Jack Sylvester helped build The Diary of a CEO into one of the world's biggest podcasts. Now he's starting again

Jack Sylvester was 24 when he joined The Diary of a CEO, helping turn what began in a Shoreditch kitchen into one of the world's biggest podcasts. Now a global media business in its own right, the show has amassed more than 3 billion views, 18 million YouTube subscribers, grown to a team of 150, and Sylvester has decided his chapter there is complete.

The co-founder, who announced his departure this month, says the business no longer required the thing he does best: building. Instead, he's turning his attention to new creative formats, with YouTube documentaries now a particular focus.

In an exclusive interview with The Daily Influence, Sylvester reflects on the moment The Diary of a CEO became bigger than expected, the hardest lessons from scaling a podcast into a global media business, and where he believes the creator economy is heading next.

TDI (Hannah Oladele): Let's start at the beginning. Looking back, when did you realise The Diary of a CEO had become much bigger than you expected?

Jack Sylvester: The first time I realised this was going to be massive was when we landed the exclusive Matt Hancock interview during the pandemic. After the Daily Mail piece, every journalist in the country wanted that interview, but we got it. It was the first time I felt we'd gone from a podcast to a place where conversations happen.

I also remember turning to Steven [Bartlett] maybe a year into the podcast and saying we should focus more on America, then reeling off all the things I thought we could do to get us there. He turned to me and said, "Not yet, we need to focus on the UK first."

So we did, and he was right. We grew in the UK, got to number one, and then thought it was time to test our luck in America.

When we landed in America, I went to the Apple Podcasts offices in LA to tell them about us and they weren't really bothered. To them, we were just another podcast trying to grow over there. I came away from that meeting feeling deflated and confused that they couldn't see it. We had to prove ourselves from scratch.

Growing in America wasn't one defining moment. It was lots of little things, lots of gradual wins that grew us bigger and bigger.

TDI: What turned out to be the hardest lesson in scaling the business?

Sylvester: I'm not sure it's a lesson as such, but throughout my time at DOAC, the systems were the hardest thing to nail. How do you make something good and then repeatedly make something good without it breaking the moment a person is removed?

The hardest part was probably letting go of something that had only ever worked because of the way I'd been doing it and watching it break a few times before the systems got nailed down and started working properly.

TDI: Looking back, is there anything you'd do differently if you were starting again today?

Sylvester: I'd have systematised earlier, for sure. For too long I was the person doing everything, even things that I shouldn't really have been doing.

It worked, but it doesn't scale and it doesn't let anyone else grow. If I did it again, I'd build the systems in year one, not year four, and hire for the things I'm precious about far sooner.

TDI: Why did you decide it was the right time to leave?

Sylvester: My superpower is being able to look at an idea and bring it to life in the scrappiest way possible if needed. I'll make an idea happen whatever it takes, even if that means flying to New York on Thanksgiving, when nothing is open, to build a replica set myself out of IKEA furniture, scraps of wallpaper and a makeshift mirror (true story, by the way).

I love creating, building and problem solving, and DOAC didn't need that skillset anymore. I was just maintaining the show, which isn't where I thrive. So I knew it was my time to step away and let the people who do thrive in that environment take it forwards.

TDI: So what's next?

Sylvester: I love formats, so I want to work with creators on new formats that bring people content that’s so deeply human. YouTube documentaries are a passion of mine and something I want to head towards.

TDI: For someone hoping to follow a similar path, what's the one piece of advice you'd give them?

Sylvester: Don't be afraid to not know the answer and don't let that hold you back. The only reason I got to this position is that most of the time I had no idea what I was doing or even whether I'd be able to do the thing. Mostly it's about taking that first step forwards and figuring it out along the way.

A while ago I listened to a documentary on Thomas Edison trying to invent the light bulb and, in an interview at the time, he was asked how it felt to fail. He supposedly said, "I haven't failed, I've just found 10,000 ways that won't work."

So I'd say: try the thing. If it doesn't work, try again.

TDI: What skills or habits matter most for long-term success?

Sylvester: Sort of the same as above: experimenting.

And I think focusing on bringing your audience the most valuable content. Everything else falls into place if you keep experimenting.

TDI: You've spent the past six years watching the creator economy evolve from the inside. What's changed the most?

Sylvester: When I first started, it wasn't as heavily focused on video. Video was a thing, but it wasn't the main focus.

Now it's almost the only thing that matters, plus AI has allowed people to accelerate the rate of making content in a way we wouldn't have seen even a year or two ago.

I'm still deciding if I think it's a good thing or not. I think as long as it's used to make you faster rather than making AI slop, then it's OK. But we'll see where that gets us.

TDI: Finally, where do you see the industry heading over the next few years?

Sylvester: I see a lot more people having a content engine. If you've got a business, you have to be doing content of some kind.

I'm also seeing a shift towards the valuable viewer over pure views. If you're a business and you get 100 views but all 100 are potential customers, that's far more valuable than 100,000 views from people who aren't.

Every business will have to have a content machine behind it. If they don't, they'll get forgotten about quickly.