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)

Harry, thanks for being here. Off camera, we were just talking about how you were 19 years old and made £1.5 million. Can you talk a little bit about that before we get into all the lessons you're going to teach us today?

I very clearly remember my mother telling me that she had MS. She'd had MS for about 5 years, but the MS medication was $750,000. I had this useless podcast at the time, which had no listeners, and we can get to the importance of persistence.

1. The Million Dollar Cold Email

I thought, “Gosh, how do I leverage this to make money to pay $750,000 when I’d made no dollars?” I went up to my bedroom, emailed 25 of the biggest CEOs in technology, and 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 £100,000 procurement budget, and got 19 of them to say yes.

Oh, my God.

That was $1.75 million in 24 hours.

That's unbelievable, and a great lesson about, frankly, creating FOMO and sales. I think sales should be taught in schools.

Schools miss the 2 most important things, which are sales and public speaking. I totally agree with you. And also personality: everyone wants to work with someone they like.

At the end of every single email, I'd put, “P.S. I know that Macallan 75 is your favorite whiskey. I'd love to have one with you when you're next in London.”

The minute you add that, you literally treble your chances of getting a response.

It's effort, isn't it?

Just a little better.

The people I've hired who 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. They're not just saying, “Hi, Simon, I'd like to work with you because I can learn a lot,” which is great, but that's also just taking from me. It's such an important lesson in sales, isn't it? The attention to detail in everything is important.

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

Yeah, of course. I love that whole thing.

Just be different. It is so important.

You have interviewed—is it 101 decacorn founders? Something like that?

Yeah.

So, first of all, how did you manage to get 101 decacorn founders? Is it a similar thing—just persistence?

2. Mastering Cold Outbound

Cold emailing is a real art. Good cold emails need to be short, concise, have a clear ask, and be personal.

Then you use social proof as your weapon. You can say, “I just interviewed Richard Branson, and I would love to have you on the show.” Who wouldn't want to be tied to the brand of Richard Branson and be in that same caliber? Very few entrepreneurs. It's like, okay. I use social proof as a weapon to encourage people that it was a good and strong environment they wanted to be associated with.

I love that. But it does make a big difference, right? When I started Fluid, I rang up a company outside this agency—no one knew it—and said, “Hi, I'm Fluid. I'd love to work with you.” They said, “No, sorry, we're busy.”

So I rang back and said, “Hi, I'm working with CNN, and I would love to work with you.” They went, “Oh, you're working with CNN? Sure, okay, come on in.” You just have to use that social proof.

100%.

It's leverage. Some people don't like sales because they think it means being sneaky. You don't have to be sneaky about it. I think car-salesman vibes are what people think sometimes.

At the end of every show, I would say to people, “Hey, who are 3 people that you think I should have on who would be fantastic?”

When people committed to the 3 names, I'd say, “If I send you an email that you can forward to them, would you mind making the introduction?” When people commit to the 3 names, they're committed to making that introduction.

You always want to create flywheels in any business, where one leads to more success. With every show, I got 3 more introductions.

Now, you said earlier something else off camera. I want people to know this: you raised $70 million on WhatsApp. Tell me a little bit about that. People might hear that and say, “Oh, just WhatsApp. How did you do that?” I think I know, but you should share how you did it.

3. Raising Funds On WhatsApp

When we fundraise, we raise from very rich individuals, and we raise from institutions. In between sets in the gym, I would walk around during my 2-minute breaks and message individuals. I'd say, “Hey, I'm going out to raise a new fund, and I'd love to have you in.”

They would come back with, “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 that I always want people off email. Get people off email. People want to work with people they like. So at the end of calls and meetings, I always say, “Simon, I’m terrible at email. Let’s jump to WhatsApp.”

Yeah.

Then, at the weekend, when I’m walking with my mom, I’ll send a photo of me and Mom eating a donut, 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.

Mm.

So I build those relationships on WhatsApp unlike anyone else.

Well, I think I’ve been building a relationship with you for 13 years. We actually first met—people might not even know; my audience is quite young. They might not know Periscope.

Yeah.

Right. I remember 13 years ago, I was hiking in Hong Kong. Periscope was one of the first live products, and I was live in Hong Kong when you came on my Periscope. You stood out instantly. You said, “Oh, I love this, Simon. I’m launching a podcast. I’d love to have you on.” 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.

Oh.

Do you remember that?

I do. I do, actually. It takes me back. I remember Periscope and Meerkat were the 2 live-streaming products at the time, 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 so on.

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

But the point of that is that people look at the successful people today and think, “I could never be that.”

Mm.

It took years of hard work to get there. You have to go through prolonged periods of not being very good before you get to a certain stage. That’s why people don’t start. What I say is, just take the first step and you’re better than 99% of people.

Mm.

It’s like going to the gym. No one goes to the gym and says, “Treadmill, I love you, old friend.” It’s uncomfortable and hard, but by showing up every day, you get better and better.

People listening to this podcast might be thinking, “Well, Harry’s got a big following. Of course he can WhatsApp people and get money.” That’s why I like your 19-year-old story, because you didn’t have a big following then.

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

Right.

And you did something—you see, what I think with that case, with the whole needing to support your mom part of it, is that it wasn’t just that you wanted success; you needed it.

Yeah.

I think that’s the only flip switch that people need to have. You didn’t just want it. You didn’t just want £1 million for the sake of it; you needed it.

100%.

So that’s why it had to happen.

4. Chasing The First Million

I would also say: you should aggressively chase making your first million more than anything else, because the hardest to make is your first million, by far.

Mm.

The world also 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.

Mm.

I get better investment products.

Mm.

I get access to things that most other people can’t because I have money. But it feels wrong.

Mm.

The world is unfair and wrong. My advice would be to chase the first million, because it unlocks so much more than you could anticipate.

That’s why I think starting young is quite important, because you can take more risks when you’re young. I know we’re both on the same train of this: university for 90% of people is a waste of time.

Totally.

Four years of your life. Forget the money you can waste at university, but those 4 years are the years when you can sleep on a couch with friends, stay at home for a little bit longer, and take risks.

You also have the endurance. It is hard work being an entrepreneur, and you will have to work insane hours. I notice this now. I’m not as young as you are—

I’m pretty young also. It’s not an offense.

—but I notice now that my stamina at 30 is not what it was at 20.

Mm.

Take advantage of being young.

Yeah.

And being naive. But the biggest problem with the UK is that we are negative. Positive visualization is everything. I never doubted that this would work. This sounds arrogant, but I always knew I would be successful. It never dawned on me that it wouldn’t work.

Mm.

When you visualize something, you make it much more likely to happen, on both the downside and upside. I think the trouble with the UK is that you say an idea and we go, “Oh, that’s not going to work. That’s not going to work.”

Mm-hmm.

In America, people say, “That’s going to work.” We need much more positive visualization in the UK.

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

Yeah, I do. It’s why I started Project Europe, which is a $10 million fund that gives 200 grand to incredibly young people to do unreasonably ambitious things. We need more people to say yes to crazy dreams.

Mm-hmm.

I think snootiness is another massive problem that we have in the UK. It’s like, “Oh, my gosh, why would you go from being a physicist at Cambridge to opening a bakery? That’s a bit beneath you.”

Mm-hmm.

What happens if you open the most successful bakery in London? You document it, have amazing queues outside the corner, and then become the next Cédric Grolet—

Mm-hmm.

—with bakeries in every city and every major country.

Well, even if you just do it for a year and realize it wasn’t for you, at least you don’t live with regret.

100%.

At least you tried, right? That’s—

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.

Yeah.

I would’ve been a mediocre lawyer.

Well, I’m the same.

There’s nothing wrong with that, but—

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

Yeah.

Yeah.

But that’s where the individual comes in. Only you decide the next step, so make a positive decision. When shit happens, you can either accept it or progress and move on. I could have said, “Fuck, I’m bulimic. I don’t have a passion.”

Mm-hmm.

You go—

“Woe is you.”

“Woe is you.”

You could have taken it as a reason not to go for it.

100%.

Mm-hmm.

You decide the next step.

Do you think that some people take what happens to them and make it positive, while others take it and make it negative? What do you think made you do that? Was it, for example, supporting your mom? Was it an external factor? What was it?

I think it was 2 things. First, having a mentor who could actually redirect me in the right way. Second, the ability to end the day.

Mm-hmm.

What I mean by the ability to end the day is that when you have a bad day, you go to bed knowing—my mother always quoted Scarlett O’Hara from Gone with the Wind—

Mm-hmm.

—which is, “Tomorrow’s another day.”

Right.

Do not let the prior day impact the next day.

Right.

Always come at it with a fresh mind. The “woe is me” of one day leading to another series of bad days is very dangerous. A big lesson for me is that if you have the ability to be miserable for no reason, you also have the ability to be excited and optimistic for no reason.

Mm-hmm.

Embrace it.

Yeah. I love that. I want to pick at the 19-year-old-you idea for a second, because what I’m tending to do when I give young people advice now is always talk about media.

Mm-hmm.

It’s partly because I’m in media.

Mm-hmm.

But also, I joined TikTok when I was 45 years old. All of my peers laughed at me. When I was on TikTok, I was around a table of other people who had sold their businesses. They were all buying property and doing these things. I said, “I’m going on TikTok and sharing knowledge,” and they laughed at me.

5. Content Builds Distribution

Now those same people ask me how to get TikTok working for their businesses. But what I'm getting to is that young people can't afford a house. It's too expensive. But on social media, you can make one video today, get 10 million views, sell a product, and make money.

Mm-hmm.

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'd do straightaway, and 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?

I was 18. I spent $50, and I bought a ice ball microphone on Amazon. That's what it's called. I was a terrible interviewer. Point being, you only get good by repeatedly doing it, and it took me 3 years before I probably got good.

Mm-hmm.

It took me 4 years before I got 1,000 plays. Simon, you've been building this media empire now—

6 years. The first 3 years, nothing. Yeah, same.

Oh, wow.

Yeah.

Okay. So, most people give up. This is a game of who can survive the longest.

Mm-hmm.

And the lovely thing about content, Simon, is that 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?

That's a great framework for people to go and apply to their lives.

So true.

Yeah. And the truth is, no one gives a shit anyway. They'll laugh at you until they're no longer laughing, and then they'll be asking if they can come on your podcast. So, 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.

It's distribution.

Totally.

Distribution is everything.

So if you can build distribution, and everybody can, it's kind of a commodity product. Anyone can jump on their phone and start creating a community.

Well, this is why our venture funds are doing so well right now, which is because everyone has a venture capital fund today, sadly.

Mm-hmm.

But not everyone has distribution. You know, I posted about one of our companies, Fixa, which is email autocomplete.

Yeah.

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 1 LinkedIn post.

Crazy.

For an investor to bring you $4 million from 1 post—

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

Yeah. And—

You know, actual value. Yeah.

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.

Yeah.

So I completely agree.

Sponsorship deals—

Yeah.

We were, again, talking a little bit off-camera about this. I have a feeling that 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, like Snapchat and Instagram. Again, they drew all the attention. I think the next big platform is a creator, because, again, why would you promote someone else's brand if you can promote a brand you own? For example, I'm launching a competitor to Starbucks as part of my business model.

Why Starbucks?

Why would I promote Starbucks, which I don't particularly believe in? They might have the money to sponsor me. 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?

Completely agree with you.

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

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.

Mm.

And there is a stage where you get to where absolutely that is the case, and I think you saw it with MrBeast—

Mm.

—where MrBeast started doing his own products. Now, I think you've got to be careful about the products that you choose. MrBeast did MrBeast Burger.

Mm.

Bad, and he'll say this himself—a bad product to choose, difficult to monitor quality, difficult delivery.

Clever scale mechanism, because he worked with outside partners, but quality control was a problem, right?

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.

6. Seven Lessons From Billionaires

So let's quickly, just very quickly, run through the 7 things that billionaires have taught you. Number 1, just say it in a sentence if you like.

Lesson 1 is: never accept no for an answer. When I was fundraising, I got turned down by 2 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 not have had $12 million there for the fund.

Unbelievable. So true. Next lesson?

So important. Lesson 2: you have to continuously beat down the door. I emailed Marc Benioff from Salesforce 53 times.

I've heard about this.

Every single Sunday. 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, and never stopped. On the 53rd time, he responded and said he'd come on the show.

Was that instantly? He just said—what's the exact sentence? I'd love to know the exact reply. What was it? “Yeah, I'm in”?

I think it was, “Yeah, I'm in.”

Yeah, I'm in. Oh.

Yeah, I'm in. That was kind of it after 53. CC-ing my team.

Right. So sometimes people talk about this approach. 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, like, “I was just listening to Harry on 20VC—”

Very smart.

Were there any other strategies like that you've seen on the sales side?

The one thing I would just say is that you always need to think about the next step in content. 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.”

Yeah.

This is the email—

Yeah.

—that converted someone worth $100 billion to come on my podcast.

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

And then, do you know what else? 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.

Mm.

Super important.

So important.

Brilliant. Third thing?

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.

True.

Just start. Sell swimming trunks. You know what you're going to learn? No one wants them, but everyone wants cool goggles. That's the lesson that we take. Just start. I find, honestly, the biggest thing is, it won't work, so I don't start. 99%.

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

Mm-hmm.

And we use it against ourselves to predict a failure.

100%.

Mental, isn't it?

It's also 99% of the worries that you have have never happened.

Yeah, yeah. The upside is actually far greater than you think. You can't actually predict what's going to happen.

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

100%, yeah.

I think at this particular point, just for a second, it really blows my mind. When I first started doing videos on how to raise money, I was talking about how to find a co-founder. The videos were doing okay on the views—typical business content. They were doing average.

Then I thought, right, go into the street and ask people why they're not actually doing it. Most of the time, they're not even giving themselves the time to think of something. That's why “What's your dream now?” is pretty much a standard saying, by the way. When people meet each other now, they ask each other what their dream is. In schools, kids are asking themselves what their dream is.

That starting point of getting people to actually start is the hardest thing. Once you've started, I always hire someone as quickly as I can when I start something now, so then I've got someone I'm accountable to. If I don't hire someone, I've found I'm a bit lazy. I don't have to do it, so I won't do it. You need to keep yourself accountable.

When on 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.”

Sometimes you have to burn the boats to encourage action, right? When I dropped out of university, I was a scholar at King's doing law. It was quite a credible career path that I was on.

Dude, I had to make it work. There was no option. I'd burnt the boats. I'd left university. I was going to have to go and work in a pub or be a waiter if I didn't make this podcast work.

Well, it must have been a big moment to leave—that decision to leave.

It was. I remember very much, I got a call from a sponsor and they said, “We want to sponsor the show.”

How much was it?

And I said, “How much is it?” They said, “It's $100,000.” They were like, “Fantastic. Send us over the paperwork.” I didn't know what the paperwork meant.

And there was no AI then either, you know.

Yeah. But it goes to our point on the valueless nature of university.

Yeah.

I just Googled contracts, and I built my own contract by Googling. That's what I used for this $100,000. But I went to my law professor and I said, “How much do you earn a year?” He said, “$82,000.” And I thought, “Okay. Well, that's my answer.”

There you go, yeah.

So I called up my parents and I said, “I'm leaving university, and this is following my dream.”

You did another clever thing there that I want people to learn, which is that you can mitigate the risk of starting by getting 1 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. Then you know you've got a customer if you commit to doing it.

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.”

Yeah.

And they're like, “Wow, we'd pay you $30,000 for that.”

Right.

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

100%, yeah. 100%.

Big one.

So, number 4.

I think the biggest challenge is when you don't know what to do. I have 1 framework for when I have tough decisions. Think of someone who you deeply respect and admire, and whose life you would want.

For me, it's Pat Grady at Sequoia. Three reasons: great father, great investor, great husband. Whenever I'm faced with a tough decision, I ask, “What would Pat do in this case?”

It generally always leads me to make the right and honorable decision when I might have otherwise made a different decision.

Got it. Number 5, what?

I think a big problem that young people have today is, “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 even outcomes. When you enjoy the art of doing, the money is the output.

I remember, to be fair, when I made my first million, I was very lonely. I remember sitting on my balcony in Fulham, where I lived, with a bottle of tequila and a packet of cigarettes. I thought I could buy any table in any club. The only challenge was, “Simon, I don't have any friends to bring to that table.”

I looked at my bank balance, which had a million in it, 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 this glorious—” I was very unhappy at that moment.

It taught me something really important, actually, which is to ask yourself a very simple question: What truly makes you happy in life? What truly makes you happy?

For me, it's walking around Hyde Park with my mother and getting an espresso. The espressos are £2.80, so for a good £5.60 you'll be good to go on your 2 espressos. That is my happiest moment. Period. So £5.60 is my happiness.

Okay, that's good to know.

I think that digging deep into yourself to understand what makes you happy is a really powerful point. I like building. I like having a mission.

I also always think about the audience sitting listening to 2 people who have money and have made money. A lot of my audience haven't made money yet. Hearing that whole point about money, you've said 2 different things: one earlier about how money does bring happiness, which it totally does. I completely agree. But also how money in itself is not enough.

Yeah.

Right?

It's like, don't chase it.

Don't chase it. I think the nuance of this that, again, I don't want anyone to miss is that you've got to have a center, right? I see your post about you going to see your mum. You always do it.

Yeah.

Because you know that's your happy place.

Yeah.

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, right?

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

Really?

Yeah. “Why do you do them? Why do you do them? Why do you do them?”

Please block those people.

And do you know what I find so funny? I also get 50 or 60 or 70 people who are like, “I called my mum today to tell her that I loved her.”

Yeah.

“And she was so happy because of that.” That's why I do it.

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

That's the amazing thing with content, though: people can build a relationship with you when they've never met you before. I have so many of the biggest CIOs of the biggest institutions in the world who will come onto 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?” It's a great way to pre-sell, to have content as your relationship builder at scale.

True. I was going to say that earlier when you were talking about having a mentor.

Yeah.

You don't necessarily need to have someone who's going to sit down with you every day. You can literally see someone whose life you like. They've got, as you say, a good marriage, a good business, and good ethics. You can just follow their content.

Yeah.

You can make them your mentor without them even realizing it.

100%.

People don't realize that, though. A lot of the 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. Feel free to follow me and see what's going on.”

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.

Yeah, I agree. It's almost like dating: the best way to attract your partner is to work on yourself—

Right.

—and make yourself someone that people would want to be partnered with.

Yeah.

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

Mm.

Or mentor.

Yeah. What I like as well is the line, “I only hire people that I would work for.”

Right.

So then it's a two-way street of learning as well, right?

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

Yeah. Well, that's the thing. 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.

As someone who doesn't want to work for someone, a lot of these people wouldn't traditionally work for someone.

Yeah.

I think if you have a similar mission, it's the whole, “I'd rather have 5% of Facebook than 100% of MySpace.” Right? There's something also in the whole balancing act. You just have to let people have their own space, I guess, their own areas as entrepreneurs.

Totally. But also, the biggest way to make money as a young person is just to work harder than anyone else.

True.

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.

Mm.

Most young people—and this is the truth that will make me unpopular—most people say they want to make money, and most people say they want to be successful. You don't understand the commitment. It's every weekend.

Mm.

It is absolutely relentless.

Mm.

Most people say they want it, but they actually don't want what it takes.

I saw a post from you a little while ago where you worked every Sunday for 12 years or something like that.

Yeah, I have done.

I think the thing is, again, it links back to how all this stuff links together. If you enjoy it, you won't call it work. Work's a weird word. To some people, the word work is a very negative thing: “I've got to go to work.” To me, I love work. I've always loved work.

I've only ever done work since I was 17. I don't like holidays, and people are like, “Oh, it's because you're a hustle-culture bro.”

Yeah.

The honest truth is I really struggle on holidays because I'm forced not to be at work.

Yeah.

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.

True.

It's very uncomfortable.

Talking about holidays, behind the scenes, folks, before we sat down here together, Harry was sitting with Phoebe Gates, Bill Gates’ daughter, and doing a podcast. I went to New York on holiday and then ended up meeting her and doing a podcast together. That's my ideal holiday, to be honest.

Right.

Go to a city, see it, meet great people, do cool stuff, and make content that helps people. That is a holiday. But to most people, it's, “Didn't you have any time off?” I'm like, “Yeah, I went to New York.”

I totally agree. My business partner always correctly tells me that life is like a cooker in a kitchen. There are 4 hobs that you turn on. There's family, friends, work, and fitness.

Mm-hmm.

Family, friends, work, and fitness. The trouble is, you can only keep 2 on at the same time.

Mm.

So I've got a hack for you. I hired my family. My mom and my brother work for me. Fitness, I always hold true. I work with my best friends and my partners in my business. So 4 become 2.

100%.

And then I keep the work.

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

You know, another big problem that young people face is they think that you have to have innovative ideas.

Mm.

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.

Mm-hmm.

“Ooh, I love that cafe, but I've always wondered why they don't do really Instagrammable cakes.” The coffee's great, and the location's great. Making something 10 or 20% better can very often create a great, successful business.

Mm.

You reinvented the VC model thinking that way, to be honest. 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—

100%.

—because no one was doing that.

Distribution.

Yeah.

No one was doing it.

Yeah.

It's the power of being first.

Yeah. I just think that people, if you look at brands like Liquid Death, are reinventing the 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 and I'm reinventing it. It's not a genius idea, is it? Education in general wasn't a new thing, was it?

I would say you're a great example, though, of innovative content. A big problem that I see with a lot of people making content is they're like, “I'm going to do 1-on-1 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 up to people on the street and say, “What's your dream?”

Mm.

I'm like, “Fuck, I'm in.” What's this? People need to be a lot more creative around the content that they create and not just copy what works.

That's true. But back to a point earlier, it's an iteration. I started out with a typical podcast, and then I went into the street eventually. I originally said, “What business would you start?” Which isn't a great hook, is it? And I realized that wasn't quite working.

It wasn't like I was a genius and sat there one day with this big, massive plan. I just literally executed every day until it got better and better. That's the part of it.

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.

My dear friend is the CEO of Spotify, Gustav Söderström, and he says, “The details are not the details. They are the product.”

Mm. I love that. All this stuff could be on T-shirts. Let's finish up our list. Number 6. Number 6.

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 new ones.

So true. I'm trying to fix the education system, and I'm making 1 TikTok a day to make that happen.

Fantastic.

That's it.

But if I said to you, “You're going to shift a trillion dollars of education spend,” you're like, “Well, Jesus. Okay.”

It's in 6 years. Next year, I'm doing that.

That's—

But this year, I'm just making 1 TikTok a day that helps people learn business.

100%.

So, number 7?

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

Yes, I have. Yeah.

There's a scene with Albert Brennaman where he's trying to woo the woman he's chasing, and the lesson is always: make the best friend like you.

Mm.

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.

Mm.

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.

Mm.

'Cause the power of the car journey home is what dictates what Simon actually does.

That's actually so true.

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."

Mm.

"He was really great."

Mm.

"So I'd spend more time with him, Simon."

Mm.

You're like, "Hmm, interesting."

I think that, again, 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 and what was going on there.

The guy who picked us up at the airport, I originally thought, "Oh, he's their driver just picking us up." So he picks us up, we go to the hotel lobby, and he's literally opening the door for me like a chauffeur. Then he helps me to the counter and tells the person, "Simon Squibb's here," and signs all these documents.

I really liked him, so I was just genuinely being nice to him. Anyway, it turns out he's Will Smith's right-hand man, and he's connected to all these celebrities. He was being really humble with me at the airport, with the sign saying "Simon Squibb," and opening the door. This guy's so connected, and I didn't realize he was this connected until 3 days into the trip.

At the end of the trip, he said, "Oh, Simon, connect on Instagram." He gave me his Instagram, and suddenly I saw all these friends and all these relationships he's got. I was so pleased with myself that I'm genuinely trying to be nice to everybody. I'm not treating the person who I think is my chauffeur badly. People make that mistake. You just never know. Always be polite, people.

The single biggest way to increase your happiness is to ask for 2 people's names. For me, it's the barista in my favorite coffee shop and the receptionist in my gym.

Mm.

Two people you have the highest frequency of contact with on a daily—

Mm.

'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. The next day, "Amy, how are you?" "Oh, I'm good, Harry. How are you?"

Mm.

You will increase happiness so significantly with those 2 little changes.

I think, to conclude, I'm gonna call you my patient zero over What's Your Dream. 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. You're super smart.

Dude, thank you so much for having me. Really appreciate it.

Appreciate you.