Interviewing Steven Bartlett - the CEO behind the diary

Holly Branson and Steven Bartlett - The Diary of a CEO host and member of Dragons Den
Kami White / Virgin Management
Holly Branson
Holly Branson's writing
Published on 4 December 2024

Maybe the most powerful force in the world is just believing that something is possible.

It was such a joy to sit down with Steven Bartlett in a room full of Virgin colleagues and some incredible Virgin Start-up founders for my latest Meet the Author interview. I’ve been listening to Steven’s podcast for a few years and I constantly distracted my team by sending them extracts from his brilliant book! So when I got the chance to learn more about the CEO behind the diary, I jumped at it. 

Holly Branson - 2024 - Steven Bartlett - Dragons Den member and host of The Diary of a CEO podcast
Harry Kinnaird / Virgin Management

From immigrating to the UK at two-years-old, to growing up in an entrepreneurial family where money came and went, and with siblings who were intensely academic – Steven’s early years formed who he is today. He also told us how he ran different events and entrepreneurial initiatives all throughout his time at school. Indeed, he ended up being expelled and then invited back because he made the school so much money. When it came time to go to university, he left after one lecture to start his first business. An entrepreneur, through and through! 

His brilliant (and best-selling) book called The Diary of a CEO: The 33 Laws of Business and Life captures the deeply relevant lessons he’s learnt himself and via the guests of his podcast so eloquently and succinctly. Our interview was much the same, and I hope you all enjoy it. 

Holly Branson interviews Steven Bartlett - the CEO behind the diaries

I love how dedicated Steven is to experimentation and failure. As he said to us: “When you run experiments, what you build is evidence. This is what a lot of kids are robbed of.” In our education system, young people are not given the opportunity to have an idea and execute it from beginning to end. As a result, they are robbed of all the lessons, the skills, and the self-belief that they need to succeed in both the future, and in our current world of work.  

In such a fast-paced world, experimenting and failing is the best way to stay ahead. As Steven said: “You have to increase your rate of experimentation.” By experimenting more, you’re likely to fail more, and “failure is feedback, feedback is knowledge, and knowledge is power.” I couldn’t agree more. 

Holly Branson and Steven Bartlett
Harry Kinnaird / Virgin Management

I was also surprised to hear about the early days of Steven’s podcast - The Diary of a CEO. It’s difficult to imagine now, but Steven had almost no listeners for the first few years. A lot of people see success stories blasted across social media, but we forget about the years of hard work (and sometimes embarrassment) that it takes to get there. It’s a reminder that you’ve got to “put in the hard graft.” And if anyone is feeling disheartened by the grind, it’s comforting to know that people like Steven and my dad have been there too. If you’re working on something you truly believe in, it’ll be worth it in the end.  

Thank you, Steven, for taking us through your fascinating career journey. From building and acquiring companies, to constantly evolving, experimenting, testing, and making bold changes when things didn’t sit right with you – it’s an entrepreneurial story for the history books.