← The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
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)
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- [00:00]
Harry Stebbings
This is 20 VC with me, Harry Stebbings.
- [00:02]
Simon Squibb
Now, I'm very often asked to reveal.
- [00:04]
Harry Stebbings
A little bit about my story and I'm always quite reserved in doing so.
- [00:08]
Simon Squibb
I think you have to really return.
- [00:10]
Harry Stebbings
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 fund, how I got Mark Benny off to come on 20 VC through 53 cold emails and many, many more cool stories. But before we dive into the show.
- [00:52]
Simon Squibb
Today, this episode is brought to you by perc, the intelligent platform for Travel and spend Every successful founder remembers their breakthro, 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 PERC was built for. One recent study found shadow work cost companies over 1.7 trillion every year as employees waste hour 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 PERC. Visit perc.com 20vc today. Perk Powering real Work Just as Perc 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.
- [02:01]
Harry Stebbings
Their health once things slow down?
- [02:03]
Simon Squibb
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 service for busy founders and executives combining personalized nutrition and training with psychology based coaching to help you not just follow a plan but 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 that's dailybodycoach.com 20vc and take the next step. While Daily Body Coach helps you build healthier habits, Airwallies helps you get paid.
- [03:12]
Harry Stebbings
Globally without the headache Founders let's get.
- [03:15]
Simon Squibb
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, 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 Airwallex. Airwallets are more than just a banking alternative to HSBC or Citi. Airwallex 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.
- [03:59]
Harry Stebbings
Heavily investing in agentic finance.
- [04:01]
Simon Squibb
If you're scaling globally, you need a banking and finance platform that's borderless, real time and intelligent. Check out Airwallets today and see how they're helping thousands of businesses like Canva, McLaren and Deal Scale. @AirWallets.com 20VC terms and conditions apply. Your monies are safeguarded, not FFSCs protected. See airwallets.com for more details.
- [04:24]
You have now arrived at your destination. 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?
- [04:38]
Harry Stebbings
Yeah, I mean I very clearly remember my mother telling me that she had Ms. And she'd had Ms. For about 5 years before but the Ms. Medication was like $750,000 and I had this useless podcast at the time which had no listeners and we can get to the Importance of persistence. No listeners.
- [04:55]
Simon Squibb
And I thought, gosh, how do I.
- [04:56]
Harry Stebbings
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 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.
- [05:22]
Simon Squibb
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.
- [05:34]
Harry 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, P.S. i know that McKellen75 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.
- [05:57]
Simon Squibb
It's effort, isn't it? I think just a little bit. 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, Sam, 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.
- [06:18]
Harry Stebbings
Everything is important and so few do it. If you want to win, be a purple cow.
- [06:24]
Simon Squibb
Yeah, of course. I love that.
- [06:25]
Harry Stebbings
Just be different. It is so important.
- [06:27]
Simon Squibb
So you have interviewed, is it 107 billionaires?
- [06:31]
Harry Stebbings
Yeah, yeah, yeah.
- [06:32]
Simon Squibb
So first of all, how did you manage to get 107 billionaires? Is it a similar thing? Just persistence?
- [06:38]
Harry 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.
- [07:08]
Simon Squibb
I love that. But it does make a big difference, right? So 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 were working with cnn. Sure. Okay, come on in. So you just have to use that social proof a hundred percent. 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 sometimes.
- [07:35]
Harry 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 onto 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.
- [08:01]
Simon Squibb
Now you said earlier something else off camera. I want people to know this. You raised 70 million on WhatsApp. 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.
- [08:15]
Harry Stebbings
I mean, you know, when we fundraise, 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 a 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 2 million. What people don't see is the 10 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 course, meetings, I always say, simon, I'm terrible at email. Let's jump to WhatsApp. And then at the weekend when I'm walking with my mom, I'll send a photo of Me and Mum eating a donut. And I'll say, God loved our meeting this week. Next time you got to join us on our walk. People resonate with people and so I build those relationships on WhatsApp unlike anyone else.
- [09:07]
Simon Squibb
Well, I think I've been building a relationship with you for 13 years. So we actually first met. People might not even know. My audience is quite young, you know, they might have no periscope. I remember 13 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 time. And, you know, I'm launching a podcast, I'd love to have you on. And I feel like for 13 years I've been following you ever since. And your rise and what you've done has been an inspiration. Do you remember that?
- [09:38]
Harry Stebbings
I do, I do, actually. But I mean, wow, it takes me back. I remember Periscope and Meerkat was 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.
- [09:55]
Simon Squibb
You didn't say that to me. I don't remember that, to be honest.
- [09:58]
Harry Stebbings
But the point of that is, 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 99% 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.
- [10:29]
Simon Squibb
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 19 year old story, because you didn't have a big following.
- [10:39]
Harry Stebbings
Did not have a big following at all. And I leveraged ego and insecurity of famous people and successful people to make money.
- [10:46]
Simon Squibb
And you did something you didn't. You see what I think with that case, with the whole 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. We didn't just want a million pounds for the sake of it, you needed it, so that's why it had to happen.
- [11:07]
Harry Stebbings
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'm fortunate that I have 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 because I have money. 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.
- [11:42]
Simon Squibb
And that's why I think starting young is quite important, because you can take more risk when you're young, which is why I know we're both on the same train. University for 90% of people is a waste of time.
- [11:53]
Harry Stebbings
Totally.
- [11:54]
Simon Squibb
Four years of your life, forget the money you can waste at university, but those four years of these, you can sleep on a couch with a friend, you can stay at home for a little bit longer, you can take risk. Right.
- [12:05]
Harry Stebbings
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 haven't.
- [12:15]
Simon Squibb
No, no, you're not, though.
- [12:16]
Harry Stebbings
So it's not on the bench. But I notice now my stamina at 30 is not what it was at 20. 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 going to work. That's not going to work. And in America, we say, that's going to work. We need much more positive visualization in the uk.
- [12:55]
Simon Squibb
How would you go about making that a reality in the uk? Do you think there's a fix?
- [13:00]
Harry Stebbings
Yeah, I do. It's why I started Project Europe, which is a $10 million fund which gives 200 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 queues outside the corner and then you become the next Cedric Grolet. Bakeries in every city, in every big country, you know, even.
- [13:35]
Simon Squibb
You just do it for a year and you realize it wasn't for you. But at least you don't live with regret 100%. At least you tried, right?
- [13:41]
Harry 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 think about that. I would have been a mid lawyer. There's nothing wrong with that.
- [13:57]
Simon Squibb
Bad luck turns into good luck over time if you leverage it right.
- [13:59]
Harry Stebbings
Yeah, but that's where the individual comes in, which is like, only you decide 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, fuck, I'm bulimic, I don't have a passion.
- [14:16]
Simon Squibb
Woe is you could have taken it as a, you know, as a reason to not go for it 100%.
- [14:21]
Harry Stebbings
You decide the next step.
- [14:22]
Simon Squibb
What do you think that thing is where you take it and make it positive and some people take it and make it negative. 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?
- [14:32]
Harry Stebbings
I think it was, 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. Yeah, big, big lesson 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.
- [15:16]
Simon Squibb
Yeah, I love that the 19 year old you idea there. Just want to pick at that for a second. Because 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 45 years old. All of my peers laughed at me when I was on TikTok. I was around the 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 10 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. And I think it's important just to pick at it for a second because a lot of people be listening, like, well, I don't know how to interview. You weren't a great interviewer at the beginning. Right.
- [16:08]
Harry Stebbings
I was 18, I spent $50 and I bought a microphone on Amazon. An Iceball 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 1,000 plays. Simon, you've been building this media now six years.
- [16:32]
Simon Squibb
First three years, nothing. I got no.
- [16:34]
Harry 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.
- [16:47]
Simon Squibb
Right.
- [16:47]
Harry Stebbings
So why don't you do it anyway?
- [16:49]
Simon Squibb
That's a great framework for people to go and apply to 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 100%. 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, ability to sell. And frankly, marketing, it's distribution, totally distribution. 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.
- [17:16]
Harry 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 4 million in revenue from one LinkedIn post. Crazy for an investor to bring you 4 million from one post.
- [17:41]
Simon Squibb
Especially as most investors say they're going to bring you value. They give you a bit of advice. Actual value.
- [17:46]
Harry 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.
- [17:56]
Simon Squibb
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 again they drawed all the attention. I think the next big platform is a creator 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, Starbucks. 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?
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Completely agree with you.
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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.
- [18:42]
Harry 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 MrBeast where Mr. Beast started doing his own product. Now I think you've got to be careful about the products that you choose. You know, MrBeast did MrBeast burgers bad. And he'll say this himself, bad product to choose. Difficult to monitor quality, difficult time delivery.
- [19:15]
Simon Squibb
Clever scale mechanism because he worked with outside partners about quality control was a problem Exactly.
- [19:20]
Harry Stebbings
And so I think you've got to.
- [19:21]
Simon Squibb
Choose your product well.
- [19:22]
Harry Stebbings
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.
- [19:29]
Simon Squibb
So let's quickly, just very quickly, run through the seven things that billionaires have taught you. So number one, just say a sentence if you like.
- [19:35]
Harry 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 5 million and the other invested 7 million. If you accept no, I would have not had 12 million there for the fund.
- [20:10]
Simon Squibb
Unbelievable. So true. Next lesson, so important.
- [20:14]
Harry Stebbings
Lesson number two. You have to continuously beat down the door. I emailed Marc Benioff from Salesforce 53 times. I've heard about this guy every single Sunday.
- [20:24]
Simon Squibb
Why didn't he block you?
- [20:26]
Harry 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. P.S. i hope that you're enjoying the McAllen 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.
- [20:51]
Simon Squibb
Was I instantly just said, what's the exact center? I'd love to know the exact reply. What was it? Yeah, come on.
- [20:55]
Harry Stebbings
I think it was like, yeah, I'm in.
- [20:56]
Simon Squibb
Yeah, I'm in.
- [20:57]
Harry Stebbings
And that was kind of it.
- [20:58]
Simon Squibb
After 53, CCing my team.
- [21:01]
Do you know, sometimes people talk about this approach. Like, for example, if you found out whose 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.
- [21:11]
Harry Stebbings
Very smart.
- [21:12]
Simon Squibb
Any other strategies like that you've seen on the sales side?
- [21:15]
Harry Stebbings
The one thing I would just say is, like, 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.
- [21:35]
Simon Squibb
That's great, because that keeps you going doing it too. Right? I've emailed him 100 times. He still hasn't replied. He's also content.
- [21:40]
Harry Stebbings
And then, you know what? Also everyone goes, oh, wow, Mark Benioff's going on Harry's show.
- [21:45]
Simon Squibb
Harry's getting legit guests these days.
- [21:48]
Harry Stebbings
And then guess what? You can actually take it to the off and be like, hey, look, I go viral with tweets like this and you get more social validity.
- [21:56]
Simon Squibb
Super important.
- [21:57]
Brilliant. Third thing.
- [21:59]
Harry Stebbings
So important. I was terrible when I started. I was not charismatic. I sucked at interviewing people. But 99% of people never, ever start. I think the most important thing is just to take the first step. Activity drives outcomes. Most often, you don't actually know where it's going to end up, but you will never find out if you don't start.
- [22:23]
Simon Squibb
Just start. Sell swimming trunks.
- [22:25]
Harry Stebbings
You know what you're going to 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. 99%.
- [22:40]
Simon Squibb
We use that one human skill. We have, a special skill that no other animal has, which is the ability to predict the future, and we use it against ourselves to predict a fate.
- [22:47]
Harry Stebbings
Failure.
- [22:48]
Simon Squibb
100% mental, isn't it?
- [22:49]
Harry Stebbings
It's also like 99% of the worries that you have have never happened.
- [22:52]
Simon Squibb
Yeah. Yeah. And the upside is actually far greater than you think. You can't actually predict what's going to happen.
- [22:57]
Harry Stebbings
Way greater. I could never have expected my life to be what it is.
- [23:01]
Simon Squibb
100%. Yeah. 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, all right, go into the street and ask people, but why 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 that 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 accountable to. Like, if I don't hire someone, I found I'm a bit lazy. I don't have to do it, so I won't do it. You need to give yourself accountability. 100 Monday morning, I've got a member of staff saying, simon, what are we doing this week? I'm like, okay, I've got to go do it.
- [23:55]
Harry Stebbings
You know, like, 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.
- [24:18]
Simon Squibb
But it must have been a big moment to leave that decision to leave.
- [24:21]
Harry Stebbings
Yeah, it was. I remember very much. I got a call from a sponsor and they said, we want to sponsor the show. And I said, how much is it? And I said, It's $100,000. And they were like, fantastic, send us over the paperwork. I didn't know what the paperwork meant.
- [24:39]
Simon Squibb
And there was no AI then, either.
- [24:41]
Harry Stebbings
But to our point, on the valueless nature of university, I think I just googled contracts and I built my own contract by Googling, and that's what I use for this hundred grand. But I went to my law professor and I said, how much do you earn a year? And he said, 82,000. And I thought, okay, well, that's my answer.
- [24:59]
Simon Squibb
There you go.
- [25:00]
Harry Stebbings
And so I called up my parents and I said, I'm leaving university. And, you know, this is following my dream.
- [25:06]
Simon Squibb
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 cut customer. You can tell a customer what you're going to 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.
- [25:19]
Harry Stebbings
100, 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 30 grand for that, right? 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.
- [25:36]
Simon Squibb
100%. Yeah, big one. So number four, I think the biggest.
- [25:41]
Harry Stebbings
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. It's 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.
- [26:11]
Simon Squibb
Got it.
- [26:11]
Harry Stebbings
Number five, I think a big problem that young people have today. What do you want to 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, 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 to bring to that table. And I looked at my bank balance which had a million in it, and I was like, like this doesn't feel like the who Wants to be a Millionaire moment when the confetti is coming down and it's like this glory. I was very unhappy at that moment.
- [27:10]
Simon Squibb
And it taught me something really important.
- [27:12]
Harry Stebbings
Actually, which is ask yourself a very simple question. What truly makes you happy in life that truly makes you happy? For me, it's walking around Hyde park with my mother and getting an espresso. The espresso's are £2 80. So for a good £5 60 you'll be good to go on your two espressos. That is my happiest moment period. So £5 60 is my happiness. Okay, that's good to know.
- [27:36]
Simon Squibb
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. Yeah.
- [28:01]
It's like, don't chase it, don't chase it.
- [28:03]
And I think the nuance of this, again, I don't want anyone to miss this, is like, you've got to have a center. Right. So I see your posts about you going to see your mum. You 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 allocate time to the happy place.
- [28:22]
Harry Stebbings
You know what's so funny? I get people in my DMs be like angry about my mother post. Really? Yeah. Like, why do you do them? Why do you do them? Why do you do them?
- [28:32]
Simon Squibb
Please block those people.
- [28:32]
Harry Stebbings
And you know what I find so funny is I also get 50 or 60 or 70 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.
- [28:43]
Simon Squibb
Those posts really resonate with me personally and a little bit. I live my life for you in that post, in that moment. You know, that close relationship with your mom, it's special and I think it's quite a nice way of showing the human side to someone.
- [28:55]
Harry Stebbings
That's the amazing thing with content though, which is that people can build a relationship with you, you when you've never met them before. 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 mom, 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.
- [29:21]
Simon Squibb
I was going to say that earlier when you were talking about having a mentor. Basically. Basically you don't need to necessarily have someone who's going to sit down with you every day. You can literally see someone whose life you like. They've got a, you know, like you say, good marriage, good business, good ethics. You can just follow their content and you can, you can make them your mentor without them even realizing it. 100 and people don't realize that though. A lot of time I get DMs. I'm sure you do too. I pretty much get 100 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.
- [30:02]
Harry 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. Yeah. If you want to be a mentee of mine, make yourself someone that I would want to mentee or mentor.
- [30:18]
Simon Squibb
Yeah, well, I like as well. I like the line of about I only hire people that I would work for. So then it's a two way street of learning as well. Right.
- [30:26]
Harry Stebbings
So the only challenge is I'd never work for anyone.
- [30:28]
Simon Squibb
Yeah, well, that's the thing, you know, I've got a team. I've got 41 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. I think if you have a similar mission, it's the whole, I'd rather have 5% of Facebook than 100% of my space.
- [30:49]
Harry Stebbings
100%.
- [30:49]
Simon Squibb
Right. So there's something also in the whole like balancing act, you could just got let people have their own cages, I guess their own own areas as entrepreneurs.
- [30:56]
Harry 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. 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.
- [31:28]
Simon Squibb
I saw a post from you a little while ago where you kind of worked every Sunday for 12 years. 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.
- [31:48]
Harry Stebbings
I don't know. I've only ever done work, like, since I was 17. I don't like holidays. And people are like, oh, it's because.
- [31:54]
Simon Squibb
You'Re a hustle culture, bro.
- [31:56]
Harry Stebbings
No, it's not. The honest truth is I really struggle on holidays because I'm forced to not be at work.
- [32:02]
Simon Squibb
And work is such a huge part.
- [32:03]
Harry Stebbings
Of who I am that you basically stare into the abyss and you don't have anything staring back at you. It's very uncomfortable.
- [32:11]
Simon Squibb
But again, holidays behind the scenes, folks. Before we sat down here together, Harry was sitting with Phoebe Gates, Bill Gates, his daughter, and doing a podcast. And I. I went to New York on holiday and ended up meeting her and doing a podcast together. And, you know, so that's. That's my ideal holiday, to be honest. 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.
- [32:37]
Totally agree.
- [32:38]
Harry Stebbings
I think, like, you know, my business partner always tells me very correctly, life is like a cool 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 in 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 mom and my brother. Work for me. Okay? Fitness.
- [33:02]
Simon Squibb
I always hold true.
- [33:04]
Harry Stebbings
I work with my best friends and my partners in my business. And so, like, four become two. And I keep that.
- [33:11]
Simon Squibb
This is a brilliant hack. 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 that. I've heard that saying, too, and I love the point about combining.
- [33:28]
Harry Stebbings
So 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 Instagramable cakes. Because the coffee is great and the location is great. Why don't they do more cake? Making something 10 or 20% better is very often a great successful business.
- [33:53]
Simon Squibb
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. No one was doing that.
- [34:06]
Harry Stebbings
Distribution, no one was doing it. It's the power of being first.
- [34:09]
Simon Squibb
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 start 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 a genius idea, is it? Education in general was not a new thing.
- [34:27]
Harry 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 stay in content is they're like, I'm going to do one on one interviews with entrepreneurs and they just copy what works and think that'll do it. What made yours very successful, I think is a very innovative hook, respectfully, which is you go out to people on a street and say, what's your dream? I'm like, 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.
- [34:56]
Simon Squibb
But 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, 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.
- [35:18]
Harry 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.
- [35:32]
Simon Squibb
It'S the way that we create short.
- [35:34]
Harry Stebbings
Form, it's the way that we do long for. It's all of the little things that come together to do the big thing. My dear friend is the CEO of Spotify, Gustav Soderstrom. And he says the details are not the details, they are the product.
- [35:48]
Simon Squibb
I love that all this stuff could be on T shirts. Let's finish off our list. Number six. Number six.
- [35:53]
Harry Stebbings
Yeah. 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, sustainable. 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 new ones.
- [36:24]
Simon Squibb
So true. I am trying to fix the education system and I'm making one TikTok a day to make that happen.
- [36:29]
Harry Stebbings
Fantastic. But if I said to you, you're going to shift a trillion dollars of education spend and you're like, well, Jesus.
- [36:35]
Simon Squibb
I'm six years next year I'm doing that. But this year I'm just making one TikTok a day that helps people learn business 100%. So number seven. Yeah.
- [36:45]
Harry Stebbings
I always think of Hitch. Have you seen Hitch?
- [36:48]
Simon Squibb
Yes, I have. Yeah.
- [36:48]
Harry Stebbings
Okay, so there's a scene with Albert Brenneman 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. 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. Because the power of the car journey home is what dictates what Simon actually does.
- [37:20]
Simon Squibb
She's so true.
- [37:20]
Harry 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 would spend more time with him. Simon. And you're like, interesting.
- [37:31]
Simon Squibb
I think that again. So the thing that people. Okay, so I went to Saudi recently. As 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 I was 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, and 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 with the sign Simon Squibb and opening the door, this guy's so connected. And I didn't realize he was disconnected till three days into the trip. At the end of the trip, he said, oh, Simon, you know, connect to Instagram. And he gave me his Instagram. And suddenly I see all these friends and all these relationships, relationships he's got. And I was so pleased with myself that 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.
- [38:35]
Harry 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 favorite coffee shop and the receptionist in my gym. Two people you have the highest frequency of contact with on a daily because 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.
- [39:03]
Simon Squibb
I think people listening. Just to conclude, I'm gonna call you my patience here over. 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.
- [39:15]
Harry Stebbings
Thank you so much for having me. I really appreciate it.
- [39:17]
Simon Squibb
Appreciate you.
- [39:20]
But before we leave you today, this episode is brought to you by perc, the intelligent platform for travel and spend. Every successful founder remembers their breakthroughs, those moments in the journey that change 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 PERC was built for. One recent study found shadow work costs companies over 1.7 trillion every year as employees waste hour 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 PERC. Visit perc.com 20vc today. Perk Powering real Work Just as Perc 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.
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Harry Stebbings
Their health once things slow down?
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Simon Squibb
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Harry Stebbings
Globally without the headache Founders let's get.
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Simon Squibb
Real about the growth tax. You've raised VC funding and you're scaling globally and it's no longer about shipping 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 AirWallets. AirWallets are more than just a banking alternative to HHSBC or Citi. Airwallets brings you an intelligent finance 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.
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Harry Stebbings
Heavily investing in agentic finance.
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Simon Squibb
If you're scaling globally, you need a banking and finance platform that's borderless, real time and intelligent. Check out airwallets today and see how they're helping thousands of businesses like Canva McLaren and deal scale@airwallets.com 20 VC terms and conditions are supply. Your monies are safeguarded, not FFSCs protected. See airwallets.com for more details.