Jack Sylvester, co-founder of The Diary of a CEO podcast, has quit his role.
Sylvester, who was executive director at FlightStory, described leaving the hit podcast he helped build with Steven Bartlett as ‘one of the hardest decisions of my career’.
He played a pivotal role in helping grow the The Diary of a CEO podcast to nearly 18 million YouTube subscribers.
Writing on LinkedIn, Sylvester said: “Three months ago I made one of the hardest decisions of my career. I walked away from the thing I’d lived and breathed every day for six years.
“It started in a kitchen in Shoreditch. Me, Steven Bartlett and a stupid level of belief that we were onto something the world wanted. I was 24 and knew nothing about podcasting (genuinely nothing).
“I grew up inside that show. It saw every version of me, from the one Googling how to sync audio to video, to the one who learned how to lead a team.
“And I watched it become every version of itself, from a few people huddled around a table to 150 employees and a 25,000-square-foot office.
“We gained over 3 billion views, grew the main channel to 16 million subscribers and our clips channel to 2 million. I even got to shake Michelle Obama’s hand along the way. Instead of hello, my exact words to her were ‘this is mad’.”
Last year, Sylvester was included in Forbes’ 30 Under 30 Media & Marketing list.
He added: “I’m writing this somewhere over the Atlantic, heading home after three months in South America, much of it camping with no signal. No emails, no Slack, no edits, no uploads, no YouTube Studio.
“For the first time in six years there was none of it and no way to even check. I’ll be honest, the start was weird, but I’m glad I had that as it gave me a lot of thinking time.
“We’ve built DOAC to the point where it can function without me, and I realise if you love something, one of the best things you can do is let it go its own way into the world and the most amazing team will take it further than I ever could.
“I owe Steve more than I could ever put into words. Steve, thank you for taking a chance on me all those years ago, thank you for showing me the impossible is possible, thank you for the standards, the advice, the laughs, the encouragement and the trust. It was the ride of a lifetime and I’ll never forget it.
“For now I don’t know what’s next, but I’m more fired up than ever. If you want to connect about podcasting, YouTube or even just want to say hi, drop a comment below and I’ll reach out.”
In an interview with BusinessCloud in 2025, Bartlett revealed how he reached out to Sylvester in 2020 to take Diary of a CEO to the next level.
Bartlett said: “We started off in 2017 but then it was just me, a microphone in the garage at the back of my bedroom.
“Then, in the pandemic in 2020, I called Jack (Sylvester), who was a freelancer, and said: ‘I want to do this podcast and take it seriously now’.
Steven Bartlett ranked third in global list of richest creators
“I took stock of my life and said ‘what would I do now irrespective of remuneration? What did I enjoy?’ The answer I had in the middle of the pandemic was ‘I really enjoyed that podcasting thing that I flirted with in 2017’.
“We started it from my kitchen in Shoreditch, which was the original DOAC set.”
Georgie Holt, CEO of FlightStory and co-founder of FlightStory Studio, told Sylvester on LinkedIn: “Arrived as a kid with a dream. Left as a man on a mission. We love you and are so very proud of you.”