20VC：AI将如何改变世界的7个预测：劳动力、工程、社交媒体、GrokBots购买Cybercabs等——与Eight Sleep联合创始人Matteo Franceschetti对谈

Our engineers stopped coding around a year ago. A great brand with a shitty product goes nowhere. I'm extremely demanding—I'm a weirdo. But business-wise, no mercy.

Sometimes people say, “Oh, I'm at the final stage with Anthropic and Eight Sleep.” To me, that is a really bad red flag, but it means you're confused. There is no way that these 2 jobs are in any way similar. Our revenue per employee is way higher than Apple's.

Kids that are being born now will never work, at least for money. I'm the type of guy that, when I have a goal, you don't stop me. I become a beast.

Matteo, it is so good to have you in the hot seat, dude. Last time we did this show, you had a hiring playbook, and I remember it went insanely viral afterward. So many people talked to me about it ever since we did it. I'm really excited for this second discussion. Thank you for doing it, dude.

I think that hiring today is harder than it's ever been because of the prices on offer at OpenAI, Anthropic, and some of the other places—even the shiny, new, hot startups. How do you think about that? Am I wrong? Has it changed in terms of talent competitiveness?

1. The AI Hiring War

We are back to 2021, and I think that is becoming a problem in the US, meaning salaries are going out of control.

What makes you say that? Engineer salaries?

Any salary. Even for product managers, salaries are out of control right now. They get insane offers from any company. Obviously, there is a lot of money going around, so we are focused more and more on hiring in Europe and outside the US.

The other problem is not even the salary, and it's not even attracting them at T0, but retention. If you are a cool company with a cool brand, then they keep receiving offers over and over at a higher salary.

Have you lost people to OpenAI and Anthropic? I'm invested in many companies, and they're just like, “God, we're getting eaten alive by OpenAI, Anthropic, Cognition—you name these hot companies.”

Yeah, a couple. The other ones could be AI companies that are doing extremely well or have just raised money, and that's normal competition. But sometimes the delta in salary and compensation is so big that, at that point, there is nothing you can do.

We mentioned Cognition a couple of times. We were talking earlier about your angel investing as well. How has being an angel investor changed how you think about operating?

2. Learning Through Angel Investing

It's a game changer for me, and I think that is something that is not shared enough, particularly on X. The amount of learning that you get from being an investor is insane because, essentially, you build your own intelligence.

As you receive investor updates, you understand how the market is moving, what the valuations are, what the multiples are, what kind of profiles companies are hiring, and what channels might be working. I receive these from companies that are not competitive with Eight Sleep, but as a founder, you just get a sense of the market, and I find that super valuable.

What's been the biggest lesson from angel investing?

The biggest learning is always about fundraising, right? You see how much they're raising, at what valuation, what multiples, and which investors. That's one.

The other biggest lesson is for other companies that are still consumer companies: to see what channels work for them or what markets work for them.

What do investors not understand about hardware that they should? You're advising me. I'm your buddy. I have a fund, and I want to invest in hardware. What are you like, “Dude, before you do it, you should know this”?

Probably that founders, in the first year of the company—or in the first, probably, let's say, 3 months—don't fully understand what the cost of producing that device will be. They don't understand the return rate. Everything they tell you about BOM and COGS will probably be off by at least 50%.

Does CAC go down over time?

3. Disciplined Growth Channels

It really depends, and that is another thing you want to assess, which is word of mouth. In our case, word of mouth keeps compounding. It accounts for around 40% of our revenue, even at our size, which is starting to be really big.

Forty percent of your revenue, you say, is word of mouth?

Yep.

What's your second-biggest channel?

Then you start getting into paid media.

And that's just Meta?

Yeah, then it becomes Meta, Google, TikTok, and all those channels.

Can I ask how they compare? I'm a content specialist, hopefully, at this point. No one that I speak to has managed to make TikTok work. Have you?

We did, actually, this year, in the past 6 months.

How?

It's usually a matter of the amount of content that you can generate with TikTok influencers.

So it's about getting a UGC program in place?

Yep.

Is there a big budget for you tied to it?

The way we usually approach these channels is that we start by unlocking a small budget per week. We start looking at CAC and set a cap on the CAC, and then they can deploy as much as they can within that cap. As they prove it, they can deploy more money.

To me, they could deploy $100 million if they are within the CAC cap. The important thing you need to do regularly, probably every 6 months, is an incrementality test. We might turn off TikTok in certain states in the US or in certain geos and start A/B testing what the growth rate or the revenue rate is.

We want to see how much each channel is incremental because we don't look at the CAC from the platform. We have our own models now that determine the CAC of each channel.

Sorry, can you tell me about that? You have your own models to determine the CAC from each channel.

Why is that?

Well, because you cannot trust that there will not be an excess of attribution from the same platform. We do the same with Meta. If you look at the CAC on Meta, it’s probably 20% lower than what the true CAC is, and the only way you can determine it is by doing these incrementality tests.

Let’s say you pick 2 geos that perform similarly. Let’s say you pick Texas and, I don’t know, California. That is not the right example, but maybe—

Dude, you’re speaking to a Brit. That’ll totally work for this example—yeah.

Yeah. Then you turn off Texas, and you start seeing what the delta in performance is for that state versus the other—how much revenue you lose. If they were both growing 50% year over year, and you start turning off Meta in one or the other, you can immediately calculate the value of Meta for that state.

Does every brand need to have its own models to accurately—

Oh, 100%, because otherwise they just fool themselves. You don’t know what—

When did you start? It’s one of those things that you can’t do from day 1.

No. You will screw up multiple times. The point is, you need to keep doing it because as you add more channels, the incrementality of each channel will not be the same.

How did you think about adding channels? I see so many founders try to be everywhere to everyone.

Yeah.

How do you think about that?

I disagree with that. You need to go 1 channel at a time. I was even talking to a common friend recently who was asking me about that, saying, “Okay, can I go into all these channels? How much money should I put in? Should I start putting $100,000 in each of them?”

I said, “No, no, no. You go 1 by 1. You start with Meta. It’s probably the biggest channel and the one that you should prove the fastest. Based on the size of the company, you start with a certain amount per week. You set the cap to the CAC you want to achieve, and then from there you start scaling only if you are within CAC.”

Otherwise, you start throwing money out of the window. Your growth people will always want to grow faster, so they will always want to spend more, and then you start losing control. What happens then? Let’s say by the end of the year you realize you screwed up, and so you start pulling back. Then the following year, you’re not growing year over year because you’re spending less. You need to be disciplined now if you want to be successful next year and keep growing year over year.

It’s really interesting how you gamify growth numbers, because you’re right: you spend—

100%, yeah.

—you get 400% growth, you pull back hard—

100%.

—and you get 70%. Good luck fundraising when—

Yeah.

—you’re going from 400% to 70%.

Yeah. We could be growing 50% more year over year this year just by spending more. But then next year you’re in trouble because your CAC is upside down.

Do we care about economics from day 1? You said there about start with Matter. Do we care about economics from day 1 in terms of optimization, or is it actually, “Hey, customers are engaging, they’re liking the product. If we’re doing a 1:1—for every dollar we spend, we’re getting a dollar back—great”? Or should we be looking for optimal returns early?

In our case, we look at the immediate payback period. This is actually something where Keith was really pushy, and he was correct from day 1. He wanted us to have an immediate payback period.

Then we have what we call contribution margin, which is the margin on day 0. We have the subscription, and the subscription will compound on top of that, but we want to have that contribution profit on day 1 to be really healthy. If we were compressing that, we could be growing 50% more, but then the business wouldn’t be public-ready or as healthy as it is today.

What would you most like to do if economics were not a part of your business? It could be massively increasing the quality at a certain point, or pouring fuel on the fire at Eight Sleep like never before. Take economics aside.

You could reduce prices, and I think we would see an acceleration, or you could deploy more into marketing, which is probably what I would prefer. I’m never a fan of compressing prices. You know what Andreessen says: if you have a great product, people will pay for it.

But at our stage as a company, even if we start fairly large, brand awareness is still probably the biggest bottleneck.

You have a subscription business as well, which obviously provides a lot of juice to your margins. Because you have an upfront cost in the thousands, it’s a relatively expensive product—

Mm-hmm.

—for a lot of people. Do you inherently have very low churn rates on your subscription product because you have the buy-in of multiple thousands of dollars invested upfront?

Yeah, it’s world-class. Our churn is the lowest of any company you can think of.

What is the churn?

It’s in the single digits—low single-digit yearly churn. Even if you compare us to other companies in the wearable space that are going public, we are better than them.

Who could that be?

Who could that be? Yeah.

I don’t know. That’s absolutely hilarious.

Yeah.

But it’s world-class. It’s unseen.

Going back to the channels—and I’m sorry for focusing on channels; I’m just a real nerd about channels—has your Google spend changed in the wake of AI and AI-driven search impacting so much?

4. AI Runs The Company

Yes. We introduced a new channel that we now monitor, which is literally what we call AI SEO. In the report that I receive twice a week, there is also AI SEO, and so we see how we rank in AI searches.

What percentage of traffic today is from AI searches?

I don’t have a number for that. I can check, but it keeps growing.

But is it 1% or 20%?

Probably somewhere in the middle. But we’re starting to see an impact on Google. Our assumption is that Google is behaving differently because of AI searches.

What was your biggest channel mistake? Where did you spend money that you shouldn’t have, and you thought, “I learned a lot of lessons from this”?

Out-of-home advertising. Everything depends on the scale of the business in that country. We tried to do an out-of-home campaign in the Middle East, but we weren’t ready yet.

If we were doing an out-of-home campaign in New York, where we are decently well known, it would perform very differently than the same campaign in the Middle East, where we just launched a year ago. Those are the things I’m learning that I didn’t know.

When are you big enough to do out-of-home? One thing that we’ve seen in the last 2 years is tech companies realizing the importance of brand marketing, out-of-home, football shirt sponsorships—you name it—and it supposedly performing well. How big do you have to be to do out-of-home?

I don’t think there is a hard number, but you want to be a brand that is decently well known. I’ll make it up: if 100 people see that ad on the street, I don’t know, 5% of them know the brand.

That is one of the other things that we monitor: aided and unaided brand awareness, to understand how many people know the brand and, if they know the brand, whether they know what the brand does.

How much did you spend on out-of-home?

Nothing now. But we created a truck that goes around Silicon Valley, and you can book the truck and it comes to your home so you can try the product live. The truck has a bedroom built into the back.

Now the truck also goes to specific events or specific areas during the weekend where there are many people, and we’re seeing pretty good success because there are a lot of people who wanted to try our product but couldn’t. Now, when they see the truck, they just get into the truck, try the product, and buy it.

That’s a phenomenal channel, and you’re going to have a high conversion rate on that.

Yeah. It’s doing pretty well.

That’s fascinating. I’m also really impressed that TikTok works for you, because TikTok is freaking hard.

Yeah. It wasn’t working in the past. Then we kept iterating, and it just started working 6 months ago.

How big is the marketing budget today?

In the hundreds of millions.

In the hundreds of millions?

Yeah. A story I can tell you is that, for example, we used to have an email marketing team. Now we have 0. Everything is done through AI, and email marketing makes a very large amount for us. Everything is run by AI.

How?

We were forced into that. We had a team of 2, and then the person leading the team was leaving. At that point, my co-founder Alexandra jumped in and said, “Okay, let me see how I can use AI to really make this work.”

Within 3 days, she was able to build multiple bots that now run all our email marketing. Now we have a team of 0, and email marketing makes close to $100 million.

I just want to understand, because we have an email newsletter, and there are people who do it, and it’s still pretty average, I think.

When you say bots—

Yeah.

What, you build your own?

So, yeah. For us, obviously, there is a calendar of what emails need to be built, created, and sent. This is also based on history, so we have historical data. Our AI suggests when to send what email with what copy.

And when you say your AI, it's your models? It's using Claude—

Yeah.

It's using—

Yeah. We probably—I mean, we should check, but I would imagine we are using Claude for that. Then internally, we have probably, by now, hundreds, if not thousands, of agents that we use internally at Eight Sleep. So now I started measuring what I call the human employees, but then there are also the AI employees. And probably the AI employees are—I mean, without probably, we are probably 3 or 4 times bigger if you start including all our AI employees.

Where is it most significantly impacting the company?

Growth, because email is like that. Now also all our digital marketing: our team receives a report every morning from our AI agents suggesting what changes to make or not make, and they approve or reject them. So also all our marketing business is run—our growth is run—by a few people right now.

I worry that in a world of infinite content supply, discovery becomes impossible and we just get flooded. Do you worry about that too?

Definitely. But at the same time, I think that the personal agents will look for the best product, and so if you are the best product, you will still win. There will probably be— for humans, the amount of content will be too much, and so we'll need to think about how we show up to humans, where humans go. That is how I think about it. But you need a different strategy for the agents to make sure that their agents find you and recommend you.

We said there about the amount of agents that you have. Engineering is one where, consistently across the board, everyone's engineering teams are being changed unbelievably. How is AI changing your engineering team at Eight Sleep? What are you using? What are you not using? How do you think about that?

Yeah. Well, our engineers stopped coding around a year ago. Since then, they haven't coded. What they have are hundreds of AI engineers that code for them, and that is how we can achieve what we are achieving at scale in 35 countries, including China, the Middle East, and Europe, where there are a lot of regulations in all of them, with a fairly tiny team.

What tooling do you use?

Mainly Claude.

How much do you spend on Claude a month?

It keeps growing so fast that I don't know.

Is it, like, $5 million?

No, it's lower than that, but it's still in the millions.

And the thing I'm trying to understand is, Marc Benioff said that they spend $300 million a year on Claude, and they have a $6 billion budget for engineering. 5% of engineering salary is being spent on Claude in particular.

Yeah.

And my question as an investor is: will it stay at 5%? In which case, we can justify the $2 trillion IPO, but it doesn't have massive expansion from there. Is it a case that 5% is just the start—baby, we're gonna go to 25%—in which case, Matteo, let's load up on Anthropic's IPO? Or is it the case that actually we're gonna see commoditization by open models, most workflows are gonna get taken by them, and that 5% could go down to 1% as we see efficiency?

5. The Economics Of AI

Yeah. I think there will be 2 vectors in the opposite direction. The usage will increase, and so the 5% will become 50%, but the cost will go down. And so, net-net, I think it will go down.

I was listening to an interview with Sam Altman recently, and he was saying that in the early days, to pay for 1 hour of electricity a night, you had to work 5 hours, just to give you a sense of how expensive electricity was in the early days. And now nobody cares about—I don't even know what the cost of electricity at night is in Miami, where I live. I think the same thing will happen.

Do you find it a bit scary that intelligence is now free and entirely distributed?

Yeah. It's something I—

Like, just the idea—like, shit.

Yeah, I think about all that, right? How businesses will change, how our business will change once that intelligence is semi-unlimited.

But I asked Instinct this morning to do an in-depth analysis of 3 of our biggest competitors' Instagram channels, because I want Instagram to be a real driver for us moving forwards: what works, what doesn't, what themes work, what hooks work, what layouts work, what doesn't, and what captions work. It was incredible. And I said, “Can you suggest 3 stories every single day for me at 8:00 a.m. to do?” The first one starts tomorrow.

Yeah. The amount of productivity will explode. It's probably like when we went from no computers to computers, or probably even bigger—the Industrial Revolution or Agricultural Revolution. We are facing one of those moments.

Knowing what you know now as a consumer and customer of Claude, would you buy Anthropic at the IPO?

I would probably buy. I still think there is so much upside in all these companies. I'm really bullish on SpaceX, personally.

Why? What drives that?

So here is another theory that I have, and obviously it's just my opinion, but I think with AI, the right companies will transform themselves into holdings. What that means is that whatever Eight Sleep is doing today will be one of the businesses that we do. But with AI, as we build tools for ourselves, we'll discover other opportunities—business opportunities. And so Eight Sleep Inc. will probably own 3, 4, 5, or 10 different businesses. Which, if you think and if you look at Chinese companies, is something they have been doing forever.

If you look at Xiaomi, Xiaomi does 15 different things. I just watched their latest presentation from their CMO. I look at a lot of Chinese companies because they are geniuses, right? They never stop themselves. Xiaomi, instead of being just like Apple, also does cars, for example. They do so many other things.

And fridges and ovens, and you're like—

Literally. Anything hardware-related, anything that is a smart home, but then they also get into components. BYD develops certain components well outside the car and automotive space. These companies have already proven that the concept of focus is not, “Oh, you keep doing the same thing forever.” It's just: I have certain capabilities, so how can I use this knowledge and these capabilities in any form? And with AI, we will all do that.

I'm loving this conversation. And the joys of doing Second Choices is that they're much more casual, which is much better to listen to and also much more fun to do. Do you worry, when you see the excellence of these Chinese manufacturers, specifically in the automotive industry, that it's just gonna hollow out the European car market?

6. China’s Industrial Leap

Yeah, I think the Chinese really nail automotive. And based on my understanding, what happened is that around 10 years ago, they understood that they didn't want to compete with European manufacturers on standard engines, and that is when they decided to double down on electrical technology. Since then, they started developing their cars.

But I go to China often for work now. We sell in China, but we also manufacture in China. And when you see the quality of their cars—because in the past, we used to think that some of these products were just cheap and ugly—well, instead, now they design cars.

Xiaomi, if you go to their stores, looks like an Apple Store, but there are cars and other devices for the home. These cars literally look like they have Ferrari aesthetics, or they have these seats that turn, so you can just sit and then—

Dude, I've seen the TikToks. It's so cool.

Yeah.

Screens come down.

Screens come down.

Stars on the ceiling.

Massage.

Yeah.

Everything is voice-controlled. So they're really focused on the customer experience, and it's incredible. I think a lot of other manufacturers around the world don't focus enough on the user experience.

I completely get you and agree with that.

Yeah.

But as your wonderful accent denotes, you are Italian.

Yeah.

And a huge amount of the European industrial economy is centered around cars.

Yeah.

Do you worry about that?

Well, I worry even more about another factor. I think all the Chinese manufacturers will become robotic companies. I think all these automakers should transform themselves and start building humanoids, because the humanoid will be what cars were in the '60s. If they don't do that, they will not only lose cars; they will also lose the humanoid market, which is trillions of dollars.

Are you seeing the advancement with humanoids in China in a way that you really didn't expect?

Yes. I don't know what the formal name was—the Olympics of robots?

The Humanoid Games, I think it was.

Yeah. It's insane. The way I look at that is: okay, you look at the thing, it looks a bit funny; they look a bit clunky, but they start doing things. Knowing how fast AI is moving, those same games will be mind-blowing next year.

That is what worries me. What I saw today, if you just look at that and say, “Oh, look at the thing—these robots are not really good at walking.” Even if they set records in the 100 meters, there was a robot that ran faster than Usain Bolt.

I did a video on this.

Yeah.

There was a robot that won the high jump.

Yes, I saw that. And then there were the fights—the fighters.

Yeah.

Tennis.

Yeah.

Like real-time tennis.

The tennis was really cool.

It’s insane.

Yeah. But in 1 year from now, we will be blown away by the speed of AI.

Did you see the paper, essay, or post last night from someone at OpenAI? Sam promoted it. It basically said, “We actually need to put a slight pause on this. It is getting too far, too fast.”

Yeah. I think the part that is worrying everybody is the self-learning part of these models. They are getting to the point where they train themselves, and that is when we start losing control.

Do you not think we’re already there?

I think we are. And I think there is a big delta between what we see as users and what the frontier model companies probably have in-house. I think they have already seen it behind the scenes. You’ve seen some of the things that are happening already in terms of cybersecurity, in these civilizations, where there were 3 attempts of civilization, I think, in an OpenAI model, where agents were building their own group.

I’m going to go there. You sell in China. You spend a lot of time in China. A lot of your investors, including Keith Rabois, who’s a friend of mine, fucking hates China. How do you reflect on that? Is it as evil and CCP-driven as it seems? Are we in a de-globalized world that should hate China? How do you think about that?

7. Expanding Across Global Markets

Yeah. I don’t have a specific opinion on that, so I cannot really comment. I can just tell you that, for us, it is a key market and a big opportunity. We decided to sell there, and it’s doing really well for us.

Is it very different selling in China?

Yes, because you cannot sell on EightSleep.com. Literally, you don’t sell on a website. They don’t use websites, so for us, it was literally learning everything from scratch.

What do you mean, they don’t sell on a website?

Chinese people don’t buy on websites. There is no e-commerce as we know it. They only buy on their super apps, such as WeChat, RedNote, and their equivalents. We had to learn all that.

What the fuck? So where do they land? You send a referral link to your friend? But where’s the referral link from? I’m confused.

Imagine that everything—the equivalent, oversimplified—is like if you were buying everything on WhatsApp. They don’t go on any website. Websites are, at most, just places where you can scroll, see some pictures, and read a bit more about the product. But all the purchases and all their credit cards are on RedNote, an Amazon equivalent, a WhatsApp equivalent, or TikTok, obviously.

Does that impact how you think about how we should think about security for these AI assistants? Everyone now is like, “Oh, I would never put my credit card in an AI agent.” Or, “What if it gets hacked?”

Yeah. I think the solution for that, to me, is that my Grok bot is already buying things for me, but it’s using Amazon in the browser, and Amazon has my credit card. I feel confident there because I’m not sharing my credit card with AI yet.

I think in AI, we are where we were with credit cards when spending and buying things on the internet 20 years ago.

Yeah.

People, particularly Europeans and Italians—I was still living in Italy—literally didn’t want to put their credit cards on any website because they thought it was a scam. Sometimes there was a scam back then. I think we are at the same point with giving our credit card or information to these bots. It’s still a bit uncomfortable sometimes, but I think in 1 or 2 years, our bots—particularly bots from frontier models like X, OpenAI, and Claude—you’ll start trusting them soon.

What seems crazy today that you think will be very common in 5 years? I totally remember I wasn’t allowed on eBay when I was young because my parents were like, “No way are you putting credit card details online.”

Yeah.

I remember when it was like, “You think you’re going to find a partner online? These apps are ridiculous.”

Yeah.

Now 60% of relationships start online, and I think we live online, transaction-wise.

Probably your bot buying a Cybercab that will start making money for you. You will buy a Cybercab that makes money for you with a bot, and the bot runs the Cybercab. That would be pretty sick.

I mean, it’s not that far off happening now.

No, no. And then it will be the health part. That is another area where I hope that cancer can be solved within 10 years. I think companies like Eight Sleep will be able to save your life, save the lives of millions of people.

Does the Eight Sleep product actually change that much, with the greatest respect, in a completely AI-driven world?

100%. We’re starting to see, in our data, the likelihood that you develop diabetes and hypertension. We are becoming a medical device for sleep apnea. Your bed will become the most advanced medical platform you’ve ever had.

You said retail earlier. I bet retail has been a question for you for years, and I bet there have been different board conversations. How do you think about when’s the right time? You’re still not in retail—you’re still D2C. How do you think about when’s the right time?

Well, let me step back for a second. One thing I’m learning as an entrepreneur is that there is a time for things, similar to what I was telling you about the out-of-home campaign. Nailing the timing of what you do—when you do what—is actually really important for CEOs.

It’s not binary, where retail doesn’t work or out-of-home doesn’t work. It works, but there are some secondary or lower-level conditions that are required to make that project work. I think for Eight Sleep, that is happening now.

You should imagine retail becoming a meaningful part of our channels in the next months and years. Before, it would have been too early. The same goes for China. When launching in China, I spoke to a lot of Chinese founders, and what they told me is that sometimes, when they start their consumer products, they actually start selling outside China first.

I said, “Why? You have such a big market, and you know the market.” They said, “Because the Chinese market loves to buy products that are already well-recognized in the Western world.” You want to build the product and the brand first in the rest of the world, and then you come back to China. Otherwise, in China, you would be one of many knockoffs, and it would just be a price war.

I didn’t know that. We just decided to launch in China, so we were just doing it. But I didn’t understand that, for us, it was the right time to get into China because now we are already selling in 35 countries. We are well-recognized. We sponsor Charles Leclerc and now work with Ferrari through Charles. That is a very well-recognized brand. Many athletes use us. Elon Musk has spoken about us. Mark Zuckerberg has spoken about us. Elon is really big in China, right?

You have a level of trust where you command a certain price. But if we were doing the same thing 5 years ago, we would have been destroyed by a knockoff that was $500 cheaper.

I had Hugo Barra on the show, who was a former executive from Xiaomi, and he taught me something very important in hardware. I’m intrigued if you agree with it. He said you need to be one of 2 things. You either need to be price king, which means you’re the cheapest, or feature king, which means you’re the best.

Yeah.

Do you agree with that?

I agree that you can be the best on price. That’s not what we want to be. Or I would call it the best product and brand. It’s not so much about features, but the brand is really important.

Being a brand that is associated with Charles Leclerc and Elon Musk—people they really respect—is something they want. The same thing happens in Europe. I grew up, and I remember when I bought my iPod. It was impossible, and I was buying a secondhand iPod on eBay back then because Americans had this product and it wasn’t being sold in Europe yet. There is that kind of fervor.

I completely agree. Listen: 1,000 songs in your pocket, in a beautiful package.

Yes.

Did Samsung and all the others have 1,000 songs in your clunky device too?

Yeah.

It was the same in many ways.

It was 100% the same. Steve Jobs has always been a genius because he was coming with a great product after everybody else, sometimes 1, 2, or 3 years later, but he was nailing the branding, the packaging, the pitch, and, obviously, the look. Everybody wanted it.

What do you think people don’t consider enough about consumer brands?

I think it’s the brand, particularly in Silicon Valley. In Silicon Valley, we understand building the best product really well, but I think we underestimate the importance of brand.

Then a great brand with a shitty product goes nowhere. First it's product, but then you need to be able to build a brand that is aspirational and can command a certain price.

Charles Leclerc is a phenomenal talent, for those who don't know, in the racing world—one of the best. How does that come to be? Do you get a DM from Charles saying, “I love Eight Sleep. Do you want to sponsor me?” How does that come to be?

Well, it's pretty incredible, the story. We got connected. Charles already had our product for 2 years before we met, and we didn't even know. That is the best way, obviously, for us to start the relationship. Then I'm an F1- and motorsport-obsessed fan. Obsessed. I know everything about kids racing go-karts. So I knew about Charles 6 or 7 years before he got into F1.

3 years before F1, he was racing; 2 years before, he was racing in F2. At the time, I reached out to his team in F2 and said, “I'm a huge Charles fan. I think he will make it big. Is there any way Eight Sleep can sponsor him?” But at the time, Eight Sleep was very tiny, so we couldn't find any real deal.

When I met Charles, I still had the email where I had been going back and forth with his team. I wanted to sponsor him before he even made it to F1—not to Ferrari, but before F1. Then I shared with him our vision, our medical vision. He really cares about that, and he's actually really into AI. He's incredible—super sharp, super into AI.

We had dinner together, I think it was the Wednesday of the GP in Miami, and before the end of the dinner, we said we were going to work together. The deal was done in a matter of days.

Can I ask how much it cost? No, you can't.

I can't share that. What I can tell you is that Charles invested in Eight Sleep. First, I was really happy because he was one of my heroes, but second, I think that proves what I was telling you about how smart he is as an entrepreneur and businessman.

Can I ask you, I think a lot more celebrities and athletes are obviously trying to be investors and wanting to invest today than ever before. What would be your biggest advice to other founders on how to get them and how to get the most out of them as a founder of a company?

We made a lot of mistakes with that, too. It's probably been 4 or 5 years that we've invested in sports, because obviously we have Charles. We were sponsoring the UAE team with Pogačar. Pogačar was installing our product every single night at each hotel of each stage of the Tour de France since last year, and we didn't even know.

He won last year, and then he won this year. So the team reached out after the first year and said, “Look, Pogačar did everything on his own. We bought the product. Now everybody on the team wants it. Can we do something together?” So we sponsored the UAE team this year.

Then we're in padel with Arturo Coello and Federico Chingotto, number 1 and number 3 in the world. We're in tennis, where we sponsor a lot of coaches, including the coach of Sabalenka and many others. There are a lot of top, top athletes who use our product. It's not public.

But what would you advise founders on lessons from how to get great talent? It can be celebrity investors, too—pop stars—

Yeah.

DJs, you name it, and how to get the most out of them?

Yeah.

Or are they just not that badly?

Well, there are 2 conditions for any deal now. First, they need to use the product. If they already use it, they bought it on their own, perfect; now we can talk about doing a deal. If not, they need to try it, and then we want to hear the feedback. They need to know the product; otherwise, it's just a pure business transaction, and I don't like it.

Second, I want to have a direct relationship with them. Usually, managers don't want that, and they want to try to be in the middle. But if I don't have the direct relationship with the athlete, we're not going to do the deal, because then it's just a financial deal, and at this point, we don't care.

I want to be connected to the athlete. I want to know that they love our product. If they don't, it's fine, but then the relationship will never work, particularly in a product like ours, where the biggest value they provide is simply talking to their friends about how good our product is. They really need to be bought in. If they just have a stake in our company because they put in a few million dollars, you don't go anywhere.

Who would you most like to have on the cap table who you don't have?

Probably...

Do you have Cristiano Ronaldo?

No.

He would be amazing. Have you seen pictures of him training? I'm a straight man. My God, this guy's body is incredible. I looked at it and then I looked at myself, and I just felt like—

Yeah.

Oh, dear.

For us, there is a big difference between the athletes that we can disclose and the athletes that use the product. Some of the top, top tennis players ping us, and in all the Grand Slams, they sleep on our product. In F1, we have probably 80% of Formula 1 drivers sleeping on the product, including the people who are winning, but we're not allowed to share that. It's a private, confidential relationship.

Do you have any wild stories of delivering it somewhere crazy for someone at the last minute because they need it before—

Yeah. Yeah.

You don't need to say the person.

I won't share the name, but there is this really, really famous football player. He tries the product at a friend's house, and then his team reaches out and says, “The athlete wants the product. Can you install it for him? Can you come and let him try it at home?”

The team goes, but once they get there, he has this very unique, special-size $300,000 mattress. Our product doesn't fit because we have the queen, the king—the standard sizes—but this was unique and customized. The team is leaving, but then the athlete says, “No, no, no, no. Okay, would you mind installing this in my kid's room?” They say, “Fine,” because that was a standard-size mattress, and so we install it there.

A week later, the athlete calls us and says, “Look, I'm going to give away my $300,000 mattress, but I'm going to move Eight Sleep into my bedroom. I need it for my own performance.” So he threw away the $300,000 mattress, and now he sleeps on Eight Sleep.

That was really sick. There is this other story that is really cool. One of the most famous actors in the world got our product as a gift, and he absolutely loves it. Then he buys 10 of our products for everybody in his family.

I go to this dinner, and this famous actor comes in. It's me and some top, top CEOs—CEOs of $100 billion-plus companies. He starts shaking hands and spends literally 3 seconds with everybody. “Hi.” Three seconds. Then he comes to me and realizes I'm the CEO of Eight Sleep, and at that point we start talking for literally 5 minutes, to the point where the other CEOs were looking at me like, “Who is this guy?” After that, they were looking at me with a lot of respect.

What is the most Eight Sleeps one person has bought?

A very famous person that everybody knows has 55 for his houses, but there are other people who buy through embassies, and they bought them in the hundreds.

Someone bought 55 for their houses? What?

Yeah.

Do you get a discount?

No, these people don't ask for a discount. They just reach out, and their team asks us to help with the setup or to place such an order.

That is wild. I love that.

Well, there is another story.

Yeah.

There is this couple, and they reach out because wherever they go, if they stay in a hotel for, I believe, longer than 3 or 4 nights, they buy an Eight Sleep to install in that hotel. They can't sleep without it.

Do you mind that Eight Sleep is such a premium product? Would you like it to be more for everyone?

We want to democratize sleep. The way I always say is, imagine if we were Tesla: we are the Model S. There will be the Roadster, so there will be something even better, but you will also see us coming out with the Model X, Y, and 3.

Do you worry about income inequality? We've talked about people just buying 55. You operate in a world where you see extreme wealth. I do as well. Do you share the concerns?

I do. The way I think is, okay, how do I democratize better sleep? If our product was $100, probably by now we would have sold billions—literally—because people really like the benefits of what we do. So it's our job as a group—an engineering group, even if I'm not an engineer—to make sure that we can keep reducing prices so everybody can get better sleep.

You said earlier about your co-founder, Alexandra. I hope it's okay. She's also your wife.

Yep.

How does that work most efficiently? What lessons do you have? What works? What doesn't work?

Yeah.

8. Working With Your Spouse

We have 2 different channels. One is Slack for work, and one is WhatsApp for private communication, for our life, and we never mix them. I might be screaming on Slack, “We have to get this done by the end of the day,” or, “Let’s review these at 9:00 PM.” And then on WhatsApp it might be, “What do we have for dinner? I’m craving pizza.” I don’t eat carbs. We cheat on Friday. Friday night is when we have pizza, but as a joke.

Second, I could talk about work all the time, literally 24/7. I love that, and it helps me. For her, instead, at a certain point she really wants to operate as if she were an executive that you wouldn’t bother after a certain time at night, like 10:00 PM. If it’s urgent, you can talk about that, but otherwise, if we’re on the couch watching TV, don’t just keep talking about work, because her brain needs to digest the information from the day. That’s how she performs.

But what I can do is Slack her. Sometimes we’re on the couch watching TV, I start coming up with ideas, and I start Slacking her. Her phone might be vibrating next to me, and I know that it’s me. It’s completely fine, and we don’t talk about it, even if I’m there writing a couple of messages.

And that doesn’t irritate you?

No, because I think the way she framed it was extremely smart. She says, “If I were an executive who wasn’t sitting next to you, would you call them for this thing at 10:15 PM?” You’d say, “No.” And she says, “So just treat me how you would treat our VP of Operations who is in New York.”

Would you not? I will call people at 10:00 or 11:00 PM—

Well, it depends on whether it’s urgent, a random idea, or something that we need to remember. If it’s urgent, I’ll call you at midnight, 2:00 AM, or 3:00 AM.

Yeah.

Trust me, I’m going to come to your door at 5:00 AM. I’m that type of guy. But if I just have an idea that maybe, for the next launch of the next product, we should talk about this in the video, I can just send you a note.

When was the most challenging time?

For the company?

For the scaling of your relationship in the company, because there are always breakpoints, you know?

In the early days, I think. Now, after probably 4 or 5 years, I think we’re really fine-tuned, partly because I’m extremely demanding. I’m a bit binary on things. I’m a weirdo, so I can be a husband on one side, but business-wise, there’s no mercy. We have to do what we have to do, and I can be the CEO if I deserve to be the CEO, and she can do her job if she deserves that job.

Where were you not demanding enough, where you should have been more demanding?

No, impossible. If anything, I do the opposite. I’m way more demanding than I would be otherwise. What I probably had to learn on my side in the early days is that when you’re so close to a person, you might act or behave in a way where you still expect the same things, but you’re not as professional as you would be with another executive who isn’t external.

I know.

Yeah. That was one of her points. She pushed me in the early days and said, “I have no problem with you being extremely demanding and expecting this by this time of day, but the words that you use and how you say it cannot be as if I’m your buddy. You need to treat me professionally, like an executive.” That’s where I had to step up.

I get in trouble for treating mine like an executive. She’s like, “I’m not an executive. Don’t treat me like one.”

For us, it’s to the point where I think Dalian and Keith, when they invested, didn’t even know we were married for the first year. Obviously, you disclose it when you do a round, so it had been disclosed in every round.

Ah.

But because of the interaction in the board meetings, they didn’t even realize that. You could ask Dalian. My brain works like that. I’m very binary on things. When I’m working, I’m working.

You know, I heard this brilliant statement the other day: “Vulnerability is sharing something that you’re scared to admit in spite of the consequences.” What do you think you’re scared to admit today, in spite of the consequences?

I moved to the US coming from Italy. I graduated in law. I didn’t know anything about Silicon Valley. I didn’t go to Stanford. I didn’t go to Harvard. The 3 of us are immigrants who founded Eight Sleep.

In the early days, it was very challenging because I didn’t know anything about that world, and I didn’t know anything about how the US worked. Thinking of creating a product that consumers would buy and love at scale, I had a lot of question marks about whether I could really do that. In the early days, there was this fear of, “Can I really scale this thing?” You can build a product, and 100 of your friends might buy it because they’re just nice to you. Maybe you sell 1,000 because it’s a crowdfunding campaign. But can you really build a true business where people buy the product because they want that product?

I love it, but what are you scared of today?

Today?

Yeah.

Do you know the story of when I had to move to China in the early days for manufacturing? I didn’t tell you?

No, I don’t think you told me.

It was after the YC Demo Day, right? We had just raised $5 million or $6 million, whatever. But manufacturing wasn’t happening, so we had all these beautiful prototypes. None of us had any experience in manufacturing. We thought, “You have a prototype, and now you build it at scale, and we’re done.” But things weren’t happening.

So I went to Alex and said, “I have to go to China.” She said, “Why?” I said, “Because manufacturing isn’t happening.” She said, “When do you go?” I said, “I’m going to go tomorrow.” She said, “When do you come back?” I said, “Once I fix manufacturing.”

I came back 3 or 4 months later. Even today, the longest-tenured employee in the company is a Chinese person I hired during those months while I was living in China.

And she just put up with that—3 to 4 months away?

Yep.

How did you do that? How did you make that work as a couple?

When the relationship started, she was living in Mexico and I was living in Italy for our first year, but that was probably 5 or 6 years before. For us, if the business requires that, you do what you have to do.

One thing that I’d be nervous of, or scared of, if I were you is the ways in which you work may not be transferable to having a child. Going to China for 3 to 4 months, you can do it. You’re a lovely human, and I really appreciate our friendship. I don’t think that’s the type of dad you want to be.

I think we would figure it out. We would brainstorm. That’s how it works at our house, right? We would brainstorm, and if I have to come back for a weekend and go back, I do whatever it takes. I go hardcore, whatever it takes, and then I try to do it in a smart way, in whatever way is possible.

We said before that, when it comes to travel, you can travel anywhere and stay in any hotel. What is the favorite hotel and the best place, and why?

I love the Maldives.

Do you not find it boring?

Here we have another problem, which Alexandra and I call “the gene.” We say we have the gene. I never took a vacation since Eight Sleep started. We didn’t even have a honeymoon because we set the date of our wedding to be exactly 1 week after the end of the crowdfunding campaign.

I get bored in any place for longer than 2 nights. We calculated that after 2 nights in a place, I start feeling like I’m bored. I’m thinking, “Let’s move to the next big thing.”

So what do you do in the Maldives?

I was literally there for a weekend because I had to be in the Middle East for work, so we just flew there.

So you took a weekend in the Maldives?

Mm-hmm. Yeah, because we had to go to the Middle East for work, and we flew Friday night. But what happened is that the guy who was leading hardware called me that Friday night at 2:00 AM and said he was leaving. I spent the whole weekend trying to save him because we wanted to save him, and I saved him.

I didn’t spend the whole time dealing with him. I had dinner and went snorkeling once during the weekend. But we dealt with the situation, and then we retained him.

How did you save him?

Because of our culture. The company was paying him way more, giving him RSUs, so liquid stocks, plus paying him probably 3X more. But he loved so much what we do, how we work, and what we want to build that, in the end, he decided to stay.

He literally decided 5 minutes before going into the conference room to tell his team. So it was out, and then he came to me 5 minutes before going into the conference room to tell his team he was leaving. He said, “I thought about that. Can you do this for me in terms of an offer?” We said, “Yeah, I’ll do it.” Then he stayed.

Can you advise me? I’m a founder of an early-ish-stage company, and my talent is getting poached by hot companies and top labs. Should I pay the same as what they’re paying to keep them if they’re great? Or do you have to accept that it’s out of our league?

Well, I’ll tell you something slightly different.

9. Building A High Output Team

I think you cannot even compare. If people are really comparing the options between a company at a totally different scale from you, they’re probably the wrong people. Or it’s not that they’re fundamentally wrong. In our case, this person was tired of the pressure at Eight Sleep. He does hardware, so he needs to go to China and Vietnam and travel all the time, and it was becoming a personal choice. But he’s a hardcore guy, and at the end of the day, he realized that this is what gives him energy. He didn’t want that life.

Sometimes it’s still happening today. Sometimes people say, “Oh, I’m at the final stage with Anthropic and Eight Sleep.” To me, that is a really bad red flag—not even for the salary, but because it means you’re confused. There is no way that these two jobs are in any way similar. I’m not talking because we are hardware versus software. It’s just, man, get your shit together. Do you want to work at a very large company that has no certain standards and probably a certain profile, or do you want to work at Eight Sleep?

But here, I’ll tell you another thing that we’re seeing. You will love this. There is another trend in Silicon Valley where there are people who have been laid off. Obviously, I don’t want to generalize, but we’ve seen this in the data. They start talking to a lot of companies. Sometimes some of these companies are listed with us, and they take one of our job offers. Then, 2 weeks later, they switch to another company.

The reason is because they probably didn’t have income or a salary for a few months. They want to try to get a salary or income, and then they keep certain conversations open. They might take another job.

Does that not look terrible, switching so quickly?

Well, yeah. But then they don’t even disclose it.

Do you think the Valley is too money-oriented? Chamath said on X recently that it’s become too transactional and too financial. From Chamath, that really is something. Do you agree with that?

Yes, but with a caveat. I think people who join a startup should be driven, and it’s important that they are motivated by potential financial success. I agree. But that success will come by increasing the equity value from X to 10X.

That is also why, to me, it’s so important. You cannot really compare us to one of these big companies that are already so big, where they are way more stable and maybe you do 2X or 3X. At Eight Sleep, you should come to try to do 100X or 1,000X. But the team size—there are so many details that are totally different. We actually want people who are very driven and ambitious, but they need to be driven and ambitious because of the right things.

Do you think people care more today about upside in terms of 10X or 100X, or actually just certainty of cash? Yes, it may be more capped, but you will get a tender next year, and that will be done as it is every year.

I think it’s completely fine, but that goes back to getting your shit together and understanding what you need and probably what your family needs.

Another thing that I learned as a CEO is that sometimes now—we just promoted one of our best guys to VP of Engineering. We were running a search for VP of Engineering, but he wanted the job. What I told him was, “Look, we will run the search, but you have your own shot, so prove yourself.” He did insanely well for 3 months, and then we decided to go with him.

I think it was very good that we ran an external search so we could see other people as well. I found that to be the professional way to do it. But what I told him was, “I’m going to give you the job, but I don’t want you to answer tonight. Go and talk to your wife, because she has seen how hard you’ve worked over the past 3 months. You were already working hard; the last 3 months, you went at 130%.

“So here, it’s not just you committing to this life. If I give you the job, I expect you—or I would like you, everything equal—to stay with us for the next 2, 3, or 4 years. Otherwise, I’m not going to bet on you. Go and talk to your wife. She has seen how hard you work, and both of you need to commit, because it’s not just you. It’s your family.”

Completely agree. I call it the power of pillow talk, which is why I will always spend time at a dinner party or a drinks party speaking to their partner.

Yeah.

Because I want them to actually know, at the end of the day, why I’m doing what I’m doing and how important my family is to me—

Yeah.

—and what we build is together.

Yeah.

And so when they come home and have a shit day, it’s like, “But I do like Matteo, and I know he’s a good human.”

Yeah. Exactly.

It changes everything.

Everybody has a family, right? So we need to take care of them, but they also need to be bought in.

Can I ask you, when we look at the team today, how big is the team?

We’re only 160 people.

Wow. That’s small.

Our revenue per employee is way higher than Apple’s. One thing I can tell you, without disclosing our revenue, is that other similar companies probably have 1,000 people at our revenue stage. Our output is 5X the average in Silicon Valley.

Can I ask you, when we look 3 years out, it’s a reasonable timeframe. It’s not crazy far out, but it’s a decent timeframe. How many people will you be then?

250 people making a billion.

Which function doesn’t exist today that will be very important, or which job?

We saw a change in email, but I’ve started thinking in terms of teams of 2. That is how I think about certain parts of the business. You still want 2 people to have redundancy, and you want 2 world-class people overseeing that area, but that area could be really big.

Right now, our paid media team makes hundreds of millions, and there are 2 people. It’s 200–300 million, just the group. The way I like to keep the organization is extremely small and flat. That is how we can be 160 people instead of 1,000, while similar companies are in the thousands.

So which function today, or which job today, will be gone in 5 years’ time, and which will be created?

Again, I don’t think anything will be gone. I think you can do what you’re doing with way fewer people, or the same people can be spread more horizontally to cover more areas. Maybe the AI SEO person oversees this other section and this other section, so you can be much leaner.

Now I have an AI internal tools team that didn’t exist until 6 months ago, and those are the guys building thousands of agents for internal use.

And you have a separate team for that. You don’t expect horizontal groups to do that.

No, because this team needs to be very connected to the data engineering team. The agents need to have access to the data backend and the data pipeline for everything we do. The marketing agents need to make sure that they have perfect access to revenue by country and CAC by country. Fine-tuning that is the real challenge, because you want to make sure that the agents are 100% correct.

Other than email marketing, what agent has had the most significant impact?

The one for paid media, right? Now we make hundreds of millions with these paid media agents.

The other big one is in finance. Particularly in these groups, that’s where we save a lot of headcount compared to normal companies. Probably a company like ours should have, I don’t know, a team of 20 people in finance. Our team is 4 people.

I really like to keep teams small and try to see if I can 5X the output. I’ve really loved asking investors to compare each of my teams and the quality of the output of each team to other companies they have, and to look at the difference in size.

You’re in 35 countries.

Yeah.

What’s the hardest country?

China, because you don’t sell on the website, so we had to reinvent everything.

10. Life Beyond Work

Dude, I want to do a quick-fire round, so I’ll say a short statement and you give me your immediate thoughts. How many hours of sleep do we really need today?

At least 7.

Biggest sleep tip for me.

Consistency and the amount of hours. You just nail those 2 things, and you will be good.

Eating before bed—any advice?

It’s very personal. For certain people, it makes a difference; for others, no. It will change as you age.

What have you changed your mind on most, in general, in the last year?

Probably in health in general. I think 95% of the value is just being consistent and doing the right things without going too crazy in terms of products that you can take, supplements, and all that. If you just have a very balanced life in terms of eating well, training, and sleeping, then the score will take care of itself.

What’s a kooky prediction, a weird prediction, you have about the future that you do stand by?

That kids who are being born now will never work, at least for money. They might do it because of their passion.

Can you just—

Yeah.

Explain that to me?

I don’t think that if a kid is born now, by the time they are 20 years old, they will ever work. By then, I think AI will be at a point where humans don’t work. They will do activities and social activities, even to help other humans.

What will we do then?

This is what we need to discover. I also have this pyramid of life about the importance of life, and to me, it’s a pyramid. At the bottom, you have health, then you have relationships, and then you have purpose. I think this is what drives happiness.

The first thing you need to nail in your life is to be healthy. Because if you are unhealthy, almost nothing else matters, right? If you have cancer and you risk dying in the next 2 or 3 months, you can’t be happy.

Once your health is on track, you focus on relationships. It doesn’t matter what kind of relationship. It could be a partner, it could be your family, it could be your friends, but you need to have relationships with other people, right? If you are extremely rich and healthy but completely alone and nobody wants you, you can’t be happy.

The third is purpose, and purpose is extremely important, right? Once you’re healthy and you have great relationships, you need to have a purpose in your life. You need to work toward something, and it doesn’t need to be financially related. It could be anything that you really enjoy, but you need to have a purpose. I think that is the part that we need to pay attention to.

What would you advise someone asking whether they should go to university today?

No. 100% no. It’s useless. If you want to have social activities, there is the social part, but I’m just talking in a very pragmatic way. If they want to have a career, particularly in Silicon Valley as entrepreneurs, I think it’s totally useless.

Do you believe in universal basic income?

I think it will have to happen, and I think probably, as companies get more efficient and need fewer people working for them, they will get taxed more to make sure that we can distribute universal income to everybody.

Do you think Bill Gates’s suggestion was right that we should tax agent usage and token usage?

The bottom line of a lot of companies will improve meaningfully over the next 3, 4, 5, 10 years, and so I just think we will need to readjust part of that bottom line to be distributed to people so everybody can have a comfortable life.

Would you let your children use social media?

That is a good question. I don’t have an answer yet, but at some point I will have to figure it out.

What do you not know yet about parenting that you want to know?

I’ll tell you something that I’m actually trying to do that could be slightly different. With Eight Sleep, we are lucky that we work with a lot of people who have been successful in sport. They could be ballerinas, chess players, or even great businessmen. I’m trying to talk to all their dads, and I want to learn from their dads what they did, what they thought worked and didn’t work in how they raised their kids, so I can learn how to be a dad one day.

What did you learn?

I’m just starting to do my due diligence and interviews.

God, that would be a fascinating exercise.

It’s amazing, right? Nobody thinks about it. It doesn’t need to be the dad. It could be the mom. I just want to learn what they think they did right or wrong for their kids to be successful. To me, successful could even mean being a doctor, right? I’m not talking only about athletes or sport. I want to learn from people who just went through that, and I’m sure they made mistakes.

You know what my mother did? She dropped the image of perfection, morality, or goodness that most parents have. You view your parents as good, always well-behaved, and generally—she would talk to me in depth about all of her fuck-ups and the lessons that she learned, things that you really wouldn’t talk to your child about.

Mm-hmm.

But in the depths of mistakes, you have lessons. How do I learn from her fuck-ups? Do you know what I mean?

Yep.

Most people would be like, “No, that was a dark episode of my life that I’m not going back to.” I really appreciate that in her.

Yeah. You made me think of something. I don’t remember the exact words, but I think Tony Robbins says that a lot of people who are very driven have always been trying to please someone since they were kids, and I think it’s one of their parents. He says, “You’re always trying to please one of your parents,” or maybe it might be slightly different based on childhood.

That is another thing. Particularly when I hire chiefs of staff, I always ask them this question, and I say, “You don’t have to answer me, but if you feel comfortable, think about that.”

Do you want to hear something even more specific that everyone gets angry at me for, but honestly, I don’t really care anymore? It’s actually much more specific than that, and I’ve spent a huge amount of time studying it.

Oh, really?

Most often, it’s boys and boys’ relationships with their fathers.

Mm-hmm.

It’s a broken relationship with their father where they’re trying to prove to him that they can be something, that they’re worthy.

Yeah.

That is how it most often manifests. Very rarely is it with the mother.

Yeah, it makes sense.

Really interesting.

Yeah.

Do you have a relationship with your father?

Yeah. He died, but I had a relationship with him. I still think he set the bar, and part of what drives me is also probably, if I had to guess, something to meet that bar. But I don’t know.

Did he see Eight Sleep become successful?

No. It’s funny because if you go back to when my dad died, I was still a lawyer in Milan.

No.

He wouldn’t know that I live in the US. He wouldn’t know that I’m in Silicon Valley. He wouldn’t know that I’m an entrepreneur. He wouldn’t know that I’m married to a Mexican woman. It’s funny because if you had the cutoff on that day, my life would be so different from what happened after that. I’m the same person but in 2 different worlds.

I’m sure he’d be so proud.

The early days were hard because, when I started becoming an entrepreneur, my mom didn’t want me to. My mom was a teacher in high school, and in Italy you make probably €1,000, something like that—€1,500. She didn’t have any means if I failed as an entrepreneur.

But I was doing well at the law firm, and so I knew that probably my boss would take me back if I failed as an entrepreneur at Allen & Overy. I took the risk, but I had nightmares for many years after that that I had to go back to the law firm.

What advice would you have for a young person in their career on taking risks? I was a law student too, by the way.

Oh, really? I didn’t know.

Because I was told that that was a secure life. We didn’t have that much money either.

Yeah, yeah, yeah.

It was like, “You know that you’ll do okay as a lawyer.”

Exactly.

What would you advise them?

We talk about this with Alex, my wife, a lot because we imagine this moment where I’m working. I come from a city called Ferrara. Ferrara is a city of 150,000 people in the middle of Italy, with a castle in the middle and walls from the 1600s all around.

Sometimes we joke about when she comes to Ferrara and we go see my mom. She says, “How the hell did you go from this city to the US and Silicon Valley, AI, and everything you do?” We joke about what would happen if you met a kid on the street now and he asked you how to get where you got. What would you tell him?

The funny thing is, I’ve thought about this a lot, but I don’t have an answer. I don’t know. I just kept moving things forward. I saw an opportunity, I went for the opportunity. I failed here, but that opportunity unlocked another opportunity through this connection.

It’s impossible to explain how you go from there. I didn’t even speak English until I was 24. I knew almost nothing about computers until then. After I graduated, I saved enough money with my first tiny startup—call it a startup—in Italy, and then my dad took out a loan to send me to San Diego to study English.

With that, because I graduated with honors, I was able to get into the big law firms. But even there, everything changed. I’ll tell you this story because one day my mom brought home a magazine. I was around 20 or 21—no, I was 20. It was my first year of college. In Italy, it was 4 years.

I was not a great student. I hated school. I was terrible. I started university with mid-level grades, but I didn’t like the idea of becoming a traditional lawyer in this small town, doing tiny things. I wanted something international.

She brought home this magazine that came with a journal called Il Sole 24 Ore, which is the Italian Wall Street Journal, right? The magazine was talking about these big law firms that were doing international transactions, IPOs, and securities.

I started learning about these law firms, and I discovered that there were 2 conditions for getting in. You needed to speak English, and you needed to graduate magna cum laude. In my typical fashion, I said, “Okay, if those are the 2 conditions, I’ll get it done.”

In Italy, the scores when you go to college are from 18 to 30.

I was averaging 23. From that moment on, I was getting 30, with magna cum laude on almost every single exam. I graduated magna cum laude. We took out the loan. I went to the bank with my dad, and they gave him the loan. I went to San Diego, learned English, got into Freshfields, then Allen & Overy, and then became an entrepreneur.

But why? I can tell you. We used to go to Chelsea Football Club every week, and we didn’t have that much money. We sat in regular seats that weren’t very good. This sounds really descriptive and weird, but I hated the smell of beer, and football stadiums back in 2000 were horribly aggressive. You could never pee at halftime because there were too many men trying to get in, and I was 5, 6, 7, 8.

One day, a friend of mine who was very rich took me to their corporate box, and it was beautiful. It didn’t stink of beer. It wasn’t aggressive and horrible. You could pee at halftime. Don’t laugh, but my eyes were opened to, “Oh my God, I hated it before, and life was so much better with money.” It gave me drive.

Where do you pin yours to?

Well, I think I always had that drive because I was doing a lot of sports before. When I was a teenager, I was playing tennis competitively.

But you’ve got to change your life to go from 23 to 30, get magna cum laude, speak English, and go to San Diego. Why?

I don’t know. It just clicked. It’s funny because, at least in terms of anything school-related, I never had that. But I’m the type of guy who, when I have a goal, can’t be stopped. I become a beast. I will outwork you. You can’t stop me.

Something clicked, and that is what happened back then. As for why, I don’t know. I just think I didn’t want to work for my dad’s tiny 2-person law firm, doing things in Ferrara.

Is that your greatest weakness? Because I, too, am like you, but that’s why I’m having a hip operation at 30. My shoulder is fucked, and my knee is unrepairable. I can’t run anymore because I ran 100-mile races so often that my body is just so broken. I’m a beast. I’m a broken beast.

It’s the scene. It’s what I was telling you before. I have a scene. I can’t stop. If you can put me on a boat in Sardinia, I’ll... I like what I do so much that the downside is I don’t stop. I get bored after a few days, and so that is why we call it the scene. Can’t relax, right?

Do you ever want to? One thing for me is that, as I lie in bed at night, my mind races, and it’s sometimes very lonely, alone in my head at night.

The people I admire the most—not in business, not people that you want to emulate—are really people that you might find in many places in the world. But I’ll call them Italian because I’m Italian: people who are at the beach. They’re just walking.

Actually, there was this guy. My wife and I were having dinner last week, and we saw this gentleman. We were in Milan for work, and he was having dinner in a pretty nice restaurant. He was there drinking his glass of wine. I don’t drink alcohol. He was eating a beautiful meal—I don’t remember what—and he was perfectly dressed, without his phone, alone, just thinking.

Obviously, I know nothing about the guy. But I just thought, I admire the guy so much. He was there treating himself, without looking at his phone, just thinking and enjoying his meal in what was, apparently to me, peace. That is something I admire in people because I struggle with that.

Matteo, listen, I so appreciate you being so open. I love conversationalists. It’s nicer the second time because you’re able to have a friendliness that you don’t have the first time. Thank you so much for being so amazing. This has been awesome.

Of course. Thank you so much.