How Diary of a CEO became YouTube's #1 Show (Live at Press Publish NYC)

0:00He's the host of the second biggest podcast in the world, the number one podcast in Europe, and the fastest growing video podcast channel globally. Everybody, please, please give a warm Press Publish NYC welcome to the host of Diary of a CEO, Stephen Bartlett.

0:27Whether you know it or not, professionally, as a creator, you are being disrupted now. Your competitors won't do it. They'll look at that small pebble and go, not that one. So there's a particular 10 second change we made to our podcast on YouTube, which had a 300 % impact on the amount of subscribers we get. We've always kept it secret, but maybe I'll talk about it. This conversation is from Press Publish NYC, our event where we hosted over 400 professional creators to talk about the future of the creator economy. Stephen was our last guest of the day and a surprise for everybody in the room.

1:00If you want to get a recap of this session, as well as every session from Press Publish NYC, Microsoft Copilot put together the key takeaways from all the sessions. The link for that is in our description. All right, now for our conversation with Stephen Bartlett of Diary of a CEO.

1:33I don't think I've ever seen you in a white shirt. That's so true. I said to my team, people are going to think I've lost my mind. But no, we've just been recording all day, so it was the only shirt that was in the studio. So, sorry. Well, dude, thank you so much for coming. I really appreciate it after recording all day. So I've been holding this question since two times ago when we saw each other. Do you know this? Okay, I'm going to say it. So Stephen and I are talking in LA, and I don't even know how this came up. But in the middle of the conversation, Stephen goes, oh, yeah, but my failure team does that.

2:08And I paused for a second. I said, what did you just say? He said, oh, my failure team does that. So I've been waiting to ask you about what a failure team is and what they do at your company. Yes. So I think really important. I actually think if there's one principle or idea or concept that underpins the relative success that we've had on our show, it might be this, which is, okay, so the background context and the thinking underneath this is to understand the correct answer to anything in life, whether it's in your marriage or relationship or on your Instagram page or TikTok or whatever it must be, you need to get information.

2:48So the next question becomes, what's the best way to get information in a world where the correct answer is changing at an increasing speed? Like if you listen to some of the futurists out there, they say that if you're 40 now, by the age of 60, you'll experience a year's change at today's rate of change in about 11 days. Things are getting faster. That's what history shows us. So to think that you're going to get the right answer to the key questions you have about your products, your business, your audience, whatever, from reading a book that takes two years to publish and another year to write is not smart thinking.

3:20You're also not going to get any of the right answers from someone like me. Because by the time I've made it up onto stage and then you've implemented it for yourself, the blueprint has probably somewhat expired. So the best way to get answers to the questions that matter to you is to increase your rate of experimentation and failure. Like, and we all intuitively know that run an experiment, failure equals feedback, feedback equals knowledge, and knowledge equals power. But when you look at how the world's best companies are built, that's exactly what they do. They kill the guesswork. They build systems to ramp up their rate of failure so that they ramp up their rate of relevant feedback.

3:56And so when you look at a company like Amazon, for example, Jeff Bezos says in his shareholder letters, in order to be the company we want to be in the future, we have to be the best place on earth to fail. And the crazy thing that happens is you'll all relate to if you've ever worked in a big business or really even a big team before, is as people achieve things and they have more things to lose, the psychology shows they go risk off and they go into loss aversion. They experiment less, get less innovative. And that's the start of the end for those people, those creators, those companies. So if we're going to be successful because we had a high rate of experimentation, how do I maintain that and increase it when all the incentives suggest that we should go risk off?

4:38And that's why we have an experimentation and failure team. We have a head of failure who leads that team called Grace Miller. And her primary objective is to increase the rate of failure. Notice I'm not saying the rate of success, because if it's an experiment, you don't know the outcome. So you don't incentivize people based on how it's going So that's not in their control. The controllable part is, can we run more experiments? So that's what you incentivize. And if you start messing around with the output, you'll disincentivize productive behavior. So that explains it. And like, what does this mean in reality?

5:15It means this team is responsible for making sure that all of us in all the teams production, you know, if I'm talking about like the podcast business, production, the thumbnail team, it could be the e-commerce team, it could be the recruitment team, are constantly culturally ideologically driving the rate of experiments. If they've got any issues, if they've got questions that they don't know how to answer, if the experiments they're running aren't scientifically rigorous, so they're changing too many variables and we won't be able to trust the results, they create rigor across the board and they report on how much we're driving experiments and they do experiments themselves.

5:51So, you know, one thing that springs to mind, just because it's such a big thing for everybody in this room in a world of AI, is language, for example. So many years ago, about a year and a half ago, we first started doing the podcast in multiple languages before multi-language audio. We started doing it with Spotify. And it's taken them about 12 months of experimentation, but we figured it out. And now the AVD in other languages is higher than English, which is like slightly offensive, but whatever. Yeah, that's amazing. I've never heard it positioned like that. And I think that's it. It's a fascinating quest to try and disrupt yourself in some ways.

6:33Right. Or to try and kind of suggest that the goal is to get it wrong as many times as possible, because that's how we get it right. I loved what you said the first time when you said disrupt yourself, because that's like entirely the game. Like whether you know it or not, professionally, as a creator, you are being disrupted now. And the only outstanding question is whether it's you disrupting yourself or some other kid who doesn't have the loss aversion, doesn't have anything to lose, is naive, so they didn't know what convention and the blueprint looks like. They're currently killing you. So, like, doesn't it make a lot more sense?

7:06Like, isn't it like the bulldozer is coming? The driver is yet to be determined. I want to be the driver of my own bulldozer. And so we actually have another team called the FlightX team, which is in part part of the experimentation team, part of the data science team, who are operating kind of like an island. And they're running things like the AI podcast experiments where they're taking my voice, creating end-to-end podcasts using my voice, AI doing a lot of the transcripting, and then trying to see if they can beat the human shows that we have. And again, really remarkably, like you'd think, like most of you won't believe what I'm about to say, which is fine but um it took us about nine to 12 months to get to the point where if i showed you all of the retention graphs of two human episodes the diary of a ceo and our ai one you wouldn't know the difference you wouldn't be able to tell me which one was ai based on the retention graph because the same amount of people are getting to the end and um in in innovation and through history if you read books like the innovators dilemma the reason why people don't pursue the disruptive innovation like AI content creation is because it starts worse and none of your customers or audience are currently asking for it.

8:18So you ignore it. Like the horse and carriage CEOs in the 1800s ignored cars because none of their customers asked for cars. Why would they? They wanted more comfortable carriages, faster horses, stronger horses, and horses that had more power. But through history, whether you look at digging excavators or micro discs or the horse industry, the thing that kills you always starts worse and no one's asking for it. But the thing you have to look for is basically the rate and how much headroom it has to improve. And with AI podcasting, you go, you know, how much headroom does that technology have to improve?

8:55Is it going to be cheaper than human podcasting? Is eventually it going to be better understanding what is retentive? Is it going to be faster to make? Am I going to have to build a studio, fly in a crew? Or am I going to be able to make it maybe automatically within seconds? And so the headroom of growth is bigger. So you're really betting on the rate of improvement and the space for improvement. So, you know, like, obviously, I love what I do. So I'm romantic like we all are about what I do. But I'm also like romantic about winning. And so you have to be less romantic about being right. And they're like very different things.

9:30Being right and winning are very different things. and you have to make sure that you're romantically attached to winning, not being right. Romantic about winning. You have to be, or else you'll get caught up in, like, you'll hang on to the wrong horse. Can you explain the difference between being right and winning? A hundred percent. Okay, so I say this a lot to my founders and my portfolio, my investment portfolio. Being right is your initial hypothesis of how you either thought things would play out or you wanted them to play out is validated. And in my first company, a company called Wallpark, when I was 18 years old and dropped out of university, I had this very clear vision that students would use my student notice board on wallpark.com.

10:11And I was trying to figure out, I had no money, so I was trying to figure out how you drive traffic to a website. So I started all of these Facebook groups more than a decade ago for every single university. And when freshers, freshmen, came to one of the universities in the UK, they would join my Facebook groups. And then, because I was so romantic about them doing it over on my website, I shut the Facebook groups and pinned a post and said, I know you guys are like loving these Facebook groups. And there's like a message every 10 seconds. Now go do it on my website. Okay, that's romance. And no one came.

10:44Like a couple of people came. But no one came. And so I reopened the Facebook groups again and everybody started doing the thing. And then I'd shut them down and say, go to my website. And nobody came. Eventually, I ran out of money. like this process of me trying to force people to do something they didn't want to do because I was romantic about the solution um I ran out of money and so when I ran out of money I thought fuck it shut down the website and I will focus on social media and it turned out that like when I had no fight left in me that built a really big business called social chain which went on to become this big public company and made hundreds of millions in revenue all those things and it was when I like gave up the fight of my own romance and preconception of what the right answer was.

11:24And, you know, and this is kind of what I mean by AI, with the AI podcasting example, I'm going to be unromantic about the solution. If people want to get their information from an AI podcast, that's, I'm going to be, I'm going to be, I'm going to be attached to what the customers want, not what I want them to want. And they're very, very different things. I actually think most of you will need to go through a wall park style example that I've just described to truly understand how romantic we all are about our ideology and our identity and the university degree we got and how that makes us feel around our parents at Christmas time and how that anchors us in this identity which then anchors us to these solutions which can trap us and can mean that we don't see the correct answer when sometimes it's right in front of us and like I could make the case to you about how profound and disruptive AI is to everybody in this room.

12:19And some of you will believe it. And then there'll be another group of people that I think will be, will go through the cognitive dissonance, which is a term that psychologists describe when new information conflicts with who you are and what you want to be true. And the psychologists have proven that you have to dismiss one of these things. You have to dismiss the new information or your own identity to create comfort. And it's very hard to dismiss or to rewrite your own identity. So the smoker who wants to be healthy, who's told that smoking is unhealthy, will say, yes, but smoking helps me with stress or yes, but that's an attempt to alleviate.

12:58That's what most people will do. I've tried over time to be principled and not romantic. I want to ask you, and I want to take a little bit of a step back because I'm listening to you and Samir and I have had a podcast since 2016. I've never once thought about a failure team, being romantic about winning, about being as analytical as you are. And I want to ask you a question that was actually the first question you asked Casey when Casey was on. You said to him, what do I need to know about your earliest days that informs me about who you are today?

13:33All right, before Steven answers that question, I want to answer a question that a lot of you guys ask us, which is how do we research for our guests and how do we come up with the questions to ask them? Recently, we've been using Microsoft Copilot, which is the sponsor of this episode. We've been using Copilot to research our guests and we asked Copilot about Stephen Bartlett. Specifically later on in the episode, you'll see we asked Copilot for questions that Stephen Bartlett would ask Stephen Bartlett. So one of the most unique things about Copilot is actually that you can create a podcast out of the research.

14:05So I just asked Copilot to make me a podcast podcast, researching Stephen Bartlett and giving me some angles on what the conversation could be. I'm going to play a little bit of that for you. Today, we're diving into the fascinating story of Stephen Bartlett, how he went from recording podcasts under a blanket to becoming one of Time's 100 most influential creators. It's not just the information, you're actually getting it in an entertaining way. So this event that we hosted Stephen at Press Publish NYC was also powered by Copilot. And one thing that Mustafa, the CEO of Microsoft AI said, is that voice is going to be the primary way that we engage with AI in the future.

14:41So they built a co-pilot booth at Press Publish NYC where creators could go in there, get feedback on their ideas, research new topics, and do all of this just by talking to co-pilot. At Press Publish NYC, co-pilot was actually the official note taker and recapped the most important things from every single session. And if you want to get all of those notes, we put the link in the description. So thanks again to Microsoft co-pilot for sponsoring this episode, empowering press publisher nyc now back to our conversation with stephen bartlett okay so the big picture thing so a lot of shame i was born in africa moved to the uk when i was a kid we were like the black poor family in our area and in 1994 there wasn't really any other and really any other black families in the southwest countryside of england that plays a role because it makes you i think have an over index towards like validation and fitting in and being like your rich middle white class friends and relaxing, chemically relaxing my hair and wearing the skinny jeans and listening to like Arctic Monkeys, even though I had no interest in the Arctic Monkeys and still don't.

15:40But, you know, I respect them. And what else is important? Really bad in schools, like couldn't pay attention. Turns out I have ADHD, which like apparently is obvious now, but I'm more like, it doesn't mean that I, it means that I get like a really obsessively focused on things. I thought ADHD was like, you can't pay attention to anything, but actually it's, I can't pay attention to things I find really boring, which means that in school I was expelled, then they unexpelled me because I made the school a lot of money. My headmaster was on a TV show in the UK and said this. He said we unexpelled him because he made the school a lot of money, because of my free time I was running these businesses.

16:13And I think maybe the most important thing is my parents weren't around, so it meant that there was this shame and then this big void of independence. And you have to do something with that as a kid. You have to run an experiment. You have to alleviate your own shame. So that's when I started selling things and selling things in the house and selling a few things that belonged to my mom. And then that's, you know, I could buy things and that alleviated the shame. So that did two things. It taught me that there's actually not a lot between any idea you have and the realization of that idea, which is like a really unbelievable lesson to learn at 14.

16:47That you can like have an idea that you want to get on the ski trip with your rich white friends. and it costs 700 pounds and you don't have one pound for lunch, let alone 700 pounds. And you can find out a way to get the 700 pounds. It's like a really unbelievable thing to learn at a young age. And I think that's the most important thing is that I think I have a bias towards believing things are possible. And then through time, if you want to know like why I am the way I am now in terms of analytical, I've just learned that whenever I find a principle

17:21to really hold on to it. And what I mean by principle is like, when something holds to be true over time, and in multiple contexts, I get really like attached to that. I actually was speaking to Ray Dalio this morning, he was on the show this morning, and he's the guy that wrote the book on principles. And he says the same thing. He went from being broke to the world's biggest hedge fund, I think he's worth 15 billion. And he says the same thing. He says life is about identifying principles, going through your day, reflecting on what happened, and then writing down the truths that appear to be true, getting as close.

17:56And he actually, funnily enough, I didn't even realize this, but he said to me, the other thing is you reflect and you need to get as close as you possibly can to reality. And what he's saying there is what I said earlier about not being romantic. He goes, you have to be, and think about this guy. He bought the world's biggest hedge fund and is worth$15 billion. The hedge fund I think is worth hundreds of billions, Bridgewater, he says you have to reflect and then get closer to reality. And you have to realize that you're like highly, I'm like highly emotional, highly biased, highly insecure. We all are.

18:26And that's going to get in the way of your potential. So one of the great things that I did at 21, 22 years old is every single day at 8 p.m. I said to myself that I was going to write a tweet and post it. Now, I thought I was doing that to build a following and it built a following, which is great, which then gave me a platform to launch the diary of a CEO. but the more profound thing it did is it meant that I went through days like today and then at the end of the day I had to condense everything I'd learned or one the most important thing I'd learned into 140 characters and if you've listened to Richard Fryman the physicist he says that to truly understand something you have to be able to condense it so much so that you could and simplify it so much so that you could teach it to a 14 year old and that's what I was accidentally doing at 22 years old.

19:10So I wish you could, I wish you could meet me at 18 years old. Because like, like terrible ideas, clueless, university dropout, parents aren't speaking to him, shoplifting food to feed himself. If you'd asked me anything about marketing or anything, terrible ideas. My friends who were there take the piss out of me. They remind me of these terrible ideas I had. But that process of self-reflection on a frequent basis, and especially if you publish it, which means you get feedback, which helps to refine the idea again, is I think the most underrated self-development idea that nobody seems to talk about.

19:46Every single day, write in your diary, condense it, summarize what you've learned. And then it means when people ask you questions on stage, you have really concise ideas that you can swing to. So one thing I'm hearing from that also from who you were growing up is a bit of something that I carry, which is a scarcity mindset. Do you feel that? So that drives me quite a bit. I think it drives a lot of creators. And I think it's why the game, especially of the analytical form of content creation, fills you up because you can get an abundance or a relative abundance of something. Views, validation, money, comments, engagement, you can get a relative abundance.

20:26So I'm curious because one of the headlines we all read about you this year is you turned down$100 million. So when you come from that level of scarcity, and you get approached with building a show at the scale of your show, and then someone comes and goes, I'll give you$100 million, Stephen. And you go, no, I'm good. What's the principle driving that when what I'm hearing is a kid who grew up with a bit of scarcity? yeah so there's there's several layers of context here so i'm going to try and knock them all off so in terms of like the offer that we received uh i think we can beat it on our own and without putting 12 ads into the podcast so we can beat it by putting two ads into the podcast with our own in-house commercial team fortunately i come from a background where i was running businesses for the last 15 years so i know how to build a team run a commercial team my last business was in brand deals.

21:25That's the company that emerged out of those Facebook groups that I talked to you about, became Social Chain, which did marketing and brand deals with the world's biggest brands. I lived in New York for three years, and our clients here were Uber, Coca-Cola across Europe, et cetera, et cetera. So I have that experience. I didn't need a media conglomerate to tell me how to build a team that can do that in-house. So that's the first point. And that's proven to be true already. When someone offers you these big numbers, you don't get paid the money in your bank account. It's paid over, in our case, three years.

21:56So you can kind of do the numbers on that. And so my question is, do I think in the next three years, will I make more than said figure if we do this in-house? And will this mean less ad load, which is potentially going to create a better customer experience for the audience, which is going to mean the show grows more and that's going to compound? So that's like one bucket of thought. The other is wanting to be a master of my own destiny in terms of making decisions, which is maybe the most important, the most important, no, the second most important thing. And these partners have their own incentives and they move at their own speed.

22:30No one's going to let me have a fucking failure in an experimentation team in the old world. Because I have to explain myself to people. So the old world is set up in a certain way. And sometimes it can be a gravitational force. And the last point is, I just love it. And when I think about the trade, the happiness trade of X million, whatever, to lose any part of what I love, it's just not worth it. Like, you know, I have a certain level of privilege because my last business did well and the show does well. Where I do ask myself a lot these days, any figure, any number that someone offers me, like, how is it going to move the needle on my happiness, if at all?

23:14and it's like very very hard to find find something that will move the needle on my happiness realistically nothing will do you know what i mean nothing's gonna make you if i if i get like well i have a question for you because maybe colin would ask me this question but we talk about this quite a bit would more time and space make you more happy or no meaning because you're a very busy guy yeah like the fact that you came here we're really grateful but i was like you're recording all day and you're still gonna come and do this and i assume you're gonna go do more stuff so like when you think about your life as a creator right now yeah and as an entrepreneur when you think about the trades that you have to make like you're talking about happiness there like do you feel like that trade right now is at a healthy balance or do you look at it you go you know what if i could buy a little more time and space to have some peace i'll take it so what i what i if you gave me two more hours in the day and i couldn't spend them doing what i currently do now because I might accidentally um I would spend them with my girlfriend and my friends that's like the thing that I think would expand my happiness more and actually it was my birthday last week so I flew all of my best friends over the last 10 years to my house in LA and we had a week where I wasn't in work I didn't do any I didn't do any work well not really um and it's like the most amazing week of the year just to spend time with my best friends who've been there for me for the last 15 years and to just do fuck all and just chill out and just to catch up and talk to each other.

24:39I know this to be true. And all of the billionaires, including Ray Dalio that I interviewed this morning and the billionaire that I interviewed yesterday, they all say the same thing. At the end of the day, and it's super cliche, but it's true. At the end of the day, it comes down to relationships. It all comes down to relationships. And if you're, if you ever get like wildly successful and you buy a big house, the first thing you think when you walk in it is who like that's the question who with because I've had that feeling of walking into a new big house and thinking okay this means nothing unless it's full of other people that I love and so it's a balancing act of yeah I've seen so many people and from podcasting I've seen so many people that burn all the bridges before they get there um I think I've done a fairly good job of not doing that I have my same group of six best friends.

25:29I've been with my girlfriend now for seven years. Probably should put a ring on it. I know I'm working on that. But I've said before the end of this year. And here she is. Our last surprise guest. But yeah, that's the most important thing, yeah. How do you, I feel like a problem that we have is actually protecting our time. Because we went through five, six years of what felt like a lack of opportunity coming our way. And then when we gained some traction, opportunities came our way, and it was, of course, you say yes. You say yes, you say yes, you say yes. And I don't think we've been able to get out of that mindset, really.

26:08You know, I mean, like, even for us this year, like, Samir and I were talking, our homes burned down in January, and we both had our first kids. And a couple of weeks later, we were like, yeah, let's do this. I think we could do it. This is the year. and I don't even know if we have the tools yet. I think we're learning them. But how do you have the tools and the frameworks to say no when you, and I'm not saying we should have said no to this, but I'm saying like, how do you look at opportunities? Because you obviously have them coming. How do you know yes or no? I think maybe this goes back to what I was saying about being really principled because that's the great thing about principles.