Wesley Chan on Building 100-Year Companies and Investing Against Consensus

0:00AI legal companies, how the hell do you know what you're going to win? You know, what if OpenAI launches it tomorrow? They have every incentive to go like build it and launch it. I was looking, they just posted a stink for an AI engineer for legal. I was like, huh, like, you know, if I were Harvey or Lagora or one of these companies and, you know, they're hiring one, they're probably gonna hire 20 quietly, right?

0:19Peter High: I'd be worried. Welcome to TechnoVenture. I'm Peter High, president of Metastrategy. My guest today is Wesley Chan. Wesley is the co-founder and managing partner of FPV Ventures, an early-stage venture capital firm focused on backing mission-driven founders, building the next generation of transformative technology companies. Since its founding in 2022, FPV has grown to manage more than a billion dollars in assets, investing in the earliest stages of companies spanning enterprise software, AI, healthcare, and infrastructure. Prior to FPV, Wesley spent 14 years at Google, where he founded Google Analytics and Google Voice, helping build Google's early advertising platform, and later became one of the founding general partners of Google Ventures.

0:58Peter High: He subsequently joined Felicis Ventures, where he established one of the industry's strongest investment track records. Across his investing career, Wesley has backed numerous unicorns and five companies valued at over$10 billion. He's been on the Forbes Midas list of the best venture capitalists multiple times and is at number 54 in the 2026 list. In today's conversation, we'll discuss what Wesley's learned from building products at Google and investing in some of the most successful startups of the past two decades, what he looks for in exceptional founders, how AI is reshaping the next generation of enterprise companies, and where he believes the greatest opportunities for innovation lie in the years ahead.

1:34Peter High: Wesley, welcome to TechnoVenture. It's great to speak with you today. Great to be here. Yeah, it's a pleasure. I'm looking forward to our conversation. And I wanted to begin, if you don't mind, with some questions about your experience at Google. You built early versions of Google Analytics and Google Voice. You worked on Google's early ad systems. These are very interesting, informative, both experiences for you, but remarkably important products for them as well. And I wonder, as a result of that experience, what did you learn about making products that stick with users that I'm sure you're now leveraging as you contemplate the same for the companies you're investing in?

2:15Yeah, you know, I think Google was a fascinating place because nobody thought it would work. you know it's the the the history has proven otherwise but back then we were all sitting there going like well there's a dot-com crash going on uh everybody is getting laid off left and right i still remember going through six roommates in a year because everybody's working for a different dot-com and the u-haul truck would come pull up and they're like yeah i'm sorry i have to like kind of like back out of my lease uh you're me sorry and they'd pull up their um u-haul and move all their stuff back to ohio and they'll live with their parents because they're like company imploded, right?

2:47I had plenty of friends that got screwed by having worthless stock options. Not only were they worthless, they had like exercise them early, but then pay the tax on them. And then they had a huge tax bill due on worthless options because there was a massive valuation increase that they got. And so I was watching all those records sort of happen. I don't live in San Francisco anymore, but during the heyday of after the dot-com crash, when things recovered, like it would take two hours to get up from Mountain View to the city on the 101. And, you know, back then I could, there was zero traffic. It was like, kind of like a ghost town, right?

3:20You could drive up the city in 21 minutes versus two hours. But, you know, back to your question about, about Google in the early days and the products, there was just something special about Google. And I think it was both of act and time, right? When the dot-com crash happens, all the best talent concentrates in one place because Google was one of the few companies that succeeded. So I got the work of some of the world's best talent, Bill Campbell, John Doerr, Larry and Sergey, Susan Wojcicki, who, you know, ran YouTube for a while, one of the most like thoughtful product managers, Marissa Meyer, Brett Taylor, who was the, you know, co-CEO of Salesforce was my office mate, right?

3:52And so you got this like amazing, you know, gathering of some of the world's most thoughtful, most smart, most brilliant, you know, most Steve Jobs-like talent for product. And then the second piece was that, you know, Google had an uncommon insight that everybody scratched their head on and said, like, it won't work. If you think about what happened with Google, when it started during the dot-com boom, there were 20-plus competitors all building search engines. Everyone monetized on display ads, right? Like you'd go load up Yahoo and there'd be a punch-to-monkey ad that would pop up behind, and it was all these display ads.

4:22And so consequently, Yahoo had Terry Summel, who was the CEO. He was a Sony Pictures CEO before, right? He was like a media guy. And guess what? He started turning Yahoo into a media company. He wound up saying, we're going to go and optimize for making revenue. And what's the incentive structure? go keep you there as long as humanly possible. He would tempt you to go sign up for fantasy football, get a horoscope and see the weather while you were trying to get a search about a restaurant hours or for a digital camera, right? That was the whole portal play. And so like, you know, you'd try to sit there and like, oh, I want to go look up one of your books or I want to look up your bio, your background.

4:57I want to look at the hours for a restaurant. I want to go look up, you know, a digital camera view. And then you get like served a massive like upsell to get a horoscope. and then like play fantasy football. It's not what you wanted. And Google said, I'm going to get you off quickly in 10 seconds and two clicks. That was so unique. It was so heretical. It was so crazy. Like people said, how do you make money? And Larry and Sergey would just strung and go, we didn't figure that out yet. But we think people are going to stay because like, you know, if we get them off in 10 seconds and do clicks, it was fundamentally better than anything else they'd experienced.

5:24No fantasy football while you did a search. And I only tell this like sort of context because it was heretical. Nobody knew how to make money. People thought it would fail. And because they created a better user experience because they were zigging when everybody else was zagging. When everybody was upselling you on ads and portals and punch the monkey ads, they said, we're going to go and create AdWords, which was part of the search results, right? It looked like it was functionally searched results, and the results were relevant. And they created this massively fast search engine that wound up winning, right?

5:52They optimized for latency. They track how fast the Apple would load up, and it's like, oh, okay, great. They're still serving fantasy football. They're like 10 minutes and 20 clicks, and here it's Google in 10 seconds and two clicks, in it wound up winning the market. And when you work with people who have that unique insight, who said like, this is a hundred year plan, this is the right move. I don't care what the rest of the world thinks. Like you kind of, you kind of like, you know, sort of see this excellence and you see this sort of ability to really buck the trend and be lonely and be right.

6:18And when that happens, like you get like, you know, the one winner that winds up changing the world. And so I got to see that upfront. I got to be there early. I got to be there when everybody was, else was like, Oh, why can't we just sort of display eyes on Google? I got to work on the Google Adboard system, which actually had a relevancy metric. Larry would not allow it on Google unless it was faster than the search results and was more relevant than the search results. If the ads were more relevant, you can click them and go to the search results, right? So we had to make ads and we had to make an engine that wound up being more relevant.

6:46It was information you wanted. We weren't serving you a Ford F-150 pickup truck ad on a digital camera review with a digital camera ad, right? And that wound up putting the market. And I think somebody told me, it's like, Wes, you were instrumental in helping to create one of the most lucrative inventions of the history internet not many people didn't lay the flame to that so that was my early days and i got to see that up front and boy what a what a what a crazy what a crazy sort of like um journey it was fascinating what a talent factory it was as well present

7:13Peter High: company included i want to actually before we leave that period uh i also want to ask you about you were the chief of staff to sergey brin so i got drafted as a part-time job i remember uh john door walking my office going with bill campbell uh you know two silicon valley legends i didn't know who they were back then, right? I got at school. And they're like, you know, Sergey likes you a lot. I'm like, oh, that's great. The co-founder of the company, he thinks I'm good. He's like, well, he'd like you to be his chief of staff. I'm like, well, I'm already helping to build the ad system. I'm an engineer and I'm a product person.

7:40I have six jobs. I'm working on Google toolbar and I'm working on analytics and all these other things. They're like, you know, this isn't a request, man. Like, you know, he wants you as his part-time chief of staff. It's only going to be a year, like, but he needs some extra help. And I'm kind of sitting there going, like what you're adding more stuff to my plate like when you already asked me to go do the I wound up doing it for six years uh I had to find him a replacement he was never happy with any replacement I found so until I found him and he should tell who was you know well actually is another like fantastic partner that was a highland capital like I was stuck doing that for six years and I had to do it part-time so I do the board decks and everything else I hated it because I thought I was like oh great I'm like a glorified assistant and it turned out to be the load-bearing fantastic part of my career because I got to see how to scale you know what is an iconic company and I wound up changing the world like close up front.

8:24So yes, I got to see that very closely, even though it was kind of like against my will at the beginning.

8:30Peter High: In 09, corporate venture was still a relatively new model and Google Ventures was established. You got involved with that. The founding partners were really fun. Amazing, yeah. Talk a bit about the genesis of that, given the newness of the idea. Yeah, so I had spent almost a decade at Google, right? When Google Ventures started and it was a complete accident. I had gone to Larry and Sergey and I was like, look, I really enjoyed working with you. Thank you for the opportunity. This company has been very generous, but it was like, you know, hundreds of people when I started, when I was thinking about leaving in 2009, it was like 80 ,000 people, right?

9:05Or some ridiculous number. And I was like, I don't know anyone at the lunch line anymore. Like I can't get anything launched. You have four lawyers following me around on Google Voice thinking I'm going to go like cause antitrust problems, right? And, you know, I said, I'm going to go do a startup. Like I want to put my name on the door and build this. And they sort of said like, Like, look, we're excited for you. We'd probably back you, but like, you don't want to get toilet paper. Like you don't want to be buying toilet paper or picking health insurance plans. Like, you know, come stay at Google.

9:28I'm like, well, that's so nice, but there's 80 ,000 people here. And he said, no, we're going to start this thing called Google Ventures. It's a corporate venture capital fund. And I was like, I don't want anything to do with this, right? Like if you think about corporate venture capital funds, it was like starting another search engine. When Google started, there were 20 other, you know, 50 other ones. Like Intel had one, Qualcomm had one. None of them succeeded. They were all terrible. And no offense to the people that started those, but there's always a misaligned incentive in corporate venture capital.

9:52What you wind up doing is that you have a great intention to start this fund. One of three different things happened. I did a deep and deep study of corporate venture capital before we started GP. The first was that you have great intentions, you set up a wonderful fund, and then what winds up happening is the people do too well, and then they get paid more than the CEO. So people complain, the CFO gets, they shouldn't be paid more than me. And then they get rid of the carrier, the financial incentive, and then they pay everybody bonuses and all the great people leave. This just happened to Microsoft Ventures.

10:22It happened to Qualcomm Ventures. Like Intel Ventures have the same problem. Everybody has this problem where like eventually like, you know, you sit there and go like, oh, they should be paid more than the C team, right? And then, you know, all the good people go, you know, if you're good at what you do, you want to be paid well. The second thing that happens is that, you know, some bad thing happens to the company, layoffs, a bunch of other things. And then the corporate venture capital group looks like a luxury good, right? You get rid of the luxury goods when you have to tighten belts. And so first thing that gets cut, your corporate venture team, what do we need to be investing in companies?

10:47We can't even invest in our own people, right? So they cut that. And then you get rid of all the good people. You want to be investing when times are tough. You don't want to be cutting, right? That's the whole thing about venture capital. My career was made in 2009 after the financial crisis. And because I started then, it was the biggest piece of luck that I ever had was that half a venture got wiped out in the financial crisis. And GV comes along with a billion dollars worth of cash over 10 years. And why not? The third piece that winds up happening is that eventually the company goes, oh, you're investing in competitors.

11:12You wind up killing a lot of great deals. And then founders learn that, oh, the interests of the company, my interests aren't aligned. Oh, I have to go use Microsoft Azure, for example. That wasn't what happened. But they both said, you have to use our infrastructure. Use our products. Or if you don't use our products, then we'll pull our money and make your life miserable. And eventually every founder says, screw those guys. like you know they're making me do something unnatural of my company that's not aligned with what i want to go do for their benefit i'm i regret taking their money you never want a founder said leaving and say i regret taking their money so that happened google ventures was financially independent it was carry based it was it was set aside from from from google right like it was independent it was kind of a quasi-independent unit we were allowed to invest in competitor company we invested in six companies i invested in optimizely which was a competitor to the business i started right like at google analytics ran up google website optimizer which was like exactly the identical product and the people that started that product like were former apms at google that i knew really well and i helped back them along with peter fenton right like it was kind of like crazy that i invested in a competitor product and you know my old team was so mad at me and i'm like like that's what we do we find the best people and you guys kind of like build the best product here very few corporate entity allow you to do that in google ventures that's why it's durable right like we set these first principles and they're still true to this day so you have to give credit to larry and sergey give credit to john and mike maritz we were lucky to have those two guys on our board, the two of the most best venture capitalists in the history of this business.

12:34And they saw the long-term game and they said, like, we support that idea. And I was very lucky to be given that opportunity, not knowing anything about VC. And that's kind of what Google did was we didn't know anything about search. And we like wound up creating a great search engine. We didn't know anything about Gmail or email. We wound up creating, you know, Gmail, right? Like, you know, same analytics, you know, same with, sometimes when you have smart people who like get a fresh view of it and you understand the structural failures of why the incentives are misaligned, And then you go create something where you align the incentives.

12:58And then if it works out, it becomes durable. And that was very lucky that I got. But I had no interest in doing venture capital. I was an engineer and a product builder. And I still miss those days. But now this is my 17th year doing it. So I don't quite suck at it as much as I thought I would.

13:12Peter High: Well, I want to talk a little bit about the interregnum between your current post and your one with Google Ventures. That was with Felicis Ventures. And I wonder why take the leap from Google to Inferm? Oh, yeah. You had a little time off between the two, if I recall. Yeah, no, it was wonderful to have the time off. Look, if you look at my arc, I always move when things get big, right? When AdWords got big, it was like 40 people when we were working on it. Then it became 4 ,000 people. It was like, time for me to go to do a new thing. So I started Google Analytics, right? Which wound up being something nobody wanted.

13:46People hated me so much. They called it Wesley's Folly at Google, right? Like, you know, I had to go buy a company called Urchin to go get Google Analytics, to sneak it under the rug into Google, right? And I wound up doing that. Now everybody uses it. But like back then, everybody thought I was crazy for wanting to go expose how bad the ad system was. So I'm like, I kind of worked on it. I know. And I said, why wouldn't we want to know before our customers find out? And, you know, Larry and Sergey about the point, but a lot of our salespeople hated it, right? At the start, they love it now. and then um so i started that and that was urchin was i think when i bought the company it was 12 people that helped me build the first version a couple versions of google analytics now it's like you know hundreds if not thousands of people right so i was like great you don't need me anymore it's time for me to go start something else started google voice bought grand central right the creed walker and vincent piquet that was like a 15 person startup we helped build google voice we helped build you know part of android like it was one of those things where like you know we built the carrier system google fi was built on top of it now then it became like thousands of people.

14:42I'm like, Craig, you should run this now. Even he got frustrated with how big the team became and it wound up starting Dialpad, which is a billion dollar company now, something I invested into Google Ventures. The same thing with GV, it got big. I love them. It was 100 million a year. Then when I left, it was billions a year. I said, it's time for me to move on. I started hitting upwards of 50 plus partners and it was in the founding year, GV. Felicia also had a growth spurt. I'm very excited to be there. I learned a lot. When it when it grew to a certain size, I was trying to go back to my roots and go do something where I can, you know, it's the Navy SEAL function, right?

15:17That's where I do my best work. And so FPV is going to be the same size and be like benchmarks. Like we're going to keep it like, you know, unique and tight. We're going to invest in founders, core family. And, you know, I want to, I don't want to build a team that's larger than I can feed with two pizzas with Chef Bezos, like kind of famously said is like the optimal size, right? That's where I do my best work. You get trust, you get people who have each other's back. Everybody like kind of knows that you're we're watching each other so we push each other further it's like a you know it's like it's like it's like a like a championship you know sports teams like the knicks right like they push each other forward rather than sit there and like have swim lane to go like oh you got my swim lane i'm gonna like sabotage you right and that happens at some other venture funds and that's not what i wanted to build so i if you see this in my arc it's it's it's explanation now that my name is on the door with pega who's my wonderful business partner we both see eye to eye like we don't want big teams i mean she grew morgan stanley she was only female in her analyst class that she started after leaving MIT to like make it to the C-suite at Morgan Stanley.

16:10She worked at a big company. You know, it's not something we enjoy. So we want, we want a small team where like we get to do our best work and it's probably the last chapter of our life. So our name's on the door. So we can choose not to let it big versus other things where we don't like control it and it grows big. And it's a, we call it the curse of success and we get to manage that curse now ourselves.

16:28Peter High: Wesley, FPV stands for first principle ventures. I wonder if you could talk a little bit about how the firm differentiates itself. The joke is that we're FPV, right? FPV is what you need Pega and me to be for you in that moment, right? If you need to be a fail-proof, if you need us to be fail-proof ventures because you took our money and we won't let you fail, we're going to do that, right? If you want us to make sure we understand your point of view, it can be founder's point of view. A lot of our founders say, oh, look, you guys are first principle ventures. When everybody was leaning into AI, we did a lot of life science deals in our first funnel.

16:58We backed Invada. We backed Strand Therapeutics, which actually has a near cure for metastatic melanoma. right? People are reversing their cancer in when they're in hospice is kind of nuts, right? And, you know, their clinical trials have started having, having early, early data points on this. And then you're just watching people like get up from being like deathly ill. It's kind of crazy, right? And, you know, it turns out when you, when you have a, when you have a, when you have a, a load bearing drug that's curing cancer, it's highly valuable. And the company becomes worth hopefully tens of billions of dollars.

17:27So we're leaning heavily into that. And I've been doing since my GB day. So I, I know how to spot great, you know, life science companies. So first principles, most people that don't have first principles chase memetic companies, they go do like, Oh, this is the 15th legal company, AI legal company, why don't we do 16? Because like, it's a hot space. And I'm like, well, and 16 companies in the space, not monopoly, right? Very hard for the, you know, it's hard enough to pick a one horse company to win. If you have 16 horses in a race, which one's going to win? It's time. And sometimes it's not the one with the most money, right?

17:53We've seen that, that chapter play out. So we, we, we have first principles. So it's mind my team that matters the most is like, look, you know, when shit hits the fan, we want to be the founder's first phone call. We don't have to be the absolutely first one, but we will be one of their first phone calls. We have to have that trust. If we're not first phone call, they won't tell other founders that we did a great job for them. I won't win new deals. We'll screw up the flywheel. And I'm not doing it to be transactional. I'm doing it because I generally care about their success. But, you know, we have to be their first phone call.

18:19So we say it's first phone call ventures too. So, you know, it's what you need us to be. Luckily, we picked three letters with a lot lot of possibilities. And I picked a space where there's lots of great possibilities too. So that's sort of the reason why we called it FPV. But yeah, if you need to be what you just told me, I don't know. That's a new one. I don't think I've ever called it that one before, but I'll write it down.

18:38Peter High: I better know where I found that then. But thank you for describing the variety of what it stands for. That's really great. You've mentioned that you, the Firmback's mission-driven founders with a hundred year vision. And I'd love to have you kind of describe that at a time where the pace of change is so dramatic, where companies are scaling up so quickly. And some of them, I'm sure you find have more of a short-term perspective in mind. Talk a bit about what differentiates those people with a hundred year vision. And not everybody has a hundred year vision. I can't say every one of my companies has one, but that's what we look for.

19:10I mean, the most obvious example was Google, right? You walked in and Larry and Sergey knew what, like the company they have today still fits the vision that they had when I started there, you know, back in the early 2000, right? They said, we're going to have things that know what you want before. We're going to have a search engine. It's not just a search engine. It's going to be anything. The mission statement of Google is organize the world's information, make it universally accessible. Gemini, YouTube, all fit in that mission. They were all pieces going like, oh, we need to like start delivering content to people.

19:37I'm like, we're not a content company. He's like, well, we can be. And then we bought YouTube, right? Which I helped with, you know, on the acquisition team for that on the ad side. I was sitting there going like, this is so confusing. But like, you know, it's part of Larry and Sergey's vision and a hundred year plan. And I don't think they specifically had any idea that AI was going to come, but like, you know, they wanted to go build the Google brain. Sergey's been talking about it since Google day one, right? And then the self-driving cars, how did a hundred year vision? Like Sergey's like, this is part of the world's information.

20:03You can't build self-driving cars. It's about understanding what maps look like, what people look like with like, you know, predicting whether somebody's crossing the street. And this becomes mission critical, right? You know, in terms of like life and death, to like get people safely to where they want without killing anybody or killing or hurting or maiming or whatever in between. And Waymo was all a part of that vision. That's a hundred year plan. Like, you know, it's like things, they sat there and said, I want this company to survive and thrive past my lifetime. You don't find too many founders that say that they're worried about like, you know, raising the next round, right?

20:30They're worried about like whether they go from C to series A and you have Larry and Sergio and we don't care. Our vision is big enough. If we like to pull off, even a part of it is highly valuable. And then like we, you know, people believe in that path and like, you know, it's going to be one of the most valuable companies as a side effect, not because we seek to build it out came true right like it is one of the world's most valuable company i'm still very happy i own shares of that company to this day right that i you know about when i was an early employee um canva another one right 111 people said no it's a print shop we don't get what you're doing and they said we just want to make you think about a design and it appears we are not there yet we're not even close right like it was a people thought it was a print shop when it started right you made business cards and you made like invitations to birthday parties and now today It's got the third most used AI in the world, which is crazy, right?

21:17Nobody thinks of Canva as an AI company, but they're the third most used AI in this world as of today. More people use it than DeepSeek. More people use it than Anthropic. The only people that have more distribution than Canva is OpenAI and Google, right? Because those guys have distribution. And if you think about it, it's true. They have a safe AI, right? Kids are using it to do their homework. The AI is specifically tuned to give you wonderful PowerPoint decks and better images and to edit and clean things up. that's not there to teach you how to like commit suicide or like build firearms right like you can't do that like their llm is not not not not um not wide enough to like sort of like you know do some of these general use cases that like people where people can hurt themselves and so like there's this trust that every parent has on canvas ai that kids are using it and none of them are using it for none of them can use it to like you know create porn right so like it is they have distribution and they have an ai that's pretty good they have an ai that doesn't burn many tokens because it's so massively efficient.

22:08A lot of it happens on the computer itself rather than having to farm things out of the GPUs. And then if you have a complicated deck or you have some homework that needs a lot of help and you want the AI, then you can pay extra for the tokens to go do it, right? But think about that, right? They moved out this AI and like thinking about design, having it appear. It was the same thing that Larry and Sergey said. You should think about your search results or think about the digital camera view or think about the video you want to go see. Well, make sure you find it or create it for you. And that part of the creating for you didn't exist when it wasn't even close.

22:35Nobody knew how to do it, nor do we have the compute power to do it back then. And same thing with Canvas. When you hear that 100-year plan and that clarity, you need those two things as a 100-year plan, plus you need clarity. They showed me their 100-year plan on a pirate's map, everybody using Canvas, everybody thinking about design, magically appearing, and then nobody else can catch up. That was their whole vision. And I said yes, 111 people said no, right, at the series.

22:55Peter High: Yeah, so talk a bit more about why it appealed to you and it didn't do 111 investors beforehand. Yeah, because everybody was indexing on memetic things, right? Oh, what's their pedigree? Oh, they're in Australia. all their like they were romantically involved couple that wound up becoming husband and wife right like those are all negative signals and then you know they had 14 monthly churn and the first version of canva had no monetization so you're taking a bet on something that like you know looked like a failure at that moment to most investors mel had a spreadsheet of the 111 people that said no to her a lot of them were like oh you're not in sultan valley oh your pedigree didn't look great they were they were they were high school sweethearts they met at as history teachers right at like you know at some at us at their at the at the secondary school they were teaching in in australia like that's not a pedigree where like it looks like four people from open ai or google or facebook or whatever the heck that people were nixing on back in that time right and then you had this thing that looked like a print shop oh that's cute but like we're not backing a business card print you know design software right and that that was not what they want that that's that part of what they started out with but that wasn't what they what they wound up building and they had this vision no one would listen to them on that you have to go to all the way to australia to hear it so there's another barrier to entry so a lot of people saw it and said no and then you know i i wound up like wow they kind of remind me of like the australian married couple version of Larry and Sergey.

24:04Why not? Right. And, uh, you know, we, I was very fortunate to be able to, to underwrite that, uh, series a. So, uh, and, uh, you know, it's been fun watching their journey. I've been working with them since 2014, right. When they first started the company and it's just amazing to watch that vision play out. Nothing that she's doing today was not everything she's doing today was, was part of something that she had in her mind when she started Camden, when Mel and Cliff started Camden. So that's the incredible thing. Just like how gmail and some of the ai stuff and some of the gemini stuff and the banana nano banana thing that like you they see launched were all part of sergey's vision of like just you want something it appears on the screen for you as you think about it you still and he's mad that you still have to type it in or yell at it in your phone to get it right like you know it should you know

24:48Peter High: you'd have a brain implant if he could have that but you know that's a little bit yeah it's fascinating you were uh early money if not first money into uh robin hood plaid flex they all got they all crazy ideas right like you know i was like payroll but like you know it sucks i was like what do you mean it sucks like you know isn't like whatever have you tried it so i wouldn't try to i'm like oh yeah you weren't kidding adb is not great sorry adb um and and i'm like wait i have to it takes this long to add somebody and i think i go like you know do run the i9 myself they're like we should just add somebody by like thinking of it and like well you know give me your social number i'll go find all the stuff and like make it easy to add and by the way we're not in charge you 25 a month we're gonna charge you four and i was like so wait you're telling me it's going to be 10x as cheap 10x as good and you're going to like handle everybody's health insurance and all the things i did not want to do when i was telling sergey i was gonna like leave google in 2009 and it was like okay well you know why not take a bet worked out i mean you just you you all most vcs say oh let me go poke at all the ideas that you're wrong we're we're trained to do this right like oh like somebody tells you something they say it can't work the adult thing to do is like go like pick it apart and go like oh here's all the load-bearing pieces of why it will fail and i'm just like a little kid.

25:59I'm just like, what if it goes right? Yeah. That's super interesting. All you have to do is imagine if it goes right. And if you say yes to the company where it actually goes right, you go on the Midas list. It's kind of crazy. Think about that. Most people don't do that. They sit there and go, I have to play the politics. They ask these non-load bearing questions that wind up being how I get the deal through versus whether it's a great deal for me to spend time on. You only have so much time on this planet. So everybody asks the question, oh, can I get it through my partnership? Well, I look good doing it.

26:25Well, it looks like my LPs like it. These are all the questions they ask. And I ask the opposite question. Is it, what if it goes right? I don't care what my LPs think. I don't, as long as it does, I don't hurt the world, right? We don't do anything with guns. Like most of our LPs are children's hospitals and charitable institutions, if not almost all of the money, right? Like I wanted to, because our fund size is a constraint because we're not raising, you know, tens of billions of dollars. We have a benchmark size fund, or at least what old benchmark was at the beginning. Like we can afford to do the best companies and we can afford to, because my track record of like investing in Canada is very fortunate.

26:53I can afford to pick the best LPs. So we pick only children's hospitals or charitable institutions as our LP based and people that are mission driven. Right. So first of all, if you have children's hospital money, you can't go bring them a weapons company or tobacco company or a gambling company like people. And they call it whatever they call it. Like we don't bring those companies. I'm not going to go do something where you can go like bet on the World Cup or the clinical trials or like people's deaths. Right. That's not like that's not our morality. Like, you know, people can say whatever they want, do whatever they want with money.

27:20But if it's hospital money, I'm not putting in a gambling company. Right. So we can't hurt the world. We can't do things that are like vices, like, you know, that wind up like, you know, like making money but hurting people, right? So that's our first bet. And then if it's like, you know, neutral or if it's like going to be help the world that cancer cures, then of course we'll back up the truck. And then if you listen to the founder, I can cure cancer. Here's my unique insight. Here's wide load bearing. And you sit there going, what are these right? And then if he is right and you give him the capital and the connections and you help out, it might become Canva.

27:44And guess what? It's happened to me a few times. I got lucky.

27:48Peter High: I want to ask you about somebody you've already mentioned who I find fascinating, and that's Bill Campbell. and you've talked about how he's really influenced your operator style coaching. Talk a bit about his influence on you and thus the way in which you put some of his lessons into practice. Oh, Bill was amazing. When I first met him, I got exposure to him because of Sergey's chief of staff and he would coach Sergey. And he would walk in your office, just like yell at you, go like, you screwed this whole thing up. And then he'd hug you at the end going, I believe in you, you can do it. I mean, think about that, right?

28:18You have this crazy guy coming and yelling at you. who's like one of those. I did not know who he was at the beginning. He was just an old, I thought he was an old man that would just yell at me. And like, he had a full-time employee badge, but he didn't appear in the company directory, which I thought was kind of confusing. I'm like, who is this guy? And they said, oh, he's like, you know, Larry and Sergey's advisor. I'm like, well, they have advisors. And, but you know, I was also like 21 at that point. So I didn't really understand how Silicon Valley worked, but he was, he was always able to like point out and say the things that nobody could say.

28:44Right. Like, you know,

28:50the thing up, right? And here's why you left it up. Here's where you could have seen it differently. Here's where you could intervene. Here's why you made these bad decisions, but you can do better, right? And I expect you to do better. And he'd sit there and because he'd lay this out to you, you're kind of embarrassed, you're in shock, but he'd also sit there and give you the hug at the end going, I believe in you, you can do that, right? That's the first piece I learned. So I don't go yell at my founders, they screw up, I just sit there and I hug them. I'm like, it didn't work out, but you can do better, right?

29:14Here's a hug. So the second piece that Bill did did that was amazing was he understood the value of time. Most people don't understand the value of time. They create things that like kill your time, right? Bill was always sitting there going like, man, like, you know, if you're spending, not spending your time on things that like matter, like you have screwed up. That was the most important lesson I learned from him, right? Like one of the things he taught me as Sergey's chief of staff was like when Sergey, when I started working with Sergey, he's like, go through Sergey's calendar with him every day.

29:38Take a red highlighter, take a green highlighter, go and ask him that the, that the meeting or the thing that you did that you spent your hour on, on this calendar, give you energy or drain energy, right he goes if it drains energy highlighted green if it gave them energy highlighted i mean if it drains energy highlighted pink if it gave them energy highlighted green and he goes at the end of every day you should have a green calendar for sergey if you have a pink thing you need you need to delegate take it yourself or give it to somebody who can handle it because sergey cannot run the company if his energy is drained and then he told me to do it in my life like when i got frustrated with like you know things growing too big or like having to do too many politics or like having to deal with like budget reviews that would drain my energy just go do them your own life like and you have too many, you can have a couple pink days, right?

30:17But if you have a, if you have like entire three weeks of pink calendars, you're in the wrong job. Draining your energy, you will not survive. You will just get there and get resentful. And then suddenly your work quality will drop and then you'll become jaded. You said time to move on quick. And I did that. There were multiple times where I'm like, wow, this is like, there's 40 people all green. I get to build product. I get to sit there and shoot the shit with customers. I get to go launch stuff. I can go try something out. I don't have to go deal with lawyers yelling at me behind my back going, oh, he's going to wreck the company.

30:42And then eventually the company got big. There'd be processes. There'd be server things. There'd be log slipping. There'd be all these things I had to go manage the company on. I do budget planning. And then it was all red, red, red, red, red. And the same thing when Google Ventures got too big, red, red, red, red, red. I saw that same thing multiple times in my life. And when I see that, they'll taught me that it's time for you to say, life is too short. Go do something where you can apply your talents. And he taught everybody to go look at the world in terms of opportunity versus scarcity, right?

31:10Like, you know, people sit there and go, I can't leave, I don't care if it's pink, I'm going to trade off my future for like, you know, sitting there because I get paid too much and he doesn't give a shit about the money. If you do great things, the money will fall. He was right. Now, not everybody has that mentality, right? You have to grow up in that. You have to see it work because it is, it does require you to take this leap of faith. But Bill was right and I've taken everything he's told me when I, at the time, to spend with him to heart. That pink and red thing I still do to this day, I'm like, well, I got to make some changes if there's too many red days.

31:37Peter High: It must be one of the reasons why you're so adamant about making sure that FPV stays relatively small. Yes. I mean, it's my name on the door, so I get to make it all green for everyone. I want everyone to feel like they have green meetings. Look, you know, Bill was like, you can't expect everybody to sit there and go, oh, like, you know, you have perfectly green days every single day. You're going to have red meetings. You're going to have things that drain your energy. You're going to have to fire people. You're going to have to drain. You're going to drain your energy on a few meetings that you're going to despise.

32:03But if it's in service with the green days, great, do it. If every day is a red day, it means you screwed up, man. You're time for you to leave or make changes. And if you're boss, you make the changes. If you're an employee, you have no agency, you leave. That's your agency. And I took that to heart. Yeah. It served me very well, I have to say that.

32:22Peter High: And how do you pass that advice on to a founder who is... I'd be curious about how you You pass that. That's not for everyone. You can't. Okay. So this is the thing. You can't go say the founder and go like, oh, at least you go do that. I'm preaching. Right. You have to live it. You like, I lived it because I was helping Sergey with it. And then eventually I used it and applied it in my own life. If you don't see it work on other people, it becomes preachy. So I don't tell everybody to go do this. I'm like, look, if you want to manage your time better, I'm happy to give you some thoughts. If you have a great system, go do it.

32:50It's your company, your life. Right. And so like, that's the other thing. Like, you know, if people, if people ask, you know, sure, I'll tell you, right. If they don't ask, then I'd sit there and go, I will be here for you for whatever you need. I'm cheer you on. Right. Like they'll, they'll didn't give that advice to everybody. It required, you know, you being humble enough and being thoughtful enough and being smart enough to go internalize it and go say, I'm going to make the change. This actually might work. Most people don't do that. Yeah. That's the piece I learned in my growth over like, you know, the, my 30 years of being in this business, the best board members don't say it at the right moment or don't say it at all.

33:21Fascinating. Right. You usually invest across like start giving unsolicited advice. I'm like, you know, you might be right, but it's not going to land. So you're very wrong.

33:30Peter High: You and your firm invest across life sciences, deep tech, obviously software, other places as well. But I wanted to actually ask you about how does product and design, how does a lens towards that transfer into something like biotech where users and science are so much harder to evaluate? You mentioned the, you know, the curing cancer point, for example. how I think it's easier to evaluate. This is where we disagree, right? Tell me. If you think about it, I can spot product easily. Like this might be the next iPhone. Let's give it some money, right? Like a lot of people think it's hard because they haven't lived that excellence.

34:00I lived it for like, you know, 10 plus years at Google as a line product manager, designing products that billions of people use. I can spot a great product or a great person that understands product like in an instant. The pattern recognition is great, right? Like, you know, most people can't do that. So actually it's harder for most people because you haven't lived that excellence. At least in life science, you have the science. the science works and like does what it does or it doesn't work. And then like you have a couple other pieces where the founders are charismatic and get raised money and a bunch of other things, right?

34:26Like you can train and get a PhD and understand the science and life science companies, right? So like, you know, that's actually easier to go do than it is spotting good product. A lot of people say can do it, but like how many people like have actually done it, right? Like of the 111 investors, a lot of them were smart people, but like not, you know, one that said yes.

34:43Peter High: Yeah. Bruce, that's true. Very good points. I appreciate the counterpoint there. It's easy to do. It's easy to say you spot great products when you have 100 other investors rushing in and saying, oh, it's also a great product. Yeah, yeah, yeah. Interesting. Your investment in Onshore is a bet in AI transforming tax and accounting in an industry some might consider sort of like a little bit boring relative to others. But you think that boring industries are actually where a lot of the AI creates significant value. Talk a bit about that, if you would. I don't think it's so much boring industries.

35:11I think it's finding the right founder who sits there and says I have unique insight into companies. And he's like, Dominic, who's the founder of Onshore, he basically said, like, look, I understand that there's an esoteric version of taxes, which is credits, right? For farmers, small businesses, you use the right fertilizer, you buy U.S. tractors or something else. Like, we'll give you the government rebates, tax credits. In this country, tax policy is how we, like, you know, incent behavior, right? Like, you solar panels, you get a tax credit. You know, Biden administration, it's now gone in Trump, but they used to give you tax credits when you bought electric cars, right?

35:40You get, like, a tax rebate. They wouldn't give you the actual rebate. It would be a rebate on your taxes. And so this has been how the US does it. And a lot of countries do it too. And he's found a way to sort of find the credits for you and go back to a farmer, a construction company owner who's hired a lot, who used a lot of US manufactured products in their building and said, like, give you tax rebates back and use AI to find these folks and use AI to run the analysis and then find people like two or three million back in tax credits, especially for a small business owner. That's pretty significant.

36:10And nobody says no. Somebody said, I found$2 million. dollars and it's a great use case of ai but the data and the training that you need to go do this is like not something that like you can go buy from a core or like you know train on the public right the tax code is both esoteric and the expertise and understanding how to create these tax these tax credits are also something that you know a few people know at kpmg or in these boutique shops that they sort of run the other thing that he's learned that is that like look if you're a small business you're not usually getting these tax credits because it's so hard to get and you have to document it and you go to prison if you misrepresent it.

36:41The government is very vicious on finding every reason to put you in prison for filing false tax returns. Most farmers don't know about it. Most CPAs aren't well-educated in these tax credits. If you're a farmer, you're not using somebody sophisticated. If you're a large farm conglomerate, you hire KPMG, but you have to prepay them. You have to give them a retainer. They're not doing it for you for free. You might not get a dime back. You're taking all the risk of saying, I'll pay you to go do the analysis and file the tax returns and maybe a dime back versus dominic using ai and saying well like we'll only take money if we find you the tax credits you don't pay us if we don't and you know what if you have to lose other than running the analysis on the ai right and then having a you always have the human check it too to make sure that he can nobody goes to prison right because this is important um and so he's he's created this wonderful business where like ai is a great use case to help him find the efficiencies and then he can offer a business model that is that is we want you don't have to pay us we don't do the work so he can take all the risk on his side.

37:36It's like this unique insight that Larry and Sergey had that search engines should be fast. That seemed obvious today, but back then, it was to keep people on as long as possible because the incentive structures were different. If you think about taxes, if you need a lot of humans, you got to pay the humans. No one's going to do free work for you ahead of time if they don't find anything. That's the piece that he's discovered. What a great unique insight he's doing.

37:56Peter High: Really interesting. That's very boring. Everybody's chasing legal or something else, and I'm chasing tax credits. right. So I love that for good reason, as you point out, I said, somebody who has been a builder as well as an investor in multiple major tech waves. Now, what are some of the first things that you think are comparable to past waves that this AI wave has? There are numerous differences as well, but I wonder how you think about the past waves as history repeating itself to some degree that's impactful as you think about investing in companies that are riding this wave. Yeah, I think the thing you have to be careful about in different cycles.

38:30I mean, like, you I did a study on this because I was like, look, it's going to be important if I'm managing children's hospital money. If you go back to railroads in the 1840s, railroads made a lot of money, like the robber barons. You think of Stanford. He started his own university, which half the AI people come from today. But he was a railroad robber baron. You think about the Rockefellers and you think about all these people that made a railroad, none of them threw money on the 1840s. It was all speculation that railroads hadn't been built. People were buying up infrastructure. They're spending outrageous amounts of money on tracks and right away.

39:00And that was the first financial panic, right? Like people got wiped out. And you know, people like saying tulips in the 1600s, first financial panic, right? There wasn't a stock market. You couldn't go buy stock on tulips, but in railroads, you could. There's so much speculation. So all these drifters came in and would come to you and go, Peter, look, I got this crazy B &O railroad you should be investing in. Like, you know, just give me the stock. I'm going to go buy a bunch of, you know, instead of data centers, it was tracks, right? And guess what? They all got wiped out. Nobody could build it.

39:25Things got really expensive. You know, people going to get labor anymore. They're all building these railroads. And then eventually you got this panic and then you got a trough. Nobody cared about it anymore. And then that's when the Robert Barons all came in and go, let me go buy up all the right of ways and all the debris from the wreckage. And let me do it for pennies on the dollar. And then they made out like, man, it's timing matters and these types of things. So we think about it. Sometimes there is no timing. With stock-com crash, everybody went in. So many venture funds got wiped out. And crypto, same thing.

39:52A lot of venture funds got wiped out in crypto, right? Oh, speculation. everything's tokens nfts do you talk about nfts anymore and this happened like less than a decade ago right it's not like going back to the 1840s so you know some of these things that we have to be careful about is the timing right is the ri there is a really durable business model and the answer is no for a lot of this stuff right you know there's 16 legal ai legal companies how the hell you know what you're going to win you know what if open ai launches it tomorrow they have every incentive to go like build it and like launch it and then like you know disrupt the whole thing they don't want like you know 18 companies disremening the customer and they you know i was looking they just posted a stink for a ai engineer for legal i was like huh like you know if i were harvey or laguara or one of these companies and you know they're hiring one they're probably gonna hire 20 quietly right i'd be worried so you know some of those things you have to think about especially when there's massive speculation so we we that's why we're doing life sciences or why we're doing things with like tax credits or things that are durable right even i don't think open i is gonna be able to tax credit business anytime soon i don't want to warn them on it but like you know it's not their calling and they don't have the data to go do it either right like that's a really hard set of data to get because it's all private and you know the more the more of these tax credits you run the better you're trained your lms right so you want stuff where there's data about where they can't yep have mercur go buy it build it for them and you want things where like you know it's not going to be a core part of their business and it's not using even their lm and you're not sending the data free to open ai that will train their thing for you because you built your own sort of set of things canva has their own lms because you're not sending it to anthropic or open ai they don't need any of the user data compromised, right?

41:20So, and a lot of their creators are very worried about like, you know, AI stealing their stuff and like training and creating derivative works off of it. So, Canva is very careful about this too, right? Like, you know, they actually seek permission before they go and like run any of your stuff through their AI, which is something that like, I guess some of the elder elements aren't quite doing. Anthropic, I have one of these companies just said, well, a bunch of publishers for a billion dollars, 1.5 billion, right? You know, if you wrote a book, you might be getting a check soon um from anthropic but you know canva doesn't do that so that's some of the things that like you know are important for some of these companies that are building uh these durable boats not not these fly-by-night companies that you know or you know if if open ai or anthropic hires a legal engineer it's only the whole bit like you know this is all dead for like 16 plus companies that got raised bill each yeah very interesting um uh we ask these questions these are first principles right we sit there going like what is like this the launches tomorrow i i destroyed a lot of businesses at google i still work with that like you know there were all these ad businesses that people would have and like oh we're well adwords interface is inefficient doesn't do it didn't do a daytime bidding or didn't have time day of time bidding and all these other things where you could set different bids for different days parts of the time because like you know a click at noon is worth more than a click at like you know two in the morning and it was always the same price and so all these startups sprang around and i launched the feature and suddenly i'm like oh you destroyed my business i'm like this was an obvious feature to be part of adwords you can't you can't sit there and say like we did right Right.

42:41So, you know, it's kind of fascinating, but I saw firsthand at Google that, you know, they're starting to happen today. Amazing. Amazing. I'm saying I'm Mark Twain that I think at least it would attribute Mark Twain, right? History doesn't quite repeat itself, but it rhymes a lot. And I, I noticed every rhyme.

42:58Peter High: Fascinating. I wonder how is generative AI and agentic AI changed the way you work as an investor today relative to your earlier days as an investor? I think I'm much more efficient now at doing an analysis, right? Like here's the thing, like I use AI now to run analysis on some of my things or to learn, right? Like I say, like, okay, there's a new drug coming out. Pull the history of all the clinical trials. And before I had to go and search on a bunch of different journals or search engines to understand the landscape, before I had to go read a textbook, I literally had to go, you know, immunology comes and I'd go look at Jane's textbooks or, you know, which of the premier immunology textbook and understand the pathway of going, well, here's all the B cells differentiating.

43:36And here's the path that they're attacking. Here's why it's drug abort, why it's drug abort. or here's what everything's failed. That's a lot of visits to medical libraries, right? And now I just put up on OpenAI going, tell me why this pathway is on drug. And it gives you a brilliant answer that's much better than I could have found in the textbook because it synthesized not only the textbook, but every research channel that has discovered new innovations in that pathway since. It's pretty great, right? So that's helped a lot because I'm much more efficient at pulling this information that I used to have to either hire somebody to go do or do it myself with a lot of in-between.

44:07Look, we went through this ourselves. I was like, we're both old enough to remember that like that one point we were going to the library and using card catalogs. Right. I still remember some of these papers I had to go write for comparative psychology or there was a theory of justice class that I took at MIT. And I had to go write this paper about like, you know, all these important cases and like affirmative action and everything else. And I went to the freaking MIT library and the Harvard library. I like literally took the bus in Cambridge to the Harvard library and I go pull in a card catalog to eight books about this.

44:33Or, you know, I go into the remember the microfiche that people had. I was just about to say that. That's so funny. And that was, that was my search. And I sat there and I Googled that one. I'm just so much more efficient because I don't pull microfiche anymore at a public library. Right. And like all the journals are online. I'm like, man, like I still remember those days I had to do this. And like, I think AI is going to like do some of that where it's going to make it way more efficient. I'm already seeing part of this because I went through that same thing. My, my junior years when Google started, right.

44:56I'm like, wow, this is crazy. What a night and day thing. And I wound up working at that company, which was even more crazy. But that's that, that was the change that like, you know, Google and some of these searches and it's bought. And all of a sudden, now we're getting a much more efficient version of that, where I can pull up all this type of information that even a search won't find. Because the search just gives you a listing, right? They don't give you the synthesis of the information. If I say, help me understand this target to drug on B cells, I have to go pull it up in Jane's, I have to go pull it up in research papers to understand what the state of the art is and what people have found in the clinical trial studies, what drugs have failed.

45:28Now, I just run the same analysis of Claude where I run it off Gemini which uh has a little bit more recent information Claude still hallucinates quite a bit um and you know I compared the three results to make sure I'm not missing anything and I I the important thing to double check all those citations right like if you don't do that you you you're that high school kid that like submits the thing that's completely wrong right and once you do that like you know you have a lot better understanding of the state of the art than you do than you would do if you were just pulling up google search just literally the card catalog example where I don't have to pull up a bunch of books anymore.

46:03And then go through the index of each book going like, okay, which chapter is this covered in?

46:09Peter High: Who influences your thinking, Wesley? I wonder, who do you read? Other than what is synthesized for you, who do you read or listen to? It's all Charlie Munger, right? My business in investing is really about human misjudgment. What am I doing where I screwed up this investment? It's all human misjudgment. And Charlie Munger was a king of understanding wisdom and human misjudgment and then being able to communicate it like the way an uncle would do his like eight year old son 90 of what he said was incentive structure right he used to tell the whole story about how fedex like basically like would never get their packages sorted in time fred smith had this problem in the when he created that hub in memphis like it's like the early 90s i think was when when he moved to operations in memphis right and he had told this brilliant story and i got to know charlie at the end of his life it was like one of my most amazing experiences i didn't know have dinner with him and he told he'd always retell the story of like you know like like like the FedEx with Fred Smith.

46:56And it was one of the things I committed to memory. He basically said, think packages didn't get sorted on time. And him and Warren went up to Fred and was like, look, how are you paying the guys? Fred was like, oh, we tried all this stuff. We reinvented the computing. We did better training. We spent hundreds of millions of dollars trying to solve this problem. And he sat there and he goes like, let me just ask one simple question. How are you paying these guys? And he's like, hourly. And he goes, okay, well, what's their incentive? well they get lots of overtime right like you know they stay so of course they want to you know sort things like forever so things can get sorted i mean it's like just pay them a salary pay them more than they would make with overtime and hourly give them one additional incentive if they finish they can go home guess what everything 100 you know on top sort rate i'm like huh what's the old thing that he said if you show me if you show me the incentive i show you the behavior we don't have great incentives in this country we don't have great incentives in this business a lot of AI has weird incentives.

47:53People will have the behavior the incentive creates. And that's something that Charlie always would hammer into people. And people pretend to be, oh, yeah, I totally get incentives. And then they sit there and they go be part of an industry, whether it's healthcare, where the incentives are all about paperwork, or whether it's venture capital, where the incentives are all about management fees. And then they'd sit there and go like, oh, I totally understand this. And then go participate in something where the incentives are completely effed up. And you sit there going like, oh, some understanding you really did with Charlie.

48:20So I think about Charlie all the time in terms of like looking at investments. And that's one simple thing that, you know, out of the thousands of lessons that you could articulate, but like the incentive is probably the most proud thing that is part of it. Well,

48:33Peter High: Wesley, thank you so much for the lessons you've shared here. I've really gained mightily from our conversation. I hope as you reflect on this day that this was a green meeting as opposed to a pink one for you. Yes, it was wonderful. Hopefully many more green months to come. It's a pleasure. I hope so as well. Thank you so much, Wesley. Of course. Thanks for listening to TechnoVenture. If you enjoyed this conversation, subscribe wherever you get your podcasts and leave a rating. Thank you, and I look forward to seeing you next time.