# Corgi Insurance: Asymmetric Growth & Relentless Execution

**Podcast:** The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
**Published:** 2026-05-30

## Transcript

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 have a mattress there.
I would rather measure my lifespan in victories than yours.
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.
I get a lot of backlash, the death threats and the DMs, you know, people think I'm nuts.
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 $2.5 billion.
But before we dive into the show 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.
Well, that's AMP, a beautiful, wall-mounted, smart gym that brings strength training, HIIT, Pilates, mobility, and yoga into one incredible system without the commute, the clutter, or the schedule.
AMP adapts 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 20VC 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.
It's why AMP has over 20,000 users, won the 2026 Forbes Vetted Best Product Award, and was featured in Fast Company, USA Today, and more.
You need to train better, and you need to start today.
Go to amp.ai to get started.
That's amp.ai.
While AMP Fitness logs your sets, Granola logs your calls.
You're in back-to-back meetings all day.
You're trying to stay present, but you're also worried you'll forget the decision, the action item, the important next step.
That's where Granola comes in.
Granola is an AI-powered notepad for meetings.
You jot down rough notes like you always do, and in the background, Granola transcribes and turns them into really clear, useful notes.
When the meeting...
ends.
No bots joining your call, no distractions, just a clean notepad that helps you focus.
During or after the call, you can chat with your notes, ask Granola to pull out action items, help you negotiate, write a follow-up email even, or coach you using recipes, which are pre-made prompts.
It's actually the same technology we use to create our podcast notes.
Once you try it on a first meeting, it's really hard to go back.
Head to granola.ai forward slash 20VC.
That's granola.ai.
AI forward slash 20VC and get three months free with the code 20VC.
That's 20VC.
Once Granola turns the conversation into clear notes, Finn keeps the conversation going with customers.
As AI agents become more common in customer experience, teams often end up juggling multiple silo tools for every job.
Well, Finn was built to change that.
It's a single unified agent that works across your entire customer experience from service to sales to success and beyond.
Fin is the agent making perfect customer experiences possible for thousands of customers.
It's powered by custom models, trained on years of real customer interactions, so it understands the nuance and complexity of customer service better than any other agent.
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 love Fin to deliver better customer experiences.
So see what Fin can do for your team at fin.ai forward slash 20VC.
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?
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 have to love winning.
I mean, you have to love the victories.
I think Jeff Bezos, he said something a number of years ago that has always really stuck with me.
He gave it as a baseball analogy, I guess, very American.
But, you know, in baseball...
There's four bases and you can score maximum of...
or there's three bases in the home plate, but you can score a maximum of four runs when you're at bat.
So 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 four runs, but your probability of striking out, of scoring nothing is quite high.
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.
It might result...
and something like AWS popping out of nowhere.
I really think 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.
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.
But I don't know.
I think the fear of losing can't really motivate you because otherwise you'd just become this creature afraid of doing anything.
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.
And so I'm going to ask you instead, what were you not aggressive enough on with the benefit of hindsight?
Yeah, it's a good question.
I think going to university, going to college, that was a big mistake.
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 metaphorically get beat up.
You need to, you know, go through the lows before you go through the highs.
I wasted some amount of time in 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, 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.
And 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 then replace them with the next guy.
And I think startups are a little bit like that, where there's not some inherent loyalty.
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 going through a company is just kind of 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 suppose, the point is to give 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 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 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 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.
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 capital is fungible.
And 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.
What makes he say that?
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 when describing a company, say, as a tier one company or as a YC company or as a 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, you know, 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.
You know, like if the team's incompetent or if they're making bad decisions, then that's a really hard thing to solve.
No, that is 100% true.
I have to ask you, 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 dream big and 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 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 brothers and sisters in arms with the people you're working with, then you should go all out.
You shouldn't do half-assing it.
Five days, why not four or three or two or one?
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?
I'm 100% with you on the work ethic.
And I do actually think having a day off can be helpful.
Do you not think that rest does carry...
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...
But they wouldn't have a place at Corgi.
You know, 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?
Like, 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 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 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 it's kind of it, but don't realize the intensity?
Yeah, I mean, we have everyone do work trials, so that scares them off.
What do you mean, work trials?
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 kind of 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.
That's a benefit of actually working weekends is people can do it in their jobs without taking time off.
Yeah, 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 two-day trial to have much impact on onboarding and whatever.
The soft skills matter, I think, more than the hard skills for me.
Because if someone really wants it, if they're all in, 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.
And it might not be exactly what they are applying for, what they think they're going to be doing.
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.
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 think that being extremely money motivated leads you to short term 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, your sacrifice is unwavering to this business.
We'll get onto 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.
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 where we're at now is that you can actually in a positive some way like make a really big difference in the world so I want us to always be solving the hardest problems possible and I want to win I want to add value 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 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 some yacht somewhere hanging out or at a visa or something.
It's another thing if you're actually putting in the work.
So I think symbols often really matter, like the cosmetic stuff, like having a sign on the building.
We're going to get to the sign, dude, don'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.
And I think that the symbolism around working hard is quite different, like leading the troops from the front line versus saying, oh, why don't you guys work hard and I won't.
So you literally live in the office?
Yeah, yeah.
I have a mattress there.
and that sort of thing.
I used to shower at the Equinox, like one street over, and they closed very early, like 8 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.
Yeah, I had this in Founder's 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 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...
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 I'm...
Have you ever had health scares?
Yeah, 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 years.
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 because if I'm dying either way, but 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 it's like they say, would you rather live 10 years less but have a gold medal?
And 98% of them said unwaveringly yes.
You need to want it and that's presupposing 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-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.
I mean, if you visit very high-growth 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.
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 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 because otherwise people like lose a lot of time like going out and like getting food and like coming back is just...
very inefficient and people need to think about where they're going to buy the food and 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 seven 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?
We really liked the idea of having a chef.
And again, like the chef we got was awesome.
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.
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.
And I was like, that seems eerily similar to Corgi's role.
And I was like, maybe it is.
Talk to me.
You have 24-7 Corgi Cafe.
Why?
You're an insurance company.
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.
It was like this empty barbershop.
It was really dungy, like I'd been out of business for probably a couple years.
We moved in, and everything was fine, and we have the sign on the side of the building, great.
But I'd walk in every day, and I'd 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...
It's a waste of everything.
At the same time, a huge complaint I have with San Francisco, everything closes really early.
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 push themselves hard, but you cannot find a cafe.
You can't even find a place to eat past 6, 7 p.m.
most days.
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 the world, 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, we decided to just kind of impromptu, it wasn't like a big planned out thing, open up a 24-7 cafe.
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.
How much money did it take to start a cafe?
We spent under $100,000 opening it.
Spent under $100,000 opening it.
Has it been successful?
I mean, it's always full.
If you go there, you can go there at 3 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 20 people have told me like, oh, like I submitted my YC app in like the Corgi Cafe and I got in or something along those lines or I signed a term sheet there.
You should do Corgi Ventures, which operates from 3 a.m.
to 5 a.m.
And it's like those founders that are there.
Yeah, I mean, the problem is if anything becomes a measure of success, it ceases to be a good measure once others...
the alpha disappears very quickly.
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 Brexpressos.
Yeah, Brexpresso.
We have Deal.
We have a couple of them.
What do 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, yeah.
So with that, I think we're probably slightly profitable.
If I was an investor, I'd say, Nico, I love you.
I love the energy.
This is a fucking distraction.
Yeah, they hated it at first.
Why are you doing a cafe 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've learned that you don't get any credit for ever 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 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 because of that, I think that there's certain exceptional qualities that London has.
And 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.
So we opened a London office before we opened a New York office.
We're a 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 we're paying above market, but we're not paying that much.
The thing is, 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...
Are you more generous than others on equity?
Because you understand that you are asking for more of someone's life being seven days old.
Yeah, yeah.
We're generous with top offs.
After people are working, we give more equity based upon performance.
That's where we're generous, more than the initial equity that people sign on.
Okay, so it's like accelerators on milestones hit.
Yeah, I mean, it's a little more ad hoc than that, but yeah, something like that.
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 core to winning.
Have you sold secondaries?
No, I haven't sold any secondaries.
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, and 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 gonna keep doing well and keep kicking ass, why would I sell that?
I don't really have a...
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 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's more people about too many pubs, that might be a problem.
There's a lot of pubs.
There are a lot of pubs.
Do you drink?
No, I don't drink.
But 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 really quite sure where to go to, San Francisco is like an end destination where 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 find your people oftentimes and where you'll find yourself moving to.
And I think that that's a special quality.
It's almost like a spiritual call.
like everyone's in an exile or something.
And I think that that's something that's very unique.
That's why New York is not a good place to have a company at all.
The people that 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 of these other places.
If you're hardcore about startups and you're American, then I think you should go to San Francisco.
Oftentimes, I mean, there's super great other cities.
I do like Chicago, and we have an office in Dallas that's really great too.
And 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.
I get you.
We've spoken a lot about everything from chefs to signage on buildings to Corgi Cafe 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, what was the biggest?
I don't dwell on mistakes.
I think...
How very Marc Andreessen of you.
Yeah, I think...
I look more at the victories 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 again and again.
There's a brilliant 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 would have 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 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 also very informative.
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 memetic 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 I think that being a student of the greats is great.
The important thing I think is probably not copying them.
Like 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'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.
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 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?
So naturally there's roles, I think, that creep in.
A lawyer or an accountant are not going to 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 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 like a return on investment calculation.
The only reason I can think of it is, you know, there's some point in which you need to take 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 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?
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 have a lot of children.
But if you want to clock in and then just check out of work, then you...
Respectfully, there's infinite other jobs you can get, and that's okay.
You know, Corgi's not for everyone.
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 death threats and the DMs, you know, people think I'm nuts.
Do you care?
Not really, no.
I don't know.
I mean, I...
Have you ever cared?
Yeah, I don't know.
I think when you're a young person, particularly I think young men don't have that much support within society.
And I think it's something, of course, that 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.
Do you think you're legitimate yet?
I know that sounds strange.
I mean, so we're more regular than a bank and we make a lot of revenue and have 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 that you don't get fired for buying IBM.
And I would, in my context as a fund, if you're Andreessen or you name these big, large platforms, you don't get fired as an LP for doing Andreessen.
Right.
Like period.
Yeah.
That's probably exactly right.
The thing is, in the fun context, Andreessen or Kleiner or even Sequoia back in the day, at some point, they were just a couple guys in some shitty room that didn't really know...
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.
There's always more legit, 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?
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 something good, generally speaking.
Who ends up doing extremely well?
If people are doing well, you need to just give them more equity, especially, and make it so that if they're doing a very simple return on investment calculation.
that the highest EV thing they can do is work in their current role.
And if you can't provide that upside, there's no reason for them to continue 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 the comp and the simple EV calculation is that you need to actually be solving big problems, and if you're not solving big problems, then no matter how much you pay people, you're not gonna retain them if they're actually good.
You can probably split, like, with any organization, 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 important, even if it makes a lot of noise.
Do you keep the mediocre?
I wouldn't put it like that, but, you know, I think in any organization, there's people that, you know, you wouldn't be devastated if they left.
The question I always ask is, knowing what you know now, would you hire them again?
It's the most important question.
Yeah, I mean, there's 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.
1.3 from TCV.
Love TCV, love John Doran, spoke to him before the show.
What are your single 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 dollars?
You know, 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.
So I think if you have to do anything for years.
What do you know now that you wish you'd 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 first pitch.
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 Coru, I think, was maybe first round capital.
I remember I took a red eye the night before.
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 Thursday night.
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.
So I started pitching Friday.
We had Saturday, Sunday, and had to get the money by Monday.
And, you know, I think the pitch was not very good, honestly.
I think it was a lot of, 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 first set of pitches I did weren't that good.
And you were raising two on 10?
We were raising five on 28 with that one.
And that was 2024, so that wasn't super easy.
That was recently.
It was like two years ago.
Yeah.
What was the best VC meeting you had?
The 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 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 like 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 really bad ones?
I've had some super bad ones.
What was the worst?
I've had people, especially the first round, the early stage investors are disrespectful.
I've had people driving.
I've had people flossing their teeth on the meeting, chowing down food, barbecue ribs or something where it's getting all over their face.
I've seen it all.
What did you say?
I mean, 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 are your biggest advice to founders on price?
Price is a difficult one.
Yeah, 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.
We always go with 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 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 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 fundraise process with you either.
But I do want to get to know you.
And I do want you to know me.
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 just like...
Again, this is interesting because 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.
Yeah.
Well, what the fuck?
I'm heads down.
You know what?
Because if you're working on an important deal, that's going to like double your revenue.
The last thing you want to do is meet with some VC.
I get it.
But then help 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 backhanded, like a...
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 we've 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 that a venture capital firm, it's a lot of things.
It's a brand, it's a lifestyle business.
But one thing is certainly as 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 their company was not doing well at all and a VC came in and saved them.
And the amount of gratitude I think 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 I think is hard.
And 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.
One thing I know about them is they can get deals done quickly.
Sure, but they can also be assholes.
That's true.
And I've had plenty of bad investors in my life.
Bad investors are much worse than no investor, and it's hard to get rid of them.
But 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.
Why would you waste time?
Do you think you price your company cheaply?
Yeah, we price all of our deals cheaply.
Why?
I mean, people might not think that when they see our stuff posted, but I think 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?
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.
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're good from like a- So are 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 valuing growth, whereas public markets feel like they're a vehicle for valuing cash flow.
In the past, we'd call it dividend stocks.
You know, 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 embodiment of their future free cash flow?
That is what a company valuation is.
No, 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 something.
Why do you buy a Rolex watch instead of a Chinese copy of a Rolex watch?
They might be the same materials or the same whatever, both tell the time.
If I give you unlimited money, what would you do that you're not doing today?
So 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's a lot of things I'd love to do.
I think within the context of Corgi, every single super, super regulated financial institution type, where right now it's run on fax machines and with boomers, we'd like to have those, not waste people's time and charge less fees and make everything a little more protected and a little more efficient and a little more profitable.
I think 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 a bet mostly on 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 mental health.
There's 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 be very commonplace in five years' time?
I don't know if it's a role in particular, but I think that actually AI makes sales and marketing much more important.
than it was in the past.
In the past, I think, if you had a really rock solid, super hardcore engineering and product team, you could come out with something that would just blow everyone away.
It'd be faster, it'd be better.
Now you can make something faster and better.
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 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.
The 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 that consumer companies have perfected marketing and B2B companies have perfected sales, much like in a company where you have a dominant product, how 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, 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've grown to value experience a lot more.
In the past, I've probably made certain statements around boomers being slow and bad.
I've definitely undervalued people that have been doing something for a long time because a lot of times there's these little nuances or edge cases.
When you do something for a long time, 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 trillions of dollars to make getting that knowledge out and putting it inside of computers that can think and talk.
I don't think I viewed those problems in that lens.
I think I just considered old people using fax machines moving at two miles per hour to be like 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.
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...
You think that 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.
There's the board of Check the Box.
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 anyways probably with or without a board.
That's a management problem.
You can buy OpenAI or Anthropic today.
Both at the same price, $900.
Which one do you choose?
Yeah, I'm going to get in trouble for this probably, but I guess the disclaimer is this might be a stated preference versus a revealed preference given that we spend maybe like $400,000 per month on Anthropic and $0 on OpenAI at the moment.
But I think that like spiritually, like OpenAI is, I guess, a little more pure.
because they kind of created this idea of like an AI lab as a company, dating all the way back to YC research.
And Anthropic is a result of employees that didn't like the management or the direction.
There were complaints about profit and ethics and all this other stuff.
And the EA movement and all of that.
I think when your origins are that impure, it's a little hard to overtake the king.
And 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 from an enterprise or workflow automation perspective.
Anthropic's 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 signed contracts.
And 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's good companies and there's everyone else.
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 100 years.
Those companies, 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.
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 Andrel and Anthropic.
Those are super different companies.
I think both of those could be good companies, but I don't think people really understand the philosophy behind the management teams that they're investing in.
Who do you think is the most underappreciated CEO today?
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...
One area where more than kind of venture-backed companies, what I would love to see more of are venture funds speaking out about these sort of important topics.
And I know startup founders love to clown on VCs for chiming in about topics that they might not know a lot about.
But I think that venture funds are actually in, despite the fact that they're...
and need to raise from LPs, and LPs can crack the whip or whatever.
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 CEOs or the people that are running venture funds.
actually take a more active stance in aligning their deployed capital with the changes that they'd like to see in the world.
And to me, that's perhaps a more important issue than any particular company's CEO or management team, broadly speaking.
Would you blame VCs for the dramatic increase we've seen in fraud, especially around ARR?
We put so much emphasis on zero to 100 million in X amount of time.
No wonder founders lie.
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 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 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 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 arbitraging that and pumping the...
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 YC or whatever for some of their companies being frauds is probably not directionally correct because it's not like any venture fund really wants to invest in a fraud.
And people that are doing these things, they're very good at...
wrapping it up and disguising it in such a way that it will pass muster, especially if a round 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.
But Jared's 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 for when you look forward to the next 10 years?
What are you like, this I can't wait for?
You know, 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 2022 that people actually started getting, with ChatGPT 3.5, that large language models were obviously very important and very exciting.
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.
I think that there's certain areas where venture investing hasn't worked before, where there could be category defining.
outcomes and where there could be new kind of industries 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 going to probably see more like chat GPT moments maybe a couple of years from now that 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, 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, why not?
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, HIIT, Pilates, mobility and yoga into one incredible system.
Without the commute, the clutter or the schedule, AMP adapts 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 20VC 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.
It's why AMP has over 20,000 users, won the 2026 Forbes Vetted Best Product Award, and was featured in Fast Company, USA Today, and more.
You need to train better, and you need to start today.
Go to amp.ai to get a...
started.
That's AMP.AI.
While AMP Fitness logs your sets, Granola logs your calls.
You're in back-to-back meetings all day.
You're trying to stay present, but you're also worried you'll forget the decision, the action item, the important next step.
That's where Granola comes in.
Granola is an AI-powered notepad for meetings.
You jot down rough notes like you always do, and in the background, Granola transcribes and turns them into really clear, useful notes when the meeting ends.
No bots joining your cool No distractions, just a clean notepad that helps you focus.
During or after the call, you can chat with your notes, ask Granola to pull out action items, help you negotiate, write a follow-up email even, or coach you using recipes, which are pre-made prompts.
It's actually the same technology we use to create our podcast notes.
Once you try it on a first meeting, it's really hard to go back.
Head to granola.ai forward slash 20VC.
That's granola.ai forward slash 20VC.
and get three months free with the code 20VC.
That's 20VC.
Once Granola turns the conversation into clear notes, Finn keeps the conversation going with customers.
As AI agents become more common in customer experience, teams often end up juggling multiple silo tools for every job.
Well, Finn was built to change that.
It's a single unified agent that works across your entire customer experience, from service to sales to success and beyond.
Finn is the agent making per- customer experiences possible for thousands of customers.
It's powered by custom models, trained on years of real customer interactions, so it understands the nuance and complexity of customer service better than any other agent.
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 and Crypto.com already use and love Fin to deliver better customer experiences.
So see what Fin can do for your team at fin.ai forward slash 20VC.