Simon Sinek: You're Being Lied To About AI's Real Purpose And We're Teaching Our Kids To Not Be Human!
Guests: Simon
Full transcript · Read the full conversation in order, with its original context.
§01Transcript — part 1
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With AI, do you think it really is cause for concern and deeper thought?
I'm not in the AI business, but I am in the humanity business. Here is the problem that we never talk about: people keep telling us life is not about the destination, life is about the journey. But when we think about AI, we only think about the destination. It has a remarkable ability to write the book, paint the painting, or solve the problem. But we forget the importance of doing the work yourself.
I think in our modern day and age, we have underrepresented the value of struggle. I am smarter, better at problem-solving, and more resourceful not because a book exists with my ideas in it, but because I wrote it. That excruciating journey is what made me grow. It’s the same for love, friendships, and conflict. I think we forget that we give up certain skills or abilities because of technology. It's like saying AI will provide boats for everyone, except for the time there's a storm and you don't know how to swim.
Unless we take personal accountability to teach and learn human skills, they will disappear. Sure, you can have an AI friend trained like the best psychologist to affirm you, with the best listening skills that exist. But my ability to know what to do when my friend is struggling, my ability to function in the world, or my ability to cope with stress—these very human skills are suffering.
So, what are the other skills we need to equip ourselves with based on the way the world is heading?
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Simon, good to see you again. Why are you laughing?
It's just familiar.
It is familiar. It’s so interesting because when I sit down to talk to you, you're one of the very few people I don't come with a preconception as to what we're going to talk about. But I come with a feeling, and the feeling I bring forth is the feeling of change and transition. I have lived for 32 years, but I don't think I can ever think of a time where the future has felt unclear, uncertain, scary, exciting, and unknown.
I don't just mean with technology, but technology is one protagonist in the story. There are many other social stories playing out from politics to relationships to all of these things. So, my first question to you, Simon, is what are those things? What are the biggest forces of change you see happening at the moment in all of our lives that you think we should probably talk about today?
That is a big question. I think one of the mistakes we make, and this is in general, is we like things to be very neatly organized. We like them to be black and white, yes or no, right or wrong. As you know, the world is messier than that; it is more nuanced than that. Nothing operates in a vacuum; everything is connected to everything.
Especially in a world filled with this rising technology called the internet and this burgeoning technology called social media, desires and feeling like belonging become more and more important. We're struggling to find them. Loneliness epidemics, stress epidemics, suicide epidemics—these are all feelings of disconnection, lack of control, and loneliness. That only exaggerates our feeling of loneliness and despair and wanting more. Then you add in AI, and now those feelings of insecurity are just exaggerated like crazy.
Now, I find AI—there's an irony to AI. If you go back to the '70s and '80s, you had the rise of robotics. Robots were coming into our factories, and we were able to cut employees by dramatic amounts. We put people out on the street who had worked in a factory, whose fathers worked in a factory, whose grandfathers worked in a factory. They said, "These robots are taking our jobs." The ruling classes, the Wall Street classes, and the CEO classes said, "Yeah, I know. Technology. You’re going to have to find a new skill. Reskill, reskill."
Flash forward to AI. Here's where the irony comes in because nature abhors a vacuum and life seeks balance at all times. Not always immediately, but it seeks balance. Flash forward to AI, and now you hear the knowledge workers. It’s the knowledge workers who are going, "My job!" It’s the coders, the finance people saying, "My job!"
The plumber is not worried about AI at all. The baggage handler at the airport cares zero about AI. So, maybe the right response is, "It's the future, man. It's technology. Reskill, reskill." Maybe become a plumber? By the way, the money is really good, and you get to work for yourself if you want. I just find the pendulum kind of funny.
With AI, do you think it's overblown or do you think it really is cause for concern and deeper thought?
The honest answer is: I don't know. Everybody falls on one side of "the sky is not falling, Chicken Little" or "the sky is falling and we're all going to die." The truth, like most things, is probably somewhere in the middle. But the real answer is I don't know, and neither does anybody else.
It seems that we should have some sort of controls because we didn't put any controls on the internet. They did put controls on the internet in China; children don't have the same access to social media like kids do here. Europe has controls on the internet, and America doesn't. We're the ones who seem to be suffering more because of the lack of controls on the internet. I think some call for reform—I mean, they make us wear seatbelts in our cars. We have speed limits. It's for the greater good. Your seatbelt's uncomfortable, but you’ll get used to it. It’s fine. I think the call for no reform is wrong; there are correct limits to keep things safe.
I am fascinated by AI, both the benefits and the weaknesses of it. But it is revealing to me something more important than what other people are talking about, which is: we are a results-obsessed society. We care about output, we care about performance, we care about numbers, we care about final product more than anything. When people talk about AI, they talk about its remarkable ability to write the symphony, paint the painting, write the book, or solve the problem.
By the way, the technology is incredible. I asked it only a few months ago to please take a text and put it in the style of me. It was fine. I did it with a friend of mine who's also an author; we both did it for ourselves and each other. It gave me a good start and I could edit it. I did it again recently, and it was damn near flawless. It was scary good.
Now, AI doesn't know the thing I'm thinking about. It doesn't know the next book I'm going to write is about friendship. It doesn't know the point of view I'm going to have on friendship. If you ask it what Simon Sinek would say about friendship, it’s going to be "why this" and "why that." So, it's derivative. We know that. It's not original. But at the end of the day, the work is good. The symphony is good, the art is good, the article is good, the book is decent. It's getting better and better.
But here's the problem that we keep not talking about. People keep telling us that life is not about the destination, life is about the journey. That’s what we keep being told. But when we think about AI, we only think about the destination. We only think about the output; we never think about the input.
I can tell you that I am smarter, better at problem-solving, more resourceful, and better at pattern recognition not because a book exists with my ideas in it, but because I wrote it. The excruciating pain of organizing ideas, putting them in a linear fashion, trying to put them in a way that other people can understand—that excruciating journey is what made me grow.
Sure, you can have an AI friend. That AI friend has been trained like the best psychologist to affirm you. "Tell me about your day. Mmm, that sounds difficult. Boy, it’s hard being you. Oh my god, it’s so great being you." It's an affirmation machine built by a for-profit company that wants you to stay on. But nobody's learning how to be a friend. It'll feel good, you’ll feel like you have a friend, but you’re not learning to *be* a friend.
What made you a great entrepreneur is not that the company exists; it's that you built it with your hands and you’ve got the scars to show for it. It was when things went wrong and you were forced to fix them and think that you became smarter. You're a much smarter businessman now than you were five or six years ago because you did it.
I am a fan of AI; I want AI to make things. But I would hate to lose out on becoming a better version of me. To really learn to grow—by the way, I used to have a steel trap for phone numbers. I knew everybody's phone number. Then all of a sudden my phone, my PDA, meant I didn't need to memorize a phone number anymore. I don't know the phone numbers of most of the people I love. I type their names in. My brain literally went on strike. It said, "Fine, you no longer have the capacity to remember phone numbers." We give up certain skills or abilities because of technology regularly. That’s fine. I don't have a problem with those things because whether I can remember a phone number or not will not affect my relationships, my ability to function in the world, or my ability to cope with stress.
But my ability to know what to do when my friend is struggling, my ability to know what to do when I have a fight with my spouse or my partner, my ability to know what to do when my boss yells at me but I don't want to escalate it, or my employee is acting out and I don't want to fire them—how do I resolve this? If I've missed out on those skills and simply ask AI, "How should I resolve this?" it'll give you an answer and it may work, but you've learned nothing.
It's like saying AI will provide boats for everyone, except for the time there's a storm and you don't know how to swim. I'm okay using the boat, but also learn how to swim. I think there's something to be said for writing your own symphony, painting your own painting, building your own business, or writing your own book—not for the output, but for your personal growth.
Before I got here today, I was writing a post for LinkedIn. I was trying to make the case that everybody using ChatGPT to write their emails, their social media posts, and their investment pitches is now making the internet feel really inauthentic. People that I've known for many, many years are now sending me these perfect cookie-cutter emails with words that I’ve never heard them use before. When I read it, my brain mentally discounts it as not being their opinion. When you feel like you're speaking to someone's AI, the meaning is gone.
I was writing about how actually now there's this premium on human-written language. If you make a couple of mistakes and you use the old words—you don't use words like "forged" and "robust." "I'd like to forge a partnership with you, Steven." I'm like, "You’ve never said that to me, mate!"
The em-dashes! It’s funny, right? It's crazy. But what you're talking about—have you ever heard of the Japanese concept of Wabi-sabi?
No.
Wabi-sabi is a Japanese design concept which is beauty in that which is temporary or imperfect. Have you ever seen Japanese ceramics? They're wonky, or the glaze is not even. They’re beautiful. You know why? Because they’re handmade. Wood is beautiful because it’s imperfect and unique. Things made on a machine are the same and less beautiful.
What makes people beautiful is not that we get everything right; it's that we get many things wrong. What makes us fall in love is not the person who's perfect; it’s the person who accepts our imperfections and we learn to accept theirs. In the art world, artists are being asked to sign affidavits that say, "I painted this. I made this, not AI." Not because it's better or worse, but because I want to know it was touched by human hands.
I think you're right. What will happen is everything will be so perfect that it'll be as if we're all using things that came off a conveyor belt. What we will start to desire is things that are made by hand. Think about a Rolls Royce or a Ferrari. It takes 39 months to get a Ferrari because it was made by hand. One of the things that makes it expensive is the technology, but the other thing is it’s slow and it was made by people.
Human error. The value of human error. Scooter Braun said to me the other day, "We could watch a computer play chess with another computer." He goes, "But the chess games that have the highest demand are one human versus another. When a computer plays a computer, the moves are predictable and they're perfect. But it's the human error of two human chess players—who are objectively worse at chess—that makes it so fascinating."
Yes! And that’s any sporting event. It's not the perfection of the game; it's the error that loses the game that adds the drama. It’s like trying not to make a mistake is as powerful as trying to get everything right. It is the imperfection, and I think that we forget as people what makes us beautiful. Like when you go on a first date or a first interview. All you do is present perfection. I put on my best clothes, I dressed up—I don't dress like this every day. For my interview, I wanted to put out a good impression. I practiced and made myself confident. Then you get in the relationship or you get the job and you become a slob. This is what AI is—to your point, it's fake.
On the interview example, the minute you started describing that, I immediately flashed back to an interview I had last week where a young kid walks in wearing a suit. I thought, "Now I have no idea who you are, because I know that's not you." I know that you don't wear a suit; you’re 22 years old. I have no clues as to who you are, and therefore it’s harder for me to figure out if you fit here. What he tried to do there was show up "perfect"—what he thought perfect was—and in some ways to hide who he actually was. This is why I like sloppy text now. I like grammatical mistakes.
But at the same time, you don't want him to show up, kick his shoes off, and put his feet on the table either. There's an element of respect you want. You want somebody in a first interview to put on some effort. Too much effort is pretty inauthentic, but too little effort? What's that?
This is my diagram: You've got "perfect" on one end, which is low value, and you've got "poor," which is also low value. The sweet spot is right here in the middle.
I think there's some truth to that. It’s the same thing as like we all want vulnerability in our relationships, but not on the first date. I don't need to know *that* quite yet.
What are the other skills that you think we need to equip ourselves with based on the way that the world is heading? Like the calculator came along and we no longer needed to be able to do complicated math—I've completely forgotten my times tables. I can't spell anymore! I said to my friends, the most I can do is nine times nine; that's like the top end of my range. With spelling, I get like half the word correct now with AI and it does the rest.
I think it’s all human skills. So, I think where the world is going to go—and at least this is where I'm taking a bet—is that as the end product becomes easier to produce, it’s the humanity that's going to suffer. Unless we take personal accountability, both as individuals and organizations, to teach and learn human skills, they will disappear for all the reasons we're talking about.
So: How do I listen? How do I hold space? How do I resolve conflict peacefully? How do I give and how do I receive feedback? Those are two different skills. How do I have an effective confrontation? "You pissed me off; do I know how to approach you as a friend or as a colleague without creating a massive fight or losing a friendship over it?" How to take accountability? How to express empathy? These skills—these very human skills—are the things that we're already starting to see are suffering with the internet and social media. AI will only exaggerate the loss of those skills, and those skills are more important than learning how to spell.
One of the concerning things was I heard Sam Altman, who's the founder of OpenAI and ChatGPT, launch this thing called Worldcoin a couple of years ago when ChatGPT really started taking off. It has been closely tied to the concept of Universal Basic Income (UBI). The idea—the overarching idea—is that in a world where AI and automation eliminate many jobs, UBI may be necessary. Worldcoin is one way to help implement it. That was stated by the founder of ChatGPT, Sam Altman.
I'll go back to my ironic statement before. Isn't it ironic that they want to do a universal income now that the *knowledge workers* are losing their jobs? But when the *factory workers* were losing their jobs, those same people were massively against these kinds of things. So, I mean, yes, it’s ironic.
What happens to purpose and meaning if we’re being—for anybody that doesn't know what Universal Basic Income is, the idea is the government, the state, whatever, would pay you a certain amount of money every single month. Like a minimum salary—two thousand, three thousand dollars, whatever it might be—because they don't think many of us are going to have—there’s not going to be enough jobs to go around. I wonder what happens to purpose and meaning and pursuit and challenge and all these things in a world where we're just being handed money?
So, we're not being given wealth; there's a difference. We're being given survival money. We have to be very careful that says everybody who's on welfare is lazy; that's not true. We have to be very careful that just because we give somebody something doesn't mean that they cease to have ambition or purpose or drive. It's like somebody who makes a commission salary; they make just enough to pay their rent and buy food, and that's it. That's a lack of ambition.
The people I've heard talk about it make a compelling case for it, especially in a world where there is plenty of wealth. But I don't know enough about it to make an argument for or against it, if I'm honest. But I do find it ironic that the Sam Altmans of the world are calling for it given the fact that there's going to be so many job losses when it's jobs of *their* kind. I also think that’s funny. What’s going to happen when Sam Altman’s product gets good enough that he can lay off most of his staff? Just curious what happens.
He has made a point of having, I think it's 100 people or less in his company. He doesn't have a big team. I think part of that is because—what I heard in his TED Talk a couple of days ago—he said, "Yeah, I think AGI (Artificial General Intelligence) is sooner than we think, actually, and I think we're going to have a fast takeoff." Which means it's going to arrive very quickly and accelerate very quickly. So I think he's actually preparing not to need a large team.
Yeah, but what happens to the 90 people he lays off when he doesn't need 100, he only needs 10? This is the question. I don't know, and this is why anybody who has an opinion about it—the answer is we don't know. But I think people react very differently when it's *their* job on the line, when it's *their* income on the line, when it's *their* pride, when it's *their* ego. I keep hearing from companies—we were talking about this before we turned on the cameras—you talk to a company if you want a new website. I guarantee you, I don't care which company you talk to, they will all talk about how they AI this and AI that. You ask the question, "Are you using AI?" "Yes, we’re using AI, we’re doing it differently, we’re the future, blah blah blah." Then you ask them for a proposal, and it’s going to look like all the other proposals from 2015. "This is how many hours it’s going to take our people to program this and code this." I’m like, "What happened to all the AI? Why is this slow and expensive when everything's supposed to be fast and inexpensive?"
Because they’re taking the margin.
Of course they’re taking the margin! And they’ve got a lot of people doing things the old-fashioned way because the business model—the status quo—exists because there are people who benefit from the status quo. That’s why there is a status quo. Everybody’s into "change the future" until it's them that's threatened, or their income.
All of the billionaires that I know, the one consistent thing they whisper to me about AI is that people are going to have a lot of free time. That’s one of the things that's been really consistent. You're so right when you say that when I asked you about the future of AI, you said, "I don't know." The reason why I know that's probably the correct answer generally is because when I sat with the most advanced people in AI—whether it's Mustafa (Suleyman) who's head of Microsoft AI, or people from Google, or Reed Hoffman who's the founder of LinkedIn—they all had different opinions. Which made me think, actually, the right answer is nobody knows.
The right answer is nobody knows. That is correct. And you always be aware of the messenger, right? Like you won't have anybody who owns an AI company talking doomsday scenarios. It's not in their economic interest, even if they secretly harbor that. It's like people who used to run cigarette companies didn't smoke and they didn't let their families smoke. I remember visiting Facebook in the earlier days and I went into the cafeteria and they had picnic benches. They were telling me with pride how they have these communal eating areas to help people maintain relationships. I was like, "This is hilarious. You literally have a product that breaks relationships, and yet you understand enough to make people eat together at lunchtime so that they'll maintain relationships." I mean, the point being, if your economic interest—show me how someone's paid and I'll show you how they behave.
One of the scariest conversations I was privy to was one—a friend of mine who’s a billionaire in London—he knows the CEO of one of the biggest AI companies in the world, who I can't name. He said, "By the way, what he tells me in private is not what he’s saying publicly." He said to me that what this particular CEO thinks is going to happen with AI is pretty horrific. And the CEO of this big AI company is totally cool with it. It’s horrific what he thinks is about to happen. Then when I watch this guy do his online talks and give his opinion, he’s so nuanced and "everything will be fine" and he's an AI optimist. Then I heard this scenario at this kitchen table in East London from his friend about what he really thinks, and it was chilling. Actually, the lack of empathy and the obsession with power was shocking to me.
That makes sense to me. The obsession with power and money and all the rest of it, yeah. But this is because the internet has done something really strange and challenged one of my theories head-on. I talk about in an infinite game, James Carse’s theory, in an infinite game there's no winners or losers. So, like, nobody "wins" fast food. Nobody "wins" cars. General Motors, Ford, Vauxhall—they can all exist at the same time. They'll have degrees of success or not success, but they can all exist simultaneously. Nobody's going to win. The exception is in the internet. Amazon—it won. Google for search—yep, they won. If you start going down the big tech companies, there is only one. I mean, sure, there's competition, but not really. Walmart is making a run of it to threaten Amazon, but Amazon's still so damn big. All of these companies—there’s only one. That's not good. You can't have winners in a category. This is why I think the race for AI dominance is so aggressive, and which is why people are not being careful and not putting controls on—because the way that tech seems to work is there probably will be one dominant standard and then that's it. And the question is which one? Because I don't think—that just seems to be the way it is. Which is a very scary prospect to me that we can have winners. It’s a bad thing, especially if we pride ourselves on being capitalists. Then there cannot be a winner. There cannot be one that is so dominant that nobody else can even compete except for scraps.
What are your emotions when you think about AI and what's happening? Because I feel like the moment we’re living in is profound and that we don't actually realize it. When these tools come out—OpenAI released yesterday 3.0, it's the best model ever—the day after my life was the same. So we don't really notice it because we go back to work, our clients ask us for the same thing, we have the same team members sat around us. It almost seems like the sand timer has been rotated and we're on a clock. It's a slow disruption of our everyday lives. Sam Altman the other day on his TED Talk said, "In the short term, everything will appear the same, but in the long term, life is going to be completely different."
I think that's right. I mean, and look at any technology like AI. It was kind of the same until it wasn't. These are evolutions, not revolutions. Like there's a revolutionary bit—I remember when the internet showed up and brick-and-mortar internet shopping showed up. All the technologists were like, "It’s the end of stores. It's the end of bricks and mortar. Done. We’ll never go to a shop again." Well, that didn't happen. Now, shops struggle to compete against the internet, but that's a price thing; that's a business model thing. But we like going shopping because, again, all of these companies always forget—especially technologists—they all forget that the end-user is a human being. Most of us don't fully understand everything. Even our iPhones—most people use a small percentage of all the capabilities of our iPhones. Most of us don't even know how to change the damn settings to make it do something we want. Neither do your kids; it's not an adult thing, it's not an old person thing. And there's a few people who get more out of it, and good for them. Some people use it just as a phone. Fine. It’s a bell curve. So I think there will be a few people and a few companies that will get more value out of these things than the rest of us. But I think he's right: there'll be a revolutionary bit and then it'll settle.
I find this whole thing fascinating. When you ask me how do I feel—depending on what subject I'm talking about—absolute fear and absolute amazement. I have both and everything in between. When I think about how it affects democracy and the ability to make deepfakes and how it can manipulate people and their opinions to vote one way or another, I have real fear.
When it comes to productivity and the reshaping of business—technologists and people who are part of the internet revolution love to say, "You know, 20 years ago, 80% of the jobs we have now didn't exist." They love to say that! But when you ask them now, they seem to think—I think it's the same, which is all those people who are going to lose those jobs in white-collar jobs and knowledge workers—they’re not going to *not* work. There's going to be new jobs. The IRS (Internal Revenue Service) digitized a whole bunch of years ago. They got rid of all the accountants and they put in all the computers. Do you know how much money the IRS saved when it completely changed the way it looked? The answer is zero. Yes, they got rid of all the accountants, but they needed to hire all the IT people.
So the workforce looked different, but it didn't get smaller. And so I think the same thing—what it’s going to—we also already know the massive, incredible amounts of energy that it takes for AI to work. Data centers that use up massive amounts of electricity like we’ve never seen in our lives. Like nuclear *has* to be a thing. There isn't enough coal or oil or solar or wind to power these things. It just doesn't exist. So nuclear *has* to be a thing. So go be a nuclear engineer. You want an advanced degree? I don't need you to be a coder; coding was a thing for a long time. Go be a nuke. Because by the way, you’ve got to be just as smart to be a nuke as you have to be a coder. So you're going to start to see that. You're going to see energy work. I just think the jobs will change. I don't think they're going to—it's not like you're going to be a bunch of people walking around bored. I just think the jobs will change.
If there was a 10-year-old kid stood here now and the 10-year-old said to us, "Guys, what do you think I should focus on?"
I would say two things. One is, going back to human skills, learn how to be a good friend to your friends.
How do I learn that?
A 10-year-old learns it when they go and have a playdate at a friend's house. A smart parent takes away all the phones—I would hate that the 10-year-old has a phone in the first place, but if they do, take away all the phones and make the kids go play. When they have a fight, the parents make them say sorry. "Go over to your friend's house and knock on the door and you're going to say sorry for the thing that you did." We're going to teach kids how to resolve conflict, how to pay compliments, how to take accountability. These are all the skills of, "What did you do wrong versus what happened?" It's not always the school or the teacher; maybe your kid *is* disruptive. Accountability is a real thing.
I think if we teach those things to 10-year-olds and to adults, it makes for a better society. The other thing is go learn a real skill. I don't mean that prompting is not a real skill; that's not what I mean. It's what I said before, which is the excruciating—what makes great relationships great is not that you get along all the time. The best marriages, the best relationships, they’re not absent of conflict; it's that they know how to resolve conflict peacefully. By the way, I believe in world peace. I don't believe in a world without conflict; I believe in a world in which we can resolve our conflict peacefully without the need to go to war to resolve conflict. This is why I like democracies, because democracies can solve conflict without bullets.
So the human skills are one. But when I say a real skill, I mean like go do something difficult. Build something, design something, imagine something, write something. And I'm totally fine even if you plug it into ChatGPT and say, "Tell me what's wrong with this. My grammar's all screwed up." Like I said, I am smarter because I *did* it. The reason I'm more confident than when I was younger—I think that's one of the things people talk about, you get wise with age, you have more confidence as you get older. Yes, that's all true and there's multiple reasons for it, but I think one of the reasons is the things that are happening to me now, I've gone through those things before. They were scary and kept me up at night the first time, and now I know how to do it. I'm not afraid of it anymore. I think what happens as you gain experience is you lose fear. And if ChatGPT or whatever AI product we use does everything for us, I think you just end up scared.
One of the things that I'm contending with at the moment, with this new technology that’s arrived, being an entrepreneur, seeing this huge opportunity, thinking about the dot-com boom and all the great opportunity that created—people talking about the age of abundance and all these things—is I'm contending with the question on a personal level, which is: when is enough enough?
Maybe this question is more pertinent now than ever in a world where creating stuff, building stuff, starting a company, launching a book—the cost of creating these things, whether they're good or not so good, has gone to basically zero. We can all theoretically, from our computers now, become movie directors and authors and software developers. With this possibility, opportunity, and the thing we need to deploy is intention—what do I do? What is the thing that's going to lead me to happiness? Do I pursue all of these things and start building and creating and running off down that path to climb some ladder, or do I take a second? When is enough enough? And as an entrepreneur who is in this moment, has a lot of resources, could roll the dice, could start all these new companies, could do all of these things—when is enough enough?
Now. Right? There's something to be said for gratitude. And if you want to make it money, we know the data on this. I think once you reach—I can't remember the number, it’s $70,000 a year of income—like when you're talking about money can't buy happiness, it absolutely buys happiness up to a certain level, which is survival and then a little bit more. But once you reach a certain level, there is no discernible increase in happiness that comes with money.
Now, what money buys is options. What money buys is time. Those things are true. And you said it: some of the people that you and I know who have made generational wealth, they’re not discernibly happy. The ones that *are* happy were happy before they made the money. And the ones who thought the money would buy them happiness, or worse, the money took away their purpose because when they made the money they were driven by something that they accidentally made the money. They built businesses that were their passions and their cause, and then the money came and they weren't building the thing anymore.
This is the difference—it’s really interesting. It also gets to the question of why is it that small companies are more innovative than big companies? You think about it: when you say what’s the secret for innovation, well you want to have resources, you want to have great people, and you want to have great market opportunities and then you can have great ideas. Okay, so big companies have tons of money, they have all the best people, they have mature marketplaces where people generally know who they are, and they’re the least innovative organizations on the planet. Then you have little companies that have no money, they’re bootstrapping it, they don't have enough people, nobody knows who they are, and there are shit market conditions, and yet they *are* more innovative. And then big companies innovate by buying the little companies.
Why is that? Why is that the rule? I think the reason is because when you're small, your ambitions are bigger than the resources you have to achieve those ambitions. Every small business has outsized ambitions, objectively stupid. You look at what they have and what they’ve got and they tell you where they're going to be and you're just like, "No." And yet some of them do. I think the problem with big companies is their ambitions are well within their capabilities and their resources. In other words, their vision isn't big enough.
I think your vision has to be bigger than the amount of money, resources, and intelligence that you have to achieve that, and what that produces is creativity. If we can do so much with AI, then we need bigger visions. So when you ask me how do you find happiness, I think that we need to set our sights on things that are bigger than finite success. I think we do need a gratitude practice. Regardless of how little or how much you have, to be grateful for what you do have is a profound impact.
I went through this with the LA fires. I was very lucky that my house survived and I didn't have to get evacuated, but the evacuation zones were getting closer and closer. Two things happened that were profound that live with me now, one which is resolvable and one which is unresolvable. We were all obsessed with this app called Watch Duty, which is how we tracked the fires. It basically took all the publicly available information and put it in one place in a really amazing way. We were all on this app the whole time, and one of the things we were watching was the wind. If the wind shifted, it could profoundly impact your life.
I remember having this experience: we were all watching the wind, and the wind went away from me. I thought, "Oh, thank God." And in that moment I knew that somebody was looking at the app going, "Oh god, no." And it's not like service where I'll eat a little less so that somebody can eat more. I don't want my house to burn down so that somebody else's house doesn't burn down. I had to live with this paradox of how unfair the world is—that simultaneously my relief and good news was somebody else's stress and bad news, and there was nothing I could do to change that. That paradox is horrible.
But the second part: the evacuation zones were coming a little closer and they were one zone away from where I live. We didn't know if we were going to be woken in the middle of the night with an alarm to evacuate. I had to go through the process of packing up my car and making my go-bag. I put as much stuff in my car as I could, and I had to—we all play the games like, "If there's a fire and you have to run out and grab two things, what would you grab?" I had to do that. You actually had to make the decisions: what am I going to take and what am I going to leave behind?
I found myself bringing things that I never thought were important to me, and I found myself leaving behind things that I thought I would take. But the one thing that was amazing was stuff that I couldn't fit but I still had love for, like my favorite painting in the world. I just couldn't fit it in my car. I stood there in front of it and I said "Thank you" and I said "Goodbye." And it was like saying goodbye to a loved one. I've already said goodbye to everything here. I did it months ago.
I think this idea of gratitude—gratitude for what we have, but also acknowledging how temporary all of this is—I think that it makes you happier. Failed relationships—you could be angry at the other person, or you could be grateful for the lessons they taught you or for the good times you had. I think to change our minds to gratitude—and you can—it sounds a little bit hippie-dippie to have a gratitude practice and that's fine. If that's your thing, lie in bed every night or keep a journal and just say the things you're grateful for. When was the last time you called a friend out of the blue and just said, "Thanks for being my friend"? "Hey, just wanted to call and just tell you I love you, just tell you thank you, and that's all. Just a quick two minutes."
I think if I said that to one of my best friends, they'd think I was losing my mind or something, that something was wrong. They’d be so concerned because it’s such an unusual thing for me to have done.
Okay, so you can do it this way. "So, I had a guest on the podcast and he came up with this thing that is so outside of my personality but I'm going to try it." Then you could do that. I'm new to this. I know for years people have been saying, "You should have a gratitude practice and keep a gratitude journal." I tried it. "Okay, grateful for my sister, grateful for my family, grateful for my friends, grateful for the life that I live. Right, goodnight." Next day: "Grateful for my sister, grateful for my family..." I found it so repetitive that I was like, "Is this worth it?" Sure, every now and then something was different and new. I've come to the conclusion that if it's the same three things every single day, good.
I was thinking about this a lot the other day when someone asked me, "Think about all the people in your life and imagine if they were sick and imagine if you had a billion dollars in your bank and the billion dollars could cure their sickness. Who would you cure it for? Would you spend a billion dollars to cure your girlfriend's sickness, your mother's sickness, your father's sickness?" And you would. I’d give every penny I had to cure an illness that my girlfriend had, even if the risk was low.
And as I was thinking through that, I was like, but then if you look at my calendar and how I'm allocating my time against these individuals and against my priorities, there's a real imbalance here. Over the last couple of weeks in particular, I've been on a bit of a journey of realizing just how important four or five people in my life are and how much I neglect them.
Yeah, I mean, of course. We only—and it's—you're right. If you say give a billion dollars and you can cure this disease that affects two million people, 10 million people, you'd be like, "I'll give some money." But if it was one family member, you would exhaust every resource, you would quit your job, you would do everything you can for a 1% chance. And people do; they quit their jobs and so many charities have been started because "my father died, my mother died, my sister died, and now I've devoted my life to [this]." It's because it's personal. Of course, that makes sense.
It’s why some entrepreneurs are good and some entrepreneurs are bad. How personal is the thing that you're working on to you? I only like the entrepreneurs that I love—I want to know that they are solving a problem that they struggled with or that somebody they love struggled with. If they read an article in a magazine and thought, "This is a great market opportunity," there is no passion there. That is driven by money and power only. I want to know somebody that is so deeply personal to them that they will stop at nothing. They will run through a brick wall and find every creative solution. It goes right back to the small company versus big company. It's passion and a vision that is bigger than the resources that I have.
I had a conversation with somebody recently where they wanted to change the goals for a business problem. I said, "We can't just change the goals because they're difficult. We might miss the goal. Yes, we have a very aggressive goal and the likelihood of us hitting it is incredibly low, but why would we lower it?" And they said to me, "You know, I don't like to fail," they said, "and I know you don't either." And I said, "Ah, that's where you're wrong. I have spent most of my life a failure, and I am very comfortable being a failure. I think of myself not as a success; I think of myself as a failure." That's because my ambitions are bigger than my skills or my ability to achieve those ambitions. So almost everything I’ve done, with a couple of exceptions, have fallen short of what I had hoped for. I'm very comfortable with that. Failing at 80% is really much better than succeeding at 30%.
I think this idea of fear of failure and embracing failure—I don't *want* to fail, but I think it's important to have dreams that are beyond your skills or your resources. That's where creativity comes from. That's where resourcefulness comes from. And you tell me the stories of your own team—it's the resourceful ones.
Now we go back to AI. AI is not going to figure that out. There was a book called *The Wisdom of Crowds* by James Surowiecki. I think it was that one. Where people with experience knew what to do versus people who are just trained. There was a bunch of firemen fighting a fire in wildfires. The wind picked up and the fire was coming really fast towards these firemen. True story. They all started running for their lives as this fire was approaching them unbelievably quickly. But the problem was, they looked ahead and there was a small hill, which means you’re going to slow down because you can't run fast up a hill and this fire is coming fast. The senior guy on the team started screaming, "Get down! Get down! Get down!" And they all ignored him; they were all running for their lives. And he just stopped running and got down and put his hands over his head and just lay in a ball. The fire was going so fast that it blew right over him and it caught up with the other guys and burned them all to death. Now, they didn't teach them that in fire school. It was accumulated knowledge of wisdom that came from experience, that he knew the right thing to do in the moment. His gut said the right thing to do is to drop down, you'll be okay.
This is why I'm going to sound like a broken record: the importance of doing the work yourself. Of writing the book, painting the painting, choreographing the dance, composing the symphony, building the business, having the difficult conversation, stumbling and bumbling. Let's say you have a fight with your girlfriend. You don't want to be in a fight. You don't like being in a fight. You want to do the right thing. So you go to ChatGPT and you’re like, "My girlfriend and I had a fight. This is what the fight was about. I think I did some stuff wrong, I think she did some stuff wrong. This is exactly what happened. Tell me what to do." And you go, "Babe, I just want you to know I want to take full accountability. I'm really sad that this happened and I want you to know that I care about this relationship." And she says to you, "Did you get this answer from ChatGPT?" And you go, "I did." How's that going to go?
You did everything right! You did everything right, but for the fact—and it goes right back to what you said—which is it removed the humanity. It removed the personality. It’s artificial; it’s fake. It’s not you telling me sorry; it’s ChatGPT telling me sorry. Even though you went with good intention to get it right, I would rather you get it wrong and bumble and fumble it with me and be like, "Babe, I don't know how to do this. I'm an asshole." And then she fights with you because you got it wrong, and you rumble through it together. What happens when you come out of the fight? You're closer. Not because you got it right, but because you got it wrong and you learned the skill. And you get better and better and better. She knew it wasn't because you asked AI in the moment because you just wanted to resolve the problem and remove the tension; it's because you learned the skill for the time that you don't know when it's going to happen because you're equipped for this relationship. And it's that investment in the relationship rather than trying to transactionally solve the problem before me. That’s the difference. It’s infinite versus finite. It’s transaction versus journey. I'm in the journey of this relationship versus "I have a destination, I gotta solve this problem now, otherwise this is going to destroy my relationship."
All of this is coming full circle. It comes right back to everything we started. I think it's hilarious that you and I are having a conversation about AI because I'm not an AI expert and I'm not in the AI business. But I *am* in the humanity business. And I think everything we're talking about from every angle, we're battle-testing this idea. What we can't get away from is human beings really want human beings. Human beings really want human experiences. Human beings really want things made by human beings. And we are not only okay with—we want—imperfection. Because imperfection is the very sign of human.
I was just thinking about how when I'm in an argument with my partner, if she was perfect, if she was completely composed, if she was looking at me without emotion, without expression, and if she was spewing ChatGPT-like responses back at me—it would be a little bit infuriating but also it would be completely dehumanizing. It's funny how actually, even in conflict, I want emotion, I want imperfection, I want human resonance.
Struggle is a good thing. I think in our modern day and age, we have under-appreciated and under-represented the value of struggle. If you ask anybody in their life, "Tell me about a time in your career where you felt like, boy, this is the most amazing thing I've ever done, I'm so glad I'm a part of this," it's not the big win, it's not the big success, it's not "we finished everything on time and under budget." It's "Oh my god, this one thing went horribly wrong, oh my god, it went so badly, and yet the way we came together..." The most important thing in my career was when I lost my passion and went into deep depression. Never want to go through that again, but really glad it happened. All of our relationships—professional, personal, romantic, whatever they are—all of our relationships get better when we go through struggle together. We know the way the human animal works. We know that oxytocin is released when you have shared struggle. That's why when you put people in boot camp and they go through shit together, or there's a natural disaster—all of a sudden I don't care who you voted for, I saw your house blow down in the tornado, I got you, don't worry, we’re neighbors. We can put aside all the rational nonsense, the intellectual nonsense, and at the end of the day, human beings are good at helping human beings.
Struggle also, in many contexts, *is* the value. When I think about a Simon Sinek book, the reason why I value it is because I know that Simon Sinek spent years writing that thing and pulling it together. The reason why certain handmade things are valuable is because of the pain and the toil that went into them. When you think about the art world and other creations through history, the value comes from the fact that human beings came together for a prolonged period of time and did something. In actually the investment *is* the value.
We're not buying the product; we're buying the story. Like the Mona Lisa—you're not buying a piece of art; you're buying the story that goes with the art. The story that it took to create the art, what the artist was going through, what they were thinking. You're not buying my book; you're buying the story of the making of my book.
And the Mona Lisa was stolen, from what I understand. I heard that part of the reason why the Mona Lisa is so valuable is because at one point it was stolen and then they managed to recover it again. Actually, it's just a painting, but the *story* of the painting is worth 100 million, 200 million, whatever.
Whatever. And so this is what we forget. The reason famous artists are famous is because you buy the story of that artist, not their talent. There's a lot of famous singers and actors and painters and dancers who are a lot less talented than the unknown ones, but you buy into the story. This is why some celebrities—as much as they talk about the paparazzi and the tabloids—they *want* to be in the paparazzi and the tabloids because it keeps their story relevant. It keeps them worth more because they're in the zeitgeist.
Apple know this better than anybody because you go to an Apple Store and they've laid out their products as if it were an art gallery. The three feet either side of the iPhone create the impression in my mind that this is a piece of art and there's only one of them. The fact that they've wasted all this space—which I know real estate costs money and that must have been expensive—pours into the device itself. If I'd gone into an Apple Store and there was a thousand iPhones like the old electronics stores all stacked on top of each other, I would assume the iPhone was worth less. But the story just by the frame in which I see it means, "Oh my god, this thing is..."
It's theater. It looks like one of one. It's theater, and some would call it manipulative, but we want things to *feel* valuable, not just be valuable. I could tell you I found a guy who makes cashmere jerseys and he uses the exact same cashmere as Loro Piana or some fancy brand. But the problem is it says "Dave's Cashmere Shop." I could tell you everything about where he sources the cashmere, how he makes it—it's the same everything—and you'd be like, "Yeah, Dave's Cashmere Shop?" Because you're not buying the cashmere; you're buying the brand. You're buying the story, you're buying the association. That's why brands have value because it's irrational. Humans are irrational. That's why companies invest in building brands—for the story.
As much as AI scares me, I still believe the technologists don't appreciate—and won't appreciate—and there will be a rebellion. Handmade will become more valuable, handmade will become more expensive, and people will want to say that. "You had *that* person write your speech for you? They did it themselves?" And I think that's good. It's the pendulum, right? We're going to get enamored with the technology until it's boring.
This also just expands generally—I know this sounds quite big and we're talking about these big things—but just to everything that you create. It's very, very tempting at the moment to just create something with AI and throw it up on your website, on your social media pages, or present it to the world as a presentation deck at work. But actually, I'm already noticing I'm attributing huge value and interest in things that I can identify as human-made.
I had a flashback a second ago to one of my favorite brands in the world. It’s a clothing brand and I was obsessed with this brand. I'd spend a huge amount—I don't spend money on clothes—but I would spend a huge amount of money every time they came out with a new item. One day the founder of the brand—and everybody knows this brand—he posted a photo from his factory. It was a video, and what I saw in the video was the shirt I was currently wearing as I watched the video, in a massive bucket with 4,000 others of the exact same shirt. In that moment—fell out of love. Because in my head, I'd painted this artisan picture of them sewing it. These two guys sewing it in their bedroom and then sending it to me.
That's probably what it was on the ad, too.
That's what it probably used to be, so I still had that image.
But it got too big. One thing that I've always understood—this is true for businesses, this is true for absolutely everything—scale breaks things. In the military, they have special forces: Navy SEALs, SAS, all those folks. There's a saying in the special forces that basically is: you can't scale special. You can take whatever training skills you have for the special forces and you give it to everybody—it's not going to work. Special can only be small. Scale breaks things. Every time. Apple, one of the highest quality operating systems in the world—what did they do? They refused to clone. They wouldn't clone their operating system. As a result, for years Apple had like maybe 4% of the world's operating systems. Microsoft said, "We’re happy to clone our operating system," so it was a little bit different on Dell, a little bit different on an IBM. Wherever you use it, it was slightly different, and they had 90-something percent of the world's operating systems. It’s because you have to trade quality for scale every time. There's a reason why buying fancy goods for a lot of money—because as you said, the way you make things has to change and you have to start making them in factories. Scale breaks companies. Think about how beautiful companies are—the number of companies that talk about "our company's like a family." Get to about 150 people, 200 people, get to Dunbar's number—not so much of a family anymore.
I think B2B marketers keep making this mistake: they're chasing volume instead of quality. When you try to be seen by more people instead of the right people, all you're doing is making noise, but that noise rarely shifts the needle and it's often quite expensive. I know because there was a time in my career where I kept making this mistake, and many of you will be making it too.
Eventually, I started posting ads on our show sponsor’s platform, LinkedIn, and that's when things started to change. I put that change down to a few critical things, one of them being that LinkedIn was then and still is today the platform where decision-makers go not only to think and learn but also to buy. When you market your business there, you're putting it right in front of people who actually have the power to say yes. You can target them by job title, industry, and company size. It's simply a sharper way to spend your marketing budget. If you haven't tried it, how about this? Give LinkedIn Ads a try and I'm going to give you a $100 ad credit to get you started. If you visit linkedin.com/diary, you can claim that right now. That's linkedin.com/diary.
Is it harder now to find love? Because there’s lots of stats that say we're having less sex, we're lonelier than ever before. Interestingly—this is maybe an adjacent point—but I was looking at Bumble’s share price. I love the founder of Bumble, Whitney Wolfe Herd. She's a really, really good friend of mine; I think she's amazing.
Has she come on?
She has. I know her and she's a wonderful human being. But when I was looking at the Bumble share price, it painted a really interesting picture because then you overlay that with some of these other dating apps and you see—this is the—well, she's had to come back. She's just come back in to turn the company around. In the interview, she says she’s going to revamp Bumble to make it not about finding love with others, but falling in love with yourself. There's also going to be this dating marketplace, but her first objective is going to be: get people to love themselves through coaching and all these kinds of things on the app, and then find a partner.
Sure. I mean, I agree with that. We’re all broken records, right? I don't mean that as in we’re broken souls. Your customers will never love you until your employees love you first. You’ll never find somebody to love you unless you love yourself first. Look at failed relationships where there's so much tension; it's somebody's lack of self-love that contributes to the failing of that relationship. I have a dear friend who's going through it right now; she just can't find love and it's because she doesn't love herself. And she knows it. It's a hard thing to do. So if Bumble can crack that code, more power to them.
But this is the problem with a lot of these things: they are common knowledge, we just don't do them. Everybody knows how to be healthy, everybody knows how to exercise, everybody knows what eating right means. Don't do it because wrong is easier and right takes effort. Everybody knows what we're supposed to do in a relationship, everybody knows we're supposed to listen, hold space—everybody knows philosophically what we're supposed to do, but we don't do it.
By the way, it's the reason why most people—I've written all these lovely books, and it's the reason why most companies don't use them. It's because my work is like exercise, which is I can tell you every single—if you want to get into shape, "Hey Simon, how do I get into shape?" Easy. Every single day, work out for 20 minutes. Every single day. Can I take the occasional day off? Yes, but not too many. Work out every single day and 100% of you will get into shape. I know it. 100%. When? I don't know, and neither does any doctor. That’s my work. Yes, I can profoundly help you find purpose with *Start With Why*, I can help you build trust on a team with *Leaders Eat Last*, I can help you embrace the infinite mindset and have this incredible calm in life. The reason most companies won't do it—this is a book for innovation right here, *The Infinite Game*—the reason most companies won't do it is because they need it to happen by the end of the quarter or the end of the financial year. It may or may not. I have no clue, and I cannot predict that it will or won't. It'll work 100%, I just don't know when.
And the problem is, goes right back to the beginning of this conversation: we’re all so obsessed with the output, we're all so obsessed with the result that we've completely ignored the value of the journey. People would rather hit the number at the end of the year than build a good, strong company. If I meet another entrepreneur, when I say, "So tell me about your company," "We’re hyper-growth! We’re a hyper-growth company, we’re a gazelle!" I always say the same thing, because I'm an ass: "Can you please give me one article from a reputable publication—just one, and I don't care the publication—that says that building a hyper-growth company is good for business? Just one." And the answer is you can't, because it's not.
Why are we so obsessed with high-speed growth? It's because our investors want us to be obsessed with high-speed growth, or our egos want us to be obsessed with high-speed growth. If high-speed growth happens by accident—that happens for many of the unicorns—it was an accident! I think building a good company is better than building a fast company. I think building a good relationship is better than building a fast relationship. We're all so obsessed with speed and immediate results. Present company included; I've had to learn this the hard way. I think there's something joyful and beautiful about slowing down, saying thank you, reprioritizing friends.
Before cell phones, we went to work and then we went home. We didn't do work at home because we couldn't do work at home. We didn't have computers at home, we didn't have cell phones or people to call us. So you did work at work and then you left. I remember when cell phones started, AT&T had this campaign that they showed people working on the beach with their computer. Now you can leave work! And that's not what happened; work came with us. We never left work; work came with us in our pocket every day, every vacation, every evening, every weekend.
As you said that, I thought, "You know what, that's so interesting because that kind of means that friction creates freedom in that regard." The friction of not being able to go home and tap away on my computer all night meant that I had a certain level of freedom because I had to wait for things. In the same context with AI coming along, now I can build software throughout the weekend whether the agency's working or not. Now I can build anything I want at any time using the phone in my pocket. The friction has come down again, and therefore the pressure to do it now—because I *can* do it now—goes up.
That’s so good. We’re taking work with us. Everybody has a story of like where the battery ran out on their phone and they ended up having the best night, or the internet went out at work and they actually got more done. You hear these stories all the time. When we are forced not to take work with us—forced—it takes a bit of time sometimes to relax, but it's always better because you learn to stop worrying, stop checking.
One of the things I did—I can't delete Instagram completely as much as I'd love to, but I hid it. You can take it off the screen; it's gone, it's hidden. Then I took it off the suggestions, which most people don't even know you can do that. So only time I go to Instagram is when I have to go to it and I have to type in "I-N-S-T-A" and then it pops up. My usage of Instagram has plummeted because it has to be intentional. The problem with most social media is it's unintentional.
One of the big things talking about community, Instagram, AI that I think a lot about is: is the value of in-real-life community going to rise? I think we might be on the precipice of the community revolution. I say this because when I think about what's going to remain in a world where creating things goes to zero—like when you made a social network or you built an app or you built a movie or a media company or a podcast, that was half of the job. The other half of the job is getting it out there in the world. Now the people that have the other half of the job—which hasn't gone to zero—now have this tremendous advantage because we can all create, but we can't all distribute. Having community and building and fostering community I think now is one of the things that remains. What are the values of a community? How do I build a community?
I have a definition of community: community is a group of people who agree to grow together. Friends are at least two people who agree to grow together.
In marketing this is the absolute obsession at the moment: community, run clubs, brands becoming offline.
Offline is the new online. There's a company called Clicks. It was started by a talented entrepreneur, Alix. She was in college and she suffered severe depression and loneliness and didn't know how to make friends. Her company Clicks, she started it to solve her own problem—my favorite kind of company. Basically to help her friends at school, people at school, make friends. She did it by taking people offline and taking their phones away. She would come up with reasons to come together, whether it was running or this or that—it didn't matter what the reason was. She has built this business to just bring people together to meet people without phones offline. She has an app that she wants people not to be on.
And what is it that holds the community together? Is it shared values?
Shared interests is a way to start a relationship. Comic-Con, Burning Man—all of these larger-than-life events. Going to the football—you're everybody's friend when you wear the right colors. You see people on the tube who are going to the same game; they’re wearing the same jersey. You're friends. So I think common interests is a trick; it's a way of getting people to come together and it's a nice place to start because conversation is easy. You know at least one thing about this person that you have in common with them.
Do you need a shared goal in a community? Like in football, we have a shared goal: we want to win.
I think so. That seems to make sense.
The reason why I ask these questions is I am building businesses and brands and I know that community is one of the most important things. There's a big difference between having an audience—which is what you might have on a podcast—and having a community. As a brand leader and as an entrepreneur, I'm trying to shift from having an audience over to having a community. That’s about relationships and shared values.
I like to think that the people who really like my work—not the ones who just like it passively, but the ones who really like my work—if somebody says, "I love *Start With Why*" or "I live my life by *The Infinite Game*," that it says something about who they are and how they see the world and that we share the same values. Because I am, you know me, I'm an idealist and my work is consistent in the way I talk about things from the day I started to now and won't ever change. I think that's the value of values. The problem with the modern world we live in and the pressures that people face is money and fame and all the rest of it, influencer status—I think it sometimes forces us to question our values or walk away from them.
I was invited to a mastermind group. FOLKS! Folks like me, authors, speakers. This is what they told me: "Come together based on shared goals, shared values, how we can work together to improve the world together." I'm like, "Oh, sign me up! I'm in!" So I went, and we sat around a room, and they spent all of their time talking about how they can share their lists with each other and how they can cross-promote with each other and what margins you're getting on this. I’m like, "You guys are just talking about making more money. I thought we came here to do common good together." They didn't invite me back.
But the point is money and fame are seductive. This is Joseph Campbell's Hero's Journey: you start off as the reluctant hero, you get called to your mission for some reason, and at some point in your journey there will be something to seduce you away from your mission—money or power. Luke Skywalker was nearly seduced away from the vision. This is what the hero has to go through. Do you have the friends who will slap you around and keep you in line and say, "No, you signed up for this, you have to stay true to what you're doing"? Because I think none of us have the courage or the strength to stay true to our cause by ourselves. We need to have at least one person who believes in us to give us the strength to stick to it because the temptation is overwhelming.
When you start making money, and you start making money for something you didn't expect—I never expected to have a career from any of this stuff. It happened by accident. And you get to the point where you start thinking you're more important than you are. "Do they know who I am?" No! No! Get over yourself. You start becoming seduced. I think the seduction when we turn on social media and we watch the Kardashian model—and you have people who pursue influence without knowledge or skill. They have the other three buckets, but they don't have the first two buckets (knowledge and skill). It is unfulfilling for others.
I was at a concert and this woman walked down the aisle and some guy was taking pictures of her as she was posing. The person next to me goes, "She's a famous influencer." And I said, "You mean she's a freelance employee of an algorithm?" Somebody who chooses to be an influencer—that's what you are. You are a freelance employee of an algorithm, and the minute they change the algorithm, you might be out of business.
You just lost like 170 followers!
I mean, maybe. But I don't have a problem with the concept of being an influencer if you bring something of value. The only time I have a problem with it is if you make it about you. "Look at me, look at me, look at me" versus "I have something that I think this will help you." In the early days of influencing, there was a young couple that were trying to get followers and they would do crazier and crazier things. He took a big dictionary and he put it over his chest and she took a gun and shot at the book, thinking that the book would stop the bullet. She killed him. She killed him on camera. They admitted afterwards they were doing it to do bigger and crazier stunts to get more and more followers because the financial pressures of driving those YouTube views was overwhelming. It's an extreme case, obviously, of how we will lose our minds trying to gain followers. I don't mind if people gain followers by giving. But to gain followers by taking—"Look at me, look at me"—it's the intention.
Simon, I printed off some graphs which I think are absolutely fascinating and dovetail into everything you've said today but also into your work generally. I'm just going to give you all of these to give you a second to look through them. I want to get your read and interpretation on them.
"Adults' lack of meaning and purpose; overall loneliness." Okay, I mean that makes sense.
To me that didn't make sense. I couldn't understand how if someone is low in purpose, then they are lonelier.
It just makes sense that when you have lack of purpose, the likelihood that loneliness comes nearby—I think family gives meaning, friends give meaning. You feel like you're there for someone else. But if you don't know why you're showing up every day, I think it feels like a lonely existence; you feel like you're searching. When you have a sense of purpose, it gives you a mechanism to meet people, it gives you a mechanism to make decisions, it gives you a mechanism to talk about yourself in a way that's quite inspiring to others. When you say your "Why"—I wake up every single day to inspire people to do what inspires them. What do you do? It's a magnet. Versus "I'm a dentist" or "I don't know," which is even worse.
"Distribution of people feeling lonely worldwide by gender." It's about 50/50.
Are you surprised by that? I thought for some reason men were more lonely.
"Not at all lonely" looks like women do better. I would think women are probably better at making friends; maybe I have that wrong. "Adults' mental health ratings: 68% of people who have depression are lonely and 67% of people who have anxiety are lonely."
Do you think good mental health is a foundation for being not lonely?
No. I think having somebody who cares about you is a foundation for not being lonely. When you're in a period of strained mental fitness, it definitely can manifest as loneliness and anxiety. The best way to manage through that period is to lean on the people who you know love you. That will help. I read a couple of years ago that when people are lonely, they fall into a state of self-preservation because of some evolutionary mechanism which meant that if we were alone on the Serengeti in Africa, we would sleep worse, we would become more selfish, we would become more angry. Our cortisol levels would be up, which means more inflammation. This idea of self-preservation basically means that lonely people become more selfish, more bitter, more angry. That's not conducive with finding more friends, but it is conducive with survival.
It makes it more conducive to survival as an individual. If you're in a deserted island and you're lonely, the cortisol rises and you become better at being on edge, which is a survival mechanism. But if you live in a community with other people, then it is counterproductive because we are social animals and I need you to help me and you need me to help you. So if we live in a tribe together and I'm the selfish asshole, you're not going to wake me and alert me to danger tonight. You’re just going to leave me. So it is counterproductive. I think you're right: when somebody feels lonely, they do go into survival and they become paranoid and they think everybody's out to get them. But the problem is you don't live on a desert island. And that's one of the reasons I think it's dangerous.
We’re increasingly being living on islands. The islands are different now; they're four walls in a white city. It's so funny that so many of my friends are using this word "loneliness." My masseuse yesterday was saying to me that she's lonely. This is a woman that lives in Los Angeles, has people around her, but she's lonely. I remember when she went—and she stayed because we had a conversation and I texted her and said thank you for being so open and stuff—I was thinking about what advice I could give her. She's got no friends, she's in Los Angeles, she's desperate for friends. She doesn't have a partner anymore because she's had a divorce. What advice do you give someone? Is it "take more risks"?
It's easy to give the obvious advice like, "You gotta put yourself out there." But when you're in a period of loneliness and stress, it's hard to find that energy and that risk-taking, especially when you're down on yourself. But I think for me what I've learned is to put myself second—meaning don't worry, don't try and solve my problem, but do I have somebody else who's lonely that I can help? How do I help somebody else who's dealing with their loneliness? It's the act of service that is so valuable. If you guys are talking and she has many clients and somebody else is lonely and her willingness to admit that "I'm lonely" out loud creates a safe environment for somebody else to admit the same. Then once she learns that they're lonely, now she can say, "Tell me about it," and then she can talk them through it and hold space for them. Her ability to help somebody else manage or understand their loneliness will help her.
So interesting because one of the hallmarks of her personality—something she says to me every single time she comes over—is that she doesn't like sharing herself with people because she thinks if people get to know her they'll change. So literally, she's been my masseuse for many years now and she's scared about people knowing the details of her life. So she guards it all. It took me like 20 sessions just to figure out she had a family. I had no idea she had two kids! When I asked her, her body language went like this: [sighs] "Yes, I have kids." I said, "Why are you so guarded with your information?" "Well, if people know who I really am and they know more about me, then they'll change or they may not like me anymore, they’ll think differently about me, so I just keep it to myself."
This is the age-old problem. It's "I'm never going to—I'm going to keep my walls up high, I never want to love anybody because then I'll get hurt." And then you just end up lonely and hurt. This goes back to struggle. You and I both know that if somebody chooses to go on an entrepreneurial venture or adventure—the statistics bear out that over 90% of all new businesses will fail in the first three years. What idiot would ever start a business? You have to be compelled by something else to make you do something with an overwhelming statistical chance of failure. It's opening yourself up to failure that is the thing that makes it work, for a small percentage. It’s the same for love or relationship or friendship, which is it absolutely comes with risk. There’s nothing risk-free. Yeah, they will—some of them might change. Yes. Some of them might not like you for that very reason. Yes. Yes. And the odds are equal that someone will fall in love with you and love you and like you and think you're the best thing and think you're amazing. So if you can't take the risk, you can't get the reward. If you don't play the lottery, you don't win the jackpot. If you aren't willing to—I'm not telling you to open up and tell everybody your deepest, darkest secrets. But if you're not willing to give somebody anything to latch onto, to be like, "Me too," then it's going to be a hard road. Or it'll take somebody to chip away at you 20 times to be before you open up, but the fact that you did and she got to open up a little bit, she could make a friend in you.
Now she's fully open. We’ve been through everything. I know where she wants her house to be!
There you go, you see! So you have to point out to her that this friendship and that you know so much and that she feels so safe with you *only* happened because you chipped away at her and she finally wore her down and she opened up. It can happen in two directions: sometimes we have to take the little risk to just tell somebody a little something about ourselves to find some common ground, or sometimes it’s somebody who's so curious about us that they chip away and chip away until we give up and open up and that person becomes a friend. One of the reasons she should be grateful for the friendship is you kept trying. You could have just tried three times and been like, "Forget it, I'll just lie here quietly and have a massage."
Is this what connection is? When you said "me too." Finding something to say "me too" with someone—is that the essence of what connection is?
I mean, it could be values, it could be interests. But to find—I think yes. This is—if you want to go political—one of the problems in our politics is both sides think they're right and both sides think the other side is wrong. Neither side is willing to try to even understand what the other person's point of view is without thinking them an idiot or thinking them wrong or thinking them sheeple. The ability to say, "Can you tell me more about how you came to your beliefs? I'm genuinely curious." And to not agree or disagree, but to be curious, to be an investigator. I've done this with people who have polar opposite political views with me. At some point, we will get to a level of me just chipping away trying to understand that they will say something that I'm like, "100% I agree with that." And then from that point on, there's a simple validation—not agreement, but a validation—that your opinions do matter and we do have common ground. From that validation, they become vastly more open to my point of view also, and curious to my point of view also. So the ability to listen and be curious even if you disagree is one of the most under-appreciated skills on the planet. And yeah, I think when you find—when you're able to say "I agree," then you can find community. Maybe that's what we need to heal this country or most of the countries in the world right now: one group or one person to just be curious rather than agree or disagree.
There’s something about relationships here as well. My girlfriend is very emotional, like all of us. Sometimes in those interactions when we sit down and there's a problem and we spend the first 60 to 90 minutes trying to figure out what the problem is, it doesn't sound very logical to me. My job in that moment actually isn't to parse through truth and to figure out and to correct truth; it is to sit and let someone get it out.
You and I have the same problem, which is we live above our necks. And you and I both have the same struggle, which is to learn to live below our necks. You and I are head people, and we have to learn to be more heart. I want to understand everything, explain everything, evaluate everything, analyze everything. When it comes to my emotions, I'll give you an analysis. When it comes to your emotions, I'll give you an analysis. And so I have to learn to be like, "I feel this," and that's it.
And I feel the same way—it's funny because I'm good at it with art. I always tell people, you don't have to understand art. I'll take you to a museum, I'll take you to a gallery, and if you look at a piece—and I know you're intimidated to come because you don't understand art or you don't understand music or whatever it is—all you need to do, this is the only rule: "Do you like it?" "I do." "Why?" "I don't know, I just like it." That's it! You're done! You're done. "I don't like it." "Why?" "I don't know, I just don't like it." Great. Excellent. And now we're going to look at 10 pieces that you like and I'm going to see 10 pieces that you don't like. And I'll be like, "You like all of the Impressionists and you hate all the Old Masters. So why don't we just go see more Impressionists?"
And so when your girlfriend opens up to you, you don't have to agree, you don't have to disagree. You just have—and you and I both have to learn to stop thinking and to just feel something. When somebody says, "Where do you feel it?" I'm like, "What? That’s the stupidest question I've ever heard. Where do I feel it?" And they've literally had somebody take me on this journey, and she goes, "You told me an emotion you have, Simon. Where do you feel it? In your body, where do you feel it?" And I'm sitting there going, "You've got to be kidding me." But all right, we'll go through this. She says, "All right, where in your body did you have some sort of reaction?" "I... here." "What happened?" "It got a little tighter in my chest." Okay. And I went on this journey with my friend Bea, Bea Voce. She's incredible. She does repair with couples; she's just incredible. She helped me recognize that my body *does* react to my feelings: tension in my shoulders, heavier breathing in my chest, clenching my fists. My body *does* react. And so I'm learning to experience feelings beneath my neck when my inclination is to do everything above the neck. It’s a hard skill, especially for men. When you meet spiritual people, they are all below the neck, and we think it's stupid. But they recognize that we have an inability to feel because we want to think about everything. So we both have a lot to learn from each other.
Change in the number of posts for automation-prone jobs compared to manual-intensive jobs. Knowledge work is going to get hammered by AI. I met a guy in Japan who's one of the very few guys left—there's like 100 of them left, 150 of them left—who make samurai swords in the traditional way. They hammer the metal and he folds his own metal and he makes samurai swords the way they made them 200 years ago. We went to his little workshop, and he's this little old guy and he's telling us the story: "How did you do this?" He's like, "Well, I had a desk job, I worked in a company, and I woke up one day and I was like, 'I can't do this. This can't be my life.'" He had always been enamored by sword making, so he found an apprenticeship and tried to learn. He's like, "I'm just starting to get the hang of it, but I have a lot of room for improvement." We were like, "How long have you been doing this?" He said, 30 years.
But that’s so Japanese! The Japanese are like, "They'll never be good at this, I'll just keep working at it." And it's such hard work. But I think there's something to be said for—I think a lot of us, like knowledge workers—you ask them what their hobbies are. And like maybe there is an opportunity to learn a skill. Look at lockdown. What skill did you practice during lockdown? What did you learn?
DJing, running, cycling.
DJing! DJing! I did Kintsugi. It's the Japanese art of fixing broken things with gold. You take a broken plate or broken cup and you put it together with gold paint or gold epoxy. The whole concept is you can make something more beautiful after they're broken. I love the philosophy of it. I spent hours doing freaking Kintsugi. Ask me how much Kintsugi I've done since we came out of lockdown? Zero. How much DJing have you done? Zero.
And so maybe all this free time that we're supposed to get—which I still don't think will happen—maybe it's not such a bad thing. Think about the joy you had DJing. I had so much fun doing Kintsugi. I would spend hours just with my head down, focused. I was so relaxed, not thinking about work.
So why is that—that's the other question. People keep talking about how we're all going to have all this spare time. We've lost all of our spare time! We have no spare time because all we do is work and think about work and talk about work. If we go back 40 years, 50 years, there was plenty of spare time. People went bowling and they went to the movies and they went over to each other's houses for dinner and they cooked. Isn't it a good thing that we're getting time back? We got a lot of good things out of lockdown, and that's extreme. So maybe it's okay that we get some time back because it sounds like we've lost all of our own time. Maybe AI doing some of the work for us is the thing we've been desperate for for the past 30 years. Just saying.
This is quite embarrassing for me to admit, but if you know me well, there's something that you know about me which is a function of my personality, and that is that I lose everything. I've lost my wallet, I've lost multiple passports. I now actually have two passports because there's a high probability of me losing one. And when you lose your wallet overseas, as I have many times, it's a particular inconvenience because you also lose your driving license and your credit cards and those kinds of things.
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For anybody that likes matcha, for anybody that likes lattes, one of my companies has just launched canned matcha lattes. I was speaking with the founder, Marissa, and she said that creating this product has been no easy feat. They tried launching in 2021, but as is often the case in business, the development process turned out to be extremely complex. So they've spent the last four years testing and refining every single detail to create this, which is a Perfectted Matcha Vanilla Latte and a Perfectted Matcha Strawberry Latte.
What we have here in these cans is barista-quality matcha straight from the can, and it tastes like it's just been made from your favorite cafe. Naturally sweet and naturally creamy in a can. And the reason why I've invested in this company and I drink matcha is because matcha as an energy source gives me lasting energy without the big crashes that I get from other products. You can grab their ready-to-drink canned matcha lattes at Waitrose, Tesco, Holland & Barrett. And here's a little incentive for you: if you go to perfectted.com and use code DIARY40, you'll get 40% off your first order. Please don't tell anybody; keep that to yourself. That's code DIARY40, you'll get 40% off on perfectted.com. So go use that before they change it.
What are you struggling with in this season of life? I think I've asked you this in every conversation we've had, and the answer's evolved.
I'm doing so much right now. By the way, absolute joy. And I wish I had more time in a day. Not in the sense that I'm deprioritizing my friends—you talked about how you would give them all your money to secure them but you don't give them any time. I actually have gotten very good at this. I will schedule friends like meetings in the middle of the day. Haven't seen a friend for a while? 4:00 in the afternoon, tea with a friend. I leave the office. I’m going to a meeting. Because nobody says, "Hey Simon, where are you going?" "I'm going to a meeting." "Where are you having the meeting?" "At that restaurant." They're like, "Have fun."
Nobody will give me any kind of grief if I'm leaving to go to a meeting. Now I go and see a friend. I put it in and I give them equal weighting to things that I have to do at work. Because I've become much more discerning—like do I *have* to have this meeting or this phone call today? Or could I do it next week? I could do it next week. And you realize we add fake urgency to things.
I have a friend who's kind of amazing. He's way busier than me. He says, "I don't want to spend time with anybody—" I saw it was really funny. He came out of a meeting and he had a meeting with a very fancy person who was courting him for business. He comes out of the meeting and I'm like, "How was it?" He's like, "Total waste of time." I'm like, "He wants to work with you badly?" "No, he wants to work with me badly. Total waste of time." I'm like, "What are you talking about?" He's like, "He's just some rich asshole. Like I learned nothing, I didn't enjoy it, and I don't want to work with him."
I was like, "Tell me more." He's like, "I only want to work with people who, when I spend time with them, they teach me something, I laugh, or I feel inspired when I walk away. And if somebody just sucks my energy, I do not want to work with them." I was like, "That’s amazing." To have that level of confidence that you would turn down money in your business.
Now what if we applied that as much as possible in our lives? Like what if we stopped hanging out with friends who just sucked our energy? Are they really friends? Rather than spend more time with people who we enjoy. What if we only take meetings from people we're excited to take a meeting with, not that we just see dollar signs and opportunity? And what if we only partner with companies where we really like the people who work at those companies? We make a little less money with them versus that other company, but I really like them because when things go wrong, I want to call that person.
I've seen people like former CEOs who are like, "I now am going to write my book." And they've got multiple offers and there's a bidding war, and they always ask me, "Which publisher should I go with?" And I always say the same thing: choose the one you're going to fight with best. The goal is to make a good book, there's going to be creative tension, there's going to be fights. Choose the publisher who believes in your idea, believes in you, wants to make a great book—who you’re going to fight with really well. Every single one of them ignores me. Every single one of them takes the biggest bid, and every single one of them has written a shitty book that didn't sell.
Isn't that just relationship advice as well, though? Choose the person you’re going to fight with best.
Probably, yeah. The number of times that we forget about the quality of the product and we just want—it's the same for job interviews. Don't worry about how much they're going to pay you. As long as they pay you a livable wage, choose the job based on who you're going to work for. Choose the person. HR people used to say, "What are you looking for?" I'd always say the same thing: "The thing that I'm looking for is probably like looking for love, but I'm looking for a mentor."
Every time I'd evaluate a job, I didn't care how glamorous the brand was, I didn't care how much money they were going to pay me. I knew they were going to pay me *something*, I knew I could pay my bills. One company offered me $5,000 more and one company offered me $5,000 less, but I really liked the person over here. I took that job. It was the one thing I got right as a young person—that I always chose jobs based on who I would work for, not how much they were going to pay me or what account or what brand I was going to work on.
That's the one thing I got right. Because yes, I made less money than all my friends in the short term, but I got an education and a care and a love from somebody who took me under their wing. I learned leadership from Dennis Glennon, I learned leadership from Peter Intomaggio, I learned leadership from Pamela Moffett. I learned leadership from these leaders who took a weird liking to me and took me under their wing. Every one of them in the early days paid me less than I could have got somewhere else. Choose the people.
In my book that I wrote, the first chapter in it talks about this idea of these five buckets. I'm giving young kids advice on how to prioritize their career. The idea was that we all have these five buckets when we're starting our career: 1. Knowledge 2. Skills 3. Network 4. Resources 5. Reputation
These are the only buckets that no professional earthquake in your career can unfill. You can be fired, you can be canceled, whatever; you still have your knowledge and skills. But the other three buckets—they can fluctuate. Network, resources, reputation—they can fluctuate. The idea is that focusing on those first two buckets when you're young—choosing jobs based on how much they're going to fill those two buckets and also *what* they're going to fill them with and how relevant that information is—that really is the essence of career longevity.
I had this one kid step down from my company because he got a job offer at 21 to be a CEO in America. As he departed, I'm thinking, "He has not got the knowledge and skills to be a CEO." Within 24 months, the company had gone bust. He was back down to doing the same job he did for me. I thought, "Life just resets you to the level of your knowledge and skills over time."
I think you're saying the exact same thing; you did it more eloquently than me. The people who will fill that bucket with knowledge and skills are the people who, again, for some reason they’re good people, they’re good leaders, they take a liking to you, and they will put you in situations and they will let you screw up and fix your own problems. My bosses did that for me; they rewarded my behavior when I got it right as opposed to my results. Never got rewarded for my results; always got rewarded for my behavior. If I showed initiative, I got a reward even if the results didn't follow.
And if I got things wrong, they would say, "Wow, really screwed that one up, didn't you? What are you going to do?" They let me fix my own messes and they stood by and I knew that they were there if I needed them. Peter Intomaggio, one of the best leaders I ever worked for—annoyingly, he never answered a single question I asked. "Hey Peter, what should I do?" "I don't know, what do you think we should do?" "Well, I think we should do this." "Okay, go do that." "Peter, I'm asking you because I don't know!" "Ooh, well, you should probably go think about that." He was the worst, but what he taught me was self-reliance. If I don't know, then I have to go keep searching and keep talking to people. I have to have a point of view. It may not be right, and I'll find that out myself too.
I also learned to have backup plans from him. Something went haywire on me and it went so wrong, and it ended up being okay, but he made me sweat it. At 6:00 p.m., the phone rings, I see his name. I pick up the phone. I remember the whole call word for word. "Hello?" He says, "Close call today." I said, "Yep." He said, "Better to get shaved by the bullet than hit by the bullet." I went, "Yep." He said, "Have a good night." I said, "You too." That was the whole phone call. Since then, I always have a backup plan. If this thing that I'm trying to do doesn't work, what *will* I do? I've at least committed some thought to it. It’s only because of these great leaders.
It goes—this is the recurring theme of this whole conversation, which is it’s the struggle, it’s the journey not the destination, it’s the human beings that guide us, the human beings that hold space for us that make us better at what we do, better than how we show up in the world. AI will absolutely make our lives easier, like most technology makes our lives easier. That’s kind of the role of technology: to make life a little easier, a little more efficient, a little quicker, a little less strain on the muscles. From the plow all the way up to the internet and AI, it just makes life a little easier. But we're still human beings who are forced to live with human beings.
You're writing a book about friendship that we're all waiting for. I'm not going to ask you when it's due because I don't want to be your publisher, but I know that they chase and they chase. My closing question is: why? Of all the things you could have written about, Simon, you're someone who's able to traverse several subject matters across business and life and everything in between, but you’ve committed yourself to the struggle of writing a book about friendship.
There's an entire industry to help us be better leaders. There's an entire industry to help you have a successful relationship or a successful marriage or even find a partner. Industries, books, companies. There’s very little on how to be a friend. If you think about it, if you're going to have a successful career and survive the stresses of career, and if you're going to have a successful romantic relationship or marriage and survive that—you know what you need in both of those circumstances? Friends. Because when your marriage is falling apart, you go to a friend. When your job is falling apart, you go to a friend.
There's a few things that I've discovered about friends that I find delightful. I have been reorganizing my life to ensure that my friends aren't taken for granted and that sometimes I do deprioritize work in order to see my friends and spend time with my friends. The only reason I can get through any work stress or personal stress I have is because of those magical human beings. Friendship is the ultimate bio-hack.
I fundamentally believe that. If it's so valuable—if you know vegetables are good for you, you eat more vegetables. If you know exercise is good for you, you do more exercise. So if I say friends are good for you, shouldn't you do more friendships? Exercise is not fun or easy and you have to get over a hump sometimes. Eating vegetables can sometimes be boring and unsatisfactory, but you do it and you find new ways. Maybe friendship is not always easy or fun, but it's still really, really good for you. And the best thing about friends is it actually doesn't taste like spinach; it's the healthiest thing in the world.
How do I know if someone's a friend?
Have that conversation with them. In work you have deal friends—you have a lot of deal friends, podcast friends. And we have—I'm not talking about—there's all kinds of friends. There's friends that you just like hanging out with, they're just fun, but you're not going to go with them with your problems or to sort out issues. You're just not. Work or personal, they're just fun. There’s nothing wrong with that. But I think I'm certainly guilty of spending time with people that fill a space and make me feel not lonely, but at the end of the day, I don't feel smarter, inspired, brighter, lighter when they say goodbye. I just like, "All right, bye, that was fun." And I kind of want to spend more time with people who lift me, teach me, support me, love me, give me a chance to serve.
I struggle to make friends. Do you know why?
I think I'm lazy with it. I'll meet someone, I'll have a great connection with them, and then my follow-up—I don't really know what to do next. Your follow-up was crap! Oh, fucking hell. But this is what I mean: I'll meet someone, I'll text you and maybe I'll get a response, and vice versa. I think you left me on read! But you're the same. Are you the same? Or is it just with me? Just with you.
My follow-up game is like crap. I’ll meet someone, I’ll go, "Oh my god, we could be really good friends." I see so much in us. I love what you stand for, we have so much in common. And then it drifts because neither party has the tools or the skill of like what to do then.
We also live in a strange world where I've met people where I have all of that and I follow up immediately. I’m like, "Hey, I had such a good time, let's make a plan," and they're like, "What? Huh? What?" Or I call as opposed to texting, and people are like, "Why are you calling?" "Well, we had a nice time, I thought we'd maybe talk." And I think we live in this strange world where people put it out there but they don't really want it.
§02Transcript — part 2
Looping us right back to the beginning of this conversation—calling is so archaic to me that when someone does it, it's like a treat now. I was thinking what's taking that even further would be writing someone a letter. You know who wrote me a letter? Evan from Snapchat came on the podcast—the founder and CEO of Snapchat. By the time I'd got back to London, there was a letter on my desk from Evan and it just said, "I had a great conversation with you. Thank you for being so thoughtful with the questions, thank you for the research, here's my number, would love to stay in touch." And it blew me away.
AI wrote that. [Laughs]
No, it was with a pen! It was with a pen and his signature and his phone number, and I thought, "That is so beautiful." It's classic. Classic and classy. There's a premium on being human.
Simon, thank you so much. Thank you for being so generous with your time always. You always move me forward in my thinking in such a profound and unexpected way. I'll value [this] tremendously for a very, very long time. In our friendship, I'm going to text back even faster. We can go on more dates. And I look forward to that; I look forward to our next date in London, which I know is coming up sometime.
Yeah, we’ll go out, for sure. That'll be fun.
We have a closing tradition which I nearly forgot, which is the last guest leaves a question for the next guest. "What are you doing in your life to mentor someone coming up behind you?" And then: "Who is a person that you'd like to mentor, teach, or coach that needs your voice the most?"
My team is everything right now. Like I want to give everything I've learned to my team. I want the folks on my team to benefit from all the mistakes I've made. One of the joys of being in founder mode when it's not the actual beginning is I have way more in my skill and knowledge bucket that I want to pour out. One of the reasons I'm having so much fun in founder mode is because I want to give away everything that I've learned so that my team can be stronger and stronger and better and better. Because I want to leave something that can survive me, that the company will continue. And I really want to build something where they want to build it without me.
Feels like there’s been a change here. What was the catalyst?
For the past couple of years I've just been trying out a lot of different things to find a level of excitement and energy that I think I had lost for a little bit, and I found it. My team are so great, and they so want to push boundaries, and all I want to do is take the reins off. I want them to experiment, I want them to try things, and I'm trying to create an environment where they're creative, they do things, half of them will fail—I don't care, let's try again. I just love being around all the creative ideas that they're coming up with.
My team asked you to bring something that meant a lot to you, and you brought this. I don't know what's in this box.
Two medallions, medals?
Those are military challenge coins. I brought the round one just to show you what the traditional ones look like. This is the one I care about—I care about them both, but this is the one I brought. Challenge coins are—only generals or commanders will give these out. They’re hard to get. You get them when you do something of service. It's less formal than a medal; they can give it out to whomever they want. It's their way of saying thank you. The challenge coins that I've been given I'm very, very proud of because I feel like I earned them. The thing that I love is when they give them to you, they don't just hand it to you. They put it in their hand like this and they shake your hand and that's how they give them to you. They say, "Thank you Simon so much for coming here and helping us out." And that's how they give me the coin.
The reason this one means a lot to me is because I did some work with Air Force Top Gun. This is their coin and this is their patch. I did some work with them to help them get to the core of their "Why," what their true value was, just to make sure that their culture stays clear and good for a long time. We came up with three words, three actions that everybody who goes through Air Force Top Gun is required to do, which is "Build, Teach, Lead." The idea that you build a skill set, you teach that skill set to other people, and then you build leaders and you lead. This whole idea that you have a responsibility to build, to teach, and to lead, accumulate and give and serve. The thing that is so powerful is the commandant of the Weapons School after we did the work—he took those words and he put them on the coin. They exist on the coin and they have been on there for years since. I am so proud to have given something that has longevity, that is literally on the coin: "Build, Teach, Lead."
That is such a beautiful mantra for life.
Yeah. And they’re wonderful people who go there. What an honor that work that I did ended up on a coin. So they gave me the coin out of gratitude for the work that I did and it had my words on it. It’s not my words, it’s their words; I just helped distill them. It’s who they are when they're at their natural best. I just helped them put it in code and codify it.
Simon, thank you.
Thanks.
Always love our conversations and long may they continue.
Likewise.
Quick one, just give me 30 seconds of your time. Two things I wanted to say. The first thing is a huge thank you for listening and tuning into the show week after week. It means the world to all of us. This really is a dream that we absolutely never had and couldn't have imagined getting to this place. But secondly, it's a dream where we feel like we're only just getting started. If you enjoy what we do here, please join the 24% of people that listen to this podcast regularly and follow us on this app. Here's a promise I'm going to make to you: I'm going to do everything in my power to make this show as good as I can, now and into the future. We're going to deliver the guests that you want me to speak to, and we're going to continue to keep doing all of the things you love about this show. Thank you.
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