The Hardest Working Startup in America | Nico Laqua, Co-founder & CEO @ Corgi

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 is probably 3 to 4 hours.

So, you literally live in the office.

Yeah, I have a mattress there.

Would you rather Corgi was a trillion-dollar company, but you died at 50, or it was a failure and you lived until you were 80?

I mean, I think the answer to that is pretty easy.

Welcome to Corgi Insurance, the most insane workplace culture in America. Joining me in the hot seat today is their co-founder and CEO, Nico, who just closed their latest funding round, valuing them at a whopping $2.5 billion.

Yeah, I mean, I get a lot of backlash. I get death threats and DMs. People think I'm nuts. I think the number of good companies is very small.

Ready to go. Nico, dude, I am so excited for this. I was more excited, I have to admit, for this than I am for almost any other show, because, one, I think we align, and, two, I think we align on something that's rather different. Thank you for joining me, dude.

Yeah, thanks for having me.

1. Fear of Losing vs Hunger to Win

I'm often struck by great CEOs. What is it that motivates you? Is it the fear of losing, or is it the thrill of winning?

I think you can't be afraid of losses. Losses are beautiful because you can have asymmetric upside with winning. I think you have to love winning, and you have to love the victories.

Jeff Bezos said something a number of years ago that has always really stuck with me. He gave it as a baseball analogy, which I guess is very American. In baseball, there are 3 bases and home plate, but you can score a maximum of 4 runs when you're at bat. If you go up to bat and every single time you swing, you try to 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 have a maximum of 4 runs, but your probability of striking out or scoring nothing is quite high.

In business, it doesn't quite work like that, because instead of 4 runs resulting from a home run, a home run might actually result in infinite upside. It might result in something like AWS popping out of nowhere. I really think seeking asymmetric upside—or infinite, uncapped upside—with capped downside is the core of business, and taking a lot of shots on goal.

If you look at people who started important things, not every single thing they did worked. Napoleon was the best general of all time, but he didn't win every single battle. He won more battles than average, certainly more than most other generals. I don't know. I think the fear of losing can't really motivate you, because otherwise you just become this creature afraid of doing anything.

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 shit 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?

2. Going to University Was My Biggest Mistake

I think going to university was a big mistake.

Why?

If you want to do big things, you need to go out in the wilderness a little bit and be humbled. You need to metaphorically get beat up. You need to go through the lows before you go through the highs. I wasted some amount of time in my life doing that, for sure.

Do you think university carries less weight than ever today?

I don't know if it carries less weight or more weight. I don't really think about that, because you make your own weight in life.

It's an interesting point, because startups are fundamentally, I think, about a crisis of legitimacy. That was a big problem in the Roman Empire, right? 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 replace them with the next guy.

I think startups are a little bit like that, where there's no inherent loyalty. There's no reason to work for this company or that company. There are no blood ties, there's no inherited structure, and you can just go out and make your own.

The process of going through a company is just building that legitimacy. 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. Universities, I suppose, are meant to give you a credential that carries some legitimacy; otherwise, you wouldn't do it. You can learn all the material online. You can learn all the material with an LLM 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 and on the nose.

It almost reminds me of Marc Andreessen, where he says, essentially, that 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, when it transitions and Corgi then loans the brand to Kanye or to J.D. at TCV. It's the other way around. Do you see what I mean? It's the legitimacy of a brand.

Yeah. He also says, "Do you want to be liked, or do you want to win?"

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.

Why is he saying that?

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. That'd be very unusual.

But now 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 this company or that company, with the descriptor being its investors. That's meant to signify something about the way that the company acts or ought to be.

It's a bit unusual, because people will say that out of one side of their mouth, and out of the other side of their mouth they'll acknowledge that when they invest in companies, they can't do anything about their investment. If the team is incompetent or making bad decisions, that's a really hard thing to solve.

No, that is 100% true. I have to ask you: you said there, "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 7 days a week at the company, and the company is expected to work 7 days a week.

Yeah.

Can you help me understand why that is and how you thought through that as a decision?

3. Working 7 Days a Week

If you're solving the most important problems, or if you want to dream big and scale up your ambition, let's presuppose that you want to do something big and not small. Whatever you can get done in 5 days, I promise you you'll get more done in 6 and 7, and so on and so forth.

I think that 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 you want to have brothers and sisters in arms with the people you're working with, then you should go all out. You shouldn't half-ass it for 5 days. Why not 4 or 3 or 2 or 1? I think if you're doing something, you should do it properly.

Do you not believe in the benefits of rest? I'm 100% with you on the work ethic, and I do actually think having a day off can be helpful. Don't you think that rest carries benefits?

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—

But they wouldn't have a place at Corgi.

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.

Dude, how does that go down in hiring? I would love to be able to do that. You could say, "Harry, you could do that."

4. How Work Trials Filter Out the Wrong People

You can just say it and say, "Why?" Because we want to build the biggest thing ever. If you want to build the biggest thing ever, you need to win. If you want to win, then it's actually something that I think attracts the right type of person and absolutely repels the wrong type of person.

Particularly for young people, I think there's a lot of people who 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. If you want to be a winner, if you want to be a killer, then, sure, you can do that for 30 minutes a day. But I think doing it all the time is better.

Do you have people who turn up to interview processes and think that's kind of it, but don't realize the intensity?

Yeah, we have everyone do work trials, so that scares some off.

What do you mean, work trials? I think it's really important that people know what they're getting into on both sides. Before people come in, we really like to have them do mock work for 1 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.

That's a benefit of actually working weekends: people can do it in their jobs without taking time off. It does make it easy to poach. What in a work trial impresses you most versus turns you off most? Because it is tough in a trial to have much impact; you're onboarding and whatever.

Yeah, the soft skills matter more than the hard skills for me. If someone really wants it, if they're all-in and if they want to 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 place for someone like that.

It might not be exactly what they're applying for, or what they think they're going to be doing. But I think you should just solve hard problems. You should do hard things. You can tell if someone's into that or if they're into checking in and checking out.

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 don't necessarily mind. That normally comes from a certain place, I think. To me, that answer would normally 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 think that being extremely money-motivated leads you to short-term local minimums and local maximums that don't actually result in the most money being made.

What is your answer to that? If it's not the money—we were chatting earlier, and your sacrifice is unwavering to this business. We'll get on to more of it. What is the reason if it's not money?

I want to build the most important company in the world. I want to win. I admire the greats. I very much want to join them.

I think that, as people living in this time and circumstance, we're subject to the world-historical conditions in which we're in. If we were alive 200 years ago, we'd probably be generals, fighting some sort of wars or something. That would be very simple. The winning would just mean killing your enemies, and unfortunately, you can't do that anymore.

So I think the next best thing, and where we're at now, is that you can actually, in a positive-sum way, make a really big difference in the world. I want us to always be solving the hardest problems possible, and I want to win. I want to add value.

5. Why Nico Wants to Build the Most Important Company in the World

I heard from one of your investors that you live in the office.

Yeah.

What does that look like? Do you actually live in the office?

6. He Actually Lives in the Office

Yeah. I think it's one thing to say, “Why don't you guys work 7 days a week?” while you're on some yacht somewhere, hanging out, or at a villa or something. It's another thing if you're actually putting in the work.

I think symbols often really matter. The cosmetic stuff, like having a sign on the building—

We're going to get to the sign, didn't we?

Yeah. The cosmetic stuff—I think it does matter. Symbolism matters. There's a reason why governments and religions, and all of the really important things, tend to care a lot about symbols. The flag's very important and all that.

I think the symbolism around working hard is quite different: leading the troops from the front line versus saying, “Why don't you guys work hard, and I won't?”

So you literally live in the office.

Yeah. I have a mattress there and that sort of thing. I don't spend every single night there anymore because I used to shower only at the Equinox 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 San Francisco office. Our London office actually has a shower.

Yeah, I had this in the founders' room. Is that what it's called?

Some people have called it that, but normally people just say, “Oh, it's Nico's room.”

I've got founders' room showers at Equinox. It works every waking hour. How long do you sleep for?

I don't sleep a lot. I think the average night is a couple of hours, probably 3 to 4 hours, but some nights I really do make an effort to try to sleep a little more—

Have you ever had health scares?

Candidly, I give everything to this. I have psoriasis, and I had heart palpitations because I was just so all-in, and I still am, but I do have to monitor my sleep. Actually, it's the one thing I really—

Yeah, I think sleep is important, and I encourage people to sleep a lot.

I don't know. I think I would rather measure my lifespan in victories than years.

This is a hard question. Would you rather Corgi was a trillion-dollar company but you died at 50, or it was a failure and you lived till you were 80?

I think the answer to that is pretty easy. If I'm dying either way, 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 where they say, “Would you rather live 10 years less but have a gold medal?” Ninety-eight percent of them said, unwaveringly, yes.

You need to want it, and that's presupposing that death is coming either way, which you never know.

Bryan Johnson has his way. You said if you're going to be a hyper-growth 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. If you visit very high-growth AI companies, at least in San Francisco, the offices are pretty full-on on the weekends. I don't think it's a coincidence.

It's easy to look at this—and people will—and go, “It's so unfair, harsh.” You also have a chef 7 days a week.

Not anymore.

Okay. Talk to me about that. Why did you decide to have a chef 7 days a week, and why do you not now?

I loved our chef. I thought she was really great. I think that just ordering food is a little more logistically easy.

I think having food in the office is actually important because otherwise people lose a lot of time going out, getting food, and coming back. It's just very inefficient, and people need to think about where they're going to buy the food. It's just extra cognitive load. You're spending more time doing that than you are doing something that's high leverage.

I really dislike the culture of pampering everyone or taking care of them as if you're their parents. I think Google is the worst of that.

Did it feel like you were pampering them when you had a chef 7 days a week?

Maybe a little bit. But that's not the reason why we don't have a chef anymore.

Why don't you have a chef anymore?

I think we really liked the idea of having a chef. Again, the chef we got was awesome. I really liked having her.

But sometimes doing more that's not core can lead to logistical burdens, and it's better to focus your energy on things that directly lead to growth.

Or indirectly lead to growth.

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 sure it's not related. It's a San Francisco company.’” She's a lawyer in London. And she was like, “No, no, it's the same one: cafe expansion head.”

It seems to me—cafe? Why? You're an insurance company.

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. When we got our primary floor, we were forced to take over the retail space, and it was this empty barbershop.

It was really dingy. It had been out of business for probably a couple of years, and so we moved in. Everything was fine, and we had the sign on the side of the building, great, but I'd walk in every day and see this empty barbershop, and it would just piss me off because I'm paying for that, but there's nothing in it.

It’s a waste of everything. At the same time, a huge complaint I have with San Francisco is that everything closes really early. It’s a big problem, especially in the Financial District, where our office is. There are a lot of really great startups that want to push themselves hard, but you cannot find a café. You can’t even find a place to eat past 6:00 or 7:00 p.m. most days. Things just are—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 who are serious about technology, about building things, about starting things, there aren’t actually—even in San Francisco, which is supposedly the center of technology for the world—a lot of places where people who are serious about that can come together and have a place where they can basically work hard.

We decided to just, impromptu—it wasn’t like a big planned-out thing—open up a 24/7 café, and it caught on a lot more than we thought it would. Now it’s always full. There are people signing term sheets and getting deals done.

How much money did it take to start a café? Spent under $100,000 opening it. Has it been successful?

It’s always full. If you go there, you can go there at 3:00 a.m. I’d recommend writing term sheets to everyone there because they’re working hard. I can’t tell you—probably more than 20 people have told me, “I submitted my YC application at the Corgi Café and I got in,” or something along those lines, or, “I signed a term sheet there.”

Or, “You should do Corgi Ventures,” which operates from 3:00 a.m. to 5:00 a.m. It’s those founders that are there.

Yeah. The problem is, if anything becomes a measure of success, then it ceases to be a good measure once other people know. The alpha disappears very quickly.

I totally get you.

Does it make money?

We lose money on the café with sponsorships because our drinks are sponsored. Shout-out to our drink sponsors.

You have Brex here?

We have Brex. We have Deel. We have a couple of them.

What, a Deel sponsor?

It’s the Deel Speed. It’s a smoothie.

Oh, I like that. Yeah, fair enough. Deel. Love Deel Speed.

With that, I think we’re probably slightly profitable.

If I was an investor, I’d say, “Nico, I love you, dude. I love the energy. This is a distraction.”

Yeah, they hated it at first.

Why are you doing a café expansion?

You sound exactly like our investors. I got a ton of calls and texts that said that before it opened.

Oh, no, no, no. I did, I promise.

I’ve learned that you don’t get any credit ever criticizing a founder.

So I just don’t. You know what I do, bro? Dude, I’m here for you. Well done.

7. Why London Could Become the Center of AI Outside the US

Our investors didn’t get the memo, so I heard plenty of that.

But, dude, why are you doing it? I get it in San Francisco. Cool. You’re opening in London.

We have an office in London. I think I’m very bullish on London, actually, in general.

Why are you bullish on London?

I think the talent is exceptional, both British talent and European. There are very few places in the world where, if you tell someone pretty much anywhere to move to, they’re very happy to do so. I think San Francisco is one of those places. I think New York is one of those places, although I don’t think that good companies tend to be in New York.

Because of that, I think there are certain exceptional qualities that London has. Given the whole visa situation in the United States, I think there’s actually a phenomenal opportunity for London to become a center of AI and a center of tech.

We opened a London office before we opened a New York office. We’re very long London.

Do you find it much cheaper to hire in London?

It’s a little bit cheaper. Maybe we’re paying above market, but we’re not paying that much. The thing is, if you’re working for a salary at Corgi, you’re doing something wrong. If you’re super hyped about your cash compensation, then you’re probably doing something wrong.

Are you more generous than others on equity because you understand that you are asking for more of someone’s life by requiring 7 days per week?

Yeah, we’re generous with top-ups.

What’s top-ups?

After people are working, we give more equity based upon performance. That’s where we’re more generous than the initial equity that people sign on with.

Okay. So it’s like accelerators on milestones hit.

Yeah. It’s a little more ad hoc than that, but, yeah, something like that.

I love it. We said something about distractions. A lot of founders angel invest. How do you think about founders actively angel investing?

I don’t angel invest.

Why?

I think it’s a distraction. I don’t think it’s core to winning.

Have you sold secondaries?

No, I haven’t sold any secondary. People are always trying to buy them, but I’ve yet to sell a single secondary.

Why is that?

Because our equity is going up—or maybe I shouldn’t say that—but I believe our equity is going up, and I’m voting with my feet. If I have, 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, why would I sell that? I don’t really have a reason to.

You don’t have huge rent to pay. That’s for sure.

Yeah, that’s true.

I love that. Despite the bullishness on London, you’re still super bullish on San Francisco.

Yeah, I love San Francisco.

Why is the amount of great talent building in San Francisco? Is it just that there’s nothing else to do there?

That might be part of it, which is maybe a bit of a problem that London has. Things are actually open later in London, and there are more people about. There are too many pubs. That might be a problem. It’s a lot of pubs.

There are a lot of pubs. Do you drink?

No, I don’t drink.

Okay.

I think San Francisco is a special place because, particularly with people in the US, if you want to do something big with your life and you’re not quite sure where to go, San Francisco is an end destination. If you’re a bit nerdy, you love technology, you love programming, you love these perhaps slightly unpopular topics, then it’s a place where you can often find your people and where you’ll find yourself moving to.

I think that’s a special quality. It’s almost like a spiritual quality, like everyone’s in exile or something. I think that’s something that’s very unique, and that’s why I think New York is not a good place to have a company at all.

The people who move their companies to New York do so because they want to date. That’s the only real reason why they do. Same with Miami or all these other places. If you’re hardcore about startups and you’re American, I think you should go to San Francisco.

There are other super-great cities. I do like Chicago, and we have an office in Dallas that’s really great, too. If you’re hardcore about startups outside of the United States, I think London is second to none as well. Although you’ve got to avoid the pubs. The pubs are really getting it.

8. Learning From the Greats: Napoleon, Alexander & Startup Culture

I get you. We’ve spoken a lot about everything from chefs to signage on buildings to Corgi Café to work ethic. You’re a little bit younger than me, but I do reflect on how I’ve built the company. When you reflect on what you did that you wish you hadn’t done, I mean, there’s a long list there.

What was the biggest?

I don’t dwell on mistakes.

How very Marc Andreessen of you.

Yeah. I look more at the victories than the losses because I think there’s more to learn from the victories. If you can emulate the things that have worked really well again and again—

There’s a brilliant commencement speech by Matthew McConaughey at the University of Texas or the University of Houston. He says, “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 often outside of the context of startups. There are obvious famous startup founders, but I think looking at everyone from Alexander the Great to Napoleon, so on and so forth, is also very informative.

If you want to change the world, if you want to do something important, and you don’t want to just be a me-too copy of everyone else, or you want to be class president or something, that’s fine.

But if you want to actually do something big, then I think that being a student of the greats is great. The important thing, I think, is probably not copying them—you should have your own style—but being a student of history is probably a pretty positive thing.

If I were to ask you what Corgi’s culture is in 1 word, what would you say it is?

We have a culture of winning.

Winning. That’s it.

That’s it. Okay. Maybe in the past I would have answered ex-founders, hackers, other things, but I think all that’s actually kind of fake, and we just like winning.

How big is the team?

Maybe a bit over 100 now.

Can you maintain the intensity that you have today when you’re at 1,000 people?

Yeah, easy.

Really?

I think so.

Why has no one else been able to do it?

Naturally, there are roles that creep in. You get a lawyer or an accountant, who are not going to work in the same way that a software engineer might. That’s just a fact of life. 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. It’s just a return-on-investment calculation.

The only reason I can think of is that there’s some point at which you need to take the off-ramp from being super hardcore and accept maybe lower growth but less volatility. I personally, at least at the current stage I’m at, don’t mind volatility. It’s something that I think can produce alpha in a lot of ways.

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?

9. Is It Possible to Stay This Intense at 1,000 People?

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 and the social life attached to your workplace, if you want your work to be additive to your life as opposed to separate, then it’s a great place to work.

That applies whether you’re married, whether you have kids or don’t have kids. Some of our best people have a lot of children. But if you want to clock in and then just check out of work, then, respectfully, there are infinite other jobs you can get, and that’s okay. Corgi is not for everyone.

Do you care about the backlash that you get when you speak about this?

I get a lot of backlash. Yeah, I get a lot of backlash—the death threats and the DMs. People think I’m nuts.

Do you care?

Not really. No, I don’t. Have you ever had that?

Yeah. I don’t know. I think when you’re a young person, particularly young men, you don’t have that much support within society. I think it’s something that, of course, weighs on people, particularly if you don’t have a lot of external validation or credibility yet. Credibility is something that’s hard to get, which goes back to the crisis of legitimacy that I think is core to startups.

Do you think you’re legitimate yet? I know that sounds strange.

Probably. We’re more regulated than a bank, we make a lot of revenue, and we’ve raised money. I don’t think we’re quite legit yet. I think we’re getting there.

I think you’re legitimate when you’re in a position where you don’t get fired for buying IBM. In my context as a fund, if you’re Andreessen or—you name these great, big, large platforms—you don’t get fired as an LP for doing it, right?

You can’t. Period. Yeah, that’s probably exactly right. In the fund context, Andreessen, Kleiner, or even Sequoia back in the day, at some point they were just a couple of guys in some shitty room who didn’t really know what they were doing and were making it up as they went along.

They were probably pointing at—or, not probably, they certainly were pointing at—other people and saying, “One day we’ll be legit like them, and the institutional LPs will take us seriously.” There’s always more legitimacy, right? You can go from pension funds to university endowments to the government. That’s the ultimate form of legitimacy, probably because the government can just take people’s money.

What are your lessons on paying people? 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 or benchmarking comp?

I think low cash comp is something good. Generally speaking, if people are doing well, you need to give them more equity, especially, and make it so that if they’re doing a very simple return-on-investment calculation, the highest-EV thing they can do is work in their current role.

If you can’t provide that upside, there’s no reason for them to continue working super hard. They should be doing something else, whether that’s working for someone else, starting their own thing, or whatever.

Separate from the comp and the simple EV calculation, you need to actually be solving big problems. 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 the team in any organization into 3 groups. You can have people that are really good, people that are fungible and mediocre, and people that are bad. Getting rid of the bad very quickly is important, even if it makes a lot of noise.

Do you keep the mediocre?

I wouldn’t put it like that, but I think in any organization there are people that you wouldn’t be devastated if they left.

It’s a brilliant question. The question I always ask is: knowing what you know now, would you hire them again? It’s the most important question.

Yeah. There are a lot of people where the answer might be yes, but you’re not going to be sobbing and punching the wall if they’re no longer with you.

Fundraising is a big part of your job as a CEO. You recently raised, I think, 1.5.

Yeah, 1.3.

10. Raising $150M: What Nico Looks for in Investors

1.3 from TCV. I love TCV. I love John Doran. I spoke to him before the show. What are your single biggest lessons on fundraising, having raised across pre-regulated and post-regulated stages, with revenue scaling very fast? What are the most non-obvious lessons you have from raising several hundred million?

I don’t know if I’m actually an expert there or anything like that.

Do you think you’re a good fundraiser?

I think I’m all right at it. I’ve had to do it for years now.

What do you know now that you wish you’d known when you started?

When I started, my pitch was not very good. I remember my first pitch. I took a red-eye the night before, and my eyes were actually red. I looked like I was high or something. I was so nervous because we had to get $5 million, and we had 24 hours.

I flew back on Thursday night. I was thinking, “Oh, we’ll get the money to you in a couple of days. You know how the banks are. It’ll take some time to transfer the money.” I started pitching on Friday. We had Saturday and Sunday, and we had to get the money by Monday.

I think the pitch was not very good, honestly. It was a lot of, “Just trust me.” I wasn’t telling them the name of the insurance carrier because I was afraid they’d call them and ruin it. I think the first set of pitches I did weren’t that good.

My first pitch for Corgi, I think, was maybe First Round Capital. Who was my first pitch? Probably First Round Capital was my first pitch from way back in the day. The very first VC I ever talked to was at Google Ventures.

You were raising 2 on 10.

We were raising 5 on 28 with that one. That was 2024, so that wasn’t super easy.

That was recently. It was like 2 years ago.

Yeah.

What was the best VC meeting you had?

The worst are when it’s super structured, when they start asking me BS about our balance sheet or get into the nitty-gritty. I’m not that type of guy.

The best ones tend to be when someone is very growth-minded or product-minded, and we just get to vibe about where we’re going and how we’re going to 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 going to put them on the spot because they might invest later on.

Ah, okay. What was the worst?

Oh, I’ve had some really bad ones.

Have you had some worse?

I’ve had people, especially the first-round, early-stage investors, who are disrespectful. I’ve had people driving. I’ve had people flossing their teeth in the meeting, chowing down on barbecue ribs or something, with it getting all over their face.

I've seen it all.

What do you say? I'm like, “Please finish flossing. It's okay.”

Yeah, I had one on FaceTime where the guy was hitting his vape, and I thought he was asleep because he just had his eyes closed, leaning against the wall. I've had some crazy pitches, particularly at the early stage.

What is your biggest advice to founders on price?

Price is a difficult one. Brian Chesky told me one time to never take the highest price, and I've taken that to heart. We never take the highest price, ever. I think that's just a good rule of thumb. We always go with the second- or third-highest price.

I don't do a lot of negotiating on price. I just see where the market's at, and if something seems reasonable, I stick with it. We could raise all of our rounds at higher prices, but we never do.

How long does it take to raise rounds for you, normally?

A couple of days at most. 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 for the funds you're raising from, but I think it's a bad thing for the company because you start to optimize for selling equity instead of selling your goods and services.

Fundraising is super distracting. It's not quite as bad as audits after you get the term sheet, but it is pretty distracting.

A 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 fundraising process with you either, but I do want to get to know you, and I do want you to know me.”

Well, VCs always say that, but the thing is, they could put in the work to get to know you, but they never do. I think that—

I don't know. Again, this is interesting because we're totally on the other side of the table. We try, and you know what we get? “Thanks so much for your email. We're heads down.” Yeah.

I'm heads up, because if you're working on an important deal that's going to double your revenue, the last thing you want to do is meet with some VC.

I get it. But help me understand.

You know what an investor told me one time? He said, “Good companies get deals done.” At first, I was mad. I was pissed to hear that. It was like a backhanded compliment. 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.

I've actually taken it to heart because I think it's true. Good companies do get deals done. Since then, we've shifted our approach and started getting deals done. We've stopped being such absolutists, and we move with haste. Time kills all deals, and as a company, we get deals done. That's the key.

I think a venture capital firm is a lot of things. It's a brand, maybe a lifestyle business, but one thing it certainly is, is a company. Good companies get deals done, and I think that applies to venture capital firms, too.

Some deals are made in times of crisis. I think the venture deals that I respect most of all are the ones that I hear about from my funds, where the company was not doing well at all and a VC came in and saved them. The amount of gratitude that founders have for something like that is extreme.

The amount of courage it takes to do something where the company might be contentious or controversial, or the metrics might be going in the wrong direction, not the right direction—that type of behavior is hard. I think doing the hard thing in venture is rare, unfortunately.

But genuinely, then, you would rather do a deal with someone you don't really know if it's in a few days?

I mean, one thing I know about them is that they can get deals done quickly.

Right? But they can also be bad.

That's true. I've had plenty of bad investors in my life. A bad investor is much worse than no investor, and it's hard to get rid of them.

The thing is, if you're doing well, pricing your company cheaply, and you go out to market, you can get a deal done very quickly. It's just a fact. Why would you waste time doing that?

Do you think you price your company cheaply?

Yeah, we price all our deals cheaply.

Why?

People might not think that when they see our stuff posted, but every round that we raise, we could raise at a higher valuation. I'm very sure of that.

Are you not doing a disservice to your existing investors by not pricing it higher?

I don't think so. They all got good deals, too.

If we were a public company, we'd probably be worth less, because the public markets don't know how to evaluate high growth or potential.

Well, talk to me about that.

Look at the financial services companies on the public markets. They're all terrible. They don't grow, but they're good for—

So are they mispriced, or are they actually accurately priced because they don't grow and they have poor margins?

I mean, some of them have good margins. They make money. I think that private markets feel to me like a vehicle for valuing growth, whereas public markets feel like a vehicle for valuing cash flow. In the past, we'd call those dividend stocks.

Maybe that's not so favorable if you're looking for asymmetric upside and are an investor, because you don't have access to private deals as much. But certainly, from a company perspective—

Do you not think, at some point, all companies are an embodiment of their future free cash flow? That is what a company valuation is.

There's certainly value in it, but no, I don't think so, because maybe at some terminal point, from a theoretical perspective. But a brand is worth something, and identity is worth something. Why do you buy a Rolex watch instead of a Chinese copy of a Rolex watch? They might be made of the same materials, or the same whatever. Both tell the time.

If I gave you unlimited money, what would you do that you're not doing today? For example, I'd be on the side of an F1 car. I would be opening Japan.

If you had unlimited money, I think you'd have bigger things to do than be on the side of an F1 car. Right? But there are a lot of things I'd love to do.

Within the context of Corgi, every single super-regulated financial institution, where right now it's run on fax machines and by boomers, we'd like to make those not waste people's time and charge lower fees. We'd like to make everything a little more protected, a little more efficient, and a little more profitable.

Outside of that context, I'm a techno-optimist. 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 mostly a bet on the most regulated sectors, but I think there are very few problems that technology can't solve.

There are probably a lot of areas that are exciting, like medicine and mental health. There are crises in a lot of concurrent areas where I think technology can make things a lot better.

What role do we not have today that you think we will have and that will be very commonplace in 5 years' time?

11. AI Makes Sales & Marketing More Important, Not Less

I don't know if it's a role in particular, but I think that AI actually makes sales and marketing much more important than they were in the past. In the past, if you had a really rock-solid, super-hardcore engineering and product team, you could come out with something that would blow everyone away. It would be faster; it would be better.

Now, you can make something faster and better, but if you don't have people to sell it, market it, or tell people that it exists, it's not really worth a whole lot. I think the organic network effects around, particularly, B2B product launches just don't really exist in the same way that they used to.

Do you think traditional B2B marketing is good?

I think traditional B2B sales is good. I think marketing is awful.

Why?

There's a lot that B2B could learn from consumer. Conferences are not it. I'm not a fan of going and hanging out with a bunch of sweaty people in a room. I don't really like that.

I think consumer companies have perfected marketing, and B2B companies have perfected sales. Much like in a company where you have a dominant product, that kind of becomes the company, and it's hard to really care that much about auxiliary revenue streams.

As an industry, if you're selling B2B products, you're going to get very good at sales, and marketing will tend to be an afterthought in most instances.

I do want to move into a quick-fire, where I say a short statement and 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 12 months?

There’s a lot I’ve changed my mind on. I think I’ve grown to value experience a lot more. In the past, I’ve probably made certain statements about boomers being slow and bad, and I’ve definitely undervalued people who have been doing something for a long time.

A lot of times, there are little nuances or edge cases that, when you do something for a long time, you pick up. 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 the older generations, especially the retiring ones.

I think it’s a big problem because there are trillions of dollars to be made by getting that knowledge out and putting it inside computers that can think and talk. I don’t think I viewed those problems through that lens. I just considered old people using fax machines and moving at 2 miles per hour to be 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?

12. Boards Are Mostly Theatrical

I believe in executive decision-making. Our board’s great, and yada yada yada—all the disclaimers—but I think you just need to be able to decide. You need to be able to do things.

Do you think Elon Musk or Mark Zuckerberg care what their board thinks? Do you think they’re like, “All right, guys, let’s huddle up. Let’s make a decision”? Every committee decision, I think, is BS. 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.

Is the board a check-the-box exercise?

I think so, a little bit. It’s a little theatrical. I guess it’s good to make sure you’re not a scam or doing blatantly illegal stuff, but if management is unethical or unscrupulous enough to scam people or do illegal stuff, then they’re going to do it anyway, probably with or without a board. That’s a management problem.

You can buy OpenAI or Anthropic today, both at the same price of 900. Which one do you choose?

13. OpenAI vs. Anthropic

Yeah, I’m going to get in trouble for this, probably. The disclaimer is that this might be a stated preference versus a revealed preference, given that we spend maybe $400,000 per month on Anthropic and $0 on OpenAI at the moment.

I think that, spiritually, OpenAI is a little more pure because they created this idea of an AI lab as a company, dating all the way back to YC Research. Anthropic is a result of employees who didn’t like the management or the direction there. There were complaints about profit and ethics and all this other stuff, as well as the EA movement and all of that.

I think when your origins are that impure, it’s a little hard to overtake the king. Right now, frankly speaking, Anthropic has been out-executing OpenAI. Their product’s much better. We use the best product in every category, at least from an enterprise or workflow automation perspective, and Anthropic is better. So OpenAI needs to lock in.

How easy is it for you to switch back?

I don’t think it’d be that hard. Although all of the labs are always trying to make us sign contracts, if they give us a big enough discount on tokens, then we’d consider it.

What is no one talking about that you’re spending more and more time thinking about?

To me, there are good companies, and there’s everyone else. I think the number of good companies is very small. A good company wants to win. It’s world-historic and will be talked about in 100 years. There are just not many of those companies because people don’t want to win. They don’t want to put in the work.

That’s okay. It’s okay to be average and part of the mediocre masses or whatever. That’s all right. But I think the internal character of good companies is something that’s not appreciated enough.

At a metaphysical level, there’s a really big difference between Andreal and Anthropic. Those are super different companies, and I think both of those could be good companies. But I don’t think people really understand the philosophy behind the management teams they’re investing in.

Who do you think is the most underappreciated CEO? When you look at your style, who most aligns with your style?

My style is my own style. I try to just do me.

I think there are plenty of super-underappreciated CEOs. One area where I think, more than venture-backed companies, I would love to see more of is venture funds speaking out about these sorts of important topics.

I know startup founders love to clown on VCs for chiming in about topics they might not know a lot about, but I think venture funds are actually in a really strong position to influence the way the startup ecosystem looks. Despite the fact that they need to raise from LPs, and LPs can crack the whip or whatever, they’re setting the incentives, and incentives often drive behavior.

I would love to see the CEOs or the people running venture funds actually take a more active stance in aligning their deployed capital with the changes they would like to see in the world. To me, that’s perhaps a more important issue than any particular company’s CEO or management team, broadly speaking.

14. Are VCs Responsible for the Rise in Startup Fraud?

Would you blame VCs for the dramatic increase we’ve seen in fraud, especially around ARR? We put so much emphasis on going from $0 to $100 million in X amount of time.

Yeah, the founders lie.

I think a lot of the issues with fraud we’ve seen are downstream of credentialism, or that quest for legitimacy, in a lot of ways. I’m not going to speak about specific frauds, but I’m sure some come to mind that check those boxes.

I think VCs are partially responsible, but as a venture investor, after you invest in a company, there’s very little you can do. If management is unethical or unscrupulous enough to scam people or do illegal stuff, or the product doesn’t actually work, I don’t think you’re really responsible for that management team committing fraud.

On the extreme, if you go back 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. Basically, they’d be arbitraging that and pumping the tokens or whatever. In hindsight, I guess that was the wrong type of tokens to work on.

I think people blaming YC or whatever for some of their companies being frauds is probably not directionally correct. Internally, it’s not like any venture fund really wants to invest in a fraud. People who are doing these things are very good at wrapping them up and disguising them in such a way that they’ll pass muster, especially if a round is moving quickly, which most good companies’ rounds do.

Who was your first believer with Corgi?

It was probably Jared Friedman from YC. There have been times when he was our only believer. Everyone else was a doubter, a naysayer. But Jared has always been there for us.

Would you do YC again?

Yeah, I’d do it again.

Final thing for you: What are you most excited about when you look forward to the next 10 years? What are you thinking, “This, I can’t wait for”?

It’s a little hard to say because if you had asked me that 10 years ago, the technology people were really excited about didn’t exist yet. It was only in late 2022, with ChatGPT 3.5, that people started to see that large language models were obviously very important and very exciting.

I think within the next 10 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. There are certain areas where venture investing hasn’t worked before where there could be category-defining outcomes, and where there could be new industries that smart people are actually interested in going into. Biology is one that comes to mind.

I really strongly believe that we’re going to see more ChatGPT moments, maybe a couple of years from now, 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, you align completely with some of my most unpopular beliefs, so it’s nice to have a kindred friend.

Thank you so much for joining me today, man.

Thanks for having me.