On the 9th episode of Invested, Michael hosts Harry Stebbings, founder of 20VC, the largest media asset in venture with over $300M AUM and 13 unicorn portfolio companies in the last 5 years.
20VC’s portfolio includes Pachama, Tripledot, Linear, BeReal, Sorare, Roam Research, Merge and Nex Health to name a few.
Harry is also a passionate supporter of MS UK and male eating disorder charities.
You can learn more about 20VC at www.thetwentyminutevc.com
Please enjoy and rate this episode 5 stars wherever you stream your podcasts!
Follow Harry on Twitter: https://twitter.com/HarryStebbings?s=20
Follow Harry on LinkedIn: https://www.linkedin.com/in/harrystebbings/
Subscribe to Harry's podcast "20VC": https://www.thetwentyminutevc.com/
For show notes and past guests on Invested, please visit content.aleph.vc
Learn more about Aleph: aleph.vc
Sign up for Aleph’s monthly email newsletter: aleph.vc
Subscribe to our YouTube channel: https://www.youtube.com/@aleph-vc/
Follow Michael on Twitter: twitter.com/mikeeisenberg
Follow Michael on LinkedIn: https://www.linkedin.com/in/mieisenberg/
Follow Aleph on Twitter: https://twitter.com/mikeeisenberg
Follow Aleph on LinkedIn: https://www.linkedin.com/company/aleph-vc/
Follow Aleph on Instagram: https://www.instagram.com/aleph.vc/
Michael Eisenberg
Does it bother you that people, kind of, still consider you this, like, teenage podcaster?
Harry Stebbings
Yeah, I love it. Keep thinking I'm a podcaster.
Michael Eisenberg
Why? Another why, besides mum?
Harry Stebbings
Michael, I was a fat kid at school who was always told that they'd be the one, you know, that’s single forever and without friends. And, I was told that I was, like, the B student, not the A student. I was told that, whatever, whatever, whatever. And, you know what? I spent my life being underestimated. Being underestimated is one of the best superpowers in the world. Keep on thinking I'm a podcaster. And, I'll keep on writing $75 million Series B checks and leaving the round for triple dot, like we did. And so, you know what? It's okay. I don't mind, and this takes time, I think I did a lot before. Shak taught me so much about it, actually. You know, I remember once I wasn't on the list for, like, I don't know, some TechCrunch list. And, I wrote some snarky response to a tweet. And Shak was like, “Seriously? Seriously? You know what? Different game, Harry, different game. You have to change your game. What you did, now, to get here isn't what's gonna get you to the next level”. I don't mind what people think. I know what I'm doing. I'm operating against my plan. The plan is going exceptionally well and better than plan. And so, if people think I'm a podcaster, and they don't see it coming. Fantastic.
Michael Eisenberg
I am super duper, duper excited to put the man and the podcast on the other side of this mic. My friend, who is half my age, but for whom I have a tremendous amount of respect, Harry Stebbings. The man who was a teenage phenom, and now an investor. And- but, before we start, I just want to ask you something we ask all our guests coming on, which is: what is your core value?
Harry Stebbings
That’s a very, very good question. It's one that I might steal for my podcast. I think my core value is actually one that my dearest friend Shak told me. And, Shak told me that everyone is facing a battle that you know nothing about, be kind. And, I always think about that every day, whether it's to the barista in the coffee shop, or whether it's the CEO that you work with. And, I hold that one very, very near and dear to me. And, so I'd say that's my closest.
Michael Eisenberg
Be kind. I love it. And, I love Shak. As you know, I feel bad now that I gave him a hard time, many years ago, smoking a cigarette outside of the conference.
Harry Stebbings
He gives me a hard time for smoking too, so don’t worry.
Michael Eisenberg
Good. So, it is my utmost honor and pleasure to introduce Harry Stebbings, a man who needs no introduction. He's the founder of 20VC, one of the largest media assets in venture capital and startups. He also manages the fund 20VC, which has a couple of 100+ million dollars, 400 million dollars in assets, under management. The 20VC podcast reaches 700,000 subscribers, has over 120 million downloads, to date. Harry started this podcast without a single contact in venture capital, just with a lot of chutzpah. You know chutzpah is, right Harry? You live chutzpah.
Harry Stebbings
I live chutzpah.
Michael Eisenberg
He’s got a lot of chutzpah. He’s got 2750+ episodes. Over 1,000,000- 1.3 million plays per show. Guests have included, my former partner and friend, Bill Gurley, Howard Marks of Oaktree, founders of Spotify, PayPal, LinkedIn, Revolut, Checkout, yours truly, and many more, including recently, the Prime Minister of the United Kingdom, Rishi Sunak, in his residence, no less. How was their podcast studio, Harry?
Harry Stebbings
You know what? It was actually very lovely. It was quite a palatial run that we did it in, and we had a portrait of Maggie Thatcher hanging over us. It was a wonderful session.
Michael Eisenberg
I see that you're on a first-name basis with “Maggie” Thatcher.
Harry Stebbings
Of course.
Michael Eisenberg
Okay. At 22 years old, Harry was the youngest to make the list of the Forbes Finance 30 Under 30 in Europe. And, prior to 20VC, Harry was a partner at Stride.VC, a firm he co-founded in 2018, right after his bar mitzvah. Harry then went on to launch his venture capital fund, 20VC, in May 2020. He's raised a couple of funds, $33 million- no, more funds than that. And, most recently, launched the sales fund made up of sales executives. We’re gonna talk more about that soon. So, Harry, welcome to the show. Sorry for the mumbled and blundered introduction. But, nobody needs an introduction to you. So, I want to talk about how I first, kind of, got to know you and got inspired by you. It was the middle of Corona, I think it was. And, I read about your mom. And so, first of all, tell me about your “mum”, as you call her, “mom” in my American English. And, how that was, kind of, a motivating factor in your life.
Harry Stebbings 4:35
It's funny, I think everyone needs “why” to be driven to do anything, really. And, I think one of the worst things is, that we're told you have to do it for yourself. It's complete bullshit. You don't have to do it for yourself. You can do it, totally, for someone else. There is the “post-baby effect” that you see in entrepreneurs. Entrepreneurs are actually scientifically designed or programmed to be more successful, post babies. It's been proven. There is an internal “why” and for much of my career, you know, the “why” has been my mother. You know, she inspired me so much growing up. I always say she's the light in every room, which sounds quite corny, and it is. But, she's amazing! You know, she got to MS when I was very young, 13, goes through an immense amount of pain and struggle. And, she remains the best mother in the world. And, always there for me and always the rock in my family. And, I think it, bluntly, just gives you this awareness of how truly great people can be. And, how she's never given up, and never will give up. And, always has a smile on her face. And so, I learn, every day, from her. And, she drives me to be better, to do more, and to never give up on myself.
Michael Eisenberg
So, before I ask you, when do you get the baby? So that you can, kind of, get to the next leg of entrepreneurship. Yeah, how does your mum tie into starting the podcast?
Harry Stebbings
I mean, honestly, I was 18 years old, and I was at home. And, you know, I was in love with venture capital. I fell in love with venture when I was 13. I saw Peter Thiel invest in Facebook with Clarium Capital in The Social Network, which is a scene that everyone else has completely forgotten. But to me, it changed my life forever. And then, you'll know these writers, but I went home and I read Brad Feld, Roger Ehrenburg, David Hornick. And, I was just captivated by the early writers in venture. And, I fell in love with it. I had Howard Marks under the kind of, you know, duvet at boarding school. No wonder I had no friends. But- also saying Howard Marks under my duvet sounds a little bit wrong, Howard, if you’re listening, I'm sorry. But, to my point, I loved it. And, you know, we'll talk about burnout later, and why I think it's complete crap. But, when I was 18, I have this love of venture so much. So, I walked to school every day. And, on my walk to school, all I ever heard was Peter Thiel and Marc Andreessen on podcasts. And, I knew there was this slew of amazing, amazing VCs. And, I thought, “Why doesn't anyone interview them?”. And actually, I believed- the best companies, Michael, I think, personally, are built on insight developments. A way of seeing the world that is different to how others see it. And, I believe that venture would be personalized, that people would choose the partner more than the firm or as much as the firm. And, we deserve transparency in the system. And, I believed in the rise of media and content as the core vehicle for this personalization. And so, really, for me, it was this case of, “Okay, if these are my two contrarian beliefs at the time in 2015, what medium is perfect for me?”. And, sorry, you can just stop me at any time, but like, everyone comes to me and says, “You know what, I want to start a podcast”. And I'm like, “Why? You suck at talking”. And they go, “Well, it's what it's about now, everyone's doing a podcast, right?”. And you're like, “I repeat, you suck at talking.” You have to choose the medium that is right for you. And so, for me, I just love talking. I gain the energy from speaking with you now. I love learning about people's stories. That's why I did podcasting. And actually, most people maybe shouldn't do it. They should do short-form videos, tweets, some long-form writing, but you got to choose the medium that's right for you. And then, to another point of an investing lesson that I've learned, honestly, Michael, I was really lucky. Venture, in 2015, was so not cool! But, it was just becoming cool. And, podcasting in 2015 was so not in, but it was just coming in. I was at two very, very early waves that were about to explode, which goes to one of the most important investing lessons, which is market timing. It doesn't matter where you are in a field. If it's not hot, or it's not on the app, or it's not big enough, it's not going to work.
Michael Eisenberg
But it's hard to time markets.
Harry Stebbings
It's really hard to time markets, which is why I don't, generally, like to play the market timing game, because I'm not smart enough. I want to do something that I know has demand. I want to do, you know, international payments. Great. We know this is a business, but I don't want to do something which is inherently-
Michael Eisenberg
But, take back to your mom, like, so, at 13, you became interested in venture capital. At 15 you said “Oh, this is cool”, and you start listening to Marc Andreessen and Peter Thiel. And then you start this podcast.
Harry Stebbings
Yeah.
Michael Eisenberg
But why? Still, why? Not just because you'd like to talk. Or, was it just because you like to talk?
Harry Stebbings
No, it was because I wanted a job in venture. I wanted a job in venture, and I didn't go to university. Well, I went for a month, but then I dropped out. I hated it.
Michael Eisenberg
Did you go to high school when you were there? Or were you just listening to Marc Andreessen?
Harry Stebbings
No. I mean, I went to high school, and that's when I actually started the podcast, in high school. And then, when I went to university, I was earning about three grand a month, so 36 grand a year, about $50,000 a year.
Michael Eisenberg
From the podcast?
Harry Stebbings
Yeah. And, I was like, okay, like this is enough money to live on my own in London, that would be a sustainable source of income for me to be okay. And so, after a month I left. I think one of the biggest crimes, actually, is university. University should be banned, should be made illegal, unless you are doing anything like doctorates or, you know, vet studies or legal studies
Michael Eisenberg
Is there a Stebbings Fellowship, like there's a Thiel Fellowship?
Harry Stebbings
There will be. The fact that we imprison children from 18 to 21. Encourage them to get blind drunk, every day. And then, really just like captivate their minds with bullshit academics that you won't need when you grow up, in their most productive years, is literally criminal. I will give children- mind you, I've already said this to my family and my girlfriend, I will give my children 50 grand to go start a business, fail, learn, try, you'll do it for two, three years, and you'll come out and get a job and go “I learned these four things when I started a failed business”.
Michael Eisenberg
So children won't only be an entrepreneurial bug for you, it's already for them. You've got them out of the cradle and into business.
Harry Stebbings 11:02
Listen, they should be starting before 18. One of the earlier- you know, I ask this of all founders that I meet, which is like, tell me about how you first made money. Great, great entrepreneurs always have a story, you know this, they always have a story of “Oh, I was 12 and I was selling something on eBay. I was doing comic books and I was selling them at school”. Something. And, it's completely- everyone's like, “Oh, you know, it's only for the 1%”. And, you can say that bullshit, socioeconomically uncorrelated. And you can verify, 99% of the best have those early signs.
Michael Eisenberg
I worked at a cheese and fish store, for what it's worth. I guess if your talent was talking, mine was tolerating bad smells.
Harry Stebbings
I mean, there we go, this is a sign of true excellence.
Michael Eisenberg
So you're good at talking, you started a podcast, and you wanted a job in venture capital, and your mom was the shining light in your life that caused you to do this. And, you were bored sleeping with Howard Marks in high school. That's the summary of your career until age 18.
Harry Stebbings
Pretty much, Ray Dalio was busy. Yeah.
Michael Eisenberg
Okay, so, I want to dive right into a bunch of questions we got from people. So, in preparation for this episode, I did what you do, right? Twitter, work your magic. And, I put our short video on social media asking people what I should ask you when we put you on the other side of the mic. You retweeted it and wrote “I do not ever do interviews. but when Mike asked, I had to say yes. What do you want to hear me discuss? Preference for personal life, drinking, happiness, depression, media? But AMA, go. You said you were super happy before we came on air. You said you stopped drinking. Why were you drinking in the first place?
Harry Stebbings
I mean, the UK has a very normal, like, abnormal, I think, relationship to drinking. Where it's like, kind of, just so ingrained in our society from a very early age. And you know, I have a problem with drinking, Michael, if I'm honest. I find that not enough people actually say it. They'll bullshit and say, “Oh, it was health, it was calories”. And, the only way we're going to get a generation of people to accept it and actually say it's okay, and that's fine, and you can change and be better, is by having people speak up and say it. And, this man had a problem with drinking. I was drinking too much. And, I was drinking every day. And, you know, especially in our jobs, you drink every night, because you have dinners, drinks of entrepreneur events, VC events, and it just became a really negative habit in my life. And actually, it was just beginning to be a really bad influence in my life. And so, I stopped drinking. And, it was probably the single most meaningful thing that's ever happened to my life.
Michael Eisenberg
How’d you stop?
Harry Stebbings
Oh, I can stop doing anything. I am probably the most strong-willed person in the world. Which is not an arrogance. It is to the point of like, bad. Like, I will run when I'm injured, I will lift weights when I shouldn't lift weights, like, nothing will stop me, to the point when it's sometimes unwise. But, when I say I'm going to do something, I'm not going to do something, nothing will stop me. And so, for me, it was just a very simple, “I stopped drinking”. I use an app called I Am Sober. You press start. And then, you see the time that you're sober. Trust me, there is nothing like looking at that, with now whatever it is, 300 days, when you think that you want to drink, which I never do. But, if you ever do, when you see that, and you have to restart, that sucks. Also, the biggest problem that people have with habits, Michael, is they always think about the reward, not the action, okay? And so, they always think, “Oh, I'm gonna feel great when I have that drink”. And actually, it's not about that. It's about, like, the after-effect. And so, there's the action, and then there's the after-effects. And they go “Great. I want the action, I want the alcohol, I want the Espresso Martini”. The after-effect is 200-400 calories and a hangover. No one thinks about that. It's the same with good things. Like, every morning, I will never miss my alarm. Everyone thinks about the action, “Oh, I can sleep in”. But, the after-effect is: and I'm 20 minutes late for work. Think about the after-effect, not the action. And, they will change pretty much everything about the way that you do, often, very negative things. And so-
Michael Eisenberg
As you’re talking about that I'm thinking about zero interest rates. And, the hangover from that. So, how did you develop this kind of indomitable determination to, kind of, be able to do anything? Where'd that come from?
Harry Stebbings
I was very fat when I was younger. And I think we also-
Michael Eisenberg
I would never guess that!
Harry Stebbings
And, we're too nice. Like, we're far too, and I'm probably gonna get canceled for this show, but, we're too nice. Everyone's like, “Oh, you can't say fat. You should have to say round, or well, well-sized”. No, I was fat. I ate KFC family buckets, and I was fast. It's okay. But, I was very fat. And I lost a huge amount of weight, very quickly. And, bluntly, it showed me that if I put my mind to it, I could achieve it, I could do anything. And, I think we all like to tell ourselves that, actually, it's okay. And, no one knows what they're doing. And like, we all look for the comfort. That's not okay. Like, you should be uncomfortable. Today, I like, seek discomfort. I just finished a run, which is probably why I'm sweating. And, it was a really uncomfortable run. It was really hot in London, but only through going through that discomfort do I sit with you now, and I'm absolutely fucking pumped.
Michael Eisenberg
Oh, it's not just because of me it’s because of your run?
Harry Stebbings
It’s not just because of you, sadly. Ray Dalio has given me a tickle under the table. But, like you've got to go through that. And so, that's where, honestly, I think the seed of it was, where I saw that. I lost- I went from 125 kilos to 75 kilos, in five months.
Michael Eisenberg
Wow.
Harry Stebbings
Yeah, it's 50 kilos in five months. Everyone's gonna be like, “Oh, it's so bad for you to do that, It's so bad for you to do that”. You know what I say to all those people on Twitter? I don't care about you. Literally.
Michael Eisenberg
Harry, I just want you to know, this is a totally safe space for political incorrectness. It's all good. We're the same on this. But, that leads me to a question, by the way, which is, so here comes this 18-year-old kid, he launches a podcast. It's the most popular thing in venture capital and entrepreneurial journalism, if that's the right word, or media, for today. The mainstream media is, kind of, not exactly having a romance with tech and venture capital, these days. How do you think about what you're doing, versus where mainstream media is at today, particularly in regards to tech?
Harry Stebbings
I mean, I, honestly, I think journalism sucks. If we're totally honest, Michael. We started this conversation, well, we all read it, they didn't really know what they're talking about. They write, kind of, bombastic articles that are there for clickbait. They're not very well researched, on the whole. Some are, there's always nuance. 3% are, and they're great. You know, but the majority is not. They have a business. Business models drive incentives, you have to understand the incentive mechanism. And, they will take a snippet, put it as the headline, because it drives clicks. And, they will ignore most of the good things you say, because it doesn't drive clicks. And, that is their business model. And so, I think most of, honestly, the quality of journalism today sucks. I think most of the journalists want to be VCs. I think they’re all overworked, they are all overworked, which I feel really bad about. Like, they don't have time to do a lot of the research, which is really tough on them, because a lot of them are good writers. A lot of them are given stories they don't want to write about. Let's not get on to PR firms, because they are terrible, and 99% are useless. I'm really making friends here.
Michael Eisenberg
It’s good. It’s good clickbait for this podcast.
Harry Stebbings
Thank you so much. There you go. Welcome to modern media.
Michael Eisenberg
But, you know, you said that they're overworked, the journalists. You work pretty hard yourself. I mean, you and I have had dinner in London, it's pretty late at night, and you will go back to work after that, sometimes.
Harry Stebbings
Sometimes! Sometimes. Every time! People need to know the work that goes in. Because, like, you don't get there without the brutal, grinding work. I get so many McKinsey grads, people, saying to me, I'm going to start the 19 Minute VC, the 18 Minute VC. And, I'm just like, good luck. Let me help you. Like, I really wish you well, because you will have to give eight years of your life, your health, everything, to this, to make it what it is, in a market that's harder than I did it in.
Michael Eisenberg
But, one of our mutual friends is an investor- I'm not sure if she's an investor with you, Kathryn Mayne said, “Is Harry going to burn out?”.
Harry Stebbings
Oh, I love Kathryn. So period, love Kathryn. But, the topic of burnout is just absolutely, for me. And, again, a lot of people take everything as like “Oh, he’s-” this is for me. So, for anyone who's upset or emotional about me saying this, it's just for me. But, burnout, for me, is when I'm doing something I don't love, and it's crushing my soul. Which was when I had a job, which was, admittedly, many years ago. But, I love what I do. Like, Michael, this is my job. I'm about to interview an amazing, amazing founder, later today.
Michael Eisenberg
Who's that?
Harry Stebbings
One of the founders of Plaid. And like, that's awesome. That's my job, too. I have a board meeting later today with an amazing company. Am I gonna burn out? Oh, Christ, I've got, you know, an iced coffee brought to me by an EA in a beautiful office. My grandfather shovels gravel on a golf course for $12 an hour. Okay. And, we talk about burnout? I think this is like a luxury, in my space, for me to be talking about burnout. I love what I do. I work with amazing people. And, I'm more energized than ever. So for me, I don't worry about burnout. I think it's a real thing. And it happens to people. But I think if you really love what you do, it's hard to do burn out.
Michael Eisenberg
So, our mutual friend, Shak, said I should ask you, what did you learn from the markets in 2021, 22, and 23. So, I know a lot of people got excited. And, you know, this is like my third or fourth cycle. And, I saw a lot of people in 98, 99 be super energized. And then again, you know, in 05, 06. And then, you know, through the teens, and they were super energized. And, they were working really hard. And, you know, everything was great. And, everyone was a genius, which is, by the way, the totality of your career, so far. What have the new learnings been like, for you, has it impacted your energy at all? And, I'll ask the follow-up question afterward.
Harry Stebbings
Good. So yeah, there's been a huge amount of learning. It- has it impacted my energy? Not at all. Let's go through the lessons. Now, again, I find people on- I do what you're doing now, often, and people don't- The best interviews are made up of art and science, okay? The art is where you talk about the story, it resonates with people, you bring people in. And then, the science is what you learned. The thematic, the tactical. And so, let's let's do this, let's do the science and the art of what I learned. Number one, I learned that a company is more than a piece of paper with numbers on it. And, what do I mean by that? I made an investment in Pakistan, Airlift, quite well-documented, very poorly documented in terms of, like, the amount of money that I put into it, and, kind of, my name and attribution to it. But again, we will leave journalism to journalism. And so, I made an investment in airlift in Pakistan, the numbers look great, everything looked great. The caps were fine, the LTVs were great, the unit economics and the business, on paper, was very attractive. Now, in the real world, it was in a country with political risk, with currency risk, with weather risk. And, I didn't factor in the very many negative externalities that can really damage a business. And, actually, the idea that a great founder can make any business happen is complete rubbish. You cannot have a great founder in a market which can get crushed by corruption, politics, weather. No matter how good you are, as a founder, those things can crush you. And so, I just learned that, bluntly, you have to really be quite holistic in how you understand and evaluate businesses. And, I said this to my girlfriend today. You know, she said, “How do you know what founders to invest in?”. And I say, “Ah, you're Australian. So let me help you here. You need a great surfer. But that's not enough. You need, also, a really great beach with fantastic waves. But, that's still not enough. If you go in the middle of the night, you're not going to do much surfing. So, you need the right beach, the right surfer, and the right time of day for that beach, to really go surfing.” And, I think this was a real articulation of that, because I don't think I quite looked at it holistically, and I was too focused on singular strengths within the business.
Michael Eisenberg
Did you meet the founder in person?
Harry Stebbings
Yeah, I did. Yeah.
Michael Eisenberg
Did you go to Pakistan?
Harry Stebbings
No, he came here. But, I stand by where you're going, 100%, on that. I think the return of in-person is crucial, people hate me for this too. I think really, you need to meet the founders in person, as well, you gain so much from that tangibility-wise. And so, I totally get where you're going with that. I think another one, honestly, is like portfolio management, liquidity-wise, you know, there were positions that I should have sold. And, I didn't. And, I think we were trained, bluntly, and I’m not blaming the younger generation of investors, we were trained to hold onto your winnings, this is what the best told us. And, we listened. And, we did. And, bluntly, there are three or four where I should have been much more proactive in selling. And, I should have been much more strategic about that. And I wasn't.
Michael Eisenberg
You know, by the way, “hold on to your winnings” is a good strategy, if you actually know which the long-term winners are. The problem is that there's a survivorship bias to it. And so, you actually don't know, most people don't know, in the moment, that it was going to be a winner. I think about 2001, I lived through that.
Harry Stebbings
But, this is fundamentally why I don't like reserves. Reserves, I think, are actually financially irresponsible, in a lot of cases. And you're gonna go “Whoa, oh, Harry, you’re going for this one”.
Michael Eisenberg
I want to clarify for people listening, what reserves are is, venture capitalists invest some money upfront, and they keep money to invest in the company as it matures, or gets into trouble, or whatever happens.
Harry Stebbings
Yeah, absolutely. And so, why do I think that it is often unwise? Because most often, reserve allocation is aligned to trajectory and to speed of growth within companies. Oh, X company has hit an inflection point, Y company’s got adoption, we want to put more money, we want to put more money in. Consistently, across the board in venture, if people were to have done that, they would have put their money in, kind of, the fastest growers, which, most often, if you look at the data, it's not the sustainable growers. If you looked at my portfolio, that would definitely be the case. And, it would have been financially unwise, which I'm thrilled that I had no reserve strategy. Actually, when you look at most portfolios, the best-performing companies, often, as the kind of, mid-performers in the early days, the ones that took a little bit of time and then found something, the ones that just went straight out the gate, often hit snags, actually, later on, and the trajectory tails off. And so, for me, I personally feel that it's too difficult to know which of your companies, within the first 18 months, you should really concentrate capital into. And so I do take that approach.
Michael Eisenberg
So, it's now 2023, and the market’s down and liquidity has dried up and growth capital has disappeared, in many cases, not fully. But, it's gone. And so, I'm sure when you got started in this business as a venture capitalist, you just assumed that the later rounds were there. Now they're not. What has that taught you?
Harry Stebbings
What, that later rounds aren't there?
Michael Eisenberg
Yeah. Or maybe, has it taught you anything about investment pace?
Harry Stebbings
Um, no. I'm 40% deployed. Two years into my fund cycle. Will be a three to three and a half year deployment-pace,
Michael Eisenberg
Amazing.
Harry Stebbings
All of my LPs are going “Harry, we expected you to be the fastest.”
Michael Eisenberg
Well done.
Harry Stebbings
Thank you. And so, no. I've always been a big fan of temporal diversification, which, for people listening, is, essentially, that there are benefits to investing, kind of, overtime across cycles, because you'll get kind of a blended exposure over time, really. And so, I've always very much believed in that. And so, I was always very wary of that. And, you know, the other thing that's honestly true, Michael, I don't live the same life as a lot of other VCs. I’m not predicated on fees. Like, this is the other thing that we don't talk about in this industry, which is that a lot of funds are predicated on fees. And, funds are a business, as well. I have a business of media, which makes me more money than funds. I'm not here to raise funds fast and stack fees. That is not my game. Also, you want to talk about finding happiness. You know what? When I was 21, and super honest, I have no idea why I'm so honest with you, Michael, you're bringing out my honesty. But, I sat on my balcony when I was 21. And, I looked at my bank and I had a million pounds in there. And, I used to watch I'm a Celebrity- Who Wants to be a Millionaire. And, that was like happiness, when you're a millionaire. And, I had never been as unhappy. I had no friends. I was drinking a lot. I was quite unhealthy. I didn't actually have that much of a great relationship with my family. And, my mother, sure, but not my brother or anyone else. And, I was less happy than ever. And, I think this is the biggest problem with people is like, they don't actually know themselves. And, it's like, you know what makes me happy, Michael? My Sunday walks with my mom, spending time with my family, going to a spin class, things that cost $20-$30, at max. And actually, that’s what makes me happy. I think people don't know who they are. And, I think they don't know what they want, what they actually want. And, when you actually know those two things, it just changes a lot about how you think about life, for me.
Michael Eisenberg
What turned it around there at 21? So, there you are, drinking there, you were not happy. But, you know, your podcast was succeeding, and your financials. What turned it around?
Harry Stebbings
Nothing. I continued drinking. I continued making more money. And, I didn't realize. It took a long time, actually.
Michael Eisenberg
So, when did you?
Harry Stebbings
When did I realize that it wasn't okay? I think on the drinking, there were bad times. You know, there are times when you wake up and you just feel like absolute shit. And, when that happens time and time again, it's the most crazy thing. You know, you will feel like crap, time and time and again, and you'll get up and do it again. It makes no sense. And so, I think, you know, honestly, I turned 25. And, I believe that everyone is capable of really achieving greatness. I think most people, like, want to tell themselves that mediocrity is fine if we're honest. But, I think everyone's capable of achieving greatness. And, I thought, if I'm 50, and every year I lose 20% of my productivity because of alcohol. 20%. It's not actually a huge amount, but it's very significant, actually, stacked. Over 25 years, compounded, that's the difference between good, and really, really great. And, I am terrified of thinking, at the end of my career, I could have been so much more. And, I'm not more because of alcohol, because of the nights out. Seriously? And, actually, I really want to be a good father and a good parent. And, you know, I'm not going to be that, and I'm not going to be fresh to play with them in the park. Because I had a night out before, at a dinner? Is that really who I am? That doesn't sound like someone I want to be. And also, reliable. You know, someone- I asked someone recently, what do you want on your tombstone? And, they said, “I'd like reliable”. And, I thought, oh, fuck, that's boring. And, they said no. Being reliable is probably one of the greatest compliments you can be.
Michael Eisenberg
What do you want on your tombstone?
Harry Stebbings
What do I want on my tombstone? Knackered.
Michael Eisenberg
Rest in real peace.
Harry Stebbings
I think honestly, like, content. Like if you were content-
Michael Eisenberg
We’ll never be content.
Harry Stebbings
No, but if I'm dead, then hopefully, I will be. But also, you should never be content.
Michael Eisenberg
Right.
Harry Stebbings
You should be appreciative of what you have. I'm very appreciative of what I have. I love it on Sundays, knowing that I've got a week ahead of me, that I love doing what I'm doing. But, I'm never content.
Michael Eisenberg
Did that million pounds in your bank account, when you're 21 on your porch, change you in any way?
Harry Stebbings
No. Like, this is the other thing, Michael like-
Michael Eisenberg
What’d you do with the money?
Harry Stebbings
Keep it, I don’t want- I don't wear watches. I don't- I legally can't drive. I have zero interest in fashion. I don't like furniture. I don't like cars. I like venture capital and startups. So, which is why I find it so funny that people who focus on the money, don't make the money. There's inputs and outputs. Money, for me, is the output. And, the input is doing the work that I love.
Michael Eisenberg
By the way, there's a lot easier ways to make money than to be a startup entrepreneur or a venture capitalist, for that money, for smart and ambitious people. It requires a certain amount of- for founders in particular, a certain amount of, kind of, you know, craziness, a crazy gene in there, that you got to get after this and beyond it and, so-
Harry Stebbings
This is the worst way to make money, for sure, in terms of like, if you want to wait very, very long times. But also, it’s important to say, I did about 125 shows before we made a dollar on 20VC. Two years of shows.
Michael Eisenberg
How'd you pay for it?
Harry Stebbings
I mean, it was $50. It was dirt cheap. Like, you know, I had a laptop from school, which, you know, 15-year-olds have. I had a bedroom. And, I used, you know, all the free tools on the internet. This is the beautiful thing about the internet when you think about it. A kid from London cold emails Guy Kawasaki, and gets him to come on a podcast that doesn't exist! And, that makes, now, millions of pounds from like $5.
Michael Eisenberg
Was Guy your first guest?
Harry Stebbings
Yeah.
Michael Eisenberg
That's amazing. I love Guy. I haven't seen him in a bunch of years. So he, you know, he was a legend. Yeah, you know, in the late 90s, early 2000s.
Harry Stebbings
Yeah. And so, but, I think it's important to know that, like, you know, it takes time. This is the biggest reason why people fail with content. Which is, bluntly, they give up too soon. There’s many reasons why they fail. They give up too soon. You just- it's a game of who can survive the longest. Jason Calacanis taught me that early, actually, to be fair, credit to him. He taught me it's just a game of who can survive the longest, just keep going.
Michael Eisenberg
Jason’s amazing. I just ran into Jason in Abu Dhabi. And, we were reminiscing about his time at Silicon Alley Reporter, which nobody remembers anymore. So, you know, the media outlet, Silicon Alley Reporter, is not around, but Jason Calacanis is killing it on All In, his podcast.
Harry Stebbings
Yeah. And, it's just about surviving the longest. I don't think that people make terrible mistakes on content. They try and go so broad. I have so many people that are reading stories of entrepreneurship. And, it's like, when you inject yourself in the market timing of a cycle, changes a lot about the content types that you do. Like, we are coming in at a much more mature stage of content than five to eight years ago. So, you have to be incredibly specific. You want to do Israel or Jerusalem-based SAAS founders. That is your starting point. And, you want to own that tiny market. And then, you want to do Jerusalem and Tel Aviv-based SAAS founders. And then, you want to do the region of SAAS founders. But, a really important lesson that I always think to, you have to earn the right to do the next thing. And, I think too many people don't think about, kind of, step functions of expansion. But, you have to find product-market fit with that first 100 users. I think it's very much the same with founders today. Like, just find the first 100 users. And, you know, I cold-DMed on Twitter, like every single person who followed me, up until 40,000 followers.
Michael Eisenberg
Wow. Yeah. That's amazing. So, I'm gonna just go back to Shak's question for a second, to switch. If you could turn the clock back to, you know, the fall of 2021. Which is, by the way, when Gurley and I came on your podcast in November and talked about the impending downturn. Other than, kind of, selling some secondary in your portfolio at the top of the market, what else would you have done differently?
Harry Stebbings
I wouldn’t have sold the secondary one. I would have been much more- I wouldn't have done Pakistan, I wouldn't have done emerging markets. You're not smarter than the market. Again, I'm gonna get hate for this. Emerging markets are really hard. They're really, really hard. And, everyone's like “Oh the growth of Pakistan, the growth of North Africa”. Where's the liquidity coming from, Michael? It's gonna go on the NASDAQ, is it? I don't think so. I don't think so. Everyone points to New Bank. New Bank is a phenomenal company. David Velez is exceptional, exceptional. Like, once in a generation founder. But they're very, very rare. Very rare. And so, I'm just like, I would have been much more cognizant of that. I don't think there's more on the market, bluntly. Like, did we pay too high a price? Yes, we all did. Do I kind of blame any of us for that?
Michael Eisenberg
You gotta play the game on the field as Gurley says, right?
Harry Stebbings
Yeah, I blame the growth investors for doing 1200X ARR for some of my companies, but also let's not throw shade. When they were doing it, I was welcoming them. And so, I think it's easy to throw stones in those cases. I think it's quite humorous, that like, I will never not be more active on portfolio management than in the future, having learned what I've learned. I will absolutely take the lessons from Pakistan and from Airlift. What I find entertaining is the fact that there's a generation of investors who went through 08, who went through the.com, and still fell for this.
Michael Eisenberg
Yeah, I don't know what you mean by fell for this. What does it mean to fall for it?
Harry Stebbings
Who succumbed to 1200X ARR prices. Who succumbed to 12-month deployment cycles. Who succumbed to crazy emerging markets investing at the same price as US investing. When they’ve seen it before.
Michael Eisenberg
So, just a side question before I get onto the main question I wanted to ask you about this. So, London or the UK. Is that an emerging market for venture? Or, is it a well-established ecosystem?
Harry Stebbings
I mean, what, for venture?
Michael Eisenberg
You're laughing nervously, Harry.
Harry Stebbings
I'm laughing because I'm thinking of London as an emerging market. If this is an emerging market, wow. No, London is not an emerging market. London is an amazing, amazing place to build a business. We- I think we have, actually, very poor levels of venture, by the way. I think there are very, very few seed funds, series A funds, or growth funds, that are any good. So, fuck it, should we just burn the bridges of venture in Europe? Like, the great seed funds in Europe, Point Nine, number one. Visionaries, number two. They're rising and they’re the competitor to Point Nine. Okay.
Michael Eisenberg
And, what about you?
Harry Stebbings
Listen, I will always promote others and people can make their own mind up.
Michael Eisenberg
By the way, is early stage the best place for you to invest? Katherine Mayne asked me this question. Or, should you be, kind of, a later-stage investor?
Harry Stebbings
I don't categorize myself as an early-stage or late-stage or SAAS investor. My job is to- and I don't know how you feel about how you categorize yourself, but like, my job is to make great investments in category-defining founders and make a huge amount of money for my investors. Yeah, it's that simple. And so, I don't like to box myself into- what does early stage mean, is series A and B early stage? If you're a post-IPO, then perhaps series D is early stage. So, I'm just like, my job is to partner with the best founders in the world and make them pick me. I don't even think I'm an investor, Michael. I think I'm a founder. My job is to create products that the best founders in the world want to take.
Michael Eisenberg
Expand on that.
Harry Stebbings
Money Sales is a great example. Yeah. And so, the media is another great example of that. We have an incredible data team and data product. That is another example of that. We, by far, could do the best fund of funds in the world. We have 30,000 references on 3,000 GPs from 10 founders, each, that they sit on a board with. We have 2,800 track records. By far the most comprehensive data on this generation of venture investors. I’m creating products because I need to win the best founders. And, my customers are just founders. It's that simple. And so, I don't really like the whole, like, “Oh, are you an earlier growth, where do you sit in the stack?”. My job is to build products for my customers, and my customers are founders, and that's it.
Michael Eisenberg
When we started all of it, Eden and I, so, he said, “Hey, I just want to make sure we're really an equal partnership”. I said, “What's that?”. He says, “I want to spend a lot of money on a data platform”. And this is, by the way, 2012 or 13. And I said, “What's that?”. And he says, “Well, I've got this spreadsheet of angel investors and of references and of founders and of connections. And I want to instrument the whole thing and hire developers and product managers into Aleph, what do you think about that?”. I said, “Well, it's an equal partnership, you get to make that decision.” We have this system now, called Amplify, which has millions and millions and millions of connections. By the way, we do the same thing. We have automated reference checking on engineers and marketing people and investors. And, by the way, I get a list of “Hey, so and so wants to get in touch with this investor”, email automatically teed up, because it's already, kind of, been preprocessed by our system. And, kind of, we know what they're looking for, what they're not looking for. And we've- it's a massive network. And, it's like, you know, it’s a killer competitive advantage. And, by the way, as the old guy, you know, I'm responsible for none of it. It's my partner Eden that is, but I look at young people like you, and Eden is older than you, and say, “Wow, what made you certain that that was worth the investment?”.
Harry Stebbings
Oh, I wasn't.
Michael Eisenberg
That's a great answer.
Harry Stebbings
This is the other thing, we always backtrack and we say “I knew this”. I didn't know this, I didn't know most of the shit! I will probably sound really arrogant in this show, most of this stuff you figure out along the way. And, I think that's the number one thing that I find so funny with a lot of early-stage investors, when they're like, “Oh, I don't find the defensibility”. It's like no, no one has any defensibility on day one, it’s built over time with process, with reference, with customers, team members, with portfolios. And so, for me, it was basically a data acquisition interest, that then turns into a data product, that then turns into a platform, and strength compounds over time. You get stronger by doing the reps and by going back to the gym. And, that’s what I saw here, which is like, it just compounds over time, and it gets better and better and better. And, the show is actually an amazing data acquisition strategy. I think, when I heard you talk about the data platform there, that the thing that I actually think when I heard that was, something that Hunter Walk and Sacha Patel told me, which is, partnerships are often most successful when both of you are rich already. And, I don't mean to talk about your personal wells, but, you're not resting on the fees to pay rent. Which actually makes the decisions that you make a lot higher quality and purer, because you make them in isolation, without personal need coming into it. It’s for the best of the firm. And, I thought that was a really interesting lesson that Hunter and Sasha took from their building of Homebrew. And, it made me think of that when I heard you say about the investment in the data team, which, naturally, takes away from your fees.
Michael Eisenberg
Tell me something. Like, how did you get up the gumption to reach out to Guy Kawasaki? And, who were the other, early, you know, I guess, guests on your podcast or show or kitchen, or bedroom-
Harry Stebbings
I think this is like, you know, the other funny thing, which is like, you know, people say this to me a lot, which is like, “Oh my gosh, weren't you nervous?”. No. I was really nervous to speak to friends my own age, like at a disco. Terrifying. I still find it terrifying. Like, I was the one in the corner. I don't know how to dance, Michael. I don't know what to do. I'm deaf in one ear. It's just awkward. But, speaking to a CEO of a massive business? No, it's not very nerve-wracking because we share a passion. Because I love what you do. And I'm really interested to hear your answer.
Michael Eisenberg
But how about speaking to the Prime Minister of the UK?
Harry Stebbings
No, it wasn't- I didn't mean it- no, I'm really passionate about the UK and about European tech. Why would I be nervous?
Michael Eisenberg
Bill Ackman?
Harry Stebbings
No. Like, I didn't get nervous. I mean, I was nervous when Howard Marks told me-
Michael Eisenberg
He was my next question, Howard Marks.
Harry Stebbings
Howard Marks told me, “Well that’s a stupid question”. Suddenly, I was struck with a little bit of nerve. And, Bill came in and saved the day and was like, “Okay, well, I mean, let's just calm down, Howard”. Which was very kind of Bill. But like, no, I didn't get nervous here. Because, I think, honestly, I do the work. I really do the work. We prep, intensely, before each show. So we're ready when we step on the field, one. And then, two, I'm passionate to listen, I want to learn. Every show that we do- by the way, I only release 70% of shows we do, 30% don't go out. So-
Michael Eisenberg 48:52
How pissed are those people?
Harry Stebbings
Not too pissed. And they're not pissed because we have a full-time TED coach on staff. Like, former TED speaker coach, on staff, who analyzes the transcripts. And then, we'll say, “Michael, in your intro, it wasn't as cohesive as it could be. If you did one, two, and three, you could tie it together a lot more succinctly”. And, they'll coach you on your speaking style. And so, we try and give quite a lot back, as a thank you. And actually, if it's not a good representation of you, then it's not the best version of yourself in the world and present yourself. But like, I need to learn three to five things, per show, still today, for it to go out. And so, you know, this is the other thing, like, you know, Gustav Soderstrom, at Spotify, the CPO of Spotify, says one of the best quotes. And, he says “Details are not details, details are the product”. And, I am passionate about delivering the best product, every single time. And, if it's not, like, the best product, it's not going out. Just like product designers don't ship not-good product. I'm not going to ship a mediocre podcast.
Michael Eisenberg
You know, I didn't ask your founders what they think of you before the show. And, none of them seemed to DM me, unlike many other people who did. If I asked your founders what they think of you, as an investor or a board member, what would they tell me? What would be the feedback?
Harry Stebbings
I think that's a-connected if we're honest. I think I don't believe venture investors are generally very well-positioned to help founders. Like, I just don't. I think the best people to help founders are people in the trenches, who are operating, in real-time, and are facing those problems, right now. If you are hiring a Developer Relations Lead, it is not right to speak to your ambassador about it, honestly. It is probably right to speak to the best technical recruiter at Slack, at MongoDB, who is having that exact challenge. Who will help you write that job description? Who will help you get that diverse candidate pipeline? Like, that is where real value lies.
Michael Eisenberg
Is there gonna be a $5 million developer relations venture capital fund from 20VC, soon?
Harry Stebbings
You know, it might be a little bit niche. But, you never rule it out, Michael. But, like, it is not, like, the venture investor who will be able to deliver that value. And, people also forget the decay in operating experience. People are like “Oh, well, X was an operator”. He was an operator or she was an operator, in 2012. This was, kind of, at the birth of cloud, in the very early days of cloud. This was pre-COVID, when work-from-home, hybrid, and millennials, weren't a nightmare. The world has changed so much, the rate of decay on operating experiences has never been greater. Actually, you need people in the trenches, who can deliver that value. So, my job is to be the best switchboard in the world, to deliver real value to my entrepreneurs, and to the founders that we work with. Why did we do 20 product, 20 growth, 20 sales? Because, now, we have 100, of the best operators in the world, on WhatsApp, ready to go, who we have great relationships with, we've delivered value to them, already.
Michael Eisenberg
So, take 20VC’s money, because you'll have access to the greatest network in the world. So, it's not just money. It's money and access. That's what you're offering? Anything else?
Harry Stebbings
I would say more. It’s money, and access, in real-time, to the best people. Like, a lot of people like access- access, and knowledge. And, what I mean by that is, like, there's access, which is, I want to speak to X and they're able to connect you. We’re a little bit, I think, more intelligent than that, which is like, “Hey, this is my problem, help me solve it”. And then, knowing the exact right person, at the exact right company, at the right time, and then being able to connect them within a day. That, I think, is very, very powerful and unique, especially from Europe to the US. More in the US, you have firms that do that. And then, I think, also content. Yeah, every company's question today is, “How do I scale customer acquisition in an economically efficient way?”. Every firm is becoming a media and a content firm, as well. And, knowing how to do it, it takes years, and years, and years.
Michael Eisenberg
You know, on that front, does it bother you that so many people out there in the media- But, I guess I'm asking you a psychological question, almost. I think this came from Shak, too, by the way. Does it bother you that people, kind of, still consider you this, like, teenage podcaster? Does it bother you?
Harry Stebbings
Yeah, I love it. Keep thinking I'm a podcaster.
Michael Eisenberg
Why? Another why, besides mum?
Harry Stebbings
Michael, I was a fat kid at school who was always told that they'd be the one, you know, that’s single forever and without friends. And, I was told that I was, like, the B student, not the A student. I was told that, whatever, whatever, whatever. And, you know what? I spent my life being underestimated. Being underestimated is one of the best superpowers in the world. Keep on thinking I'm a podcaster. And, I'll keep on writing $75 million Series B checks and leaving the round for triple dot, like we did. And so, you know what? It's okay. I don't mind, and this takes time, I think I did a lot before. Shak taught me so much about it, actually. You know, I remember once I wasn't on the list for, like, I don't know, some TechCrunch list. And, I wrote some snarky response to a tweet. And Shak was like, “Seriously? Seriously? You know what? Different game, Harry, different game. You have to change your game. What you did, now, to get here isn't what's gonna get you to the next level”. I don't mind what people think. I know what I'm doing. I'm operating against my plan. The plan is going exceptionally well and better than plan. And so, if people think I'm a podcaster, and they don't see it coming. Fantastic.
Michael Eisenberg
Do you make all the investing decisions?
Harry Stebbings
I have a precede partner, Keiran, who I work with on precede, but across the firm, yes.
Michael Eisenberg
How do you stay humble?
Harry Stebbings
I have a mother that kicks the shit out of me.
Michael Eisenberg
It’s not your girlfriend. It's your mother.
Harry Stebbings
Yeah, no, girlfriend doesn't, it’s mother that does. Um, honestly. What is success, Michael? Like I'm not successful, okay?
Michael Eisenberg
I know but wait, hold on, hold on, hold on. How many emails do you get a week from people who want to go on your podcast?
Harry Stebbings
200
Michael Eisenberg
200. How many people come over and say “I want to be, or I can be, maybe, the next Harry Stebbings, and at 26 I'll have the most popular VC podcast, my own venture fund solo GP.”? Lots, right?
Harry Stebbings
But is that a success? This is something that I just think more and more about, which is like, you know, someone very close to me, earns $30-40 grand a year, you know, which is absolutely fine, but it's much less an average salary in the UK. And, every day, they go and hang out with some friends at the end of the day, and then they go back to their wife, and on the weekends, they play sports with their friends. And, they go to the cinema, and they seem very happy. And, I just think that we wrongly categorize success as a number in HSBC. And, it's just not that. And, actually, in many ways, that person is much more successful than me. You know, me with psoriasis, you know, alcoholism, and heart palpitations sitting at my desk at 1 am, cranking.
Michael Eisenberg
Is success and happiness the same thing?
Harry Stebbings
It’s a good question. Can you be unsuccessful and happy? Yes, you can.
Michael Eisenberg
So, they're not the same. So, how do you define success?
Harry Stebbings
I think, for me, it's nuanced. Like, for some people- and this is the other thing that's terrible is like, you know, we tell people that you shouldn't do it for money. If you do it for money, and that's your “why”, I think that's fine. And, for some people, success is the money. For me, it's not. It's loving what I do and never feeling imprisoned, or feeling free. You know, technically, now, I can do, you know, you control your day, I control my day. Now, really, we do and we don't, it's a little bit constrained. But, technically, we don't have a boss to do that. That, for me, is a huge luxury and success, in many ways. For other people it's not. So, I think it's really dependent on the person. But I think, you know, yeah, I think it's very dependent on the person. But, I think you can be successful and you know, unhappy as well.
Michael Eisenberg
How do you know if you're gonna be a successful venture capitalist? Or, if you are a successful venture capitalist? I mean, you've been through a massive bull market run, there's been a downturn now. Like, how do you know if you're good at this, even?
Harry Stebbings
I don't think you do. I don't think it takes 10 years to know if you're good at this. Everyone's like, “Oh, it's 10 years''. That's not true. You can look at it and be- it's not follow on funding, that will be a skewed metric. Let's take a look at how many companies, within your portfolio, doing sustainably 10 million in ARR or above, within a certain amount of time frame. Let’s look at the quality of revenue, the quality of margins, the quality of customers within portfolio companies. You can quickly tell, within a three to five-year period, whether you have decent enough access and picking to be a good investor. When you think about ventures today, Michael, and it’s so funny that I'm telling you, someone that I respect the shit out of, as a venture investor, and learn from daily. So, this is ironic for me, but for people listening, you know, there's three pillars, to me, of successful venture investing. There's sourcing, finding the best companies and founders in the wild. There's selecting, which is picking those best founders. And, then there's helping, which is ensuring they have all they can to be as successful as possible. I create products for those three. How do you know whether you're successful? I think, honestly, you take what I said before, and you can tell early signs within those first three to five years. But, cash is king. And, as a lot- of the reason I don't do podcasts, and I've probably sounded very arrogant in this podcast, but the reason I never do podcasts is because I have not returned cash. And, there's a lot of young people today who like to chat a lot of shit. And, actually, their LPs are still waiting for dollars back. And, you know what? I'm just very wary of that. Which is why I do this with you. But, generally, I think we should do more work and less talk,
Michael Eisenberg
That's super authentic. Noah Tradonsky asked, who haven't you interviewed that you really want to interview?
Harry Stebbings
I mean, I was talking about this with my very dear friend the other day. There's a couple of people I would love to interview. I mean, my number one is like Bernard Arnault. Bernard Arnault is like my all-time hero. He will never do it, so we can just safely move on from that one. One. Two, I would love, love, love to have Peter Thiel on the show. This is, you know, the man who inspired my first love of venture. Before, it's been challenging, because he had involvement in politics. And so, we shall try again. And, we- I will email people 50 times, I'm on my 52nd email to Sasha at Windows- or, not Windows-
Michael Eisenberg
Microsoft.
Harry Stebbings
And, I will keep going. Persistence is everything, everything.
Michael Eisenberg
Well, you can just turn up at his door with your podcast equipment in Redmond. That'd be cool.
Harry Stebbings
I'm tempted to. You know, you could also create, you know, this is the other thing, which is like, people view a piece of content in isolation, which is so silly. So, we record this podcast today. This podcast is not a podcast, this podcast is a YouTube video. This is a series of YouTube shorts. This is 20 Instagram reels. This is our, you know, TikToks, we've spoken before, about at least 15 TikToks going here. We've got at least five Twitter threads going through this. We've got a Medium blog post. Every piece of content is 10 other pieces of content. I think it's something we've done very well at, from the beginning. And so, it's your question. Yeah, we should do that on Sasha and then we should document it. And, the story of getting Sasha on 20VC, the travel, the standing outside the Microsoft Office, the TikToks of our team ready and waiting with lights. That is how you tell a story. You have to engage people. And so-
Michael Eisenberg
I would love to be a fly on the wall at Redmond, for that one.
Harry Stebbings
Yeah, but this is my problem, also, Michael. Which is, like, we've lost creativity. We've lost so much creativity. I want the batshit crazy ideas of “Shall we paint our office black with 20VC logos all over it?”. Seriously! We have to-
Michael Eisenberg
So how about this? When you get to Tel Aviv, you and I are doing walking podcast on the beach of Tel Aviv, interviewing random founders. When you come here in the fall.
Harry Stebbings
Love it. But well, let's go further. What more can we like- I always ask myself-
Michael Eisenberg
In the water? What do you want?
Harry Stebbings
Maybe. Ray Dalio, just being our bit cameraman.
Michael Eisenberg
Wailing Wall?
Harry Stebbings
But like, everyone always goes like,” Oh, what a stupid thing to ask”. But, it's a very good one to push your mental thinking, which is, if Mr. Beast were running Aleph today, what would he do differently? Just ask yourself that. And yet, why-
Michael Eisenberg
We literally have an off-site on that, next week.
Harry Stebbings
Yeah. And, it will make you think, you know, he would probably give $10,000 to 10 entrepreneurs, and then film them for the next week, and see which ones go the furthest. Actually, $100,000 for a venture firm is nothing. It could be the first preeminent steps in how to do customer discovery, how to do product testing. It could be an amazing series.
Michael Eisenberg
So if in 2014-15 1415, like, the podcast was the next big thing in media, what's it in 2023?
Harry Stebbings
The rate of copycats in content has never been greater. You know, we started, very prominently, with the kind of, TikTok-style interview clips. They've been taken, totally, by everyone. And, ours are still massive and very, very successful. But, they've been commoditized. So, the commoditization of content type and style is very rapid today. What's the next? I think is, maybe, worrying me, creative extremes. Which is, like, bluntly, Mr. Beast style. Give away an island. How do we, you know, blow up a building in, you know, I don't know, whatever, whatever, whatever, whatever. Like, some crazy thing that he's going to do in the middle of a desert. Whatever crazy thing Mr. Beast does. I think creative extremes is very, very much where we're probably gonna go. It's pretty capital-intensive, so I don't know how that will play out. I think a lot of people look at the All In podcast and say, “Ah, are we going to go to the kind of, panel-style discussions?”. No. All In podcast is actually fantastic for the chemistry that they have together. It doesn't really work if you don't have that chemistry. And, by the way, Jason is an incredible moderator. Yeah. And I don't think he gets enough credit for that.
Michael Eisenberg
And, a great dinner guest, by the way, he's very fun.
Harry Stebbings
Sadly, I haven't had dinner with him yet. But so, I think, honestly, kind of, creative extremes. And then specialization. Really, really focused. Like, you know, consumer retail in Tel Aviv, will be podcasted. And so, I think you'll get hyper, hyper-focused, and then creative extremes.
Michael Eisenberg
By the way, that question was asked by Oren Charnoff. The next question is, what, from Yael, and a couple of others. What's the problem you most want to fix in the world?
Harry Stebbings
Multiple Sclerosis.
Michael Eisenberg
Because of your mom.
Harry Stebbings
Yeah. Mom's got MS. I'm also very frustrated, in many ways. You know, we were always told for years that diet didn't impact her MS. Well, she used to have about eight relapses a year when she was drinking, and then my mother actually stopped drinking. And, she's had one relapse in 18 months. Eight in 12 months to one in 18 months. The correlation there is the only thing that changes is drinking. So, I find that very, very frustrating. And, I think there's mis incentives within healthcare. Healthcare is completely free. Like, the whole world, Michael, is broken now, I think, very, very significantly. Not more than ever, because it's been, we've been through tough times. Yeah. But, it's significantly challenged across healthcare, across education, across climate. And, I think, this is why, it's never been a more exciting time to be a venture investor.
Michael Eisenberg
Will you invest in healthcare?
Harry Stebbings
Do I invest in health care? Absolutely. Yeah. I do. But also, you know, this is the funny thing. My first ever deal was in healthcare. Okay? And, it was an okay deal. Like, okay. But, not great by any means. The hardest thing as a venture master, and you'll agree with me on this one, I'm sure, is mental plasticity. Is making sure that, on the next healthcare deal, you come with a fresh mind, untarnished by the fact that, yes, you might have just lost money on a healthcare deal. But, the next one could be great. I really believe that, especially in early stage, you know, optimists make money. And, cynics are right. And, you really have to keep a fresh Canvas for every opportunity. And so, yeah, I think that would be very much front and center for me. I'm very passionate about MS. I'm also very passionate about male eating disorders.
Michael Eisenberg
Male eating disorders? What's a male eating disorder?
Harry Stebbings
Well, like bulimia that young men suffer from, or like, anorexia that young men suffer from.
Michael Eisenberg
I thought that was a female thing to be perfectly honest, I'm glad you've made me aware.
Harry Stebbings
So no men, sadly, get eating disorders too, but bluntly, they don't get any, or much attention, at all. It's massively on the rise. The kind of, glorification or idealization of these Instagram trainers causes men to just be bulimic, anorexic. It's a terrible, terrible pandemic, eating disorders, right now. Eating disorders is one of the most undiscussed and worrying themes, I think, in Western society today.
Michael Eisenberg
Tell me, how do you relax? Do you relax?
Harry Stebbings
I mean, I run to relax, I find that very relaxing. I listen to David Goggins when I run, and he tells me that I'm pathetic. Oh, my God, David Goggins, and he has his line “Who's going to carry the boats?”. And, every time, I will send the video to my brother of myself running, and I will literally be screaming, “Who's going to carry the boats”. And, the kind of takeaway from that, is you are the one who's going to carry the boats, you’ve got to take responsibility. And, you've got to be strong enough, when called upon, to carry the boats. It's like, you know, he says, training is building calluses on your mind. You have to be ready for the day when you are called.
Michael Eisenberg
Interesting.
Harry Stebbings
And, that changes a lot about how I think.
Michael Eisenberg
Do you take vacation?
Harry Stebbings
I'm taking my first vacation ever, with my girlfriend and an LP of mine, one of my biggest LPs, to their, kind of, holiday home. And I'm doing that in July. Otherwise, no, I don't.
Michael Eisenberg
Is that in Europe?
Harry Stebbings
It's in Europe, it's in France. The answer on like holidays is like, I think holidays are for people who know who they are in many ways. I have been so wrapped up in 20VC, for the last eight years, when you remove yourself from work, and you've only done what for your whole adult life, and never went traveling, never even went to university, really. I am 20VC. I know we should separate identities, there's zero separation. But, when you do then go on holiday, you have this real question of “Whoa, who am I?”. And, there's a very uncomfortable moment of staring into the abyss and realizing that actually, you don’t know.
Michael Eisenberg
Can you find out in France?
Harry Stebbings
You might find out in France. I think the honest truth is, I actually know now. Which has been a recent revelation, over the last year or so, giving up drinking. You know, finding someone special. Knowing that it's not money, I thought it was money, often. It's not. I love the park and an espresso, it’s five bucks. And so, I have a lot more grounding on that now, but I didn't before. And so, yes, I will take this vacation. But, it will be my first.
Michael Eisenberg
And, are you going to really turn off?
Harry Stebbings
It's only for a week. And, no, I will not turn off. But, I've also naturally done quite a lot of studies into the time it takes to turn off on a vacation. And, scientific studies suggest that it takes about 13 to 14 days before you will properly turn off. And so, I'm actually, then, rationalizing this or saying, “Well, if it takes 13 to 14 days, I scientifically should not turn off at all”.
Michael Eisenberg
You know what you need, by the way? You need the Sabbath, when we turn off, entirely, for one day a week. No phones, no connectivity. It'd be helpful.
Harry Stebbings
Do you know, actually, I've always looked at the Sabbath as this incredible time of purity? I love family. I'm a real family man. I love family dinners. There's nothing that makes me happier. And, I think it's one of the most wonderful occasions of purity and love that I would wish we had. But, we don't have it. And, it's very hard to instill in a non-Jewish home, I think, in terms of the discipline you have around the timing of people being there. And so, I would love it. But sadly, it's quite difficult to implement.
Michael Eisenberg
Do you- kind of, this exploration that you're on for “who's Harry”. How does that tie into settling down, having a family? You mentioned earlier, you didn't want to drink so that you would be awake to take your kids to the park in the morning. It sounds like that's starting to be part of the “Who is Harry” more than 20VC. There's, you know, Harry, the family man, both your current family and maybe future family.
Harry Stebbings
Yeah, I mean, I definitely think about that. I think, you know, if I'm being very direct and honest, I think the only way you truly grow up is by having children. And, that's not throwing shade at people who don't have children. And, it's not being disrespectful. But, I think having children forces you to realize that, actually, you are not the most important person in the world. When you're married, you can still go to the gym whenever you want, actually. You can still go and hang out with your friends, they will be fine on their own. When you are a parent, you cannot, they will fall off the chair, they will not be okay. You have to devote yourself to someone else, entirely. I think that's one of the most magical experiences that you can have. Now, don't get me wrong, they shit on you a lot. They throw up on you a lot.
Michael Eisenberg
Those are the least of the issues, trust me.
Harry Stebbings
There’s a whole lot of stuff that happens, I am not naive about that. And so, I think there's that. But I do think, you know, bluntly, whatever day you have ahead of you going into your child's carriage, and picking them up and hugging them, would be a very, very wonderful feeling. And so, yeah, I think about it a lot. I would like to be a young father. I think being a young parent is a wonderful thing. And, I do think about that. And, you know, I always say, people say to me, “What's the vision with 20VC? What's the vision?”. I say it's very simple. I want to be a 75-year-old grandfather with my grandchildren running around my armchair. And, I want to say, “Hey, let's look at you know, Wix, or let's look at X Company Y Company. And, you know, our family was a tiny part of that journey. And, I remember meeting Michael, when he was starting in, you know, one room in Tel Aviv”, and your grandchildren go, “Wow, that's amazing”.
Michael Eisenberg
Oh, Harry, I’ve got bad news for you, by the way.
Harry Stebbings
What?
Michael Eisenberg
My kids don't read any of my books, and I've written a bunch of them. And, they don't listen to any of my podcasts. Maybe one child listens to my podcast. And, maybe one or two are interested in my investments. And, I have grandchildren already. And I'm not sure they have any interest in what Papa is recording or talking about. So, you know, my prayer for you is that it works out for you the way you're hoping, but, even if it doesn't, there's a lot of wonderfulness in having children and grandchildren at a young age.
Harry Stebbings
Do you know what? I think I might be being rather hopeful here. I'm hoping I might just play it in the kitchen, enough. My brother will sometimes put on Sonoff, just like, “Welcome to 20VC”. And so, yes, maybe I am being hopeful, but I think that's very important. But, I also, like, yeah, I think that more and more now actually.
Michael Eisenberg
All right. I'm going to turn the rapid fire on you, quickly, to wrap up. If you were going to write a book, what would it be about?
Harry Stebbings
Mental discipline.
Michael Eisenberg
I like that.
Harry Stebbings
Most people are not mentally disciplined. They like to be told that it's okay that you didn't win. With children today, they’re told it’s, you get a participation medal. No, you didn't win, you should do it again.
Michael Eisenberg
There's a lot of softness out there that I don't think has done us well, as humanity. And everything's okay.
Harry Stebbings
It's not okay to, like, not win if you wanted to win. Like, that's the point. And so, I think like, I'm actually like- everyone says to me, “Oh, how do you do the work? How do you not burn out? How do you fast? How do you run 30 miles?”. Because I'm never going to ring the bell!
Michael Eisenberg
Yeah, I think, by the way, the best venture capitalists have a lot of self-motivation and self-discipline to, kind of, stay on things, and stay with things. A stick-to-it-iveness that you don't find all over the place for what it’s worth.
Harry Stebbings
Peter Fenton told me, very early on, that the best investors in the world have two things. They are hyper-curious, and they're hyper-competitive. And, the minute you lose one of them-
Michael Eisenberg
Time to get out. Yeah. So, what makes you, kind of, vulnerable and human?
Harry Stebbings
Did I not come across as vulnerable and human?
Michael Eisenberg
But, what causes that? What causes you, at any given time, to be vulnerable and human?
Harry Stebbings
I think it's, actually, a real luxury to have the ability to be vulnerable. And, what I mean by that is, I mean, you can sit here and pine on this show about being vulnerable about, you know, the problems that we have, and we face. It's very difficult if you haven't, to some extent, been a little bit successful, already. And so, firstly, I appreciate that it's a luxury that comes with a little bit of success. And, what causes me to do it? A real desire for more. For more people to do it, more people to say, you know what? I had this problem, and I learned this. And, it changed me in this way. It's not weak. I'm not weaker, because I had an alcohol problem. I'm stronger. Like, can't come in the ring with me, now.
Michael Eisenberg
Which brings me to, like, the last question, which is asked by Daniel Eck, the CEO of Spotify. Which is, what's the most significant hurdle you've had to overcome, so far? And, what did you learn about yourself in the process?
Harry Stebbings
Daniel always asks a very good question, huh? I mean, there are many, by the way. I think one of the lessons when I look at all of my hurdles, is that, in life, you are faced with continuous hurdles. And, there are two types of people. Ones that say, this was really, really hard. And, you know, it's okay. And, not many people come back from this, or not many people get over this. And then, there’s the other people that say, this is not going to be me, no way. If you actually just look at mine, you know, I was bulimia when I was 16,17, which is quite a serious eating disorder. And then, I went to a different school. Never really had friends throughout the schooling period. And then, I went to a different school, because I also didn't do very well at that old school, like I failed in my exams. They're not like B's, like failed. This is the other thing, everyone knows that they're entrepreneurs, and you put “whiz kid” in it. Yeah, you look at it now, every story is crafted by great, you know, publications and marketers, and the Colossians with books in the background of every video conference they do. It's a beautiful craft. And so, when I look back, bluntly, the lesson that I have is, you will continuously be faced with failure and shit. And, you have a choice of do you accept it? Or do you decide that only you decide the next steps? And, only you can tell yourself that you're not good enough. Every step of the way, Michael, I was told that I wasn't good enough. Every step. There's no way you can be a VC. You're a kid. You're a podcaster. Now, they’re desperate to come on the show, every week. Point being, only you tell yourself you're not good enough. And, even then, I think people underestimate themselves.
Michael Eisenberg
Was there a turning point that you developed that self-confidence? You said, “I'm gonna beat this”.
Harry Stebbings
Yeah.
Michael Eisenberg
When you learned that about yourself. What was it?
Harry Stebbings
Well, you want the honest, honest truth, naming names? I got down to the final two, or whatever it was, of associated an analyst position at Excel in London, when I was 18. And, the partnership, kind of, was split. Half decided that I was great, and half decided that I was too young and I wasn't ready. I remember getting a call, on a Friday afternoon, I was in the middle of London, and I was ready, you know. And, this is, like, a career-defining call sitting, on the bench by the Tower of London, outside of Pret, with my lunch. And I'm like, “I'm ready for the news”. And then they're like, “You are too young”. And you're like, in that moment, your dreams are crushed. And, it's like the Steve Martin quote, which is, like, “Be so good, they can't ignore you”. And, the truth is, they were probably right, I was too young. And, by the way, I would have stopped doing the show and joined as an analyst and an associate. It would not have been the right thing. In hindsight, I'm very grateful. But, in the time, it taught me that nothing felt as bad as that moment, when I was told “absolutely not” to my dream, by someone who I really respected. And, I will build such a big business, that you will regret it.
Michael Eisenberg
Where did you find that? That, “I'm gonna to make you regret this, that I'm good enough, I can do this”. Where do you find that? That I can lose the weight. I'm going to be in venture capital, and I'm going to build a media. But, where did you find that?
Harry Stebbings
I think that anyone can do anything if they work hard enough. I really do. There are some physical constraints. Sadly, you know, I'm not going to be in the NBA. I'm not tall enough. You know, some people don't have the bone density for being a great swimmer. Sure. But, generally, I am not- I think more and more people need to understand that they are capable of so much more. And, actually, with hours, and with strategy and craft, you can do more than you think. And, I just always believed that.
Michael Eisenberg
I'm a deep believer in that too. And, I think, you know, one of the things you've led the way on Harry, candidly, is exactly this. Is to empower millions and millions of people to believe that they can touch this thing called “entrepreneurship” called “venture capital”. And, in a world where entrepreneurs are so critical, and, in a world where it's gonna get harder to earn, kind of, a white-collar income, your empowerment of other people candidly, is inspiring.
Harry Stebbings
Michael, you know, you touched on 20 Sales. This is eight incredible women, who are the best, best go-to-market experts in the world. They are freaking amazing. I want them on every cap table. And, to be very clear, I have no carry in their funds. They are the GPs, they have all the carry. So, just to be clear on that. But they are exceptional people. And, they deserve a fund with great LPs. And, they deserve the chance to also invest. I am so proud that they let me help them in that way. And, I look at my mother, and, you know, bluntly, my mother wasn't afforded chances that she should have got, and if I can be a tiny vehicle of change in some of those cases, fuck, I'm gonna take it.
Michael Eisenberg
You know, that's amazing inspiration. You know, my own Genesis story is that I had an interaction with a rabbi, when I was 19 years old, who told me that if I moved to Israel and enabled 10,000 other people to earn an honest and decent living, it would be an incredible Mitzvah, you know, religious commandment and life mission. And so, everything you say really resonates. I just want to tell you, personally, and I should also make a full disclosure, I'm a tiny LP in Harry’s fund. But, you're just an inspiration for a lot of people. So, thank you for being you and being so raw, and so vulnerable. And, so present with us here, and just keep up the amazing work, Harry.
Harry Stebbings
If people don't know, that you've been an amazing advisor to me in the tough times. I call you when times are tough, and I really appreciate our friendship. And so, thank you for always being there for me and I've been uncomfortable but also loved having the tables turned.
Michael Eisenberg
Well, I appreciate you doing it Harry. Thanks so much, and, you know, see you in Tel Aviv or London, soon.
Harry Stebbings
I will see you soon.
Executive Producer: Erica Marom
Producer: Andrew Jacobson and Sofi Levak
Video and Editing: Ron Baranov
Music, Art Direction and Invested Logo: Uri Ar
Design: Rony Karadi
