Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20VC: How Founders Should Think Through Distribution and Customer Acquisition Today, The Challenges of the Digital Advertising Duopoly Currently & How To Structure Company Post Mortems Effectively with Gabriel Weinberg, Founder & CEO @ DuckDuckGo About this episode Gabriel Weinberg is the Founder & CEO @ DuckDuckGo, the Internet privacy company that empowers you to seamlessly take control of your personal information online, without any tradeoffs. Over the last 12 years, Gabe has scaled DuckDuckGo to doing 1.6Bn private searches every month, a team of 83 full time fully remote employees, raising funding from some of the best in the business; USV and most importantly, being a profitable company. If that was not enough, Gabe has also written two phenomenal books, Traction and Super Thinking. CLICK TO PLAY CLICK TO LISTEN ON ITUNES In Today’s Episode You Will Learn: 1.) How Gabriel made his way into the world of startups and came to found one of today's leading search engines and privacy companies in DuckDuckGo? 2.) Gabriel decided to raise $13M from USV 4 years into the life of DDG, why did he believe that was the right time? Why does Gabe believe that DDG never needed any primary capital? How does Gabe advise founders to think when it comes to chasing profitability early? How does Gabe view the relationship between growth and capital? Are they in conflict or aligned? What does Gabe make of the many $100M rounds getting done today? 3.) How does Gabe feel about the lack of free and open distribution today? How does Gabe strategise when it comes to channel diversification? What is the right level of marketing channel diversification to have? How do you know when to really double down on one that is working? How should founders be thinking about channel saturation rates? What have been Gabes biggest lessons on payback period over the last 12 years with DDG? 4.) How does Gabe feel about the digital advertising duopoly on the internet between Facebook and Google? Why does Gabe argue that this duo of incumbents are so much more powerful than any other prior generation of incumbents? How does Gabe think about strategies to reduce their data monopolies? 5.) DDG is 83 people and fully remote, what have been Gabe's biggest lessons on what it takes to run a fully-remote team from Day 1? What mistakes did they make? WHat would Gabe advise founders contemplating the fully remote strategy? Why does Gabe have nor formal hierarchy or org chart internally at DDG? Why is this so important for culture and employee morale? Items Mentioned In Today’s Show: Gabe’s Fave Book: The Advantage: Why Organizational Health Trumps Everything Else In Business As always you can follow Harry, The Twenty Minute VC and Gabe on Twitter here! Likewise, you can follow Harry on Instagram here for mojito madness and all things 20VC.
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Harry Stebbings? You are listening to the 20 minute VC and Founder's Friday with me, Harry Stebbings. And I always love your feedback on the show and I respond to all messages on Instagram at H Stebbings 1996 with two Bs and it would be so great to see you there. But to the show today, and I've wanted to do this one for a very long time now, having been a fan of this guest's two books. And so I'm thrilled that we could make this happen today. And so with that, I'm delighted to welcome Gabriel Weinberg, founder and CEO at Duck Duck Go, the internet privacy company that empowers you to seamlessly take control of your personal information without any trade offs. Over the last 12 years, Gabe has scaled Duck Duck Go to doing over 1.6 billion searches every month, a team of 83 fully remote, full time employees, and also raising funding from some of the best in the business, USV,
0:43 Harry Stebbings? and also, most importantly, being a profitable company. And if that wasn't enough, Gabe has also written two phenomenal books, which you have to check out, Traction and Super Thinking. But before we dive into the show today, I'm sure you've heard about it, but my word, I just love the Carter product. Carter simplifies how startups and investors manage equity, track cap tables, and get valuations. Go to Carter.com/20VC to get 10% off. More than 800,000 employees and shareholders now use Carter to manage hundreds of billions of dollars in equity. And Carter now offers fund admin, so you can see real time data in the Carter platform and work with Carter's team of experienced fund accountants. Again, go to Carter.com/20VC to get 10% off. I really do so love that product. But to
1:27 Harry Stebbings? get a deal done, you really need to build that relationship and there's nothing like meeting face to face. And there's nothing like Zoom to make that happen. Zoom lets you connect and do business across town or across the world. Zoom ties together all of your communication needs into one easy platform for video conferencing, phone calls, group chat, webinars, and your conference rooms, and connect easily from anywhere, your mobile phone, your laptop, or conference room. And Zoom is how business gets done. Get your free account at Zoom.com today. Meet happy with Zoom. Again, that's another one that I couldn't spend a day without, to be quite honest. But now it's time for the show and I can't wait to hand over to Gabriel Weinberg, founder and CEO at Duck Duck Go.
2:12 Speaker 01 You have now arrived at your destination.
2:15 Harry Stebbings? Gabe, my word, I've heard so many great things from Brad at USV, from Rick at Guru. I've also just wanted to do this one for a very long time. So thank you so much for joining me today, Gabe.
2:23 Speaker 02 My pleasure.
2:24 Harry Stebbings? I would love to kick off today though with a little bit on you. So talk to me, how did you make your way into the world of startups? But also, how did you come to found one of the world's leading search engines in DuckDuckGo?
2:33 Speaker 02 Okay, super briefly, I was a physics major, didn't want to do academia and thought basically on a whim that startups seem cool. It was obviously the cool thing to do in 1999, 2000. And in particular, thought it might be a cool way to change the world a bit. And with that kind of idealistic, right out of college attitude, started an educational software company that went to admittedly nowhere, but really liked the industry and just stayed in it ever since.
2:59 Harry Stebbings? You mentioned your entry there and I always go off schedule. I don't quite expect to go off this early, but you mentioned the entry there being at that kind of critical time in the excitement of 1999, 2000. It means you saw the bust of 2000 and 2001 and then 2008. How did that impact your mindset? Really building DuckDuckGo today, having seen that hard time?
3:16 Speaker 02 Well, I tried to raise money right at the bust and that obviously failed. So I couldn't raise money. All of that company didn't deserve probably to raise any money. So that's one thing. And I started the next company in kind of that bust. I just never even thought about really raising money again. So the next company, we actually sold that company, but never had any investors or employees, actually, which is me and a partner throughout the whole time. And then when I started DuckDuckGo, I just had that mentality. And so also bootstrap that for the first four years. And, you know, really didn't take venture until our Series A, which was in 2011. So 11 years into my whole startup career.
3:52 Harry Stebbings? Why did you decide that was the right time to raise the money that you didn't? And why then is that critical junction?
3:58 Speaker 02 So I am, despite being my entire career doing startups and seemingly taking big, bold risks, I'm relatively risk averse as a person, especially with capital. And I've realized this doing angel investing, that I'm not the best investor because of that. And that's understatement. But in any case, I realized that I was really on to something with DuckDuckGo that people really want and need privacy. This was back in 2011, pre-Snotin, but I could really see that the world was heading into more and more data collection and there was no counting, balancing force. And I was sitting on something in a major market in DuckDuckGo and search, where people were really starting to switch to it. At the same point, it was literally just me for four years. So I wrote every line of code. I did all this customer support.
4:39 Speaker 02 I did all the marketing. And you can tell that's kind of crazy. And I can tell that it was capitalily starving the opportunity. I had enough money to put in to start building out a team, but this is still the risk averse and also kind of the wife test, who's also a risk averse, wasn't as interested in that. And so we set out to raise money just to give us some buffer, basically. Ended up being that we became profitable pretty quickly and didn't really use any of the money that we ever raised. But it really helped free up the mentality that we could take bigger risks.
5:06 Harry Stebbings? Talk to me about that, because you said before DuckDuckGo never really needed primary capital. So you know, me being the venture nerd I am, why was that? Was that because of the profitability so soon? And how did that become the financial situation so early?
5:18 Speaker 02 I think it's three things. One is I was really willing to do every single job and learn it. So that first four years where a lot of people would have built a team, it was just me. Another thing is, you know, I was lucky enough to be able to take no salary during that period. So there was a long kind of privileged period where I didn't need it just because it was me. And then the second thing would be, we went after arguably the biggest market on the internet, right? So search advertising, which is extremely profitable. So as soon as we started getting users, as long as our team size was relatively small, it was profitable relatively quickly. And then, you know, the third reason was we made sure we kind of were break even for a long time. And that goes back to kind of me being a bit risk averse, but also I think being profitable really, one, opens up a lot of opportunities. It takes fundraising risk off the table. Could be, kind of clears
6:02 Speaker 02 your mind a bit. So like, people spend a lot of time focused on budgets and fundraising and all these different things. And when you're profitable, especially wildly profitable, you can really focus on what matters more to go after big visions, like product and retention and growth and things like that.
6:16 Harry Stebbings? Absolutely, when you're profitable, but there is another thing when kind of fifty million or so lands in your lap from a big growth fund, which it very much could have done in many junctions in the company's life. Many people always think that kind of growth and capital injection are two levers. Do you think that they're at odds? And how do you think about kind of the relationship between the two? Because most would say, you know, without the capital injection, the growth reduces. How do you think about the kind of the correlation between the two?
6:40 Speaker 02 I mean, at the end, you're talking about converting capital into growth, right? And so you have to be able to spend that capital in some way efficiently, whether that's develop a new product and launch it, hire a bunch of people, or put it into some kind of marketing channel. We were kind of profitable enough where we could grow the team and product investments at different item. We're not constrained by that in terms of that. Potentially, if we could unlock it, you know, find some marketing channels to put a large chunk of capital in. And I'm certainly not opposed to that, but hadn't really found those that required a lot of capital. A lot of the marketing we'd done was less capital intensive.
7:14 Harry Stebbings? Yeah, no, absolutely. And I like a lot of what you've done. Can I ask, in terms of your situation, in terms of your profitability early and having that real mindset, I guess, seeing what we do around us in terms of the funding mayhem of the valley, what do you make of the venture landscape today when you see continuous hundred million rounds, billion dollar valuations for twelve or eighteen month old companies?
7:33 Speaker 02 Well, I generally don't like to generalize because I don't know their situation. And there's a lot of smart people involved in all these things. So I start from the position that there's probably a good reason. And I know one of those reasons is as companies grow, they may be less inclined to IPO. And so a lot of those rounds can be investors and or early employees taking some money off the table. And so that makes total sense. And so part of me thinks when I see a huge round, especially in a company that's making a lot of money, that's part of it.
7:58 Harry Stebbings? Can I ask, does that make total sense? Because a lot of investors that I speak to and a lot of my friends in the investor community are very concerned by the amount of secondaries that we see getting done. Do you think it does make total sense, given that?
8:08 Speaker 02 I think it depends on the person, but from my perspective, I think it definitely makes sense. Because some of these founders and, you know, myself included, have a lot of their net worth tied up into the company. And people are going after big visions, like I'm already twelve years into Ductica, right? And we're just, feels like we're getting started. And it makes sense from a diverse ...point of view to take some money off the table and it's a good deal for the other side because they can get in and see the rest of the growth. And so I think if you have that opportunity, I really personally think that, but maybe that is just me again, coming from a more risk averse attitude, a more kind of financially prudent attitude. But I think if you come from that attitude and you do that, then it kind of opens up your ability to take more risks because you've kind of put aside everything that you wanted to put aside.
8:50 Harry Stebbings? Yeah, no, I couldn't agree more in terms of how it changes the risk aperture. We mentioned the relationship between traction and fundraising now, and obviously you're a master of the term traction, having written the incredible book, Traction, on it. So I do want to dig a little bit deeper on this, Gabe, because traction is often the result of a success in customer acquisition channels of some kind. But today, to be honest, I'm pretty concerned because they're more and more expansive and there's less and less free and open distribution. Are you as concerned as I am by this? Let's start with that.
9:15 Speaker 02 So I guess I'm very generally concerned about the strength of monopolies and especially the digital advertising duopoly on the internet. And so I think there is a need to be extremely concerned there. On marketing in general, it is one, like the book's basic premise is there are on the order of 20 different, just broad, marketing channel categories, not talking about like Google, Facebook, that's just one type of thing, but offline ads, running conferences, engineering is marketing. And oftentimes, the right answer is something more creative and capital efficient, and it requires kind of more creativity in the marketing function. And so I am very concerned as to what's happening in there, but I also think there's still a lot of open space for brand building and marketing in kind of a creative way.
10:00 Harry Stebbings? Can I ask, you mentioned the power of the duopoly, and I was chatting about this the other day with a friend of mine, and he strongly advocated for the breaking up of those powers. I'm intrigued, how do you think about that? And do you think that is the right situation, given their prominence today?
10:13 Speaker 02 I think there needs to be something to be done about the data monopolies that underlie the duopoly. And unless something is done to kind of deconstruct that data monopoly, then this will persist ad infinitum because of the network effects involved. There are many ways to get at that data monopoly, and we've suggested a lot. I think some of the approaches are less thought out than others. We actually spent time, and I personally, drafting a do not traction Legislation last year, and that's an example of what I think is a very simple but effective mechanism to help address the data monopoly issue. And what that is, is in every browser right now, there's generally a do not track setting, but unbeknownst to most people, it pretty much does nothing because it's voluntary and it's putting some teeth to that. So consumers who opt in to
10:55 Speaker 02 this do not track setting would not be allowed to be tracked by third parties as they browse the web. And that would open up this ability for those consumers, and we think it's about 30% of people who opted in here to not be subject to that duopoly and they'd have to be served by contextual advertising. And that opens up advertising market to all sorts of other firms to compete in a contextual advertising market. So I'm hopeful that something like that would help address the underlying data monopolies.
11:19 Harry Stebbings? Can I ask, we've always had incumbents in prior generations of history, be it IBM, be it Nokia. Does the data monopolies here mean these incumbents are so much stronger than before?
11:27 Speaker 02 I think so. The scale of the market and the way that the kind of advertising auctions and data asymmetry is in place is just much stronger than kind of these previous generations.
11:39 Harry Stebbings? Yeah, no, I do agree. In terms of kind of the duopoly, there is kind of a wide variety of channels that people can and do deploy on. In terms of like channel performance, I guess, how do you think about the importance of diversification of channel, especially for you in the early days with DuckDuckGo?
11:53 Speaker 02 So I have a bit of a counterintuitive view here and it's written up in the book you mentioned, but I think when you look back, so for any kind of marketing stage of a company, you're really looking to achieve some kind of growth milestone, right? Be it some kind of number of users or revenue target or something like that, that really is an inflection point for the company. And when you look back at achieving that and like what got you there, it's often one channel really drove the bulk of that. And it just has to do with like effectiveness at any given time. Usually the winning strategy, you often don't have equally effective strategies. It happens, but it's rare. Usually there's a dominant strategy. And so my view is you do experimentation in all these different channels to kind of unlock that dominant strategy. Now to do that, you actually have to run a bunch of experiments. So effectively you're doing a
12:35 Speaker 02 diversification play, but then once you find out what's working, you really double down on that. And to this earlier point about the duopoly, oftentimes that ends up being a creative solution. So even online, you know, there's this Andrew Chen coined this term, I wrote in the book called the law of shitty click throughs. And basically, he's saying that over time, channels saturate and click through rates go down. And when it started, search advertising click through rates were like 30%, and now they're like 1% or 2%. But if you can find kind of new channels when they're first uncovered, and we've done this in our history, like, for example, I was one of the first, if not the first Reddit advertiser back in the day, like click through rates can be through the roof. So if you can kind of uncover that, or even make those happen, you can really be in a place to drive adoption at really cheap rates.
13:17 Harry Stebbings? Can I ask, how do you think about channel mortality? We said there about the diversification, and when one pops, it really pops. But you can't rest on your laurels and sit on it for too long. How do you think about that agility to move between channel in the awareness that channel mortality does happen often sooner than you think?
13:32 Speaker 02 It's constant measurement. Like, you can be looking at the first and second derivative of what you're doing and seeing if it's reaching diminishing returns. And while you're doing that, there's a function, a constant experimentation, to kind of understand what that next channel's gonna be. But what I hesitate to do, or what I advise against, is like really spreading yourself too thin, because when something's working, you really want to optimize it, and you can often get a lot more out of it if you really focus on that. So the way I think of it is, you're doing a lot of experiments upfront to figure out that channel to double down on, then you really focus most of your energy to double down on it, but really paying attention to diminishing returns. And as it starts to diminish, you then switch back more and more to experimenting with new channels.
14:13 Harry Stebbings? Yeah, no, I do totally agree in terms of that willingness to go back to the experimentation phase. We had Josh Buckley on the show from Mino Games, who said on the show that every $5 million you spend, your payback period doubles. Does that align with your experiences? And would you agree with that in terms of the payback period associated with the dollar amount invested?
14:30 Speaker 02 Not as a hard or fast rule, but I think as a general trend, there are different things that saturate channels, right? There are some channels that are way above your scale, and so maybe you could put $100 million into other channels that kind of max out at smaller scales. And we've seen that at our scale now, because we're trying to really get the next wave of tens of millions, or even 100 million consumers to use DuckDuckGo. And so there are not a lot of channels that we can deploy lots of amount of capital into before the price is Start to rise. And so it really depends on kind of like what your goal is and how big that channel is in terms of inventory.
15:02 Harry Stebbings? Totally. And I hope this isn't too personal. I'm really interested though to hear DuckDuckGo is obviously incredibly prominent within maybe slightly more technical crowds and definitely more privacy conscious crowds. How do you think about expanding it to the billion users and the two billion users and those that are completely unaware of technology circles and kind of privacy interests? How do you think about that brain next phase of customer acquisition for you in terms of that next segment?
15:26 Speaker 02 Well, this last couple of years has really been just an explosion of privacy interest following Cambridge Analytica. And so we're seeing 90% plus actual decent education concern rates about basic online privacy things and about 30% in the US and other major markets of people who have actually tried to take some significant action to protect themselves online. Now, often that's an action that may not help them, like using private browsing or do not track. But these are people who are not just say they care, but they're actually acting on privacy. So the market right now is actually pretty large. In that same vein, DuckDuckGo itself has raised its brand awareness to approximately 30% in major markets. And so it's already crossed that chasm point. And now we're really focused on really helping people.
16:08 Speaker 02 Our vision is broad. It's raising standard of trust online. And to do that effectively, we think we need to effectively be the consumer privacy brand. So people, when they want to protect themselves, they turn to DuckDuckGo. And that's what we're focused on.
16:19 Harry Stebbings? Wow, that's some incredible stats. I didn't know that, especially in terms of the progression of consumer education around privacy. I do want to kind of go back to the element of traction there and actually apply it to the element of fundraising, which we said earlier, because you said once that traction trumps everything when it comes to fundraising. What did you mean by this? And how can founders know what the right metrics, I guess, are to shoot for?
16:38 Speaker 02 Metrics depend a bit on what business you're in. But generally, if you have highly engaged users in a business model, you're going to attract investors in some way. And what I meant by that generally traction trumps everything is fundraising, as you know, is kind of believing and telling a narrative, right? Someone's coming to you and they're doing storytelling. And if you have no traction, no numbers to back up what you're doing, it's all storytelling. It's all narrative. On the other end, if you have the most amazing numbers in the world, You can be almost a crappy storyteller and people might piece it together for you and come after you, which is, you know, what you see people going outbound to really go after certain people, even though they might have a lack of storytelling. And so as you get down that traction curve, that's why I mean it trumps everything because you can
17:23 Speaker 02 just be running your own business. And if you have enough traction, you will get fundraising interest.
17:27 Harry Stebbings? Yeah, no, totally. We see it more and more with the larger outbound rounds that I think we're seeing kind of like 70 to 100 million dollar Series As where they maybe haven't raised before, but the traction, obviously the business model works incredibly well. I do want to ask, because with such traction, often the people let product development slip. How do you think about the balance between product dev and a focus on traction?
17:45 Speaker 02 Yeah, I mean, I see as marketing will only get you so far, right? You have to have product market fit underneath that. And so you have to be constantly having a counter metric of retention versus inbound funnel. And if you don't, then you're going to saturate and worse, you're going to churn through all sorts of users and then your growth is going to stall because everyone kind of left. And so you really have to be looking at both.
18:09 Harry Stebbings? Can I ask, what's your guiding metric for success? Is it DAUs?
18:12 Speaker 02 So for a long time, our guiding metric had been just number of searches, that's simple. And it's actually public. We put it at duckto go.com/traffic and you can kind of see our traffic growth over time. As we have expanded in our broader vision of just raising the standard of trust online, we're not just a search engine anymore. We make apps and extensions that really protect your privacy, no matter where you go on the internet. So on mobile, we have a browser, it's a complete browser replacement for Chrome that has tracker blocking in addition to private search, in addition to increased encryption, and then a browser extension on desktop. And so when we think about those, we think of more around MAUs because not everybody searches every day. That said, we're in an interesting position that we can't really track our users. That's our privacy policy. And so we don't have great ways to measure these standard user metrics that other companies do.
18:57 Harry Stebbings? Yeah, it would rather be concerning if you had the most incredible data on all of your users.
19:01 Speaker 02 Yeah, that's true.
19:02 Harry Stebbings? I do want to discuss the company's structure itself, though, because there's a couple of really unique, interesting elements to it. The first is, obviously DuckDuckGo is fully distributed with you all being based out of Philly. I guess what have been your biggest lessons on what it takes to run a truly successful, truly Remote team today.
19:17 Speaker 02 I think the key has been asynchronous communication and keeping everybody on the same page and the processes involved to do that. Now, a lot of those processes get developed as you're a much bigger company and you hear about companies who are fifty to a hundred, a hundred to a hundred and fifty employees, kind of breaking down in communication and having to start all over and develop those bigger company processes. That has to happen way earlier when you're effective distributed companies. So we really started that work when we were only fifteen employees and we've developed those systems over time. But really nailing those, I think, is the key.
19:47 Harry Stebbings? Can I ask, you're at eighty people now. Where were the growing pains in the organization?
19:51 Speaker 02 So a big growing pain was just organizing kind of what everyone is supposed to work on and how to organize that effectively. I think that was probably the biggest growing pain. I think we could have done that from the get go if I knew how to do that better when I started, but we've kind of discovered that over time. But I think once we nailed that and how to get everyone on the same page as to what to work on, it scaled pretty nicely.
20:13 Harry Stebbings? Can I ask, how did you align everyone so nicely across, you know, as I said, a team of eighty now?
20:17 Speaker 02 Well, it sounds simple in retrospect, but it is hard in practice. And what really spurred me in a system I had adopted was a, it's going to answer your question later about what book I like, called The Advantage by Patrick Lee and Sony. And what it is, is it's just running the company on a tight set of objectives. It's a little different than OKRs because they don't have to have metrics associated with it and quarterly or annual kind of reporting, but it's basically staying really focused as to what objectives you're working on and not steering from that and writing those down extremely explicitly. And that's kind of the long and short of it. And there's a lot of stuff to like organize around that and make it all transparent and work in a distributed team, but it's effectively writing down and being very clear at what the objective is.
20:55 Harry Stebbings? Totally. Can I ask, do you have to do that from day one?
20:58 Speaker 02 So we didn't do it from day one, but I think it was a big mistake. I think one should do it from day one.
21:02 Harry Stebbings? Yeah. What would you advise founders, given the mistakes that you've made, given the successes that you've had in the structure and just benefit of hindsight, for those now, a lot of people founders starting out, two people starting thinking, hey, we should build a remote team. What would you advise them?
21:15 Speaker 02 So with a remote team, I would get it all organized. And in particular, it gets really tactical. So I won't go into super detail, but like the long and short of it is put everything in one place that everyone can see. And so it's effectively like if you were in the same room and you had a big whiteboard of all your objectives. Make that a place where everyone can go at all times and that's kind of where they're working on. We use Asana for that. And so there's a big Asana view that everyone lives on called our current objectives. And it lists all of our different objectives that the company is working on very explicitly, all the projects underneath them. And anyone can follow along with any of those projects and each of them has an owner and a role and responsibility for updating the rest of the company. And with those processes in place, it all works very smoothly without having a lot of synchronous meetings.
21:57 Harry Stebbings? Can I ask, one thing that we've found is when you have dual owners on tasks, you see a much lower achievement rate of the task itself. Have you found that? And do you believe solely in the sole task owner perspective?
22:09 Speaker 02 I absolutely do. We kind of stole that concept from Apple, this directly responsible individual. But we have gone into it 100%. So everything has an owner from the top objective down to the little task. And then we have a whole set of company like ours, we're only 80 people, but we're kind of really punching above our wage class with the cards to our employee count. So we have hundreds of different kind of in maintenance mode areas of the company that people need to own. Like if you're a search engine, you know, you have to own maps and news and all these different things. We don't, unlike Google, have a team for all those places. So what we have is what we call areas of responsibility and each one of those has an owner. And so I very much believe in this single owner concept.
22:44 Harry Stebbings? I'm so glad that it's not just me. Speaking of the kind of the structure though, that you applied there with Asana. I am interested because in terms of team structures, it's pretty unconventional in that way too, with no traditional org structure or hierarchy. So why is this? And why do you have that deliberate structure in place?
22:59 Speaker 02 So there's kind of two concepts that explain this. One is called resonant frequency, which is a physics concept that you're probably used to when people sing and glass breaks. What that is, is you're hitting just the right note where the glass is absorbing energy and it gets bigger and bigger in amplitude. Now, hopefully this metaphor falls down because I don't want people to break. But what you want is you want to give people the exact right role where they're so motivated and passionate that they're resonating with it. And if you can do that, people can do amazing things effectively. And teams are even better. If you can get the team organized into resonant frequency, a small team can produce amazing results. And that's kind of what a startup is. But as you get bigger, you want all your teams to be doing that. So what I've found is for that to work,
23:40 Speaker 02 that's really dependent on what objectives you're working on and who's exactly right for the skillset for each objective. And so we want to constantly be moving people around a little fluidly to break down and build up teams so that they can hit resonant frequencies. Now, the flip side of that, the other concept I mentioned is there's a lot of people reasoning people leaves jobs, but two of the biggest are they don't like their manager or they feel stuck in what they're working on. And if you have a hierarchy and kind of a strict set of team and role responsibilities, then you're much more likely to get people stuck in situations where they don't like their manager or they don't like the team that they're working on. Whereas if you can split those leadership roles and responsibilities up, then you can let people kind of move around the company and get the job exactly right so they shine.
24:21 Harry Stebbings? I totally agree with you, especially though in terms of the two reasons people churn. I am really interested in terms of feedback mechanisms. How do you think about creating a culture of accountability, but also without a fear of failure?
24:31 Speaker 02 Well, I think it has to be built right into the values of the company. So the values of our company are build trust, validate direction and question assumptions. And what the latter two really mean is an experimental mindset. And so we just hammer again and again that we really want people to run experiments. And a failed experiment is a good experiment as long as it had a good hypothesis and good data at the end. And in terms of accountability, we don't hold people accountable for results in that way. We hold people accountable for running good experiments, running good projects, running a good postmortem process, which we have for every project. And so I think it goes right into the processes of the company for how you effectuate that.
25:08 Harry Stebbings? Sorry, granular one before the quick fire, but I have to ask it. I'm super nerdy when it comes to postmortems. How do you structure and think about effective postmortem analysis?
25:16 Speaker 02 So first, we have postmortem for every single project, regardless of if it's successful or not. And that means that there's no stigma of having a postmortem. And in fact, postmortems for good projects are often better than bad projects because on a good project, there's no even tension about like blame or anything like that. And people can really open up and say, what could have made this even better? What processes? Change or just in like a better frame of mind. So that's one thing. The second is we have relatively evolved postmortem and other templates that we use and we run that through. So there's like a timeline in the postmortem, what went well, what didn't go well. Action items are kind of the main sections and everybody kind of sticks to the template. And as people are very used to it and they're used to the format, then they're used to really engaging with it over time.
25:58 Harry Stebbings? Yeah, no, totally. I do want to ask one final thing that I am too intrigued by. You mentioned that the structure of the postmortems. In terms of your leadership structure and style, how have you seen yourself evolve and develop as a leader over the last 12 years with DuckDuckGo?
26:10 Speaker 02 Well, as someone who did every single job themselves for the first four years and in the previous company years before that, I obviously had to change from that to being a leader, a manager and a manager of managers and manager of manager of managers. And so obviously that comes with a bunch of different changes. But I think the biggest has been really just a focus on getting the objectives right and communicating them over and over again. And I know people say that all the time in this podcast, but that is really what the job entails as you could figure.
26:39 Harry Stebbings? No, totally. I always say the best CEOs of Paris, they just repeat the same thing. That's probably not the kindest analogy, but I think it's effective. I would love to, to move into the quick fire. So I say a short statement and you hit me with your immediate thoughts. Are you ready to dive in?
26:54 Speaker 02 Sure.
26:54 Harry Stebbings? What's your biggest strength and biggest weakness in company building?
26:58 Speaker 02 So the biggest strength is you've mentioned traction. I wrote another book called Super Thinking that came out last year and it's on mental models. And so mental models are just concepts you can learn in any area. There's tons in economics and physics and startups, you know, MVP is a mental model. But what I learned over time is that if you know all these different concepts from all these different disciplines, you can skip right to kind of higher order strategic thinking and just be a much more effective leader and then in turn company builder. And so the biggest strength is definitely just embracing and trying to learn these mental models.
27:31 Harry Stebbings? And the biggest weakness?
27:34 Speaker 02 In terms of weakness, I mean, I think I've been less excited, I'd say, about dealing with personnel issues. I'm a very intellectual and even keel person and, you know, as you get more and more people, you get more and more drama of one form or another. I'm a very low drama person. And so that's definitely something I've had to learn over time. And I've been lucky to recruit people to work in our kind of people ops department for that as well.
27:58 Harry Stebbings? Totally. And I do not think you are alone as a founder and CEO in that respect. I would love to ask, who was the first check into DuckDuckGo? And how did that come about?
28:07 Speaker 02 I think the first check has to count as my own check for having no salary for four years or so. But I know that's not what you meant. So the first kind of institutional or, you know, angel kind of check was Scott Bannister from Ironport and other fame. And he was just a user and he was following us. And I decided to go think about fundraising and he just reached out and was like, I want to be involved.
28:29 Harry Stebbings? Love it. What a story and what a great investor to get on board. What would you most like to change about tech in the Valley, Gabe? You've got this unique vantage point having not been reliant on venture funding throughout the lifecycle of the company and not being in the Valley yourself. What would you most like to change?
28:42 Speaker 02 I mean, it's what we talked about earlier. There's been a large interest and talk about kind of regulation in tech in the past year. And I really think there needs to be more of a regulatory framework in a lot of areas. But I'm just hoping that we end up doing effective regulation and things like the Do Not Track bill that we drafted last year. And so I'm both hopeful, but also really want to work really hard to make that happen.
29:03 Harry Stebbings? Penultimate one, I always hear not being in a tech hub like Silicon Valley, New York massively hinders your ability to hire the best people. Would you agree?
29:11 Speaker 02 Not if you're a distributed company, for sure. There are tons of people who are great in Philadelphia, which is the fifth or sixth biggest city in the country. So there's tons of amazing tech talent here. But I'd say being distributed trumps that completely because your labor pool is the entire world, which is there are great people literally everywhere. And if you open yourself up to that possibility and are open to thinking about working with people on different time zones and such, you really, really, really open up your talent pool.
29:35 Harry Stebbings? Tell me, final one. What do the next five years hold for you and for DuckDuckGo? Paint that vision for me.
29:40 Speaker 02 Yeah, our vision, like I was really wide, raises Standard of Trust Online and our product vision is privacy simplified. So you're just going to see us doing more of that. And if we're successful, you'll really be able to just look up DuckDuckGo on any device and download our app or extension and be protected. And we would be the consumer privacy brand. I think that's the lagging indicator of our success.
30:00 Harry Stebbings? Well, Gabe, I can't wait to see that happen in the next five years. As I said, I've wanted to see this one for a long time. So thank you so much for joining me today.
30:07 Speaker 02 Thank you.
30:09 Harry Stebbings? I do have to say, I just love the way that he's built the company over the last 12 years. Such an incredible structure and such an incredible leader. And if you'd like to see more from Gabriel, then you can on Twitter at Yegg. That's Y E G G. Likewise, it'd be great to welcome you behind the scenes here. You can do so on Instagram at H Stebbings 1996 with two Bs. I always love to see you there for sure. But before we leave you today, I'm sure you've heard about it, but my word, I just love the Carter product. Carter simplifies how startups and investors manage equity, track cap tables and get valuations. Go to Carter.com/20vc to get 10% off. More than 800,000 employees and shareholders now use Carter to manage hundreds of billions of dollars in equity. And Carter now offers fund admin, so you can see real time data in the Carter platform
30:53 Harry Stebbings? and work with Carter's team of experienced fund accountants. Again, go to Carter.com/20vc to get 10% off. I really do so love that product. But to get a deal done, you really need to build that relationship. And there's nothing like meeting face to face. And there's nothing like Zoom to make that happen. Zoom lets you connect and do business across town or across the world. Zoom ties together all of your communication needs into one easy platform for video conferencing, phone calls, group chat, webinars and your conference rooms. And connect easily from anywhere, your mobile phone, your laptop or conference room. And Zoom is how business gets done. Get your free account at zoom.com today. Meet happy with Zoom. Again, that's another one that I couldn't spend a day without, to be quite honest.
31:36 Harry Stebbings? And as always, I so appreciate all your support and I can't wait to bring you a fantastic episode this coming Monday with Ashton Kutcher.
Previous 20VC: Lessons from 150 Angel Investments into the likes of Carta, Gusto, Airtable and Superhuman, Creating Algorithms and Models For Investing At Seed & Why Younger Investors Have An Advantage When It Comes To Finding Deals Early with Jude Gomila, Angel I Next 20VC: Ashton Kutcher on Early Lessons From Investing in Airbnb and Spotify, Why VC Ownership Requirements Are Becoming More and More Egregious & What Being Good At Product Truly Means Page updated September 29, 2026 · transcript and summary are machine-generated
