#416: From High School Dropout To Multi-millionaire: Transcend The Limits Of Failure to Find Success with Steven Bartlett Top Podcaster, Entrepreneur, CEO, & Investor
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When I started podcasting, an online store was the furthest thing from my mind. Now I'm selling my group coaching on the regular and it is just so easy all because I use Shopify.

The most important jobs anyone has as an entrepreneur is persuading exceptional people to leave whatever they're doing now and get on your ship. If you can do that, you will be successful. That's what I've come to learn. I used to think my success would be the byproduct of my good ideas and my hard work. I was wrong. My success is a...

Result of three things. Hiring exceptional people, binding them with a culture that gets the best out of them, and setting them a mission that is valuable and worthwhile. That is my job as a founder. Come on this journey with me. Each week when you join me, we are going to chase down our goals, overcome adversity, and set you up for a better tomorrow. That's in your

I'm ready for my close-up. Hi, and welcome back. I'm so glad you're back here with me this week. Okay, this is a super exciting episode. Wait, I'm so excited about it because this was a huge deal. As you know, I was out in Saudi Arabia in March and had the most incredible opportunity. I was brought in to do a keynote, but once they hired me for the keynote, I started getting all these requests asking if I would interview people live on stage, talk to them,

totally unexpected. And one of the teams that reached out to me was Stephen Bartlett's team. If you don't know Stephen Bartlett, he is the host of one of the biggest podcasts in the world, Diary of a CEO. He interviews literally the most brilliant minds on the planet each week. He's a stud. I mean, the guy is incredible, super confident. He's killing it. When I was on my flight on British Airways, flying from London to Riyadh,

He comes on the airline. Like he's the spokesperson for British Airways. Like the guy is everywhere. He's literally one of the biggest celebrities in Europe. If you don't know him, you got to check him out. He has millions of followers on social media. He's killing the game. And one of the things I realized interviewing him, a couple of things.

Number one, he's confident for days. Number two, he surrounds himself with the most incredible people. His team is second to none, unmatched. They're incredible, literally, from soup to nuts. And then three, he interviews and studies people all day long that are the places he wants to go, like Jeff Bezos, right? Richard Branson. Like, he...

studies the most successful people in the world and he takes direction from them. And you'll hear in this interview, he's gonna tell you exactly how to create success the way he has, but really it boils down to this. He's looking at people who have what he wants, he's studying their every moves, he's like memorizing it and he's duplicating it.

And that's kind of the understanding I took away from meeting with him. Now, he's a lot younger than me, not married, doesn't have kids, right? Like he's a very different life than I do. So you will hear that I don't necessarily see eye to eye with him on the way he talks about relationships, but that's okay. He actually made a really good point. Whether you like what he says or you don't, it doesn't really matter. It's just about...

It's about the uncomfortable. It's about innovation is about moving away from what you know. And that's always going to be uncomfortable and it's going to feel difficult and it might not sound right as the way it used to be. He's kind of challenging myself.

myself, you, all of us to think differently and to live in that space of the uncomfortable, to appreciate and celebrate failure because that's where the wins happen. And I mean, the guy's living it. It works. His philosophies work. It might rub you the wrong way. It might not. You might just get it. But for me, when it came to relationships, that was the only time I was like, oh, that's a tough one to swallow. But now that I rewatched the interview, he's right. It's

kind of bizarre. When I was in it, though, I was highly emotional. I was like, what? I was giving him a crazy look like, what are you talking about? Let's see what you think. But one other random lesson that I came out of this whole situation with, back in 2019, I interviewed Sarah Blakely for a sales conference in Boston. The man that managed that whole event was from London. His name's Dom. And the takeaways I want you to have this,

always treat people well, always close the loop, always follow up, like do your best job and treat people nicely. You never know when they're going to pop back up in your life. Wouldn't you know, totally unbeknownst to me, Dom, who I met in Boston in 2019, worked with him. Luckily, we had a great working relationship. Things went great in Boston. We closed the loop. We had each other's contact info and we did a great job. Shook hands, you know, have a nice life. Didn't think I'd see him again.

Guess who is now Stephen Bartlett's agent? Dom from Boston, right? So it's the same person. And I didn't know that until 24 hours before we were going on stage. I got a WhatsApp from him and he said, Heather Monahan, you're not going to believe this. You met me and worked with me in 2019. I'm so excited. I'm working with you again this week. I am managing Stephen Bartlett's team.

And it was just such a cool reminder to me. You never know. Don't burn a bridge. You never know where someone's going to be next. You never know. You could be working with them in a totally different capacity, unbeknownst to you, four or five years later, just like I was. So treat people well. Close the loop. Always show up and do the next right thing and be open-minded. That person could come back into your life when you least expect it.

And it definitely made me feel more confident knowing I was going to work the next day with someone I had worked with before that I did have a good working relationship with that I knew trusted me. And it set me off with a little spring in my step knowing like I'm set up for success.

When I started podcasting, an online store was the furthest thing from my mind. Now I'm selling all my digital courses and coaching on Shopify. It's so easy all because I use Shopify.

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That's code confidence15 at checkout. So one of the things I wanted to mention about Steven, which is very different when I interview the biggest celebrities in the world, many times, and I'm not going to name names, but many times those people are very strict or their teams are very strict about you can't go off script. That I have seen happen many times with interviews, with speaking engagements, with

And I don't necessarily love that, right? Like, cause I think the magic happens when you're off script, when you're just being yourself and conversations happen. However, a lot of people don't like that. They want more control. This is what's cool about Stephen Bartlett. And this does not happen when you deal with A-list celebrities in my experience.

there's only a handful of them that I've had. Actually, Jesse Itzler was the same way. I think of him as an A-list celebrity and he's like, yeah, I don't need anything scripted. Let's go. Let's wing it. I love that. That takes ultra confidence and just a belief and a knowing that you're fine in your own skin and that you trust yourself.

So Stephen's team asked me to put together a list of questions, which of course I did. And why that makes sense is you want to do a great job for the audience. You want to make sure you're delivering on what they were asking for. So it makes sense to think these things through ahead of time. So I put together a document. I put together a list of potential questions. And then I asked, would you be okay going off script? Or would you like me to adhere to exactly what is written down? You know, just give me clarity what works for you. I would prefer to be able to go off script if you're okay with it.

They came right back and said, absolutely. Steven's fine with going off script. Never has a problem with it. Totally go off script. But we like the questions you put together. And if it takes a different turn, it takes a different turn. Have a great time. And so it was so cool. That just says to me, ultra confidence, ultra belief in self. And we did go a little off script. And it was definitely the funniest part of the talk. But he was incredible. And oh, unbeknownst to everyone, we did not know, an alarm went off.

halfway through the interview or like a quarter of the way into the interview. And those are the situations you can't plan for, you can't prepare for. And I remember thinking, do we stop? Do we pause? We just kind of both leaned in and got louder and it worked. So you let me know what you think. I can't wait for you to hear his interview. He is an incredible human. I had such a blast and I think he will too. So let me know what you think of this episode. Here is my friend, Stephen Bartlett.

Assalamu alaikum, Riyadh. Thank you so much for having us today. Who's so excited to see Stephen here with us? Hello!

All right, thank you. I'm glad we're awake. We are really excited to be here. Stephen, thanks for making the trip in. Thank you for having me again. So good to be back and to see Leap is getting bigger and better every year. It's incredible this year and thank you to everyone for being here. All right, I know you guys want to hear from Stephen. You want to hear what it takes to be an incredible entrepreneur. Social media branding as well, I heard, is a big interest.

So I thought it would be interesting to start with hearing how did you become an entrepreneur? For people who see you right now as so incredibly successful, it seems like it was easy.

I think, and I've done a lot of research on this, you can correlate someone's success in life to one metric more than others, and that metric is their personal and professional failure rate. If you want to increase your chance of success, you basically have to increase your rate of failure. And I've studied many a great entrepreneur from Jeff Bezos to Thomas Watson from IBM to entrepreneurs that I know and have interviewed like the founder of Airbnb and Daniel Ek, who's a good friend of mine, the founder of Spotify.

What they all share in common is they understand that failure is feedback and feedback is knowledge and knowledge is power. So when I think about my own life and I reflect on my own failings or my own experimentation rate, leaving school at 16 years old, quitting university after one lecture, starting a company and resigning after two years, starting another business and resigning after five years, I have a very fast rate of experimentation. And that means that I think I've managed to acquire a lot of information very quickly.

And that's reflected in the companies that I build. So, in the companies that I build now, we have a head of failure. We have a head of experimentation. And I think there's probably some background context I need to give you here, which is the world is going to change at such a quick rate. You'll see this when you walk around here and you get to see some of the technology, that your question as an individual, but also as a company should be, how am I going to acquire information quickly? And how am I going to acquire valuable information quickly? It's not going to come from books.

If you listen to the futurists, they'll tell you that in the 21st century we'll experience a rate of change that is 20,000 times the previous century. So the way that you acquire information, whether you're an individual or a company, is you increase your rate of experimentation. You conduct more experiments. And so for something that's easy to understand, like a podcast, that

That means we conduct 30 or 40 experiments every week on everything, on the title, the length of the title, different colors, adding an exclamation mark, adding quotation marks, the temperature of the room, the amount of CO2 in the room when you do an interview. We take this absolute scientific approach to finding the answer, which is accelerating your rate of failure. And if you speak to Jeff Bezos, the founder of Amazon, he'll tell you the same thing. He says, "Amazon has to be the best place on earth to fail."

Nine of those failures will end up in the graveyard. But the one that is successful, the AWS, will pay for the entire graveyard. And the world we're moving into, it's going to be increasingly more important that your team is set up to conduct fast experiments. So that's, I think my life is that. Your business gets to a certain size and the cracks start to emerge. Things you used to do in a day are taking a week.

week. You have too many manual processes. You don't have one source of truth. If this is you, you should know these three numbers, 37,025, one.

Thank you.

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Anybody else out there struggle with failure? Like have a hard time bouncing back from failure? This guy over here, I feel you. I feel you, right? It sounds hard what he's talking about. So what's the key? How do you propel yourself? So there's actually some research that was done on failure that's really interesting. A researcher called Professor Wong, he looked at a database of 700,000 people that had applied for a grant.

a database of 55,000 entrepreneurs that had tried to raise investment, and another database of about 200,000 people.

And he looked at all of those people that had failed and he concluded two things. One, it does matter how much you fail. So it's important for you to increase your rate of experimentation. But the more important thing that he concluded from all of these almost about a million people and their failings was the people that learned from the failure went on to success.

So if you fail and you don't basically conduct an autopsy to learn from it, it doesn't improve your chance of success. It's not a case of just failing all the time. The key thing these researchers learned is what have you learned from the failing?

And people that don't learn from a failing, it doesn't matter how much they fail. And that's a key thing. So part of our systems and our companies is we literally have an individual called Grace Miller whose job is to teach us what we learned from the experiment we conducted, whether it succeeds or fails.

So yeah. A post-moratorium in business done very often. You just explained my personal life when you talked about not learning from failure. Anybody else? Okay, thank you. Do you apply this back to your personal life? Yes. So the way that I apply this to my personal life, my romantic relationships, is you should assume that the world has changed, right, in the last two months, three months, five months, six months.

So that the answers to how to set up a personal relationship, a romantic relationship with my girlfriend, maybe they have also changed. Which means maybe...

With all the dynamics of the modern world, maybe marriage isn't the right thing. Maybe, and I'm going to get into this particular point, with the way that the world has changed, maybe it no longer makes sense for you and your partner to sleep in the same bedroom every night. Let me explain. Okay, let me explain this particular point because this one's contentious. If you go back to first principles about sleep, you'll understand that most of our restorative sleep happens at the end of the night. So if someone wakes you up at 4 a.m. in the night,

You haven't yet got your restorative sleep. So if my girlfriend is leaving at 4 a.m., she should sleep in a different room because she's going to wake me up before I get my restorative sleep. Now convention goes, he doesn't love me.

Convention shows up and says, he doesn't love me. But if you're reasoning from first principles and you're really like conducting your own experiments to find your own answers, you go, actually, it's better for both of us and this relationship if we sleep in separate rooms, if one of us has to wake up early. It's the same thinking. It's what we call first principle thinking. You get rid of convention. You assume there's a new set of answers and there are better set of answers for your business, for your life, for your situation. And you reason up

from what you know to be true. This is how innovation happens. Innovation is the hard work of forgetting how things used to happen and asking yourself, what are the first principles of the situation and problem that I'm facing? This is what Elon Musk did with Tesla. Everyone said you can't have an affordable, fast electric car, right? Because the batteries cost this much and the car can go this fast. What Elon Musk said is okay, forget all of that,

"What is a battery made out of?" And they say, "Okay, copper, coal, zinc." He goes, "Okay, what if I bought zinc on the metal exchange in London? How much would that cost?" This is someone reasoning up from first principles. From that, he found out that the world had changed and there's actually a way to make cheaper, faster, more affordable electric cars.

But most of us are burdened and encumbered by the way things have always been done. It takes a very special type of person to be in any kind of situation, professional or personal, and go, "We're going to think for ourselves here, and we're going to run our own experiments to find our own answers." And when you consider the rate of change in the world,

The people that are able to find their own answers to new sets of problems by doing exactly what I've said, increasing their rate of failure, are those that are going to own the future. The correct answer is going to be changing faster than ever. Like the correct answer to being a lawyer now, since the implementation of things like large language models and ChatGPT, the correct answer has changed.

And when ChatGPT-5 comes out, for example, the correct answer for being an accountant is going to change again. And I'm an author. I write books. People buy the books. I could get so romantic about what I do because of the cognitive dissonance of something threatening my identity that I might ignore AI completely and I might carry on with my conventional approach to writing books and then I'll find myself in the graveyard in not a long time.

You know, this is maybe a separate point because there's two types of people when change happens and when I'm saying everything I'm saying now. And I can almost see from your facial expressions what kind of people you are because some of you are troubled by all the things that I'm saying. And the facial expression is actually a manifestation of your own cognitive dissonance, cognitive

Cognitive dissonance is this term from this psychologist Leon Festinger, where something that you're experiencing or hearing is threatening you or it's clashing with what you already know. So what the brain likes to do to make sense of the world is dismiss what it's hearing. It likes to justify it away. So when you start hearing about AI is going to take my job and this blockchain thing that the CEO of Animoca Brands was just talking about, and even when I started my first social media company, what

What people like to do is they just dismiss it to alleviate the dissonance. If you're a smoker and I told you smoking's bad for your health, the first sentence out of your mouth will be an attempt to alleviate the cognitive discomfort. You will say, "Yes, but it helps me with stress." That's cognitive dissonance at play.

There's two types of people. The lean out people who experience that dissonance and the lean in people who experience something that sounds bizarre, like AI or Web3, and they lean into the dissonance. The future is going to be owned by people that are capable of hearing something really strange and leaning into the dissonance.

Web3 was the same for me. I heard people were buying NFTs on the internet that were monkey pictures and pictures of rocks for hundreds of thousands of pounds. It sounded really, really bizarre. For about two or three weeks, I criticized them. I thought they're weirdos, they're idiots, this is a Ponzi scheme. And then I remembered that this is the exact reaction people had to me in 2010 when I tried to get them to join social media and I launched my social media company. So what I did...

is I leaned into the dissonance. I bought one of those monkey pictures for a quarter of a million dollars, right? It's worth very little now, but that's not the point. The point was it taught me about technology. I started a company called Third Web. The company's raised $31 million. It's worth $160 million. It actually works with Animoca Brands. He was just on stage now.

big team in San Francisco of 50 people, I leaned into something that felt bizarre. If I had kids now, I wouldn't be trying to teach them about any particular subject. I'd be trying to give them a mentality towards change. How do we deal with dissonance, change, threats? Are we ostriches? Do we bury our heads in the sand? Or are we lean in people?

I would be telling my kid, when something sounds strange and you feel threatened by it, lean in. Run some experiments. Don't lean out. So, yeah. I love the romantic advice. Thank you. Let's try that. Okay. Now, one of the things that's so interesting about you, and many of you may only see him in one capacity, an author, a podcast host, owning a social media company, but you're doing so many things. How do

other entrepreneurs know when is it right to just focus on one thing versus diversify? Yeah, so in our portfolio, so Flight Group is our holding company. We have 41 different companies and I'd say we have significant operational involvement in about five of them, but there's 41 in total. Some of them are more passive investments. Some of them we might have a 20 or 30% stake in and then some of them we have a majority position in. The key thing to answer your question is

A company by definition of the word is group of people. So for me, when I got to the point in my life where I had the

leverage the resources to hire exceptional people and delegate, that's when I knew I could do more than one thing. And Richard Branson, who I met in New York and I went to an event with him and then I interviewed him for a couple of hours, is the absolute master of this. He said to me, because he's dyslexic, so he struggles with reading, and he's not particularly good at maths, in his own words, he said to me, I've always had to ask who, not how.

And this is like, my girlfriend started a business. It does like breath work and meditation. And I remember walking in the front room and watching her for seven hours try and figure out how to build a website. And that for me is almost a metaphor from what I see from entrepreneurs. They spend so much time, they waste so much time doing things that they are not good at. What Richard Branson taught me is business is about

effective delegation. Richard Branson, in his 50s, ran one of the biggest groups in Europe, right? And he told me about a meeting he had, at 50 years old, runs one of the biggest groups in Europe, where he sat in the meeting and his CFO says, Richard, do you know what's going on? He goes, he's like, no. His CFO takes him out of the room, draws a picture of an ocean,

and then draws a picture of a net in the ocean, and then puts some fishies in the net, and goes, "Richard, this is what net profit is. Net profit is the fishies here in the net." At this point, Richard is running one of the biggest groups in Europe, and he doesn't know what net profit is.

because he's been such a good delegator for his entire career that he doesn't really need to know a bunch of stuff. He's so good at finding people and giving them responsibility. In this season of my life, that is what I'm doing. I'm finding exceptional individuals

I'm spending about 20 hours a week of my time on recruitment and I'm empowering them to start companies. Again, I've researched this really, really deeply. I've interviewed Walter Isaacson who followed Elon Musk for two years and he followed Steve Jobs pretty much until the day he died. And I asked him, I said, what's their secret? He said, specifically in the case of Steve Jobs,

He said, "You know, Steve, I was in the backyard with Steve Jobs before he died, and I asked him a question. I said, 'What's the best product you ever built at Apple?' Steve turned to me and went, 'Vatine.'

He goes, "That's the most important thing." He goes, "The iPhone's great, the Mac is great, but the best product I ever made at Apple was the team." By definition of the word company is group of people. And if you play out this thought experiment, if any of you had managed to hire Elon Musk and get the best out of him, you would be the benefactor of trillions of dollars. So I think through that lens, my job is to find the next A player.

And that's why I went from spending one hour a week of my time on hiring and recruitment. Now I spend 20 hours of my week. All of you, both personally and professionally, are in the recruitment business. It is going to be the single biggest defining factor of where you end up personally and professionally. I can run you through the research on the personal part about, you know, if you choose the right partner in life, the impact it has on your income, health,

happiness, but on the professional side of things, nothing is gonna determine where you end up more than your ability to recruit great people, nothing. I look at my family office,

I look at the value of my family office. I reverse engineer where that value came from. Less than 10 people are responsible for 80% of the value of that family office. A players. And with that in mind, it became very logically clear to me that I should be spending a huge amount of my time hunting for A players. Last point on this. When you're young and you're starting out in business or you're young in business, i.e. you're new,

What you're going to be saying to me is, Steve, but these people don't want to come and work at my company. Or the second rebuttal is, I can't afford them. The great thing about A players is they return disproportionately more than a B player. It might have to pay them £100,000. The return in my business will be £10 million. And the second point is the chicken and egg thing, which is, you know, we knew why would they come and work here? Your job...

the most important jobs anyone has as an entrepreneur is persuading exceptional people to leave whatever they're doing now and get on your ship. If you can do that, you will be successful. That's what I've come to learn. I used to think my success would be the byproduct of my good ideas and my hard work. I was wrong.

My success is a result of three things. Hiring exceptional people, binding them with a culture that gets the best out of them, and setting them a mission that is valuable and worthwhile. That is my job as a founder.

If you're like me, then you are getting so hyped for fall dressing now that fall is right around the corner. I'm so thrilled to hear from one of our favorite sponsors, Jenny Kane. They are the experts in classic elevated wardrobe essentials, especially iconic and super luxe sweaters. Jenny Kane is a California brand through and through, and their staples make getting dressed easy.

Effortless. Think minimalist and refined with pieces like cozy cashmere sweaters and noteworthy accessories to elevate versions of your everyday basics. Jenny Kane has everything you need to take the guesswork out of getting dressed, not to mention the most incredible home essentials, too. Their sweaters are the quintessential must-have item, and I'm eagerly stocking up on all their transitional knits and fall-ready basics like the cashmere cocoon cardigan. The cocoon is the perfect cardigan. It's oversized, super soft, and goes without.

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- He is speaking truth. He is surrounded by the best people over there. Just wanted to add that. We are down to the last two minutes. We've got to rapid fire some questions so you guys can get as much knowledge from Stephen as possible. What big regret do you have? - The big professional regret I have is

Knowing that someone was wrong for my company or team and taking too long to make a decision about it. Because, again, I wrote about some of the research in my book, but the impact that a negative member of your team has is three to four times the positive impact a good member of your team has. And a nice thought experiment for you guys to think about when you're trying to understand if an existing member of your team is good or not.

or when you're hiring someone and you're trying to figure out if they're a good team member, is ask yourself this question: If everyone in the team was like them in terms of attitude, cultural values, i.e. alignment with the company culture, would the overall average be raised, maintained, or lowered?

Both me and both Amazon have a policy which we call bar raisers. Every single person that we hire should raise the bar. They should raise the average. Now think about one person you work with professionally.

And ask yourself the question, if everyone in your company was like them in terms of attitude and cultural values, I'm not saying lived experience, we need diversity, attitude and cultural values, would the average be raised, maintained or lowered? If it would be lowered considerably, you should get rid of that individual. If it would be maintained, maybe that's a case to train the individual. If it would be raised, that's the type of individual you need to promote.

Because companies don't have one culture. They typically have as many cultures as they have managers. So in my previous business, we probably had about 30 or 40 managers and we had 30 or 40 cultures, really. Because I remember one day speaking to Jason's team and they're all so happy. Best company they've ever worked for. Then I spoke to a team that sat next to Jason's team and they're all on their way out the door. They're about to quit.

So you want your best people, the real sort of cultural disciples, as high as you possibly can in the organization. And that's what we call the bar raiser test.

Okay, final question. What big learning or takeaway have you personally taken from your podcast? Maybe the biggest one is just this focus on expectations. So Mo Gordat, who's speaking here, he's a friend of mine. He said, we're happy when our expectations of how our life is supposed to be going are met. And we're unhappy when our expectations of how our life is supposed to be going are unmet. And from this, you understand why...

Back in Botswana where I was born, you know, my mother getting a hot bowl of jollof rice makes her unbelievably happy because her expectations are being met or exceeded. But if you go to Mayfair in London now and you see a billionaire's steak come medium rare, but they ask for medium, anger. The whole of life as it relates to happiness, most of it comes down to whether your expectations are being met, exceeded or unmet. And this is when someone cuts you off in the car in the morning. You know,

You know, I flew here on a nice flight, it's first class, whatever. I'm probably used to that now. It's probably having a lot less impact on me. But seven years ago was the first time I got on a plane as an adult and I flew in economy. I was way happier in economy that first flight to Thailand. I couldn't believe my eyes. We're in a tin can and we're going to try and fly this tin can across the world. I was, I couldn't believe it.

My expectations were being exceeded. Now on the flight over here, my expectations are no longer being exceeded. So the reaction's different. You can think about relationships, team members, pay rises, promotions, your wife or husband through the exact same lens of expectations. Are expectations being met? Are they being exceeded? Are they falling short? That's how you understand why people are happy typically and why they're not. Just figure out what their expectations were in any situation.

Stephen, you're incredible. I know nobody wants us over, but they're flashing at us. Time's up. Can we please give it up for Stephen Bartlett? Thank you so much.

What's up, everyone? I'm Hala Taha, host of Yap Young and Profiting Podcast, a top 10 entrepreneurship podcast on Apple. I'm also the CEO and founder of the Yap Media Podcast Network, the number one business and self-improvement podcast network. That's why they call me the podcast princess. On Young and Profiting Podcast, I interview the brightest minds in the world,

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