Steven Bartlett’s story isn’t the conventional rags-to-riches tale. There was no grand vision, no five-year plan. As a university dropout, bouncing from one borrowed mattress to another across Manchester, he wasn’t dreaming of billion-dollar valuations. He just wanted freedom.

“I had the same doubts as everyone else,” Bartlett tells The CEO Magazine. “And I was convinced I had failed before I’d even begun.

“My only ambition at that stage was to create something that gave me freedom from a system I didn’t fit into, freedom to work on ideas that excited me. I had no grand vision for what that would look like – I just knew I wasn’t willing to live a life dictated by someone else’s plan.”

A life on his terms

The instinct to follow what excited him treated him well. Today, 32-year-old Bartlett is more than just an entrepreneur. As the host of The Diary of a CEO, one of the world’s biggest podcasts, he’s become a leading voice in modern leadership, startup culture and personal growth.

And while his journey has been anything but conventional, there were moments along the way that confirmed he was on the right path.

“The time I realized we were onto something was when I got that first £5,000 [US$6,458] investment to start my first company,” he reveals.

“I knew there was an opportunity to build something around social media and marketing. When we started to build an engaged community and brands started chasing us instead of the other way around, I knew it was going to be big.”

‘Big’ was an understatement. The company grew to become one of Europe’s most influential marketing agencies, working with brands like Spotify, Microsoft, Comedy Central, 20th Century Fox, P&G and Puma, just to name a few. And it wasn’t long before investors took notice, fueling the company’s rapid international growth.

But Bartlett knew it was just the beginning.

“I remember when we landed our first six-figure deal, it validated the idea that social media wasn’t just marketing – it was culture-shaping,” he says. “That’s when I knew this was bigger than just another agency.”

From entrepreneur to investor

Bartlett’s influence extends far beyond his first company. In 2021, he co-founded thirdweb, a software platform backed by Shopify and Coinbase that simplifies building Web3 applications. And just recently, in 2025, he founded FlightStory, a media company and investment fund, designed to inspire a happier, healthier humanity.

As an investor, he’s also backed some of the most disruptive startups in health, wellness and technology, including Huel, the United Kingdom’s fastest-growing ecommerce company internationally; ZOE, a personalized nutrition program developed by leading scientists; and WHOOP, a wearable technology brand transforming fitness tracking.

With his sharp eye for innovation, Bartlett was a natural choice for Dragons’ Den, where he became the youngest-ever Dragon at just 28 years old. His time on the TV show reinforced what he had seen throughout his own journey – many founders are great at building products, but they struggle to build sustainable businesses.

“They get obsessed with their idea but ignore the fundamentals – hiring the right people, understanding distribution and creating a business model that actually works,” he explains. “A great product without a great business is a hobby, not a company.”

His advice to entrepreneurs? Clarity beats hustle.

“So many young entrepreneurs chase growth without knowing where they’re going,” he says. “Direction and urgency are the difference between success and failure.

“Work on things that matter, build with intention and don’t let external pressure dictate your timeline. And most importantly, start. The best entrepreneurs are doing, experimenting and learning much faster than those failing to start.”

What separates the great leaders

Bartlett has spent enough time around business leaders to recognize what separates the good from the great. And when it comes down to it, he believes self-awareness is the defining factor.

“A lot of leaders think leadership is about having all the answers. It’s not,” he says.

“It’s about knowing your blind spots and surrounding yourself with people who fill those gaps. The best leaders don’t pretend to be the smartest in the room; instead, they create rooms where the smartest people want to be.”

Another defining trait? Transparency.

“People mistake transparency for weakness, but real transparency is a strength multiplier,” he explains. “It builds trust, and trust builds influence. Effective leadership requires clear communication of rationale, even when delivering difficult messages.”

However, Bartlett cautions that transparency should always be constructive.

“I tell my team the truth, but I also recognize my job is to steer the ship, not burden them with every storm,” he says. “The balance comes from communicating vulnerability in a way that reassures rather than destabilizes.”

The power of a personal brand

Bartlett hasn’t just observed how social media has reshaped leadership – he helped lead the transformation. And he warns today’s leaders must adapt or risk irrelevance.

“A CEO today has to be a communicator,” he says. “Social media has stripped away the corporate walls. People want to hear directly from the leader, unfiltered.

“If you’re a CEO and you’re not engaging in social media, you’re invisible. It’s not about being everywhere; it’s about being present in a way that feels human and authentic.”

That’s where personal branding comes in, he says.

“It’s your digital reputation. People connect with stories, not slogans,” he points out.

‘“If you want to build a personal brand, show up, share value and be relentlessly yourself. If you don’t tell your story, someone else will – and they might not get it right.”

Rethinking success

That belief has fueled Bartlett’s own rise. Through The Diary of a CEO, he’s created a space where conversations about business and success go deeper than strategy – they’re raw, honest and often deeply personal. And he admits that he often walks away with new insights himself.

One of his most profound takeaways on success came from Mo Gawdat, a guest on his podcast and someone he also considers a close friend.

“Mo is someone I hugely look up to, and he said something that completely reshaped my view on happiness and success: ‘Happiness is equal to or greater than the events of your life, minus your expectations of how life should be.’

“That hit me,” Bartlett says. “We’re conditioned to believe happiness is on the other side of success, but if our expectations are constantly escalating, we’ll never feel it. Success isn’t about more – it’s about alignment between what you do and what truly fulfills you.”

The next chapter

Despite all he’s accomplished, Bartlett, like many high-achieving entrepreneurs, insists he’s just getting started.

“The next chapter is about scaling impact,” he says. “I want to invest in more companies that align with my values, push The Diary of a CEO as well as all other podcasts produced by FlightStory into new spaces and continue to challenge the way we think about business, leadership and success.”

But more than that, he wants to leave a lasting legacy.

“I hope I’ve helped redefine what leadership looks like – that I’ve shown people that you can lead with authenticity, that success doesn’t have to come at the cost of wellbeing and that the best businesses are built on purpose, not just profit,” he says.

And for those still doubting themselves, Bartlett has one final piece of advice: “Whatever you’re building – your career, your company, your life – just remember: the world is shaped by people no smarter than you. The only difference is they had the courage to start.”