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Podcast Summary: The Logan Bartlett Show - EP 119: Drew Houston (CEO, Dropbox): Reflections on the 17+ Year Battle Against Big Tech
Introduction In this episode, Logan Bartlett interviews Drew Houston, the co-founder and CEO of Dropbox, who reflects on his 17-year journey at the helm of the company. Their conversation delves into leadership lessons, challenges of competing with big tech, fundraising experiences, and the transformative potential of AI in the workplace.
Key Topics Discussed
- AI Opportunities for Dropbox
- Democratization of AI: The impact of open-source AI and its accessibility for product development.
- Personal Journey: Drew discusses his early experiences with AI and machine learning.
- Future of AI: Emphasizes the transformative potential of AI in collaborative work and productivity.
- Dropbox's AI Principles
- Transparency and Trust: Importance of establishing clear AI usage principles to assure customers about privacy and safety.
- Customer Concerns: Acknowledges the anxieties customers have about data privacy in AI applications.
- Product Development and Innovation
- Introduction of Dropbox Dash: A tool designed for universal search addressing the common frustrations of knowledge workers.
- AI Enhancements: Discusses the role of AI in improving search capabilities and personal productivity.
- Leadership and Company Culture
- Memo-First Culture: Adoption of narrative-based meetings to improve communication and decision-making.
- Lessons from Management: Drew reflects on the evolution of his leadership style from a technical founder to a CEO and the continuous learning required in this role.
- Challenges and Competitive Landscape
- Facing Big Tech: Insights on navigating competition from larger firms like Google, Microsoft, and Apple.
- Strategic Shifts: The decision to pivot Dropbox's focus from general storage to collaboration tools following intense market competition.
- Growth and Scaling
- Viral Growth Strategy: Explains the early tactics that led to Dropbox's rapid user acquisition, including their referral program.
- Reflections on Scaling: Challenges faced in scaling operations and maintaining company culture during rapid growth phases.
- Personal Reflections and Future Vision
- Long-term Perspective: Drew shares his personal motivations and how they have evolved over the years.
- Vision for the Future: Excitement about the role of AI in creating a more productive and less distracted work environment.
Key Takeaways
- Leadership is Learned: Becoming an effective CEO takes time, patience, and a commitment to ongoing learning.
- AI as a Transformative Force: The integration of AI into workflows can elevate productivity and redefine how teams operate.
- Trust and Transparency: Establishing clear principles around AI use is critical to maintaining customer trust.
- Focus on Core Strengths: Companies must identify and double down on their core competencies in response to competitive pressures.
Conclusion Drew Houston's insights offer valuable lessons for entrepreneurs, emphasizing the importance of adaptability, trust-building, and continuous learning. As Dropbox evolves, the integration of AI presents both challenges and opportunities that could redefine the future of work.
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Additional Resources
- Books Mentioned:
- "High Output Management" by Andy Grove
- "The Effective Executive" by Peter Drucker
- "Only the Paranoid Survive" by Andrew Grove
- "Working Backwards" (Amazon principles)
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This summary captures the essence of the podcast episode while outlining key discussions and takeaways that can benefit listeners interested in entrepreneurship, leadership, and technology.
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Transcript
Automatic transcript. May contain errors.0:28Welcome to the Logan Bartlett Show. when you try to compete with big tech, as well as his view on the future of artificial intelligence and the opportunity that it presents for Dropbox going forward. Thanks for coming on. We're glad we were able to make this work. It's great to be here. So one of the topics is yours. I don't know your perspective on this is artificial intelligence these days. And I think you sit in an interesting purview, both as the CEO founder of Dropbox, but then also you fairly recently joined Facebook's board. Yep, about five years ago, a little under five years ago. Okay, so not that recent.
0:59And you've probably seen, I mean, this has been an interesting, was it Facebook at the time? It was Facebook at the time, and then they changed the name a couple years in. So you've seen a lot of the AI investment that that business has gone through. I'm curious, how has that seat, that purview, informed your perspective on the AI opportunity for Dropbox? Well, it's been great to watch. and I won't speak for meta itself, but certainly seeing the power of open source and the impact it's had on democratizing AI has been really powerful. Whenever there's a new era of computing, there's a question of, is it going to be open?
1:40Is it going to be closed? And so open source has been super powerful, clearly in terms of making AI more accessible and in terms of both being able to use it, build products with it, research. which I think on balance, it helps with things like safety because you have a lot more people working on that problem versus a situation where a couple companies are the gatekeepers to everything. I think there was definitely an alternate future where we'd all be kind of like paying rent to a couple big companies. But instead, we've seen the price performance of these AI models plummet, you know, like drop 10 or 100 times better price performance every year.
2:19and that's for a product developer like me or like Dropbox. That means like what we can build is a lot more exciting and more affordable and things that would have been kind of priced out as being too expensive to do that much inference at our scale suddenly become viable. So it's been awesome to have that vantage point too. Did you have a moment in time that you can remember that was like, okay, this is going to, I clearly need to focus on this for Dropbox business going forward? For me personally, it started to heat up. I started playing with more classical machine learning mid-2010s. I thought about going to grad school, did my undergrad in computer science, but never did the grad level courses.
3:05So I tried to self-teach classical machine learning to see what that was about. And then certainly as deep learning, large language models came on the scene, then there was like that thunderclap you know iphone launch moment of chat gpt and when you when they uh had these instruction tuned models in like gpt3 then it was a little embarrassing i was like on my honeymoon like coding and playing with these things um where i was like oh my god it's happening like all the stuff i wanted to build and you know back when i first started studying this stuff is like i hit all these roadblocks because like computers basically couldn't understand text.
3:40But then the large language model is like, not only does it understand text, it can write text, it can write you JavaScript, and then write a sonnet about the JavaScript. I'm like, wow, a lot just happened in like one, one minute. It would seem like one very unusual person that could do all of those things. Yeah, which is powerful to the AI side. It was a big wake up call. Is there something that you look at now, both from your seat as CEO of Dropbox, as well as, you know, getting this purview into how Meta is making these investments that you sort of think is an inevitability that maybe we're not thinking about if you pick a point, I don't know, 10 years in the future that sort of feels to you like innately, obviously, this is gonna, this is gonna happen, but might not be, you know?
4:20Yeah. I mean, the thing I'm most excited about is we sort of have this, we have our human intelligence or our human brain, and then there's this new silicon intelligence or silicon brain. And just as you saw in computing, we're adding a GPU to the CPU suddenly made all these new things possible like ai um in our working lives it's we're gonna have this really kind of wild partnership with our like as we plug in the silicon piece of our brain um and so i think a lot of work will be reimagined um where we'll be able to offload a lot of our busy work and be freed up um for more like creative or relational tasks you know i don't think anybody can really predict exactly what the precise route will be through the fog here.
5:07But I think we'll be able to have, or I think we're opening the door to being, you know, where anybody can be a 10X person and people that really figure out how to master these tools can be 100X people. So I think it'll be certainly the most transformative change in our lifetime. Have you played with any of the physical devices, like the pendants or any of those things? Not a lot. I mean, I'm very excited about voice or the ability to have sort of like an infinite memory and all these different contexts as you're using your computer or your phone, for sure. It needs to become more socially acceptable.
5:40I think a lot of those things are very, it's very cool, but there's some social element of adoption that exists in the real world. Yeah. And I mean, even there's some basic like legal restrictions. You're not allowed to just go around like taping everybody. Single party consent and all that stuff. Dropbox has some AI principles. We do. And what are those? So we established pretty basic principles around transparency, around how we use AI, things like privacy, safety, kind of all the setting forth all the things that Dropbox will and won't do. Because, I mean, for a number of reasons, but one is, you know, customers, and I'd say all of us are really excited about the good parts of AI, pretty concerned about the things that can go wrong.
6:29And then when you intersect that with your stuff or your most important information, your personal information, your company's information, you care a lot about making sure that you can trust your counterparties or the services that you're using. And we had some experiences around this with Dropbox 1.0 because people for the first time, or a lot of people for the first time, were putting their most important information into the cloud. And this happens a lot, you know, whether putting your money in a bank instead of under your mattress or putting your credit card over the Internet or putting your files in the cloud.
7:01People start out with a lot of same apprehension. That's very justifiable. And so this was a way for us to just be in front of that, say, here's how we'll use your data. Here's how we won't. And reinforce one of Dropbox's big advantages, which is that our incentives are much more fundamentally aligned with our customers from a trust perspective. because I think a lot of people worry about, when you just think about how these models are trained, it's like, oh man, is this service going to take all my stuff and sort of grind it into little pellets to either sell me ads or to train their next foundation model or have other some kind of undisclosed use of my information?
7:37We wanted to draw a bright line and say, no, we're not. I think everybody's looking for providers they can trust. And so setting these principles affirmatively was a step we took pretty early on. And a lot of companies have also published similar principles. And so for folks that don't know, what AI products have you released to date? And what are some of the things you're excited about for the potential going forward? Yeah, the most notable one is we have a new product called Dropbox Dash, which is really centered around universal search. So the first basic problem we're solving is, you know, I know that thing exists, can't find it.
8:16and this question of like why do we live in a world where it's easier to search all of human knowledge with a google search and then when i go to search for my company stuff or search my company stuff search my own information you know i got 10 search boxes um and it's much worse experience and then weirdly despite all this technological progress this problem is like much worse today than it was 20 years ago um 20 years ago if you want to find your stuff you just like search your hard drive right or your email or so maybe one or two search boxes but now we've had this, it's kind of gone wild. So dash is really about fixing that, giving you one search box that can search everything.
8:50So it'll search your Google docs, your Slack, your email, your files, but really anything. You don't even need files in Dropbox. So this is a complete, it can be a completely standalone thing or integrate with your Dropbox. But we see that as like a very fundamental challenge that, that a lot of knowledge workers have. And especially as we've moved into these like distributed ways of working, like where's the information I need to do my job? and all the paper cuts that come along with that. By the way, how is that powered or enhanced by AI today? Enterprise search is a market that's been around for a long time, and it sounds like this is both consumer and B2B elements of it.
9:30We're focused on work use cases, yeah. So on the one hand, enterprise search has been around for a long time. On the other hand, sort of similar to cloud storage, like when we started. There were a lot of other things that sort of claimed to do it, But, you know, in our view, none of them had really done it right. And I think there's a similar dynamic that we've seen with how enterprise search has evolved, where, yeah, it exists, but no one really, when you ask the average person, like, do you use any of these enterprise search products? They're like, no. And, you know, have you used them? Yeah, it didn't really work very well.
10:03And so certainly the genre of AI allows you to not just do search, but really get answers. Yeah. And so Dash is also, we also view Dash as for a lot of the questions that ChatGPT can answer because it's not connected to your stuff. So if you ask, you know, if you or I ask ChatGPT a question, we'll largely get the same answer. But then if I want to ask, like, when does my lease expire? When does, you know, where's the slide from last year's product launch? Things like that. You need a product like Dash, which is connected to all your stuff and is grounded in all of your content. And so is the search opportunity then, and forgive me if this is a little nerdy, but more enabled in the natural language of how you can ask and then how you can, I guess, is there anything on the back end that's more intelligently done through large language models or whatever that actually surface this stuff up?
10:52absolutely so with search um there's a couple aspects i'd say when you sort of like double click on this specific problem there's uh people often have like retrieval use cases where it's like i know there's a thing or i'm looking for a specific asset and i actually just want the thing i actually don't want to have a question i want answered answered or i want to answer to a question like help i'm really at the end of the day looking for um okay what is the dat what's dash's roadmap or when's the release date or what are the key features, things like that. So it's a question. And the blue links kind of format is actually pretty good for retrieval.
11:28You just want to get the thing quickly. But then when you're discovering things or you don't know the answer, don't know where it might be, then a natural language fits in a lot better. And then there are also some of the underpinning technologies of large language models. These embeddings are a lot of semantic search, general search, fuzzy search, vector search, a lot of names for it, same thing. But basically, one of the unlocks was you can now search without having to match the exact keyword. So if you say like, what's the 2025 strategy or the 2025 plan, vector search can help turn up the right results for both of those.
12:05The things within the proximity that are close to it, rather, it could be, you could say 2025 plan, and if it was only language-based, it might show nothing if it was actually called whatever company estimates through 2030 that's right but it can get directionally there yeah and you know when you implement these things properly these can also be learning systems where they're always they're always getting smarter based on how you're it's becoming personalized to you as you use the service and then just smarter overall as the world is using the surface i i guess at a personal level are there things you're using ai for to make yourself more productive or regular behaviors that you've kind of adjusted Yeah, lots.
12:45I mean, you know, my first love is the engineering. And I grew up as a little kid coding. And so when the large language model came along, you know, around the chat GPT timeframe, I was suddenly like coding like an 18 year old again. And I'd say even before that, when I was learning classical machine learning or the kind of the pre deep learning techniques, there was lots of stuff that I wanted to automate. And even in my career, I started out as an engineer. I knew I wanted to be a startup founder. Wasn't actually sure I wanted to be a CEO, sort of backed into it. But as I really inhabited that role and the company was really scaling, I was like, man, there's a lot of tedious stuff that managers or executives do.
13:29So, yeah, I would have all these little tools to audit my calendar or figure out which of these emails needs a response. Actually, the motivation for Dash, from my perspective, I was like, I can't find my stuff. I need to, we need a better, I need a better way of managing this personally. I mean, forget a product. And then I wrote it and I was like, oh, and there's these embedding based or, you know, these vector search is a new thing. And I built this little prototype of a personal search engine. And I'm like, oh my God, it works. It's super scalable. It's super fast. Everybody's gonna be using something like this in a few years.
14:02This is maybe 2018, 2019. And I'm like, we should be all over this. So actually this is a lot of, I still write many thousands of lines of code a year. And that's like one of the key ways that I really get more of a tactile feel for like, here's what the technology is. Here's what it can do. Here's what it can't. And this stuff's fully baked. This stuff isn't. And yeah, I mean, I think it wasn't just my prototyping that led us to Dash. But that's really what caused me to have a lot of conviction pretty early and put a lot of chips on the table. Removing AI from the equation. Is there anything you've done from a productivity, either calendar tracking or email triage, or just anything you would recommend that people that are busy and managing different constituents and all that, anything you've done that you reflect on even outside of AI?
14:51Yeah, there's a lot of good stuff. And I'd say the best stuff is really timeless.
14:57And often the principles are pretty straightforward to describe. and the ones I would lean on are some of my favorite books are, um, high open management by Andy Grove. I guess one of the best books on management ever written. Um, another is the effective executive by Peter Drucker. Um, I could give a lot more, but, but just on the sort of productivity and effectiveness, uh, angle, I think those two probably get you 95 % of what you need to know from a theory perspective, but what's really hard about it is applying it, right? because it's sort of easy to read the book and then, you know, it's probably a super disappointing fraction of people actually apply the lessons.
15:36Um, and this is kind of this constant fight. So, um, a lot of my use of AI was really to automate some of these things. So for example, um, one thing that every, every busy person struggles with, like, is how am I using my time? And, uh, this first chapter after the introduction of effective executive, the title is know thy time. so what you do is you basically do a time audit and he's like okay here's um here's all the stuff in my calendar and i'm going to categorize it put in these buckets and and then you line it up to your priorities and so um you know i read the book a long time ago but 15 years ago i probably did my first time audit with my admin at the time and i was like oh i probably spend most of my time on recruiting uh and on products i don't know and then after the audit came back we tallied it up when we're like, actually, I spend my time on just about everything except for recruiting and product.
16:28So it sort of highlights this. It's one of these areas where it's not just that we don't we it's actually worse than not knowing where your time goes, you actually, where it actually goes, and where you think it goes are often like wildly disconnected. And that's like one of the first findings in the book is like, people are usually shocked by a time audit. And so, you know, it's something you have to do periodically, but it's a really manual process. And so it's something that lends itself well to automation. But yeah, all kinds of things like that. How am I using my time? Am I focusing? How am I keeping on top of my communication, personal search?
17:04Yeah, there's a lot of little code repositories in my little bag of tricks. I've heard you've moved to a memo first culture internally. I guess, what was the shift to doing that? Was that something you guys did in the early days? Yeah, it was something we did in the early days. But I would say it was really reinforced after COVID, and particularly after we shifted to being about 90 % remote and really kind of rethinking our working model of being a distributed company and sort of navigating the new world. So I think it became much more important then. And the origin or what really emphasize it is, so Jeff Bezos said of all the decisions he made when scaling Amazon, like the single best decision was actually had nothing to do with like his products or his markets or any of the other things where they've been successful.
18:01That's what I would have thought. He would have said something about that. But he's like, no, the best decision I ever made was to ban PowerPoint and the company and switch to this narrative based culture. For like a bunch of reasons. I mean, one is, or the reason why it was, is, is helpful is because like, we've all been in those, those meetings where someone's presenting, you've already read the slide, but you have to wait for the person's, you know, verbally to catch up. Or, you know, someone interrupts and asks a question, but the question's answered a couple slides later. And in one way or another, the presentation format kind of limits how many people you can have in a room to have an effective conversation.
18:42It's the, how compelled you are by the presentation is less about the merits of their arguments and more about their skill in presenting and thinking on their feet. So there's a bit of a distortion or bias that comes in that way. And then conversely, narratives are, they work really well because they, they have a much higher bit rate. So most people can read a lot faster than they can hear. and then when you not just write the narrative but spend the first you know 10 20 minutes of a meeting reading it which is part of amazon's practice something that we also do it's like then everybody has instead of like some vague like very vague and disjoint sets of context suddenly everybody has the same kind of high def 4k view of like what is like what are we talking about what is the plan um and you know everybody has that kind of fact base and it's super and it's super efficient to download that to, you know, you can have up to like 15 or 20 people in a room and have it still be efficient.
19:38I mean, the challenge with it is that there's a couple of issues. One is, um, it's very time consuming for the writer. Um, but it, or it's a trade-off. It's very hard for the writer, easier for the reader, but that's generally a good trade-off, especially in a bigger company, because there's a lot more readers and writers and often when you're communicating something, it's a lot more efficient to just give people the source of truth rather than verbally sort of game of telephone, broadcasting it over and over again. And then it can also become sort of a proxying that can happen where people sort of forget that the point of the narrative is to help get the work done.
20:12The point is not to write the narrative itself. So if you have all these, and I think you've seen this with some of what Amazon's reported recently, like, yeah, people are having the meeting, the pre-meeting before the meeting, and there's a lot of bureaucracy around the document, then you can lose the plot that way. Once the people have done the readout, then is it open Q &A for people to ask? Or is there generally, do you follow the points through for discussion at each point along the way? Because that's one of the things I've seen is you read it and then it's like any questions. And then it ends up being a little too open-ended.
20:45Well, I think there's different ways to do it. We certainly start by doing the pre-read. And then while we're doing the pre-read, I mean, we do it in Dropbox Paper, which is sort of our document tool. Um, where, but you can do this in Google docs or notion or anywhere else you could just, you, people leave comments in line. Um, and so, um, you both want sort of the fine grain feedback on like, okay, this specific little thing, but then you also want people to zoom out and be like, Oh, what's your overall reaction to this? And, um, and we've even had things where like, you have a little form where at the end of the pre-read you put your overall reactions and like a rating or things like that, which some other companies have done.
21:25so i think all those things can work but i think the biggest win is that you know you can get uh that 10 or 20 minutes um you can get a much more much higher fidelity um download to everybody in the room than you could get in an hour of just talking about it interrupting each other and then as far as the how they're you know to start at a high level or low level do you you know i think amazon does care a lot about they're like they ask everybody in the room to go around and give their reactions and Jeff goes last. I think something, things like that can be helpful to not bias people. Um, so I think the, but I think there's like multiple ways to do the review.
22:04I think that just the key thing is like, uh, is sort of doing your meetings through, through memos or narratives versus just conversation or presentations. As you reflect 17 years into the journey now, I guess it's still not at the point of more time with Dropbox than not. But, you know, at some point that'll cross in the next couple of years, right? I'm curious if you could go back and tell Drew from 2007 or 2010 something about, I don't know, leading a business or growing. Or is there something you reflect on and you wish you could impart to someone going through this journey that you've now been on?
22:43Totally. I think the first thing would be something like, it's a journey and just like, hold on. And then more specifically, becoming a CEO or becoming a leader is something that is more learned than innate. because I'd had sort of a picture in my head of like, oh, CEOs are like this, or they come out of the womb in an Armani suit with perfect hair or something. And I was like an engineer and I hadn't really ever been a business person. All I could see is like, well, what those CEOs look like and the things they know, I don't know a lot of those things. I don't seem to have that skill set. So as a first-time founder, technical founder, I was like probably like a lot of others, like insecure about, am I going to be able to figure this out?
23:28Because always, the more I know, the more I realize I don't know. So it was intimidating. So I think the advice would be, you know, just understanding that's part of the, it's part of the game, all the best, you know, a lot of the best tech founders started out as engineers and learned the business part on the job. Very few people went the other way. So it's a learnable thing. But it doesn't mean it happens by itself. Like you really have to be systematic. The advice part that I would send myself now is like you have to be systematic about training yourself because as CEO, you know, to be effective, you really do need to, it's very helpful if you know a lot about a lot.
24:02And like going, and there's an 80, 20 in each discipline, but there's like a lot of disciplines and a lot of skills you need. So the way I've always broken that down is I've got to keep my personal growth curve ahead of the company's growth curve. And in practice, what that means is think about, well, what is really thinking about what do I need map out like what do I need to know you know one year from now two years from now five years from now and what will I wish I had been learning today to kind of get ready for that because and so you know 2007 when I started the company we didn't really have we didn't really have much of a company there's sort of like there's just like coding uh or my to-do list would have been like let's build a prototype yeah we're going to need to hire a couple people okay if we hire people we're going to need some venture funding branding, et cetera.
24:50Then like two years out, it might be more like, well, we're going to have a product, but we're going to need to get users. So we're going to need to do marketing or figure out distribution. We're going to have to have a business model. And then five years would be like, all right, how do I scale an organization? How do I be a leader, manager? How do I tangle with all these big platform companies who are all going to come after us? So first thing you know is like, those are all pretty different things. And so you have to work back to like, all right, well, what, you know, what do I need to start learning today?
25:17And some of those things you can learn pretty quickly like all right what are the mechanics of raising venture funding it's there's a lot of technical details but conceptually it's not that complicated um but then something like how do i become a great leader or a great manager manager like that's so much longer i haven't get comfortable with public speaking like any of these things like it just takes a lot longer and i think people psych themselves out because they're like oh i you know i didn't i'm not good at this i'm not good at public speaking so i'm not even going to try or it's intimidating to be a CEO.
25:44And so I'm like, not going to try, but I think people sort of, yeah, you in five weeks, you're probably not going to learn to be a great CEO and any more than you'd learn to be a great guitar player, a great doctor or something, but in five years you can go a long way. And so I think that mindset of like, everything's like learnable, um, and the best founders like, and CEOs like end up learning on the job, you know, no one's born a CEO. I think that would have given me some comfort and some, you know, pointed me in the right direction. Were there good resources? I know you're a big book reader.
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26:17And so how much did that help you versus just simply doing and making mistakes versus turning to people for advice that had been down, which was the most useful for you? Yeah, by far reading is the single for me, personally, I mean, different people learn different ways. But I think reading is by far the most efficient because like most of the lessons about leadership or any of the or, you know any of the disciplines you know it's a lot more efficient to like learn from other people's stories and mistakes and try to do them everything by trial and error um but reading for sure i mean even before dropbox like my first company was like an online sat prep company but like i would i was in college and i would just like search for like sales on amazon buy a bunch of sales books search marketing on amazon buy a bunch of marketing books and like that was how i just sort of started getting the initial scaffolding by the way is it true you and your wife both got perfect sat on both 1600 and 2400 is that true yes well researched i had heard maybe two of the only people in the u.s uh but you guys didn't meet over sat we did not meet over sat prep but probably bonded over it uh but after our first date i googled my wife and i was like no way there's an article from some like texas periodical that's the you found it yeah um so mine hers was a little rougher because like she was like right on the bubble of the test went from like 1600 points to 2400 we're probably the same age that was me yeah i was like right right in that and so she had to take both yeah um she got perfect score both times i did not mine was a little more uh business minded right when i was applying to college i did i actually wrote all this software to like flash like to drill the vocab and then um that helped a lot to to i mean i got a perfect score and when i was in high school and then to sort of uh to get ready for the sat prep company which was actually i started because the test was changing and made all those like 800 page books obsolete and at the time there weren't like great like adaptive online learning online courses so that was the opportunity we were going after.
28:26So I went, you know, as a 21 year old to Brookline high school, pulling up in my car and Starbucks and Billy Madison style. Yeah. Yeah. That's for the kids at Brookline. We're like, what is going on here? If only they knew three years later, you would have started Dropbox. Um, that, that, that journey and all those lessons, um, about like, I'm sure everyone has this element of imposter syndrome. I guess as you think back on the 17 years that you've been at it. Do you reflect on each moment with similar nostalgia of like, this was a fun part of the ride? Are there particular points that really stand out either to the positive or to the negative on the journey?
29:11Totally. Yeah. I started Dropbox so soon after college that all of that was just this continuous continuous blur where, um, uh, I mean, so I loved all the stages of Dropbox. Um, I don't know if I loved all of them. I think they were all, certainly the early years were magical in that, you know, you move out to California, a couple of kids fresh out of the dorms or whatever. Um, and you know, you don't even know what you don't know. And you're just trying to build something cool to then you catch lightning in a bottle and have that kind of hyper growth or you know dot-com experience um that i thought i had missed because i i was still in high school during the dot-com boom and i was like oh man maybe maybe i just totally missed it um fortunately didn't um and and then that that hyper growth period where the thing is just taking off and just no matter what you're doing it's just the numbers just going up into the right um it was a really cool experience or sort of like, you know, being a novice surfer and then suddenly being on a wave that's like a hundred feet tall.
30:21You're like, okay. Um, I mean, it's, it's awkward and scary too. Cause you're like, you know, there's not a lot of style points. You're not doing things kind of technically right, but you're just trying to hold on and stay on the board. Um, then it gets tough when sort of the, that wave flattens out or you're, um, or like they're like the natural competitive responses to your thing being successful. So like all of your, all the big tech companies are going to come after you. Um, you have to scale an organization. So there are a lot of, and then we, we launched a lot of new products that we had to shut down, which is a super painful experience.
30:55And then there were ups and downs that, you know, then we had another kind of up period as we went public, a down period during COVID AI happens back up again. So, um, yeah, I feel like either like all of the periods either were like fun to go through in some way, or they weren't fun to go through, but they like were pretty necessary or like, you know, maybe I did need kind of a, to get my teeth knocked in a little bit. I'm curious actually, as you reflect, like the, the reason the product took off to the extent it did in the early days, obviously product was elegant, very well done and, you know, market right timing for it.
31:34Was there anything I've actually not heard in the prep that you did that was actually a particularly good viral distribution hack or some reason that it really shared? Yeah. Well, I think there are a few things. And I think part of why Dropbox was able to thread the needle is we sort of got a bunch of things right in disciplines that usually don't go together. Meaning we needed to... There were a lot of other storage companies or sort of online storage was like the startup cliche, the way that photo sharing or social apps or there's these fad things. Storage was one of those. It's hard to remember now, but there were a million of these things.
32:16Problem is none of them worked really well. And to get it right, you need to get a few orthogonal things right. So you needed to get the engineering right because part of why I built Dropbox instead of just using one of the other services, if one of those services had worked, I wouldn't have started the company. But then I would go into the support forums of each of these other tools and they'd be like, Like, hey, this thing, like, ate my wedding photos. Or I put in my tax returns, not coming out. Like, help. And so that was pretty terrifying to me. Or you'd put in, like, a file with, like, a non-English character, and the thing would crash.
32:48Or you'd put in a big file, and it would never finish sending. All that kind of stuff. So I was like, I don't trust any of these services. I really just want to get it right. And even within the engineering, there's a part that's, like, a more mathy, algorithmic, like, the sync protocol, correctness, rigor, that kind of thing and then there's just like grungy like operating system like being in the guts of the kernel and you know it's like all this and just the plumbing where you had to really we had to like basically cloud enable other people's operating systems without the source code um and even things like putting the i the sync icons on the files so that's just getting it to like work which sounds like most people did not so that's engineering but that was like pretty hard yeah and it was not something where you could throw like lots of people at it you need to throw like a small number of really like experts at it um second is the design and the user experience um a lot of these tools just had a lot of knobs and dials um and ironically actually our early customers if they were searching for like windows file synchronization software they're pretty bad customers because they wanted to twiddle with all these things whereas we wanted to build something simple um but that was even just like i was one of the i was i was that kid in the neighborhood who just get called to fix everybody's computers and then you learn a lot about like here's what easy looks like um so there's a design piece and then as you're alluding to that they're getting distribution like how do you get distribution as a startup um we that was a huge um unsolved problem when we got started like all right is people aren't looking you don't know you need something like dropbox till you have it um for the most part and you know some things like that like tivo like oh you didn't know you needed tivo until you had it but you weren't really looking for it um but i had a bunch of questions like how are people going to find something like that i mean maybe it's like antivirus people don't weren't like shopping for antivirus really it's sort of your antivirus is pre-installed on your computer so like maybe we should go partner with a bunch of big big companies so and then or maybe we should try conventional pr marketing those but like none of those things worked so we were like oh god all right how are we going to get, how are we going to acquire customers?
34:53What really did work was borrowing from a lot of the, um, consumer internet playbook for how you scale these products and particularly like the social platforms. Um, they were the first to really apply a lot of the viral math, which actually came from like epidemiology. Um, so it's things like are not and spreading and, you know, different factors, things that came back into both. Yeah. They'd sort of transplant. Yeah, exactly. Um, so, but you could really, there was a lot of good stuff about how the social platforms were able to go from like zero to millions of users overnight. And things like Facebook platform were all just flying, it was like taking off in 2007 when we were starting the company.
35:37So we were sort of in the, it was all around us, like that sort of virality and the birth of like growth hacking. But we basically applied a lot of the same engineering discipline to customer acquisition. And that ended up being the thing that really worked where there are a couple of vectors. So one was, well, first we tried a bunch of stuff. Most of the stuff didn't work, but the things that worked really worked. So one was this referral program that we created where if I tell you about Dropbox, you know, send you a referral link, you get some extra free space. I get some free, extra free space.
36:12So we sort of double-sided incentive, kind of gamifying the referral process. process and that drove probably triple digit million signups and we put little other bells and whistles on it like we would do it within schools and have schools race against the students in the schools race against each other like which college can have the most like free space um so that you know i still have people who sometimes say oh yeah i got dropbox from that um however many years later and then the other piece was just sharing right and this is more classically viral stuff. If I share a folder with you, you become a Dropbox user, or you hear about it.
36:50And then, you know, and then there was all this crossover of like, oh, I started using Dropbox at home, I brought into work, I started using with my co workers. And then that little team becomes a department becomes a wall to wall deployment. And that's a game of inches, because you sort of have to really think about the funnel starts with a sign up, then how do you onboard people successfully? And then how do you get as many people sharing as possible? And then if you're sharing like Mac, have as many recipients as possible and then make the recipient experience really good like make sure that as many of those invitations are accepted or you know shared things are accepted and so we were we put unbelievable amounts of effort and like sanding down all these rough edges in terms of the onboarding experience so for example when we started maybe like 20 percent of people would figure out how to download the Dropbox app and then put a file in and that was like unfortunately that was like a big kind of limiter on the whole system but then we took we brought five people in off literally off of craigslist we're like here's 40 bucks brought them into our office above the walgreens on carney street in the city and we're like all right go from this email to sharing a file with this email address and they all come and then we were like sort of simulcasting it in the other conference room in the office where literally the whole team we were all watching live as people were like fumbling their way through this none of them succeeded zero of five um but we made this list of like here are like 85 things here 85 little rough edges some big some small we sanded them all down 25 went to 65 percent um and then we did same things with like viral make sure the email deliverability is good make sure the copy's clear make sure there's a few steps as possible contact list importers you know all this stuff so but we then once we got that working suddenly then the thing just it was like an anti-gravity machine it was like a million users two million users 10 million users 20 100 500 you know how many rounds of craigslist people did you have we just said that you know we did that that first one was like humbling enough where we we wrote down so many things that we were able to kind of you didn't need to go back i think we probably did i mean of course we did more user testing yeah sure but not actually but i think that was just like such a searing moment in all of our memories um And even that was born from like in the early days we would get like whenever you emailed like press at actually get Dropbox dot com in the beginning.
39:10But like press at support at like it would actually go to the whole whole company, you know, all 10 people in the company. And so everybody could see all of the customer feedback continuously. obviously um but i got these i remember like reading through the support emails one day and i was the first email was like it's the most beautiful elegant wonderful product saves my life love you and i was like this is great and the next one was like this is the most like impenetrable incomprehensible garbage i've ever used like you mit nerds like can't design a product to save your life and i was like first of all they like personalized it to my college yeah I'm like, you're like, thanks, dad.
39:49Okay. Yeah, exactly. So I'm like, but I'm like, more than any of that, I was like, how can I literally be getting these two emails like one after the other? Okay, we should probably do some music testing. Yeah. But it ended up being one of the most important things that we did. What about, so there was the period of time of just like viral growth and it was a rocket ship ascension through that. And I'm sure there's a bunch of things that you look back on finally. And also you're just hanging on as that wave is taking off. I guess as you reflect on that, I'm sure people would be very fortunate to find themselves in a position.
40:22But is there something that you look back on during that period of time that you wished you had done differently? Or was it just kind of survive in advance as much as you could? I mean, obviously, what sort of is not shown is like there were like 100 other things that we tried with like partnerships with PC manufacturers, antivirus referral programs. Yeah, all the survivorship bias. Other stuff that like had no returns. But, no, I mean, I was super proud of what we did. And there were other things, not just the virality, but also just monetization, like the freemium model, how we acquire business customers.
40:56Like, we were pretty early in sort of self-server, viral, product-led, sort of, kind of transplanting this, like, consumer playbook to business software. I mean, the industry's taken it many steps further since then. But yeah, no, I'm like super happy with how that stuff works. You referenced like having to shut down products, which I'm sure was a hard decision. There was mail and carousel and probably a few others. But you did it fairly, you didn't beat around the bush with it, at least as I reflect on how long it took you to do that. But one, in making a decision like that to ruthlessly prioritize on something, was that an instinctual thing?
41:44Or was the data just telling you, like, this isn't where you need to go? I think it happened gradually and then suddenly.
41:53It was rough. I mean, in 2014, we were spreading our wings as a company. and we knew we had a, I think early on, even like well before then, I think even in 2007, 2008, we're like, we're just going to get crushed by the big companies. And we're just sort of waiting under the shadow of the Google drive hammer that was one day just going to come down and just like, and you were, I mean, to your credit, you were pretty public about when people would say that you're like, yeah, probably like, that's probably what's going to happen. But if not, what could this be? And what could people singularly focused on this problem actually be able to accomplish, which I think is a level of self-awareness.
42:37And also to anyone that's fundraising, at least on our side, it's like, yeah, no, I mean, statistically, most things will get beaten by some competitor and there's a level of self awareness and humbledness that I think in saying that is effective. Well, and then I think when you just sort of start from the user experience where like what two investors, they're like, yeah, this is a graveyard. none of these companies have succeeded it's like it's a commodity um but mainly mainly it's just like too much competition and i was like okay but do you use any of these products and they'd be like no i'd be like isn't that interesting step one in our adventure was not like conquer earth it was like not carry a thumbtry um so and i you know it's also pretty clear like okay even if we did get totally just like mogged by one of these big companies like all the other companies would need some solution or they you know we could sell the company and go do another kind of crazy side project or or whatever but um but that like didn't happen well it was interesting like then all these products launched like iCloud, Google Drive, OneDrive, um Amazon had things in the space like everyone had things in the space and so um but it's sort of like you sort of saw the mushroom cloud in the distance but you didn't hear or feel anything so it's just a very delayed reaction where, I mean, the press likes to write like, oh, you know, Google launches competing product, a startup's just like dead tomorrow.
44:05And it doesn't really, competition is more like a boa constrictor than a shotgun in that you could not look at our analytics and point to a date, our engagement numbers, our revenue numbers, anything, and be like, oh, that's when iCloud launched, oh, that's when OneDrive launched. What it was more like was sort of taking the oxygen, like slowing our future growth or taking our future customers. And then I think what made that, so I would have expected, oh, maybe the 2011, 2012, that whole period when these things launch was going to be the painful period. Actually, that was fine. If anything, it's just sort of reinvigorated everyone.
44:48Like, okay, well, all the competing things will launch, we can't really tell that there's a problem here. And yet, it was pretty clear, like, we were on borrowed time and, like, strategically effed, as one of my mentors might have put it. Where, you know, because what was challenging is, like, we were spreading it. Dropbox was still taking off. But I reckon that it was pretty obvious and problematic that Dropbox was not going to be a great experience for all the different use cases. So we experienced the benefit of Dropbox being such a horizontal general product in that, you know, who's Dropbox for?
45:31What's Dropbox for? It's like, well, what's a computer for? What's a phone for? So this meant we had like an infinity, kind of like literally anyone with an internet connection kind of TAM from one perspective. But then when you think of what people actually do with the product, tons of difference. And it's like, all right, well, people use Dropbox to back up their phone, and they use it to share photos. They use it to replace their file server, or they just run their companies in the cloud. But the ideal products for each of those use cases is quite different. And so what you do from a complementary standpoint with the next act is, if you sample 100 users, you might get 500 different answers.
46:09Yeah. And then, you know, some kind of products kind of die this way or don't reach a lot of products kind of don't reach their potential because they get kind of picked apart from unbundling. Like Craigslist in the beginning was like, you know, Airbnb plus Upwork plus like all these companies, but like all the, the list goes on all kinds of things. but the most valuable verticals got kind of picked off by more purpose-built like oh yeah airbnb is a much better experience for like short-term housing or you know getting a job there's a lot of better alternatives um so we launched things like carousel as a photo sharing service like recognizing that no we shouldn't you know you shouldn't have a bunch of like photo sharing should not be a bunch of jpeg files starting with like dsc 004 what you know right so we built a more purpose-built thing for that and then we're like well we should also branch out from storage and like getting these more like collaboration use cases mobile email or like mailbox we bought this company that was like the first good mobile email client what was the name of the company mailbox it was mailbox yeah and these guys had like a million they had it was a great product yeah they had a beta waiting list with a million people on it and so we're like we haven't seen this since like our own thing and and um bought the company and founders were amazing we made a little bit of a mistake where we put the founders in charge of all this other stuff at Dropbox and sort of the product itself kind of stagnated.
47:29But again, the bigger issue is like, we're just going to get like, everything we build is going to get copy bundle kill. I mean, maybe it was just inevitability. But as you look on that, one, in making the decision, not what you should have done, but I'm curious of that in a second. But like, in making that decision, did you take too many inputs and opinions from people? Do you wish you were more declarative about, no, this is what the company is going to be? Or is this just an inevitable, when you have a lot of different use cases, it's hard to know what signal and what's noise? Yeah, I think we're sort of, so during that, you know, 2011 to 2014 period, I think there were a lot of problems, or kind of a lot of debt that was going to maybe strategic debt that was going to come due, it kind of all came due at once in like 2015.
48:15So what happened was, So 2014, we'll launch things like Carousel, buy mailbox, we're improving these things. But it was clear all along the way that, all right, all these use cases of Dropbox, you're backing up your phone. Okay, so in that market, we're competing against the iPhone to back up your iPhone. How is that going to go? Then in photo sharing, it's like, all right, well, now we're competing against not just Google and Apple, but also Facebook and Snap and Instagram and all these guys. It's like, how's that going to go? Then it was like, all right, well, there's this work use case and collaboration.
48:48And fortunately, that was pretty durable. But even then, we're fighting against Microsoft and Google. So, but I think the question is sort of like the face that faces you or that faced me was like, well, how are we going to get out of this? This is, yeah, maybe it's a little bit time delayed. But, you know, I studied companies like Netscape versus Internet Explorer or MySpace or Friendster versus Facebook. There are a lot of, you know, dead pioneers. And I was like, I see this happening to us. And especially if you start losing. No one wants to work at the MySpace when the Facebook is kicking your ass.
49:32And then even back then, Netscape didn't get killed by Internet Explorer 1.0 or 2.0 or even 3.0. It was like IE3, IE4, IE5. Then that's when things really started. The bottom started falling out. And so we could start to see that happen. 2014 2015 um but i'd say like one of the there were a bunch of notable things like one was google photos launched and just gave away like unlimited free storage to everyone for life just like not even trying to make money um and then bundling it with their phone and just doing all the things that you know an incumbent would do and i'm like wow do we look stupid or more wow do i look stupid um but then like everybody you know all of the industry all of our employees are like what the hell are we doing?
50:18Um, like that bet looked really bad. And so I'd say there was sort of a groundswell internally of like, how are we going to saw it? Like, what are we going to do? Um, none of these things seem viable. Um, and I reread, uh, this book only the paranoid survive. Um, cause we were not the first company to be in this kind of situation. Um, Intel actually had this pretty early in their lifetime. I mean, we all know Intel is like this microprocessor company, but actually they were founded as a memory company, making like RAM for your computer. But then they, you know, long story short, they had all this sort of onslaught of like Japanese competitors that were like subsidized by the government or one way or another, there's like totally on level playing field.
51:01Like they weren't dying yet, but they were probably going to. And Andy walks through that whole, you know, sort of a memoir of that whole experience. And he's like, if we were advising ourselves, or this little vignette where they're in the two of the founders are in Andy's office and he's CEO at the time. He's like, you know, if we were advisors to ourselves or consultants to ourselves, what would we advise? What advice would we give or what would we do? And they're like, oh, we'd get out of the memory business and go all in on microprocessors. And sort of sounds easy, but sort of like Google saying like, yeah, let's get a search.
51:34And then Andy talks convincingly about, yeah, there are these strategic inflection points and markets. And And when you're in one, CEOs normally want to hedge and keep all these options open. That's the opposite of what you should do. You should put all your eggs in one basket. Watch that basket. And the Mark Twain quote. So I'm like, yeah, that's what we got to do. We have to stop focusing on anything else but this collaboration opportunity. Stop thinking about photo sharing. Stop thinking about consumer generally. And it was tough. But I would never forgive myself if we were fighting 10 wars, lost all 10, when we could have won one of them.
52:08And so that's what we did. And I'm like super glad that we did that. And so it was pretty quick. I mean, it was a slow build, but I remember going home, kind of licking my wounds in New Hampshire with my family, like rereading that book. And I'm like, oh God, I got to do this. And so I went back, shut everything down in one shot. I wouldn't say that like solved all our problems. I think that sent like the narrative of the company into a tailspin. Certainly sent morale and all these other problems. but I'm kind of triaging the issues. You know, we, we went from hemorrhaging cash because we were sort of in land grab mode to being, that was the start of being like pretty financially disciplined.
52:46We turned casual positive maybe seven, eight months after that in 2016. But yeah, that was sort of like the initiate that, like the hazing ritual into the big leagues. Like, but it was really, it was really tough. Was there something after that journey that you thought about, reinvesting in? I mean, you subsequently lost Dropbox paper. Now we have Dash on the search side. And so at some point it, you've picked your head up and, and launched other products. So what was that decision to go after and do other stuff after? Yeah. Well, I'd say there was a pretty long period of malaise, both like with the company and then me personally as CEO.
53:29I was sort of like, okay. So we shut down all that stuff. People are like, got it. I understand what we're not doing, but what, what are we doing? and you know the truth is like if i knew the answer to that question like we would we're doubling down like well what is my job i'm like yeah so um and then part of it was also just for me personally like stepping back like like i don't know like this is pretty rough like we built this awesome product it wasn't that like these products were like bad or didn't work actually the product problem was like they were really good and like rapidly copied yeah but i'm like all right what was the scale of the business how many people at this point about 500 people 500 people doing uh, a hundred million doing, yeah, probably a few hundred million.
54:08That's right. Yep. And it's about to be break even. So these are caviar, caviar scale, uh, but you know, some very real problems. Totally. But you know, again, there were Blackberry, Nokia, like a lot of these companies that got way further than we did. Sure. And, you know, um, so it was pretty terrible. And it wasn't even like we had them, it was like, okay, we're gonna focus on collaboration, but we didn't really have an answer of like, um, what that would look like or why we'd be better. And then, you know, for me personally, I'm like, I also not, we just got totally like crushed by an incumbent, like in one area.
54:47So, you know, it's not even just a question of like, what, what do we do? It's, or what can we build? It's like, what, like we can have a hundred ideas on what to build and probably 99 of them would face the exact same fate of being like, oh, cool idea, Dropbox thanks for being free R &D for us copy bundle kill um so that was really the problem yeah decision paralysis of like the or just like what you know yeah you're like okay I'm trying to play chess as well as I can but like they got eight queens in the back and this is this game isn't that fun anymore yeah and so then it sort of drew me to like well why does Dropbox need to exist um if we're just like inventing stuff 10 minutes before you know the big the big tech company is like that's that's cool i guess but it's like really it's not it's not very fun was that the closest you thought of getting off the the ride like selling the company at that point yeah yeah totally it sounds like a point in time most founders would just sell yeah um so yeah it felt sort of like i don't know like being in like in the basement and fight club but not in a cool way it's like like in the yes my i'm bleeding and my teeth are on the ground sure but like i don't know how i'm gonna get up from this um but it's sort of like a lot of these things were all coming together where it's sort of on top of that like this company is like super successful but i'd sort of run out of merit badges to get i'm like we'd raise the money at the valuations we wanted and there's i'm like is this it or is this big numbers bigger um and um you know yeah maybe it's time for my like tech bro ascendancy like maybe i should be flying car working on flying cars or space or climate or you know but not files like we kind of did the files thinking thing like maybe it's done and that would be okay um i think it'd be okay and and i was even just looking at my own experience and i was like okay this is cool um you know the company's like so much more my 18 year old self would be like baffled why i'm upset at all like dude you did it um but you know as i'm just going through running this company i'm like oh man like i'm just in meetings all day emails all night sleep repeat you know uh first world problem but but still i mean you recalibrate to the new normal of all that stuff and like getting your it doesn't matter what your paper bank account says at that point yeah no i was not thinking about money your days are bad my days are bad yeah um and well because i was like trying to really do a retro like all right god i could have totally predicted that these companies were going to respond this way like that was a stupid why did i go after these things i was like so easily countered and that and i was like oh i don't know you knew that you knew that way back in 2000 you always you sort of that that was always the risk but when i was like doing the root sort of trying to do some kind of like root cause and i'm like oh like i really have like no time to think um this and i'm like, well, this is really weird.
57:45Um, because I, my like subjective experience of work is like, I'm just like busy, but I'm not really productive or I don't know if I'm being productive. And like, my brain just feels stuck in first gear and like, yeah, I would have probably had like a better solution to somebody's problems if I just had like some space to think. And then I just like, I'm like, wait, why does knowledge work like work this way? Isn't the whole premise? Like we hire these people for their minds, but then why did we not give them like the space and time to think? And so I just like went down this rabbit hole of like, what is going on with productivity?
58:26And I'm like, something seems to have, something went like very wrong with like the tools we're using where, you know, imagine I would think like, all right, imagine if Einstein were alive today, even back then, certainly still now. But even back then, he'd wake up, he'd check his email, he'd delete a bunch of LinkedIn invitations. Then he'd like, okay, sit down and start working or writing equations. But then someone would slack him, being like, hey, do you have a PDF of that, of your paper? And then, okay, yeah, here, think back to work. The phone would buzz with some tweet. And I'm like, would we still understand relativity?
59:10And then I would talk to people who were actually working on these other moonshots. I interviewed an engineering director from SpaceX.
59:19And I was kind of jealous. I'm like, wow, this is so cool. You guys are actually going to Mars. How does that work? How do you guys work together? He's like, what do you mean? I'm like, I don't know. How do you collaborate? What tools do you use? What's it like to work there? He's like, basically, what's it going to take to put someone on Mars? and the answer was basically a lot of emails and a lot of files And I thought about that and I'm like man okay yes on the one hand emails and files are better than what preceded them but like you have to think of technology not just as a force multiplier but also as a force multiplier but also like the limiting of technology.
1:00:11And the, in our environment at work had become so kind of distracted and overwhelmed or at distracting and overwhelming and full of all this sort of busy work. And these things that were, we were hailing as like the frontier of productivity, like Slack were actually these like distraction engines that are introducing like all these empty carbs, you know, into the, into our experience or just like bombing us or peppering us with all these interruptions. And it was bizarre because I'm like on the, you know, in brain science or even just like common knowledge, like, yeah, people do their best work when they can focus into some kind of flow state, not being interrupted when they're not interrupted, blah, blah, blah.
1:00:53But then we go to work and there's a bunch of like cultural problems, but even just like technically, like the technical environment, the screen we look at. It's like if you wanted to design an environment that made it impossible to ever get into a flow state, like that's kind of what we have. and I'm like, okay, maybe, maybe the real moonshot here, um, the moonshot that powers all the other moonshots is like helping people get back to being able to use their brains at work or like being able to run their brain and something more than first gear or just like not be distracted and overwhelmed all the time.
1:01:27So we, that was sort of the first answer for like, okay, what, what problems are not solving themselves? Because like, you know, a photo gallery in your pocket that was synced to the cloud. We were the first to ship that at scale, but that probably would have happened. And Apple would have figured out. The whole premise of iCloud was like, yeah, your phone should be backed up in the cloud by default. Duh. So a lot of things we were building would probably have been figured out by other people, but I'm like, here is a problem that not only is it not solved, no one's even framing it properly. um and when you think about like the the ultimate non-renewable resource that we have like that i have as a person or my company has or our economy and society have it's like really your brain power right or your time and i'm like we don't even like we're really good at managing money as a species but like when it comes to our like time or our attention like we are completely blind um so we established this new mission for Dropbox to design a more enlightened way of working on the premise that, yeah, the way we're working isn't functioning.
1:02:37Like it's unenlightened, unexamined. It'll look really medieval in 10 years. And I think, yeah, well, civilizationally, we'll look back on this, be like, yeah, remember that we had that weird detour sometime in the 2010s where we basically just like stopped using our brains at work and like put ourselves in these like super cognitively polluted environments. That was nuts. And so that's really what we're, that's like the biggest umbrella 2017 17 and that's led to what products were have been sort of the offshoots from from that for you so the biggest one is dash yeah um i mean we've had other products like dropbox paper we've done some acquisitions but i'd say to really move in the direction of our mission dash is the most important first step and it also requires a couple things so first um covid was another big turning point where, you know, suddenly all of work is digitized and the world recognized, hey, we can work out of screens instead of offices.
1:03:33And that shift had been happening for a while, but like COVID like completely permanently finished the swing. But then that created all these new problems where like now we're using our screens a lot more, putting a lot more stress on the system. And when you're distributed or remote or hybrid or whatever, whatever flavor, same problem, like I can't find the basic information I need to do my job. um and that's a problem because like knowledge work without the knowledge is pretty hard to do um so dash is like a very direct um it's both like a direct response to that problem like how do you make it easier make a better environment that sort of knows what you're working on and can surface this to you um but search is just one piece of it it's really dash is like the 2024 version of the problems we started solving in 2007 problems i started solving in 2007 was like yeah i I didn't like carrying my thumb drive, didn't like emailing myself files.
1:04:23But really the bigger picture was like, I can't find my stuff. I can't organize it. I can't share it. I can't keep it safe because it's like all my stuff is scattered in all these different devices and these different operating systems. And back in the day, the solution looked like file syncing to the cloud and across everything. But today we're sort of back to the same problem. And maybe 100 files on our desktop are now 100 tabs in our browser. and we've talked about search, but there's also problems like how do I organize my stuff, how do I share my stuff? And they're as basic as just like, there's no persistence in the modern world, right?
1:04:59So when you go to bed and wake up, your physical papers are still on your desk, you reboot your computer, your files are still there, but when your browser, your browser sort of clears itself out, either because you close it by declaring tab bankruptcy, or your operating system updates in the wrong way, or one way or another, when you close your browser, it takes all of your state with it. And so if you don't even have like a durable place, what does it even mean to organize anything? What does it mean to organize things across multiple tools? It's just like a broken system. And, you know, files and folders had their problems too, but it's sort of weird that it's like, well, files have folders, songs have playlists, links have, there's like no collection concept, right?
1:05:38So there's a lot of like UX problems hidden in plain sight or things that actually were worse, that were better 20 years ago and worse today. So just the concept of organizing your stuff and then sharing, right? Whether you're remodeling your house or getting ready for a board meeting, what do you do if you have like a Google Doc plus an Airtable plus a 10 gig 4K video? There's no common container that holds mixed format things. And so Dash is really designed to solve all these problems, like both starting with search, but then giving you a start page that kind of organizes your stuff and what you're working on.
1:06:11And the system kind of like organizes your stuff the way that, you know, YouTube or Netflix or Spotify organize your stuff organize your content for you in a consumer context and then sharing like we we have this we have stacks which are basically these smart collections that can hold any kind of content and you know our aspiration is for this to be like the default way to share mixed format stuff on the internet so but these are really kind of solving the same genre of problems that we were successful with and with Dropbox 1.0 but with Dash it's really about how do we solve these in more of like a cloud native browser native modern context i mean we also support your files too but it's we're revolving from storing and syncing your files to organizing all of your cloud content and then that that sort of step opens up a lot of new stuff on the tech tree after that as you think about galvanizing behind a mission like that it obviously started with coming up with the new way of of working and operating which i totally resonates It's amazing how by interruption we operate even today.
1:07:16It just gets worse every day. As you think about setting the mission or the vision around something like Dash, how do you go about identifying that opportunity? I assume there's been a bunch of different iterations on it. Then when you find it, how do you get the company behind it, especially as a public business that, you know, you, you have to share things with shareholders and all that stuff. Um, well, I think you triangulate on these opportunities from a bunch of different directions. Um, and you know, the ones that pass all these filters are the ones you really double down on. So, you know, first as a mission, I talked about, you know, okay, how do we, I think a lot of people agree.
1:07:59Okay. Yeah. Sure. Work is work sucks. I know. Okay. But like, what do you do about it? Right. So where specifically should we try to fix the environment? and then one of the things that what plays to dropbox's strengths so there's sort of a strategy piece of it where it's like well you know one of dropbox's advantages is that we're platform agnostic and a lot of the other companies are going to try to keep you within their garden um dropbox is not going to try to do that and then you know universal search enterprise search you kind of has to be kind of platform agnostic by default because we just don't live in a monoculture world anymore so like everybody has this problem so like okay that's a good fit for dropbox and also requires a lot of customer trust also requires a lot of technical like solving new technical problems.
1:08:38Also, you know, it's also helps if, you know, if step two is organize all your cloud stuff, step one, get hundreds of millions of people to trust you with your files is like a good stepping stone to that. Um, so even if we had gone directly at dash, we would have built all these kind of prereqs along the way. Um, then it's, uh, you know, I, I like to experience things myself and that, you know, just coding the first sort of the proto version of dash or coding a personal search engine myself and being like, whoa, okay, there's a big why now here because there's all these new search technologies that make a completely better experience.
1:09:14But weirdly, enterprise search was kind of a graveyard. Yeah, a lot of people had swung at this. This is an idea. Enterprise search plus ideas like the intranet had been around for a long time. Google desktop search, 2004. So there were also precursor things that were good. So I think Google desktop search is an example of like, that was a great product. But Google kind of killed it. You know, and then plus, well, we seeded the Dash effort by buying a company called Commandee that had been working on this. So I kind of, a lot of things pointed in the same direction. I don't think it was any one like, you know, ah-home.
1:09:55Well, I think that if there was an ah-home moment for me, it was like doing that search myself and be like, oh my God, this is so much better than what I'm doing today. like we have to get after this so that's probably the singular most important thing to me but then it passed all the other filters from like a product distribution strategy standpoint it sounds like there's a lot of enthusiasm right now about all this stuff and ai has been something of a of a jolt for you and totally is the business is that fair that's absolutely i mean i was pretty rough in the late innings of last season when it's sort of like yeah we're sort of checkmate it yeah first of all you know a lot of the workflow files will be around forever and they're still a critical part of um the kind of work experience and they're especially critical with our kind of key customer segments like people that create media or people that do a lot of external sharing like they rely on dropbox it's we're big users for this stuff yeah right so but it's sort of like i don't know where we're in a situation like creating more demand for it it's like is that like blockbusters like how would you create more demand for walking into a store and renting a dv it's just sort of there maybe it's just sort of had its time or it's peaked and so like what do you do about that and then yeah with ai or any sort of new era in computing and like the ones i've been sort of was grown up through like i saw the internet era i saw the cloud and mobile they made dropbox possible and then now ai was the next big one i'm like okay yeah the concrete kind of unfreezes.
1:11:25And for a few years, there's just like this chaos, um, sort of like raining on the racetrack. Suddenly all these people can make all these moves and really change position in ways and create new franchises, uh, in ways that are just not possible when things are more kind of more hardened. So yeah, I got a massive jolt of enthusiasm, both because of what it meant to the market, but then more importantly, what it meant for the technology and the products we can build. Suddenly there's like all these new colors we can paint with. We were talking about motivations a little bit before we started recording at this point, like what along the journey, I'm sure different motivations have come and gone.
1:12:05You don't need to be doing this, doing this next act in command. I'm curious, like why, what keeps you motivated to get up every day and sort of fight this knife fight at different points in time when they had eight queens or whatever you said across the back of the board um well i think it was in the early years it really was kind of the novelty of okay i want to start a company and that's something i had dreamed of and and then that that process can be pretty linear and kind of merit badgy it's like okay let's get into y combinator okay let's raise money from you know venture let's i'm sure the first five to seven years were pretty awesome like yeah serendipitous journey six million valuation now we're going to raise money at 27 million valuation oh we're gonna now we're gonna raise it a 4.2 billion valuation a few years later like it's sort of yeah there was always like these next hurdle i know 10 million users 100 million 500 whatever um so and i think that was part of what made the competitive stuff for that sort of reckoning pretty difficult to sort of like you know not only are we in this like really bad competitive position but now i'm just kind of rudderless like what do i even want to do and so i think like identity becomes tied up in yeah like what do i want to do higher valuations and the, you know, and that's sort of stopped being motivational to me because it's not in, you know, I, I, I certainly like enjoy the process of making a commercially successful company.
1:13:29It's fun to make money. Um, the most fun is like having access to all these interesting people and, and just, um, so there's a lot of good stuff there, but it wasn't like a two X more of that money or valuation was really going to make it that much of a difference, um, um in my life um and so but like going through that fire like did get me through the other side with like a new purpose of like okay yeah this meta moonshot of like helping people use their brains to work that's something that's like unsolved really matters to me something i feel like i can put a dent in um so personal sense of mission and purpose but then also just like all right why do i want to be a ceo um and yeah i'm not really i've sort of cleared what i want to clear as far as, you know, resume.
1:14:15Um, and so I decided like pretty explicitly, I was like, all right, I'm going to do this. Um, keep it. Oh, I really want to get great at the craft of being a CEO because that's something you can, um, like it's totally within your control. It's a, it's something you don't really even master at, you know, in a lifetime, you know steve jobs was probably like just hitting his stride at 55 uh you know 55 56 when he died um so i was like i feel pretty lucky to be in a line of work where you don't like peak in your 20s or 30s because i mean if you're in you know sports or like math or different things um you often have like a sort of artificial ceiling on or you know it's sort of an externally imposed expiration date.
1:15:02Um, but like business and being a CEO isn't like that. Um, and it's painful. And I even when it was like 20 in my early twenties, like I was like, I want a job that gives me, that has like a high learning curve. And I was like, Oh God, well, I certainly got that. Um, and then, you know, I just never get tired of, you know, hearing people's of hearing about how Dropbox has changed their experience. And it's like really gratifying when people say like, oh, I love Dropbox. You know, I will always look over someone's shoulder in a Starbucks to see if the little blue, you know, little icon is there.
1:15:37And that feeling of like, oh, we actually like changed how people do something. You know, or it's certainly at the peak when like people were using Dropbox as a verb and it was like, you know, in movies and stuff like that. Just that feeling of like leaving, just really making something better at scale and that kind of impact is like super addictive. And I think tech was really rallied around that concept for a while. And then tech had a pretty necessary correction with the narrative where stop taking so much credit for all the good things without taking any responsibility for the bad things. But it's always been true that technology is both the source of all our problems and it's still the solution to all our problems.
1:16:22And there's really pick your favorite problem of the world. We're going to need to invent our way out of that. So it's really around the craft and invention and impact that still keeps me going. And just like, I love that the game is hard. And, you know, I think one of the things you have to learn to be on reading or, you know, the more technical aspects of the job are some of the things that are more around a character mindset. You know, you never want to feel like a victim, practically speaking. And you want to focus on the things in your control. and like, you know, you can't control what happens to you per se, but you can control how you respond.
1:16:59So, you know, sure, you know, I'm human. Like I certainly, I'm not not bitter about some of the competitive stuff. But at the same time, like, well, a lot of, there's definitely things I could have done to like navigate us through that a little bit better or stuff that I've learned now. And even when I talked to some of the execs who worked at like Netscape, um i was like man that must have been like that was that was bs like they shouldn't have like copied you know that you blah blah blah microsoft and the guy kind of snorted and they have bill campbell was his name he's like snorted and laughed he's like no trust me our our wounds were entirely self-inflicted and i that just stuck with me as like oh man um uh that's like really honest and i think it's like mostly sure like most of our you know if i'm really honest with myself we've we've had like a long period of stagnation um but that's okay like companies do and you know fortunately tech's a sport where you can hit like a 50 run home run and um and no really nobody really cares about what happened last season i guess you've gotten exposed bill campbell did you get andy grove too did yep you sort of you sort of span both generations of of tech in that way i guess right uh coming up in 07 through this period of time like the old guard was still yeah around in some ways and those two passed away around in the same time and actually that was i left that out i think um you know as i sort of all this stuff was swirling and i'm like what do i want to do in my life and like what do i um uh you know i was at least I was able to read Only the Paranoid Survive and Andy's books.
1:18:44And Bill Campbell was kind enough to spend time with me. We weren't that close, but we went out to dinner a bunch of times, and I was nursing my wounds. And he's like, shut up and get your ass back out there. He'll be fine. You'll figure it out. And I really needed that. Yeah. And I felt like it was so. So Campbell was coached at Jobs and Sergey and Larry and, I mean, on down the list, right? Yeah. And so he's sort of, like, made you believe in yourself more than you actually believed in yourself. Which meant a lot to me because he wasn't an advisor. He didn't have any equity. He got sort of nothing sort of tangible from that.
1:19:24And I was like, that's just, like, so cool that someone would do that. And I really needed it. And then Andy, you know, one of his big inventions was, like, this concept of, like, managerial leverage. And he really, you know, and what's nuts about it, I mean, Andy had a crazy life, like, immigrating from Hungary and all these different things. But, like, just think about, you know, he was running Intel, which was kind of the Google of its time. And, like, in whatever spare time he did, he had, he would just, like, write these books to, like, light the path a little bit for those who may follow.
1:19:58So like, you know, only the paranoia survive, high open management. Like those had a big impact on me. I'm like, at least I'm having this set of problems because if I didn't read that stuff or I weren't exposed to things like this, then I wouldn't, you know, my life would be very different. And so through both. And then when they both died, I was like, man, you know, maybe there's something I should be doing kind of in this vein. Like make it, it should be easier to scale human organization. like we should be man we should be treating our um you know limited brain power with a lot more reverence like we should be redesigning our environment to like like to not have these have these problems and i'm like in this privileged position where i can actually like have i have tons of like capital and resources and people to go do something about it which is like super cool um and but like you know and when i have like so many more so much more leverage to solve a problem like this than either Bill or Andy did.
1:20:55Like Andy, his best like mechanism to make things better was like write a book. But the book, you know, Hypo Management was like published in like 1983. Like of the people who like need to read it, maybe 0.1 % have ever heard of it. And you go all the way down the funnel. You're like, how many people like read it and then take no action whatsoever as a result. But, you know, our customers would tell us like Dropbox is not just the place where I like sync files. This is where I go to work. This is where my dreams come true. It doesn't keep files in sync. It keeps my team in sync, keeps people in sync.
1:21:30People were using all these metaphors even 10 years ago of Dropbox being this workplace or this working environment. And I was like, we had just never thought of it that way. And I was like, man, if we did think of it that way, we would have done things so differently. And so we get to do a lot of that now. I guess one that I think you might be appropriate to weigh in on, but you had a number of successful fundraisers. I'm curious, as you reflect, do you think fundraise and valuation, is that just a rounding error in the history of the company? And hey, raise as much money as you can, and at the end of the day, you'll survive or not on your own merit?
1:22:12Or do you reflect on high valuations or things and say some way that might have exacerbated some of these concerns? Basically, can you say that founders should raise at lower valuations because I can't say that? It sounds like self-serving when it comes from me. When it comes from you, it's more credible. Yeah. Well, I think the way I think about it is more, I mean, especially with some hindsight, like I've been overvalued, I've been undervalued. they can both be quite painful actually being overvalued it can be more painful in some regards so uh yeah for sure i mean we we went from like a raising raising a 4 billion valuation in 2011 to raising a 10 billion valuation in 2014 i wish i could say that our thought process or my thought process i was just like 10 sounds like a good number and investors were willing to give it to it so we took it and then after i just remember afterwards like looking at the market caps of all these public companies and like being like wow dropbox is like more valuable than all like the you know all these like blue chip companies that i really admired i'm like either i'm a genius or i'm an idiot it's like wow and i knew very little about corporate finance at that time and you know i don't i don't think it was like categorically that i think we did over we overshot by a lot um which then made a lot easier to paint this pretty rapid reversal or reversal in the narrative from like, oh, these companies now going from the little engine that could to then the first dead deck of corn and all these things.
1:23:52There's only two narratives, right? It's either up or down, and so you've got to know which side of that. I think if we raised it six, probably much of that would have been easier. But at the same time, I optimize dilution a lot. It's not deterministic. So it's just sort of, you know, you're trying to keep a lot of these things in balance. And importantly, I think whenever you're, the way I think about it less than like overvalued or undervalued is good or bad. I think it's more like, well, just like try to play it, like play the game forward a few steps and certainly work back from like, okay, if we're a public company, you know, by and large, our valuation will not be vibes based at all.
1:24:34it will be like a pretty basic function of like revenue growth profitability some plus or minus based on like sentiment yeah but like if you can't draw you know if you draw the dot where you are today to the dot you were where you would be as a public company um and if like where you're where you're raising is like way off of that trend line um then you're in for then you're leaving a lot on the table or you're setting yourself up for you're like opening 10 years of Christmas presents. Most founders don't generally think they're going to end up on the wrong side of this stuff when they're raising, I've found.
1:25:11Like, I'm sure Zuck doesn't feel like he should have raised at a lower price from Yuri Milner way back when, right? It's like, it's... It's not really practical, but like, I think it's more the things where... How much margin there are. Yeah, it's like, you know, you do have, you know, at some point the market will set the price, but then you do have some latitude to be like, Are we really going to juice it? Yeah, wiggle around. And I think it was compounded by me sort of elbowing it up because I thought, why not? 10 sounds good. Yeah. It does sound good. And it actually wasn't that nuts by modern standards.
1:25:50Yeah, yeah. But we were 250 million going to 400. So 40X revenue multiple going to 25. I mean, it's still very rich, but still 60%. Yeah, exactly. There will be way worse. Yeah. But we spent the next 10 years digging out of that. Yeah. We're still below that market cap today. Just a nerdy one to end on. Data centers. Yeah, sure. When did you decide to do all that stuff in-house? Yeah, it was somewhere kind of the mid-teens, probably like 2015, 2016. We'd been sort of experimenting our way into it for a while. Very contrarian at the time. Yeah, we were like the one car going the other direction on the highway.
1:26:30Because everybody else was migrating to the public cloud. We had actually started on AWS and went off of it. I actually don't even recall. Was it purely cost at the time? Cost was part of it. I mean, it's kind of funny where, I mean, there are actually a few issues. One was, I mean, this one will sound kind of crazy, but you have to remember the public cloud itself was pretty nascent, and we were users of S3. uh amazon's s3 is one of the aws services um the storage service so we're big users of that and then we were growing so fast actually our biggest concern was like are they going to keep be able to keep up with us and like i don't know what our recourse is if like suddenly they can't keep up like like having a hotline and being like hey can you guys please get our like company back up please please please you guys had to have been one of the biggest customers if not the biggest at the...
1:27:27I think we were certainly in the top kind of echelon. I don't know if we were number one, number one, but we were we didn't want to be number one. So there was a first question of is the public cloud even going to scale as fast as we need it to and if something goes wrong, do we have what are our tools to actually make it better if we don't control it? That ended up not being a big deal. Actually, Amazon was a great partner and they scaled just fine but like that was a concern and then it did get a little trickier because like all these guys the public cloud providers were also competing with us like including amazon so you know google had their thing microsoft had their thing um or you know one drive and google drive amazon had like a storage product and so we were like pretty uncomfortable with like all right we're gonna so let me get this right we're gonna like put all of our keys in someone else's hands they're also competing with us what could possibly go wrong so it's more like in a regret scenario i felt like we'd look really dumb um or just you know i felt like the responsible thing to do for our customers make sure we were able to like you know protect their destiny as much as possible um and then but then third yeah cost performance like the the public cloud pricing like stopped kind of following the hardware cost curves down.
1:28:50And, like, yeah, they needed to take margin. But, like, yeah, there's absolutely no guarantee, and probably it was unlikely that we would keep getting cost savings as the, or we'd basically be relying on the kindness of strangers to, like, lower prices on the, and we were only really using the commodity pieces of just, like, raw compute, EC2 and S3, like, raw compute, raw hard drive space. and so we were able to really build a tuned system for just for our workload and then you get not just cost but a lot of performance advantages you can like more vertically integrate across the stack and then that also is helpful for things like as you have more compute that needs to go to the storage or machine learning then there are like advantages like that they even translate into the world today I mean you have to be careful not to we we're very surgical in what we do in our kind of private cloud um because you can sort of end up in a situation where sort of re-implementing the whole public cloud badly um but it's worked super well for us but we're we're a pretty unique yeah case and that it's like you're glad you did it it's super glad super glad we didn't both i'm super glad we started on the public cloud it's really worked out to be on our own infrastructure we still get massive cost and performance savings.
1:30:10We co-design our servers. We go down to the hard drive and the rack as far as how all that infrastructure works. Our teams have done phenomenal things to just keep writing that down. Therefore, we still have software margins, even though you'd think a lot of the storage piece is a commodity. I guess one last one before we hop. Anything that you would say if you're a founder listening. We've touched on a bunch of different things that you've learned or thought of over the course of, you know, 17 years of doing this, but any other lessons or particular insights that you reflect on this journey you've been on that might be useful to lead people with?
1:30:59I think scaling the company was a lot harder than I feel like it should have been. And we've talked about some of the books, which are largely, some of them are on management and things like that. But I think building on what we were saying about narrative culture in Amazon, I'm a big fan of Working Backwards, which is a book that really kind of chronicles the development of all their scaling mechanisms. And I think they had really good insight into what goes wrong as you scale a bunch of people up.
1:31:37And narrative culture was just one part of it. So there's, like, how do you maintain a high talent density and keep raising the bar as you hire people? How do you do business reviews? They basically have this operating system that's really powerful. And I was like, during some of the more difficult years, I was like, I would give anything to like sort of uninstall the operating system we have and install someone else's. And I wouldn't, Amazon, Google, whatever. And it was kind of nuts to me that like, there was like no way to do that. And even like implementing all these things, or these mechanisms are great around the kinds of things we've been talking about.
1:32:14But they're still very manual and human-mediated, and the only real technology is still a memo or an email or a spreadsheet. So I think there's a huge opportunity to, in a world where now all of work is fully digitized, meaning your AI agents or whatever can sort of see and hear and read and write, just like a human can. And that's a very big change in the world from pre-COVID, where no matter how smart your AI system is, if it doesn't have missing cell coverage, if it doesn't know what happens in the real world or if the real action is happening there and the system is blind to it, then that'd be a problem.
1:32:56But after COVID, that's kind of fixed. And then with a large language model where it's like, and then large reasoning models, multimodal models, whatever, but just like these large models, you basically have sort of cognition in a bottle. or SAN that can think. And so I think that it'll be so much, I'm really excited about the kinds of organizations you can build and have, I think we'll see many 10Xings in terms of a team of 10 people can do what used to take a team of 100 and either make small teams perform big or make big teams feel small. I think the whole practice of management is going to be completely different where a lot of the repetitive aspects aspects are going to be automated.
1:33:42And, um, and so I'm super excited about like opening my laptop in 2030 and, uh, having a much more sane and calm and focused experienced. And, and hopefully we're going to have a lot of stuff well before we basically turned Dropbox into this lab for distributed work after COVID and hopefully have a lot of this stuff a lot long before that. Cool. Drew, thanks for doing this. Awesome. Thank you.
1:34:11Thank you for joining this episode of The Logan Bartlett Show with co-founder and CEO of Dropbox, Drew Houston. If you enjoyed this discussion, we really appreciate it if you subscribed on whatever podcast platform you're listening to us on, as well as shared with anyone else that you think might find it interesting. We're continuing to try to grow the show, and so we really appreciate anyone's support and continuing to help us do so. Thanks, everyone, for joining, and we'll see you next week with another great guest on The Logan Bartlett Show. Have a great week. Bye.
From the publisher
Drew Houston has now been CEO of Dropbox for over 17 years. In my latest conversation, he opens up about the pivotal leadership lessons he's learned, the mistakes that shaped the company, and the true challenges of going head-to-head with big tech. We also dive into the highs and lows of fundraising, how valuations can make or break a company trajectory, and discuss the opportunities AI presents for the future of work.
[0:00] Intro
[0:44] AI Opportunities for Dropbox
[5:57] Dropbox's AI Principles
[7:52] Introducing Dropbox Dash
[9:18] AI Enhancements in Search
[12:33] Personal Productivity with AI
[17:10] Memo-First Culture at Dropbox
[22:15] Reflections on Leadership and Growth
[31:21] Early Challenges and Viral Growth
[48:22] Facing Fierce Competition
[51:51] Strategic Shift to Collaboration
[53:20] Navigating Internal Challenges
[55:18] Reevaluating Productivity
[1:03:07] The Birth of Dash
[1:16:32] You Don't Want to Feel Like a Victim
[1:30:29] Closing Thoughts and Lessons Learned
Executive Producer: Rashad Assir
Producer: Leah Clapper
Mixing and editing: Justin Hrabovsky
Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA
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About the Show
Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member.
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