Dropbox

“So actually my previous role at Dropbox, my team was a couple hundred people because it was growth was a really big driver for Dropbox. It was a very heavy product led company and our team was bigger than marketing team as a whole.”

“Dropbox was a tool for everyone. So that made it harder to be specific about what needs you were serving even as you moved into enterprise. Whereas like, Figma was way more focused on the core audience, and even for prosumers, even for SMBs, it is a profession…”

“They sent Drew, the founder, a term sheet. They faxed it to him. Anybody even remember what a fax machine is? They faxed him a term sheet with a blank valuation.”

“I'm not sure what the right thing is going to be. If it's going to be some company that can say, all right, we're as an independent body, we're not trying to like push into any particular product. It's our job to be like the skill authority and we provide I do…”

“I have to give credit to Drew at Dropbox. He was like the first guy in that game.”

“Dropbox growing minus one percent a year is not crushing it, is it?”

“However, what I can say, it's on par with benchmarks of other B to B SaaS products that I've ever worked at. And I worked with Miro, Dropbox, SurveyMonkey, Netlify Amplitude and others.”

“These companies, they're in a much more bounded world now. They might grow 15%. They might grow five percent. They might trade at six times revenues. They might trade at four times revenues. You know, if you look at the stock chart, the area of magic is gone, …”

“We're just going to draw a hard line. We're never, we're just not going to do that. Because of this trust conflict or this incentive conflict we would have.”

“We have half a million paying businesses on Dropbox, two and a half billion in revenue.”

“So for example, for Dropbox, they do have a product principle called Cupcake. For Snowflake, they have something called Superhero. I mean, the names could vary, but the meaning is exactly the same. I mean, it's all about bringing joy to the customers.”

“That was the first million dollars, would have been a two billion dollar return because I'm like, what is this thing?”

“When you're at the Dropbox stage in terms of growth, it's just when you need acquisitions the most, But you find it hardest to do as a public company, because you're still in the low-growth penalty box, and that must be a frustrating place.”

“And he has 18.2 million paid customers now, but you know what it turns out? That's the whole world for him. Like it was crazy. And then for it's 18.2, because he literally has maxed out the global market share for what he has.”

“So we actually scaled the company to like a 150 people or something. It was way more than 70 people, but we hired a lot of managers, like senior executives, people that had come from companies like Meta or Dropbox or others where they'd been used to having 102…”

“Billing was really honestly more of a product surface than a, like a once a month workflow.”

“Like at Dropbox, for instance, our billing system was built by interns every summer. Like it would get updated every summer because the only people we could convince to work on it were like interns.”

“The commercial model of Dropbox incentivized, it was a team-based thing, number of users. It incentivized us to get really good at getting a wall-to-wall deployment. Did not incentivize us at all to drive incremental usage. In fact, in a very literal sense, yo…”

“Your right to win is predominantly in your existing customer base, and ServiceNow is a big one, and Salesforce has a big one, and brutally in the enterprise, Dropbox doesn't.”

“Even if Dropbox had shipped a perfect, hear me out, even if Dropbox had pitched a perfect functionally equivalent product to Glean, it would mean that for their existing business customers, which is a smallish percentage of their total business, they would win…”

“Even though I would largely say Dropbox looks like a failure from the outside, like, or to me, from my point of view of like, they haven't really done much. They make a lot of money. And so it's a successful business, you know, just like IBM somehow is still a…”

“And it was all license-based as well. And that was the interesting thing. So it was, you know, you would buy the license of, I don't know what password, four, maybe it was, or three. I can't even remember the version back then. And you would hold that and then…”

“The thing that ChatGPT is becoming and continues to get better at is memory. And just like we've seen at Apple, Dropbox, like many places where data is a moat, like...”

“Asking someone, hey, you're, you have this career path at the Silicon Valley company, you have this mortgage, you have this annual bonus, like, do you want to make one third of that amount and like sit in a room with us and see if this will work? It was like a…”

“I actually had that happen to me at Dropbox not so long ago. Somebody reached out and they're like, oh, I look like it was like some page and activation flow and they're like, oh, I love this page. This is so cool. I love what you've done here. And like, I'm g…”

“Now, for example at Dropbox, over 50% of acquisition comes through sharing.”

“Most of growth loops spin out a their ability to produce meaningful results for you within the first five to six to seven years.”

“And then it hit the top of Hacker News for two days, which doesn't, I don't think it can really happen anymore.”

“We put this video on dig and read it and our beta waiting list went from 5000 to 85,000 people overnight.”

“Going from, you know, maybe seven, six million valuation in 2007 to twenty seven million in 2008 to then four billion valuation in 2011, you know, being on magazine covers, just that whole experience was wild.”

“Steve Jobs was like on stage in 2011 announcing iCloud, calling out Dropbox by name as something that will be viewed as archaic.”

“The products launched, but you would never be able to look at our numbers and see when that happened.”

“The problem is that every incumbent is gonna copy your product, they're gonna bundle it with their platforms, and then they're gonna kill the economics.”

“I killed carousel, killed mailbox. Went all in on productivity. To some extent that was an easy, a relatively easy decision because most of our subscribers, you know, 80% of people paying for Dropbox were using it at work”

“There's a big time lag where between when these products launch and when they actually have an impact, because often it's not so much the existence of the product or its availability, it's the sort of Constant bundling or the constant iteration or, you know it…”

“One thing that happens when you're a founder and your company succeeds is your identity is fused with the company. And so it's easy to get in a situation where you only feel good if the company's, or however the company's, how you feel is how the company is do…”

“Everybody's got strength and weaknesses, but as CEO, like, you know, both your strengths and your weaknesses are massively amplified. And a lot of blind spots in your personality can become huge cultural dysfunctions in the company.”

“I felt like I had done that. That's what, that's a big part of the problem that led to a lot of this chaos at the end of the chapter two, where I was like, oh man, I'm on this, I'm doing stuff, but I'm clearly not setting the right direction or people are conf…”

“They were faster. Your company grows and rises. The easier it is for new people in the company to think they hit a home run instead of You know, starting on third base. And so a lot of complacency and entitlement and preoccupations with things other than our c…”

“Many in SAS SaaS productivity have this sort of sophomore slump where you have a super successful first product, but then it's challenging to build like the next, you know, the next platinum album. Right. So, you know, Dropbox has fallen into that category. Yo…”

“You try to build multiple products in a functional org, but then you know, you lose accountability because people are like, well, I'm spinning a lot. I'm trying to make Dropbox work and I'm trying to make mailbox work and I'm trying to make paperwork and all t…”

“The only thing that really worked to even just like keep the lights on was basically giving people like double promotions so that they could justify the, you know, someone who's a director at company X, like making him a VP at Dropbox. And then you had to do t…”

“Every time you move up a league, your reward is a stronger and better and opponent and potentially a more on level playing field.”

“I think burnout is the biggest thing that will sort of kill you.”

“When we launched dash, we usually do like a press Thing. You know, conventional press, tech press, we got like almost no coverage for it. And yet all the stuff we did on social or going direct was like way, way, way more impactful.”

“In 2007 too, like we, instead of hiring PR firms and buying AdWords and stuff, we were creating these like viral videos and we were using math, you know, using math from epidemiology to create these viral loops. In a lot of ways, Dropbox took that transplanted…”

“You need to understand what game you're playing. And you need to get good at the micro. It's not that like the meta is more important than the, it's like you need to do all three at the same time. And so that's really the hard part.”

“One of the best predictors of an exec continuing to scale It's not just how, what they know or what they can do, but like the extent to which they can actually like be aware of their failures and not blame or dismiss things.”

“It was 20 founders, CEOs that You know, did that seed round. It was the founders of PayPal and Instagram and Mint and Eventbrite and Stripe and Nest and a whole bunch of really incredible businesses Box and Dropbox.”

“Dropbox, Dropbox, like with the referral program, Groupon and email, Pinterest and SEO, Duolingo, and just like a totally unhinged social media, right? All of them were kind of first to this concept and it really, really worked.”

“While they're talking about this, Sean Parker actually comes up with a name for the product and is like, oh, if you launch this, you should actually call it Dropbox.”

“I spent, I checked, I think it was probably, like, over 400 hours this year, so far, coding, because I had my paternity leave, where I was able to work on some special projects.”

“We decided to basically turn, we went like 90% remote, we still, the in-person part's really important, we can kind of come back to our working model, but we're like, yeah, this is, everybody is going to be in some kind of like distributed or hybrid state, so …”

“I think you really need these like hybrid architectures that where you have very like purpose fit tools or, you know, you're probably not using Sonnet three, five for all of your normal product use cases. You're going to use like a fine tuned eight billion mod…”

“A lot of Stuff that used to be in, you know, Word docs or Excel files, like, all that has tilted towards the browser, and that tilt is going to continue.”

“So with Dash, we wanted to make something that was really, like, cloud native, AI native, and deliberately, like, not be tied down to the abstractions of the file system.”

“The value of Dropbox has never been, we provide you, like, the cheapest bits in the cloud. But it is a big pivot from Dropbox is the company that syncs your files to now where we're going is Dropbox is the company that kind of org helps you organize all your c…”

“Now, the problem is the same. The shape of the problem and the shape of the solution is pretty different. You know, instead of a hundred files on your desktop, it's now a hundred tabs in your browser, et cetera.”

“Actually, we'll, like, integrate with Google Drive, we'll integrate with OneDrive, Really any of the content platforms, even if they compete with file syncing. So that, that's actually a big strategic shift. We're not really reliant on being like the store of …”

“You know, we also know there's like infinity investment going into like the work agents. So we're not really building like a copilot or Gemini competitor.”