Harry Stebbings, Podcaster and VC

2 Nov 2025 · 1 h 17 min

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In short

Podcast Summary: The Gentleman‘s Journal Podcast - Harry Stebbings, Podcaster and VC

Episode Overview

  • Host: Joseph Bullmore
  • Guest: Harry Stebbings
  • Release Date: [Insert Date Here]
  • Description: Harry Stebbings shares his journey from being a precocious 13-year-old inspired by *The Social Network* to becoming a successful podcaster and venture capitalist with his fund, 20 VC.

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Key Themes and Discussions

Harry Stebbings’ Early Influences

  • Harry was inspired to pursue venture capital after watching *The Social Network* at age 13.
  • His unique aspiration set him apart from peers who aimed to become tech founders.

Podcast Beginnings

  • Launched his podcast, *The Twenty Minute VC*, at the age of 18 with a modest budget and no contacts in the VC world.
  • The podcast became immensely popular, leading to 1,400 episodes and the establishment of his own VC fund.

Transition to Venture Capital

  • Harry founded 20 VC, which has backed 13 unicorns, showcasing his success in the venture capital arena.
  • His approach combines meeting people and understanding them deeply, focusing on making others feel comfortable.

Personal Development and Mindset

  • Discussed his strict work ethic, working nine-to-nine, six days a week.
  • Reflects on how a lonely childhood and experiences with eating disorders shaped his entrepreneurial mindset.
  • Emphasizes the importance of authenticity in building a personal brand.

The Dangers of Social Media

  • Harry cautions against the effects of social media, particularly its addictive nature and its impact on mental health.
  • He expresses concern for the younger generation's relationship with social media and its potential harms.

The Future and Optimism

  • Harry has optimism about advancements in AI, particularly its potential to address incurable diseases.
  • He believes that AI will bring significant breakthroughs in healthcare within the next decade.

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Key Takeaways

  • Personal Branding: Everyone should work on their personal brand, despite initial discomfort.
  • Authenticity: Authenticity is crucial in leadership and personal branding.
  • Mental Resilience: Harry's success is attributed to his resilience and ability to confront challenges.
  • Importance of Relationships: The quality of personal relationships plays a fundamental role in happiness.
  • Work Ethic: A strong work ethic is essential, but it’s important to balance hard work with personal well-being.

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Quotes

  • “You have to be unwaveringly obsessed.” - Harry Stebbings
  • “Most people fail because they quit.” - Harry Stebbings
  • "The work you do in private is what you are rewarded for in public." - Harry Stebbings
  • “Invest in the person, not the idea.” - Harry Stebbings

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Conclusion This episode of The Gentleman‘s Journal Podcast provides a deep dive into Harry Stebbings' life and philosophy, revealing how his unique experiences and fierce work ethic have led to his success in venture capital. His insights into personal branding, resilience, and the future of technology are both thought-provoking and inspiring for aspiring entrepreneurs.

For more information on Harry Stebbings and his ventures, check the full podcast episode.

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Transcript

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0:00This episode of the Gentleman's Journal podcast is brought to you by Lin, the long time maestros of exceptional home audio and makers of some of the most emotionally impactful impactful speakers. imaginable. A few weeks ago, the Gentleman's Journal team headed down to Lynn's specialist Ripcaster, what a great name, just outside of Henley, and were almost literally blown away by the ridiculously crisp and clear sound and chest-thumping bass that Lynn's speakers produce. In particular, Lynn's Magic System allows you to have that studio-quality sound in your own living room. It's the most accessible distillation of the whole Lynn range, but one that produces the most gorgeous and clear sound imaginable.

0:40It will even make this podcast sound great, maybe. Head to lynn.co.uk for the best and most captivating audio systems on the planet. Hello and welcome to another episode of the Gentleman's Journal podcast. I'm Joe Bulmore. I'm the editor of Gentleman's Journal. And our guest on today's show is Harry Stebbings, the VC and podcaster. And we're here really because of The Social Network, the 2010 film by Aaron Sorkin and David Fincher, which was a kind of brooding portrayal of the early days of Facebook and the internecine wars, is that the right word, between Eduardo Saverin and a chap called Mark Zuckerberg, who's since gone on to do great things with the world, for the world, and had a jolly old time with all the money he's made, I think.

1:26A lot of people saw that film and thought, God, I'd like to be a tech founder, a tech guru. Seems to be a little bit of cash in that. I saw it and thought, I'd love to be a member of the Porcellian Club, the society at Harvard where the Winklevoss twins are members. And perhaps in many ways, I've been chasing my own personal Porcellian ever since. But Harry saw it at the age of 13 and thought, and I quote, gosh, I want to be a venture capitalist, which is remarkable when you think what the rest of us were doing at 13 years old. I was probably reading the Beano and even then just for the pictures.

2:00But I think that gives you an idea of the lovable precociousness of Harry Stebbings. He was 18 when he started his podcast, 20VC, which, as you'd hope, interviewed people from the world of venture capital in 20 minutes or less. And it was kind of an instant hit and has been running on for 1 ,400 and more episodes like a juggernaut ever since. And off the back of that, Harry has now got his own fund, 20 VC, which has invested in 13 unicorns, being, of course, billion dollar valued companies or more, which is a pretty good going. But we talked about that. We talked about the world of venture capital investment, the things that Harry is obviously incredibly well versed in about AI and tech and the future of both of those, which is always illuminating, but also about personal things as well.

2:51We spoke about Harry's very strict, I would think it's fair to say, regime, about his upbringing and his personal life and how his time at school probably formed him into the entrepreneur he is today. And I found it just fascinating throughout. And I could probably have spoken to Harry for four hours rather than just one. But I hope you enjoyed the episode. It was a lot of fun to put together.

3:25Harry Stebbings thanks for being here on the Gentleman's Journal podcast you're the only host your only guest in fact who's actually hosted us with their own equipment and this is far smarter and posher than anything we ever use dude you should come and actually A host it in our places and we have multiple studios next door now I know so you can actually choose the setting you can choose like fireside you can choose much more casual oh yeah Yeah, the ambiance in which you put someone for an interview is very, very important. It's not what you say. It's not what you do. It's how you make people feel, which is why being in an interview is very important to being a good investor, because you have five minutes at the start of a meeting with a founder to make them feel like you can tell them anything.

4:06And most investors are awkward and quite mathematical and engineering. They make you feel uncomfortable. My job is to make you feel super comfortable. And the way that you make people feel comfortable is really twofold. Number one, share a vulnerability with them. I suffered from bulimia when I was younger and had quite a lot of eating disorders. It was really tough. I might share something about that or my mother's MS. And it encourages them that they can open up in a similar way. Or number two is you ask for advice. Right. People, when they are asked for advice, feel superior and that you are in a subordinate position.

4:40And they open up more and they give very, very different to how most people would start an interview or a conversation. You've been doing this since you were 18. Yeah. That was your first episode. All those things you've just told me, you picked them up over time. You hadn't got that worked out at the age of 18, had you? No, no, no. And this is another massive mistake. Everyone should be building a personal brand and no one's building a personal brand. And every single person that I speak to pretty much says, I couldn't build a personal brand. It's just not me to put myself out there. It's just not me.

5:11It's what everyone says. and it's like going into a gym and going up to a treadmill for the first time and being like treadmill i've never met you before but me and you are great friends and of course you get on it's painful it's hard you don't feel comfortable you don't want to go back on it but next day you go you go you go and you get used to it in the 50th time you get better and better and better you asked me about public speaking before like i was very very insecure lacking in self-confidence but just through putting the reps in and doing it over and over and over I became a lot lot better what is it can you sum up your do you think you've got a strong and clear personal brand if we had to put brand stebbings on the wall I think it's incredibly important to have people who resonate with you and who dislike you dislike you absolutely you cannot have a successful I know it's true you cannot have a successful brand unless people dislike you Tom Hanks people dislike him yeah ant and deck people dislike them ask ant's wife ex-wife even um but absolutely and so when you look at the biggest brands in the world apple or windows yeah very clear distinction nike or adidas burger king or mcdonald's and the biggest problem with people is they're too afraid to actually have people dislike them and so they go in the middle and in the middle is where brands go to die.

6:34And so, no, I'm actually okay with that. Now that takes time because it's very hurtful to read bad comments about you. Yeah. But... Do you often get bad comments, even now? Are you serious? I get hundreds a day in my messages. DMs? Yeah. Instagram? I would say probably across all of them, probably three or four hundred a day. Three or four hundred negative messages? Yeah. Across... What does that do to a man's psyche? That's insane! Every morning you wake up and read that you know do you read them uh honestly no because there's too many no that would take you an hour two hours it would take far too long what's the general theme or perhaps we don't dwell too much the general theme is that you got lucky okay um and that uh you don't deserve what you have and it's the most important thing to understand with that is that very rarely does someone punch down yeah it's always someone who wishes they have what you have and the truth is you know i work seven days a week tirelessly and the work you do in private is the work you're rewarded for in public people see us talking now and think i go home at the end of the day and don't work people do not see you working late late late putting the hours in and that's what forms their opinion and so i it doesn't upset me i actually more realize that it's just their own unhappiness in their own life almost always in fact always what do you would you get nice messages too oh my god like more nice messages than bad messages great hey what are the nice ones so um you inspired me to tell my family about eating disorders i've struggled for years i tell my daughter about you and she told me all about her anorexia which i'd known about but she couldn't come out with and talk to me about your stories with your mother and her ms literally make my relationship with my mother better my mother is inspired she has MS too by seeing your mother walking it's a really dark world wow those are incredible things but they're not even the core at all of of what you're mostly talking about on 20VC or in your public persona oh no no no not at all but they're the things that clearly mean the most to you but the fact that you brought them up absolutely but this is also what people forget so much which is like you cannot build a brand with a corporate persona no authenticity is so important which is why leaders who are like oh i want to tweet but i don't want to do it myself it has to be you doing it you know toby looker a friend of mine who runs shopify he does all of his tweets it's incredibly authentic and it has to be authentic which is why my mother's ms and walking a marathon with her is very much on my social because it's who i am yeah of course and people resonate with people not with businesses and that's really important yeah can i take you right back then to the start of all of this and the first time i must have heard some of your first ever episodes and come across you very early on i'm so sorry for you well that was going to be one of my points because what i admire about it now is how how you just like you're relentless you'll get up and go and it was unpolished let's be very honest it wasn't in this kind of setup it was in my bedroom yeah yeah and that's with a 50 pound ice ball microphone okay called ice ball microphones because it was his little ice ball top.

9:46I didn't know any VC and I had no money. And I cold emailed VCs. And this is another thing that people suck at. The internet is the most glorious place in the world because pretty much anyone is reachable. You can email Jeff Bezos if you're smart enough to get his email. But they suck at the cold email. They suck at the cold email. If someone really wanted to get your time, they could say, do you know what? I love the Gentleman's Journal, the March edition. In the March edition, there was this. And it inspired me to do why. could I literally grab five minutes of your time I know you love lattes I'll bring it to the office and walk with you to your next meeting that's really a great cold email very short very clear request showed that you've done the work no one does that no the thing that that I think stuck out to me when I was listening today is I'm a little bit older than you you seem to have it kind of even worked out even then or was that just just the the naivety and brashness of youth in some way you seem confident oh yeah yeah yeah well I think my mother taught me that there's nothing that you can't achieve and only you know the limits of your own abilities and even then you are much better than you think I hate visions you know you're told to have a vision absolute bullshit there's nothing that's more constraining than a vision yeah right you will never be able to foresee what you're able to achieve when I started the podcast I wanted to be an associate at this venture fund in london well in three years time i raised 150 million dollars and was a founding gp of a fund if i constrained myself to the vision that i'd said i would be massively undershooting my potential and so to everyone you have to be micro ambitious right chase the shiny thing in front of you with everything you have but not pretend to be arrogant enough to pretend that you know what's going to happen in three to five years absolutely not I've got this Whenever you have a decision to make always choose the one which leads to more options Yes 100 % I'm building a kind of world view a grand unified theory I want to call it first stepism because if you want to do anything in life this isn't even new is it it's not even mine I'm realising Stephen Hawking Yeah Sorry Sorry to break it to you But I think yeah the first step is often God this is such a trite thing to say but it's very hard to make the first step and actually the first step is you don't need to know what the next 99 steps are just know that there's going to be other ones and that's fine just by the way 99 of people don't take the first step which is why such an important thing to do with the first step is to make it hard so much to walk it back yeah so like for me when i started you know the show i didn't have much money and i invested 80 of the money that i had in my bank account into a microphone and a domain name there was no what was that how much was that?

12:30Oh, fuck all, 200 quid. I mean, I was 17, 18. Maybe 300 quid. But there was no way I was going to spend 80 % of my money and then not do it. That was not possible. But if we go back even further, I've heard you say before that you were 13 when you saw The Social Network. Still one of my favourite films. Amazing film. I can't hear that soundtrack, those sort of eerie keys. Oh, brilliant. Without feeling something very profound and odd. Absolutely. gets to me. You saw that and you thought this is for me, this world. And other people might see that and think, what a difficult world full of disreputable characters.

13:08But you loved it. Well, actually most people saw it and thought, gosh, I want to be a founder. And I saw it and thought, gosh, I want to be a venture capitalist. I saw Peter Thiel invest in Facebook with his hedge fund Clarium Capital. He's a small cameo in that though. He's not even a big player. No, no, it's a very obscure scene that most people kind of ignore or disregard totally. But I saw that and I thought, gosh, This is the greatest job in the world. I can marry what I love, which is meeting the smartest people in the world with finance and investing, which is venture capital. You were 13.

13:37You were thinking like that. I do. When I was like seven, I used to get campaign the advertising magazine because I love advertising and telling stories. Wow. Building something that people resonate with is the most important thing in the world. You know, I always say to interview guests, the best shows are a combination of art and science. the art is telling a story bringing someone into that world with you and the science is sharing a framework of lessons that go alongside that as a result of that which is why we'll then manipulate questions because i'll say take me to the hardest or worst investment you made yeah and the lessons that you learned as a result i'm manufacturing the art and the science yeah yeah really important And that's the essence of great branding, great marketing.

14:25But when you look at what does it take to be a great entrepreneur today, I can tell you unwaveringly there's three things that are common in the$10 billion founders that I've interviewed. And I've interviewed pretty much everyone in the world, pretty much. Number one, they moved around a lot in childhood. You're forced to assimilate with different cultures, different communities, make new friends. Number two, they were part of gaming communities. They're very good at gaming. If you're good at gaming, there's a high correlation to you being a good entrepreneur. Okay, really important. And then number three is they started something entrepreneurial very young.

14:59All throughout my teenage years, I was doing arbitrage on Motorola Razr phones from Eastern Europe and selling them at boarding school. I was doing Kindle Direct Publishing on the student notes that I had. I still make three or four hundred pounds a month through Kindle Direct Publishing on GCSE English notes. Yeah. that's pretty good yeah i mean at the time i made like a thousand or two thousand pounds a month wow even better as a 15 year old well you've given me a bit of an open goal here then i'm going to put your framework back to you tell me what you were like as a 13 14 15 year old and how is the science that made you how that makes you good at what you do today because i can't my question i suppose is i can't imagine many other 14 year olds are talking about anderson Horowitz what were you what were your what did your friends think of all this stuff I didn't really have friends okay and it's a brilliant question because actually it deeply affected who I am today because I was very much alone and I used to go to the bathroom at break time because then other people wouldn't see that I had no friends Wow and I was very insecure and I doubted myself intensely and I was very insecure and unhappy in my own body as well I was very obese when i was young and i was quite an unhappy child to be honest and that actually is really important to who i am because so much of what i do is trying to prove to the world that i am actually worth something wow that's pretty motivating yeah as a founder story i'd buy that yeah and there is nothing that i will not do to win okay and and so if you're coming against me you should be very nervous.

16:39Yeah, why? Because I will be that motherfucker in the gym at 2 a.m. who is doing the extra rep just because I have to do it because I know that you're not. Why were you so unhappy, do you think? Just because, was it a vicious cycle? You didn't have friends and that made you unhappy or? I think, you know, there's this number one determinant of human happiness is the quality of your relationships. And I think I felt very much like an outsider. Everything that I loved, no one else liked. Was it because you were so interested in adult things, grown-up things? Yeah, I loved Andreessen Horace and interest rates.

17:14And fiscal and monetary policy was super interesting to me. But at 13, it's not very interesting to everyone else. And so there was just very little commonality. Any friend that I had was much, much older. And I used to get on much better with the teachers than I did the students. Really? Oh, yeah. Yeah. Absolutely. That's so intriguing. That's a great image. You'd hang out with teachers. Oh, yeah, at break time, I'd often stay in the classroom and talk to them for the break than I would go out with the students. And it's not like an arrogance of, it's just, I just have nothing in common with them.

17:48Yeah. And, you know, especially now it's fine. But when I was 18 to 25, I would be deeply, deeply nervous about going to a party with 21, 22 year olds. I didn't know what to say or do. Now, I would literally have dinner with the CEO of Visa or the biggest investor in the world. I'm walking completely not nervous. But gosh, going to a 21st birthday party, I would be so nervous. How old are you now, Harry? Remind me. I'm 29. 29. Do you still have social anxiety? The few times I've seen you out and about in the world, you've been high energy, gregarious. You would not think that there was anyone, there was any sort of social anxiety behind that.

18:31I have to say I don't have social anxiety anymore I actually think that people change as a result of success and money in positive ways as well I used to feel very uncomfortable in nice restaurants or nice hotels because I didn't belong I literally didn't belong, I couldn't afford it well now I can I have more confidence because I literally do belong and also maybe you've realized that it matters less whether or not you belong in a nice restaurant I mean that's not a good measure of humans yeah 100 % we were talking about carbone earlier I have zero desire to be seen at a cool place I don't really care what other people think about me right that's useful yeah very useful you see that in my fashion you don't like my top I don't care I'm not wearing it for you so that helps a lot it's very mentally freeing to remember that actually people care about you a lot less than you think yeah absolutely they're not thinking about you at all yeah do this i want to talk more about the the podcast in the early days but my question is do you have friends now do you have time to hang out with friends knowing everything i know about you and your schedule i mean my best friends are my business partners okay they work with me day in day out and yeah they're very great and dear friends and then i do have great friends that they're all investors or founders yeah so i don't have any friends you met them through work yeah i don't have any friends who are from school or from any other discipline of life but you've got the quality of relationships oh yeah that made you oh yeah i'm very happy now as a human i'm good i'm glad i know like life is life has really been good to me yeah yeah romantic relationships honestly no comment no i'm very happy to comment if you do what i do work wise and hour wise it's very hard to find someone who's willing to put up with that because you are by nature third for me i have my company i have my fitness and my health and then the relationship not many people are willing to be third no no couldn't couldn't they eat first in a different way no this is also what people forget which is that if you want to be the best you really have to be unwaveringly obsessed like there is nothing else that I think about that I do I don't do other things yeah I don't go out for dinners why would I waste three hours going out for dinner that just doesn't make sense no I want to get to the idea of the best I think that's such an interesting thing and it's very important in our culture but before I do let's talk about those early guests was there kind of one that felt like a big upward inflection a big viral moment a pivot a breakthrough whatever we want to say Absolutely, Ariel Zuckerberg, Mark Zuckerberg's younger sister And I remember it exactly, I was at university and it hit 100 ,000 plays for a single episode Wow Yep, and then I got a call from a sponsor And they said, we'll give you 75 ,000 Well, actually, it was$100 ,000 for three months on the show And I said, that's wonderful, I'd love to accept And then I went to my law professor and I said, how much money do you earn?

21:38And he said, I earn 72 ,000 pounds a year And I thought, wow, I've just made what you earn in three months from a podcast so I called up my parents and I said hey I'm gonna leave university for this weird thing called a podcast that you've kind of seen me do and they were like fantastic we're very proud of you well done right and I really give my parents credit for allowing me the freedom to pursue what I wanted to do yeah I've heard you say before that one of the sort of great tragedies is when you think everyone is kind of brilliant at something inherently and that the great tragedy is that a lot of people never allow themselves to find that.

22:14I've got two questions there. Do you think that's actually true, that everyone is brilliant at something, genuinely has something in the world somewhere that they would be brilliant at? Absolutely, I do. I think it's the saddest thing in the world, which is that 90 % of people really just don't find what they love. I don't attribute much of my journey to luck, to be honest. It's been fucking hard work endlessly. But finding this was luck. Watching the movie was luck. and so I'm very grateful for that but yeah I think absolutely everyone does and I think the biggest crime is actually made by parents today where they tell their children that they should do this and they should do that they should go and work at Siemens or Bosch or any big company actually you have to give your children the freedom to fail and I think this is the hardest thing about parenting which is like you have to find the tolerable quantity of suffering that your children should have.

23:10I was bullied. I was obese. I was unhappy. And it made me who I am today. Some bits were tolerable. Some were intolerable. But if you just cushion me and let me just have this perfectly free and happy life, the first time you get hit by something, which you will do, you'll get fired, you'll get dumped, you'll get something happening in life, you don't know what to do with yourself. And so it's like, how do I give my child a tolerable amount of suffering to make them durable as a human being? Yeah. Yeah, grit, I suppose some people call it. Yeah. You can get that in sports. I think sports is good.

23:42And I think we should definitely celebrate losing in sport and not give. One of my friends is worth about$25 billion. And he said, you know how I parent my children? Watch the Discovery Channel and look at the elephants. The elephants teach by leading. If you want your child to be nice to waiters, be nice to waiters. The biggest problem is the father who retires at 42 and the children see their father retired at 42 playing tennis. Yeah. Children copy. My part B to that question about finding the thing you love is how can people do that? You attribute some luck to it. You found something at a young age which is really fortunate.

24:21Many people really struggle. Lots of my friends now have been very successful in one field and in their mid-30s suddenly realizing, oh, I'm successful in something I don't actually like. I've got to the mid to top of something I don't care about. A hundred percent. I think one thing is you can fall out of love with something. That very often happens. And I think that's perfectly natural. You have second, third chapters of your career. If you're truly obsessed like I am, we are building a 50, 60, 70 year financial institution. This will be around well after I'm dead. So I think very long term, but I think the majority of people don't quite have that.

24:58So it's like be willing to embrace the second and third chapter. And then for those that don't know, I think actually you can do a Toyota's five whys. And Toyota have this very good framework, which is ask why five times. And you'll generally get to the core of the truth. And it's very, very helpful. This young girl came to me the other day and said, gosh, you know, I love what you've built, but I don't know what I like. And I said, well, what would you do on your day off? And she said, well, I would go to a fancy store and go shopping. And I'm like, that's super interesting. Why do you like being in fancy stores?

25:29Oh, it's because of the way they make me feel. Why do you like the way they make you feel? Oh, well like generally that's a really nice smell They they actually have everything laid out beautifully the people in there are super nice to you It's a really nice ambience to be around huh? That's really interesting. So it's like the way that it makes you feel in a luxury location Hmm super interesting and you were very detailed about the scents that they used in the different stores Have you ever thought about going into luxury hospitality working in some of the best hotels in the world? That's very important actually no, I haven't, but that's really interesting.

26:04Hmm, that's really interesting. Why didn't I introduce you to some people? Really? That is one of her biggest passions. And now she has a job in that. That's interesting because other people might have heard that and said, what do you like to do in your day off? I like to go shopping. They would have said, that's frivolous and silly. And they would have thought that's just you being a consumer or mindless or wasting your time. You thought there's some truth in that. Of course, there's always a more to it. Why does she like shopping? It's because it's the way that she felt. Okay. Why does she why does she feel that way because of the smell because of the shop assistance because the layout and when you were speaking to her you saw something in her.

26:40I saw her eyes. Yeah. Yeah. When I asked the why do you love the shopping and she said it's the way it makes me feel and most people then stop again. And just when you think you should stop you should ask why again. Okay. That's good. It's like with interviewers. You know the biggest problem with interviewers is they're not comfortable in silence. very often after silence comes the most valuable part be comfortable in silence i want to play five wives with you but i suspect you know do you feel like you're very in touch with your own motivations if i asked you five wives you go for it okay you say you want this company to last 70 80 years after you're dead why is that i'm scared of being forgotten in timelessness of kind of eternity why do you think that is i think like when you realize that we all just go to dust i really need to feel like something is left behind that is me i don't think there really is a why to the pivot off that because i think that's pretty fundamental you've sort of shortcutted the process you're like why do you need to feel like that yeah I suppose so yeah probably because I if you're not going to be here the obvious question is why do you care you're not going to exist you didn't care about it in the year 1976 or 1742 because you weren't here you're not going to care about it in the year 2097 because you won't be here it's probably because I have a very large ego do you and I like to think that there's something that will outlast me and still be part of me I agree but I think children help with that but the challenging thing about children is do you know your great-grandfather's name?

28:22I know it because it was the same as my grandfather's name, but even now as you say that, I'm actually thinking maybe it was the other way around and his middle name was swapped. Proving your point, the fact that I haven't got confidence to tell you. I give you 95 % of people don't even know who their great-grandfather is. Oh, God. And so the idea that you live through your children is nice, but it's relatively time-bound. I saw an interview with Paul McCartney, and you're very much the Paul McCartney of VC, I think. He said that in, like, even a hundred years time, people will probably remember, like, two or three songs of his and he's probably the most important songwriter of the 20th century which is crazy to think about and very profound and it made me think about what our songs should be in life so to speak if you're really going to want to be remembered and you care about posterity and with respect no one's going to care about this podcast episode for example probably no one's going to care about 90 of the things i've done this week what are the things i'm going to do this year that are going to result in me having a couple of songs do you think like that Yeah, absolutely.

29:19And it's why we did Project Europe in some respects. Project Europe, for those that don't know, is a program which basically gives$200 ,000 to 18 to 25 year olds in Europe to build the most ambitious companies in the world. Robotics companies, medical companies, cancer treatments, space companies, defense companies. yeah in 10 years that we will have 10 10 000 person companies that would never have existed without project europe that is like oh shit we're changing the gdp of a continent that's i mean that's lasting that's very lasting and do you mind if people don't know that harry stebbings did that i don't care you don't care so your ego extends up to the point that it exists but actually you don't need the your name in lies honestly i don't need my name in lies i need to feel like i did something impactful, that my time was worth it.

30:35sound and chest-thumping bass that Lin's speakers produce. In particular, Lin's Magic System allows you to have that studio-quality sound in your own living room. It's the most accessible distillation of the whole Lin range, but one that produces the most gorgeous and clear sound imaginable. It will even make this podcast sound great, perhaps. Head to lin.co.uk for the best and most captivating audio systems on the planet. I'm interested in how you pivoted that podcast to a proper job in VC. That was obviously your early goal. Was that Apollo? Was your first fund you worked for? No, it was Atomico.

31:12Atomico. That's what I mean. Yeah, it was a billion dollar fund from the founder of Skype. London based? Yeah, London based. And how old were you when you got a job there? 19. How did you do that? I think they paid me$200 ,000 a year for like three days a week. Wow. And 19. Yeah. And I was an entrepreneur in residence. I can't wait to have children one day and say my first job was an entrepreneur in residence. So you've never had a proper job before that? No. Not worked at a pub or? Nothing. Wow. That was your first job? Because I made money through entrepreneurial things. Like working in a pub would have been vastly inefficient.

31:49But it might have taught you something. Some decent lessons working in pubs. Actually, yes. One of the most helpful jobs that you can do is working in McDonald's. yeah time pressures unhappy customers the importance of process-driven work so absolutely and i don't belittle it at all i would actually try and get my children to do the same but that was my first job um what do you do as an entrepreneur in residence my job was honestly to try and find good companies that we could invest in and i absolutely hated it really i absolutely hated it despite a lot of money for a young person really hated it was incredibly formal and it didn't embrace creativity and freedom in the way that i wanted it to it was very much like a bank and that's not how i thought venture should or could be so how long did you last there four months four months four months it was more of an internship right look at it like that were they surprised when you left i don't think so i think i was a terrible employee too which is very interesting because like people often do a lot of references before they hire someone yeah never ever listen to references if you're investing in someone's new company because generally founders will be terrible employees.

32:53I'm a terrible employee. I don't really take orders very well. I'm very unstructured, creatively, absurdly weird. I mean, I'm dressed relatively smartly today. I'm normally in very different attire. I eat one meal a day. I go to bed at 2.30 a.m. What time do you wake up? 8.15. Okay. Pretty rigorous, pretty rigid schedule. Yeah, yeah. First walk in the park is at 8.30 every morning. always have a first meeting at 8 30 and so like very very so to the point often references will mislead you and i think i was a very bad employee and i didn't like it and so i i left and i started my own fund then so that was straight out that you still 19 maybe 20 still 19 still 19 and that's when you set up 20 vc as a fund yeah as a fund so how did you convince people to give you money ah well i i had already interviewed you know 300 people yeah and a lot of great people sent me deals they sure thought i should invest in and so i went to some of the biggest founders in the world including the founders of you know spotify and many others and they gave me money to invest in these companies wow and i started with an eight million dollar fund and i was investing out of my bedroom just you just me how many employees do you have now 20 bc across everything like 25 25.

34:13As a terrible employee, what are you like as a boss? I would say very, very demanding. It's not easy working here. And it's not meant to be easy working here. This is the place where you will do the most meaningful work of your career. And you will make more money here than ever before. And you will make more money here than you ever will anywhere else. It's a good pitch. It's a very good pitch. But if you want to take the baton, be ready to work fucking hard. Right. What does that look like in practice? honestly we don't sleep so like i don't agree with like the change your desk at all but we absolutely do do 9 a.m to 9 p.m six days a week okay we absolutely do what if someone leaves at 8 55 that's fine okay so it's not so it's not a rigid light of course it's a it's a yardstick of but it's but you know what that's that's on me to make everyone feel like an owner of the business then because if they're an owner of the business they won't want to yeah i will jump on calls with people at midnight 1am and they're like yeah yeah and they want to do the call not me okay because they feel like an owner of the business and this is why so many leaders go wrong which is they don't inspire their team to see why the work that they do matters yeah you know our media team why are they so passionate because we have 14 year olds from favelas in brazil who watch some of our tiktoks and feel inspired to start a company or feel that they can do more with their life.

35:37The work that you do upstairs here inspires millions of children in some of the most poverty-ridden countries in the world to feel that they can do better, that they can do more, and their life isn't as difficult and hard as it actually is. That's why you should be so inspired to stay and work harder and harder and harder. Have you ever had conflicts with that worldview with your employees? No, because I'm very clear up front, and I think this is another massive problem that people make in hiring, which is they're not very, very clear about what it takes to succeed and what they're even looking for.

36:15As I said, we work unreasonably hard, and you will do better than you've ever done before. The quality of your work will be better, and you'll make more money. Nick from Revolut taught me something very clear about culture. nick taught me that we conflate culture and happiness and it's bullshit actually people thrive when they are developing personally and when they're developing financially so the only thing that you need to do is focus on winning right when you win people are happy yeah very rare to have a company where they just continuously lose deals no one ever succeeds there but they're very happy yeah no no when you are winning when you're making money when you're learning when you're growing when you're doing better work more work people are happy i mean it's pretty irrefutable that success is an incredible motivator and it's a and it's a virtuous cycle in some ways absolutely but also just remember the the importance of humility that like i'm always learning you know for me as a leader i never ever want anyone to feel like they can't tell me that i could have done something better or differently and so it's your job as a leader to create an environment where people can tell you you know what dude the way that you approach that conversation could have been handled better that's really interesting how could i have done that better i always want to know and the minute that you don't want to know how you could do it better or don't think you could have done it better is your last day.

37:46What has people told you recently that there are a bit of a learning for you about something in your working life? Sometimes feedback doesn't need to be given directly. And when I say directly, I mean directly in terms of time. So you got feedback about some feedback? I got feedback, yeah, absolutely, which is very, very helpful. And so the way that that shaped itself is like, you know, I move fast and I very much like velocity. but actually sometimes you need to appreciate that it's not the right time yeah and that actually tomorrow is a little bit better than today i know it just happened but actually that's the worst time actually to hear not the right time you're not in a good headspace just make sure and they're not in a good headspace and so you know what sometimes it is okay to go to sleep angry so to speak and actually the time with which you deliver it is really really important the other thing is you A great leader is a little bit like a conductor in an orchestra.

38:44You need to actually play people individually. The flautist requires something very different to the saxophonist. And your job as a leader is to understand the intricate parts of your team and what makes them play great music together. And it's not the same. And that's why kind of homogenous cultures are such bullshit. Because some people thrive on carrots. Some people thrive on sticks. and you can't plaster on this homogenous culture to everyone because it's so different for each person. Yeah, definitely. I'm learning I'm a big carrot guy. I only passed my driving test last year at the age of 34.

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39:19You haven't said congratulations yet. Congratulations. I'm thinking, oh, shit, I haven't passed it either. Have you not? Okay, well, maybe Leon, my guy, he was the most positive driving instructor ever. And I'd had a few before, and every time something went wrong, they'd be like, why are you doing that? And I'd be like, because I don't know how to try. Hence me being here. What do you think this engagement is that I'm paying you two hours on a Tuesday afternoon for? I don't want to be doing this. Leon, anything that goes wrong, he goes, it's so good that's just happened. Because now, you know, anything I said, even the smallest thing, point like, oh, that light is red.

39:58He'd go, that's it. That's it. like I'd put my finger on something so true about humanity. It's so good that you hit that tree because now you'll know not to hit more of these trees. Amazing that you've killed that pensioner because actually she was a real bitch. Thankfully, I've never killed any pensioners or hit trees. But that's because Leon was so... Because Leon was that. Yeah, his management style, management style, his coaching style, whatever we want to call it, was carrot, carrot, carrot. And that worked for me. What would work for you? Do you want Leon or do you want the first guy, Jose, who was berating me constantly?

40:36No, I need to feel behind. It's a very important question I ask. You feel behind? What does that mean? Yeah, like it's a very important question that I often ask people when I'm trying to understand them is you're running in a race. Do you want to be the pacemaker and lead from the front? or do you want to be behind and see your enemy and see them literally ahead of you but be on their shoulder be ready to take over them be ready to lap them i want to be second watching watching watching i don't like being front not knowing where my opponents are not knowing how much headroom i have for me it's really really important to be just behind so i can constantly see what I'm chasing.

41:17Okay. And so in this case, I think I would rather have the stick. But a stick. Because I thrive on actually the challenge that is ahead of me being like a threat almost. Or perhaps it's that you'd like a driving instructor who pushed you out of your comfort zone fairly early on and said, right, we're going straight on these motorways. You'll work it out. That's you being behind this. That sort of tiptoes on the bottom of the pool when you're just about to drown as a kid and then you work out how to swim. I mean, I legitimately don't think driving licenses will be needed in 10 years. Okay. You really think so?

41:49Oh, 100%. You're not tempted to do it? It's quite useful driving, I've learned. I'm not tempted to do it at all. Okay. You're not a car guy? No. But this is something that's almost freeing, which is like the single best way to increase your happiness is to reduce your wants. Yeah. One thing that I find very mentally freeing is I don't want for anything. Really? I don't have any watches. I don't have any cars. But I don't like clothes. I don't like traveling What are your luxuries in life then? What do you spend your money on? I mean honestly I spend my money on great sashimi and that's legitimate.

42:23Property? You've got a nice house? I've got a nice apartment but like honestly but I don't buy it. One of the biggest lies that we tell children is that they should buy property. It's one of the worst investments you've ever made It's truly the worst investment that you'll make. Also it ties people as we were saying before into careers and jobs that they feel they can't leave and they go well now i've got a mortgage i'll do it five more years and people always forget the opportunity cost of their cash and for those that don't know what an opportunity cost is it's the choice that you didn't take by taking this choice that you did yeah by putting a million pounds in a property you're choosing to deliberately not put that million pounds somewhere else and that is very very expensive decision and so no i don't i mean i have a very nice flat which is great do you have a nice bed i mean do you do i can imagine that you've invested in the essentials very well i have an amazing bed right i have an amazing desk yeah my office is beautiful you've got a very good chair for your back i have a very good chair for my back but honestly i don't want for anything which is so freeing and i actually get great pleasure i buy a lot of shit for my mother especially chanel and that i get great joy from that and not like oh i'm so charitable and christian but like it makes me very happy to see her happy in that way because you don't have the equivalent for you.

43:38You're not excited by... Zero. You don't want to deck yourself in Laura Piana? Zero. Okay. But that goes back to eating disorders. I feel very uncomfortable trying on clothes, looking at myself in the mirror. There's still a great amount. Still now? Yeah. Because we just did a photo shoot. No one else will know that, but we just did that. And you seem very comfortable in a very visual moment and medium. Not at all. I think one of the hardest things about eating disorders, when you you look at addictions and mental kind of psychological challenges is it never really leaves you because you always have to engage with food and your relationship with food is never done you know i don't drink i don't drink for you know obvious reasons um i couldn't stop and it actually is much easier to stop drinking you just stop drinking but you can't just stop eating your relationship continues so it's probably one of the hardest and male eating disorders is probably the saddest thing that we have right now and a big big problem that we have to deal with Is that something you're interested in?

44:37Doing a lot more about, yeah. There's a huge amount of young men who feel that they can't say that they feel desperately unhappy in their own body. And you see the meal preppers and the gym addicts where it's unwaveringly obsessive and unhealthy. And the amount there is terrifying, to be honest. Yeah. I guess we are in a real entrepreneurial moment in some ways, at least as far as the culture and media goes. People are obsessed with entrepreneurship in a way that they weren't 50 years ago. what's going on do you think everyone should aspire to be an entrepreneur is that just the economy we live in now entrepreneurship is sexy because it is viewed in contrast to corporate life which has never been more boring and doldrum and uniform and i think entrepreneurship is the expression of individuality and creativity and freedom that is the pros now should everyone do it unwaveringly not it is the single most painful thing that you will do it's like eating glass cross-continuously.

45:34I went fundraising once and it was very, very difficult. And I spoke to my friend who's the founder of Calm, the meditation app, and he said, Harry, you don't get it. You have to enjoy being punched in the face. And it's psychologically unhinged to actually go, I love getting fucking punched in the face and I want more. And the punches in the face here are rejection. You can't do it. We won't give you money. I don't want your product. You'll never build down and think big i don't even like the category a magazine in 2025 you idiot no we won't give you money no we don't have budget no it won't work over and over and over again and so it is not for everyone and also the work that is required to make it successful is unwavering yeah and it's also completely psychologically a bad decision to choose to be an entrepreneur you will work for many years with very little pay with absolutely no proof of success that is a very bad equation to do or to align with it's almost like marriage um except that's just continuous uh at least your company can fail and die you know marriages seem to go on um but it's really really not for everyone sexier than ever agree not for everyone definitely what type of entrepreneurs do you like and what Who do you like to invest in?

46:57It's very, very simple. I look for three things in an entrepreneur. Overarching, you need to be psychologically unhinged. Completely unhinged. What are the markers for that when you're meeting someone? There's three very clear markers. Marker number one is a sense of supreme superiority of self. So it's like I fundamentally believe that I'm the best person in the world for this. I am the most gifted and talented person for this job. Wow. Like I believe I am the best. number two is this paradoxical duality which is incredible insecurity i'm not doing enough i'm not working hard enough we're not moving fast enough we could be doing more why aren't we here why aren't we doing this we're going to get beaten by this this paranoia yes absolutely filled and so it's a weird duality to have and then you layer on top impulse control and impulse control is the ability to not do things that everyone else cannot not do which is the drinking at the pub at the end of the day the having the pizza at the sofa instead of going to the gym so doing the sales call at midnight because they're in pst which is obviously us west coast time and they want to be in bed with their girlfriend it's like you know what's really hard for me i tell all any girl that i date i'm unwaveringly addicted to my job we will not go away on weekends all girls like oh i love your ambition that's so nice a month in i want to go away on the weekend everyone wants to go away on the weekend it's the ability to buy no like we will not do this we are incredibly disciplined right and that's self-control and the impulse control is the third which makes really great entrepreneurs are those three things true of almost all the unicorn founders or billionaires you know a hundred percent and this is where people really get upset with me when they hear I will be probably your most unpopular guest ever on this show.

48:46I don't think so, by the way. I think you're being tainted by those DMs. But that would be like 996, the aggressive approach to work, that unhinged psychological element that he just mentioned with those three elements. This only applies to people who want to build a$10 billion business. It doesn't apply to... If you want to build a really nice clothing company, you can totally do it on five days a week. You can totally do it without being unhinged. No offense if you want to build most businesses. But my job is venture capital. My job is finding the one or two businesses that will change society.

49:25What have been your greatest successes with that method? What have been your biggest investments that have come off? Luckily, we've invested in$13 billion companies. Well-known ones. The most well-known today would probably be Lovable, which is the AI company that allows you to create a website from anywhere. which I love. There's another one which is smaller but I think is important and I'll say why. It's called Fixer. Email autocomplete. So basically if you have lots of emails it takes doing emails from 30 minutes a day to 3 minutes a day. What stage did you invest in Fixer? Oh like seed round.

50:03Here's something that's going to blow your mind then. I came up with the name Fixer. No. Dickie Hollingsworth and Archie Hollingsworth. I was the first person they employed i was a freelance writer at that point bumming around at the age of 25 they were like oh why don't you come up with our name i did their first ever logo which they used until about three years ago i think they paid me 150 pounds you do know how much they value that now don't you well i see it i see it frequently because they're very good at promoting themselves on linkedin and i and i'm very fond of them the company's worth 300 million how much do you think my name has added value it's not the name but why do i like the two there and i use those two is because the best companies make customers feel like superheroes yeah and whether you are creating a website that you could never do before or answering your email in a tenth of the time you feel like a superhero why is nike such a fantastic brand because it creates everyone or turns everyone into an athlete.

51:04That is a very powerful brand. Make your customers superheroes. Going back to my question, how much money should I be asking the Hollingsworth brothers for? I would definitely be asking for six to nine million. Six to nine million. Yeah, I think two to three percent would be a fair take. Absolutely agreed. And that's from a significant investor. So actually, we could just cut out the middleman and you could pay me six and this will all go away. How important are names to startups? That's a nice pivot. How important are names to startups? I think it's important that you are viewed positively. Yeah.

51:39There are names, and Peter Thiel says this very well, but there are names which are inherently positive or uplifting. Airbnb is one very good example. What's uplifting about that? Air is buoyant. Yeah, it feels light. Yeah. But B &B, I always thought, was the odd bit there. Do they have B &Bs around the world? Is that an international concept? Yes. Must do. Must do. really interesting thing also that um most often great great founders are incredibly articulate on historical stories or data and so if you speak to brian chesky the founder of airbnb about airbnb he'll talk to you about communal living and how in the 1500 1600 1700s it was entirely normal to share your house with strangers and that was actually where the idea originated from and i I love that you see in the very best this kind of homage to history in a lot of respects.

52:30What was it? Did it have another name before? Air Bed and Breakfast. Right. And they just cut that out. Because there was a similar service that was called like Sofa Surfing or something. Yeah. Which is a very different proposition just from the name. You feel like a bum. You feel like a student sleeping on your mate's sofas. But I think it was the exact same principle, spare rooms and spare spaces. 100%. That's the most funny thing, which is like never, ever invest in someone's idea. Invest in the person. Everyone at Seed thinks it's like, oh, is it the idea? I don't care what you're working on.

53:05I care that the entrepreneur in front of me is able to transform an industry. Products change. Markets change. The people will stay the same. So I don't care what you're doing. What I care is do you have the traits that it takes to be one of those generational defining founders? I really don't care. So FIC service example, and this is just because I know them, that was a virtual assistant service, which was like an inexpensive way to do things. They had assistants around the world. They pivoted very cleverly. A hundred percent. No, actually, they didn't pivot. They used the historical data that they got from that business to help inform AI much more significantly, which actually was an incredible moat.

53:43If you think about why couldn't anyone then just create a much better EA? was because they didn't have five to seven years of historical data on what makes a great EA, which they had meticulously captured, cataloged, tagged to make AI much more efficient for them. And so I think it's a great example of a really defensible and durable moat in AI. Yeah, and a brilliant name. And a brilliant name. Really brilliant name. What do you not like about this industry then? What do you think? There's too many tourists. There's too many fucking tourists. like yeah there are way too many tourists tourists to the industry yeah like people who just want to make a quick buck right people who think it's cool and they get to hang out at annabelle's and five hartford street and it's like the cool thing to do like this is not the cool thing to do this is a hard job about supporting incredibly talented founders to achieve their dreams and being there every single fucking day yeah all day to make sure that you provide an amazing quality service to your customers and i think far too many people think that this is about intellectually wanking and pontificating about the future before going to five hartford street or annabelle's to chat about their stupid holidays to some vacuous place in mykonos or san trapez with their other moronic mates yeah who are decked out in her maze and laura piana forgetting actually that the great fucking founders that we back are literally what pay our wages yeah and they're not they're not sitting in hartford street and not fucking sitting in harper street we're going there after this actually no um there's an image in popular culture to take your lead from that of the kind of vc bro you're wearing quarter zips or gilets taking a call from their borrowed yachts i think of things like silicon valley did you watch that show of course uh and captures it very well and the more extreme end of things perhaps on the founder end is did you watch mountain head recently jesse armstrong's thing no i haven't seen he did succession which you may have seen but it's a film essentially about founders stuck on it in an amazing shadow in a mountain as the rest of the world falls apart and how they react to it um very very interesting case study almost like a chamber play but there is a level of and the way they're talking and presenting to their alleged friends one-upmanship macho-ness it seems like a very there's a there's a there's a certain texture sometimes to the way people talk in in entrepreneurship and vc that from the outside looks like they're wankers tossers to use your favorite insult i agree yeah what's going on there i mean you know my grandfather's 82 and he earns 13 pounds an hour shoveling gravel on a golf course never forget that we are in an incredibly privileged and luxury position people always say to me oh do you not have balance now you work too hard I work in a really nice office with amazing people getting brought espressos and lattes and whatever I want I'm incredibly fortunate to see what I do I think we are so spoiled as a generation yeah and I think actually you know a hundred years ago we were in trenches sending letters back to our parents because we probably were going to die the next day and now we're trading crypto in our underpants while getting delivery brought to us talking about kombucha and fucking breath work it's a disgrace how most of society has fallen and i think we need to hold ourselves to much higher account and yes the bro culture i actually just think it's about being a good human right going back to your point on the quarter zips and the calls from yachts yeah don't forget where you came from and don't forget who your customer is because all of this can go away overnight nothing is ever infinite that's why i hate this business i don't know a lot of things and you know what i'm very happy to say i don't know or i'm scared yeah that's okay and i think this fake bro macho-ness is just i agree what are the phrases and things that you you hear a lot that you hate what do people say that really annoys you specifically in founder meetings there's things which you should never say, which everyone says.

57:55Oh, this is the last round of funding we ever need before we're going to be profitable. If I had that, I mean, Elon Musk rich. The market's$50 billion. And so if we just get 1%, we'll be 500 million in revenue. That's not how it works, sadly. Terrible elements like that, for sure, which just really frustrating. Can I pick your brains? Oh, no, no, no, no. What's wrong with that? That's someone asking for advice, isn't it? Do not say, can I pick your brains? What would you rather they said? At least can I steal your ideas? I would love to understand how you leveraged media to get your first job with Atomico.

58:33Would you have five minutes for a coffee? I know you like double espresso from Daisy Green. Can I get it with you after one of your meetings? If someone emailed you that tomorrow, not cynically because they heard this. 100 % I would absolutely do it. You speak to young people a lot? The whole fucking time. What piece of advice do you give them the most? Most important thing is just start. Second most important thing, this is a game of who can survive the longest. Most people fail because they quit. Most people fail because they don't start. And then the second reason most people fail is because they quit.

59:06The truth is most people won't care about what you do for long periods of time and you have to get comfortable doing it even though no one is watching you. Quitting is sometimes useful, no? Quitting is sometimes useful. And that's a really important recognition to understand. And I think the question to understand of should I quit or not, it's a really helpful one I find, is would I be okay if I saw someone succeed in what I'm doing? Let's take you and Gentleman's Journal. Would you be okay if you saw someone be running Gentleman's Journal with great success and then selling it for a large amount of money?

59:42That would pain me. That would pain you. If you're like, you know what, I'd be fine with that. then quit yeah the other one is do you have more ideas that you would like to try within this environment or company and if you're like no i'm out i'm out yeah but if you're like yeah we haven't done shorts in a way that we could do we haven't done food in a way that we could do we haven't done travel there's more to the tank in terms of gas in tank that face you just did when someone says i'm out that to me screams of kind of burnout and i've seen it in in people i know are you ever concerned that that's coming down the line for you working as hard as you work don't we need rest and holidays and weekends away no simple okay no do I worry about burnout this is also where people kind of fail to understand I spend 75 minutes in the gym every single day okay I definitely have 6 hours 15 minutes in bed every day I do not have less than that you sleep well yeah I sleep really well I'm very tired.

1:00:45Do you have a sleep routine? I go to bed at 2 15 and I get up at 8 20 Take some supplements? You take magnesium Absolutely, I take quite a lot actually I wake up every single morning and I go straight to the fridge where I've already made the night before Brian Johnson's longevity shake. Okay. It's like 60 vitamins in one and then I'll have a double espresso right after that right before the park and then when I get into the office after the walk I'll have electrolytes in water and then I kind of have that continuously throughout the day. It's really important to stay hydrated and then in the day before and after gym I'll have creatine and then before bed I'll have magnesium.

1:01:20Isn't another kind of rest important aside from sleep as in getting away from things and going to see a different culture or just breaking up your routine in some way? For some people, yeah. For some people, yeah. For me, no. No. No. Also, my job is largely a job of output. I have a lot of shit to do. If you are creatively driven in a different way where it's about one great piece of work that will define you and it's about bringing in lots of inspiration, then no. Yeah. The key is not to sit at your... If you wanted to write one amazing piece of work, sitting at your desk for nine hours a day...

1:01:58But mine is a game of output. It really is a game of how much can you do. On the other hand, you don't put bad things in your body. No. You don't drink. No. You don't take drugs. No. You don't smoke, I presume. I do smoke. You smoke cigarettes. that's interesting yeah I only smoke at 1.30 in the morning and this really surprises me you said it earlier but I kind of must have just I don't smoke at all in the day I think it's incredibly unattractive unprofessional to smell or smoke I'm not addicted to cigarettes in any way just very much like a biscuit I enjoy a cigarette how many ciggies do you smoke?

1:02:374 to 5 a day 4 to 5 a day that's a fair amount of ciggies yeah but you don't drink that I don't drink I don't eat any bad food when did you stop drinking a thousand and fifty three days ago well you you know yeah did you stop for the health benefits or because you had a an issue with it do you think or both I stopped because the founder that I invested in said you know it's such a shame Harry you could be one of the best investors ever and I guess you'll just be average and I said that to you I said what and he said yeah if you think you probably lose 20 of your productivity and efficiency every year because of drinking but he knew you were hungover or drunk at that point or what yeah he knew that like i was drinking a lot wow they used to call him when i was drinking so this was a real kick up the yeah and and i said okay fine 20 a year and he's like yeah and you're 25 so let's do 20 by 25 years when you're 50 gosh 20 every year compounded for 25 years actually dude you may not even be good you It may just be average.

1:03:40So what could be the world's best is average. And I just thought, you know what? That was enough for you. I was like, hell, the most terrifying thing is regret. And I could not live with myself. Really, the worst thing ever would be a life where I thought I could have been more. Wow. So you quit overnight, no problems quitting? Zero problems quitting. What do you... I'm one of the most mentally strong people in terms of my ability to control what I do. You've got discipline. Yeah. that was forged do you think in the the adversity of your childhood somehow no it was forged in the weight loss i was 130 kilos and i went down to 75 kilos in six months so i lost 55 kilos in six months right and it taught me that there was nothing that i could not do physically and then i also have run several ultra marathons and very long distances where you your mind is the most important and only thing that keeps you going you know your body gives up well before your mind the question is can you keep your mind going right do you ever want to drink again or is it all fine now never with the first like people say the first what month is difficult 90 days maybe i honestly i don't find that i don't miss that i don't mind i used to drink a lot of diet coke 14 15 a day wow yeah people are listening to this game this guy is weird or fascinating or i hate him but yeah so I used to drink kind of 14, 15 a day stopping that was one of the hardest things to stop, I was physically sick, seriously you had a sort of a physical dependency on Diet Coke, physically sick terrible migraines, extreme exhaustion body physically desperately, desperately craving it, what was the curve to come out of the DC hole I mean it took probably four to five days of feeling like real death What is it in Diet Coke?

1:05:32Caffeine. Caffeine. It's the caffeine. But you have coffees now, it's fine. I have coffees now, but nowhere near the caffeine consumption. And that, I guess, Diet Coke isn't like having espressos. It's kind of a low level of caffeine. Yeah, I would never let my children drink any Diet Cokes or diet drinks. I would also never, ever let my children in a social media, ever. It's the most poisonous thing we have. That's the most weird duality for me because I'm always on social media and I have to be. You told me before that in that hour before you go to sleep, you spend time analyzing thousands of reels and YouTube shorts and things like that.

1:06:08It's because this is a complete science. We need to hack your brain to captivate your attention. You wouldn't let your own children do it? No. Are you happy being part of an industry that you wouldn't let your children be a part of? Yeah, I am. Yeah. Fair enough. I care about providing for my family. Okay. What's so bad about social media then? how it makes you feel and how it wires your brain. What do you know from the inside that maybe people like the rest of us don't understand about how it does that? Oh, we fundamentally are trained to make you addicted. I'm invested in a gaming company that will remain nameless.

1:06:43And it is 70 NASA scientists who fundamentally should be building rockets to further humanity. But they instead are wiring game mechanics so we can make your children addicted to play games. and then pay so they feel like they're going up levels when they're not really to buy more skins and all of it is for increasing shareholder value. How does that feel? We're increasing a lot of shareholder value. And then on the other hand, you're doing things like you told me before. But by the way, there is many, many different types of cancer in that world. And I use cancer very deliberately because the social media companies are exactly that.

1:07:23they are trained to keep you there that's all they care about because that's what they get paid on and so they are manipulating your brain in every way possible i don't think people should be worried about like privacy and data sharing trust me facebook seeing that you like protein recipes or bicep exercises is not the worry it's how it changes the chemistry of your brain yeah i think we all notice that don't we yeah being super direct porn is one of the most dangerous things for young men. There you go. There you go. Don't look at me. Don't watch porn. But also don't go on social media. Do you, if you could click your fingers and all the service.

1:07:59I would be off social media in seconds. Do you have a dependency on that like you did with Diet Coke? It's not like I have a dependency on it. I don't, I don't care about, I have to do it to be the best in the world at what we do. And it's such an important mechanic. It must be working on your brain in the same way though. A hundred percent. I'm not like immune to it or like, you know, intellectually superior. Even though you know about it. No, no. And you recognize it even. You're like, oh, how interesting. I've passed through the first level. They've done that, so it's an easy level. So it makes me feel like I'm feeling a sense of achievement early.

1:08:28Yeah, yeah. Oh, absolutely. Do you think we'll look back on it like we look back on cigarettes and medicinal cocaine? Very potentially, but we will definitely be the most unhappy generation of humanity. Jeepers. Yeah. And at the same time, with what you said earlier, also one of the laziest. Oh, absolutely. The softest, definitely. I mean, if you think about like human data around actually physical excellence, whether it's whoops or auras or Fitbits or anything in between, it's strange that we have one of the most challenging obesity epidemics in the world or pandemics. And we also have more data on human excellence and physical productivity than ever before.

1:09:07I'm very worried about the diet of humanity as well. Mental and physical. Mental diet, absolutely, in terms of the content that we consume. The physical diet as well is just absolutely poisonous. Everything that you buy and eat is largely manufactured for economic reasons and very, very dangerous. I can see you in 15 years time buying your ranch in New Zealand and fertilizing your own crop, so to speak. This is why I'm single. There's not much of me that's easy and I appreciate that. I think you're hard on yourself, you know. I think you have a very singular charm. Charms sometimes rub people up the wrong way.

1:09:46but I think your candidness is remarkable and very admirable it's interesting it's never boring so I don't think you should worry about that I think it can be exhausting maybe if we record it for another hour I might agree but I think it's very stupid but at 1.30am when we talk about the tulip tulip mania I don't know if you know it I know it as an example of madness massively inflated markets and kind of economic irrationality. Yeah. Yeah, like I will genuinely be interested to talk about that at 1.45 in the morning. Okay, well, I'll see you there. On that then, before we go, what trends now do you think are being completely overinflated?

1:10:29What things now are part of a tulip mania? The majority of AI. Like the majority of AI, where you see AI on your toothpaste or toothbrush, I saw like... What's that? AI toothbrush. It's where it knows you so it turns off when you should and shouldn't and it analyzes the bacteria exactly and it's just like i i probably yeah but that would need entirely new hardware yeah it would need incredible chip performance it would need incredible battery performance i promise you that shitty oral b brush that you have is not it so people are slapping a eye on everything a protein on everything too the misuse of protein and nutrition is just a disgrace protein is not all the same when you shove synthetic protein into a protein bar it is not the same as having eggs.

1:11:15Absolutely not. And so unwavering trend there in terms of protein mislabeling to AI just to the moon bullshit. I think there's a trend around negativity in London, which is really dangerous. Tell me more. So people are down on London. Oh, it's like cool to be down on London. Yeah, I find myself doing that. Everyone's leaving. Everyone's leaving. Yeah, fuck off. let's make London yeah let's make London great again why don't we appreciate that Rich and Archie have built Fixer from London to 30 million in revenue and is now hiring 70 people London's pretty good when you leave London and come back you realise a lot of green spaces a lot of trees fantastic parks this is a great place to be pubs maybe not for you but a pub is a beautiful thing pubs a great thing the culture is fantastic and so i think the trend of like hating on london trend of hating on europe that's just british it's just absolute bullshit we need to have a trend more of like yes culture the biggest problem with europe and the uk specifically it's like it's cool to be negative and one of the best things in the us is they believe in you when you don't believe in yourself and i want more people in the uk to say yes to amazing young talent before the young talent sees their own potential our job is to enable a generation of incredible entrepreneurs to build things that matter that's really important and that requires a yes culture so finally then my last question is what does make you really excited and positive about this country about europe about the world why not let's go for the whole humanity yeah i think it's a really important question actually which is like fundamentally my mother has ms i care deeply about her and how she is and able to spend her life ai will solve the most incurable of diseases within a 10-year time frame you think parkinson's we will have solutions to alzheimer's parkinson's multiple cirrhosis cancer wow in the next 10 years you really think that i really do i'm not saying there won't be other very challenging diseases that will come that will will absolutely be a problem but a hundred percent we will have if not complete solutions very meaningful movements to it wow in the world's most incurable diseases that is really fucking exciting have you seen stuff that perhaps the lay person isn't isn't seeing that makes you positive about that a hundred percent like when you look at the collation of human data and how some of the AI labs are using huge, huge healthcare data to proactively predict things like cancer and prevent them, 100%.

1:13:58When you look at NECO, the clinic in London that my friend Daniel and Shaq started, absolutely, this is preventing so many would-be cancer cases and saving the lives of mothers, grandmothers, daughters, sons. technology can be an incredible enabler for brilliance how long do you think you're going to live? you mentioned you take a Brian Johnson shake no I actually I'm very scared of dying but I always kind of thought I would die relatively young really? yeah I didn't mean that negatively no that's fascinating I don't think you can sustain in a sort of Kurt Cobain rock and roll way I don't think you can sustain what I do for that long but you'd like to live yeah no I'd like to but like I'm just like I don't think I'll live to like 150 I think you know you might live until you're 65 70 that's not bad I suppose it's pretty bad yeah it's not great how can we spin this into a wonderful heartwarming ending should I just say I hope you don't die no no no I think you know one of the I'm very aware of you know historical you know kind of health problems of my family right and a lot of that has been actually cancer related sadly and i do believe that ai will create very meaningful solutions to a lot of those problems and actually they may not be genetic problems anymore and actually that you will have again unbelievable breakthroughs in the most incurable of diseases and your loved ones will be around for a huge amount longer that is incredible all of the diseases that we thought were incurable could be solved wow that's cool that's pretty good harry stemmings live long and prosper what's that from star check star check thanks for doing this it's been a pleasure man loved it

1:16:03This episode of the Gentleman's Journal podcast is brought to you by Lin, the long-time maestros of exceptional home audio and makers of some of the most emotionally impactful speakers imaginable. A few weeks ago, in fact, the Gentleman's Journal team headed down to Lin specialist ripcaster just outside of Henley and were almost literally blown away by the ridiculously crisp and clear sound and chest-thumping bass that Lin's speakers produce. In particular, Lin's Magic System allows you to have that studio-quality sound in your own living room. It's the most accessible distillation of the whole Lin range, but one that produces the most gorgeous and clear sound imaginable.

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From the publisher

“You really have to be unwaveringly obsessed..."

Harry Stebbings’ career began at the age of 13, when he watched The Social Network — David Fincher and Aaron Sorkin’s brooding portrayal of the earliest days of Facebook. But whereas many of us watched that film and thought: “I’d quite like to be a tech founder”, Harry watched it and thought: “Gosh. I want to be a venture capitalist.”

A few years later, and with £200 pounds in the bank and not a single contact in the VC world, Harry started his podcast, The Twenty Minute VC. Now, more than 10 years and 1400 episodes later, Harry has pivoted his juggernaut-like podcast into his very own VC fund — one that has backed 13 unicorns to-date. Here, in a beautifully candid interview, Harry tells the podcast about the AI start-up sphere; why he chooses to work nine-to-nine, six days a week; how his often lonely childhood formed his entrepreneurial mindset; the dangers of social media usage; and the things that make him optimistic about the future.

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