Diary Of A CEO Founder Rejected A $100M Deal To Build Podcast Empire FlightStory On His Own Terms

Let's go.

I'm Steven Bartlett and we are here at Flight Story HQ in Central London.

I'm an investor, I'm an entrepreneur and I'm the host of the Diary of a CEO podcast.

Two of the most used phrases in our company and still to this day are the phrase 1%, which is an obsession about the tiniest details.

And the second one is the word failure, which is our job is to increase the rate of failure.

I increase the number of experiments that we're doing.

And if you just do those two things, and if you have so much passion as the sort of fuel in the engine, all you need is patience.

And that's what we could see. We could see very early on that we were we were out caring the competition.

On the tiniest little details and we were willing to test more things.

And you you might think like those are words, but if you understood the reality, you would think that I was a psychopath.

Flight Story is a media and investment company that creates host-led podcasts and turns them into entire commercial ecosystems, ranging products, events, book deals, and investment opportunities perfect for each individual host.

At the heart of it all is Steven Bartlett, the host of The Diary of a CEO, which he began in 2017 as a way to get into the heads and the diaries of the world's most compelling people.

It brought in 50 million monthly listeners at the end of 2024, becoming the second biggest host-led show in the world, following only The Joe Rogan Experience.

But Bartlett is in pursuit of that number one spot, and he's creating a data-driven blueprint at Flight Story to get there.

When I started it, I was a CEO, and I asked myself, what would one find in the diary of a person in that position?

One might think it's like P&Ls and scribbles about numbers and stuff like that.

But actually, you'd find a really human story, you'd find someone who's in an interesting role.

In a position, but struggling with all the same things that you're struggling with in your life.

And so in the in the podcast, I endeavor to go a little bit deeper with people.

To understand why it is that they do what they do.

What's really behind the scenes and ultimately, I guess, what would be written in their diary?

If we were lucky enough to be able to see it.

And that was about four years ago.

Steven posted on LinkedIn that he had ambitions of launching what he was calling at the time a network.

Myself and my co-founder and business partner Georgie, we've worked in global podcasting together for many years.

And at that stage, had actually quit our exact roles in New York to launch our own podcast media agency.

But then I like to say that fate intervened.

And we saw Steven's LinkedIn post.

We drafted an email together.

I'm quite a long-term listener of the podcast, so framed it in in language that I felt would hopefully catch his attention.

To our dismay, he replied.

We weren't expecting even anything to happen in response for an email that we had an invite to join him on a meeting.

And even at that point, we weren't expecting to meet him.

And there he was on the other side of the video call, explaining to us all about the network.

And I think in what he was saying, he said something so compelling and profound to me.

He said that he was really haunted by the potential of what he had built with the Diary of a CEO.

And that he could use that methodology and that blueprint to accelerate what he thought were voices that could change the world.

And it wasn't just through gut instinct.

It was through data science that he was seeing these guests light up these exceptional metrics on all of our channels.

That were really speaking to a content genre or a theme or an audience that he felt that by elevating their voices and creating new media around them.

That he could have a really important and I guess compelling impact on these people's lives and the audiences they intended to reach.

We knew that we had to go on this journey.

We knew that this was an opportunity to build something legacy, something generational.

And something that we could really have a profound impact on the world.

And I guess as they say, the rest is history, because we soon pivoted to join Steven.

And myself and Georgie have spent almost the last year and a half signing our first five creators and scaling their media brands for Steven.

Today, Flight Story Studio, the venture's podcast arm, includes five shows.

50% of all revenue from the studio comes from advertising and brand partnerships with companies like LinkedIn and Oracle.

But the other half comes from those additional bits of the ecosystem, including the book deals, events and products.

The Diary of a CEO alone brought in $20 million in 2024 revenue.

And it's on track for $30 million this year.

But building this ecosystem here at Flight Story Studio for our creators.

And you can see the monetization potential across all the various streams.

The first generation of product for podcast creators and influencers was mostly merchandise.

You know, your T-shirts, your hats.

And it was probably leveraging more of the fandom from a branding perspective.

But what certainly what we're seeing at Flight Story is that all of our consumers are now looking for that enablement loop.

So if you think about the Diary of a CEO or We Need to Talk with Paul C. Brunson or Begin Again with Davina McCall, all of the podcast episodes are ultimately trying to help people.

And in fact, all the creators that we sign have to contribute to a happier, healthier, whole human experience.

So then what we're seeing and certainly through all of the the data and analytics and the feedback loop from all of our audiences is that they're looking for products that can help them implement.

The changes that they want to make in their life to help them live a happier, healthier, whole human experience.

That really underpins everything that we choose to invest in.

The host has to really believe in the product or service that they're endorsing.

It's such an intimate relationship with the audience.

And I know I keep saying the enablement loop, but we do think about it, be it our products, the type of shows that we create and then the type of sponsors that we bring on board.

Part of closing that engagement loop means bringing Bartlett's direct investments into the fold, literally.

UK Matcha brand Perfect Ted is a perfect example.

Bartlett met the founders through his time on investment show Dragon's Den.

Now, not only is he an investor, but Perfect Ted is a sponsor of The Diary of a CEO, and the company is moving its offices to Flight Story HQ.

This is the fastest growing.

Hashtag ad.

This is the fastest growing tea brand in the UK.

Is he here?

Teddy?

It's called Perfect Ted.

He's he's Teddy.

So it's named after him.

But very egotistical, right?

No, but it's a great name.

So I met I met um these guys, they came into Dragon's Den and um after a bit of a competitive bid, we ended up doing a deal.

And then the business went so well, so we ended up investing about a million more into the company.

And since then, it's just been the straight line upwards.

I really believe in the the power of like synchronous collaboration, and I think this is kind of been underestimated, especially in a post-pandemic world.

Where a lot of people now working from home.

But the value to them of being able to walk downstairs and say, what do you think about this and get an immediate answer and then be able to have an ad hoc brainstorming in a hallway about something quickly.

And to accelerate the pace of decision making in that regard.

You will achieve in six months what it takes your competitors to achieve.

So much of what we're doing around here is trying to accelerate the pace of decision making and increase urgency.

And proximity does that in a really helpful way.

This media model has helped elevate Bartlett and Flight Story to the upper echelon of new media.

Whose peers include those like Alex Cooper and Mr. Beast.

But Bartlett is taking his venture in a different direction.

While many podcasters like Alex Cooper, Joe Rogan and the Kelce brothers have signed hundred million dollar deals with streamers like Sirius XM, Spotify and Amazon.

Bartlett has turned down the offers he's received.

He set on building independently because it offers him flexibility.

To share his content across platform and experiment with what works.

It's working so far.

And as Georgie said, it wasn't through gut instinct, but rather in data science that Bartlett has cracked the code.

To building an empire on his own in this new media landscape.

I tend to think in terms of principles because a strategy is useful, but it like decays.

It's ephemeral.

So a strategy is like me giving you a fish.

But if I give you a principle, it's like me giving you the fishing rod so you can fish for yourself forever.

And one of the principles is that in the world we live in today, where the correct answer is changing faster and faster and faster.

The correct answer in technology is accelerating.

Which means the correct answer to anything, to how to shoot an interview, to how to make a podcast, to which platform to use, to where to put the meme bar on the video, what the title should be, what the color should be.

If you just understand that as like a principle, then the way to find the correct answer before everybody else is to increase your rate of experimentation.

So here, we have a full-time failure and experimentation team.

So that we can fail faster because failure is feedback, feedback is knowledge and knowledge is power.

So our rate of failure will correlate to our rate of success.

This is the Experimenter of the Week trophy.

This trophy every week goes to the person that has failed the most.

Conducted the most experiments, tried the most things.

And this week it went to two of our exceptional colleagues who have just been basically experimenting every single day.

And because of that, they've found all these incredible new ways to like scale.

I think it was mainly TikTok they'd done the experiments on.

And so we have our little presentation every week to who has failed the most and you win this trophy.

I think in terms of the speed, the urgency, the dedication to experimentation and testing.

The commitments to the 1%, the pursuit of the goal.

I think is something that energizes me in a way that I've never experienced before.

That we're in a pursuit of something here.

I think we can essentially kill the guessing now.

So I don't think we need to necessarily make these long-term strategic bets.

But we look at what the data insight and data science is telling us today.

And I almost think you can algorithmically edit now that we can think about how we structure content, what type of formats we utilize, what type of environments we show up in.

How we decentralize the media that we're producing.

How we essentially go wherever our audience is.

It's it's kind of an old publishing saying, which is you create great content and go where your audience are.

And I think that's probably what legacy media has lost as they get sort of caught up in their own ecosystems and business outcomes and platforms and serving investors and shareholders.

That perhaps they've lost sight of that really singular purpose, which is creating amazing content and going where your audience is.

But we wanted to know the one thing that data could not solve.

At least not completely.

The number one challenge is recruitment.

One of our biggest challenges is hiring.

It all comes down to people, really.

I'm recruiting seven days a week till 3:00 AM at night every night.

And it's my absolute obsession.

We do atypical things like we don't interview people in teams or in groups if we can help it.

Because we don't want to bring group think into a meeting.

We want independent assessment.

We use tools and surveys to understand about a candidate's values and how they think about the world and their work.

We now have a system through which we analyze our commitment to head hunting every single week and qualify that by the volume of hours we're taking.

All of our senior leaders and everyone in this team will tell us, I've spent eight hours, 10 hours, 12 hours head hunting this week to try and find the best people in the world.

And that is definitely paying dividends.

I realized that the game I'm actually playing, the first foundation of this whole thing called business, is not how good I am.

It is my ability to attract exceptional people to come work here.

And then job two is to bind them with a culture that makes them do the best work of their life.

And job number three is to set them a vision that is important and worthwhile.

And I think founders could save themselves so much hurt and pain and failure and anxiety and worry and confusion.

If they realized that they should be spending 20 times more hours per week on just meeting people and um professional flirting.

Essentially, Bartlett wants to find the people that might be equally obsessed with what the team is building.

And who have the ability to innovate and experiment the way he has.

After all, his ability to be a disruptor is what's gotten him here in the first place.

I struggled a lot in school because I find it difficult to pay attention.

Especially when I'm not interested in something.

So although my head teachers and my teachers still say that I was kind and nice.

I wouldn't do my homework and I wouldn't come to lessons.

Ultimately, that meant I was expelled, then unexpelled.

But the the thing I always had in me was I was really interested in business.

That was my curiosity.

The thing that I could pay attention to.

So I thought, well, the only way that I'm going to get to live a free life is if I create it myself.

And this is also part of the reason why I dropped out of university.

Because I asked myself the question, who am I going to show this piece of paper to if I want to work for myself?

I didn't know what the word entrepreneur was when I started my first business.

I didn't know how hard it was.

Maybe there was an element of like necessary delusion in thinking that I could have an idea and then there was nothing between me and the realization of that idea.

The single most important trait I had wasn't like smarts or intelligence.

I didn't have parents that could give me any money or anything like that.

The single trait I had was a healthy dose of delusion.

And that delusion is sometimes also referred to as self-belief.

So I started because I I didn't have a plan B.

And I was desperate for maybe through shame or insecurity, which was the sort of like subtle background murmur of shame my whole childhood.

And the way that I thought I could fill it was the validation from like doing something great with myself.

Or getting the money that was always like the the thing causing me awkwardness as a kid.

Whatever the like motivation was, whether I was being dragged or I was driven.

I just I just never felt like I had a plan B.

I started a company called Wallpark, which was a student notice board.

And that led me to understand this thing called social media and the power of it at a time when I think people were quite contrarian and negative towards it.

And we made a big bet on it.

He quickly realized that social media was the best way to drive traffic to Wallpark.

He went on to help other brands grow their social audiences and eventually launched social media startup Social Chain.

Which landed him a spot on the Forbes 30 Under 30 Europe list in 2020.

Really the most important thing from that period of my life was understanding this new attention economy.

Of being able to cultivate and build a big audience on the internet through content and the sort of art form and psychology of creating content and marketing and how to build a business.

And then an investor came along and invested more money, he became majority shareholder.

The business got to around 25 million in revenue between the UK team and the New York team.

And then we merged with a company called Limeland, making us a public company.

I then became co-CEOs with the the guy called Wanya Overhoff.

And for the next three to four years, we went on an acquisition spree, acquiring companies all over the world.

In 2020, we were about to up list again to another stock exchange called the Frankfurt Stock Exchange.

And right before then, I resigned.

Because I had lost control of the company.

So I could no longer make the decisions that I wanted to make.

From there, he began investing in more companies.

Even joining UK's investment show Dragon's Den for two seasons.

And he went all in on building The Diary of a CEO.

Like going from irregular posts to twice weekly uploads and incorporating video with the episodes, which was the critical difference in the show from what existed at the time.

My favorite quote ever.

Because it just like hit me like a ton of bricks many years later.

Is those that think they can and those that think they can't are both usually right.

And people think, well, if you're capable, you believe you can.

No.

It's because belief itself is the is the escape velocity of any hell or prison that you're in.

Throughout his entire career, Bartlett has stayed ahead of the curve.

He was an early adopter of social media marketing.

Took on podcasting before it was cool.

And now AI is top of mind.

We start experiments here with our experimentation team and a team a separate team that I call Flight X.

Their job is to disrupt the main business.

Because if you don't disrupt yourself, then someone else is going to.

That's what history tells us.

They call it the Innovator's Dilemma.

So their job has been to build AI podcasts that are better received, better retaining in terms of retention.

Than our current shows.

So one of the things they did.

Is they started a new show using me, although I didn't record it, I didn't write it.

Even the artwork wasn't created by me, wasn't published by me.

And it's live.

And it's doing very, very well.

And again, you just play forward any expected rate of improvement.

Let the writing part, the content writing part.

That AI did improve by 5% a year.

Or 5% a month.

It's really improving by about 10% a month.

Let the voice, the speech part get better by 5% every month.

And eventually you have yourself in a place where it is incomparable and equal to me.

Sat with nine cameras around me flying across the world to interview someone.

No one in my comment section has ever said, by the way, Steve, can we have some AI podcasts?

No one ever.

None of my sponsors on the show have ever gone, we'd really love to sponsor some AI podcasts.

So when I understand that, and I have the full picture of like how history plays out, I go, we've got to lean in early.

When it feels bizarre and we've got to start experimenting and messing around.

Because Steven Bartlett at 18 with that little social media thing was naive.

He didn't know how the old world worked of marketing.

So he leaned in and started messing around.

And this is what I'd tell my kids if I had kids today.

Hopefully I'll have some some soon.

I will tell them, I'm really not that bothered about like what you study or whatever.

But the most important thing to own a rapidly accelerating future is to lean in to bizarre behavior.

When something makes you feel a bit weird, when it goes against what you think you know, lean in.

And especially if there's lots of pessimists.

Because pessimism correlates to disruption.

I the more people that are slightly pissed off and criticizing the thing, probably relates to the amount of people who are experiencing the cognitive dissonance of, oh my God, I think this thing's going to kill my job.

So there's probably a big opportunity for disruption there.

And this is always the thing with innovation, you've got to realize that there's always a bulldozer coming for you.

It's coming for you.

It's coming for me.

It's coming for everybody listening.

And you have a choice, history shows us, to either be hit by the bulldozer or to drive the bulldozer and run your and run old you over.

So yes, I'm scared.

But what do you do with that energy?

Do you like ostrich in the sand it?

Or do you do something about it?

I think the next innovation based on what's happening in technology is we would technically only need one set like that.

Which is three digital screens to be able to shoot an endless amount of podcasts.

So hopefully in a couple of months time, if you come back here, what you'll see is you'll see three digital screens there, three digital screens there, three digital screens there.

And we'll be shooting 50 shows at once from this space.

And how it works is you walk up.

You click a button.

And that whole set changes to the Diary of a CEO, and all you have to do is roll in the Diary of a CEO chairs and table.

Which will be on a little rolling thing.

So that's never been done before in podcasting, but we really think it's the future of of this art form.

Now that the technology and the screens have gotten so good that you genuinely can't tell.

I think that the word podcast is certainly one that's up for debate at the moment.

And I really think about what we're doing here is producing influential and compelling IP.

And then really energizing a global fandom around it.

That transition from I guess legacy media brand to influential human IP is such an important and exciting conversation.

That's the one I'm most excited about versus sort of what a podcast is and what it might become in the future.

There's two really interesting things that have happened in the world, I think, over the last couple of years.

And it pertains to media and investing.

So on the media side of things, once upon a time, media and attention was owned.

Really by a couple of families.

And these families had the the microphone, the megaphone.

And because of what happened with the internet and social media, everything became more decentralized.

To the point that both you and me right now are publishers, whether we realize it or not.

And this is like unheard of, and I don't think we realize how significant this change is.

To to suddenly be in a world where we all have a megaphone.

And the thing that's not going out of fashion in a world of AI.

Is human to human relationships.

So I really, really believe that the future of media is human-led, human-hosted.

IP with an ecosystem built around it.

The best founders of our time that are building exceptional B2C and B2B companies, they no longer want money from men in suits.

They want something more.

They want growth and the path to growth is in this attention economy.

And what Flight Story endeavors to do is to bring some of the best voices in the world who are aspiring to drive a healthier, happier humanity.

Together with some of the best founders in the world who are building that happier, healthier future.

Together, we believe that we can give them the tools to make 1+1=3.