Steven Bartlett Photograph by Will Perez for FlightStory 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. Related Stories General News Kyle Marvin on Love, Lies and Acting Without Pants Business Alex Cooper, Dax Shepard and Other Top Podcasters Reveal Their Proudest On-Air Moments 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. Steven Bartlett, winner of best international podcast for 'The Diary of a CEO,' at the 2025 iHeartPodcast Awards on March 10, 2025, in Austin, Texas. Daniel Boczarski/Getty Images for iHeartRadio 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