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The inner workings of The Diary of a CEO

Diary of a CEO on Apple Podcasts


The inner workings of The Diary of a CEO

In Issue #021 of the Pod Bible Magazine, Apple Podcasts spoke to the team behind The Diary of a CEO about the importance of community and goals to expand their business. This is ‘The Creator’, in association with Apple Podcasts.

Apple Podcasts and Pod Bible partnered up for a series of interviews with creators to share their stories and how they use Apple Podcast Subscriptions to connect with their fans. We spoke with the team behind The Diary Of A CEO—Director and Producer Jack Sylvester and Head of Content Grace Andrews—to talk about how subscriptions helped them experiment and discover what resonates with their audience.

Apple: Tell us about The Diary Of A CEO podcast and how it started.

Steven launched The Diary Of A CEO podcast under his duvet just over 2 years ago intending to reveal the more vulnerable side of entrepreneurship—and as a way to record his journey. Three years later, we now have a team of over 10 people producing the UK’s number one podcast. Steven interviews successful people from all walks of life, from CEOs and founders of the world’s biggest businesses to award-winning authors, actors, athletes, and everyone in between. As a platform, we’re dedicated to creating a space for everyone to talk freely without time constraints, editorial oversight, or a hidden agenda. We’re proud to offer a space where guests feel like they can fully open up and share their stories—leaving it up to the audience to form their own opinion. A lot of guests finish the interview and tell us it felt like a therapy session. It’s that level of conversation we’re looking for every single time.

What made you decide to launch a subscription on Apple Podcasts?

We’re always looking at how we can give back to our incredible community. Learning we could offer exclusive episodes, behind the-scenes sneak peeks, and exclusive bonus content for them was the deciding factor for our team.

How do subscriptions fit into your overall business model?

For us, success is a direct result of consistent experimentation. Apple Podcasts Subscriptions is another opportunity to experiment with different content styles — and find what resonates with our audience.

What have you learned after launching Apple Podcasts Subscriptions?

In all honesty, we were surprised at how successful the subscription model has been for The Diary Of A CEO. We have a very engaged audience who are willing to pay for premium content, which has opened our eyes to potential new directions.

Where do you see The Diary Of A CEO in a year?

The goal is to be the number one podcast internationally. We want to be the room where long-form interview happens. We’ve just come back from recording 20 episodes in Los Angeles as part of a new USA series. In a year we would love to come back to the US to record more episodes and make a real dent in the US charts. We’re looking for growth and this seems like a natural progression, as we are currently sitting at number one on the UK charts. In terms of revenue, as the presence of the podcast continues to grow and expand we’ll be looking for bigger and better sponsorship deals that closely align with our values which in turn will allow us to level up our equipment, studio, and overall offering.

Tell us about an episode that you’re most proud of.

There are a few moments that have shifted the growth trajectory of the podcast, such as the episode featuring Steven’s all-time favourite guest, Mo Gowdat. Nearly a year later, we’re still regularly receiving direct messages, comments, and tags from our audience talking about the long-lasting impact that conversation had on them. Other episodes include Jordan Peterson, Molly Mae, Jimmy Carr, Matt Hancock, and Piers Morgan.

What advice would you give someone who is trying to break into the industry?

We asked Steven for his advice on this one and he said, “Don’t try and copy, imitate, or replicate anything that’s already out there. The clearest thing is that category leaders are defined by and win based on their uniqueness, not their similarity. The world doesn’t offer outsized returns for people and brands that serve up ‘more of the same.’ If you want to win, you have to copy less and have the conviction and clarity of vision to lean into whatever it is that makes you, you.

Apple Podcasts Subscriptions is the global marketplace for premium podcast subscriptions. Join the Apple Podcasts subscription community alongside The Diary of a CEO at

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