “a manager's performance, uh, cannot be rated higher than the output of their organization”

Q Speaking of difficult conversations to have, I often find that the biggest lessons are learned from difficult times. Um, I, I learned probably one of my biggest investing lessons from losing an investment. When you think back over the journey, what is the most difficult lesson that you learned that you're also super pleased to have learned because of the value that you gained from it?

A Yeah. Well, I think one of the toughest moments for me was going through the period of hyper growth and then having that And then kind of hitting the peak. And then when the, then things start going the other direction. Um, so for us, we had maybe the seven year period from 2007 to 20 14, where we were just like living the dot com dream, you know, Numbers, money, everything going up, billion dollar valuations, all that magazine covers. And then it was also clear that like we were inviting competition from like the best and most capitalized companies in the world and that Microsoft and Google and Apple and literally everyone was coming after us, um, cloning our products, bundling them with the operating system or platform, giving everything away for free. And this kind of came to a head when, you know, on the one hand we, we had, we were really spreading our wings as a company and expanding these different areas. When we launched this new, uh, or this, this photo sharing app called carousel, we bought this company called mailbox, which was like the first one of the first great kind of mobile email clients. And so like, uh, this feeling of like flourishing and going out, but at the same time, it was clear that pretty much everything we discovered pretty quickly that everything we do is going to be copied very quickly. And that fighting against these mega cap companies is like, yo…

AI assessment note: “moving into the big leagues means you get harder and harder opponents”

Q I ask you on one, you know, the, we have schedules and then we just go off them, but that's a very, um, loose, like, relationship pre-deciding to found a company and spend your life together with someone bluntly. Given that it's working so well, how do you advise founders on founder selection given so many people say a lot, given your experience, how would you advise founders on cheating?

A Well, I don't. Yeah. I mean, our equivalent was like getting married on the second date, which, um, if you can avoid it, the good news, we got lucky. So it worked for us, but I think it's much better to, uh, or I think, you know, on average is probably better to a lot of the founder co-founder stories start with like, Oh, we played tee ball together as little kids and have known each other since forever. Um, I think if you have that, that, uh, Is a bit of a safer bet. Um, I did have friends like that, but they were just busy and doing other things. So, um, but I think that's ID. It can still, you know, there's a lot of different co-founder origin stories. I think what the good ones have in common is like any other serious relationship, um, where I think you need to have a sense of mutual trust and respect. Um, meaning trust as in basic things like integrity, um, and having a good sense of that, but like, just, are you motivated by the same things? Are you trying to accomplish the same things? You have the same picture. Of what you want to do with the company and then respect. I mean, you, one thing about any co-founder relationship is you need to have complementarity and overlap on some, on, on some things. So like for the important kind of existential questions, the company, like, what do we want to, what do we want to achieve? How do we want to achieve it? What kind of cultur…

AI assessment note: “what the good ones have in common is... a sense of mutual trust and respect”

Q I ask you on one, you know, the, we have schedules and then we just go off them, but that's a very, um, loose, like, relationship pre-deciding to found a company and spend your life together with someone bluntly. Given that it's working so well, how do you advise founders on founder selection given so many people say a lot, given your experience, how would you advise founders on cheating?

A Well, I don't. Yeah. I mean, our equivalent was like getting married on the second date, which, um, if you can avoid it, the good news, we got lucky. So it worked for us, but I think it's much better to, uh, or I think, you know, on average is probably better to a lot of the founder co-founder stories start with like, Oh, we played tee ball together as little kids and have known each other since forever. Um, I think if you have that, that, uh, Is a bit of a safer bet. Um, I did have friends like that, but they were just busy and doing other things. So, um, but I think that's ID. It can still, you know, there's a lot of different co-founder origin stories. I think what the good ones have in common is like any other serious relationship, um, where I think you need to have a sense of mutual trust and respect. Um, meaning trust as in basic things like integrity, um, and having a good sense of that, but like, just, are you motivated by the same things? Are you trying to accomplish the same things? You have the same picture. Of what you want to do with the company and then respect. I mean, you, one thing about any co-founder relationship is you need to have complementarity and overlap on some, on, on some things. So like for the important kind of existential questions, the company, like, what do we want to, what do we want to achieve? How do we want to achieve it? What kind of cultur…

AI assessment note: “what the good ones have in common is like any other serious relationship”

Q Can I ask, I'm incredibly conflict avoidant too. What have been some things that have worked for you in trying to mitigate that and trying to combat it?

A It's tough. I think first is, I think, well, recognizing it comes from a good place, you know, and often you're trying not to hurt people's feelings or there's, or, you know, there are other kind of positive motivations for it. But I think over time, when you withhold feedback from people, you realize that the outcome, or you're actually not helping them. Um, and because they keep making the same mistakes over and over again, Or, or keep having the same patterns and, and they don't know about it. And so they don't do anything about it. And then everybody's frustrated, recognizing that sometimes, and then when you think about your own experience, like you appreciate it when people tell you stuff that you like, you didn't know, or like you have a thing in your teeth, you know? And so there's sort of this mismatch between what you want to do and what you want others to do for you. Um, and I think just getting first, like recognizing this as a pattern, it's normal. Um, but then Uh, also, I, I think starting just to experiment with just being more direct and assertive and real and then realizing that, um, you know, usually the world doesn't come crashing down or the person isn't as, uh, kind of offended by all this as, as you think. And then recognizing also, I think there's sort of a superhero complex that can kind of be lurking under the surface here. So often, you know, I would s…

AI assessment note: “starting just to experiment with just being more direct and assertive and real”

Q Can I ask, I'm incredibly conflict avoidant too. What have been some things that have worked for you in trying to mitigate that and trying to combat it?

A It's tough. I think first is, I think, well, recognizing it comes from a good place, you know, and often you're trying not to hurt people's feelings or there's, or, you know, there are other kind of positive motivations for it. But I think over time, when you withhold feedback from people, you realize that the outcome, or you're actually not helping them. Um, and because they keep making the same mistakes over and over again, Or, or keep having the same patterns and, and they don't know about it. And so they don't do anything about it. And then everybody's frustrated, recognizing that sometimes, and then when you think about your own experience, like you appreciate it when people tell you stuff that you like, you didn't know, or like you have a thing in your teeth, you know? And so there's sort of this mismatch between what you want to do and what you want others to do for you. Um, and I think just getting first, like recognizing this as a pattern, it's normal. Um, but then Uh, also, I, I think starting just to experiment with just being more direct and assertive and real and then realizing that, um, you know, usually the world doesn't come crashing down or the person isn't as, uh, kind of offended by all this as, as you think. And then recognizing also, I think there's sort of a superhero complex that can kind of be lurking under the surface here. So often, you know, I would s…

AI assessment note: “starting just to experiment with just being more direct and assertive and real”

Q Final one. Dropbox in five years. Where will we be Drew?

A Well, I think, well, where we're headed is shifting from Dropbox from syncing your files to organizing all your cloud content and stuff to organizing your whole working life. And so, um, we're all using a ton of different tools is that we have very fragmented experience, you know, under the zoom window here is just total mayhem, a hundred tabs open. We think Dropbox can do a lot to help you with those kinds of problems. Um, Um, and, uh, and then, so I'd say both with, in a world where we're now working out of screens instead of offices, there's a lot of room for that, that digital environment we're all in is a lot, is really important. There's a lot of room for improvement. Um, and then also the renaissance we're seeing in machine learning, where we're all kind of getting this silicon brain in addition to our human brains. And where I think we'll be able to, we're finding that we're going to be able to split up the work, uh, or offload a lot of our busy work to machines. Um, so I think the combination of pulling everything together And building a generation of smarter tools and a smarter system. Those are things that I'm really focused on with Dropbox.

AI assessment note: “shifting from Dropbox from syncing your files to organizing all your cloud content”

Q Speaking of difficult conversations to have, I often find that the biggest lessons are learned from difficult times. Um, I, I learned probably one of my biggest investing lessons from losing an investment. When you think back over the journey, what is the most difficult lesson that you learned that you're also super pleased to have learned because of the value that you gained from it?

A Yeah. Well, I think one of the toughest moments for me was going through the period of hyper growth and then having that And then kind of hitting the peak. And then when the, then things start going the other direction. Um, so for us, we had maybe the seven year period from 2007 to 20 14, where we were just like living the dot com dream, you know, Numbers, money, everything going up, billion dollar valuations, all that magazine covers. And then it was also clear that like we were inviting competition from like the best and most capitalized companies in the world and that Microsoft and Google and Apple and literally everyone was coming after us, um, cloning our products, bundling them with the operating system or platform, giving everything away for free. And this kind of came to a head when, you know, on the one hand we, we had, we were really spreading our wings as a company and expanding these different areas. When we launched this new, uh, or this, this photo sharing app called carousel, we bought this company called mailbox, which was like the first one of the first great kind of mobile email clients. And so like, uh, this feeling of like flourishing and going out, but at the same time, it was clear that pretty much everything we discovered pretty quickly that everything we do is going to be copied very quickly. And that fighting against these mega cap companies is like, yo…

AI assessment note: “discovered pretty quickly that everything we do is going to be copied very quickly”

Q You said about the responsibilities there, especially with teams. I spoke to Sujay before the show, and he said in particular that your ability to build the most incredibly talented teams was something that stood out to him. He asked what were some of your biggest lessons on talent acquisition, and also what are some of the biggest mistakes he made on hiring?

A Sure. Well, I think the first was, um, the first thing on talent is just really caring about it, which sounds kind of obvious, but we, we had a great, uh, we had great early investor and advisor, uh, Hadi Partovi, who was also an early investor in, um, in Facebook and started a bunch of companies really, um, experienced and successful and generous with his time with us. So Hadi told us, he's like, Well, I asked, we were asking really, Hey, how do you give us advice on how do we build a great company? And he's like, yeah, I asked my mentors the same question. And he's like, my mentor told me, you know, there are 10 things that you need to do as an entrepreneur. Hire the best people, hire the best people, hire those people. And I'm like, okay, Adi. Yep. Got it. But just like drilling into our heads, the importance of recruiting, especially early on. Really? And I, so, so we internalize and then there's like really caring about how do you recruit the best people? How do you build all stages of how do you sell the, how do you get candidates excited, source them, really caring about the craft of all of that is something that Arash and I became pretty obsessed with, um, in pretty direct response to Hadi's feedback. Um, and then recognizing that, you know, your, your company is, um, Uh, whatever your company is or startup is right now is sort of the seed crystal for the company it wil…

AI assessment note: “the first thing on talent is just really caring about it”

Q You mentioned Sequoia there. I told you I did my work before the show. I, I spoke to Doug before the show. Um, and he asked two questions. He said, ask him about the story of getting Sequoia invested and what you did to convince us. Um, so I'm going to start on that. What did you do to convince Sequoia?

A Well, we had a very, as I said, our whole road into Y Combinator was kind of strange. And then the, we, we had a pretty unusual path after that too. So after Y Combinator culminates in demo day, where you basically, uh, you know, they were fill up a room full of investors and a few companies, uh, obviously it's a lot bigger now, uh, then there were maybe 10 companies in our batch. Now there's like a thousand or something. But one of the, the first person who came, we did our demo at Demo Day, uh, one of the people who came running up to us was a guy named Pejman, who's like, actually came up running, came running up to her, I was giving the presentation, but he ran up to Arash and started speaking Farsi to him, and I'm like, what is going on? And Pejman's like, oh, you guys need to come down, like, because we were, we were living in Boston, but we were just in Mountain View visiting for a Demo day, and he's gotta come visit, and we're like, I don't know, we're still, we're kind of about, we've almost kind of raised our first round, but sure, he's very persuasive, and he's like, okay, come to our office, here's my business card, the other states, we get a schedule, we come have some tea, come have some tea. Well, that's the thing, so yeah, we get down there, and I'm like, and we're like, this is, we were renting another zip car, getting down there on University Ave in Palo Alto,…

AI assessment note: “we had a pretty unusual path after that too.”