The Exchanges

Q more megabytes, and so I joined, and then when I bought, I just put my credit card on, and now I've been a subscriber, I think, for two or three years, but you're saying that that's not the way it works with bigger companies. Do you call out to them, or do you wait for them to, to request a call? How are you getting big companies to sign up?

A So, so step one is a story more like yours, where, you know, someone who's just working in a department starts to adopt the product and share it with their group, and, and then it kind of mushrooms out from there, uh, and then, uh, often it will get the attention of IT, who's like, well, okay, how, how do we, you know, deploy this in a formal way and get some of the visibility and the control that we need, um, and so usually the first adoption is, is organic, and, and often it'll be Clumps of people or individuals just buying pro accounts, um, for themselves, maybe using the corporate credit card. And then, uh, to answer your question about is it do we call them or they call us? It's, it's a mix of both. So smaller customers will often call us and then We'll, we'll often have companies that have hundreds or thousands of Dropbox users. Um, they might just might not realize it yet. And so, um, those are the kind of folks that we'll call them and let them know that we have a business offering.

AI assessment note: “to answer your question about is it do we call them or they call us? It's, it's a mix of both.”

Q helps what he calls micro entrepreneurs build their businesses. Wondering, there are a lot of great companies that are in that micro entrepreneur level, but they're not going to get to the billion and beyond level that you've gotten to. If you could give them advice about how to break through that and go from micro to macro to giant, what would you give them? What would your advice be?

A Um, well, I think the first thing is the reason that companies, the first reason that companies don't become billion dollar businesses, for example, um, is that they don't have billion dollar markets, and so whenever, and this was true of my last company, right, I started an online SAT prep company, and, you know, our audience is limited to, you know, teenagers who have to study for the SAT, right, and you do it once, you're not gonna buy it again next year, hopefully, um, And so that put a cap, I mean, it's still a big market in aggregate, but it's, compared to something like Dropbox, it's pretty limited. And so, the first really important choice is what kind of market do you go after, and, and then, and, and even if you're going after something smaller, is there a way to expand it, ah, expand what you do, Um, or reframe what you do so that you can go after a bigger audience. Cause even if you're going after a massive market, you still have to pick a first niche. Um, we sort of picked Windows file synchronization, uh, as our first niche, um, when we were really trying, aiming at this much bigger problem of like how do you have your stuff with you wherever you are and solve all these other problems. Um, the second is to surround yourself with people, um, who have done this, who have built businesses like that. So, by taking money from Sequoia, um, our first venture investor, um…

AI assessment note: “the first really important choice is what kind of market do you go after”

Q A previous guest. He said, can you ask if, if Drew and Dropbox learned anything about B to B sales and B to B conversions? What have you learned about that that you can share with us?

A Well, um, so this has been kind of a big adventure for us over the last couple of years. Um, Certainly my hope was that we just make a product and it would just, uh, sell itself and people just swipe their credit card and it would all be good. Um, it's been a little more involved in that. Um, we have, among other things, we've built a sales force, um, and had to Do a lot, especially as Dropbox has become more pervasive to get IT comfortable with it, and so on. So, um, and I think the reason for that is it's, when companies are putting all their crown jewels in Dropbox, they are often adopting a service like this for the first time. So, um, they want to know that if they ever have any issues that they can get on the phone, um, and they want to know if they have any issues that we will help keep their stuff secure, and so it's been a little bit more involved than I thought, and also some internal challenges around the culture, like, How do you, how do you build a company that can address both consumers and the enterprise at the same time?

AI assessment note: “we've built a sales force, um, and had to Do a lot... to get IT comfortable”

Q How do you know that there, that there are companies out there? How do you know which companies have thousands of users already on Dropbox that you should call out to?

A Well, so there's, sometimes it's really easy to tell because there'll be, you know, you'll have a bunch of users, Sharing a bunch of documents, uh, all on the same domain, right? So, you know, just a random company, right? Pick Cisco. Cisco has a lot of users on Dropbox, and then, um, you know, they'll either reach out to us, or we'll reach out, we'll reach out to them saying, hey, you know, you have X users, At Cisco.com, plus you probably, if you're like other companies, you probably have a bunch of other people using it who, ah, who have a bunch of Gmail or other webmail domains, and so we give, ah, admins tools to kind of consolidate that, um, and, and, and make them manageable.

AI assessment note: “you'll have a bunch of users, Sharing a bunch of documents, uh, all on the same domain”

Q I asked her, what is it about Drew? What makes Drew Houston a success and other people not? What makes, she didn't know. She didn't even know how I could come up with, I mean, she couldn't identify one thing and we couldn't come up with a question that will bring it out. So I'm just going to ask you straight up. Why? Why were you able to do it?

A I think that's, that's a, I mean, it's an interesting question. Um, I think Dropbox happened to be an idea I was really excited about, and then, um, I was really fortunate to team up with a good co-founder, and move out to San Francisco, and surround myself with, um, great investors, and, and hire great people, and, um, and the, doing the sum of those things, like surrounding yourself with good people, and getting an environment that can help you grow your company, sort of like moving into a faster lane of traffic, um, and And I, so I, so I think that those are the most important things, like setting up the environment that kind of pulls great things out of you, um.

AI assessment note: “setting up the environment that kind of pulls great things out of you”

Q What is it about your environment that helps pull such great things out of you?

A Well, I think it's, when you take money from a top tier VC, they, they kind of have a playbook of how to take a couple scruffy, you know, early twenty-something engineers and help them, help shepherd them, ah, through building a big company, ah, Second is we got a lot of great angel investors and prior entrepreneurs who, who have taught us a lot, and among other things, um, some very foundational ideas that they had, such as, you know, really being obsessed with handpicking every person you bring into the company. Those are now really deeply embedded in our cultural foundation, and that's kind of a, um, that it's, that sort of continues to pay interest when you're able to be pointed in the right direction from the beginning, and then Honestly, a lot of things, the stars have aligned for us in a pretty special way. So, um, I started working on Dropbox just because I thought it was something that would be interesting for, or it would be useful for myself, um, and I had an idea that a lot of other people would want it, but, but Arash, my co-founder and I could never have predicted How quickly things like mobile would take on, and, and how much bigger this problem would become for so many normal people and, and businesses, and so, um, I think timing, you always hope that, uh, er, er, timing and, and, and luck, um, or at least things outside of our control, or ended up being on our …

AI assessment note: “when you take money from a top tier VC, they, they kind of have a playbook”