Evidence receipt / belief
Published · transcript-backedDrew Houston: belief
9 Jan 2025 Lenny's Podcast Behind the founder: Drew Houston (Dropbox)
“I think one of the big challenges or lessons from this whole period is that one, is as part of the problem we had with competition, and this chapter two was external, but a lot of it was internal, where we couldn't organize ourselves effectively.”
Source trail
Everything needed to verify it.
- Speaker
- Drew Houston
- Attribution
- Verified speaker
- Claim type
- belief
- Recorded
- 9 Jan 2025
- Publisher
- Lenny's Podcast
Transcript context
…Yeah, it went nowhere for a couple of years, but then after COVID, and after we're dealing with all these information problems, I'm like, "Yeah, we should be the company that helps you get the right information at the right time to the right person." I built that little hacked up search engine thing that I made, might be an ingredient to this. We bought a little company called Command E that was doing universal search, and we created this new product called Dropbox Dash. Basically, Dash connects to all your different apps. It gives you universal search. Then obviously after ChatGPT, not only can you do conventional search, but you can ask questions in natural language, and answer a lot of the questions that ChatGPT can't because it's not connected to your stuff. If you ask ChatGPT like, "When does my lease expire? Where's that slide from last year's product launch," can't tell you because it's not personalized. Because it's not connected to your information. We did all of that for this whole connector platform where we index the known universe of SaaS apps, have this kind of intelligence engine that brings all of it into a common representation, and lets you do conventional search, natural language search. Then more than that, we want to organize your working life for you. Stepping back even further, often it happens that a company likes to starts solving a problem, and that problem is never permanently solved. In a lot of ways, Dash is the biggest, best embodiment of solving the same kinds of problems I started Dropbox to begin with. Because on the one hand, I was talking about thumb drive, but I wasn't, really. If you think about the higher level job to be done, I was like, "No, the real issue is that it's super hard to find my stuff, organize my stuff, share my stuff, and secure my stuff." In the beginning that was like my stuff was my files, and the scattering was across devices. Now, the stuff is tabs in my browser, and cloud tools. But it's a lot of the same problems. We've talked a lot about search, but then organize is still a big problem. There's no desktop folder or desktop as in the physical realm, when you're in your browser. It's just this ocean of content that washes by you. Then you get tired. You nuke the whole environment. But there's nothing to come back to. There's no collection concept. Files have folders, songs have playlists, links have ... If you're getting ready for board meeting or remodeling a house, there's no common container. If you have a Google doc, and a 10 gig, 4K video, and an air table, this is a new problem. Dash also has this thing called Stacks, and has basically smart collections that helps make sharing a lot easier. But again, a lot of this was an intersection of like, "Yeah, how has work changed since COVID? What crazy little science projects have I done? Then how should one find, organize, and share their information in the cloud era? If I were to build Dropbox today, what would it look like?" nce COVID? What crazy little science projects have I done? Then how should one find, organize, and share their information in the cloud era? If I were to build Dropbox today, what would it look like?" Dash is first part of the answer. We're super excited. But we just launched it two months ago, and signed up our first customers. Then I can come back to just rebooting the core business too. I think one of the big challenges or lessons from this whole period is that one, is as part of the problem we had with competition, and this chapter two was external, but a lot of it was internal, where we couldn't organize ourselves effectively. The business has scaled so much faster than our ability to manage it. First is to recognize this is not an unusual problem. Many companies, not all, but certainly many, and actually many in SaaS productivity have this sophomore slump where you have the super successful first product, but then it's challenging to build the next platinum album. Dropbox has fallen into that category. You could say Zoom, Slack, others. First, it's easy to feel bad about it yourself, but no, you're not. This is actually a very common problem. Then there's a lot of solutions. People devise lots of solutions to this. Part of it's structural. Your company has to go from a pretty fun, and stable state of a functional organization where you have engineering in product design, there's one product, and there's one customer. Everybody's working, we are all in the same direction for the same team to then when you have multiple products, then you have all these conflicts. How much should we invest in the core business versus the new thing? Who should have authority in the company? You try to build multiple products in a functional org, but then you lose accountability. People are like, "I'm spending a lot. I'm trying to make Dropbox work. I'm trying to make mailbox work. I'm trying to make paperwork, and all these things." Then you respond by breaking up into groups or business units. We have a product business unit, product GM structure. Then you have to refactor things to have a common technical platform, and all the GNA functions. There's this metamorphosis, and maturation you need to go through that is mega obvious to experienced people. That you're just totally blindsided by this if you're solving it by trial and error. There's a great book, Zone to Win, that talks about some of this, what needs to happen internally by Geoffrey Moore. Then there's a lot of cultural problems that set in. We just touched on some of them at a high level. But whether you're in a company or an empire, a civilization, what gets you to the top turns out to be pretty similar things. You have this outsider, challenger mentality where you have to eat what you kill, and the odds are against you. Through hard work, learning, and grinding, you start moving up the curve faster. But then once you're successful, then there's a temptation to take the foot off the gas or enjoy the finer things in life or just focus on other things, be it other than what got you there. ve faster. But then once you're successful, then there's a temptation to take the foot off the gas or enjoy the finer things in life or just focus on other things, be it other than what got you there. I think what we experienced, many other companies experienced, Bill Campbell experienced in Netscape, the success plants, the seeds of failure in terms of complacency, entitlements, or taking your eye off of what got you to be successful in the first place, yeah, I went from earning a lot of the early stage startup founder merit badges to earning the stagnation, and irrelevance merit badge. Now, the turnaround merit badge. Part of that is the turnaround playbook. Okay, first, it's just getting out of this delusional state where you think you're great, just splashing cold water on everyone, and be like, "Look, we haven't shipped any. Last three years, the only thing our customers have really meaningfully seen from our product is a price increase. What the hell are we doing?" A lot of it is getting back to like, "Hey, we have to focus on craft. We have to embrace a growth mindset and learning. We have to stop blaming external factors or displacing blame. We have to be a high agency culture." There's a cultural transformation that you have to personally embody, and be clear about. Then in our case, we had to reboot the whole exec team. We've had all the time getting the right kind of leadership team in place for the end of chapter two and three. Part of what happens in conjunction with a lot of the cultural stuff I just talked about, is also you can have this as the talent flywheels flying forward, and flies in reverse. You have a new set of issues where you get all these amazing people in the company, but they want to work for Facebook, not MySpace. You start having retention problems when the narrative goes negative. We start bleeding talents, and then it's also really hard to hire people for the same reasons. Especially, as I think about where the big lessons from chapter two that we've addressed in chapter three, the seniority gap is something that can accumulate because much of the talent can fly to the next shiny thing. What you do in response typically is, you promote a lot of people internally, which is good for them. It seems good for them in the short term, because they're just getting a lot more authority, and responsibility quickly. People like that on day one. But it's a problem because suddenly people are solving problems through trial and error. Things may be new to them that are not new to the industry, and suddenly no knowns to the industry are unknown and knowns to those leaders. Then usually you can get around that by hiring a layer of experienced execs or having enough of them in the company. But in the talent wars of the late teens, we were in the situation as were many companies where, any exec you talked to with any experience had five offers from fan companies for three times the comp, and a third of the workload, or 10 offers from pre-IPO startups, and C-level roles. These are offers in hand.…
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