Long before Steven Bartlett knew what the word “entrepreneur” meant, he was already brainstorming ways to turn an idea into reality.

Once he realized “university was not gonna work” for him at the age of 18, he had to figure out how “to have nice things and have a nice life” while also enjoying what he does. That’s when he took what he learned from his mother growing up about executing your ideas and built a media and investment empire, which includes multiple ventures and his top-charting podcast, The Diary of a CEO, that’s featured guests like Michelle Obama, Scooter Braun, Simon Cowell and Richard Branson, among many others.

Now, at 32 years old, he’s sharing the experience and knowledge he’s gained over the years with the world in hopes of inspiring others on their journey to success and happiness. “When people think about becoming an entrepreneur or taking a risk, I often think that they’ve got the risk equation horribly wrong,” he tells The Hollywood Reporter. “So if you have the North star, which we should all have, that I want to be happy, then anything that jeopardizes your chance of happiness is the risk.”

Below, Bartlett opens up about how Diary of a CEO came to be, how he gets his guests to be vulnerable, his dream guests he has yet to book, what he loves most about being an investor on Dragons’ Den and more.

Knowing the risk that comes with starting businesses, did you have any fears following this career path?

It’s interesting because when you say risk, for me, risk was staying in university and then getting a job as a consequence of that decision that I hated, and then living a life that I hated. To me, the cowardly thing to do was to drop out and to try and design a life that I liked. Because when people think about becoming an entrepreneur or taking a risk, I often think that they’ve got the risk equation horribly wrong, and if you have the right North star, you can figure out what the risk is in your life. So if you have the North star, which we should all have, that I want to be happy, then anything that jeopardizes your chance of happiness is the risk. And university jeopardized my chance of happiness, so university was the risk. 

Having built one of the most popular podcasts, The Diary of a CEO, what made you want to launch a podcast focused on giving CEOs and leaders a platform to tell their stories and share advice?

Over a long period of time, if you follow what you love doing the most, there’s the greatest chance of mastery, and then there’s the greatest chance of creating the most value in the world. And actually me starting podcasting was very much the same. At the time I was making these videos on Facebook Watch, like a two-minute fluffy cliche video about any subject. So it was romance or it was relationships or it was business or it was motivation or discipline. And I didn’t enjoy it. The views were massive, but I didn’t really believe, even though it had a big view number, that it was having a good impact on the world.

Then I discovered this thing called podcasting in 2017, and I went home, I had a chat with my team. I said if I was gonna do a podcast, then what I would try and do is create something that catered to the thing right now in society that is in least supply, but greatest demand, which is the 99 percent of your life. Like on social media in 2017, I can see you on the beach in Hawaii drinking the cocktail. Like it was very, very polished back then. Then we were at the start of what I call the authenticity wave where people started to show things less polished. The 99 percent of my life is like eating the pot noodle in bed at 2 a.m. with one eye open, looking at the screen, worrying about the thing that’s happening in the next day, that text message I’ve got and that email that I’ve got, mental health battles, relationship troubles, family issues, intimacy, sex problems, all of these things, regrets, fucking up in work. I think that’s the 99 percent of our lives. And so the Diary of a CEO in its very name is what you’d find in a personal, private diary of an important person. And there’s almost a juxtaposition there because it’s people in higher positions that we’d most like to look into their diaries and really know what they were thinking. So that’s what I did. 

How do you go about getting your guests to open up and be vulnerable? 

One of the really important things is you do forget the cameras are there and you forget the cameras are there because the way we’ve designed this set. Although there are nine cameras, you can’t see the cameras and also you can’t see anybody else. So what it feels like, especially ‘cause you walk into a space and there’s a carpet under your feet and I’ve got my shoes off, it feels like you’re at home, and you’re at home with just me. Nobody else is there. Your team are a million miles away in another room watching on a screen, and then we talk for three to four hours. So really what you’re focused on is our conversation and me. And then there’s lots of small subtleties like making sure that our body language, [that] we’re straight on, making sure our eyeline is aligned, making sure the CO2 levels in the room are below 1,000 parts per million because if you want to have a good sort of conversation, you don’t want CO2 levels to get too high, so we think a lot about that. Temperature’s a big one, the music when you arrive into the studio is a big one, tailoring it to what we know about you and songs that make you feel comfortable and that take you back to your childhood. And then the other great thing that the format of a long form podcast allows is me to like shut the fuck up and listen. And it’s remarkable what happens when you shut the fuck up and let someone speak. 

How do you decide who you want to book as a guest on your podcast, and do you have a dream guest?

The framework that I use to decide who comes on the show is basically these three overlapping circles in my head, which is what am I really interested and curious about. And that’s critical because if I’m gonna do this for the next 50 years, I have to wake up every day, look at my calendar, see the name of the guests that I’m speaking to for five hours today and researching for three hours, and go, I can’t wait to go to work. And do I believe that my audience will be genuinely interested in this and curious about it? Then the last thing is actually, do I believe that the platforms will show it to my audience? Because there is an algorithm that we now contend with. And on that platform piece, there are certain things that the platforms wouldn’t show to my audience for a variety of different reasons. I wanted to have a conversation about assisted dying, for example, ’cause I got really interested in that ‘cause of some things that happened with my friends and I’m well aware that actually YouTube censors that subject. 

And you asked your last question, which was one of my dream guests that haven’t come on yet. I’m keen to speak to Barack Obama. I emailed his team this week. I’m waiting to hear back. That’d be good. I spoke to Michelle Obama, which was great, so Barack would be great. And then people don’t like when I say this one, but I’m gonna say it anyway: I’d like to interview Elon Musk to ask him if he’s happy, and I really wanna find out. And if he’s not happy, I wanna understand why he made that trade, ‘cause I’ve heard him talk about how it’s painful inside his head, and so I’m curious as to why he’s not doing anything to stop that. 

In addition to podcasting and your multiple business ventures, what made you want put your words on paper with your best-selling books, Happy Sexy Millionare and The Diary of a CEO: The 33 Laws for Business & Life.

I absolutely did not want to write books. I thought it was a waste of time, painful, pointless. Like why would you want to write a book when you can post on LinkedIn and get the same amount of views on LinkedIn? Why would any logical person go to Indonesia alone in a hut by a lake and write a book when it’s like super painful and it costs so much time. And this goes back to what we were saying earlier about like depth and impact. It goes back to what I was saying about, I used to make Facebook videos that got tens of millions of views but had like no impact. Then I started this podcast that got 100 downloads and it had a much greater impact, and this is almost the same analogy with the book. Of course I can do an Instagram Story and 1.4 million people will see it, but getting 10,000 people to read a book that you’ve written seems to yield more impact, and that’s exactly what I found. I just couldn’t believe that, and even with the last book, when it surpassed a million copies, it had more impact in my view, globally, than getting a billion views on my LinkedIn the year before.  

You’re involved with so much, so I also wanted to ask what’s been your favorite part about being an investor on the BBB reality series, Dragons’ Den?

I have roughly 100 entrepreneurs a year pitch to me their businesses, and it’s just the most wonderful reminder of the power of entrepreneurship to change the world. If you look at what I’m doing now with Flight Story, there’s really two things — there’s our studio, which is media, and then the other side of it is our fund, which is an investor. And I think that these two things together are the most powerful vehicle to change the world. I think media positively, negatively influences people’s lives, it influences the electorate, and that drives what we do at the polls, and then that drives legislation and changes our world. And I think the same with building businesses. For better or for worse, we shape our future by the businesses that we build. And Dragons’ Den is exactly that. It’s a tremendous honor that was a dream for me as a kid to get to sit on that show, to get to represent a different type of entrepreneur, young Black entrepreneur that didn’t go to university and that started from his bedroom in Manchester, because when I was in that bedroom in Manchester, there was one Black entrepreneur that I could look up to, which was Jamal Edwards at the time, who’s passed away. And the other thing is just this constant reminder of the struggle of entrepreneurs out there. You see how much is riding on it and you get this remarkable privilege of getting to make people’s dreams a reality. 

You’ve previously shared that you’ve turned down offers to partner with streaming giants. Can you expand on your reasoning behind that, given the success other media figures who have taken these mega deals have seen in the space?

I’m an entrepreneur by nature, and being an entrepreneur means you know how to build an organization, you know how to build a business, you understand how to scale a business, you understand the finances of the business, hopefully. And in just over four years, we’ve gone from 0 to we’ll do 52 million views on YouTube this month, I think. We’ll do $40 million in revenue this year, maybe more, maybe less. That’s not including like equity deals in companies. And the growth in revenue has gone up year over year by a three digit percentage number, and that’s all been in-house. So if I play that forward, and it’s like going really well and we’re betting on ourselves, I see no reason to change that. 

Why did you decide to use AI for your new podcast, 100 CEOs with Steven Bartlett, and what are your goals with it?

The Innovator’s Dilemma, my favorite business book, taught me something counterintuitive: the biggest risk isn’t being disrupted by new technology — it’s avoiding it altogether. Companies that ignore emerging innovation don’t protect themselves; they basically assure their obsolescence. That’s why we’re leaning into AI with 100 CEOs. Not because we have all the answers, but because we know the cost of not asking the questions, and FlightStory was built on this idea: stay curious. Experiment, fail, learn and try again. I have no idea if people want to listen to AI podcasts, but I would rather find out this way than the hard way.

If you had to describe what makes Steven Bartlett, Steven Bartlett, what would you say?

Obsession. Being really, really obsessed. Having a bias towards thinking things are possible, even when like objectively there’s no evidence that it is. Urgent, which means operating like I’m running out of time or that there’s a deadline, like put a fake deadline on everything [Laughs]. In love with my partner. I have to include her ’cause she such a foundation to me, she’s like home to me. I wanna be a father as well, so hopefully in the next year or two I can say father. And then like really curious, really open-minded, a dreamer. The last one would be something about the belief that I have so much more to learn. You’d think by doing 400 or 500 podcast interviews that I’d feel smarter; I actually feel more stupid, which was not what I was expecting [Laughs]. I feel like there’s so much that I don’t know.