$400M Investor Explains the Confidence Gap Holding You Back (ft. 20VC Harry Stebbings)

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This is about enjoying being punched in the face. I thrive off being hit in the face 10 times a day.

Harry Stebbings is the founder of 20VC, one of the world's most influential venture capital platforms and a leading investor with over $400 million under management.

We raised $70 million by WhatsApp.

$70 million. He's best known for building a global media empire through podcasting and has interviewed fed thousands of the most powerful founders and investors in tech.

I was broken early by life. I was kicked out of school for being bulimic. I'm an alcoholic. I feel like Madonna. No one will outwork me.

He's turned distribution into a competitive edge in venture.

I'm Harry stebbings, founder of 20VC, and welcome to the Burnouts.

You're obviously huge in VC. You have over a $400 million fund. You've had incredible unicorn companies. But you started the podcast. Was it in 2015?

Yeah, 2015.

And you ended up going to law school and dropping out. Can us through that and how you made that decision?

Yeah, totally. So I watched the Social Network when I was 13 and I saw Peter Thiel invest in Facebook and I was like, wow, I want to be a vc. You get to invest in amazing founders and change the world with technology. What a dream. So I thought, great, let's do that. Basically, I became the biggest nerd on venture. And When I was 18, my parents always say, take the job at the boring corporate, Go do the boring degree. But they were like, hey, go do law school. It's safe. It's a good career path. And so I went to law school, and then about a month in, I signed a deal with a law firm for $100,000. And I was like, I'm going to see how much lawyers get paid. And so I went to my law professor, I said, how much do you get paid? And he was like, 80,000. And I was like, oh, shit, I just made 100. And so I went and called my parents and I said, hey, I'm going to leave law school. Yeah, thanks. And they were like, great. We're having a dinner party and, uh, do you want to come? They just never, ever pushed me in any direction. They just let me kind of do what I wanted. The biggest mistake that people make is they just don't take the first step.

And how did you go about raising your first fund? I mean, the podcast at this point had gone viral. Was it through your own network?

Yeah, I mean, I just basically interviewed the biggest founders in tech, and then all of them were like, hey, I'll throw in 250. I'll throw in 250. And my first fund was at $8 million. So it was kind of pretty easy to raise. On the latest fund, we raised $70 million by WhatsApp.

Wow.

Yeah, I know. Which is like, just great. Founders. Every Decacorn founder will easily do a million or 2 million by WhatsApp. So, like, you can easily rack it up. And when you've done 3,000 shows, like, it's. It's pretty. Pretty easy to know everyone, and I.

Want to back up a little bit. So you watch the Social Network. That's what makes you excited about vc. Why not the founder route, though? I watched the Social Network and I thought, I am going to be a dropout. Like, I want to be a founder. I'm curious for you why you feel that made you interested in venture capital.

I actually think that building a venture firm is very similar to building a company. You have to do many, many aspects that relate to company building too. But I also love investing. Like, I love finance. When I was 9, 10, I was trading commodities and I just fell in love with finance then. And so, like, for me, it's this beautiful combination of, like, working with incredibly ambitious people, and then also the finance and the trading and the investing mind. The other thing is, like, I'm very adhd. I Get kind of very bored and antsy. Doing one thing every single day would drive me absolutely nuts in terms of like, same company, same company, same company. And so I just get this incredible breadth by doing what I do that I wouldn't get with company building.

I did see your parents saying that you were very interested in finance from an early age. So I'm curious also, when do you think that you became entrepreneurial in the sense that you were willing to go out and do your own fund?

And I started a different venture fund with. With Fred. Yeah. I mean, he's amazing, dude. And like that was a hard decision and that was a hard time. You basically get divorced. Yeah. I think you really. Whether you are actually looking to partner with someone as a room, I don't know if we're allowed to be personal as well, but I don't really do not personal. Whether you're looking to partner with someone romantically or in business, you want someone who's been broken by life. And I was broken early by life. I was kicked out of school for being bulimic. You know, I'm an alcoholic. And then I went through this breakup with Fred, my partner. And to be fair, he was amazing. I laughed and I caused all the trauma. And you know what you also learn? You learn that sometimes when you're young, you do stupid things. And I actually, I've never said this before, but I really regret how I left Fred. I left Fred and I was like, hey, I'm leaving and I'm going to do my thing now. And do you know what? The way that you leave a business or a personal relationship is how you're remembered. And leaving in a poor or ill informed or fast way isn't always the right thing. I could have been a lot more graceful and I regret not having more grace and elegance. There's. You learn. Only really in the shit do you learn.

Well, it takes a lot of humility to say that. So I think that's really, really important. And for those of our audience who don't know who was Fred, how did you guys get introduced? Like, how did that all come together?

Yeah, I mean, sometimes I think you have to have someone who really believes in you to kind of give you the accelerant to get you on the map. When I was 18, 19, I'd never invested before and, and I needed bluntly to leverage someone else to get on the investing track. He was a GP at Excel, which is obviously a big firm and brought a lot of credibility. And so I leveraged his credibility and his kind of investing status. And I think he leveraged my media platform and differentiators that other VCs didn't have. And so we both kind of had that interlock because we leveraged something that the other didn't have. And it was amazing. I learned a huge amount from him. The power of mentorship is so, so important. I'm sure you guys have amazing mentors, but if I would advise people on one thing, get a mentor very, very young. I've had one mentor throughout my whole career who I'm never allowed to say, which is an interesting one, but he's given me $50 million personally from all of my funds. Amazing guy. And decisions in life is what makes us. And he always gave me two bits of advice on decisions which I think are brilliant. Whenever you have a hard decision, think of one person you really, really respect. Okay, so for me, it's Pat Grady. He's the head of Sequoia. He's been my friend for 10 years. Why do I really respect him? Amazing husband, amazing father, amazing investor. The three things that I really care about in life. And anytime I have a really hard decision, I just think, what would Pat do? And whenever you have that person, you actually will come to a conclusion and make the right decision. And then the other thing is that you're never wrong to do the right thing. Most often you know what the right thing is, and often the right thing's the hard thing. That's why we don't do it.

What's something you and your mentor have disagreed on?

Whether or not we should be more in the US as an investing firm, it's a constant debate. We have great access in the US And I think we could do very well in the U.S. but then there's also a question of focus and winning Europe. I think he has felt that we have to be in the US to be relevant. Europe's a sinking ship and that we should move to the US Today. And I think I see great entrepreneurs in Europe every day. And I disagree with him that we have to be in the US to be relevant. But we disagree and continue to on that.

Do you think that there's a Persona of what a successful founder looks like, and are you able to clock that within the first couple minutes of meeting them? Or do you think that there's not a certain personality type necessarily?

There's three core traits that make the best founders, and I'm going to lose you straight away, but I'm just going to go for the hardest one. First, parental relationship breakdown. 90% of the best founders have a breakdown in some form of their relationship with a parent, a boy, a male founder. 90% of the time, it's a breakdown with their father relationship. That is one of the biggest signs of a successful founder, actually, because it generally leads to a chip on the shoulder, mega ambitions, you name it, desire to prove them wrong. 1. Gaming. There's huge correlation between high skills in gaming and high skills in entrepreneurship. Poby from Shopify always tells me that he puts a lot more emphasis on the clan that you come from, not the university that you come from. And then number three is you're moving around a lot in childhood. If you move around a lot in childhood, you're forced to make new friends, leave friends, join clubs, leave clubs, assimilate with new, different environments. Very much about what entrepreneurship's about. And I think the biggest mistake people also have is that we've, like, glorified entrepreneurship. You know, one of my best friends is the founder of Calm, the meditation app. And when I was fundraising and it was not easy at one point, and he was like, you don't understand. This is about enjoying being punched in the face. There are very few people that are like, I. Like, I thrive off being hit in the face ten times a day. Not like, oh, it's hard, but I'll get through it. Like, I actually relish it. But you have to be a masochistic. And I think that very few people like that. And with media and with TikTok and with all the glorification of entrepreneurship, everyone feels they can be an entrepreneur. And, like, everyone should not be an entrepreneur, very clearly. I think that's a big mistake.

Do you think that our stereotypes of what a successful founder look like are largely biased also by gender?

Because.

Because we have very few women, it's under 40 women who've IPO'd a company within the US and when me and Sophia were in college, a lot of times we wanted to start a company together. I had. I mean, I can count over 10 different professors that I really, really deeply admired and looked up to, told me personally to not start a business with Sophia, because the two of us have very similar personalities. We're both in respect, what you would call, like, alphas. We're both very social people. And the stereotype of, like, two co founders that worked successfully together in Silicon Valley is you two males. You have one who's like the tech guy who's internal facing, who's the ct, and then you have the CEO who's able to, like, go, riz and like, can raise money. Those three traits are those geared towards particularly male founders. Do you see that that parental rupture has to happen with women as well, or do you think it's different?

I think the more gender type one is the gaming one. That's just what I normally see when I meet founders. That's where kind of the dislocation happens. We spoke earlier that I think the biggest challenge actually when it comes to kind of female entrepreneurship and inspiring, it is actually that women feel incomplete and insecure when they don't have the final 20%. Again, we said if you have an audience of people, men and women, and they say, hey, I need this set of skills. If a man has 80%, he's like, I got it. This is my job. I'll just fudge it on the final 20%. Women go, same 80%. No way. I don't have the final 20%. I don't want to lie. I don't want to misrepresent. And it is that chasm of male overconfidence. And I would say actually, like humility from women that is one of the biggest problems. And I find that very sad. And I wish that women would actually change that. And I don't know. I don't know if there's something one can do other than say, like, hey, most of the time men are bluffing. And actually you're just as capable as men and you should absolutely go for it. One thing I always talk about, every single step of my career, everyone's been like, you won't be able to do the next thing. Seriously, I started a podcast with no money from a bedroom. You seriously want to become a fucking investor? You become an ambassador. You seriously want to raise your own fund? Okay, but it'll be a tiny fund because you're like a kid, okay? You won't be able to raise 100 million. Okay? You won't be able to raise every time. You won't be able to do the next thing. Only you set the boundaries of what you're capable of doing. Don't listen to other people. Number one rule, you shouldn't work with Sophia. Sophia shouldn't work with you. Why? You know who the most successful female founder I think is in this generation? I think it's Melanie at Canva. You know the setup. Her husband is her co founder. I thought that was meant to be a terrible idea. Another thing that's super fucked up about that. You know what? Neither of them are technical. Another cross in that box. Another thing that's Fucked up. They're from Perth. No one's from Perth. Anyone from Perth? Love you. Seriously, there are so many things that are anti consensus about this and that's.

The point of company building for so many young men. There are countless examples of extremely successful entrepreneurs, men who have raised hundreds of millions of dollars, IPO companies. And also for female venture capitalists, there's not that many examples of ones who are extremely successful. So as a young woman, of course it's difficult to imagine yourself being something that you have not seen for yourself. And I wanted to touch on something that you said around essentially having audacity. You had a lot of audacity through your career, right? I think there's a lot of grit that it takes to be able to look at someone in the face and say, give me millions of dollars. Especially for young people, honestly, irrespective of gender, that's a really difficult thing how to do even for us. I mean, when we were first pitching and raising like our first few million for our company, I almost felt like I was laughing at myself to, to want to have that audacity to ask people. But it was so interesting because so many of our other like male founder friends were like, oh no, we're going to go raise 20 million, 30 million. And they didn't even blink at it. It wasn't even something that they thought twice about. How do you think people can develop that muscle of being able to take themselves serious enough to make an ask like that?

Positive visualization is one of the most important things that you can adopt and learn. When you vis is something happening, there is a greater chance that it will happen. And so most people go into the meeting thinking, God, I hope I don't fuck up. I hope I don't get asked that question. I hope I don't do this, I hope I don't do that. Don't do that, Harry, don't do that. And then of course it happens. I never imagined that it would not happen. It was never possible. And so for me, like when you have that unwavering naivety but also confidence, it was just never an option that it wouldn't work. And I think people need to have that quite black and white mentality.

And where do you think that came from for you?

I feel like incredibly nervous going and sitting in a room with 30 year olds. Like when I get like a housewarming party now with 30 year olds, I'm very nervous. There's not much that we have in common. I don't know what to say to them. I just find it difficult and uncomfortable sitting down with the CEO of Visa for dinner. Not a problem at all. I've got no idea about payments, but fuck it, I'll have a good chat with them. And so it's a weird one where it's just like. I think I just have always felt much more comfortable with people who are older than me. I was a kid at school who at break time would stay with the teachers because they were more interesting than the students. I don't know where it's come from, though. Maybe I should ask my therapist. I think therapy is very important. By the way, most people in the UK are very ashamed of therapy and it's like therapy is like a gym for the mind. And I think most people also go to therapy when it's like, oh, I need help. And it's like, no, you should go to therapy. Just generally speaking, you don't go to the gym just when you're out of shape. You go continuously to stay in shape.

What are your thoughts on therapy, therapy versus, like, executive coaching?

I don't particularly. I don't. I mean, executive coaching can be kind of helpful if you have, like, another legend that is coaching you, but, like, the whole, like, exact coach who's never actually been an exec. I mean, it's just kind of useless.

I think it's a cheat code for having a mentor. Like, it's literally just a paid mentor, which doesn't make any sense.

Yeah, the paid mentor is a big red flag for me, honestly. And so I don't like that at all. I hate the career coaches. We say a la poo Bell. Like the worst? No, terrible. Like success coaches. All of this crap. No.

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For mentorship. It was really interesting. We had a guest on who we were saying that we, we've both been very lucky to have incredible mentors. And he said that he actually disagreed with us and that he would not encourage people to seek out a mentor because he said that it was inherently kind of a privileged thing to say because you have to be worthy of having a mentor or like there needs to be a reason that someone wants to see value in. And he said that it was a cop out to say that because then it's like you sit around waiting for someone to mentor you versus going out and like taking your own initiative, which was really interesting. I had never heard that perspective before, so I'm curious what you would say to that.

I think it's like it's not that black and white, which is like you can go out and do things and that's the biggest problem. Most people don't know what to do, so they do nothing. Activity, drives, outcomes, just do a lot of shit and at the same time have a mentor. It's not like sit back and wait and wait for mentor to tell me do both at the same time. People get it wrong. In the world of like the Internet, it's pretty easy to get in touch with anyone. And so when it's easy to get in touch with anyone, the way that you communicate to them and ask them to be a mentor and build that relationship's easier than ever. I cold emailed Marc Benioff 53 times before the guy responded. Every week I would send an email at the same time on a Sunday evening and I would research him and find out his favorite whiskey, his favorite holiday destination, his favorite food type. And I put it as a PS at the end and I would a B test it to see what worked, what didn't work. Obviously, obviously nothing worked because he didn't fucking respond for 52 weeks.

Wait, what was the one that actually worked?

I think I said about like a McAllen whiskey, like 75 or whatever, and he was like, ah, good one. That's my favorite. Yeah, I'll do your show. And then by the way, that was the thing. That was the thing. And then do you know what people also really don't understand, which is chain reaction of content. Okay, you get that. Do you know what I think straight away, Tweet, fucking goldmine. I'd sent Mark Benioff 53 tweets and it was this, sorry, 53 emails. And it was this email that made this hundred billionaire come on my podcast. That's a great tweet. You're going to get super, super engagement on that. And I think most people create one piece of content and they don't think of the multi package that you have. So here, like with every show that we do, we create 60 to 70 clips, 20 for each different platform, different hooks, different fonts, different colored fonts, different intros, different music. People don't think enough about packaging the same content differently.

Can you please tell us about your clipping army of different people and what you do with that?

Yeah, people need to actually segregate their teams by channel. And this might be too inside baseball, but for anyone who wants to build a brand and wants to build content, you do need to think like this. Because if you don't have teams, you need to compartmentalize your brain. So TikTok does specifically very well on stories and you need actually like slow and lingering music. Certain font types work better there. Instagram reels maybe is a little bit more Entertainment and fun. YouTube Shorts is a lot more academic and structured in terms of frameworks for lessons. And so you need to have different skilled people for different channels because the content's entirely different. And when we separated our teams to specialize on a per channel basis, we really saw engagement go through the roof. The other thing that is really important is to have a test channel and to have like a formal channel. And you're like, what the fuck does that mean? So TikTok doesn't actually really give a shit how much you post. You can throw shit on TikTok and you can just see what works and what doesn't. But actually if you go on YouTube, they're going to denigrate, downgrade you if you just continuously post. And so what we do is we put a shit ton on TikTok, we measure and test it and then we take what works on TikTok and put it on our Instagram and YouTube because that's a lot more judicial on how much you actually post.

Well, it's really interesting because distribution has now become a moat in a way.

Everything.

It's everything in a way That I don't think people really thought of it that way in years prior. So I want to understand. This is something we talked about before. When you onboard or start working with the founder, you have them as a portfolio company. How do you help them with their content strategy? Like, what are the biggest pieces of advice that you give them?

Great question. Sorry for going off on a tangent, but my brain is weird. We basically looked at our numbers at the start of this year and they were actually flat. And I was like, we're fucked. By the way, no one gives a shit about storied founder being like, let me tell you about the founding of this company 10 years ago. No one gives a fuck. Even if it's a massive company, we want one of two things. We want news, which is commentary and analysis, or two, we want AI. It's the only show we want right now. And so we completely reoriented our shows. Monday is AI, and then Thursday is news and analysis. And the person who does the news and analysis show with me is like a 55 year old OG VC. He's super smart, this guy Rory. Fantastic. And I'm like, rory, why did you do it? And it's because he's like, you beat me to a deal. And let's be honest, I've made billions of dollars for my investors over 30 years. And you have a fricking podcast. And that's the point. That's the power of distribution. Where like it so driving founders decisions on who they work with. And so how does it look like when we actually work with them? Honestly, it's understanding very clearly what metric are we driving, which is one of three things. We're either driving customers, we're either driving talent, or we're driving future fundraising. And then we work together to create content maps which we can align on, which aligns to those. So if we're working on, say, talent acquisition for them, I will start thinking about how we can show the life inside that company in a really cool and compelling way for future talent. If we're looking at future fundraising, I'm going to be like, give me fear charts, which are up and to the right. Give me revenue graphs that make us look amazing, you name it. And then I'm going to post about you being one of the fastest growing companies. And so we very much tailor it to what you're looking for in that way. But like, you know, we have this company and I posted on LinkedIn about their revenue growth and they got 4.5 million in error from one LinkedIn post.

Wow.

Like, if you think about like choosing a VC, honestly, most VCs are kind of the same. If one of them's like, hey, I'll bring you like a mega distribution channel and 4 and a half million in revenue, you're like, shit, I'll take you. That's really helpful. And so I find distribution is driving so much of founders choice on which VC they work with.

I'm curious, do you think it took a while for people to understand the value of your platform or was it really instantaneous?

Oh, my God. I was told for years, like, you'll never be able to do VC and podcasts. What's a podcast? That's so stupid. Well, I was offered jobs in the early days and they were like, we'll only give you the job if you stop the podcast. And I was like, I'm only valuable because of the podcast. Yeah, like, if you thought I had iq, you're sorely mistaken. Like, it's just charisma and charm at this point. So, no, I think people still dramatically underestimate it. And that's like, why I think we're going to win. Like, you know, I will invest 4 million this year into content alone. Like, I don't know if you know any other venture firm that's investing 4 million into content just to be the number one content provider, probably Andrewson. You know, the biggest mistake people make with content as well is they're like, and this really upsets me. Oh, I so want to build a brand. I so want to do content. It's just not me. And I'm like, okay, this is like going to the gym for the first time. Who sees the treadmill and they're like, oh, hello old friend. I feel so at home. I don't know how to work. All these buttons incline. No idea. But you, you're wonderful. No one ever does that. It's painful. I remember I was a very fat kid when I was younger. They called me Augustus. Children are cruel. And I went on the treadmill for a kilometer and I actually went outside and threw up. Like, I was that out of shape. It's hard. It's meant to be hard. But you do it again and you do it again and you keep showing up and you get better and better and better. And, you know, I was terrible when I started. I sounded like a BBC presenter from the 1950s. Hello and welcome to 20 VC. And now I've done 3,000. You know, I was speaking the other day at something, there's like 5,000 people. I didn't prep. I didn't do anything. You just rock up and just go for it. It's like you have a playbook and you can keep it running. And so my point being, like, too many people think that everyone starts perfect. Not seeing that, actually, in the early days, they were terrible too. You just didn't see it. It's the other thing that's great with content. If you fail, doesn't fucking matter because no one saw it. It's okay. That's why it's such a good business.

Different people are meant for different kinds of content too. The reality is, like, if you're messy, you should be on TikTok. That's your channel. If you're really, really good at writing like Sophia is, you should be. I teased her relentlessly through all of college because she would offer me LinkedIn merch. And I was. There was no way I was wearing that outside of our dorm room. I still say, please don't wear that to the office, dear Lord. But, like, we're all yappers, right? Like, I assume you could be at a table and talk for hours, and there's an intimacy of being on the microphone and someone actually choosing to, like, listen into that podcast. That's not the same way of, like, if someone chooses to follow you on Instagram, like, sure, they see you while they're scrolling through their feed. If I take an hour to listen to your podcast in the morning and I'm hearing your voice, you don't need to adapt to all the different kinds of content. Like, you can be a huge substacker without ever putting your face anywhere. Not being a tiktoker. You just need to figure out what your vertical is.

I would just say specialize. The most important thing is finding your first. A thousand true fans. Great article by Kevin Kelly. A thousand true fans. Anyone can build a great business. If you have a thousand people who just love everything that you do and too many people do a show for entrepreneurs or for, I don't know, CEOs, whatever it is, be very specific. Target fintech founders who are pre IPO, but post series C, get a thousand massive fans who are specifically listening to that segment. Always expand from there. Start niche, expand from there. Especially in a world like today, discovery is the biggest problem when it comes to content. I think what you're going to see over the next 10 years in media is more value accrued to the incumbent brands because discovery becomes such a problem that people actually just revert to the brands they know and trust. We see this today. There's so many VC shows that actually most people just go, oh, fuck it, I can't figure out which one to go to. 20 VCs been there for years. And I think you see that actually in incumbent media brands where value cruise because discovery is such a problem that people revert back to what they know.

You've talked about yourself as less of an operator, more as like an editor and a curator of finding the best people to do different jobs. How have you grown your team over time? How big is it today and what mistakes or learnings have you had as you've done that?

It's a very good question. You know, I, I didn't expect to enjoy managing people, but I actually really do. I think one of my biggest lessons has been don't respond in real time. There's so many times when you're like writing a message back and you're like, like, oh. And so I always make sure to remove the emotion out of the room. And actually when you go back and ask yourself what is the worst that happens from this? Very rarely is it actually that bad. You know, we talk about one way and two way door decisions. Most things are two way door decisions actually. And so I'm always trying to be as calm as possible. The energy that you bring to the room is the energy that someone else will give you. It's the other thing that you learn about personal relationships too. If you tell me something, I've had eating disorders when I was younger. If I say to my partner, hey, I feel really self conscious right now, I feel bloated and I just hate my body. If you go, well, you look fine, don't be stupid. I'm not gonna come to you again with something that's a bit sensitive. If you go, I'm really sorry, why don't you tell me a little bit about that and I'm here, I'm gonna come to you with more. The energy that you bring is the energy that someone else will give. And so in terms of team 100%, it's been a hard lesson if I'm honest. We work very hard, like unwaveringly hard. We're definitely the hardest working team in Europe. We espouse996 and people either opt in. Also, big problem that people make, they don't have opinions around the culture. Like, we choose people who want to work unreasonably hard and make a huge amount of money. If that's you, then you should join 20 VC. If that's not you and you want a weekend and you're happy to make less money. You should absolutely not join 20 VC. I will text you at 1am I don't agree with like not texting and not working hours. And so we have a very clear opinion around the culture that we build. It's a bit like a cult and that's important. And I think where I've made big mistakes is where I've gone. You know what, I know that they don't fit that, but they're really good at X role. I can teach people most of the skills that they need to be successful. I can't teach them the mindset in a lot of cases. That's been a big lesson for me.

How do you feel like you motivate your team? What are the biggest drivers of inspiration and people working really hard?

Yeah, I think you have a couple of different levers. You have like progression, you have cash and you have title. And I separate them always. And why people need to be continuously drip fed. Some form of advancement, some form of well done. You did a great job. And so if I say well done, Safiyeh, I'm giving you a promotion. With that promotion comes a pay rise. And our numbers are looking great, amazing, like dopamine head fucking great. But that's all at once now. I'm kind of out of tools to use to inspire you. Next month. If I Sofia, if I say, Sofia, you did amazingly well. I'm going to promote you to that head of content. You're like, yes, I get a great title promotion, I can put it on LinkedIn. My family are proud of me. Then next month I tell you about the pay rise. Yes, I get your continuously drip fed progression in a way that makes you continuously feel like you're advancing. You have to use these different assets as kind of weapons to help people feel like they're progressing continuously.

What's your longest standing employee?

Five years.

Okay. And how did you find them?

For my sins, I smoke. And so Americans are like, oh my God, no, none of you Americans smoke. It's very funny. And I met him at a VC party and we were the only ones smoking outside. And he sent me a load of deals and I was like, this guy's an idiot. What an idiot. And then those deals went on to be billion dollar companies. And I was like, maybe I, I would see it, you know. And so he then invested in my fund and I was like, do you want a job as well as like investing in my fund? And he was like, yes. And so he joined five years ago.

That's Amazing. Something that I really appreciate about you is that you said that you invest in people, not ideas. And I was. I was reading like one of your tweets where you were talking about how you had missed out on different opportunities.

Oh.

Oh.

Do you know what I found? I found out. I actually run the numbers. Yeah. I would have made more money if I'd just invested. Invested in every single founder that I'd ever met. So. Every single person I met. Here's a check. I would have made more money than like, me picking. Yeah. Yeah. The founder of Deal2 million on like a 10 million price. It's now a $19 billion company. Time and time again, I've missed great companies because I focused on the market, not on the.

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What's the biggest fuck up you've ever had in terms of a deal? The one that keeps you up at night if you had to pick one that you missed.

Number one is deal that 2 million on 10. I can have put in 3,400k and got 3 or 4% of the company in an 8 million fund. I mean, if you think about that today, that's a $450 million position in an $8 million fund. So I'd say that 11 Labs which you know, is a $10 billion company or soon to be $10 billion company. We could have done $25 million seed round there, done like 1 or 2%, but that would have been a $300 million position. Yeah, I definitely fucked up those two.

And was it because you didn't believe in the idea, but you did think the founder was interesting, or how did those play out?

And this is the biggest lesson. I thought the founder was amazing on both. I just didn't like the market. And 11 labs, I'm like, voice AI OpenAI are gonna do this. Come on. This is like the most obvious play for OpenAI, obviously. So Matty's amazing, but no. And this is actually something that I use with LP. When I was fundraising for this last fund, two LPs turned me down. And I emailed them and I said, hi, Dominic. I have lost two decacorn founders because I knew that they were brilliant, but I turned them down because of the market that they were in. You are turning me down because of the market that I am in. And I am urging you not to make the same multi billion dollar mistake that I have made. Have a think about it and I'll give you a call tomorrow morning. And I called both of them the next morning and both of them invested 5 million bucks. So it was $10 million that was through, like absolute. And because they were like, I 100 believe in you. I just don't like seed. In Europe. I don't like Europe. I don't like seed. Whatever it was, and they're like, it, I'll do it.

Why did you still want their money?

Oh, I can convince you that you're wrong. Like, also, most people have to sell to someone else. That's another thing. You have to equip people to sell to their team. And I think in the cases where they really wanted to do it, it was just a case of they needed that extra push to get over the line. Another really important thing that I learned is the power of pillow talk, which is like, I don't know if you've ever seen Hitch, brilliant movie. But Albert Brennaman, when he goes to the gallery, the most important thing is not that the girl that he's chasing likes him at the gallery, it's that the friend Maggie likes him. And it's the same thing in business, actually, which is like, if someone brings their other half to a dinner or to a whatever it is, event, I will make sure that that other half, husband or wife, leaves going, harry is awesome. Harry is so great. You should work with him because he was so fun. The power of the car ride back or the discussion you have when the lights are out with your partner is the one that will govern the decision that you make.

Well, it was funny because one of our podcast guests said, people over complicate business. People just need to like you. It is that simple.

10,000%. Like, honestly, people want to do business with people that they like. Why do I do the PS to Mark Benioff McKellen, 75. Because it adds humor, it adds personality. You know, we send LP updates to our LPs, the biggest institutions in the world. Literally, I've a B tested sending without a picture of my mother and me walking a marathon and a PS about it it. And with. When I do it with a picture of me and my mother, we have a 92% response rate. When we do it without, I have a 61%. It's a noticeable drop. And we've done it across 12, 12, 6 and 6. And so you've got a good data there to suggest that there's like a meaningful, meaningful uplift. Why? Because people see it and they resonate. It's different. You also always want to be a purple cow. You know this, like, if you drive past a cow, you're like, whatever, I've seen a cow. If you drive past a purple cow, you're like, holy shit, that's different. It's sometimes better to be different than it is to be better.

And it all comes back down to the people you're talking to are just people. In the same way, your friends like you because you're funny and interesting. People in business will also think the same way about you. And I think people forget that sometimes and they're overly professional in a way that turns you off.

Yeah, I mean, you know, one thing that people say to me a lot now is just like, I'm very surprised that you talk so openly about alcoholism and bulimia. And I'm like, yeah, it's very important that I show my full self. And you don't just see this, like, glossy image of managing lots of money and everything being a success. It has not been easy. And I think one of the most sad things right now is there's this huge amount of young men struggling with eating disorders who don't feel that it's okay to admit, who don't feel that it's manly. And I think it's important that for people like me who've had it and got through it, you talk about it and actually it Makes people resonate.

Where do you think you learned these people skills of you're obviously charismatic, people love you. Where do you think that came from?

I wasn't charismatic. I used to go to the bathroom at break time when I was at school because I didn't have any friends and I didn't want anyone to see that I had no friends. I had no idea how to talk to girls. And I just felt very uncomfortable talking to girls, which is why I went to a different school where girls were, because I was at all boys schools before that. And so I learned again, it's very kind you say that, that, but I learned it over 3,000 shows. And I say that because I think it's encouraging to other people who feel that's not me. You can literally develop these skills through continuous repetition and putting yourself in uncomfortable positions that you don't feel ready for.

What are the biggest things that you've learned about communication?

I think there's a couple, but like, number one, people open up when they see vulnerability in you. And so there's a couple of things I'll do before a show to make someone feel like they can open up up. Number one, I'll ask them for advice, especially men. They feel empowered when you ask them for advice, and suddenly you see them much more willing to share more and to give more because they feel like they're in a position of superiority. And then, number two, I will talk about bulimia, alcoholism, my mother's ms, you name it. Because you break the barrier of comfort where most people don't go that quickly, and they're like, wow, he's really opening up. People really engage with that. And so I'll do those two things pretty quickly.

And how do you keep in touch with people?

WhatsApp is a secret weapon. I'm trying now to build an integration where, I mean, who uses Facebook anymore, seriously? But like, the notifications for people's birthdays, it's the best thing about WhatsApp. And so I'm building an integration which basically triggers a WhatsApp message to the person, person. And so it says your birthday on Facebook, and then it sends a WhatsApp with a template response like, hey, you know, Sophia, happy birthday. Hope you're celebrating in style. Always let me know when you're in London. And then everyone gets that from me. Because my job is to productize network in a way that no one else has done. And that is a very secret weapon to do that. WhatsApp is how I build that relationship with people, though, at Scale.

Because what did you say you raised $17 million just off of WhatsApp? 17 $70 million off of WhatsApp.

Literally pacing around my gym in between sets.

What are you saying to people?

Yeah, dude, I'm gonna raise the new fund. Would love to have you in, let me know if you're game. But it'll be a lot of fun to have you with us.

And then how do they usually respond? Any diligence? Anything?

No, but yeah, like, count me in for a million.

Hey, dude, what's the largest check someone has said over WhatsApp?

10.

10.

10.

So you send them a fun message, they come back, they're like, like, count me in for 10 million.

Yeah.

Wow.

How did that make you feel?

Yeah, that was pretty fun. It's years to get to that point of relationship building, but yeah, you feel pretty, pretty good about that.

And why do you think people trust you so much with their money?

I'm like going to die on this fucking hill. Like, no one will outwork me. This is a game of who can survive the longest. Content's very easy, actually. It's a game of who can survive the longest. You know, 11 years ago, no one gave a shit for four years. We did not get over a thousand plays per show. Most people would just give up. We didn't make money for three is again, it's just about showing up continuously, continuously, continuously. And so why do people trust me In a world of like very, very commoditized venture capital. You guys have met VCs, they're all kind of the same.

So a lot of them are Excel monkeys.

Yeah, they're Excel monkeys. They're all kind of the same. I'm completely different and we have a very different offering. And so when you're thinking about how do I build outsized returns in the portfolios that we have as an endowment fund, as a foundation. Fuck. I want Harry and I want 20 BC because it's just totally different. That's going to bring stuff that we don't normally see.

So that makes people trust you. How do you know when you trust someone else?

Oh, I can trust someone pretty quickly. My job is to read people. We joked before about, like, oh, I don't take notes and I'm very people oriented. Like, my job very quickly is to read you. And like, there are questions that I will ask that really get to that I talk to him about your relationship with your sibling. How you describe your relationship with your sibling is a very clear indicator of how you think about yourself. Talk to me About a time you really doubted yourself and all hope was lost. These moments really reveal a lot.

What kind of answers do you look for from people?

Real self reflection. Like the worst answers. Like, you know, when we're super busy and I just don't know what to do with X or Y and time management. You know, I remember when I was very, very bulimic when I was 16 or 17, and I would make myself so sick that I would pass out. Like, that's a moment when you really have to look at yourself in the mirror and question, like, this is really damaging someone. Being able to talk about that and having the humility and confidence will tell you a lot about how they engage.

I understand why it makes people trust you and you're able to be so open. And I'm curious if you think that the founders that you invest in have that same ability to really emote and be open. Because to your point, I mean, so much of this is about being able to just be punched in the face over and over again, again, and kind of to be like an army soldier and just let it roll off the back. And I would say that probably makes it harder to open up or to be able to weather a storm. You have to have a shield up. So I'm curious, like, how you think that plays out in the founders that you invest in.

Yeah, I think honestly, it can do one or two things. It can give you the shield. It's like I can't open up to anyone because life is hard and you get continuously hit. Or it's like, actually I've been hit so many times that I'm willing to open up completely because I've kind of been so broken before. And I actually, I think it's. It's quite a helpful thing where, like, my job is to. To detect it in people where it's not obvious and then help them tell stories. Storytelling is probably the greatest lost art, and it will continue to be in the world of AI. I think this is the greatest worry that I have. Or one of the big worries I have is that in the world of AI, we just lose creativity. There's two types of people. There's Walt Disney, which is like, tell me a story. Most often very early. And there's Jerry Maguire, show me the fucking money. And it's actually easier to be show me the fucking money. Because you just show the data. But actually telling a compelling story much harder. I work with founders a lot on how do we tell compelling stories. So to your point there, no, very often they don't feel comfortable sharing it, but my job is to package it in a way that people want to buy it.

What are your goals for the future, for yourself?

Oh, I feel like Madonna every single day. There is new, fresh content that is different, different formats, different guests. I have to continuously be better and continuously reinvent. We have to do news shows, AI shows, different formats, because if you don't, you will die. Like, I am the most self conscious, nervous person in this business and I think you have to be. It goes to the Andy Grove book. Only the paranoid survive. I am freaking paranoid all the time and I spend every single day at 1am I go down, admittedly with a cigarette or two, and I watch TikTok for 20 minutes, Instagram for 20 minutes and YouTube for 20 minutes. And I make notes on what works on each channel and then I send those notes to our team for the next day so they can take it in, learn, agree, disagree with me. But we constantly have to be assessing what everyone else is doing and seeing what works.

So do you keep tabs on your competition?

All the fucking time. The biggest way to piss me off is when they get someone who I want to get, which honestly can happen quite a lot.

Who do you think are your competition?

I would say very clearly invest like the best. And I would say Jack Altman's podcast. Honestly, I find the rest just pretty freaking dull. I really want good content and then I just end up listening to Taylor Swift because, like, there's just not many good podcasts today, I find. And people also don't understand the science of podcasts, which is that in the first three minutes you need to get to a lesson. You'll see a 68% churn rate if you don't get to a lesson in the first three minutes. So do you know what every podcaster does? Oh, tell me about how you started the company. Fuck. Three minutes of like, you know, you talking about your college days. No one cares about your college days. You want, hey, what is the single biggest advice for someone starting a content brand today? You've got to specialize. Like, you have to have a lesson in the first three minutes.

Well, people also have such short attention spans nowadays that if you have any fluff in the beginning at all, there's no way they're even going to get to the value portion, which is why hooks are so important. But also something that has been really interesting for me listening to you talk, is that you are clearly extremely data oriented when you have a statistic for everything. You AB test so many different things. How did data become such a big part of the work that you've been doing?

I didn't start like this. I learned it over time. The defensibility a company has is in the thousands of little actions and processes that make you who you are. It's not actually the main thing. It's the lots and lots of little things. And so when did I learn it? I learned it over time, bluntly, by speaking to every single person that I. Every single person at a drinks party. I asked them, what podcast do you listen to and why? And then what podcast do you hate and why? My mother at Christmas drinks parties that. Harry, please, not the podcast question again. And then I just study the data, and the data is pretty easy. You go onto YouTube, you go onto your RSS provider, and you just study the data and you just. A B test.

This might be an awkward question, but if you have a founder, one of your portfolio companies, who is underperforming, the company's not doing well, what is that relationship like? What do you usually say to them?

I'm very direct, and people always know that with me. And I think the other thing is, like, if someone's company's not performing, if you're feeling it as an investor, you have no idea how much their feeding it is a foundation founder, and you never know what battle someone is going through. Be kind. The job of an ambassador is to be the cheerleader when things are really bad and to be actually the critic when things are really good. You need to neutralize the person when it's shit. I need to inflate them and bring them up because they need to inspire their team. They need to inspire their customers. And it's really important that you're a neutralizer, a not a double negative.

Any last pieces of advice for people who are starting businesses today?

Take the first step. Most people do not take that first step, and that's why they're not successful. And then another thing, which I always remember my mother telling me, which is like, I don't know if, you know, Gone with the Wind. You're probably too young. Okay, good God. Like, you know, tomorrow's another day. And it's like, no matter how bad a day today was, which it will be really hard and shit, tomorrow's a new day. And when tomorrow is a new day, that's yours to make of it. And you have to continuously wake up with fresh eyes to make the most of every day.

Okay, Harry, thank you so much for coming on the burnout today. This was such a Pleasure.

We love you to do it in London in person.

And thanks for having us at the new studio. It's beautiful.

Awesome.

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