“Welcome to Corgi Insurance, the Most Insane Workplace Culture in America”
Startup Culture / Leadership / Fundraising
Joining me in the hot seat today is Nico, co-founder and CEO of Corgi Insurance, who just closed their latest funding round valuing them at a whopping $2.5 billion.
Interviewer
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. Um, and so, one, thank you for joining me, dude.
Nico
Yeah, thanks for having me.
Interviewer
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?
Nico
I think you can’t be afraid of losses. Um, losses are like beautiful because um, you know, you can have asymmetric upside with winning. So, I think you have to love winning um, and you have to love the victories. Um, and um, yeah, I think Jeff Bezos he said something a number of years ago that has always really stuck with me um, in that um, he gave it as a baseball analogy. I guess very American, but um you know in baseball um there’s four bases and you can score a maximum of or there’s three bases and in the home plate, but you can score a maximum of four runs when you’re at bat. Um so 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 upside is capped. You know, you have a maximum of four runs, but your probability of striking out of scoring nothing is quite high. Um, in business it doesn’t quite work like that because instead of four runs resulting from a home run, a home run might result in actually infinite upside. Um, it might result in something like AWS popping out of nowhere. Um, so um I really think like seeking asymmetric upside or 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 um kind of people who started important things, not every single thing they did worked. Like Napoleon was the best general of all time, but he didn’t win every single battle. You know, he won more battles than than average certainly more than most other generals. But um I don’t know. I think that the fear of losing can’t really motivate you because otherwise you just become this like uh this creature afraid of uh you know doing anything.
Interviewer
I totally agree. I spoke to Josh Young on your team and he said that Nico is 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 going to ask you what did you do that was too aggressive? But I actually get asked stuff like that all the time. And I think that’s totally the wrong framing because nothing’s too aggressive. So I’m going to ask you instead, what were you not aggressive enough on with the benefit of hindsight?
Nico
I think going to university, going to college, that was a big mistake.
Interviewer
Why?
Nico
You know, if you want to do big things, you need to go out in the wilderness a little bit and be humbled. You need to kind of uh metaphorically get beat up. Um you need to, you know, go through the lows before you go through the highs. And um you know I wasted some amount of time in my life uh doing that for sure.
Interviewer
Do you think university carries less weight than ever today?
Nico
I don’t know if it carries less weight or more weight or I you know I don’t really think about that because you kind of make your own weight in life and it’s kind of an interesting point because startups are fundamentally I think about like a crisis of legitimacy where um you know and that was a big problem in like the Roman Empire right like it was a non-hereditary monarchy you know the emperors weren’t inheriting any legitimacy so if they were a bit crap you could just kill them and then you know 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 uh you know, blood ties. There’s no inherited structure and um and you can just go out and make your own. So, um I think the process of like going through a company is just kind of um you know, building that legitimacy and I think that’s why people try to point to things like the idea of tier one investors um you know, as a way to borrow that legitimacy. So um you know universities I suppose the point is to give a credential that carries some legitimacy otherwise you wouldn’t do it um or you know you can learn all the material online you can learn all the material with an LLM much better than you can uh from some professor um but I don’t think um the credential of a university actually uh conveys the legitimacy that it ought to. Um I think it’s a bit too naked, you know, and on the nose. It almost reminds me of Marc Andreessen where he says essentially when a company is invested in by a fund, the fund is loaning 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 the fund and it’s the other way around. It’s like the legitimacy of brand.
Interviewer
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 capital is fungible. What we’re seeing with the perception of funds and the idea of value add and tiers of investors is that perhaps capital isn’t so fungible after all.
Nico
I don’t think Apple was invested in by Sequoia but I think it’d be very unlikely that Steve Jobs would ever go flexing that Apple was a Sequoia company. That would feel very strange. But now, you know, it’s not unusual to when describing a company, say it’s a tier one company or it’s a YC company or it’s a this company or that company with the descriptor being their investors. Um, to signify something about the way that the company, you know, acts or ought to be. And um and it’s a bit unusual because you know people will say that out of one side of their mouth and the other side of their mouth they’ll acknowledge that when they invest in companies they can’t do anything about their investment you know like if the team’s incompetent or if they’re making bad decisions then that’s a really hard thing to solve.
Interviewer
You and I both have a theory around work and work ethic and what it takes to win that’s not always popular. You work seven days a week at the company and the company is expected to work seven days a week. Can you help me understand why that is and how you thought through that as a decision?
Nico
If you’re solving the most important problems or if you want to like dream big and like scale up your ambition — let’s presuppose that you want to do something big and not small. 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 um 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 have, you know, brothers and sisters in arms with the people you’re working with, then um you know, you should go all out. You shouldn’t do the halfassing 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.
Interviewer
Do you not believe in the benefits of rest?
Nico
I mean for some people if they want to take a day off they should take a day off. But there’s nothing about the weekend I think that signifies rest. You can take a day off every now and then. That’s all right. But if your days off happen to be Saturday and Sunday every week then you will not have a place at Corgi.
Interviewer
How does that go down in hiring?
Nico
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 it’s 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 want to do something important with your lives, you’re going to do it a lot and you’re going to win. And uh if you want to be a winner, if you want to be a killer, then um you know, sure, you can do that for 30 minutes a day. Um but I think doing it all the time is better.
Interviewer
Do you have people who turn up to interview processes and think it’s kind of it, but don’t realize the intensity?
Nico
Yeah, I mean, we have everyone do work trials, so that scares some off. I think it’s really important people need to know what they’re getting into on both sides. So before people come in we really like to have them kind of like do mock work for one or several days especially if it’s over the weekend and then they see the office full — that helps them very quickly learn that we’re not joking around.
Interviewer
What in a work trial impresses you most versus turns you off most?
Nico
The soft skills matter I think more than the hard skills for me because if someone really wants it, if they’re like all in and if they want to like do the maximum, the maximally hard thing, the ambitious thing uh with their lives and they actually want to go all in, then um you normally can find a place for someone like that. And it might not be exactly what they are applying for, what they think they’re going to be doing. Um, but I think you should just 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.
Interviewer
What questions do you find most revealing when you’re interviewing people?
Nico
I like to ask people what matters to them and why. I think that they tend to answer that honestly. Being extremely money motivated leads you to short-term local maximums that don’t actually result in the most money being made.
Interviewer
What is the reason if it’s not money?
Nico
I want to build um the most important company in the world. Um, 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 circumstance, you know, we’re subject to the world historical conditions in which we’re in. If we were alive, um, you know, 200 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 uh, you know, killing your enemies. And unfortunately, you can’t do that anymore. Um, so I think that the next best thing and where we’re at now is that um you can actually in a positive-sum way like make 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.
Interviewer
I heard from one of your investors that you live in the office.
Nico
Yeah. 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 hang out or at a villa or something. Um it’s another thing if you’re actually like putting in the work. So I think symbols often really matter, you know, like the cosmetic stuff like having a sign on the building or um you know, the symbolism around like working hard um like it’s quite different like leading the troops from the front line versus like saying oh why don’t you guys work hard and I won’t. Um, so yeah. I have a mattress there and that sort of thing. Um, I don’t spend every single night there anymore. Um, because I used to shower only at the Equinox like one street over and they close very early, like 8:00 p.m. on Fridays. So, that was unpleasant. We don’t have a shower in our SF office. Our London office actually has a shower.
Interviewer
How long do you sleep for?
Nico
I don’t sleep a lot. I think the average night um couple hours probably three to four hours but some nights I really do make an effort to try to sleep a little more cuz I find — I candidly give everything to this. Um, I have psoriasis and I had heart palpitations because I was just so all in and I still am, but I do have to like monitor my sleep. I think sleep is important and I encourage people to sleep a lot. Um, I think I would rather like measure my lifespan in victories than than years. Um, and uh, you know, I’m maximizing uh… this is a hard question. Would you rather Corgi was a trillion dollar company but you died at 50 or it was a fail and you lived till you were 80? I mean I think the answer to that is pretty easy. Um because if I’m dying either way, you know, but for now life is short. Um we’ll see what happens.
Interviewer
If you’re going to be a hyper-growth startup and you’re not working weekends, you’re basically just quiet quitting.
Nico
Yeah, I strongly believe that. But you’re the only one doing it, aren’t you? I don’t know. If you visit very high growth AI companies, at least in San Francisco, um you know, the offices are pretty full on the weekends. Um and uh I don’t think it’s a coincidence.
Interviewer
You also have a chef seven days a week.
Nico
Not anymore.
Interviewer
Talk to me about that. Why did you decide to have a chef seven days a week and why do you not now?
Nico
Yeah, so um I loved our chef. I thought she was really great. Um I think that just like ordering food is a little more um like logistically uh easy. Um I think having food in the office is actually important and um because otherwise people like lose a lot of time like going out and like getting food and like coming back. It’s just very inefficient 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 spending more time like doing that than you are doing something that’s high leverage. Um you know I really dislike the culture of like pampering everyone or like taking care of them as if you’re their parents. I think Google is like the worst of that. And that — that’s not the reason why we don’t have a chef anymore. Um I think that sometimes doing more that’s not like core um can like lead to logistical burdens. Um, and it’s better to focus your energy on things that directly or indirectly lead to growth.
Interviewer
Why does Corgi have a cafe? You’re an insurance company.
Nico
Yeah. So um when we rented out our building in San Francisco, uh we needed to get signage on the side of the building and it was zoned or something. So, when we got um our primary floor, um we were forced to take over the retail space and it was like this empty barber shop. It was like really dingy like uh you know it’d been out of business for probably a couple years and uh so we moved in and you know everything was fine and um you know we have the sign on the side of the building great um but I’d walk in every day and I’d see this like empty barber shop and it would just piss me off cuz like I’m paying for that but like there’s nothing in it. Like it’s a waste of everything. Um, and um, at the same time, a huge complaint I have with San Francisco is that everything closes really early. Like it’s a big problem, especially in the financial district where our office is. 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, you know, 6:00 7:00 p.m. most days. Like things just — it’s a ridiculous uh situation. Um, clearly most restaurants don’t have a growth mindset. Um and like 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 um there’s not actually even in San Francisco, which is supposedly the center of technology for the world, um you know, there’s not a lot of places where people who are serious about that can come together and um you know, have a place where they can basically work hard. Um and yeah, we decided to just kind of impromptu — it wasn’t like a big planned out thing — um open up a 24/7 cafe and uh it caught on a lot more than we thought it would. Now it’s always full. There’s people signing term sheets and getting deals done. I can’t tell you — it was probably like over 20 people have told me like, “Oh, like I submitted my YC app at the Corgi Cafe and I got in” or something along those lines or I signed a term sheet there.
Interviewer
How much money did it take to start a cafe?
Nico
We spent under $100,000 opening it.
Interviewer
Has it been successful?
Nico
I mean, it’s always full. If you go there, you can go there at 3:00 a.m. And um I’d recommend writing term sheets to everyone there cuz they’re working hard. We lose money on the cafe without sponsorships. Um, because our drinks are sponsored — shout out to our drink sponsors. Um with that, um I think we’re probably slightly profitable.
Interviewer
Why are you bullish on London?
Nico
I think the talent is exceptional. Both British talent and European. And I think um 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. Um I think New York’s one of those places, although I don’t think that good companies tend to be in New York. And because of that um I think that there’s certain exceptional qualities that um London has. And um 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. Um, so we opened a London office before we opened a New York office. Like we’re very long London.
Interviewer
That said, you’re still super bullish on SF. Why?
Nico
I love San Francisco. I think San Francisco is a special place because particularly with people in the US, um, you know, 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 can, you know, if you’re a bit nerdy and if you love technology, you love programming, you love kind of these, um, maybe slightly unpopular sort of topics, um, then it’s a place where you can actually like find your people. And where like you’ll find yourself moving to and I think that’s a special quality. It’s almost like a you know a spiritual quality like you know everyone’s in an exile or something. Um and um and I think that’s something that’s like very unique. That’s why I think um New York is not a good place to have a company at all. Um the people that move their companies to New York uh do so because they want to date. Um and that’s the only real reason why they do. Um same with Miami or uh you know all of these other places. Um if you’re hardcore about startups and you’re American then I think you should go to San Francisco. Um oftentimes I mean there’s super great other cities like I do like Chicago and we have an office in Dallas that’s really great too. Um, and if you’re um, hardcore about startups outside of the United States, I think London is second to none as well. Um, although um, you got to avoid the pubs.
Interviewer
When you reflect on what you did that you wish you hadn’t done — what was the biggest?
Nico
I think if you dwell on mistakes then um then you’re like… I look more at the victories than than the losses because I think there’s more to learn from the victories and if you can kind of emulate the things that have worked really well um again and again.
Interviewer
What success have you studied and what do you learn from it?
Nico
I think that you need to look at the greats and the greats are oftentimes outside of the context of startups like you know people like you know obviously there’s there’s obvious like famous startup founders but I think that um you know looking at everyone from Alexander the Great to Napoleon to you know so on and so forth is also very informative um because if you want to like change the world if you want to do something important and you don’t want to just be like a mic copy of everyone else or you want to be class president or something that’s fine. But if you want to actually like do something big then um then I think that being a student of the greats is great and um you know the important thing I think is probably not copying them like you should have your own style but um but being a student of history is probably a pretty positive thing.
Interviewer
If I were to ask you what Corgi’s culture is in one word, what would you say?
Nico
We have a culture of winning. I maybe in the past I would have answered like exfounder, like hackers, like other things, but I think all that’s actually kind of fake and we just like winning.
Interviewer
Can you maintain the intensity that you have today when you’re at a thousand people?
Nico
Yeah, easy. I think so. There there’s there’s roles I think that creep in. You know you get the like a lawyer or an accountant are not going to work in the same way that um you know a software engineer might. Um and that’s just a fact of life. So okay so if they don’t want to work quite as hard then you just need to hire more of them for the same work output which is okay. Um it’s just like a return on investment calculation. The only reason I can think of is um you know there’s some point in which you need to take the off-ramp of 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 um don’t mind volatility — it’s something that I think can produce alpha in a lot of ways.
Interviewer
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?
Nico
I mean, we have plenty of parents that work at Corgi, so um life’s about trade-offs and sacrifices. Um 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. Um and that applies whether you’re married, whether you have kids, don’t have kids. Some of our best people have uh you know a lot of children. But if you want to you know clock in and then just check out of work then respectfully there’s infinite other jobs you can get and that’s okay. Um you know Corgi is not for everyone.
Interviewer
Do you care about the backlash that you get when you speak about this?
Nico
I get a lot of backlash. The death threats and the DMs. Uh you know people think I’m nuts. Not really. No. I don’t — I mean I think when you’re a young person, particularly I think uh young men, you know, don’t have um that much support within society. And I think it’s something of course that like weighs on people, particularly if you don’t have um you know, a lot of external validation or credibility yet. Credibility is something that um you know is hard to get. Um, which goes back to the crisis of legitimacy that I think is core to startups.
Interviewer
What are your lessons on paying people?
Nico
I think low cash comp is something good. Um, generally speaking, I think that like who ends up doing extremely well, like if people are doing well, you need to just like give them more like equity especially and uh 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 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 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 um no matter how much you pay people, you’re not going to retain them if they’re actually good. You know, I think you can probably split with any organization uh the team into three. You can have people that are like really good. Um people that are like, you know, kind of fungible and like mediocre and then people that are bad. And I think getting rid of the bad very quickly is important even if it makes a lot of noise.
Interviewer
You recently raised 1.3 from TCV. What are your single biggest lessons on fundraising?
Nico
Um, you know, I don’t know if I’m actually an expert there or anything like that. I think I’m all right at it. I’ve had to do it for years now. So, I think if you have to do anything for years, you get better at it. When I started, my pitch was not very good. I remember my first pitch. Um, you know, I took a red eye the night before. I had like, you know, my eyes were actually red. I looked like I was high or something. I was like so so nervous cuz we had to get $5 million and we had like 24 hours — I flew back on Thursday night. Um you know I was like oh we’ll get the money to you in a couple days like you know how the banks are. It’ll take some time to transfer the money. Um so I started pitching Friday. We had Saturday, Sunday and had to get the money by Monday. And um and you know I think the pitch was not very good honestly. It was 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.
Interviewer
What was the best VC meeting you had and what was the worst?
Nico
The worst are when it’s like super structured, 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 not that type of guy. Um, I think that the best ones tend to be when someone is like very like growth-minded or product minded and uh we just get to vibe about like where we’re going and and like how we’re going to win. Um, I’ve had some really bad ones. I’ve had people driving. I’ve had people flossing their teeth on the meeting, you know, like chowing down food like barbecue ribs or something where it’s like getting all over their face. I’ve seen it all. Um, I had one on 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.
Interviewer
What’s your biggest advice to founders on price?
Nico
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. Um I think that 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 um if something seems reasonable, I just stick with it. And uh you know, we could raise all of our rounds at higher prices, but we never do.
Interviewer
How long does it take to raise rounds for you?
Nico
Normally a couple days at most. Um if you’re in the market for a long time, it’s a bad thing. Maybe it’s a good thing for your 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 start to optimize for like selling equity instead of like selling your goods and services. Um, and fundraising is like super distracting. Good companies get deals done. And um and I think that you know a venture capital firm um it’s a lot of things. It’s a brand. It’s a company and um you know good companies get deals done and I think that applies to to venture capital firms too. Some deals um you know are made in in times of crisis. Um I think the the venture deals that I respect most of all are the ones that I hear about from funds where their company was not doing well at all and um 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. And uh the amount of courage it takes to do like something where the company might be contentious or controversial or the metrics might be going in the wrong direction — that type of uh behavior, I think, is is hard and um and I think doing the hard thing in venture is uh is rare, unfortunately.
Interviewer
You can buy OpenAI or Anthropic today, both at the same price of 900. Which one do you choose?
Nico
Yeah, I’m going to get in trouble for this probably, but um the disclaimer is um this might be a stated preference versus a revealed preference. Um given that we spend maybe like $400,000 per month on Anthropic and $0 on OpenAI at the moment. Um but I think that like spiritually like OpenAI is um I guess a little more pure um because they kind of created you know this idea of like an AI lab as a company um dating all the way back to YC Research and um you know Anthropic is a result of you know employees that didn’t like the management or the direction there were complaints about profit and ethics and all this other stuff and um and you know the EA movement and all of that. And um you know I think when your origins are um that impure it’s a little hard to overtake the king and uh you know right now um Anthropic frankly speaking has been out-executing OpenAI. Their product’s much better. Um you know we use the best product in every category at least from a from an enterprise or like workflow automation perspective. Anthropic is better. So OpenAI needs to lock in.
Interviewer
What is no one talking about that you’re spending more and more time thinking about?
Nico
To me, there’s good companies and there’s, you know, everyone else. And, um, I think the number of good companies is very small. And a good company wants to win is like world historic, will 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, you know, and that’s okay. Like, it’s okay to be average and part of the mediocre masses or whatever. That’s all right. Um, but I think that the kind of uh cultural um, or internal um, kind of character of the companies that are good companies, um, is something that’s not appreciated enough. like from a from a you know a metaphysical level there’s a really big difference between Andreessen and like Anthropic right those are like super different companies and um I think both those could be good companies um but I don’t think people really understand um the philosophy behind um the management teams that they’re investing in.
Interviewer
What are you most excited for when you look forward to the next ten years?
Nico
It’s a little hard to say because if you ask that ten years ago um the technology that people were really excited about didn’t exist yet, right? Um it was only late 2022 that people actually started getting uh with ChatGPT 3.5 that large language models were obviously very important and very exciting. I think like within the next ten years, technology will solve a lot of problems. Perhaps it’ll create some too, but I think it’ll solve a lot more than it creates. And I think that there’s certain areas where venture investing hasn’t worked before where um where there could be like category defining um outcomes and where there could be um you know new uh kind of industries where where smart people are actually interested in going into um like biology is one that comes to mind. Um, and um, I really strongly believe that um, you know, we’re gonna probably see more like ChatGPT moments um, you know, maybe a couple years from now that uh, that will really shake things up.
Interviewer
Dude, I have to say it’s been so wonderful having you on the show. Thank you so much for joining me today, man.
Nico
Thanks for having me.