20VC: Raising $400M for 20VC: Fundraising Lessons | Getting Marc Benioff Through 53 Cold Emails: How to Master Cold Outbound | 7 Lessons from 101 Decacorn Founders with Harry Stebbings (Simon Squibb Edition)

AGENDA: 00:03:00 – Harry's Wild Start: Making £1.75M at 19 in 36 Hours 00:06:00 – How Harry Got Marc Benioff on 20VC with Cold Emailing Alone 00:07:30 – Raising $70M on WhatsApp – Relationship Building Secrets 00:12:00 – Decision Framework: What Would Pat Grady (Sequoia) Do? 00:15:00 – Chase Your First Million – It Unlocks Everything 00:16:30 – Advice for 19-Year-Olds Today: Niche Down, Interview Leaders, Publish 00:18:00 – University Is a Waste for Most | Leverage Youth & Risk 00:22:30 – How Getting Kicked Out of School Changed Everything 00:30:00 – Why Should Everyone Be Creating Content Today and How to Start 00:35:30 – 7 Lessons from Billionaires 00:36:00 – #1: Never Accept No (The $12M Turnaround Story) 00:37:30 – #2: Beat Down the Door (53 Emails to Marc Benioff) 00:39:00 – #3: Just Start – 99% Never Do 00:40:30 – #4: Use a Role Model Framework for Hard Decisions 00:42:00 – #5: Chasing Money Won't Make You Happy – Enjoy the Art 00:44:00 – #6: Break Big Visions into Achievable Milestones 00:45:30 – #7: Win Over the Partner (Power of Pillow Talk)

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Harry Stebbings?

  This is 20 VC with me, Harry Stebbings. Now, I'm very often asked to reveal a little bit about my story, and I'm always quite reserved in doing so. I think you have to really return a lot of money to investors before you think you're worthy of being interviewed. And I think too many young VCs are too out there when they haven't made a lot of money for investors. And then I get a lot of people say, we want to hear more about you, we want to hear your story. And so I did a show with Simon Squibb, a brilliant entrepreneur in the UK. My mother said that she loved the show and that she thought that it should be heard by our community and our fans. And so today we release a very special one where Simon interviews me. You hear a little bit behind the scenes of 20 VC, the fundraising strategy for a $400 million

• 0:43Harry Stebbings?

  fund, how I got Marc Benioff to come on 20 VC through 53 cold emails, and many, many more cool stories. But before we dive into the show today, this episode is brought to you by Perk, the intelligent platform for travel and spend. Every successful founder remembers their breakthroughs, those moments in the journey that changed their trajectory, whether it was going from burning cash to building leverage, or from headcount growth to operational scale. Breakthroughs don't come from spending hours buried in spreadsheets, booking and rebooking travel, or chasing their teams for last quarter's coffee receipts. That's shadow work, and that's what Perk was built for. One recent study found shadow work costs companies over 1.7 trillion every year, as employees waste hour

• 1:25Harry Stebbings?

  after hour on manual, time-consuming work, instead of the jobs they were hired to do. Perk's AI is purpose-built to automate shadow work, so teams can focus on real work with real impact. Don't let anything get in the way of your next breakthrough. Leave the travel and spend to Perk. Visit perk.com/20vc today. Perk, powering real work. Just as Perk rewards your professional milestones, Daily Body Coach helps you celebrate and sustain your personal wellness wins. You know how so many founders and execs say they'll finally take care of their health once things slow down? Well, they never do. Running a business is a marathon made of high-intensity sprints, and taking care of yourself is what gets you through

• 2:10Harry Stebbings?

  Those times performing at your best, both professionally and personally. This is exactly where Daily Body Coach comes in. Daily Body Coach is a complete, high-touch service for busy founders and executives, combining personalised nutrition and training with psychology-based coaching to help you not just follow a plan, but actually build the systems, habits and mindset to stay at the top of your game. Built by an exited founder and led by certified experts with masters and PhD-level credentials, Daily Body Coach is fully tailored to your life. Whether you're travelling, dining out, or in back-to-back meetings, you get daily accountability, data-driven insights from DEXA scans, and blood work and a highly certified team backing you.

• 2:53Harry Stebbings?

  If you're serious about performing at your best, physically and mentally, go to dailybodycoach.com/20vc. That's dailybodycoach.com/20vc and take the next step. While Daily Body Coach helps you build healthier habits, Air Wallets helps you get paid globally without the headache. Founders, let's get real about the growth tax. You've raised VC funding and you're scaling globally and it's no longer about shipping product, it's about orchestrating operations across continents. But suddenly, your payments and finance stack is choking your growth. You're logging into lots of different banking portals, waiting days for transfers and wasting hundreds of hours on manual reconciliation and reporting across entities. It's operational drag and it's at your scale.

• 3:38Harry Stebbings?

  It's costing millions. That's why I'm so excited to partner with Air Wallets. Air Wallets are more than just a banking alternative to HSBC or Citi. Air Wallets brings you an intelligent financial operating system that powers how global businesses operate and grow, allowing you to manage and automate banking, treasury, payments and spend. The most exciting part for me, they're heavily investing in agentic finance. If you're scaling globally, you need a banking and finance platform that's borderless, real-time and intelligent. Check out Air Wallets today and see how they're helping thousands of businesses like Canva, McLaren and Deal. Scale at airwallets.com/20vc. Terms and conditions apply. Your monies are safeguarded, not FSCS protected. See airwallets.com for more details.

• 4:27Speaker 01

  Harry, thanks for being here. Off camera, we were just talking about like, you're 19 years old, you made in a million and a half pounds. Can you talk a little bit about that quickly before we get into all the lessons you're going to teach us today?

• 4:37Harry Stebbings?

  Yeah, I mean, I very clearly remember my mother telling me that she had MS and she'd had MS for about five years before, but that the MS medication was like $750,000. And I had this, you know, useless podcast at the time, which had no listeners, and we can get to the importance of persistence, no listeners. And I thought, gosh, how do I leverage this to make money to pay $750,000 when I made no dollars? And I went up to my bedroom, I emailed 25 of the biggest CEOs in technology, and I said that their biggest competitors wanted to sponsor the podcast, but I was a fan of their product instead. Would they like to take it? I priced it at $95,000 each, just under the 100 grand procurement budget, and I got 19 of them say yes, they would love to. And that was $1.75 million in 24 hours.

• 5:21Speaker 01

  That's unbelievable and a great lesson about frankly, creating FOMO and sales. See, I think sales should be taught in schools. I think sales, like anything, is just a process. It's totally teachable.

• 5:34Harry Stebbings?

  School misses the two most important things, which is sales and public speaking. Totally agree with you. And also personality. Everyone wants to work with someone who they like. And so at the end of every single email, I'd put, PS, I know that McKellen 75 is your favorite whiskey. I'd love to have one with you when you're next in London. The minute that you add that, you literally treble your chances of getting a response.

• 5:56Speaker 01

  It's effort, isn't it?

• 5:57Harry Stebbings?

  Just a little bit of it.

• 5:59Speaker 01

  The people I've hired that have messaged me on things like LinkedIn have actually understood what I'm trying to do and then brought some value in the actual message they send me. So they're not just like, hi, someone I'd like to work with you because I can learn a load, which is great, but also that's just taking from me. It's such an important lesson in sales, isn't it? The detail, the attention to detail and everything is important.

• 6:19Harry Stebbings?

  And so few do it. If you want to win, be a purple cow.

• 6:23Speaker 01

  Yeah, of course, I love that whole thing.

• 6:24Harry Stebbings?

  Just be different. It is so important.

• 6:27Speaker 01

  So you have interviewed, is it 107 billionaires?

• 6:30Harry Stebbings?

  Yeah, yeah.

• 6:31Speaker 01

  Yeah, so first of all, how did you manage to get a hundred and seven billionaires? Is it a similar thing, just persistence?

• 6:38Harry Stebbings?

  Cold emailing, doing good cold emails is a real art. They need to be short, they need to be concise, they need to have a clear ask and they need to be personal. And then you use social validity as your weapon, which is, I just interviewed Richard Branson and I would love to have you on the show. Who is not wanting to be tied to the brand of Richard Branson in the same caliber? Very few entrepreneurs. It's like, okay. And so I use social validity as a weapon to encourage people that it was a good and strong environment that they wanted to be associated with.

• 7:07Speaker 01

  I love that. But it does make a big difference, right? I say, I had the same thing. When I started Fluid, I rang up a company, I started this agency, no one knew it. And I said, hi, I'm Fluid, I'd love to work with you. And they said, no, sorry, we're busy. So I ran back and said, hi, I'm working with CNN and I would love to work with you. And they went, oh, you're working with CNN? Sure, okay, come on in. So you just have to use that social proof.

• 7:26Harry Stebbings?

  A hundred percent.

• 7:27Speaker 01

  It's leverage. Some people don't like sales because they think it means sneaky. Don't have to be sneaky about it. I think car salesman kind of vibes is what people think sometimes.

• 7:34Harry Stebbings?

  But at the end of every show, I would say to people, hey, who are three people that you think I should have on that would be fantastic? And the minute people commit to three more names, I would say, hey, if I send you an email that you can forward on to them, would you mind making the intro? When people commit to the three names, they're committed to making that intro. And so I create, you always want to create flywheels in any business where one leads to more success. And so with every show, I got three more intros.

• 8:00Speaker 01

  Now, you said earlier something else off camera, I want people to know this, you raised seventy million on WhatsApp.

• 8:06Harry Stebbings?

  Yeah.

• 8:07Speaker 01

  So, I mean, tell me a little bit about that. I mean, people might hear that and say, oh, just WhatsApp, that's, how did you do that? I think I know, but you share how you did it.

• 8:14Harry Stebbings?

  I mean, you know, when we fundraised, we raised from very rich individuals and we raised from institutions. And I would, in between sets in the gym, walk around in my two-minute breaks and I would message individuals, this was, and say, hey, I'm going out to raise the new fund and I'd love to have you in. And they would come back with, you know, count me in for a million or count me in for two million. What people don't see is the ten years of relationship building before that. But the most important lesson from that, actually, is I always want people off email, get people off email. People want to work with people who they like. And so at the end of calls meetings, I always say, Simon, I'm terrible at email. Let's jump to WhatsApp.

• 8:51Speaker 01

  Yeah.

• 8:52Harry Stebbings?

  And then at the weekend, when I'm walking with my mum, I'll send a photo of me and mum eating a doughnut. And I'll say, God, loved our meeting this week. Next time, you've got to join us on our walk. People resonate with people. And so I build those relationships on WhatsApp unlike anyone else.

• 9:07Speaker 01

  Well, I think I've been building a relationship with you for thirteen years. So we actually first met, people might not even know, my audience is quite young. You know, they might have no Periscope. Right. I remember thirteen years ago, I was hiking in Hong Kong. Periscope was one of the, was the first live product. And I was live in Hong Kong and you came on my Periscope. And you stood out instantly. You were, oh, I love this Simon, you know, I'm, I'm launching a podcast. I'd love to have you on. And I feel like for thirteen years, I've been following you ever since and your rise and what you've done has been an inspiration. Do you remember that?

• 9:38Harry Stebbings?

  I, I do, I do actually. But I mean, wow, it takes me back. I remember Periscope and Meerkat were the two live streaming products at the time. And so I absolutely do remember that. I was so embarrassing in how I did so many things back then. I was so effusive with, you're the greatest entrepreneur I've ever met and da, da, da.

• 9:55Speaker 01

  You didn't say that to me, I don't remember that, to be honest.

• 9:58Harry Stebbings?

  But the point of that is like, people look at the successful people today and think I could never be that. It took years of hard work to get there. And actually you have to go through prolonged periods of not being very good before you get to a stage. And that's why people don't start. And so what I say is just take the first step and you're better than ninety nine percent of people. It's like going to the gym. No one goes to the gym and it's like treadmill. I love you, old friend. It's uncomfortable, it's hard, but by showing up every day, you get better and better.

• 10:27Speaker 01

  Hmm. People listening to this podcast might be like, well, you know, Harry's got a big following. Of course he's, you know, he can WhatsApp people and get money. But that's why I like your nineteen year old story, because you didn't have a big following then.

• 10:38Harry Stebbings?

  Did not have a big following at all. And I leveraged ego and insecurity of famous people and successful people to make money.

• 10:46Speaker 01

  And, and you did something, you didn't, you see, what I think of that case with the whole. Uh needing to support your mum part of it is it wasn't just you wanted success, you needed it. I think that's the only flip switch that people need to have. You didn't just want it, you didn't just want a million pounds for the sake of it, you needed it. So that's why it had to happen.

• 11:06Harry Stebbings?

  I I would also, can I just say, you should aggressively chase making your first million more than anything else. Because the hardest to make is your first million by far. And also the world makes richer people get richer. I see this now, I you know, I'm fortunate that I have, you know, the posh banks that look after our money. And I get higher interest rates, I get better investment products, I get access to things that most other people can't. Cause I have money, but it feels wrong, but the world is unfair and wrong. And so my advice would be like chase the first million because it unlocks so much more than you could anticipate.

• 11:42Speaker 01

  And that's why I think starting young is quite important. Because you can take more risk when you're young, which is why, you know, I know we're both on the same train of this like. University for ninety percent of people is a waste of time.

• 11:53Harry Stebbings?

  Totally.

• 11:53Speaker 01

  Four years of your life, forget the money you can waste at university. But those four years are the years you can you can sleep on a couch with friends, you can stay at home for a little bit longer, you know, like you can take risk, right?

• 12:04Harry Stebbings?

  You also have the endurance, like it is hard work being an entrepreneur and you will have to work insane hours. I notice this now, I mean, I'm not as old as you are, so I'm no, no.

• 12:15Speaker 01

  You're not though, so it's not on offense.

• 12:17Harry Stebbings?

  But I notice now my stamina at thirty is not what it was at twenty. Like take advantage of being young and being naive. But sorry, the biggest problem with the UK is that we are negative. Positive visualization is everything. I never doubted that this would work. And this sounds arrogant, but I always knew I would be successful. It never dawned on me that it wouldn't work. And when you visualize something, you make it happen much more likely, downside and upside. And I think the trouble with the UK is you say an idea and we go, oh, that's not gonna work, that's not gonna work. And in America, we say that's gonna work. We need much more positive visualization in the UK.

• 12:55Speaker 01

  How would you go about making that a reality in the UK? Do you think there's a fix?

• 13:00Harry Stebbings?

  Yeah, I do. It's why I started Project Europe, which is a ten million dollar fund, which gives two hundred grand to incredibly young people to do unreasonably ambitious things. We need more people to say yes to crazy dreams. And I think snootiness is another mega problem that we have in the UK, which is like, oh my gosh, why would you go from being a physicist at Cambridge to opening a bakery and like that's a bit beneath you. What happens if you open up the most successful bakery in London? You document it, you have amazing cues outside the corner, and then you become the next Cedric Grelle with bakeries in every city and every big country.

• 13:34Speaker 01

  You know, even you just do it for a year and you realise it wasn't for you, but at least you don't live with regret.

• 13:38Harry Stebbings?

  A hundred percent.

• 13:39Speaker 01

  At least you tried, right?

• 13:40Harry Stebbings?

  My biggest failures turned into my biggest successes. Getting kicked out of boarding school for being bulimic led to my entire life. I would never have started the media company if I hadn't been kicked out of boarding school. Just like, think about that. I would have been a mid-lawyer.

• 13:56Speaker 01

  Bad luck turns into good luck over time if you leverage it right.

• 13:59Harry Stebbings?

  Yeah, and but that's where the individual comes in, which is like only you decide the next step. Make a positive decision. When shit happens, you can either accept it or you can progress and move on. I could have gone fucking bulimic, I don't have a passion.

• 14:15Speaker 01

  Woe is you. You could have taken it as a, you know, as a reason to not go for it.

• 14:20Harry Stebbings?

  A hundred percent. You decide the next step.

• 14:21Speaker 01

  What do you think that that thing is where you take it and make it positive? And and and some people take it and make it negative. What what is it you think that made you? Was it, for example, supporting your mum? Was it an external factor, you think? What was it?

• 14:32Harry Stebbings?

  I I I think it was twofold. I think it was one, having a mentor that could actually redirect me in the right way. And I think it's two, the ability to end the day. And what I mean by the ability to end the day is like, when you have a shit day, go to bed knowing, my mother always quoted Scarlett O'Hara from Gone with the Wind, which is tomorrow is another day. Do not let the prior day impact the next day. Always come at it with a fresh mind. I think the woe is me, one day will lead to another series of bad days, is very dangerous. And for me that I always think of is like, if you have the ability to be miserable for no reason, you also have the ability to be excited and optimistic for no reason. Embrace it.

• 15:16Speaker 01

  Yeah, I love that. The nineteen year old you idea there, just wanna pick that, pick at that for a second. Because I, what I'm tending to do when I give young people advice now is always talk about media. It's partly because I'm in media, but also, you know, I joined TikTok when I'm forty five years old. All of my peers laughed at me. When I was on TikTok, I was around a table of other people that sold their businesses. They were buying property and doing these things. I'm like, I'm going on TikTok and sharing knowledge and they laughed at me. Now those same people ask me how to get TikTok for their businesses working. But what I'm getting to is like, young people can't afford a house. It's too expensive. But social media, you can make one video today and get ten million views and sell a product and make money. Like, it's the most amazing, incredible thing. I had to knock on doors when I started a business, literally. But you mentioned media is what you do straight away.

• 16:01Speaker 01

  And I, I think it's important just to pick at it for a second because a lot of people will be listening like, well, I don't know how to interview. You weren't a great interviewer at the beginning, right?

• 16:08Harry Stebbings?

  I was, I was eighteen, I spent fifty dollars and I bought a microphone on Amazon, an ice ball microphone. That's what it's called. And I was a terrible interviewer. Point being, you only get good by repeatedly doing it. And it took me three years before I probably got good. It took me four years before I got a thousand plays. Simon, you've been building this media empire now.

• 16:31Speaker 01

  Six years. First three years, nothing. I got no.

• 16:33Harry Stebbings?

  Oh, wow. Okay. Yeah. So most people give up. This is a game of who can survive the longest. And the lovely thing about content, Simon, if you fail, it's because no one cares. And if no one cares, no one will know that you failed. So why don't you do it anyway?

• 16:48Speaker 01

  That's a great framework for people to go and apply for their lives. Yeah. And the truth is, no one gives a shit anyway. They will laugh at you until they're no longer laughing and then they'll be asking if they come on your podcast.

• 16:56Harry Stebbings?

  A hundred percent.

• 16:57Speaker 01

  It's like, I used to think technology was going to be the barrier to entry to building businesses. I think now it's the ability to communicate, like you said, the ability to sell, and frankly, marketing.

• 17:07Harry Stebbings?

  It's distribution.

• 17:08Speaker 01

  Totally.

• 17:09Harry Stebbings?

  Distribution is.

• 17:09Speaker 01

  So if you can build distribution, and everybody can. It's kind of a commodity product. You can, anyone can jump on their phone and start creating.

• 17:16Harry Stebbings?

  Well, this is why our venture funds are doing so well right now, which is because everyone has a venture capital fund today sadly, but not everyone has distribution. You know, I posted about one of our companies, Fixer, which is email autocomplete, and they're going to hate me for that, but it does your emails better than any other AI can do. I posted about them on LinkedIn and they got four million in revenue from one LinkedIn post.

• 17:38Speaker 01

  Crazy.

• 17:38Harry Stebbings?

  For an investor to bring you four million from one post.

• 17:41Speaker 01

  Especially as most investors say they're going to bring you value and they give you a bit of advice.

• 17:44Harry Stebbings?

  Yeah.

• 17:44Speaker 01

  You know, actual value.

• 17:46Harry Stebbings?

  That's actual value and we have data to prove it very valuable. And so you're moving to a world where distribution is the biggest determinant of value. So I completely agree.

• 17:55Speaker 01

  Sponsorship deals, we were again talking a little bit off camera about this. I have a feeling that, you know, you look at things like Facebook, it did such a great job of becoming a valuable company because it had all the attention. And then on top, apps came, you know, like Snapchat and Instagram. And then again, they draw all the attention. I think the next big platform is a creator. Because, because again, like, why would you promote someone else's brand if you can promote a brand you own? So for example, I'm launching a competitor to Starbucks as part of my business model.

• 18:23Harry Stebbings?

  Starbucks?

• 18:24Speaker 01

  Why would I, why would I promote Starbucks, which I don't particularly believe in? They might have the money to sponsor me. I don't, they're not paying tax in the UK. In my opinion, the product is no longer good. Why wouldn't I start my own competitor to it?

• 18:35Harry Stebbings?

  Completely agree with you.

• 18:36Speaker 01

  It doesn't make sense to just take a small fee off them and then promote them and they get the every month revenue from my marketing, right?

• 18:42Harry Stebbings?

  Completely agree. I think people are companies today and that's the big transition. Cristiano Ronaldo, CR7, is a brand as big as Starbucks or Coca-Cola or you name it. He is a company, he's not a person anymore. And there is a stage where you get to where absolutely that is the case. And I think you saw it with Mr. Beast, where Mr. Beast started doing his own products. Now I think you've got to be careful about the products that you choose. You know, Mr. Beast did Mr. Beast Burgers. Bad, and he'll say this himself, bad product to choose, difficult to monitor quality, difficult time, delivery.

• 19:15Speaker 01

  Clever scale mechanism because he worked with outside partners, but I mean, quality control was a problem.

• 19:19Harry Stebbings?

  Exactly. And so I think you've got to choose your product well, but I 100% agree. There comes a scale where it doesn't make sense to promote someone else's if you can promote your own.

• 19:29Speaker 01

  So let's quickly, just very quickly, run through the seven things that billionaires have taught you. So number one, just say it a sentence if you like.

• 19:35Harry Stebbings?

  So lesson one is like never accept no for an answer. When I was fundraising, I got turned down by two people and I emailed them back. I said, I have missed $500 million of investments that would have returned $500 million because I thought the person was great, but I did not like the market that they were in. I fear you are making the same mistake right now. I will give you a call tomorrow morning and we can have a chat. I called both of them up the next morning and one invested five million and the other invested seven million. If you accept no, I would have not had 12 million there for the fund.

• 20:10Speaker 01

  Unbelievable. So true. Next lesson?

• 20:12Harry Stebbings?

  So important. Lesson number two, you have to continuously beat down the door. I emailed Marc Benioff from Salesforce 53 times.

• 20:22Speaker 01

  I heard about this.

• 20:22Harry Stebbings?

  Every single Sunday.

• 20:24Speaker 01

  Why didn't he block you?

• 20:25Harry Stebbings?

  I would have blocked me. And so I emailed him 53 times. Every time I put a new PS with a personalization. PS, I hope the weather in X is nice. I knew you had a holiday home there. PS, I hope that you're enjoying the Macallan 75. It's also my favorite. Every single time, I would do it again and again and again. It never stopped. And on the 53rd time, he responded and said he'd come on the show.

• 20:50Speaker 01

  Was that instantly, he just said, was the exact sentence? I'd love to know the exact reply. What was it? Yeah, or come on?

• 20:55Harry Stebbings?

  I think it was like, yeah, I'm in.

• 20:56Speaker 01

  Yeah, I'm in.

• 20:56Harry Stebbings?

  Yeah, I'm in. And that was kind of it. After 53.

• 20:59Speaker 01

  Right.

• 20:59Harry Stebbings?

  CCing my team.

• 21:01Speaker 01

  Do you know, sometimes people talk about this approach, like for example, if you found out who his personal trainer was and connected with his personal trainer, so his personal trainer would mention you to him in, like I was just listening to Harry on 20.

• 21:11Harry Stebbings?

  Very smart.

• 21:11Speaker 01

  Any other strategies like that you've seen on the sales side?

• 21:14Harry Stebbings?

  The one thing I would just say is that you always need to think about the next step in content. And so like when Marc Benioff says, I'm in after 53, do you know what I'm thinking? Fucking viral Twitter, which is I emailed Marc Benioff 53 times. This is the email that converted someone worth $100 billion to come on my podcast.

• 21:35Speaker 01

  That's great because that keeps you going doing it too, right? I've emailed him 100 times, he still hasn't replied. There's also content.

• 21:40Harry Stebbings?

  And then do you know what also? Everyone goes, oh, wow, Marc Benioff's going on Harry's show. Harry's getting legit guests these days. And then guess what? You can actually take it to the next Marc Benioff and be like, hey, look, I go viral with tweets like this and you get more social validity. Super important.

• 21:57Speaker 01

  Brilliant. Third thing?

• 21:58Harry Stebbings?

  So important. I was terrible when I started. I was not charismatic. I sucked at interviewing people, but ninety nine percent of people never ever start. I think the most important thing is just to take the first step. Like, activity drives outcomes. Most often, you don't actually know where it's gonna end up, but you will never find out if you don't start. Like, just start. Sell swimming trunks. You know what you're gonna learn? No one wants them, but everyone wants cool goggles. Huh. That's the lesson that we take. Just start and no one else. I find honestly, the biggest thing is like, it won't work, so I don't start.

• 22:38Speaker 01

  Yeah.

• 22:38Harry Stebbings?

  Ninety nine percent.

• 22:39Speaker 01

  We use that one human skill we have, the special skill that no other animal has, which is the ability to predict the future.

• 22:44Harry Stebbings?

  Mm-hmm.

• 22:45Speaker 01

  And we use it against ourselves to predict a failure.

• 22:47Harry Stebbings?

  A hundred percent.

• 22:48Speaker 01

  Mental, isn't it?

• 22:48Harry Stebbings?

  It's also like ninety nine percent of the worries that you have have never happened.

• 22:52Speaker 01

  Yeah, yeah. And the upside is actually far greater than you think. You can't actually predict what's gonna happen.

• 22:57Harry Stebbings?

  Way greater. I could never have expected my life to be all it is.

• 23:00Speaker 01

  A hundred percent, yeah.

• 23:01Harry Stebbings?

  Ever.

• 23:01Speaker 01

  I, I, I think at this particular point, just for a second, it really kind of blows my mind. When I first started doing the content, I was doing like how to raise money. And I was talking about how to find a co-founder. And the videos were doing okay on the views, you know, typical business content. It was doing average. And then I thought, right, go into the street and ask people, but why are they not actually doing it? And most of the time, they're not even giving themselves the time to think of something, you know? So that's why, what's your dream now, by the way, is pretty much like a standard saying, people, when they meet each other, ask each other now, though, what's their dream? In schools, kids are asking themselves, what's their dream? That starting point of getting people to actually start, that is the, that is the hardest thing. And once you've started, like, I was hire someone as quickly as I can when I start something now, so then I've got someone I'm countable to. Like, if I don't hire someone, I found, I'm a bit lazy,

• 23:46Speaker 01

  I don't have to do it, so I won't do it. You need to keep yourself accountable to.

• 23:49Harry Stebbings?

  A hundred percent.

• 23:50Speaker 01

  And so, Monday morning, I've got a member of staff saying, Simon, what are we doing this week? I'm like, okay, I've gotta go do it, you know, like.

• 23:54Harry Stebbings?

  Sometimes you have to burn the boats to encourage action. When I dropped out of university, I was a scholar at King's doing law. It was like quite a credible career path that I was on. Dude, I had to make it work. Like, there was no option. I'd burnt the boats, I'd left university. Shit, I was gonna have to go and work in a pub or be a waiter if I didn't make this podcast work.

• 24:17Speaker 01

  But I must have a big moment to leave, that decision to leave.

• 24:20Harry Stebbings?

  Yeah, it was. I remember very much, I got a call from a sponsor and they said, we wanna sponsor the show. And I said, how much is it? And I said, it's a hundred thousand dollars. And they were like, fantastic, send us over the paperwork. I didn't know what the paperwork meant.

• 24:38Speaker 01

  And there was no AI then, either.

• 24:40Harry Stebbings?

  But to our point on like the valueless nature of university, I just Googled contracts. And I built my own contract by Googling, and that's what I used for this hundred grand. But I went to my law professor and I said, how much do you earn a year? And he said eighty two thousand. And I thought, okay, well, that's my answer.

• 24:59Speaker 01

  There you go, yeah.

• 24:59Harry Stebbings?

  And so I called up my parents and I said, I'm leaving university and, you know, this is following my dream.

• 25:05Speaker 01

  You did another clever thing there that I want people to learn, which is like, you can mitigate the risk of starting by getting one customer. You can tell a customer what you're gonna do, and they can say, yes, they'll do it if they have the service. And then you know you've got a customer if you commit to doing it.

• 25:18Harry Stebbings?

  A hundred percent. You can be in a job and go to a customer and say, hey, I can completely revolutionize how you do hiring within your company using AI. And they're like, wow, we'd pay you thirty grand for that.

• 25:28Speaker 01

  Right.

• 25:29Harry Stebbings?

  Great, now you've got enough where you can leave. But that's also where it's helpful being young, because the cost is less before you have a family.

• 25:36Speaker 01

  A hundred percent, yeah.

• 25:37Harry Stebbings?

  Big one.

• 25:38Speaker 01

  So number four.

• 25:39Harry Stebbings?

  I think the biggest challenge is when you don't know what to do. And so I have one framework when I have tough decisions. Think of someone who you deeply respect and admire and you want their life. For me, it's Pat Grady at Sequoia. Three reasons, great father, great investor, great husband. And whenever I'm faced with a tough decision, I ask, what would Pat do in this case? And it generally always leads to me to make the right and honorable decision when I might have otherwise made a different decision.

• 26:10Speaker 01

  Got it. Number five.

• 26:12Harry Stebbings?

  I think a big problem that young people have today, what do you wanna be? Rich. I think money does make you happy, absolutely, but chasing money will not lead to money. I chased money for a few years when I was very young and it did not lead to happiness or outcomes even. When you enjoy the art of doing, the money is the output. And that's really important. I remember, to be fair, when I made my first million, you know, I was very lonely and I remember sitting on my balcony in Fulham where I lived and I was with a bottle of tequila and, you know, a packet of cigarettes and I thought I could buy any table in any club. The only challenge is, Simon, I don't have any friends

• 26:56Harry Stebbings?

  to bring to that table. And I looked at my bank balance, which had a million, and I was like, this doesn't feel like the Who Wants to be a Millionaire moment when the confetti's coming down and it's like this glorious. I was very unhappy at that moment. And it taught me something really important, actually, which is ask yourself a very simple question. What truly makes you happy in life? Like, truly makes you happy? For me, it's walking around High Park with my mother and getting an espresso. The espressos are two pounds eighty. So for a good five pounds sixty, you'll be good to go on your two espressos. That is my happiest moment. Period. So five pounds sixty is my happiness. Okay, that's good to know.

• 27:35Speaker 01

  I think that digging deep in you, what makes you happy is a really, really powerful point. I like building, you know, like I like having a mission. I also, the audience, I always think about the audience, listening to two people that have got money, that made money. A lot of my audience haven't made money yet, hearing, you know, that whole point about money. You've said two different points. One earlier about how money does bring happiness, which it totally does, completely agree, but how also money in itself is not enough, right?

• 28:00Harry Stebbings?

  Yeah, it's like, don't chase it.

• 28:02Speaker 01

  Don't chase it. And I think the nuance of this, again, I don't want anyone to miss this, is like. You've got to have a centre, right? So I see your posts about you going to see your mum. You'd always do it because you know that's your happy place. And so building a business isn't always happy. We're not always happy, right? But you've got to have that happy place. You've got to allocate time to the happy place.

• 28:21Harry Stebbings?

  You know what's so funny? I get people in my DMs be like angry about my mother posts.

• 28:27Speaker 01

  Really?

• 28:27Harry Stebbings?

  Yeah.

• 28:28Speaker 01

  Block those people.

• 28:29Harry Stebbings?

  Why do you do them? Why do you do them?

• 28:31Speaker 01

  Please block those people.

• 28:32Harry Stebbings?

  And you know what I find so funny is I also get fifty or sixty or seventy people who are like, I called my mum today to tell her that I loved her and she was so happy because of that. And that's why I do it.

• 28:43Speaker 01

  But those posts really resonate with me personally. And a little bit, I live my life through you in that post in that moment. You know, that that close relationship with your mum is special. And and I and I think it's quite a nice way of showing the human side to someone who's successful.

• 28:55Harry Stebbings?

  That's the amazing thing with content though, which is that people can build a relationship with you when you've never met them before.

• 29:00Speaker 01

  Yeah.

• 29:00Harry Stebbings?

  And I have so many of the biggest CIOs of the biggest institutions in the world, who will come on to a call and be like, I love your post with your mum. By the way, I love how you're so open about eating disorders. And I'm like, fantastic. Who are you? And it's a great way to pre-sell to have content as your relationship builder at scale.

• 29:20Speaker 01

  I was gonna say that earlier when you were talking about having a mentor. Basically, you don't need to necessarily have someone who's gonna sit down with you every day. You can literally see someone whose life you like. They've got, you know, like you said, good marriage, good business, good ethics. You can just follow their content and you can you can make them your mentor without them even realising it.

• 29:39Harry Stebbings?

  A hundred percent.

• 29:40Speaker 01

  And people don't realise that though. A lot of the time I get DMs, I'm sure you do too. I pretty much get a hundred DMs a week where someone says, please be my mentor. I'm like, I've made content for you. Let's pretend I am your mentor. Here's a load of content for you to go and watch, you know, like feel free to follow me and see what's going on, you know? Mentorship has got people a bit confused. They think they need to sit down with that person and have one-on-one conversations all the time, but the best mentors haven't got time for that.

• 30:02Harry Stebbings?

  Yeah, I agree. It's almost like, you know, it's almost like dating, which is like the best way to attract your partner is to work on yourself and make yourself someone that would want to be partnered with.

• 30:12Speaker 01

  Yep.

• 30:12Harry Stebbings?

  If you want to be a mentee of mine, make yourself someone that I would want to mentee or mentor.

• 30:18Speaker 01

  Yep. Well, I like as well, I like the line about I only hire people that I would work for. So then it's a two way street of learning as well, right, so.

• 30:26Harry Stebbings?

  The only challenge is I'd never work for anyone.

• 30:28Speaker 01

  Yeah, well, that's the thing, you know, I've got a team, I've got forty one people in the team. Every single one of them could start their own business. So there's something really interesting in bringing all entrepreneurs together to work together. And I also, you know, as someone that doesn't want to work for someone, a lot of these people wouldn't traditionally work for someone.

• 30:43Harry Stebbings?

  Yeah.

• 30:43Speaker 01

  I think if you have a similar mission, it's the whole, I'd rather have five percent of Facebook than a hundred percent of MySpace.

• 30:48Harry Stebbings?

  Hundred percent.

• 30:49Speaker 01

  Right, so there's something also in the whole like balancing act, you've just got to let people have their own cages, I guess, their own own areas as entrepreneurs.

• 30:56Harry Stebbings?

  But also, the biggest way to make money as a young person is just to work harder than anyone else. Like, if you work really, really hard and you have the time as a young person, you will inherently increase your chances of being successful significantly.

• 31:10Speaker 01

  Yeah.

• 31:11Harry Stebbings?

  Most young people actually, and this is the truth that will make me unpopular. Most people say they want to make money, most people say they want to be successful. You don't understand the commitment, it's every weekend, it is absolutely relentless. Most people say they want it, but they actually don't want what it takes.

• 31:27Speaker 01

  I saw a post from you a little while ago where you kind of worked every Sunday for twelve years or something, you know. And I think the thing is, again, it links back to all this stuff links together, is like, if you enjoy it, you won't call it work. Work's a weird word. Like, to some people, the word work is a very negative thing, I've got to go to work. To me, I love work, like, I've always loved work.

• 31:47Harry Stebbings?

  I don't know, I've only ever done work, like, since I was seventeen. Like, I don't like holidays and people are like, oh, it's because you're a hustle culture, bro. No, it's not. The honest truth is I really struggle on holidays because I'm forced to not be at work.

• 32:01Speaker 01

  Yeah.

• 32:01Harry Stebbings?

  And work is such a huge part of who I am, that you basically stare into the abyss and you don't have anything staring back at you.

• 32:08Speaker 01

  True.

• 32:09Harry Stebbings?

  It's very uncomfortable.

• 32:10Speaker 01

  But again, like holidays, behind the scenes, folks, before we sat down here together, Harry was sitting with Phoebe Gates, Bill Gates's daughter, and doing a podcast. And I went to New York on holiday and ended up meeting her and doing a podcast together. And, you know, so that's my ideal holiday, to be honest.

• 32:27Harry Stebbings?

  Great.

• 32:27Speaker 01

  Go to a city, see it, meet great people, do cool stuff, make content that helps people. Like, that is a holiday. But to most people, like, didn't you have any time off? I'm like, yeah, I went to New York.

• 32:36Harry Stebbings?

  I totally agree. I think like, you know, my business partner always tells me very correctly, life is like a cooker in a kitchen. There's four hobs, you know, that you turn on. There's family, there's friends, there's work, and there's fitness. Okay, family, friends, work, and fitness. And the trouble is, you can only keep two on at the same time. And so I've got a hack for you. I hired my family. My mum and my brother work for me. Okay, fitness, I always hold true. I work with my best friends and my partners in my business. And so like four become two.

• 33:09Speaker 01

  A hundred percent. This is a brilliant hack. I would say like, I work while I'm on the treadmill, you know? So you can do exercise and work at the same time, right? I'm actually looking at investing in a gym, because then I can go with my team to the gym. You know, like, why can't you combine these things? And that's, I've heard that saying too, and I love the point about combining.

• 33:28Harry Stebbings?

  You know, another big problem that young people face is they think that you have to have innovative ideas. And I know that sounds ridiculous, what are you talking about? But very often, you can just take something that works and make it 10 or 20% better. Oh, I love that cafe, but I've always wondered why they don't do really Instagrammable cakes? Because the coffee is great and the location is great. Why don't they do more? Making something 10 or 20% better is very often a great, successful business.

• 33:53Speaker 01

  Well, you reinvented the VC model, thinking that way, to be honest. You know, you took the existing VC model, which works. Many people make a lot of money out of it and help a lot of businesses succeed. And you reinvented it with the media side, because no one was doing that.

• 34:06Harry Stebbings?

  Distribution. No one was doing it. It's the power of being first.

• 34:09Speaker 01

  And I just think that people, you know, if you look at brands like Liquid Death, you look at the reinvention of existing, everyone is trying to come up with a brand new idea. And they're not starting until they've got the biggest new idea. I'm reinventing education, so I'm taking. The broken education system, I'm reinventing it. It's not, it's not a genius idea, is it? Education in general was not a new thing.

• 34:26Harry Stebbings?

  I would say you're a great answer, though, to innovative content. And I think a big problem that I see with a lot of people making staying content is they're like, I'm gonna do one-on-one interviews with entrepreneurs. And they just copy what works and think that'll do it. You know, what made yours very successful, I think, is a very innovative hook, respectfully, which is you go up to people on the street and say, what's your dream? I'm like, fuck, I'm in. Like, what's this? People need to be a lot more creative around the content that they create and not just copy what works.

• 34:56Speaker 01

  Back to your point earlier, it's an iteration. So I started out with a typical podcast, you know, and then I went into the street eventually. And I just originally said, oh, what business would you start? Which isn't a great hook, is it? And I realized that wasn't quite working. So everything, it wasn't like I'm a genius. And I sat there one day with this big, massive plan. You know, I just literally executed every day until it got better and better. That's, that's the part of it.

• 35:17Harry Stebbings?

  The defensibility of a company is the daily processes that you create and maintain, sustained over long periods of time. It's rarely actually the product. The product is the output. It's the way that we create thumbnails. It's the way that we create hooks. It's the way that we create short form. It's the way that we do long form. It's all of the little things that come together to do the big thing. You know, my, my dear friend is the CEO of Spotify, Gustav Soderstrom. And he says, the details are not the details, they are the product.

• 35:47Speaker 01

  Hmm, I love that. All of this stuff could be on T-shirts. Let's finish off our list. Number six, number six.

• 35:53Harry Stebbings?

  Yeah, I, I just think too many people worry that the vision that they have is too ambitious. It's too hard. I can't re-educate the world and change people from going to university to starting their own business. It's too unattainable. It's like a marathon. Break it down, focus on the short term, the next milestone that you can hit. Only when you hit that do you unlock the next. I think people need to focus very much on more achievable goals that will unlock nuance.

• 36:23Speaker 01

  So true. I, I am trying to fix the education system and I'm making one TikTok a day to make that happen.

• 36:29Harry Stebbings?

  Fantastic. But if I said to you, you're gonna shift a trillion dollars of education spend, you're like, well, Jesus.

• 36:34Speaker 01

  So I'm six years, next year I'm doing that. But, but this year I'm just making one TikTok a day that helps people learn business.

• 36:41Harry Stebbings?

  A hundred percent.

• 36:42Speaker 01

  Yeah, yeah. So number seven?

• 36:44Harry Stebbings?

  Yeah, I always think of Hitch. Have you seen Hitch?

• 36:47Speaker 01

  Yes, I have, yeah.

• 36:48Harry Stebbings?

  Okay, so there's a scene with Albert Brennaman where he's trying to woo, you know, the woman he's trying to chase. And the lesson is always make the best friend like you. And the power of pillow talk is incredibly real. At the end of the day, a partner's statements about someone will very often impact their decision. So whenever I go to a dinner or a drinks party or whatever, the partner of the person that I want to influence will be my best friend. Cause the power of the car journey home is what dictates what Simon actually does.

• 37:19Speaker 01

  That's actually so true.

• 37:20Harry Stebbings?

  When your wife goes, Harry was so lovely. Everyone kind of focused on you, but he spent so much time. He asked about the kids. He was really great. So I'd spend more time with him, Simon. You're like, hmm, interesting.

• 37:31Speaker 01

  I think that, again, it's so, the thing that people, okay, so I, I went to Saudi recently. It's a country that a lot of people have an opinion on. I wanted to go see for myself what it was, what was going on there. And the guy that picked us up at the airport, I originally thought, oh, he's the driver, just picking us up. So he picks us up, we go to the hotel lobby, he's literally like opening the door for me like a chauffeur. And then helps me to the counter and tells the person, Simon Scribbs here and signs all this document. And I, I really liked him. So I was just genuinely being nice to him. Anyway, turns out he's Will Smith's like right hand man and he's like connected to all these celebrities. You know, he was being really humble with me at the airport and with the sign, Simon Scribbs and opening the door.

• 38:12Speaker 01

  This guy's so connected. And I didn't realise he was disconnected till three days into the trip, at the end of the trip. He said, well, Simon, you know, connect on Instagram. And he gave me his Instagram and suddenly I see all these friends and all these relationships he's got. And I was so pleased with myself. I'm genuinely trying to be nice to everybody. I'm not treating the person who's, I think, my chauffeur badly. People make that mistake. You just never know. Always be polite, people.

• 38:34Harry Stebbings?

  The single biggest way to increase your happiness is to ask for two people's names. For me, it's the barista in my favourite coffee shop and the receptionist in my gym. Two people you have the highest frequency of contact with on a daily, cause every day you go and see them. And saying, hey, what's your name? I'm so sorry, I missed it. Your name's Amy. Great. I'm Harry. Cool. Next day, Amy, how are you? Oh, I'm good, Harry. How are you? You will increase happiness so significantly with those two little changes.

• 39:02Speaker 01

  I think people listening, just to conclude, I'm going to call you my patient zero for what's your dream, you know, you made it happen and you made it happen with sheer willpower. And I'm so grateful you've come on this podcast today and shared your knowledge. Thank you so much for having me. I really appreciate it. Appreciate you.

• 39:19Harry Stebbings?

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• 40:03Harry Stebbings?

  work, so teams can focus on real work with real impact. Don't let anything get in the way of your next breakthrough. Leave the travel and spend to Perk. Visit perk.com/20vc today. Perk, powering real work. Just as Perk rewards your professional milestones, Daily Body Coach helps you celebrate and sustain your personal wellness wins. You know how so many founders and execs say they'll finally take care of their health once things slow down? Well, they never do. Running a business is a marathon made of high-intensity sprints, and taking care of yourself is what gets you through those times performing at your best, both professionally and personally. This is exactly where Daily Body Coach comes in. Daily Body Coach is a complete, high-touch

• 40:48Harry Stebbings?

  service for busy founders and executives, combining personalized nutrition and training with psychology-based coaching to help you not just follow a plan, but actually build the systems, habits, and mindset to stay at the top of your game. Built by an exited founder and led by certified experts with masters and PhD-level credentials, Daily Body Coach is fully tailored to your life, whether you're traveling. Dining out or in back-to-back meetings, you get daily accountability, data-driven insights from DEXA scans and blood work and a highly certified team backing you. If you're serious about performing at your best, physically and mentally, go to dailybodycoach.com/20vc.

• 41:30Harry Stebbings?

  That's dailybodycoach.com/20vc and take the next step. While Daily Body Coach helps you build healthier habits, Air Wallets helps you get paid globally without the headache. Founders, let's get real about the growth tax. You've raised VC funding and you're scaling globally and it's no longer about shipping product. It's about orchestrating operations across continents. But suddenly, your payments and finance stack is choking your growth. You're logging into lots of different banking portals, waiting days for transfers and wasting hundreds of hours on manual reconciliation and reporting across entities. It's operational drag and it's at your scale. It's costing millions. That's why I'm so excited to partner with Air Wallets. Air Wallets are more than just a banking alternative to HSBC or Citi.

• 42:15Harry Stebbings?

  Air Wallets brings you an intelligent financial operating system that powers how global businesses operate and grow, allowing you to manage and automate banking, treasury, payments and spend. The most exciting part for me, they're heavily investing in agentic finance. If you're scaling globally, you need a banking and finance platform that's borderless, real-time and intelligent. Check out Air Wallets today and see how they're helping thousands of businesses like Canva, McLaren and Deal scale at airwallets.com/20vc. Terms and conditions apply. Your money is a safeguarded, not FSCS protected. See airwallets.com for more details.