Future Outlook and AI Innovation

If your days off happen to be Saturday and Sunday every week, then you will not have a place at Corgi. I don't sleep a lot. I think the average night couple hours, probably three to four hours. So you literally live in the office. Yeah. Yeah. I I have a mattress there and I would rat her like measure my life span in victories than than yours. Would you rather Cor gi was a trillion dollar company but you died at fifty or it was a fail and you lived till you were eighty? I mean I think the answer to that is pretty easy. I get a lot of backlash. I think the number of good companies is very small. The most insane workplace culture in America. The company works seven days per week. The founder lives and sleeps in the office. The team have a cafe that was built for them that is open 24 hours a day. Two-thirds of the first 30 team members have the company logo as a tattoo. Welcome to Corgi Insurance, the most insane workplace culture in America. Joining me in the hot seat today, their co-founder and CEO Nico, who just closed their latest funding round, valuing them at a whopping two and a half billion dollars. But before we dive into the show today,. so So what if your gym was already home? Well, one I'd probably be a lot fitter, and actually better than a gym you're driving to. Sounds pretty good to be honest. Well, that's AMP, a beautiful, wall-mounted, smart gym that brings strength training, hit, pilates , mobility, and yoga into one incredible system without the commute, the clutter, or the schedule. Ampad s to you. Personalized gains, AI coaching, automatic weight adjustments, and real progress tracking, all in a design that fits your home and your life. We actually have one right here in the 20 VC studio. I'm a complete sucker for fitting in a quick 15-minute bicep pump, which you wouldn't tell from watching the videos. The whole team though has also been using it, and no one is now missing the gym. 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That means faster resolutions, more consistent support, and just better experiences for every customer. It's also designed to be fully self-manageable so you can easily improve and adapt it as your business evolves. No third parties required. Leading companies like Gamma, Asana, DoorDash and Crypto.com already use and lovefin to deliver better customer experiences. So see what Finn can do for your team at fin.ai forward slash two zero vc. You have now arrived at your destination. Nico, dude I am so excited for this. I was more excited I have to admit for this than I am almost any other show in the way that one I think we align and two I think we align on something that's rather different. And so one, thank you for joining me, dude. Yeah, thanks for having me. I'm often struck with great CEOs. What is it that motivates you? Is it the fear of losing or is it the thrill of winning? Aaron Ross Powell I think you can't be afraid of losses. Losses are like beautiful because you know you can have asymmetric upside with winning. So I think you you have to love winning . I mean you have to love the victories. I think Jeff Bezos, he's he said something a number of years ago that has always really stuck with me. He gave it uh it has a baseball analogy, I guess very American. But you know, in baseball, there's four bases and you can score a ma ximum of or there's three bases and the home plate, but you can score a maximum of four runs when when you're at bat. So if if you go up to bat and every single time you swing, you try to like you know hit the ball out of the park, that's a losing strategy in baseball a lot of the time because the upside is capped. You know, you have you have maximum of four runs, but your your probability of striking out of of scoring nothing is quite high. In business, it doesn't quite work like that because instead of four runs, result ing from a home run, a home run might result in actually infinite upside. It might result in something like AWS popping out of nowhere. I really think like seeking asymmetric upside or infinite upside, uncapped upside with capped downside is the core of business and taking a lot of shots on goal. And if you look at kind of people who started important things, not every single thing they did work. Like Napoleon was the best general of all time, but he didn't win every single battle. Aaron Ross Powell, he won more battles than than average, cer certainly more more than most other generals. But I don't know. I I I think the the fear of losing can't really motivate you because otherwise you just become this like uh this creature afraid of doing anything. Aaron Ross Powell I spoke to Josh Young on your team and he said that Nico's probably the most aggressive person I've ever met. He sets goals that might seem unrealistic to others. When you think about the most aggressive thing you've done . I was gonna ask you what did you do that was too aggressive? But I actually get asked shit like that all the time. And I think that's totally the wrong framing because nothing's too aggressive. And that's so I'm gonna ask you instead, what were you not aggressive enough on with the benefit of hindsight? Yeah, it's it's a g it's a good question. I think going to to university, going to college, that was a a a big mistake. If you wanna do big things, you need to go out in the wilderness a little bit and be humbled, you need to kind of metaphorically get beat up. You need to, you know, go go through the lows before you go through the highs. I wasted some amount of time of my life doing that. Do you think university carries less weight than ever today? I don't know if it carries less weight or more weight or I you know, I d I don't really think about that because you kinda make your own weight in life and it it's kind of an interesting point because startups are fundamentally I think about like a crisis of legitimacy. And that was a big problem in like the the Roman Empire, right? Like it was a non-hereditary monarchy. The emperors weren't inheriting any legitimacy, so if they were a bit crap, you could just kill them and then replace them with the next guy. And I think startups are a little bit like that, where there's not like some inherent loyalty, you know, there's no reason to work for this company or that company, there's no blood ties, there's no inherited structure, and you can just go out and make your own. So I think the process of like going through a company is just kind of you know building that legitimacy. And I think that's why people try to point to things like the idea of tier one investors as a way to borrow that legitimacy. So universities, I I suppose the the the point is to give a credential that that carries some legitimacy, otherwise you you wouldn't do it. You know, you can learn all the material online, you can learn all the material with an LOM much better than you can from some professor. But I don't think the credential of a university actually conveys the legitimacy that it ought to. I think it's a bit too naked, you know, and on on the nose. It almost reminds me of Mark Andresen where he says essentially when a company is invested in by a fund, the fund is lo aning them the brand and the validity that the brand name of the fund has until the company is big enough where then it transitions and Corgi then loans the brand to Kanye or to JD at TCV, and it's the other way around. Do you see what I mean? It's like the legitimacy of brand. Aaron Powell Yeah. I mean he also says, do you want to be liked or do you want to win? So I think if you talk to a lot of founders, there's often a perception that that capital is fungible. And you know, what we're seeing with kind of the the the perception of funds and the idea of value add and and and tiers of investors is that perhaps capital isn't so fungible after all. What may he say that? Apple was invested in by Sequoia. But I I I think it'd be very unlikely that Steve Jobs would ever go flexing that Apple was a Sequoia company. You know, that would feel very strange. Uh that'd be very unusual. But but now, you know it it''ss it's not unusual when describing a company, say it's a it's a a tier one company or it's a YC company or this company or that company, with the descriptor being their investors to signify something about the way that the company acts or ought to be. And it's a bit unusual because people will say that out of one side of their mouth, then the other side of their mouth they'll acknowledge that when they invest in companies, they can't do anything about their investment. Like if the team's incompetent or if they're making bad decisions , then that's a really hard thing to to solve. No, that is a hundred percent true. I I have to ask you do you said that, you know, do you want to win or do you want to be liked? You and I both have a theory around work and work ethic and what it takes to win that's not always popular. Can you help me understand? You work seven days a week at the company, and the company is expected to work seven days a week. Yeah. Can you help me understand why that is and how you thought through that as a decision. If you're solving the most important problems or if you want to like dream big and like scale up your ambition, whatever you can get done in five days, I promise you you'll get more done in six and seven and so on and so forth. And I think that like if you're doing a startup and you're serious about it and you want to win, you want to do the biggest possible things, you want a sense of community and camaraderie and and have, you know, brothers and sisters in arms with the people you're working with, then you know, you you should go all out. You shouldn't do the the you know half asking it. Five days, why not four or three or two or one, right? I think you should just if you're doing something, you should do it properly. Do you not believe in the benefits of rest then? Like I'm I'm 100% with you on the w I mean for some people if they want to take a day off they should take a day off. But there's nothing about you know the weekend that I think that signifies Aaron Powell But they wouldn't have a place at Corgi. You know, you can take a day off every now and then. Aaron Ross Powell Dude, how does that go down in hiring? I would love to be able to do that. And you could say, Harry, you could do that. Yeah, you should. You can just say it and say, why? Because we want to build the biggest thing ever. And if you want to build the biggest thing ever, you need to win. And if you want to win, then actually is something that I think attracts the right type of person and absolutely repels the wrong type of person. Because particularly for young people, I think there's a lot of people that want to dream big, they want to do something big with their lives and important with their lives. And if you wanna do something important with your lives, you're gonna do it a lot and you're gonna win. And if you wanna be a winner, if you wanna be a killer, then you know sure you you can do that for thirty minutes a day, but I think doing it all the time is better. Aaron Powell Do you have people who turn up to you know interview processes and think it's it's kind of it, but don't realize the intensity? Aaron Powell Yeah. I mean we we have everyone do work trials, so that that scares some off. Aaron Powell What do you mean work trials? So before people come in, we really like to have them kind of like do kind of mock work for one or several days, especially if it's over the weekend and then they see the office full, that that helps them very quickly learn that we're not joking around. That's a benefit of actually working weekends is people can do it in their jobs without taking time off. What in a work trial impresses you most versus turns you off most? Because it is tough in a TD trial to have much impact your onboarding and whatever. Because if someone really wants it, if if they're like all in, if they want to like do the maximally hard thing, the ambitious thing with their lives and they actually want to go all in, then you normally can find a a place for someone like that. And it might not be exactly what they you know are applying for or what they think they're gonna be doing. But I think you should just s solve hard problems, you should do hard things. And you can kind of tell if someone's into that or if they're into checking in and checking out. Aaron Powell What questions do you find most revealing when you're interviewing people? I like to ask people what matters to them and why. I think that they tend to answer that honestly. Do you find money is an alarming response? If I said to you, I'm just hungry to make money, dude. I want to make money for my family. Do you mind? I mean I don't necessarily mind. That normally comes from a certain place, I think. Like to me, that answer normally would reveal that someone didn't have a lot of money. I think my answer for that is probably a little different, but I don't find that to be necessarily alarming. Although I I think that being extremely money money-motivated leads you to short-term local maximums that don't actually result in the most money being made. Trevor Burrus What is your answer to that? If it's not the money, we we would have I want to build the most important company in the world. I want to, you know, win. I admire the greats. I very much want to join them. I think that as people living in this like time and and circumstance, you know, we're subject to the world historical conditions in which we're in. If we were alive two hundred years ago, we'd probably be generals like fighting some sort of wars or something. And that would be very simple. The winning would just mean killing your enemies. And unfortunately you can't do that anymore. So I think that the next best thing and and and where we're at now is that you can actually in a positive some way like make a a really big difference in the world. So I want us to always be solving the hardest problems possible and uh I want to win. I want to add value. Aaron Ross Powell from one of your investors that you live in the office. Yeah. What does that look like? Do you actually live in the office? Yeah, I I think it's one thing to say like, oh, why don't you guys work seven days a week and you're on like some yacht somewhere like like hang out or at a visa or something. But it's another thing if you're actually like putting in the work. So I I think symbols often really matter. You know, like the cosmetic stuff, like having a sign on the building or we're gonna get to the sign D, didn't we? Yeah. Like the cosmetic stuff, I think it does matter. Like symbolism matters. There's a reason why governments and and religions and all of the really important things tend to care a lot about symbols. You know, the flags very important and all that. And I think that the symbolism around like working hard is quite different, like leading the troops from the front line versus like saying, Oh, why don't you guys work hard and and I won't . So you literally live in the office. And and that sort of thing. I I used to shower at the equinox like one street over and they they close very early, like eight PM on on Fridays, so that was unpleasant. And we don't have an o a shower in in our SF office. Our London office actually has a shower, so Yeah, I had this in the founder's room. Is that what it's called? Some people have called it that, but is no normally people just say oh n it's Nico's room. I got Founder's Room, showers at Equinox works every waking hour. How long do you sleep for? I don't sleep a lot. I think the average night a couple hours, probably three to four hours. But some nights I really do make an effort to try to sleep a little more because I find them Have you ever had health scares? Yeah. I I think sleep is important and I encourage people to sleep a lot. I think I would rather like measure my lifespan and victories than than yours. Would you rather Corgi was a trillion dollar company but you died at fifty? Or it was a fail and you lived till you were eighty? I mean I think the answer to that is pretty easy. Because if I'm dying either way, but for for now life is short. We'll see what happens. It reminds me of Olympians though. I don't know if you've ever seen this study. Whereas like they say would you rather live ten years less but have a gold medal and ninety eight percent of them said unwaveringly yes. You need to want it and that that's presupposing that that death is coming either way, which you never know. Brian Johnson has his way. You said if you're going to be a hyper gross startup and you're not working weekends, you're basically just quiet quitting. Yeah, I strongly believe that. But you're the only one doing it, aren't you? I don't know. I mean, uh if you visit very high grow th AI companies, at least in San Francisco, you know, the offices are pretty full on the weekends. I don't think it's a coincidence. Aaron Powell It's easy to look at this and go like and people will so unfair, harsh. You also have a chef seven days a week. Not anymore. Okay, talk to me about that. Why did you decide to have a chef seven days a week and why do you not now? Yeah, so I I I loved our chef. I thought she was really great. I think that just like ordering food is a little more like logistically easy. I think having food in the office is actually important be because otherwise people like lose a lot of time like going out and like getting food and like coming back is just very ineff icient. And you know, people need to think about like where they're going to buy the food and it's just, you know, extra like cognitive load. You know, you're you're spending more time like doing that than you are doing something that's this high leverage. I really dislike the culture of like pampering everyone or like taking care of them as if you're you're their parents. I think Google is like the worst of that. Aaron Powell Did it feel like you were pampering them when you had a chef seven days a week? Aaron Powell Maybe a little bit, but that that that's that's not the reason why we don't have a chef anymore. Aaron Powell Why don't you have a chef anymore? Aaron Ross Powell We really liked the idea of having a chef. And again, like the chef we we got was awesome. I I really liked having her. But I think that sometimes doing more that's not like core can like lead to logistical burdens. And it's better to focus your energy on things that directly lead to growth or indirectly lead to growth. Aaron Ross Powell Things that indirectly lead to growth. Yeah. So I actually said very excitedly the other night about our show to my girlfriend and she said, Huh, I just saw a job application and I was like, Well, I'm I'm sure it's not not related, it's the San Francisco Company, she's a lawyer in London. And she was like, No, no, no, it's the same one. Cafe Expansion Head. And I was like, That seems eerily similar to Corgi's role. And I was like, Maybe it is. Talk to me. You have twenty four seven Corgi Cafe Yeah. So when we rented out our building in San Francisco, we needed to get signage on the side of the building. And it was zoned or something. So when we got our primary floor, we were forced to take over the retail space. And it was like this empty barber shop. It was like really dungey, like you know, I'd been out of business for probably a couple of years. We moved in and, you know, everything was fine and you know, we have the sign on the side of the building, great. But I'd walk in every day and I'd see this like empty barber shop and it would just piss me off because like I'm paying for that, but like there's nothing in it. Like it's a waste of you know, it's a waste of everything. At the same time, a huge complaint I have was San Francisco. Everything closes really early. Like it's a big problem, especially in the financial district where offices and there's a lot of really great startups that want to like push themselves hard, but you cannot find a cafe, you can't even find a place to eat past like 6, 7 p.m. most days. Like things just are it's it's a ridiculous situation. Clearly, most restaurants don't have a growth mindset. The other issue that I think we wanted to address is that for people that are serious about technology, about building things, about starting things. There's not actually even in San Francisco, which is supposedly the center of technology for for the world, you know, there's not a lot of places where people can actually who are serious about that can come together, have a place where they can basically work hard. Yeah. How much money did it take to start a cafe? Aaron Powell We spent under $100,000 opening it. Has it been successful? I mean it's always full. If you go there uh you can go there at at three A.M. and I'd recommend writing term sheets to everyone there because they're working hard. I can't tell you, it's probably like over twenty people have told me like, oh, like I submitted my YC app and like the Corey Cafe and I got in or something something along those lines or I signed a term sheet there. You should do corgi ventures, which operates from three AM to five A.M. And it's like those founders that are there. Yeah, I mean the the problem is if anything becomes a a measure of success, it ceases to be a good measure once once all the you know the alpha disappears I totally get you. Does it make money? We lose money on the cafe with sponsorships because our drinks are sponsored and shout out to our drink sponsors. You have like brexpresso's. Yeah, Brexpresso , we have we have Deal, we have we have a couple of them. What a deal sponsor. It's the deal speed, it's a smoothie. Oh I like that. Yeah yeah, fair enough. Deal love deal speed. Yeah yeah. So so with with that, I think we're probably slightly profitable. If I was an investor, I'd say, Nico, I love you. Dude, you I love the energy. This is a fucking distraction. Yeah, th they hated it at first. Why why are you doing a cafe expansion head? Oh, you sound exactly like our investors. Oh no, no, no. No, no. No, no. I did. No, no. I did. I promised. I've learned that you don't get any credit as we're criticizing a founder. So I just don't. You know what I do? Dude, I'm here for you. Well done. Our investors didn't get the memo. So I heard plenty of that. But dude, why are you doing it I get it in SF cool? You're opening in London. Yeah. I mean we have an office in London. I think I'm very bullish London actually. Why are you bullish London? I think the talent is exceptional, both British talent and European. And I think you know there's very few places in the world where if you tell someone like pretty much anywhere to move to, they're like very happy to do so. I think San Francisco is one of those places. I think New York's one of those places, although I don't think that good companies tend to be in New York. And bec because of that, I think that there's certain exceptional qualities that London has. And given the whole like visa situation in the United States, I think there's actually a phenomenal opportunity for London to become like a center of AI and a center of tech. So we opened a London office before we opened a New York office. Like we you know we're very long London. Do you find it much cheaper to hire in London? It's a little bit cheaper. I think we you know, maybe maybe we're paying above market, but we're not paying that much. Uh the thing is if if you're working for like a salary working at Corgi, you're doing something wrong. Like if you're super hyped about your cash like comp then probably uh are you more generous than others on equity? Because you understand that you are asking for more of someone's life being seven days. Yeah yeah we're we're generous with top top offs. After people are working we we give more more equity based upon performance. Okay. So it's like accelerators on milestones hit. Yeah, I mean it's it's more it's a little more ad hoc than that, but yeah, something like that. Aaron Powell We said about distractions. A lot of founders angel invest . How do you think about founders actively angel investing? I don't angel invest. I think it's a distraction. It doesn't feel like it's uh it's core to to like winning. Have you sold secondaries? No, I've I haven't sold any second people are always trying to buy them, but I've I've yet to sell a single secondary. Why is that? Because our equity's going up and w or maybe I shouldn't say that, but I believe our equity is going up and and I'm voting with my feet. If I have the in my opinion, the scarcest asset that I could have any meaningful influence over and I think that we're going to keep doing well and keep kicking ass, you know, why would I sell that? Like I don't really have a Well you don't have huge rent to pay, that's for sure. That's true. Despite the bullishness on London, you're still super bullish on SF. Yeah, I love San Francisco. Why is the amount of great talent building in SF is it just Aaron Powell That might be part of it, which you know is is maybe a bit of a problem that London has. You know, things are actually open later in London and you know there's more people about too many too many pubs. That's that might be a problem. Do you drink? Um no, I don't drink. But I think San Francisco is a special place because particularly with people in in the U.S., if you want to do something big with your life and you're not really quite sure like where to go to. San Francisco is like a you know an end destination where like you know, if you're a bit nerdy and if you love technology, you love programming, you love kind of these slightly unpopular sort of topics, it's a place where you can actually like find your people oftentimes and where like you'll find yourself moving to. And I think that that's a a special quality. It's almost like a you know a spiritual quality. Like you you know, everyone's in an exile or something. And I think that that 's something that's like very unique. That's why New York is not a good place to to have a company at all. The people that that move their companies to New York uh do so because they want a date. You know, that's the only reason real reason why they do. Same with Miami or uh you know all of these other places. If you're hardcore about startups and you're American, then I think you should you should go to San Francisco oftentimes. I mean there's super great other cities. Like I I do like Chicago and we have an office in Dallas that that's really great too . And if you're hardcore about startups outside of the United States, I think London is is second to none as well. Although you gotta avoid the pubs. The pubs are really getting it. I get you. We've spoken a lot about everything from chefs to signage on buildings to Corgi Cafe to work ethic. Well you're a little bit younger than me, but I do reflect on how I've built the company. When you reflect on I don't dwell on mistakes. How very Mark Andrewsen of you. Yeah, I think I look more at the victories than the losses because I think there's more There's a brilliant m commencement speech by Matthew McConaughey at the University of Texas or University of Houston. He says, you know, study success and the importance of lessons from success. If I were to then flip it and say what success have you studied and what do you learn from it, what would you say that is? I think that you need to look at the greats. And the greats are oftentimes outside of of the context of startups. Like, you know, people like there's obvious like famous startup founders, but I think that looking at everyone from Alexander the Great to Napoleon to, you know, so on and so forth is is also very informative. If if you want to like change the world, if you wanna do something important and and you don't want to just be like a mimetic copy of everyone else or you wanna be class president or something, that's fine. But if you wanna actually like do something big, then I think that being a student of the greats is great. The important thing I think is is probably not copying them. Like you should have your own style. But being a student of history is probably a a pretty positive thing. If I were to ask you, what's Corgi's culture in one word? What would you say it is? We have a culture of winning. Winning. That's it. That's it. I maybe in the past I would have answered like ex founder, like hackers, like other things. But I think all that's actually kind of fake and we just like win Can you maintain the intensity that you have today when you're at a thousand people? Yeah. Easy. Really? I think so. Why has no one else been able to do it? Aaron Powell So naturally there there's roles I think that that creep in. A a lawyer or an accountant are not gonna work in the same way that you know a software engineer might. And that's just a fact of life. So okay. So if they don't wanna work quite as hard, then you just need to hire more of them for the same work output, which is okay. It's just like a return on investment calculation. take the the off-ramp of being super hardcore and you need to accept maybe lower growth but less volatility. I personally, at least at the current stage I'm at, don't mind volatility is something that I think is can produce alpha in a lot of ways. Aaron Powell What would you say to people who say that you're exclusionary in the work culture and that parents couldn't do what you want? I mean we have plenty of parents that work at Corgi, so life's about trade-offs and sacrifices. I think Corgi is a great place to work if you want a sense of community and camaraderie with the people you work with, if you want to have friends in the workplace, the social life attached to your workplace, if you want your work to be additive to your life as opposed to separate. That applies whether you're married, whether you have kids, don't have kids, some of our best people Do you care about the backlash that you get when you speak about this? Yeah, yeah. I mean I get a lot of backlash. The the death threats and the DMs, you know. People people think I'm I'm nuts. Do you care? Not really, no. I don't know. I mean I have you have a cad? Yeah, I I don't know. I I think when you're a young person, particularly I I think young men, you know, don't have that much support within society and I think is something of course that like weighs on people, particularly if you don't have a lot of external validation or credibility yet. Credibility is something that is hard to get, which goes back to the crisis of legitimacy that I think is core to startups. Aaron Powell Do you think you're legitimate yet? Aaron Powell I think you're legitimate when you're in that you don't get fired for buying IBM. And I would in my context as a fund, if you're Andreason or you're you name these great like big large platforms, you don't get fired as an LP for doing Andrewson. Right. Can't like period. Yeah. That's probably exactly right. The thing is, in the fun context, you know, Andreessen or Kleiner or even Sequoia back in the day, at some point they were just a couple guys in some shitty room that like didn't really know like what they were doing and were making it up as they went along. And they were probably pointing at not probably they certainly were pointing at other people and saying, oh one day we'll be legit like them and the institutional LPs will take us seriously. Aaron Powell There's always you know more legit, right? You can go go from pension funds to university endowments to the government, you know, that's the ultimate form of legitimacy, probably, because the government can just take people's money. Aaron Powell What are your lessons on paying people? So what I've learned, for example is that when people ask for more money, they tend to be very good. When they ask for more title, they tend to be very bad. Any lessons on salaries, benchmarking, comp low cash comp is as something good, generally speaking. Who ends up doing extremely well? Like if people are doing well, you need to just like give them more like equity especially and make it so that like if they're doing a very simple return on investment calculation that the highest EV thing they can do is like work in their their current role. And if you can't provide that upside, like there's no reason for them to like continue like working super hard and they should be doing something else, whether that's working for someone else or starting their own thing or whatever. I think separate from kind of the comp and the simple EV calculation is that you need to actually be like solving big problems. And if you're not solving big problems, then no matter how much you pay people, you're not going to retain them if they're actually good. You can probably split like with any any organization of the team into three, you can have people that are like really good, people that are kind of fungible and like mediocre, and then people that are bad. And I think getting rid of the bad very quickly is is important, even if it makes a lot of noise. Aaron Powell Do you keep the mediocre? Aaron Powell I wouldn't put it like that, but you know, I I think in any organization there's people that, you know, you wouldn't be devastated if they if the The question I always ask is knowing what you know now, would you hire them again? Yeah, I mean there's a lot of people where the answer might be yes, but you know, you're not gonna be sobbing and punching the wall if they're uh if they're no longer with you. Fundraising is a big part of your job as a CEO. You recently raised uh I think one point five. Yeah, one point three. One point three from TCV. Love TCV, love John Doran, spoke to him before the show. What are your sing le biggest lessons on fundraising? Having raised now across pre regulated, post regulated, revenue scaling very fast. What are the most non obvious lessons you have from raising several hundred million Aaron Powell I don't know if I'm actually an expert there or anything like that. Do you think you're a good fundraiser? Aaron Powell I think I'm alright at it. I I've I've had to do it for years now. So I think if you have to do anything for years, you can't known when you started. Yeah, when I started, my pitch was not very good. Like I remember my first pitch. Who was it to? Probably first round capital was my my first pitch. Okay. From way back in the day, the very first VC I ever talked to was at Google Ventures. But yeah, I mean my first pitch for Corgu I think was maybe first round capital. I remember I I like took a red eye the night before, and my eyes were actually red. I looked like I was high or something. I was like so nervous because we had to get five million dollars and we had like twenty-four hours or I flew back on Thursday night. I was like, oh we'll get the money to you in a couple of days. Like you know how the banks are, it'll take some time to transfer the money. So I I started pitching Friday. We had Saturday, Sunday, and had to get the money by Monday. And you know, I I think the pitch was not was not very good, honestly. It was I think it was a lot of like like just trust me, I wasn't telling them the name of the insurance carrier because I was afraid they'd like call them and ruin it. The f the first set of pitches I did weren't weren't that good. And you were raising two on ten? We were raising uh five on uh twenty-eight with that one. That was recently. I mean it was like two years ago. Yeah. What was the best VC meeting you had? Aaron Ross P Theowell worst are when it's like super structured and when they start asking me like BS about like our like balance sheet or like you know they get in the nitty-gritty. I'm I'm I'm not that type of guy. I think that the best ones tend to be when someone is like very like growth-minded or product-minded, we just get to vibe about like where we're going and and like how we're gonna win. So what was the best VC meeting that didn't invest? I've had plenty of great ones that didn't invest. I'm not gonna put them on the spot because they might they might invest later on Aaron Powell Okay . What was the worst? Oh I've had some really bad ones. Have you had some really bad ones? I've had people like especially the first round, like the early stage investors are disrespectful. I've had people dveriving, I' had people flossing their teeth on the meeting, like chowing down food like like barbecue ribs or something where it's like getting all over their face. I've I've seen it all. What do you say? I'm like please finish frosting. It's okay. Like, I had one on a FaceTime where the guy was like hitting his vape and I thought he was asleep because he just had his eyes closed, like leaning against the wall. I've had some like crazy pitches, particularly at the early stage. What are your biggest advice to founders on pricece. Pri is a difficult one. Yeah, I I think price Brian Chesky told me one time to never take the highest price and I've taken that to heart. So we never take the highest price ever. That's just a good rule of thumb. Like we always go with like the second or third highest price I don't do a lot of negotiating on price. I just kind of see where the market's at and then if something seems reasonable I just stick with it. And you know, we could raise all of our rounds at higher prices, but we never do. Aaron Powell How long does it take to raise rounds for you normally? Aaron Powell A couple days at most. Aaron Ross Powell If you're in the market for a long time, it's a bad thing. Maybe it's a good thing for your like valuation or for the amount of money you're raising or funds you're raising from. But I think it's a bad thing for the company because you you start to optimize for like selling equity instead of like selling your goods and services. Fundraising is like super distracting. It's not quite as bad as the audits after you like get the term sheet, but like it it is pretty distracting. Aaron Powell Couple of days at most. I hear you . I'm on the other side of that deal. And I'm like, dude, I'm with you. You don't want to do it. I don't want to be in a fundraise process with you either. But I do want to get to know you. And I do want you to know me. Well, V VCs always say that, but the thing is they could put in the work to get to know you, but they never do. And I think that's uh again this is interesting because like we're totally on the other side of the table. We fucking try, and you know what we get? Thanks so much for your email. We're heads down. Well what the fuck. I'm heads down. You know, because if you're if you're working on an important deal that's gonna like double your your revenue, the last thing you want to do is meet with some VC. I get it, but then that helped me understand. You know what an investor told me one time actually? He said good companies get deals done. At first I was mad. I was like kind of pissed to hear that. Like it was like, you know, like a like a backhanded, like uh it wasn't even a compliment, I guess. It was just an insult. He was implying that we weren't a good company because we weren't getting deals done. Trevor Burrus I've actually taken it to heart, because I think it's true. Good companies do get deals done. Since then, we've like shifted our approach and we've started getting deals done. We've stopped being such absolutists and we move with haste, time kills all deals, and we like as a company, we like get deals done. Like that's the key. I think that a venture capital firm is it's a lot of things, it's a brand, it's a lifestyle business. But one thing is certainly is as a company, good companies get deals done and I think that applies to to venture capital firms too. Some deals, you know, are made in in times of crises. I think the the venture deals that I respect most of all are the ones that I hear about from my funds where their company was not doing well at all and a VC came in and saved them. And the amount of gratitude I think that like founders have for something like that is extreme. The amount of courage it takes to do like something where the company might be contentious or controversial or the metrics might be going the wrong direction, not the right direction, that that type of behavior I think is is hard. And I think doing the hard thing in venture is is rare, unfortunately Aaron Powell But genuinely then you would rather do a deal with someone you don't really know if it's in a few days. One thing I know about them is they can get deals done quickly. That's true. And we've I you know, I've I've had plenty of bad investors in my life. Bad investors much worse than no investor and it's hard to get rid of 'em. But the the thing is, if you're doing well and if you're pricing your company cheap and if you go out to market, you can get a deal done very quickly. It's just the fact Are you not doing a disservice to your existing ambassadors by not? I don't think so. They all got good deals too. You know, if we if we were a public company we'd probably be worth uh less 'cause the the public markets don't know how to evaluate high growth or potential. Talk to me about that. Look at the financial services companies on the public markets. They're all terrible. They all don't grow. But they you know they're they're they mispriced or are they actually accurately priced because they don't grow and they have poor margins? Some of them have good margins. They make money. Private markets feel to me like they're a vehicle for for valuing growth, whereas public markets feel like they're a vehicle for valuing like cash flow. In the past we'd call like dividend stocks. You know, maybe that's that's not so favorable if you're looking for for asymmetric upside and are an investor because you don't have access to you know private deals as much. But certainly from a company perspective. Do you not think at some point all companies are embodiment of their future free cash flow. That is what a company valuation is. No, I I I don't think so because I mean maybe at some terminal point from a theoretical perspective, but brand is worth something and identity is worth somet Money, what would you do that you're not doing today? So for example, I'd be on the side of an F one car. I would be opening Japan. If you had unlimited money, I think you'd have uh, you know, bigger things to do than than be on the side of an F one car. Right. But I mean there there's a lot of things I'd I'd love to do. Like I think within the context of Corgi , like every single like super, super regulated like financial institution type where right now it's like run on like fax machines and with like boomers. Like we'd like to like you know have those not waste people's time and and charge less fees and make everything a little more protected and a little more efficient, a little more profitable. I think outside of that context, I'm a techno-timopist . I I believe very strongly in the power of technology to make the world a better place across a wide variety of industry sectors. Corgi is a bet mostly on like the most regulated sectors, but there's very few problems that technology can't solve. And probably there's a lot of areas that are exciting, like in medicine and and mental health. There's crises in a lot of like concurrent areas where I think technology can make things a lot better. Aaron Powell What role do we not have today that you think we will have and be very commonplace in five years time? I don't know if it's like a role in particular, but I think that actually AI makes sales and marketing much more important than than it was in the past. In the past, I think if you had a really rock solid, like super hardcore engineering and product team, you could come out with something that would just like blow everyone away, it'd be faster, it'd be better. Now you can make something faster and better. You know, if you don't have people to sell it or to market it or to tell people that it exists, it's not really worth the whole lot. The like organic network effects around particularly B2B product launches just don't really exist in the same way that they used to. Aaron Powell Do you think traditional B2B marketing is good? Aaron Powell I think traditional B2B sales is good. I think marketing is awful. Why? There's a lot that B2B could learn from consumer. The conferences are not it. Like I'm I'm not a fan of you know, going and hanging out with a bunch of like sweaty like people in a room. Like I don't I don't really like that. I think that like consumer companies have perfected marketing and B2B companies have perfected sales. Much like in a company where you have like a dominant product, how that kind of becomes the company and like it's hard to like really care that much about auxiliary revenue streams. As an industry, if you're selling B2B products, like you're gonna get very good at sales and marketing will tend to be an afterthought in most instances I do want to move into a quickfire where I say a short statement, you give me your immediate thoughts. Does that sound okay? Yeah, sure. So I think changing one's mind is important. What have you changed your mind on in the last twelve months? There's a lot I've changed my mind on. I've grown to value experience a lot more. In the past, you know, I've I've probably made certain statements around uh you know boomers being slow and bad or I've definitely uh undervalued people that have been doing something for a long time. Because a lot of times there's like these like little nuances or edge cases. When you do something for a long time, you you pick up and maybe you're not as fast or as efficient or as able to use the latest tools. But there's an extraordinary amount of knowledge that lives in kind of the older generations, especially the retiring ones. And I think it's a big problem in that there's there's trillions of dollars to make getting that knowledge out and putting it inside of inside of computers that can think and talk. I don't think I I viewed those problems in in in that lens. Uh you know, I I think I just considered old people using fax machines moving at two miles per hour to be like, you know, something uniformly bad but now I see that there's value in their knowledge. Who do you not have on the board that you would most like to have on the board? I don't like boards. Why? I believe in executive decision making. You know our board's great and yada yada yada, all the disclaimers . But I think you just need to be able to decide and you need to be able to do things. You think Elon Musk or Mark Zuckerberg are caring what their board thinks or their board. Like every committee decision, I think , is like BS. Like sometimes you need to be able to take an unpopular stance and you just need to be able to plant your flag in the ground. I think so a little bit. Like it's you know, a little theatrical. I guess it is it's good to make surere you' not like a scam or like doing like blatantly illegal stuff. But if management is like unethical or unscrupulous enough to scam people or do illegal stuff, then they're gonna do it anyways, probably with or without a board and that's a management problem . Aaron Powell You can buy OpenAI or Anthropic today, both at the same price, 900. Which one do you choose? Aaron Powell Yeah I'm gonna get in trouble for this probably but I guess the disclaimer is this might be a stated preference versus a re vealed preference, given that we spend maybe like four hundred thousand dollars per month on on anthropic and zero dollars on open AI at the moment. But I think that like spiritually like open AI is I guess a little more pure because they kind of created, you know, this idea of like a AI lab as a company dating all the way back to YC research. And you know, anthropic is a result of employees that didn't like the management or the direction. There were complaints about profit and and ethics all this other stuff and you know the the EA movement and all of that. You know, I I I think when you're like when your origins are are that impure, it's it's a little hard to to overtake the king. And uh you know right, now, Anthropic, frankly speaking, has been out executing OpenAI. Their product's much better. We use the best product in every category, at least fr from uh from an enterprise or like workflow automation perspective, Anthropic's better. So OpenAI needs to lock I don't think it'd be that hard. Although uh all of the labs are always trying to make us signed contracts and if they give us a big enough discount on tokens then we'd we'd consider it. Aaron Powell What is no one talking about that you're spending more and more time thinking about? Aaron Powell To me, there's good companies and there's you know everyone else. I think the number of good companies is very small. And a good company wants to win is like world historic, we'll be talked about in like a hundred years. Those companies, you know, there's just not many of them because people don't want to win. They don't want to put in the work. They don't want to and that's okay. Like it's okay to be average and part of the mediocre masses or whatever. That's all right. But I think that the cultural or internal kind of character of the companies that are good companies is something that's not appreciated enough. From a metaphysical level, there's a really big difference between Andreal and like Anthropic, right? Those are like super different companies. I think both of those could be good companies. But I I don't think people really understand the philosophy behind the management teams that they're investing in. Trevor Burrus, Who do you think is the most underappreciated CEO stay? When you look at your style, who most aligns to your style? My style is my own style. I try to just do me. I think there's plenty of super underappreciated CEOs that like area where more more than kind of venture-backed companies, what what I would love to see more of our venture funds, you know, speaking out about these sort of important topics. And I know like startup founders love to clown on VC s for chiming in about like topics that they might not know a lot about. But I think that venture funds are actually in you know despite the fact that they're you know need to raise from LPs and LPs, you know, can crack the whip or whatever. Like I think that venture funds are in a really strong position to influence the way that the startup ecosystem looks because they're setting the incentives and incentives often drive behavior. One thing I would love to see are the the CEOs or the people that that are running venture funds actually take an a a more active stance in aligning their you know deployed capital with the changes that they like to see in the world. And to me that that's that's perhaps a more important issue than like any particular company's Aaron Powell Would you blame VCs for the dramatic increase we've seen in fraud, especially around ARR? We put so much emphasis on zero to a hundred million in X amount of time. Aaron Powell I I mean like a lot of the issues with fraud we've seen are downstream of like credentialism or that quest for like legitimacy in a lot of ways. You know, I'm I'm not going to speak about specific frauds, but I'm sure some come to mind that kind of check those boxes. I think VCs are are partially responsible. But as a venture investor, after you invest in a company, there's very little you can do. So if the management is unscrupulous, is is going to be scamming people or the product doesn't actually work or whatever, then I don't think you're really responsible for that management team committing fraud. I think on the extreme you have if you go back in time a couple of years, a lot of the crypto investors would encourage company founders to take on quite a lot of personal liability, including criminal liability in many cases. And basically they'd be like arbitraging that and like pumping the tokens or whatever. In hindsight, I guess that was the wrong type of tokens to work on. And I think in those cases, probably venture investors bear more responsibility. I think that people blaming like you know YC or whatever for some of their companies being frauds is probably not like directionally correct because it's not like any venture fund really wants to like invest in a fraud. And people that are like doing these things, they're very good at wrapping it up and disguising it in such a way that that it will pass muster, especially w if a a round uh is moving quick, which most good companies rounds do. Who was your first believer with Corgi? It was probably Jared Friedman from YC. Yeah. There's been times where he was our only believer. You know, everyone else is a doubter, is a naysayer. Um but Jared Jared's always been there for us. Would you do YC again? Yeah, I do it again. Final thing for you. What are you most excited for when you look forward to the next 10 years? What are you like this? I can't wait for. You know, it it's it's a little hard to say because if you ask that 10 years ago , the technology that people were really excited about didn't exist yet. It was only late twenty twenty two that people actually started getting with Chat GPT three point five that large language models were obviously very important and very exciting. Like within the the next ten years, technology will solve a lot of a lot of problems. Perhaps it'll create some too, but I think it'll solve a lot more than it creates. I think that there's certain areas where venture investing hasn't worked before, where there could be like category defining outcomes and where there could be new uh kind of industries where where smart people are actually interested in going into. Like biology is one that comes to mind. I really strongly believe that you know we're gonna probably see more like chat GPT moments maybe a couple years from now that uh that will really shake things up. Dude, I have to say it's been so wonderful having you on the show. As I said at the beginning, uh some of my most unpopular beliefs you align with completely , and so it's nice to have a kindred friend. Thank you so much for joining me today, man. Thanks for having me . But before we leave you today, so what if your gym was already home? Well, one I'd probably be a lot fitter. And actually better than a gym you're driving to. Sounds pretty good to be honest. 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