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The Diary of a CEOThe Diary of a CEO

Why AI quietly erodes the struggle behind your growth

How outsourcing the messy human journey to AI atrophies real skill over time; imperfection, friendship, and the struggle of writing are what grow you.

Simon SinekguestSteven Bartletthost
May 26, 20252h 6mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 2:22

    Intro

    1. SS

      Let's say you have a fight with your girlfriend. You wanna do the right thing, so you go to ChatGPT and you be like, "This is exactly what happened. Tell me what to do." And you go, "Babe, I just want you to know I wanna take full accountability and I care about this relationship." And she says, "Did you get this answer from ChatGPT?" And you go, "I did." How's that gonna go? (laughs) Now, you did everything right. But what makes people beautiful is not that we get everything right, it's that we get many things wrong. And I think in the modern world we live in, we forget that. Simon Sinek is back. He's the visionary thinker inspiring millions to cultivate human connection...

    2. SB

      Find their purpose and overcome any modern-day challenges. So with AI, do you think it really is cause for concern and deeper thought?

    3. SS

      So I'm not in the AI business, but I am in the humanity business. And here's 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 and its remarkable ability to write the book, paint the painting, solve the problem. But we forget the importance of doing the work yourself. And I think in our modern day and age, we have underrepresented the value of struggle. I am smarter, better at problem-solving, 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. But it's the same for love, friendships, conflict. And I think that we forget that we give up certain skills or abilities because of technology. But 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. And 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, 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, very human skills are suffering.

    4. SB

      So what are the other skills we need to equip ourselves with based on the way that the world is heading?

    5. SS

      Two things. One is...

    6. SB

      This has always blown my mind a little bit. 53% of you that listen to this show regularly haven't yet subscribed to the show. So could I ask you for a favor before we start? If you like this show and you like what we do here and you wanna support us, the free, simple way that you can do just that is by hitting the subscribe button. And my commitment to you is, if you do that, then I'll do everything in my power, me and my team, to make sure that this show is better for you every single week. We'll listen to your feedback, we'll find the guests that you want me to speak to, and we'll continue to do what we do. Thank you so much. Simon.

  2. 2:22 – 5:52

    Biggest Forces of Change in Society

    1. SB

      (laughs)

    2. SS

      Hey.

    3. SB

      Good to see you again. (laughs) What are you laughing at?

    4. SS

      It's just familiar.

    5. SB

      (laughs) Familiar. It's so interesting 'cause when I sit down to talk to you, you're one of the very few people that I don't come with a preconception as to what we're gonna talk about. But, but I, I come with a feeling, and the feeling that 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... I guess unknown. And I don't just mean with, with technology, but technology is one protagonist in the story, and there's 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 changes that you see happening at the moment in all of our lives that you think we should probably talk about today?

    6. SS

      That is a big question, and 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. And as you know, the world is messier than that. It is more nuanced than that. And nothing operates in a vacuum. Everything is connected to everything, especially in a, in a world that's filled with s- this rising technology called the internet and this burgeoning technology called the social media. And desires and feeling like belonging become more and more important. We're struggling to find them. Loneliness epidemic, stress epidemic, suicide epidemics. These are all feelings of disconnection, lack of control, and loneliness. And so that only exaggerates our feeling of loneliness and despair and wanting more and et cetera, et cetera, et cetera. And then you add in AI, and now those feelings of insecurity are just exaggerated like crazy, right?

    7. SB

      Mm-hmm.

    8. SS

      So now I find AI, there's an irony to AI, right? So if you go back to the '70s and '80s, right? You had the rise of robotics. And so robots are now coming into our factories, and we're able to cut employees by dramatic amounts, and we put people out on the street who... They're, they worked in a factory. Their, their father worked in a factory. Their father's father worked in a factory. Like, this is, this is what they know. And they say, "But these robots are changing... They're taking our jobs." And the ruling classes and the, and the Wall Street classes and the CEO classes, they go, "Yeah, I know. Technology. You're gonna have to find a new skill. Re-skill, re-skill. That's what you're gonna have to do. Re-skill." Okay, flash forward to AI. Here's where the irony comes in, 'cause the world is always... Nature abhors vacuum and life seeks balance at all times, right? Not always immediately, but it seeks balance at all times. It's always seeking equilibrium. Okay, so flash forward to AI. Now you hear the knowledge workers. It's the knowledge workers who are going, "My job." It's the coders. It's the finance people. "My job." The plumber is not worried about AI at all. The baggage handler at the airport cares zero about AI. And so maybe the right response is, "It's the future, man. It's technology. Re-skill, re-skill. You know, maybe, maybe become a plumber, you know? By the way, money's really good. (laughs) You get to work for yourself if you want, you know?" Um, so I just find the pendulum kind of funny.

  3. 5:52 – 12:42

    Is AI Cause for Concern?

    1. SS

    2. SB

      With AI-

    3. SS

      (laughs)

    4. SB

      ... do you think it's overblown or do you think it really is cause for concern and deeper thought?

    5. SS

      The honest answer is, I don't know. Mm-hmm. Everybody falls on one side of, "You're over- you're over- you're, you know, the sky is not falling chiddle- chicken little." Or, "The sky is falling, and we're all gonna die." Right? The true- the truth, like most things, is probably somewhere in the middle. But the- the real answer is, I don't know, and neither does anybody else. Yeah. And it seems that we should have some sort of controls, 'cause we didn't put any controls on the internet. They did put controls on the internet in China. Like, children don't have the same access to, uh, social media like kids do here. Europe has controls on the internet, and America doesn't. And we're the ones that seem to be suffering more because of the lack of controls on the internet. Hmm. So, I think some- some- and by the way, when people s- you know, talk about deregulation and no controls, I mean, they make us wear seat belts in our cars. Yeah. You know? There's nothing w- th- we have speed limits. You know, and- and it's for the greater good, and yeah, sure, your seat belt's uncomfortable, but you'll get used to it. Like, and it's fine, you know? Mm-hmm. So, I- I think the call for no reform is- is wrong. Um, there are correct limits to keep things safe. Mm-hmm. 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're a- we're a results obsessed society, right? Yeah. We care about output, we care about performance, we care about numbers, we care about final product more than anything, right? And when people talk about AI, they talk about its remarkable ability to write the symphony, paint the painting, write the book, write the article, uh, solve the problem. Like, it- it is... And by the way, the technology's incredible. I asked it only a few months ago to please take this and put it in the style of me. (laughs) And it was- it was fine. I did it with a friend of mine who's also an author, and we both did it for ourselves. We did it on each other. It was really fun. And it was fine. I don't think it was good. It was g- uh, it was- it gave me a good start and I could edit it. Mm-hmm. I did it recently. We both did it. It was damn near flawless. It was- it was scary good, right? Now, AI doesn't know the thing I'm thinking about. It doesn't know that the next book I'm gonna write about is friendship. It doesn't know the point of view I'm gonna have on friendship. If you ask it, "What would Simon Sinek say about friendship?" it's gonna be, "Why this and why that?" You know? So, it's derivative, right? We know that. It's not original. We know that. But at the end of the day, the work is good. The symphony's good. The art is good. The article is good. The book is decent. Like, it's getting better and 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. Right? But when we think about AI, we only think about the destination. We only think about the output. We never think about the input, right? I can tell you that... And you and I can both say the same thing, which is, I am smarter, better at problem solving, more resourceful, better at patterrec- pattern recognition, not because an- a- 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 what I'm trying to get out of my brain, that excruciating journey is what made me grow. And sure, you can have an AI friend, and that AI friend has been trained like the best, best psychologist to affirm you, the best listening skills that exist. "Tell me about your day. Hmm, that sounds difficult. Hmm, boy, it's hard being you. Oh my God, it's so great being you. Have you..." You know? Like, it's- it's a- it's an affirmation machine built by a for-profit company that wants you to stay on. Mm-hmm. Can't neglect that. But for the fact that 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, right? And it's the- and- it- th- what made you a great entrepreneur is not that the company exists, is that you built it with your hands and you've got the scars to show for it. Yeah. It was when things went wrong and you were forced to fix them and think that now, when problems show up, you're quick, you're smarter. You're a much smarter businessman now than you were five years ago, six years ago. Yeah. Because you did it. And I think what we're forgetting is that there's something to be said for- and by the way, I'm a fan of AI. I want AI to make things. But I would hate to lose out on becoming a better version of me. And I think that, um, to really learn to grow... And by the way, I used to have a steel trap for phone numbers. I knew everybody's phone number. And then all of a sudden, my phone, my PDA, go- I don't need to memorize a phone number anymore. I don't know most of the people that I love. I don't know their phone numbers. I type their name in, right? I just have to know their name. And so my brain literally went on strike. It said, "Fine. Fine. You no longer have the capacity to remember phone numbers," and I can't remember phone numbers to save my life, right? So, we give up certain skills or abilities because of technology regularly, right? That's fine. I don't have a problem with any of 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, my- or my partner, my ability to know what to do when my boss yells at me but I don't wanna escalate it, or my employee is acting out and I don't wanna escalate it or fire them, well, how do I resolve this?... I've missed out on those skills. And simply asking AI, "How should I resolve this thing?" It'll give you an answer, and it may work, and you've learned nothing. Right? And so, it's the difference between... It's- 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. And I'm okay, use the boat. Also, learn to swim. So, I think there's something to be said for writing your own symphony, painting your own painting, building your own business, you know-

    6. SB

      It's so interesting-

    7. SS

      ... writing your own book. Not for them, not for the output, not for the output. For your personal

  4. 12:42 – 18:25

    Authenticity in the Age of AI

    1. SS

      growth.

    2. SB

      Before I got here today, I was writing a post for LinkedIn. And I was trying to make the case that everybody using ChatGPT to write their emails, their social media posts, their investment pitches that I received, ha- is now making the internet feel really inauthentic. Because people that I want- I knew for many, many years are now sending me these perfect cookie cutter emails with words that I've never heard them use before.

    3. SS

      Yeah, of course.

    4. SB

      And so when I read it, my brain mentally discounts it as not being their opinion, not actually being them.

    5. SS

      Yeah.

    6. SB

      And- and when you feel like you're speaking to someone's AI, the meaning is gone. So I was- I was writing this post about how actually now there's this premium on human-written language. Like, if you make a couple of mistakes-

    7. SS

      Yeah.

    8. SB

      ... and you use the old words, you don't use words like forged and robust.

    9. SS

      (laughs)

    10. SB

      I'd like to forge a partnership with you, Steven. (laughs) Furthermore, can we... I'm like, "You- you've never said that to me, mate." Like, (laughs) so...

    11. SS

      You know, the- the end dashes.

    12. SB

      Oh my gosh.

    13. SS

      It's funny, right?

    14. SB

      It's crazy.

    15. SS

      Yeah. But you- but what you're talking about- what you're talking about... Have you ever heard of the Japanese concept of, um, uh, uh, wabi-sabi?

    16. SB

      No.

    17. SS

      So wabi-sabi is a Japanese design concept which is beauty in that which is temporary or imperfect. Okay? So, have you ever seen Japanese ceramics?

    18. SB

      Yeah.

    19. SS

      They're wonky or the- the- the glaze is not even.

    20. SB

      Yeah.

    21. SS

      And they're beautiful. You know why? Because they're handmade. Tree bark, trees, you know, when you have a wooden bowl, wood is beautiful. Why? It's imperfect, right? Think-

    22. SB

      Unique.

    23. SS

      And unique. Things made on a machine are the same and less beautiful. And things made by hand are beautiful because they're imperfect. What makes people beautiful is not that we get everything right, it's that we get many things wrong. And what makes us fall in love is not the person who's perfect, it's the person who accepts our imperfections, and we know we're in love when we learn to accept theirs. Not learn to, want to. Right? And you're 100% right. I now know, 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. It's because I want to know it was touched by human hands. And so I think you're right. What'll happen is everything will be so perfect that it'll be as if we're all driving or using things that everything came off, uh, a conveyor belt.

    24. SB

      Mm-hmm.

    25. SS

      And what we will start to desire is things that are made by hand, because by the way, we... R- think Rolls Royce, Ferrari. You- it takes 39 months to get a Ferrari, you know why? It was made by hand.

    26. SB

      Yeah.

    27. SS

      Right?

    28. SB

      Yeah.

    29. SS

      And one of the things that makes it expensive is the technology and the carbon fiber and all that. But the other thing is it's slow and it was made by people.

    30. SB

      Human error, the value of human error.

  5. 18:25 – 19:55

    Skills Needed in the Evolving World of AI

    1. SS

      know?

    2. SB

      What are the other skills that you think-

    3. SS

      (laughs)

    4. SB

      ... we need to equip ourselves with, based on the way that the world is heading? Because with, you know, like the calculator came along and we no longer needed to be able to do complicated maths or-

    5. SS

      Yeah, completely forgotten my times tables. (laughs)

    6. SB

      I can't spell any more. (laughs) I mean, so if I, I said to my friends, "The most I can do is nine times nine."

    7. SS

      (laughs)

    8. SB

      That's, like, the top end of my range. (laughs) But with spelling, it's the same. I get, like, half the word correct now with AI, and it just- (laughs)

    9. SS

      No, no, no. Uh, but, but again, eh, you know?

    10. SB

      So what are those skills if you-

    11. SS

      I think it's all human skills. I think there needs-

    12. SB

      Human skills.

    13. SS

      So I think where the world is gonna 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 gonna suffer. And 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 all two different skills. How do I have an effective confrontation? You pissed me off. Do I know how to approach you as a friend, as a colleague without creating a, a massive fight or losing a friendship over it? Um, how to take accountability, how to express empathy. These skills, these very, very human skills, are the things that we're already starting to see just with the internet and social media, um, are suffering. And so I think AI will only exaggerate the loss of those skills, and those skills are more important than learning how to spell.

  6. 19:55 – 20:45

    Is Universal Basic Income a Solution to AI-Driven Job Loss?

    1. SS

    2. SB

      One of the concerning things was I heard Sam Altman, who's the founder of OpenAI and ChatGPT, launch this thing called Worldcoin couple of years ago when ChatGPT really started taking off, and it has been closely tied to the concept of universal basic in- income.

    3. SS

      Mm-hmm.

    4. SB

      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-

    5. SS

      Yeah.

    6. SB

      ... Sam Altman.

    7. SS

      Yeah. I just, again, I'll go back to my ironic statement before. Isn't it ironic that they wanna do, uh, a universal income, a standard universal income now that the knowledge workers are losing their jobs, but when the factory workers were losing their jobs, th- those same people were massively against, uh, uh-

    8. SB

      Yeah.

    9. SS

      ... these kinds of things? So I mean, yes.

  7. 20:45 – 24:22

    UBI’s Impact on Meaning and Purpose

    1. SS

    2. SB

      What happens to-

    3. SS

      I mean, it's ironic.

    4. SB

      ... purpose and meaning if we're being... 'Cause 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-

    5. SS

      A minimum salary, yeah.

    6. SB

      So, you know, $2,000, $3,000, whatever it might be-

    7. SS

      Yeah.

    8. SB

      ... um, because they don't think many of us are gonna have, there's not gonna be enough jobs to go around. And 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.

    9. SS

      So we're not being given wealth. There's a difference. We're being given survival money, right? And so, you know, you know, we have to be very careful that says, you know, everybody who's on welfare is lazy. You know, that's not true, you know? So 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, who makes a, a commission salary, commission, you know, works on commission, and they make just enough to pay their rent and buy food, and that's it. Like, that's a loss, that's a lack of ambition, you know? The cases, th- for at least the people I've heard talk about it, they make a compelling case for it, especially in a world where there is plenty of wealth, um, but, you know, I don't know enough about it to make an argument for or against it, if I'm honest. Um, but I do find it ironic that the Sam Altmans of the world are calling for it, given the fact that there's gonna be so many job losses when it's jobs of their kind. And, like, I also think that's funny. Like, what's gonna happen when Sam Altman's product gets good enough that he can lay off most of his staff? Just curious what happens.

    10. SB

      He has made a point of having, I think it's 100 people or less in his company. He doesn't have, like, a big team, and I think part of that is because when I heard his TED Talk a couple of days ago, he's saying, "Yeah, I think AGI is sooner than we think actually, and I think we're gonna have a fast takeoff, which means it's gonna ar- arrive very quickly and"-

    11. SS

      Yeah.

    12. SB

      ... "accelerate very quickly." So I think he's actually preparing not to.

    13. SS

      Yeah, but when ha- what happens to the 90 people he lays off when he doesn't need 100, he only needs 10?

    14. SB

      Th- this is the question.

    15. SS

      I'm just curious. I don't know.

    16. SB

      Yeah, no, this is the question.

    17. SS

      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-

    18. SB

      Mm-hmm.

    19. SS

      ... when it's their income on the line, when it's their pride, when it's their ego, you know? I keep hearing from companies... I mean, you, we were talking about this before we turned on the cameras. You know, you know, you talk to, if you want a new website, y- I guarantee you, I d- I don't care which company you talk to, they will all talk about how their AI this, AI that, and 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. And then you ask them for a proposal, it's gonna look like all the other proposals from 2015. You know?

    20. SB

      (laughs)

    21. SS

      And this is how many hours it's gonna take our people to program this and code this, and I was like, "What happened to all the AI?"

    22. SB

      (laughs)

    23. SS

      Why is this slow and expensive when everything's supposed to be fast and inexpensive?

    24. SB

      Because they're taking the margin.

    25. SS

      Of course they're taking the margin, and, and they've got a lot of people doing things the old-fashioned way because the business model... You know, pe- people work very hard to p- The status quo exists because there are people who benefit from the status quo, you know? That's why there is a status quo.

    26. SB

      Mm-hmm.

    27. SS

      And it's, uh... And, you know, like I said, everybody's into change, the future, you know, until it's, until it's them that's threatened-

    28. SB

      All of-

    29. SS

      ... or their, their income.

    30. SB

      The, the billionaires that I, that I know, the one consistent thing they've whispered to me about AI is that...... people are gonna 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

  8. 24:22 – 25:35

    The Uncertain Future of AI

    1. SB

      y- 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-

    2. SS

      Yeah.

    3. SB

      ... whether it's Mustafa, who's head of Microsoft AI, now CEO of Microsoft AI, or people from Google or the CEO of Google, or Reid Hoffman, who's the founder of LinkedIn, they all had different opinions, which made me to think actually the gr- right answer is nobody knows.

    4. SS

      The right answer is nobody- that is correct. And, and, and you always be- be- be aware of the messenger, right? Like, you won't have anybody who owns an AI company talking doomsday scenarios.

    5. SB

      (laughs) Yeah.

    6. SS

      It's not in their economic interest, even if they secretly harbor that. It's like people who s- used to run cigarette companies didn't smoke and let th- they didn't let their family smoke. It's like, I remember visiting Facebook in the earlier days, and they (laughs) ... I went into the cafeteria, and they had, like, like, picnic benches. And I was like ... And they were telling me with pride how they have these communal eating s- areas to help people maintain relationship. And 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 relationship." I mean, the point being, if your economic interest ... You know, show me how someone's paid, and I'll show you how they behave,

  9. 25:35 – 28:13

    The Race for AI Dominance

    1. SS

      you know?

    2. SB

      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. And he said, "By the way, what he tells me in private is not what he's saying publicly."

    3. SS

      Yeah.

    4. SB

      "I," he, he said to me-

    5. SS

      Yeah.

    6. SB

      ... that what this particular CEO thinks is going to happen with AI is pretty horrific.

    7. SS

      Mm-hmm.

    8. SB

      And the CEO of this big AI company is totally cool with it. He, it's pr- it's, and it's horrific what he thinks is about to happen. And then when I watch this guy do his, like, online talks and give his-

    9. SS

      Yeah.

    10. SB

      ... opinion, he's so nuanced, and everything will be fine, and he's an E- 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.

    11. SS

      Yeah.

    12. SB

      Like, actually, the lack of empathy-

    13. SS

      Yeah. That makes sense to me.

    14. SB

      ... and the, like, uh, the obsession with power was shocking to me.

    15. SS

      Yeah. 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, and challenged one of my theories head-on, right? So I talk about in An Infinite Game, you know, Jim, Jim Carse, his theory, you know, in an infinite game, there's no winners or losers, right? And so, like, nobody wins, you know, fast food. Nobody wins cars. Like, General Motors, Ford, Vauxhall, they can all exist at the same time, right? And they'll have degrees of success or not success, but they can all exist simultaneously. No- nobody's gonna win. The exception is in the internet, in, in the, like, like Amazon, it won.

    16. SB

      Yeah.

    17. SS

      Like, you know, Google for search? Yep, they won, right? And if you start going down, like, the big, big tech companies, there is only one. I mean, sure, there's competition, but not really, right?

    18. SB

      Mm-hmm.

    19. SS

      Who, you know, Walmart is making a run of it to threaten Amazon, but Amazon's still so damn big, you know? All of these companies are, there's only one. And that's not good, that you can't have winners in a, in a category. And so this is why I think the, the race for AI is so aggressive, for AI dominance is so aggressive, and which is why people are not being careful and which is why they're not putting controls, is 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? 'Cause I don't think ... it just seems to be the way it is, which is a very scary prospect to me, that the, the fact that we can have winners is, is a bad thing, especially if we, if we pride ourselves on being capitalists, then there cannot be, there cannot be a winner, and there cannot be one that is so dominant that, that nobody else can even compete except for scraps.

  10. 28:13 – 32:20

    AI’s Long-Term Impact on People’s Lives

    1. SS

    2. SB

      What are your emotions when you think about AI and what's happening? 'Cause I, I feel like the moment we're living in is a profound one and that we don't actually realize it. Because when these tools come out, OpenAI released yesterday th- 3.0, it's the best model ever. The day after, my life was the same. So we don't really notice it 'cause we go back to work. Our clients ask for the same thing. We have the same team members sat around us. The, it almost seems like the sand timer has rotated, and we're on a clock, and it's a slow disruption of our everyday lives. Sam Altman the other day on, at his TED Talk three, four days ago said, "In the short term, everything will appear the same." But in the long term, he goes, "Life is gonna be completely different."

    3. SS

      Yeah, I think that's right. I mean, and look at any, any technology like the, uh, like AI. It was kind of the same until it wasn't. And these are evolutions, not revolutions. Like, there's a revolutionary bit.

    4. SB

      Mm-hmm.

    5. SS

      You know? Like, I remember when, when the internet showed up and, like, brick and internet shopping showed up, and all the technologists were like, "It's the end of stores. It's the ends of bricks and mortar. Like, th- done, like, we'll never go to a shop again." Well, that didn't happen. Now, shops struggle to compete against internet, but that's a price thing, right? That's, that's a business model thing.

    6. SB

      Yeah.

    7. SS

      But we like going shopping because again, they've, all of these companies always forget, especially technologists, they all forget that the end user h- is a human being. And most of us don't fully understand everything. Even, even our iPhones, most people use a s- 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, right? Even a, and y- neither do your kids. It's not an adult thing, right? It's not an old person thing. Like, 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, and it's a bell curve. So I think there will be s- 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. I think there'll be a, a revolutionary bit, and then it'll settle. I, I, I'm, I find this whole thing fascinating. When you ask me how do I feel, you know, depending on what subject I'm talking about, absolute fear and absolute amazement.I, I, I have, I have both and, well, everything in between. When I think about how it affects democracy and the ability to make deepfakes and, and how it can manipulate people and their opinions to vote one way or another, I have real fear.

    8. SB

      Yeah.

    9. SS

      Right? When it comes to, like, productivity and the reshaping of business, you know, technologists and people who, who were part of the internet revolution, they love to say, "You know, 20 years ago, 80% of the jobs we have now didn't exist." They love to say that, right? But when you ask them now, they'll, they, like, they'll, uh, they seem to think the... I think it's the same, which is all those people who are gonna lose those jobs in white-collar, you know, in white-collar jobs and knowledge workers, I think, uh, they're not, they're not gonna not work. There's gonna be new jobs. The IRS digitized a whole bunch of years ago, right? They got rid of all the accountants and they put in all the computers, right? Do you know how much money the IRS saved when it, when it changed, completely changed the, the way it looked?

    10. SB

      No.

    11. SS

      The answer is zero. Yes, they got rid of all the accountants and they need to hire all the IT people.

    12. SB

      Mm-hmm.

    13. SS

      So the, the, the, the workforce looked different, but it didn't get smaller. And so I think the same thing. What it's gon- we're, we also, we 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. Go, you wanna get an advanced degree? I don't need you to be a coder. You know, coding was a thing for a... Go be a nuke, 'cause by the way, you gotta be just as smart to be a nuke as you have to be a, a, a, a, a... So you're gonna start to see that. You know, you're gonna see energy work. Um, I just think the jobs will change. I don't think they're gonna, like... I, I completely... One thing I do disagree with, you know, which it's not like you're gonna be a bunch of people walking around bored.

    14. SB

      Mm-hmm.

    15. SS

      I just think the jobs will change.

    16. SB

      If there

  11. 32:20 – 35:14

    Preparing Young People for the Future of AI

    1. SB

      was a, a 10-year-old kid stood here now and the 10-year-old said to us, said, "Guys, what do you think I should focus on?"

    2. SS

      I would say two things. Um, uh, one is, going back to human skills, learn how to be a good friend to your friends.

    3. SB

      Okay, how do I learn that?

    4. SS

      You're gonna really need that. How, does a 10-year-old learn that or how do you and I learn that?

    5. SB

      Both.

    6. SS

      A 10-year-old learns it that when they go and have a playdate at a friend's house, a smart parent takes away all the phones. Uh, 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. That when they have a fight, the parents make them say sorry, you know? Go over to your friend's house and knock on the door and you're gonna say sorry for the thing that you did. Um, we're gonna teach kids how to resolve conflict, we're gonna teach kids how to pay compliments, we're gonna teach kids how to take accountability, and these are all the skills of, you know, "Well, what did you do wrong?" versus "What did your, what, ha- what ha-" You know, like, it's not like, you know... (laughs) It's not always the school or the teacher. Maybe your kid did, is disruptive, you know?

    7. SB

      Mm-hmm.

    8. SS

      And so accountability is a real thing. And so I think if we teach those things to 10-year-olds and to adults, um, I think it makes for a better society, and the other thing is go learn a real skill, and I don't mean like that, you know, prompting isn't a real skill. That's not what I mean. It's what I said before, which is it's the excruciating, like, 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 they know how to resolve conflict peacefully. Uh, by the way, I believe in world peace. I don't believe in a world without conflict. I believe a world in which we can resolve our conflict peacefully without the need to go to war to resolve conflict.

    9. SB

      Mm-hmm.

    10. SS

      This is why I like democracies, 'cause democracies can solve conflict without bullets. So I, the human skills one, but I say a real skill meaning, like, go do something difficult. Build something, design something, imagine something, write something, and, and, and, and by the way, I'm totally fine even if you plug into ChatGPT and say, "Tell me what's wrong with this." Your grammar's all screwed up, you know? And like I said, I- I am smarter because I did it. I'm, the reason I'm more confident than when I was younger, and I think that's one of the things you do, people talk about you get wise with age, you know, and like, and you know, you have more confident as you get older and, and yes, that's all true and there's multiple reasons for it, but I think one of the reasons is, 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, it, uh-

    11. SB

      Yeah.

    12. SS

      ... I know how to do it. I'm not afraid of it anymore. And so 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.

  12. 35:14 – 45:23

    Importance of Gratitude in a World of Unlimited Possibilities

    1. SS

    2. SB

      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 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? And 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-

    3. SS

      Yep.

    4. SB

      ... has gone to basically zero.

    5. SS

      Yep.

    6. SB

      So we can all theoretically from our computers now become movie directors and authors and software developers, and so with this possibility, os- opportunity, and the, the thing we need to deploy is intention, like what do I do? What is the thing that's gonna 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?

    7. SS

      ... now. Right? Like, we, there's something to be said for gratitude, and if you wanna make it money, we know the data on this, right? I think once you reach, I, I can't remember the number, uh, $70,000 a year of income. Like, y- y- like, when you're talking about money can't buy happiness, like, it absolutely buys happiness up to a certain level, which is survival, and then a little bit more, you know? But once you reach a certain level, like, the, there is no discernible increase in happiness that comes with money. Now, what money buys is options, you know? What money buys is time, you know? Um, those things are true. And you, you said it, like, some of the people that you and I know who have made generational wealth, they're not discernibly happy. The ones that are happier 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, th- those were their passions and their cause, and then the money came and they weren't building the thing anymore. And, you know, this, this is, this is the difference. It's like, why... This, this is really interesting. It also gets to the question is, why is it that small companies are more innovative than big companies, right? Like, you think about it. When you say, "What's the secret for, for innovation?" Well, you wanna have resources, you wanna have great people, and you wanna have great market opportunities, and then you can have great ideas. Okay. So, big companies have tons of money, they hire, have all the best people, they have mature, uh, marketplaces that people generally know who they are, and they're the least innovative organizations on the planet, right? Then you have little companies that have no money, they're bootstrapping it, they don't have enough people, nobody knows who they are in those shit market conditions, and yet they're more innovative. And then big companies innovate by buying the little companies. Mm-hmm. You know? That's basically what happens. "My exit." Your exit? Big company can't innovate, so they just bought you. Right. Right? Why is that? Why is that the rule? And so it goes directly to this. I think, I think the reason is, is because when you're small, your ambitions are bigger than the resources you have to achieve those ambitions. Mm-hmm. Every small business has outsized ambitions. Re- re- like, beyond objectively stupid. Like, you look at what they have and what they've got, and you, they tell you where they're gonna be, and you're just like, (laughs) "No." And yet some of them do. And I think the problem with big companies is their ambitions are well within their, their capabilities and their resources. In other words, their vision isn't big enough. Mm-hmm. And 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. And so it goes right back to this, which is if, if, if we can do so much with AI, then we need bigger visions. And 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, um, and 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- Mm-hmm. ... is a profound impact. I went through this with the LA fires. Right? The, 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. And two things happened that were profound that liv- that I will, 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, right? Started by this amazing, amazing, amazing entrepreneur named John Mills. And we were all obsessed with Watch Duty. We all were wa- on this app the whole time, and one of the things we were watching was the wind, 'cause if the wind shifted, it could've profoundly impact your life. And I remember having this experience, like, we were all watching the wind, and the wind went away from me, and I thought, "Oh, thank God." And in that moment, I knew that somebody was looking at the app going, "Oh God, no." Mm-hmm. And it's not like service where I'll eat a little less so that somebody can eat more, or I'll give up some of my income so that somebody has... It's not one of those... I don't want my house to burn down so somebody else's house doesn't burn down. And I has, I had to live with this paradox of how unfair the world is, that simultaneously my relief and good news was somebo- was somebody else's stress and bad news, and there was nothing I could do to change that. So, that paradox, I, it, uh, is horrible, and I, it was, it was right in front of me. So, that's one. But it's the second part which is, the evacuation zones were coming a little closer, and they were one zone away from where, where I live. And we didn't know if we were gonna be woken in the middle of the night with a, with an alarm to evacuate. We didn't know. And so we had, I had to go through the process of packing up my car and making my go-bag, and I put as much stuff in my car as I could. And I had to, you know, we all play that game. It's 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. Right? A lot of people in LA had to do that. Right? You actually had to make the decisions, "What am I gonna take and what am I gonna leave behind?" And I found myself bringing things that I never thought were important to me, and I found myself leaving things behind 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. Like, it just, I 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. You know, I hear this, you know, if somebody loses a parent, they go, "Look, it was awful, and, you know, he suffered as, on his death bed, but I'm glad I was with him to say goodbye." And it was the most amazing thing to have gratitude for something that I don't wanna lose, but accepted that I, I might. Mm-hmm. And, uh, it's made me a lot more disconnected from my materials things-Especially the things I say goodbye to, 'cause I've already said goodbye to them. I had, had, I, I just sold some of my art for, for charity and people said, "How did... You love your art." I'm like, "I know, like, my art's like my babies." Like, they go, "How did you choose?" And I said, "I've already said goodbye to everything here. I did it months ago."

    8. SB

      Hmm.

    9. SS

      You know? And I think this idea of gratitude, gratitude for what we have, but also, um, like, you're gonna lose your parents. All of us will lose our parents. Hopefully, hopefully, hopefully, w- uh, they never have to say goodbye to us, but we... If things go well, we're gonna have to say goodbye to our parents, and we can't be angry about it. We wanna say, "Thank you for the times we had." And I think to have that, uh, level of appreciation for everything in our lives, how temporary all of this is, I think that's... It makes you happier. I know it sounds... I, I... It's... It makes you happier to just look at someone and be grateful.

    10. SB

      Mm-hmm.

    11. SS

      You know? Failed relationships, you could be angry at the other person, or you can be grateful for the lessons they taught you, and, or for the good times you had. And I think to change our minds to gratitude... And you can, you know, it's, it sound... It's a little bit, you know, hippy-dippy to have a gratitude practice, and that's fine, you know, if that's your thing. Lie in bed every night or keep a journal and just say the things you're grateful for. But I don't know if it works without an evacuation zone approaching. I don't know. But to go around your home and just say thank you to the things that you like is a weird thing. How many of us... How many of us... When was the last time you called a friend out of the blue and just said, "Thanks for being my friend." Like, "Hey, just wanted to call and just tell you I love you, and just tell you thank you." And, you know, that's all. No... Just a quick... Just two minutes, just, just wanna say thank you for being my friend.

    12. SB

      I think if I said that to one of my best friends, they'd think I was losing my mind or something, or that something was wrong. They'd be so concerned 'cause it's such an unusual thing for me to- (laughs) to have done.

    13. SS

      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 gonna try it.

    14. SB

      Yeah, that would make sense.

    15. SS

      Then you can do that.

    16. SB

      (laughs)

    17. SS

      You know? I'm, I'm new to this, you know? I, I know for years people have been like, "You should have a gratitude practice, keep a gratitude journal." And I tried it. I was like, "Okay, uh, I'm grateful for my sister, grateful for what I've, um, for my family, grateful for my friends, grateful for the life that I live. All right, goodnight." All right, next day. "I'm grateful for my sister, grateful for my family, grateful for my friends." You know? And I found it so repetitive that I was like, "Is this worth it?" Like, sure, like, every now and then something was different and new. And I've come to, come to the conclusion, like, if it's the same three things every single day, good.

  13. 45:23 – 47:50

    Importance of Relationships

    1. SS

    2. SB

      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 a billion dollars could cure their sickness. Like, who would you cure it for? Would you, would you spend a billion dollars to cure-

    3. SS

      Right.

    4. SB

      ... your, your girlfriend's sickness, your, your mother's sickness, your father's sickness, your whatever? Even if it was, the, the, the risk to them was, was low?" And you would. I'd give every pat- penny I had-

    5. SS

      Of course.

    6. SB

      ... 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. And 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.

    7. SS

      I, I, uh-

    8. SB

      And how much I neglect them.

    9. SS

      Yeah, I mean, th- th... Like, of course. I mean, we are, w- only when it's... And it's... You're right, like, which is if you say give a billion dollars and you can cure this disease that affects, you know, two million people, 10 million people, you'd be like, "Eh, I'll give some money." Right? But if it was one family member, you would exhaust every resource, you would quit your job, you would do everything you can to-

    10. SB

      For a 1% chance.

    11. SS

      ... for one, for, for a 1% chance.

    12. SB

      Yeah.

    13. SS

      You know, and people do. They quit their jobs when... And, and, and be... And, like, so many charities have been started because my father died, my mother died, my sister died, my brother died, and now I've devoted my life to... Right?

    14. SB

      Mm-hmm.

    15. SS

      Like, like, literally that's the reason. And it's because it's personal. Of course, that makes sense. It's why, why are some entrepreneurs good and some entrepreneurs bad? Well, how personal is the thing that you're working on to you? Because then I only like to... Like, the entrepreneurs that I love, I wanna know that they are solving a problem that they struggled with or that somebody they love struggled with, or something. If they, 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-

    16. SB

      Yeah.

    17. SS

      ... and power only. I wanna know somebody that is s- it's so deeply personal to them that they will stop at nothing. They will run through a brick wall and find every creative solution, and it goes right back to the small company versus big company. It's, it's passion and a vision that is bigger than the resources that I have. Which, you know, I had a conversation with somebody recently actually, where they wanted to, uh... I, we, we, uh... It was a business problem, and they wanted to change the goals.

    18. SB

      Mm-hmm.

    19. SS

      And I said, "We can't just change the goals because they're difficult, you know?

  14. 47:50 – 48:54

    Importance of Failure

    1. SS

      So we might miss the goal." It's true, 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. "I don't like to fail, and I know you don't either." And I said, "Ah, that's where you're wrong. That's where you're wrong." I have spent most of my life a failure, and I'm very comfortable being a failure. And I think of myself not as a success. I think of myself as a failure, and that's because my ambitions are bigger than my skills or my ability to achieve those ambitions. And so almost everything I've done, with a couple of exceptions, have fallen short of what I had hoped for.

    2. SB

      Mm-hmm.

    3. SS

      I'm very comfortable with that, because failing at 80% is really much better than succeeding at 30%.

    4. SB

      (laughs)

    5. SS

      And I think this idea of fear of failure and embracing failure, I don't wanna fail.But I just, I, I have, I think it's important to have dreams that are beyond your skills or your resources, because that's where creativity comes from, that's where resourcefulness comes from.

  15. 48:54 – 53:39

    Learning Through Experience and Resourcefulness

    1. SS

      You know, when you go, "How am I gonna figure this one out?" And you told me the stories of your own team.

    2. SB

      Mm-hmm.

    3. SS

      You know? It's the resourceful ones. And now we go back to AI. AI is not gonna figure that out, right? There's, there's data on this. I, I've actually never thought about this. This is good. There's a book called... Oh, it was The Wisdom of Crowds.

    4. SB

      Mm-hmm.

    5. SS

      I think it was that one. I think it was The Wisdom of Crowds by James Surowiecki, where people with experience knew what to do versus people who were just trained. So, I'll give you the example. This is, I kind of... And again, I might have the book wrong, but this was, I remember the case. So there was a, a bunch of firemen fighting a fire in, like, the, in... Wildfires, right? And the wind picked up, and the fire was coming really fast towards these firemen. True story. And they all started running for their lives as this fire was approaching them unbelievably quickly. But the problem was, they looked ahead, there was a small hill, which means you're gonna slow down, 'cause you can't run fast up a hill. And this fire is coming fast, right? The senior guy on the, 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. And 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 h- it, it was accumulated knowledge of wisdom of, that came from experience, that he knew the right thing to do in the moment. He was able to read the tea leaves and away. And his, his gut, whatever that means, his gut said, "The right thing to do is to drop down. You'll be okay."

    6. SB

      Mm-hmm.

    7. SS

      And this is why, I'm gonna sound like a, a broken record, the importance of doing the work yourself, of writing the book, painting the painting, choreographing the dance, you know, composing the symphony, building the business, having the difficult conversations, stumbling and bumbling, right? The reason for it... Uh, like, let's say you have a fight with your, your, your girlfriend. You don't wanna be in a fight. You don't like being in a fight. You wanna do the right thing. So you go to ChatGPT and you be like, "My girlfriend and I had a fight. This is what the fight was about, okay? I think I did some stuff wrong. I think she's 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 wanna take full accountability. I'm really, I'm, 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 gonna go?

    8. SB

      (laughs)

    9. SS

      Right? Now, you did everything right. 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 everything you said about the job interview. It's everything you said about all those other things, about all the resumes, all of the pitch decks. It's not you telling me sorry, it's ChatGPT telling me sorry. And 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." You know, and then she fights with you because you get it wrong, and you rumble through it together. And what happens when you come... You've had this happen. I know, because I have, and I know any- body, everybody has. When you come out of the fight, you're closer.

    10. SB

      Mm-hmm.

    11. SS

      Not 'cause you got it right, because you got it wrong. And if you learn the skill, and you get better and better and better and better, and you do learn the skill of saying the right thing, and you do learn the skill, 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 gonna happen, because you're equipped for this relationship.

    12. SB

      Mm-hmm.

    13. SS

      And it's that investment in the relationship rather than trying to transactionally solve the problem before me. And that's the difference.

    14. SB

      Mm-hmm.

    15. SS

      It's infinite versus finite. It's transaction versus... It's destination versus journey. I'm in the journey of this relationship versus I have a destination, I gotta solve this problem now, otherwise this is gonna destroy my relationship. And all of this is coming full circle, and it comes right back to everything we started as. I think it's hilarious that you and I... That you're having a conversation with me about AI, 'cause I'm not an AI expert and I'm not in the AI business. But I, I am in the humanity business, and I think everything we're talking about from every angle, we're battle testing this idea. And what we can't get away from is human beings really want human beings.

    16. SB

      Mm-hmm.

    17. SS

      And human beings really want human experiences.

    18. SB

      Mm-hmm.

    19. SS

      And human beings really want things made by human beings. And we are not only okay with, we want imperfection, because imperfection is the sign of human.

  16. 53:39 – 55:33

    Why Struggle Is a Good Thing

    1. SS

    2. SB

      I was just thinking about how, 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 pu- without emotion, without expression, and if she was spewing ChatGPT-like responses back at me, it would, it would be a little bit infuriating-

    3. SS

      Yeah.

    4. SB

      ... but also, it would be completely dehumanizing, as you say. And it's funny how actually, even in conflict, I want emotion-

    5. SS

      Yeah.

    6. SB

      ... I want imperfection-

    7. SS

      Yeah.

    8. SB

      ... I want res- human resonance. So, it's interesting, 'cause I've been, like, thinking about what my thesis is.

    9. SS

      Struggle is a good thing.

    10. SB

      Yeah.

    11. SS

      And I think in our modern day and age, we have underappreciated and underrepresented the value of struggle. And if you ask anybody in their life, you know, "Tell me about a time in your career where, like, 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. (gasps) Oh my god, it went so badly, and yet..."... the way we came together. Like, the most important thing in my career was when I lost my passion and went into deep depression. Never wanna go through that again. Really glad it happened. And all of our relationships, professional, personal, romantic, whatever they are, right? All of our relationships get better when we go through struggle together. And we know, 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, a natural, a nat- uh, a natural disaster, like 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." Right? Like, we can put aside all the rational nonsense, the, the, the intellectual nonsense, and at the end of the day, human beings are, are, are good at helping human beings.

  17. 55:33 – 59:25

    People Buy the Story, Not the Product

    1. SS

    2. SB

      Struggle also, in many contexts, is the value. So 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 that we talked about earlier are valuable is because of the pain and the toil that went into them. And 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. And actually, the investment is the value, like the-

    3. SS

      Yeah.

    4. SB

      ... the amount that went in the top creates great value.

    5. SS

      We're not buying the product, we're buying the story.

    6. SB

      Yeah, like the Mona Lisa is-

    7. SS

      You're not buying 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.

    8. SB

      And the Mona Lisa was stolen, from what I understand.

    9. SS

      I mean, we don't even know if the, the one in the Louvre is the real one.

    10. SB

      'Cause I heard much of the, the reason why the Mona Lisa is so valuable is because at one point it was stolen, and then they, like, managed to r- find it again. And actually, it's just a painting, but the story of the painting-

    11. SS

      Yeah, the story is amazing.

    12. SB

      ... is worth 100 million, 200 million, whatever.

    13. SS

      Whatever. I mean, and so this is what we fe- The reason famous artists are famous is 'cause you buy the story of that artist, not, not their talent. There's a lot of famous singers and actors and painters, dancers who are a lot less talented than the unknown ones-

    14. SB

      Mm-hmm.

    15. SS

      ... but you buy into the story. And this is why some celebrities, as much as they talk about the paparazzi and the tabloids, they wanna be in the paparazzi and the tablo- They want the paparazzi to follow them because it keeps their story relevant. It keeps them, you know... They're worth more because they're in the zeitgeist.

    16. SB

      Apple know this better than anybody, 'cause you go to an Apple store, and they've laid out their products as if it was an art gallery. The three feet either side of the iPhone create the impression in my mind that there, this is a piece of art and there's only one of them. And 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 1,000 iPhones, like the old electronic stops 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 that, "Oh my God, this thing is..."

    17. SS

      It's theater.

    18. SB

      It looks like one of one.

    19. SS

      Yeah, it's theater. And, and some would call it manipulative, but we want things to feel valuable, not just be valuable, right?

    20. SB

      Mm-hmm.

    21. SS

      I could tell you I've got a, a... I've, I can... I, I, I found a guy who makes cashmere jerseys, and he uses the exact same cashmere as, you know, Loro Piana or whatever, some fancy, fancy-ass brand, you know? But the problem is, it says, like, "Dave's Cashmere Shop."

    22. SB

      (laughs) Yeah.

    23. SS

      You know? I could tell you everything about where he sources the cashmere, how he makes it, that it's the same everything, and you'd be like, "Yeah, Dave's Cashmere Shop?" 'Cause you're not buying the cashmere, you're buying the brand. You're buying the story. You're buying the association. That's what's, that's why brands have value, because it's irrational.

    24. SB

      Yeah.

    25. SS

      And humans are irrational, and that's why companies invest in building brands, for the story. And so... Yeah, I, I think I'm... You know, as much as chat... uh, uh, AI scares me, I still believe the thing that the technologist, the technologists don't appreciate and won't appreciate, and there, there will be a rebellion. And handmade will become more valuable and handmade will become more expensive, and people will wanna say that. You know, it's like, "You had that person write your speech for you? You had..." "Wait, who did the painting for you? They, they did it themselves?"

    26. SB

      Mm-hmm.

    27. SS

      You know? And I think that's good. You know, it's a pendulum, right? We're gonna get enamored with the technology until we're... until it's boring.

  18. 59:25 – 1:02:24

    Scale Breaks Things

    1. SS

    2. SB

      This also just expands generally. I know this sounds quite big and we're talking about these big things, but just 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, a presentation deck at work. But actually, I'm, I'm already noticing, I'm attributing huge value and interest in things that I can identify as human-made. It, it... I had a flashback a second ago as we were talking about this idea of scarcity to one of my favorite brands in the world. It's a clothing brand, and I was obsessed with this clothing brand. I'd spend a huge amount of... I don't spend money on clothes. 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 like a, 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. And in that moment... (fingers snapping)

    3. SS

      Fell out of love.

    4. SB

      I fell out of love.

    5. SS

      Exactly.

    6. SB

      Because in my head, I'd painted this, like, artisan picture of, of them sewing it, these two guys sewing it in their bedroom, and then, like, sending it to me. (laughs)

    7. SS

      Probably that's probably what it, it's probably what it was on the ad, too. Probably showed a-

    8. SB

      I think that's what it kind of, like, used to be, so I still had that image, but then it got so big.

    9. SS

      Yeah, but it got too big. Yeah. One thing that I've always understood, this is true for businesses, this is true for absolutely everything, scale breaks things.You know, scale breaks... In the, in the military, they have, they have special forces, special operation forces, Navy SEALs, SAS. You know, all those folks, right? And there's a, there's a saying in the special forces that basically, um, special... "You can't scale special." Right? So you can take whatever training, skills, whatever you have for the special forces and you give it to everybody, it's not gonna work. Special can only be small.

    10. SB

      Mm-hmm.

    11. SS

      You know? And, and so scale breaks things. Scale always... So I mean, like, Microsoft versus Apple, right? So Apple wanted the highest quality operating system in the world, right? So what did they do? They, they refused to clone, right? They wouldn't, they wouldn't, they wouldn't clone their, their operating system, and they, uh, as a result of, of refusing to, to do that, they, they never... Uh, for years, Apple had, like... In the height of the c- the PC wars, 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, it was a little bit different on IBM. Wherever you used 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.

    12. SB

      Mm-hmm.

    13. SS

      Every time. There's a reason why buying fancy goods for a lot of money, like... Because, as you said, the way you make things has to change, and you have to start making them in factories, and you have to... Scale, scale br- spr- scale breaks companies. Think about how beautiful companies are. The number of companies that talk about, "Oh, 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.

  19. 1:02:24 – 1:03:29

    Ads

    1. SS

      (page turns)

    2. SB

      I think B2B marketeers keep making this mistake. They're chasing volume instead of quality, and 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. And I know, as there was a time in my career where I kept making this mistake, that many of you will be making it too. Eventually, I started posting ads on our show sponsors 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 to, not only to think and learn, but also to buy. And when you market your business there, you're putting it right in front of people who actually have the power to say yes. And you can target them by job title, industry, and company size. It's simply a sharper way to spend your marketing budget. And if you haven't tried it, how about this? Give LinkedIn Ads a try, and I'm going to give you $100 ad credit to get you started. If you visit linkedin.com/diary, you can claim that right now. That's linkedin.com/diary. (page turns)

  20. 1:03:29 – 1:05:18

    Self-Love as a Key to Successful Relationships

    1. SB

      Is it harder now to find love? 'Cause there's lots of stats that say we're having less sex, we're lonelier than ever before. Um, interestingly, this is maybe an adjacent point, but I was looking at Bumble share price. I love... The founder of Bumble, the CEO, is really, really good friend of mine. I think she's amazing.

    2. SS

      Whitney?

    3. SB

      Whitney, yeah. Sh- I think she is amazing

    4. SS

      Has she come on?

    5. SB

      She has. And 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, you overlay that with some of these other dating apps, and you see... I mean, this is the-

    6. SS

      Well, she's had to come back.

    7. SB

      She's just come back in yet to turn the company around. And actually, interestingly, I saw her do an interview, which is one of these ones here. And in the interview, she says she's gonna revamp Bumble-

    8. SS

      Yeah.

    9. SB

      ... to make it not about finding love with others, but f- falling in love with yourself.

    10. SS

      Yeah.

    11. SB

      And there's also gonna be this dating marketplace, but her first objective is gonna be get people to love themselves-

    12. SS

      Yeah.

    13. SB

      ... through coaching and all these kinds of things on the app, and then find a partner.

    14. SS

      Sure, yes. I mean, I, I agree with that. I mean, it's like, it's... I mean, we're all broken records, right? And I don't mean that as a, like a, like we're all broken souls. Like, you know, y- 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. And look at failed relationships, right? Where there's so much tension. It's somebody's lack of self-love that contributes to the failing of that relationship. I mean, I have a l- dear friend who's going through it right now. She just can't find love, and she... It's, it's just... But it's 'cause she doesn't love herself, and, and she knows that, you know, it's a hard thing to do. So if Bumble can crack that code, more power to 'em. It's, it's a... But this is the problem with a lot of these things, you know. They're common

  21. 1:05:18 – 1:09:02

    Why Wrong Is Easier

    1. SS

      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 that we're supposed to, like, hold space. Everybody know, 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 wanna get into shape, "Hey, Simon, how do I get into shape?" Easy. Every single day, work out for 20 minutes. Every single day. Okay? 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. And 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 That Last. I can help you embrace the infinite mindset and have this incredible calm in life. And the reason most companies won't do it, this innove-... This is a book for innovation, right here. You wanna know, innovate, 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 obs- so obsessed with the result, that we've completely ignored the value of the journey.

    2. SB

      Yeah.

    3. SS

      And people would rather hit the number at the end of the year than build a good, strong company. Think about it, right?If I meet another entrepreneur, when I say, "So tell me about your company." Like, "We're hyper growth. We're a hyper growth company. We're a gazelle." Right? Like, show me... Then I always say the same thing, 'cause 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 (laughs) . And so why are we so obsessed with high speed growth? It's because our investors want us to be obsessed with high speed growth, right? Or our egos want to b- us to be obsessed with high s- high speed growth. Right? And if high speed growth happens by accident, that happens for many of the unicorns.

    4. SB

      Mm-hmm.

    5. SS

      Right? 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. And we're all so obsessed with speed and immediate results. Uh, present company included. I've had to learn this the hard way, that I think there's something joyful and beautiful about slowing down, saying thank you, reprioritizing friends. It's okay. I mean, by the way, cellphones and s- uh, so r- Uh, but before cellphones, we went to work, and then we went home, and we didn't do work at home because we couldn't do work at home-

    6. SB

      Yeah.

    7. SS

      ... because we didn't have computers at home, and we didn't have cellphones or people to call us. And so you, you did work at work, and then you left. And I remember when cellphones started. I remember the advertising. AT&T had this campaign that they showed people working on the beach-

    8. SB

      Mm-hmm.

    9. SS

      ... you know, with their computers.

    10. SB

      Yeah (laughs) .

    11. SS

      I mean, this is, like, the future, right? And they said, "Now," um, well, I don't reme- what was the, what was the tagline? It was really funny. It was like, "Now you can leave work." Right? And that's not what happened. Work came with us. We never left work. Work came with us wherever... This is the problem with cellphones and computers and the internet, which is we do not leave work. Work is with us in our pocket every day, every vacation, every evening, every weekend.

  22. 1:09:02 – 1:11:05

    Friction Creates Freedom

    1. SB

      As you said that, I thought, "Do you know what? That's so interesting."

    2. SS

      Hmm.

    3. SB

      Because that kind of means that friction c- creates freedom in that regard, if you know what I'm saying. So 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 kind of wait for things, right? So 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-

    4. SS

      Yeah.

    5. SB

      ... using the phone in my pocket. S- the friction has come down again, and therefore the pressure to do it now, because I can do it now, goes up. And this is kind of maybe what I was alluding to earlier on-

    6. SS

      Yeah.

    7. SB

      ... in the, you know, when I was thinking about-

    8. SS

      It's good.

    9. SB

      ... how you're gonna get more stressed and more overwhelmed and-

    10. SS

      That's good.

    11. SB

      ... more isolated.

    12. SS

      But that's so good. That's s- Right. It's, we're taking work with us. I mean, it's like, you know, the n- Everybody has a story of, like, where the battery ran out on their phone and they ended up having the best night.

    13. SB

      Yeah.

    14. SS

      Or the internet went out at work and they actually got more done. Like, you hear these stories all the time-

    15. SB

      Mm-hmm.

    16. SS

      ... you know? That, that when, when we're forced not to take work with us, forced, it s- takes a bit of time sometimes to relax, but it's always better because you learn to s- stop worrying, stop checking, you know? You know, and you just... I, one of the things I did, I, I, I can't delete Instagram completely, as much as I'd love to, but I hid it. So you know you can do that on iPhone?

    17. SB

      Yeah.

    18. SS

      You can take it off the c- It's gone. It's hidden.

    19. SB

      Yeah.

    20. SS

      It says hide app, and then I, and when you go into the search, you know when you go search-

    21. SB

      Yeah.

    22. SS

      ... it suggests? I took it off the suggestions, which most people don't even know you can do that. So I took it off the suggestions so when I go to... 'Cause I realized what I was doing is I'm like, when I'm bored, I just pick up my phone, and I just like, and then I see Instagram, and like, and I just click it like a, like a zombie, and then I'm done for an hour, you know? So I hid it. So the only time I go to Instagram is when I have to go to it and I have to type in I-N-S-T, you know? And then it pops up. And my usage of Instagram has plummeted.

    23. SB

      (laughs)

    24. SS

      Plummeted. Because it has to be intentional, and the problem with most social media is it's unintentional.

  23. 1:11:05 – 1:13:32

    Building Community in the Age of AI

    1. SS

    2. SB

      One of the big things, t- talking about community, Instagram, AI, that I think a lot about is, is... Is the value of in real life community gonna rise? And I think we might be on the precipice of the community revolution. I say this because when I think about what's gonna remain in a world where creating things goes to zero, like when... You know, once upon a time m- if you made a social network or if you m- built an app or if you built a medi- a movie or a media company or a podcast, that was half of the job, and the other half of the job was, like, getting it out there in the world.

    3. SS

      Yeah.

    4. SB

      And so now the people that have the other half of the job, which hasn't gone to zero, now have this tremendous advantage 'cause we can all create, but we can't all distribute. And so having community and building and fostering community I think now is one of the things that remains. What are the values of community? Like how do I build a community?

    5. SS

      Well, I have a definition of community-

    6. SB

      Okay.

    7. SS

      ... and I think we said it before, which is a community is a group of people who agree to grow together.

    8. SB

      Interesting.

    9. SS

      Community is a group of people who g- agree to grow together, and I believe friends are at least two people who agree to grow together.

    10. SB

      In marketing, this is the absolute obsession at the moment, community-run clubs and-

    11. SS

      Yeah.

    12. SB

      ... brands becoming, um-

    13. SS

      It's offline is the new online, right?

    14. SB

      Mm-hmm.

    15. SS

      Um, offline's the new black. Um, like there's a, there's a company called Clix, and it was started by v- sh- uh, she's a talented entrepreneur, and she was in college, and she suffered severe depression and loneliness and literally struggled, didn't know how to make friends. And, uh, she... Well, I'll just call her by her name. Her name's Alix. Um, but, uh, her, her company Clix, she started it to solve her own problem, right? My favorite kind of company. And basically to help her friends at school, quote unquote friends, people at school make friends, and 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 or... Just, like, it didn't matter what the reason was. Come and... Just a reason to come that made you, that when you saw the ad hung up on a piece of paper at college, you know, that you'd be like, "I like..."... horror movies, whatever. "I like baking. I'll go to that." Right? Just a- a trick.

Episode duration: 2:06:15

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