20VC: Open Models vs Frontier Models: Who Actually Wins? | The $100,000 Token Budget Every Engineer Will Need | Why Forward-Deployed Engineers Are the Future of Enterprise AI with Clay Bavor, Co-Founder of Sierra

25:03And headcount will be both headcount for salaries and SBC and also tokens associated with headcount. And so here's your salary, here's your token budget, have at it. We're not yet at that point. Our usage compared to some of those larger numbers is modest. And I think the benefit of learning at the fastest rate possible outweighs the capital discipline at this point. We prefer to learn quickly, see what works. It'll be interesting to see how the rate limiter in software development moves around, how the Andy Grove breakfast factory, what is the constraining factor? It used to be writing code. Now it's probably reviewing code.

25:44pretty soon it will be deciding what is worth building and editing kind of what could exist to what should exist. The dynamics there will be interesting.

25:52Clay Bavor:I think the cool question for us to understand if everything is slightly overhyped is what percent of developer salary will be spent on tokens in the future? Mark Benioff, you said larger companies, said that he spends 300 million a year on Anthropic for his dev teams. That works out about 3.8 % of developer salaries. Not actually as much as the headline 300 million makes you feel. If it stays at 3.8%, a lot of the companies that we're investing in and see around us are actually grossly overvalued. If it goes to 20%, they're undervalued. And I had Brandon at McCaw on the show who says he spends more on tokens than he does headcount.

26:28Clay Bavor:Yeah. I think 3.8 % is wildly off from where the steady state will converge. Where do you think it, I'm not going to hold you to it in five years time, but do you see it being a 20 %? Oh, I do. I do. So the 100 grand a year actually will be normalized because you think about a great dev in the valley, I presume$500 ,000 is kind of where they're at. Sure, that would be the upper end. So it feels kind of normal. Yeah. I would not bet on 3.8%. I would bet on much closer to 20%. In software engineering, the gains to me seem unequivocally there. You can debate, is it 2X, 10X, 20X? Even if it's 2X, okay, you've just effectively doubled the size of your engineering team.

27:08That's remarkable.

27:09Clay Bavor:You mentioned the 40 of the Fortune 50 being customers. You use that quite a lot in a lot of your marketing materials. And it strikes me as a very enterprise company. Is it difficult or how do you retain a real product focus, a real closeness to customers when you're so enterprise. Is that difficult? I think it's a little bit of a false choice you're implying there. I think being large enterprise doesn't necessarily mean you need to be distant from your customers. In our case, our customers' customers. So Brett and I are constantly building agents ourselves. One of the more interesting things of the last six months, we released Ghostwriter.

27:51This is an agent for building agents. It's kind of agents all the way down. It's pretty cool. But we are constantly in the products ourselves. And Brett is actually still an extraordinarily capable software engineer. It's remarkable. So some of the code that is in production, he has written. I've probably got a couple lines here or there, but it pales in comparison. And so, of course, we can't on our own simulate the complex multi-system environments that characterize many of our largest enterprise customers. So that, you know, we have to kind of simulate in our heads, but we're in the product.

28:29And then one of the things I think a lot about is we will, in short order, be in a way one of the larger B2C companies. We're doing that via our customers. We're serving hundreds of millions of interactions, right? Soon billions of interactions. So staying close to the end experience there as well, voice fluency, latency, the quality of the experience, all of that stuff is very energizing and things that we're close to. So I don't feel distant from the product, either from our customers' perspective or from their customers' perspective.

29:01Clay Bavor:I always looked at the space itself, and I was like, amazing space, what a huge town, what a problem, and AI perfectly suited for it. And then I kind of peek under the covers, and I'm like, oh, my God, like 15 companies funded with 100 million bucks, Salesforce, Lassie, and Zendesk, all the other incumbents. Oh my god. What is the market maturation of this space? Help me understand how this evolves in a five to 10 year period. Yeah. I think first of all, to state the obvious, the great thing about being in a giant market is it's a giant market. The challenging thing about being in a giant market is it's a giant market and other folks know it too.

29:39And it's startups, it's longstanding companies, it's the incumbents and so your point on it being competitive is certainly right. Five or ten years especially you know in the the age that we're in is a long time. I think what I had point to is amongst the startups customers are voting with their feet. So we are at multiple larger size than one of our next nearest similar vintage startup competitors growing faster as I said are working with many of the great companies in the world.

30:07Clay Bavor:Do you think it's like an Uber lift market or do you think it's an AWS, Google Cloud, Azure market? It's hard to know. I think because the economies of scale in terms of depth and breadth of platform, experience in specific industry verticals and so on, really compounds. My hunch is it will be more like an Uber lift market. And we obviously think we're in the pole position to be the bigger of those two. Again, we sell to some of the biggest enterprises in the world. I had a guest on the show the other day say you can't sell to enterprise without an FDE emotion. Would you agree with that, knowing all that you know now selling to 40 of the 50?

30:43We, I would like to think at least in the AI space, I would say rediscovered and borrowed this model from Palantir. And we came to it almost accidentally. So we started the company and the first thing we did was reach out to people we trusted to understand what are the biggest unsolved problems that you were looking at. And so, oh, interesting, service and support as a foothold into something much broader, helping support customers across the entire lifecycle. We then enlisted half a dozen design partners that we built the first version of our product and platform with and for. And these are, in the history of the company, legendary companies.

31:25Olokai, SiriusXM, Sonos, Weight Watchers. We built the first version of our platform with our engineers deeply embedded inside those companies. So much so that our founding engineer, Mihai, was actually an employee of Weight Watchers, including getting like its performance review time emails and so on. What we realized in that was no one has ever deployed an AI agent. No one has ever put AI in this way in front of their customers. And in order for us to build the best thing as quickly as we and our customers would like, being so close to the business, the mechanics of it, the people, their business model, that we understand it, I won't say as well as our customers, but approaching that, we saw so much power in that.

32:11So starting in early 2024, we really started building out this forward deployed team. Customers use it in widely ranging ways. Our platform is highly extensible and very transparent. You can see exactly how an agent is built. You can export agent definitions and completely build your own. So no need for forward deployed if you don't want it. What we generally find though is in getting started, having Sierra and help from our teams kind of drive while our customer is in the passenger seat, but navigating for the first version. It's what has enabled us to take companies like Next live in six weeks, from kickoff to live behind their phone number and chat in six weeks.

32:53Or Cigna, one of the largest healthcare companies in the world, live in I think it was 58 days. And so time to market, time to impact, time to value, and then the quality of the result, we think it makes a big difference. I wouldn't say it's binary, though, as you framed it. I do think you can sell without a forward deployed team. But I think for getting to the impact of this technology as quickly as possible and at the magnitude that we know is possible, boy, is it an important catalyst.

33:21Clay Bavor:Are we at a unique time in history where for this specific moment in time, every buyer is in the market for the product? Normally, not everyone is in the market for a product at the same time. Every CEO is being told by their board, how are we using AI? Yeah. Is it a unique time because there is buyer pull like never before for this specific moment? There is effectively unbounded demand. And I think in two areas, one, we've talked about coding agents. The other is the space where we're the category leader. One of the reasons we've grown as quickly as we have is to meet that moment and meet that demand.

33:57We're now 100 people here in Europe. We recently acquired a company in Japan, Opera Technologies. You and I were talking about this to hit the ground running there and to have a team that can be attuned to the cultural nuances of Japan. And the concept of omotenashi, which is extreme hospitality, that is what is expected. in Japanese service, and that's what we intend to build there.

34:19Clay Bavor:Starting with the kind of beachhead in customer support and customer service, to scale into the company you want to be, you have to move out of customer support into complete lifecycle management, I guess. Is Sierra a sales platform in the future? Is it a conversion platform? Is it a marketing platform? What is it? I think Rocket is actually a pretty good indicator of the direction that we're headed. You think about the life of a Rocket customer, it begins with search and discovery of a home they might want to buy. We worked with Redfin to rethink their search experience. We help Rocket reach out to folks who've expressed interest in a refinance, make contact that way.

35:01We worked with them to build Rocket Assist to help bring people in and help them shape and size their loan, gather all the information needed, and so on. None of that is service and support. We do do that, right? loan servicing and so on. So I think that's a good example of where things are headed. That's an inbound sales machine. Inbound and outbound. You're right. And it's not just Rocket alone. Next, we work with them on personalized product recommendations. How do you help someone build an outfit, a bigger basket of things they will love? Again, that's much more sales than support.

35:34Clay Bavor:This sounds and feels more like kind of a Fortune 50, Fortune 500 Palantir, but more consumerized, where you're building these kind of amazing solutions for these products to fit their needs. Is that unfair of me? First of all, Palantir is an amazing company. We have taken a lot of inspiration slash copied from them elements of our forward deployed approach. My understanding is Palantir has kind of low hundreds of customers. We are and intend to be at a lot larger scale than that. And I think where that will come from in particular is building real domain expertise in specific industry verticals.

36:11Of course, our first, second, and third customer deployments were by definition unique, one of a kind. I think we've learned some things about how to help build a basket in the retail setting and in some of these other industries, how best to handle a question about the status of a healthcare claim, a healthcare insurance claim, or questions about a fee around a checking account. And so I think we're going to have these deeper and deeper lessons in specific industries and be able to apply those in a much more scaled way.

36:44Clay Bavor:Will you build products that aren't uniformly applicable across customer bases? So if one customer needs specific cart abandonment product features, is that something we build or is it, no, that's not applicable to the platform? One of our approaches in building the company, this kind of goes back to where we started. You can build a platform and hope that people come, The applications get developed on it. Or you can build applications to inform a platform that makes building the third, fourth, and fifth that much easier. And so wherever we can, we're scanning for opportunities to strengthen our platform.

37:19So commonality is much better than something that is truly a one-off. That said, if we're working with a Fortune 50 or Fortune 20 or Fortune 10 or Fortune 5 company, and there is some element of that company that is literally unique, of course, we'll build that. And one of the neat things is it's actually become feasible to build that because of coding agents, because of the pace at which you can move. There's a real unlock there in being able to build a solution on an already deep platform, but extend it in ways that may apply to a single customer. My hunch, though, is that if you build it for one, someone else is going to have that same problem, right?

38:00And so it's less common than you would think. True one-of-ones.

38:02Clay Bavor:I do want to go to the way that you run the company. It was so important in so many of my conversations before this. If we start with the board meetings, I suppose, as I said, many of the investors, every six weeks, not every quarter, can you talk to me about your biggest lessons on how to really get the most out of your board and run the best board meetings? We do a couple of things. You mentioned the six-week cadence. We have kind of a tick-tock, a three-hour meeting and a one-and-a-half-hour meeting. We've done this since the beginning of the company because we could just see if you're on the AI time clock, it moves a lot faster.

38:36Things are changing. Most recently, we came back from winter break and suddenly coding agents were amazing. You had Claude 4.5, Codex 5.2. There is a fundamental step change in the capabilities of these models. It changed our approach to software development. It changed our approach to the core product. And so having a cadence where you can take in information, even from the last six weeks, update your priors, and then change course, I think is quite important. As for running the board meetings themselves, we don't have board decks. We have board memos. So Brett and I write a usually six to 10 page memo.

39:09There's a saying, writing is just thinking on paper. And I think it's very hard to hide from writing. And so getting our thoughts clearly out onto paper, sending that in advance, giving each of our board members some kind of soak time to think through the issues and come prepared rather than be like presented to and managed, I think is a big part of it. And then the contents of the board letters themselves, I think is notable. We've done quite well in our first eight quarters in market. And generally, the format of a board letter is like, we exceeded forecast by a wide margin yet again. Things are going well.

39:43We landed these customers. And here are the seven things we think we could be doing better. Where we're unhappy, we could be going faster here, need to hire in this area, and so on. And then the board meetings kind of take form on their own based on that. You get the scaffolding right. You get the people right. You get kind of setting the table of the big questions we're asking and then genuinely, genuinely inviting our board members in to challenge us and improve and sharpen our thinking. Those are some of the ingredients. I heard that you write also about everything that you suck at.

40:14Clay Bavor:Yeah. What's one of the most memorable writings on what you suck at? One early on was we had such good indicators of the demand we were going to see. and we just didn't hire fast enough to meet that demand. It was like, oh, like we could have taken on this additional set of customers. We had the data in front of us, like we could see it, and we didn't act decisively enough to build out a recruiting team, like scale faster. This was early 2024, so early days in the company. We've since corrected, but that was one that stands out. We are going to go to hiring. You mentioned some of the people around the table.

40:55Clay Bavor:You know, often people say this, but you really can't. You and Brett, I mean, it's the dream team of the best of the best operators. You can choose any investors at almost any price, which is kind of hard. How do you and Brett sit down and discuss price on a new round? Because investors will pay anything to get in. You want it to be high, obviously, but also not too high. How do you actually think about that? Is it like, OK, three years on next year's target? What does it look like? It's generally been inbound is the answer. We think about it, honestly, not in terms of valuation. We think, what is the amount of capital that we need to raise to get to the next unequivocally higher watermark in terms of revenue, company scale, and so on.

41:40So we think of it as milestone to milestone funding. And then we're sensitive, but not maximally so to dilution. And so how do you balance those things? And every one of our rounds, we actually guided to and took

41:53Clay Bavor:a lower price than we could have. I, again, spoke to them. They said about the values within the company, craftsmanship, intensity, and family. Craftsmanship, intensity, and family are three that I wouldn't normally see. Can you talk to me a little bit about why those are so important? I'll start with craftsmanship. Both Brett and I, just because of the way we are, we care about doing things well. If you're going to do something, do it with excellence. Two ways in which doing things with excellence mean much more than just sweating the details. One is what is a great company? A great company is an aggregation of thousands and thousands of things that are themselves great.

42:31It's great people. It's processes that are well designed. It's a great product. It's a great culture. And so how do you build an excellent company? Well, you build everything with excellence. And so I think holding ourselves to the standard, like if it is worth doing, it is worth doing well is one part of that because that adds up to a great company. How else do you get there? The other is you think about what our customers are trusting us with. Back to the trust value, but I'll make the connection with craftsmanship. It is with their most precious asset. It is their customers. How will a company know?

43:04How will a set of people who are considering working with us know how we will show up with their customers? A lot of it is how we show up with them. Sweating the details in how we show up and interact with our customers, the level of professionalism, care, dropping everything when something matters. I'll give you an example there. In our first Black Friday, Cyber Monday with a set of retailers, one of our lead engineers, our head of operations, me or Brett, was in real time personally reading every single conversation that our agents were having. We wanted to make sure we were doing right by our customers.

43:36So that's craftsmanship. And again, adds up to a great company. And it's, I think, very meaningful in helping our customers understand the care we will have for their customers.

43:46Clay Bavor:Intensity and family. Yeah. Can you expand on those? Again, two that I don't often get. So I think it's back to this great thing about Giant Market, Giant Market, hard thing about Giant Market, Giant Market, and others are in it too. I think there is an inevitability to companies interacting with their customers via really sophisticated agents that capture all that they know and all they can do on behalf of their customers and get the job done on their behalf. that handle the complexity as opposed to pointing you to websites and so on where the conversation is the interface, right? I think there's an inevitability to that.

44:21And therefore, in order to win, in order to build the best company in this space, it is about pace. It is about winning. It is about building the best product. It is about being competitive and being intense about it. Knowing that we don't have the luxury of patience, there's nothing written in the wind, right, that any particular company will be the company showing up in our fifth engagement and 500th engagement as intensely as we did our first, like you have to do that. And so I think there's also, I talk about the Venn diagram of who we hire for, smart, nice, intense. And it's hard actually to get all of those three in a single person.

45:00When you do, it's fantastic. You can feel it in the office. And another way of translating intensity is doing things with excellence, doing things with pace relates to craftsmanship as well.

45:12Clay Bavor:Is there anything that you can do or add to an organization to increase or to maintain intensity, be it timelines, be it rewards, incentives? How do you keep intensity with scale? I think it starts with the founders. Like, Brett and I are quite intense. We have to be the pace setters, right? We have to be the examples of intensity. It shows up in how we manage the company. He and I are deep in details, and are constantly, is this good enough? How could this be better? How could we go faster on this? Why can't it happen tomorrow instead of next week? So I think it has to start with the founders as one.

45:48Clay Bavor:How do you determine what you should be in versus what you shouldn't? We've seen the resurgence of founder mode, of founders being in the weeds. It's also not possible in everything, and it's not right in everything. How do you determine that? You have to edit it. You have to have judgment for it. And I think you have to look at what is the thing that is not going to happen or won't happen as quickly without direct applied force from one of us or both of us. And so it's pointless to be in, quote, founder mode, 17 layers in the details and something that doesn't matter. It matters a lot if it's our next generation agent architecture and there's something that we can add.

46:26We try to be selective about where we engage at that level, but it's anything but kind of hands-off management. So I think it starts with the founders. Ambitious goals have a way of becoming self-fulfilling. You set out a goal, whether it's the quality of a product or a revenue number. It's like, well, what would have to be true in order to get there? Like, let's suspend disbelief and just imagine like what would have to be true to cover this much ground this quickly? Why can't we do that? Okay. Why shouldn't we? Japan is an interesting example of that. Why can't we have a giant business in Japan this year and not next year?

47:00What would have to be true? Oh, we would have to have like 10 people on the ground. I was like, why don't we buy a company there? You see how this stuff hangs together. Ambitious goals can take the form of a date. Sure, you know, date driven development can sometimes work. I think also work is like a gas and tends to expand to fill all available space that you give it. And so there's a danger in setting dates as well. It's like, well, we've got this long.

47:22Clay Bavor:It may not need to take that long. It ties to the third one, which is like work expands to the room that you give it. I give everything to my work, and I love that. Third, family as a value? Yeah. I'm just interested by that one. Each of our values comes directly from Brett and me. And actually, one of the best decisions we made was, I think it was the time we were five or six employees. We spent half a day. Brett and I have a technique we call think apart, think together, where we'll initialize on a prompt. And the idea is not to group think one another. So we want to get kind of the best of our independent thinking.

47:55And so we did a think apart, think together on values, went off and spent an hour kind of writing up what our view was, came back and compared notes. And there was, first of all, a shocking amount of overlap, which I guess shouldn't have in retrospect been surprising. It was like we had wanted to work together. We've been friends. I think deeply similar in many of our values, really all of our core values, I would say. Family comes from, I've got four young kids. Brett's got three kids. And I married my high school sweetheart. And I think for both of us, the only thing that's more important than Sierra is our families.

48:31Our belief is that you can be part of something that is growing fast. You can be intense about your work. You can turn on the afterburners when you need. And it doesn't just mean kids. It's picking up your parents at the airport when they get in from out of town. It's going to the friends extended birthday weekend. It's being, yes, at the parent-teacher conference or whatever it is. And I think there is too often an image of kind of a sometimes performative grind in certainly Silicon Valley startups. It's not that we don't believe in hard work, like, boy, do we. Like, again, intensity. But it's in working smart and finding some balance that gives you space for, again, translate family to things that matter to you in the sense of your whole being beyond just work.

49:15Clay Bavor:Are you literally able to work as hard, though, when you have a family and you have four, I mean, Clay, four kids? I find I work a lot. Of course, if you just magically handed me, you know, 15 hours in a week that I, you know, wasn't with kids, probably do something with those. I find I am intensely focused and efficient. And so, like, boy, do I get a lot out of every hour I have. One of the things I've done, I spend a lot of time on 101, going to and from the office. We are all about in-person. And coming out of the pandemic, it was something of a novelty being opinionated about being in person.

49:55So I spend like an hour and a half, sometimes two, on the road every day. I now have a very complex networking setup that combines two cellular networks and a Starlink mini so that I have uninterrupted, beautiful connectivity to and from the city every day. You're efficient. You get everything that you can out of every hour. Why are you so opinionated about in-person? In particular for a young company, I think it is, I won't say impossible, but very challenging to build a culture, a set of shared norms, camaraderie. I think so many of the things we talked about, enterprise software as a team sport, it feels great to be part of an amazing team.

50:33And it's different when your connection to that amazing team is via a Brady bunch of Zoom squares. We have rituals that we've developed that we only would have developed if we were all working in person. I think for younger employees, apprenticeship and mentorship that happens. So much of what I learned and I think the initial conditions of my career were from experienced people taking me under their wing or letting me, in cases, literally look over their shoulder at how they were doing something. I think there's an element of paying it forward that's important and in person has a role to play in that as well.

51:07There's a talk that I love by the renowned computer scientist Richard Hamming, you and your research. For any new graduate, probably the single best thing on a per word basis I think you can read. One of the central theses is find great people, work with them and learn from them. It sounds obvious, but there's something deeply correct. Like how do we learn as human beings? We observe someone doing something and we effectively copy it. So find great people and copy them. That's how you accumulate skills and capabilities. And one of the other points Hamming makes in this talk is knowledge and hard work are like compound interest.

51:44And we all know the earlier you start saving because of the miracle of compounding interest, it can massively change the trajectory of your life. And so any young person should be intensely focused on learning as much as they can as early as they can, locking in those kind of lessons and capabilities, if you will, because it is literally trajectory changing.

52:07Clay Bavor:Do you want to hear two funny things? One, we used to do five shows a week. I just worked harder than anyone else when I was starting out. That's a lot of shows, Harry. Yeah, yeah. It was 11 years ago, but it was five shows a week. And then two, I didn't have 1 ,000 listeners per show for three years. and I never made a dollar on the show for three years. It was never about money or recognition. I only cared, actually, about using this as a method to learn from you. And probably, especially when I was 18, it was harder to meet amazing people. And so I completely agree with those two. There are a lot of young people today.

52:40Clay Bavor:You have kids. I can picture them leaving university who are uncertain about where the world is, what to do. What would you advise them, knowing all that you know? The obvious kind of tsunami coming is AI. Okay, what are the implications on jobs for that? I think there's been a lot of concern, understandably, about, okay, what happens to entry-level jobs? How do you apprentice and so on? I think the unfair advantage that young people have coming out of university is you've just had four years to spend effectively unlimited time. You've got to go to class and pass some exams and stuff. You have huge control over your time and disposable hours.

53:22Coming out of university as a master of these AI tools, boy, let me point you to a thousand companies that would love to have you infuse what you know into how they're doing things. I can't remember a time when a young person with no work experience, but with the right mindset and experience using some of these tools has ever been so valued. Some of our most effective employees at the entire company are 22 or 23 years old and have been completely AI pilled and have a comfort and facility with these tools that many of our more experienced folks don't. Has the way that you hire changed for the profile that wins in this AI-pilled world?

54:05Yes. We completely changed our engineering interview process. So it now looks much more like here's a kind of prompt. Think through an application you would like to build. Cool. Okay, here's$150 to spend on choose your coding agent. You can use whatever setup you want. Use whatever tools you want. Bring your own laptop, bring your own tools. We're going to pay for your tokens. and then build it. Tell us how you went through building it and so on. So at least in engineering, it is an AI native interview. And of course, we test for architecture, systems design, product thinking, culture, smart, nice, intense, the extent to which we think people manifest our values.

54:43But that's changed very significantly. I will be disappointed if in the next no more than two months, not every one of our interviews has some strong AI native component to it.

54:53Clay Bavor:You mentioned architecture there. Do you think we are entering a golden age for cyber and for cybersecurity, given the proliferation of code generated by AI that may not be as secure as it needs to be? In terms of importance, it is obvious to me that it has never been more important, given that the kind of offensive capabilities just ratcheted up five notches. I think cybersecurity seems like a pretty good bet to me. The question is whether the offensive tools turn to be defensive tools, if actually Mythos and Codex 5.5 Cyber, if they themselves are the solution, not a more narrowly focused cybersecurity product.

55:33What was the most recent disagreement you and Brett had? A couple of weeks ago, we were trying to figure out how to get something to move much faster in one space. It's interesting. We basically always converge. It's like we're highly truth-seeking. It's like, what is, we have a funny expression, like, this is correct. Okay, what does that mean? From some objective truth-seeking perspective, like, this is the right way to do it. So we try to get to, okay, what is the correct solution? I was on one side. It was like, I think we need better kind of process and structure around this thing. Brett was on the side of people.

56:10Maybe we need different leaders or a different leader in this space. The answer as with most things, like turned out to be some of both, right? Turned out to be some of both. We started from, no, it can't just be solved. It's like, no, it's not just people. And, you know, we pull on those threads and this wasn't think apart, think together so much as just kind of interrogating each other again, with the goal of just getting to the right and best approach to something.

56:33Clay Bavor:What when Brett says something, are you like, yep, I'm sure he's a G at that? And what when you say something, is Brett like, yep, plays the expert? We think about rather than dividing up the company, we think about majors and minors for every part of the company. So Brett's majors are definitely sales and then engineering. He's really good at selling software. He's really good as a software engineer still. I major in what I've got like the running of the company. So operations, finance, legal, and so on. I do a lot of first calls. He understands our most important contracts for things that are highly consequential on how we run the company.

57:08We have kind of two nuclear keys that we turn on those. Brett, having spent time at Salesforce, really learned from the best. Mark is extraordinary. Is there a seller? He's the best seller I've ever met. Unbelievable. The goat. The goat. Unbelievable. How's the weather, Mark? Have I told you about Agent Force? But honest respect, when it comes to instincts on how to sell, it's like, yep, okay, makes sense. Brett's instinct on system design and architecture are second to none. And so I trust his judgment more than I trust my own. On people stuff, on kind of the building and running of the company, it was like, whatever Clay says, I would go with that.

57:47So I think that's probably the rough yin-yang major-minor split. Dude, I would love to do a quick fly around if it's okay. Yeah, let's do it. What was your biggest lesson from working with Sundar? It's such a gift. Sundar has a remarkable ability to look at a problem from wildly different zoom levels. His dynamic range in thinking is second to none, zoomed all the way out, highest level strategy. How is this going to unfold over the next five years? All the way into the details, the pixels, the drop shadows, the sound, the texture of something. And I have tried to emulate that. Talk about surrounding yourself by great people or having the privilege of working for someone.

58:28I observed a leader who is extraordinarily focused on the product, the work, building something great, also is just a wonderful human being and deeply focused on the humanity and folks around him. What does no one know about Google that you think everyone should know? What people underestimate about Google is when you have the alignment of an ambitious, enduring mission, incredibly smart people, and a culture that values truth and building and service of that mission, that company can kind of solve anything. People sometimes criticize Google for a thousand flowers bloom. If you have smart, well-meaning people caring for every one of those flowerbeds and they're directed in the right way, it is quite a force for invention and discovery and building new things.

59:23Clay Bavor:I got asked to ask you about your book list. I hear you read a lot. That's a shit question. Forgive me for it. What's the must read for me leaving this conversation? Oh. Give me one. David McCullough, The Wright Brothers. It's so good. It's so good. It's a tight history of obviously the invention of the first heavier than air aircraft. And to me, it is as accurate a portrait of entrepreneurship and invention as has been written anywhere. The aircraft could not have existed without this kind of network of pre-existing inventions, most importantly, a lightweight internal combustion engine. And then it was try, it didn't work.

1:00:05Try, it didn't work. There are scenes of them stuck out in North Carolina, being eaten alive by mosquitoes. It's the hardship and then the triumph of having built something that flies.

1:00:16Clay Bavor:I've never said this before in a show, but have you seen a wonderful film called Those Magnificent Men and Their Flying Machines? No. I'm going to send this to you. Oh, okay. Sounds good. It is about the kind of pursuit to fly from mankind. Fantastic. It's amazing. Well, thanks for the tip. It's like the 1940s, 50s. That's great. I'm looking forward to that one. parenting, four kids, and an unbelievable operator and founder. What's your biggest advice? First of all, having kids is the greatest gift. It is such a privilege. And a few things I would say. First of all, you will be a changed and different person, you know, on the other side of holding your son or daughter.

1:00:54It's just, it is the, in my opinion, single fastest rate of change, single biggest change that anyone experiences in their life after they themselves are being born, right? welcoming your first child. I try to carve out time, family dinner. We have many mornings on Sundays, maker mornings with two of my sons, where we block out an hour or two and we build something at home. And so rituals and discipline around making time and space, anything important in life, my view is a product of clear goals and good habits. And so I think if you have a clear goal around how you want to be as a parent and then habits that help you build towards that.

1:01:33I think that's a very important ingredient. And then the other is making kids' interests your own. And so I'm terrible at basketball. My oldest son is an incredible basketball player. I am so proud of him. I go and watch him play and say, he does things like, I could never do that. Not only can't I do that, I could never do that. And so I follow the playoffs. I've learned about the sport. I've learned about the best players. I've learned about coaching so that I can try to enjoy and support him in this interest more fully than I otherwise would be. And so I think for each of our four, it's being aware of what gets the synapses going for them, what they light up about, and then making that interest my own.

1:02:18Clay Bavor:Would you say that's the same for your partner? Do you need to have aligned interests in a partnership, in a marriage, or is it good to have different ones? I mentioned married to my high school sweetheart. We will have been together for almost 30 years and I'm not that old. I think a great marriage is a partnership. And a partnership means you are working in pursuit of and service of some shared set of goals. And so you asked about interests. I think having shared interests in what you are pursuing as a partnership is deeply important. Happy kids who grow into adults who can enjoy their lives and contribute meaningfully to those around them, building a set of values in one's family that are aligned with your own.

1:03:05And then I think ensuring as part of that partnership that the other member in it, themselves, thrives and fully realizes themselves. self. And there are those interests maybe different, but there can be a shared interest in enabling each other to become the best that you're able to become.

1:03:24Clay Bavor:Final one for you, but I do like it. What's the kindest thing that anyone's ever done for you? I feel such gratitude to my parents. I'm sorry if it's a straight down the fairway answer. My father was a career cardiologist. My mom's a very talented quilt maker. Neither of them were in engineering or technology. And they saw that when I got a hold of my first computer, I just lit up. Not really understanding what computers were about. My mom was good with them in the 80s, but it was not at all clear where they would go, but they could see that I was obsessed with them. They supported that interest to the hilt.

1:04:03I remember going with my father and my mom and dad to buy an early Power Mac. And my dad was pushing like, would you be able to do more if we had more memory in it? I think I would be. And it's like, well, we should get more. I was like, is this real life? My mom would take me out of school one day a year and we would go to Ken's house of pancakes, get breakfast. She would make up a doctor's appointment or something for me. And then we'd go to Macworld and I would get to spend the day at Macworld, which for me was like nirvana. And so I feel such gratitude to them and seeing in me that interest and how I lit up about this thing that was unfamiliar to them, but that they then pushed and enabled.

1:04:44And of course, there's a direct line from that to wonderful 18 years at Google starting Sierra and today. They must be very proud of you.

1:04:52Clay Bavor:I think they are. I know that they are. The thing that strikes me from the show is, I don't mean to sycophantically, it's just like what a good person you are. Do you know what I know? I interview a lot of people and they're brilliant and they're intellectually brilliant. You obviously are that. It looks like what a genuinely good person you are, which is really, it's very tangible. So I really can't thank you enough for doing this. And you've been an incredible guest. Thank you so much, Harry. I really appreciate it. But before we leave you today, a quick shout out to a company I've been genuinely blown away by and have been tracking closely, ROX.

1:05:26Clay Bavor:I've been watching this team closely and the speed they're operating at and the level of applied AI talent they've assembled, it's honestly remarkable. ROX is pioneering revenue agents for the global 2000, plugged into your data warehouse and CRM, and delivering board-level ROI in just 90 days. These sales and revenue agents handle the end-to-end sales process for large enterprises, from research prep to deal risk, outreach, and opportunity management, so sellers spend more time with customers and less time in tools. This isn't another productivity app. Christ, we've all had enough of those. Rocks gives reps a single interface on top of their GTM stack, powered by a knowledge graph across your internal and external data.

1:06:07Clay Bavor:So if you want to boost AE productivity, increase revenue per rep, and consolidate your stack, try Rocks at rocks.com slash sign up. While Rocks runs your sales pipeline, Framer runs your website. A website should help your business grow, not slow it down. If updates to your.com feel harder than they should, Framer is the shortcut you've been looking for. Framer is an enterprise-grade, no-code website builder that works like your team's favorite design tool, and it's used by companies like Perplexity, Miro, Mixpanel to move faster. Designers and marketers can fully own the site with real-time collaboration, a robust CMS built for SEO, and advanced analytics that include integrated A-B testing, so you're not just shipping pages, but you're maximizing what works.

1:06:53Clay Bavor:And when you're ready to ship, changes go live in seconds with one click. Publish. Without relying on engineering. Plus, Framer is built for scale. With premium hosting, enterprise-grade security, and 99.99 % uptime SLAs. Whether you want to launch a new site, test a few landing pages, or migrateyourfull.com, Framer has programs for startups, scale-ups, and large enterprises to make going from idea to live site fast. Learn how you can get more out of your.com from a Framer specialist, or get started building for free today at framer.com slash 20VC for 30 % off. 30 % off a Framer Pro annual plan.

1:07:34Clay Bavor:That's framer.com slash 20VC for 30 % off. Framer.com slash 20VC. Rules and restrictions may apply. While Framer helps your website convert, Superhuman Go helps your inbox move faster. I do this show three times a week. That means three sets of research, three sets of prep, three sets of follow-up, and about 400 other things in between. My inbox doesn't sleep, and neither do I really, which shows in my wrinkled face. But I was juggling a dozen tabs just to keep up. Another window, copy this, paste that, lose your place entirely. That is why I started using Superhuman Go. It's an AI chat that's always there when you need it.

1:08:14Clay Bavor:Already up to speed on what I am doing. Last Tuesday, two minutes before I went live, I had a 40 message thread. I hadn't read. I asked Go to summarize it right there in my inbox. No new tab, no switching apps. From the makers of Grammarly, Superhuman Go works inside the tools and sites you already use. Your browser, your inbox, your docs. It handles the repetitive stuff so you can focus on the work only you can do. AI that works with you, not on top of you. Superhuman Go keeps up so you can move forward. Find out more at superhuman.com