‘Insecurity was my biggest motivator’: how Dragons’ Den’s Steven Bartlett became a ‘happy sexy millionaire’

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I am sitting in what Steven Bartlett’s team semi-seriously refers to as the Matt Hancock chair. It is upholstered in the same plush fabric that swathes much of the millionaire marketing mogul, social media entrepreneur and podcaster’s penthouse flat in London. Above me is a crystal rainfall chandelier; in the corner of the room, Bartlett’s French bulldog, Pablo, snores under a painting of the Irish mixed martial artist Conor McGregor, emblazoned with the legend: “My success isn’t a result of arrogance – it’s a result of self-belief.”

It was in this chair that Hancock gave his first, stomach-churning interview since the restriction-breaking extramarital affair that led to his resignation as health secretary in June 2021. It was a scoop for which veteran lobby journalists would have chewed off Bartlett’s arm – Hancock insisted the relationship was never about “casual sex” and said he broke the Covid rules because he fell in love – and yet Bartlett is not excited by the prospect of interviewing more politicians. “They’ve asked and I’ve said no,” he says airily.

Why are politicians lining up at the door of a 29-year-old independent podcaster? Because Bartlett’s The Diary of a CEO regularly tops the UK charts, pulling in 6.6m streams a month and more than £1m a year in advertising. Despite this – and Bartlett’s roster of high-profile guests, including Molly-Mae Hague, Craig David, Liam Payne and Piers Morgan – he says: “I don’t think of myself as an interviewer or a podcast host.”

I had expected Bartlett to be all throbbing ego. He is, after all, the man who dropped out of university at 18 and later founded Social Chain, a social media marketing agency that was valued at €186m (£160m) in a public listing in 2019, making Bartlett a multimillionaire at 27. After leaving Social Chain in 2020, Bartlett became the youngest dragon on the BBC investment show Dragons’ Den. He has 2.2 million followers on social media, a ripped musculature that he displays proudly online and a habit of posting motivational quotes on his Instagram page (sample: “To embrace tomorrow you must let go of yesterday”). In his bestselling 2021 memoir, Happy Sexy Millionaire, Bartlett boasted: “I’m currently in the best shape of my life … have millions of followers, millions of $$$ in the bank … [and was] able to build a global business at 21 years old.”

View image in fullscreenWorking it … speaking at a startup conference in Newcastle in 2019. Photograph: Thomas Jackson/Alamy

But in person, Bartlett is likable and polite, apologising four times for keeping me waiting as he finished a call and seemingly as keen to hear my views as he is to share his own. His hand is grotesquely swollen, but he is waiting until our interview is over to seek medical attention. “I hurt it lifting [the comedian] Lee Mack at Soccer Aid last night,” Bartlett says, sighing. (Bartlett is a huge football fan – in his free time, he uses the app Footy Addicts to find kickabouts in local parks, turning up unannounced, to the bemusement of his fellow players. “They say: ‘Aren’t you that kid from Dragons’ Den? I listen to your podcast!’”)

He was born in Botswana to a black Nigerian mother and a white British father and raised in an all-white neighbourhood in Plymouth. His parents’ relationship was dysfunctional: he says that his mother once chased his father through the house with a kitchen knife and screamed at her husband constantly (his parents are still together). Does his candour get him into trouble? “I made a decision at some point in my life that I was going to be honest with all this stuff,” he says. “I think I have a good relationship with my parents.”

Bartlett’s mother was a serial entrepreneur – “the hardest working person I know” – but her businesses failed. Money was tight and Bartlett was often ashamed that he didn’t have the same gadgets or clothes as his middle-class peers. School was a struggle. “My brothers were really smart and studious and I was falling asleep in class all the time,” he says. He was one of the only people of colour in his school and straightened his hair to fit in. “A lot of people ask me: ‘Why are you so motivated?’” he says. “The answer to that is based on a lot of underlying context about shame. Insecurity was my biggest motivator when I was younger.”

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Do I think hard work matters? Yes. Do I think hard work at the expense of your health and wellbeing is a good idea? No

After school, he dropped out of Manchester Metropolitan University and co-founded Wallpark, an advertising platform, but struggled to bring traffic to the site. “We had run out of money and I saw this Facebook page called ‘Things Manchester Students Don’t Say’,” he says. “At the time, brands wouldn’t go near social media. I remember being curious about what would happen if I posted my website there.” His instincts were spot on. “We could market something on social media and it would do phenomenally better than all the other channels,” he says.

Bartlett then picked up social media marketing work after cold-emailing what he describes as “awful, low-tier clients”. After working as a consultant, a client suggested he start a company, which became Social Chain. He launched The Diary of a CEO in 2017, while he was a jetsetting executive, and the early episodes have a late-night, confessional air about them. Bartlett, speaking without notes in the early hours, talks about the stress of being responsible for hundreds of people, many of them decades older than him.

What becomes apparent from speaking to Bartlett is that, despite his personal brand being connected to his identity as an incredibly successful young CEO, he didn’t really enjoy running a business. “When I left Social Chain, I said to my girlfriend: I’m never going to be a CEO again, ever,” he says. Managing a large company was “brutal, but I don’t think I allowed myself to admit it”.

He resigned from Social Chain in 2020 after a disagreement with the board about the direction of the company. “One of the things that I’m good at, and I enjoy, is the top level strategy of where we are going, the vision,” he says. “And I could no longer make those decisions, because I didn’t own enough of the company.” He initially wrote a strongly worded resignation email, but deleted it and wrote one instead from a “place of gratitude … these people had basically changed my entire life and believed in me.”

View image in fullscreenOn the ball … tussling with Mo Farah at Soccer Aid this month. Photograph: Alex Davidson/Getty Images

The day he handed in his notice, Bartlett cried, but he was relieved. “I just felt really free,” he says. “You can feel free and lost at the same time. Because your purpose and identity has been wrapped up in this thing.” He has subsequently co-founded two more companies – Flight Story, which builds retail investor strategies, and Thirdweb, which helps developers without coding knowledge build blockchain-related apps – but he is not involved in the day-to-day management, preferring to consult on strategy, fundraising and growth.

Despite his complicated feelings about the business that made him wealthy, Bartlett has become a guru for a generation of young, individualistic, financially motivated aspiring entrepreneurs. Earlier this year, they packed out theatres for the bombastic live version of Bartlett’s podcast. Bartlett, a musical theatre nut, recounted his life story from a spotlit stool, accompanied by a gospel choir directed by a former Hamilton producer. (He has seen the Lin-Manuel Miranda show eight times.) The Telegraph described it as “the most bonkers night I have seen in the theatre”. Predictably, it was a sellout. “I had the time of my life,” says Bartlett, misty-eyed.

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If Bartlett has a message, it is this: individuals should take responsibility for their actions, work towards long-term goals and believe in themselves; be realistic about their talents, but remember that few situations can’t be ameliorated through sheer effort. It is not a new message, echoing self-help tomes from Max Weber’s 1905 tract The Protestant Ethic and the Spirit of Capitalism to Napoleon Hill’s 1937 personal development manual Think and Grow Rich. But Bartlett’s genius has been to update the message via pithy social media graphics and search-engine-optimised YouTube videos for the eroded attention span of a 21st-century audience.

Without a sense of purpose, humans aren’t typically very happy

If, at times, Bartlett’s message is contradictory – he urges people to believe that they “are enough”, but also to identify and work on their weaknesses – his message of incessant self-improvement falls on receptive ears. His young fans aspire to “financial freedom” – the trending euphemism in startup circles for getting rich – and having a strong personal brand, like their hero. They view professional careers, acquired after years of study, as relics of the past; being a serial entrepreneur is the goal. Bartlett views university as a money-wasting racket, but he acknowledges: “Had I been smart enough to be a doctor, I think my views of the education system would be different.”

Fans listen to The Diary of a CEO to glean business advice from influencers such as Hague, a former Love Island contestant who told Bartlett in January that “we all have the same 24 hours in a day”, prompting a social media firestorm. The backlash surprised Bartlett, because the broader sentiment she articulated – which distils 21st-century hustle culture – has been uttered repeatedly by guests on his podcast and, to some extent, by Bartlett. But he also questions this idea. “It’s nuanced,” he says. “Do I think hard work matters? Yes. Do I think hard work at the expense of your own health and wellbeing is a good idea? No. Do I think you should just endlessly hustle, hustle, hustle to become a successful entrepreneur? No.”

He tells me that he is striving for “balance” in his life and is not materialistic; as proof, he shows me his rusting ear studs. “Five pounds from Topman.” His ultimate aim is to “do my own potential justice”. But isn’t all this unending personal development just exhausting? Why can’t we just be our mediocre, unevolved selves? “From what I’ve seen, without a sense of purpose, humans aren’t typically very happy,” he says. I tell him that I don’t set personal goals. He is flabbergasted. Surely I must have some, he begs. Reluctantly, I concede that I would like to buy a house at some point. He laughs, exultant.

View image in fullscreenHot seat … Bartlett on Dragons’ Den. Photograph: BBC

Bartlett’s critics claim that, for all his grandiose self-mythologising, he is vague on the details of how exactly he became successful, preferring to hide behind unoriginal aphorisms. In an excoriating New Statesman article in March, Bartlett was described as “more of a bluffer than a prodigy”. The article concluded that Bartlett “got lucky” by founding Social Chain at a time when social media marketing was taking off and that the business advice offered in Happy Sexy Millionaire is generic and unhelpful. A thin smile twitches across Bartlett’s lips when I ask him about the write-up, which he read. “I’m sure there was a lot of luck involved in my journey,” he responds.

He insists Happy Sexy Millionaire was not intended as a business manual. “In different forums, I can give business advice,” he says. “If I’m in the boardroom talking about how to scale, or technical aspects of how to raise a round, or how to honour investors, I can do that … Do I talk about that on my social media channels or in my podcasts in detail? No.”

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I suggest that his fans might welcome specifics about how he landed big clients at Social Chain and then serviced their accounts. “I can go and get you my laptop and show you those pieces of work,” Bartlett offers, suddenly animated. “They are 200-page insight pieces into customer engagement, customer demographics, where customers are, how they behave.”

Despite the criticism, Bartlett clearly knows what he is talking about in relation to business. His observations in Dragons’ Den are astute; his interviews on The Diary of a CEO, with executives in particular, are frequently superb.

He is less sure-footed with regard to challenging controversial guests. In his interview with Hague, who had recently been announced as the creative director of the fast-fashion brand Pretty Little Thing, he failed to ask her about accusations of illegally low wages being paid in the supply chain of Pretty Little Thing’s parent company, Boohoo. “I didn’t know whether she was the person to talk on that topic,” he says.

I suspect that the broader issue is one that plagues the industry in general. A blockbuster podcast needs high-profile guests, but they may not be willing to submit themselves to a grilling. This may matter less when Bartlett is interviewing business executives or pop stars, but it does matter when he is confronted with a media-trained politician, such as Hancock, or a professional contrarian, such as Morgan.

In their discussion, Bartlett asked the former health secretary: “One of the decisions that was made, and ultimately criticised, was this whole care home stuff – what’s your view on that?” Hancock launched into a defence of his policy of discharging untested Covid patients into care homes, later ruled unlawful, that a more robust interviewer would have dismantled in minutes. Does Bartlett think he pushed Hancock hard enough? “Honestly, I did my best,” he says. “I don’t consider myself to be a journalist.”

His decisions to book Morgan, as well as the author Jordan Peterson, whose work is beloved by men’s rights activists, have proved contentious. “I don’t ever want to get to a situation where we don’t have conversations with those who we disagree with,” he says. “Because I think much of our progress as a people has come from breaking our echo chambers and having difficult, uncomfortable conversations and being willing to listen.”

But these conversations were not particularly difficult or uncomfortable. He thanked Peterson for changing his life and allowed Morgan to go on a largely uninterrupted rant about cancel culture, defend his bullying of the Duchess of Sussex and falsely position himself as a trans ally. Does he accept that, by booking such guests, he sanitises their views for a wider audience? “I don’t know if it’s sanitising their views,” he says. “You can have a conversation with me and not agree with everything I live by and stand for.”

Bartlett is still finding his feet as an interviewer, despite the runaway success of The Diary of a CEO. “I have moments where, afterwards, I say: ‘I wish I had challenged that person more,’” he says. As we are wrapping up, he asks me for feedback on what he should be doing better. I suggest he could go harder on people. Ever the self-optimiser, Bartlett appears to consider my proposition. Perhaps he is a Paxman in the making.

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