Great Business Stories

Look, I’d be lying if I said I’d always wanted to cover Chesky and Airbnb. I hadn’t really read much about either of them. The business itself sounds pretty humdrum. People renting out apartments, spare rooms. Nothing really new or exciting there. And Chesky himself has always flown under the radar. But each week the story I pick just depends on what catches my fancy and last week, for whatever reason, I thought, you know what, I know absolutely nothing about this guy. I want to dig into it. And what a story. Because Chesky and his co-founders basically took one of the crappiest business ideas — renting out airbeds on apartment floors — and through sheer tenacity and a fantastic understanding of how a product should work, they turned it into a $100 billion company. But it’s really the stories behind the company that make this so good. Making their own cereal to clear their debts. Not knowing what a slide deck or an angel investor was. Coming up against the king of the clones, the dreaded Samwer brothers from Germany, losing 80% of their business when Covid hit. It all makes for a cracking story. Enjoy.

As regular listeners will know, I’ve wanted to cover Thiel for some time now. He’s going to warrant a three-parter at least because, love him or loathe him, Thiel is without doubt one of the most interesting, controversial and polarising people in business over the last 30 years. For listeners who don’t know him, Thiel was part of what became known as the PayPal Mafia - this group of supersmart guys who founded and built PayPal. The company survived the dot-com crash, it almost went under because of Russian fraudsters and they eventually cashed out in 2002. And then a lot of the people involved went on to even more success. We’re talking Thiel himself, Elon Musk, David Sacks and Reid Hoffman. So this episode focuses on Thiel’s early life and brings us right up to the sale of PayPal in 2002. It is a cracking story. Enjoy.

Now I’m not a big petrol head, but as some of you might know, I love Formula 1, and I think it's fair to say that Formula 1 wouldn’t be where it is today without Ferrari—so I was really keen to dig into this. And what a story. Enzo Ferrari wasn’t your typical business guy. Most people think of Ferrari as a company that builds expensive road cars and also happens to race. But for Enzo Ferrari, the road car business was really secondary—those beautiful, expensive cars were made for one reason only—it was to fund his obsession with racing. And it was an obsession. He valued his engines more than his drivers. He had little time for his family, but still made time for numerous affairs. He could be a charming, funny and brilliant salesman, but he could also be cold, ruthless and very difficult. And he makes for a cracking story.

The whole WorldCom scandal never really registered with me- because it happened straight after the dotcom bubble burst, so myself and my cofounders were just dusting ourselves off and slowly realising that we weren’t going to suddenly become business tycoons and on top of that whole Enron scandal had exploded just a bit before so that was the story that consumed me back then - so when WorldCom went bust, I didn’t really give it a lot of time, but I knew in the back of my mind that there was great story here- Bernie Ebbers, this 6 foot 4, honest to goodness church-going cowboy who kind of came from nowhere to all of a sudden building one of the biggest telecom companies in the USA, until suddenly it all collapsed becoming the biggest bankruptcy in US history, far surpassing Enron and and I’m glad that I finally got round to digging into thai story because it really is a cracking one- enjoy

This is the remarkable story of how David and Frederick Barclay went from painters and decorators to owning the most prestigious hotels in London: the Ritz, Claridge's, the Connaught, the Berkeley. They bought the Telegraph Newspaper Group, they bought an island and built a £100 million castle on it, their fortune was estimated to be £7 billion pounds as late as 2020. But these guys, man, they were secretive, underhand — these guys pulled some very sneaky shit. And then it all came crashing down when the twins turned on each other, culminating in the Ritz Hotel bugging scandal. This is a sensational and cracking story — enjoy.

This is, without doubt, one of my favourite stories ever. And look, I'll be doing a good few episodes on Gates and Microsoft, but why I decided to start off with this one is because it's a fantastic standalone story. You have Bill Gates and Microsoft, in the mid-90s at the height of their power, and then along comes Marc Andreessen and Netscape, who develop a browser that really launches the World Wide Web. And this is an existential threat to Microsoft. They try to bully Netscape into a deal, but Netscape fight back, and this sets in motion an antitrust case that brings out Gates' arrogance, petulance and fear, and it leads to a judgement where Microsoft is ordered to split in two. This is a cracking story, enjoy.

I wanted to dig into this story purely because what I knew of Peloton really was just from the headlines. During the pandemic, stock pickers and the business media crowned Peloton the business of the future. It was called the Apple of fitness. You had the Obamas, Usain Bolt, Leonardo DiCaprio, dozens of high-profile celebrities as customers, and some of Peloton's live classes had bigger audiences than Madison Square Garden. And then, just as quickly, the same press that had lauded him turned on him. Foley and Peloton became the poster child for pandemic-era hubris. A company that reached a $49 billion valuation is now just worth $2.6 billion. Was it all Foley's fault? That's what we'll find out in today's episode. It's a cracking story, enjoy.

I've wanted to cover Milner ever since I first came across him in Sebastian Mallaby's excellent book, The Power Law, where Mallaby introduces Milner with the following: "At the start of 2009, the CFO at Facebook took a call from Moscow. A soft Russian voice announced that he wanted to invest in Facebook. The caller had a gentle but insistent style. He had a slight build, a nose bent to his right, and an oval face crowned by a smooth dome. He wanted to meet in person. Facebook did not accept capital from just anyone." The CFO told Milner bluntly: "Don't come all the way here just to see me." Milner booked a plane ticket, flew to San Francisco, and more or less doorstepped the CFO. This is the story of how this small, quietly spoken Russian goes from earning just $5 a month to reaching the very peak of Silicon Valley, investing in Facebook at a valuation that US investors thought was crazy, becoming one of Mark Zuckerberg's most trusted friends and advisors, and then going on to make huge and very successful investments in Spotify, Zynga, and Revolut, to name just a few. Along the way, Milner navigates his way through the oligarch-infested pools of Russian business, survives all of the political and media backlash that comes from the revelation that much of his early money came from entities closely linked to the Kremlin, and has come out the other side still riding high with a personal fortune of $8.7 billion. It's a cracking story—enjoy.

And let me start with a quote: "I didn't pull you out of Stanford Business School to bankrupt the company" — that's Bill Gates, early on, arguing with the man he'd just hired as Microsoft's first ever business manager. That man of course was Steve Ballmer, and the two of them would go on to build one of the most valuable companies in history together, through huge arguments, a legendary contract with IBM, and a decade of ruthless sales tactics that got Windows onto practically every computer on the planet. This episode takes Ballmer from his childhood right up to becoming Microsoft's CEO in 2000. It's a cracker — enjoy.

There are so many great characters in this story — I dig into the founder, David Cook, a guy who sold the business for $12 million but could have made $300 million if he'd stayed on for just a few more years. And then Wayne Huizenga, the guy who turbo-charged the business, after building his first fortune in the rough and tumble of the waste management business in the 70s and 80s. There's the now legendary meeting where Blockbuster's executives had the chance to buy a fledgling company called Netflix for $50 million but more or less laughed the Netflix founders out of the room. And then, as I've come to expect, Carl Icahn makes an appearance and bullies his way into the business, but makes a complete mess of it. It's a cracking story — enjoy.

This is a guy whose father fled Lebanon with almost nothing and today is worth $120 billion. I examine how he built his fortune buying up distressed businesses during Mexico's economic collapse of the 1980s, and how a controversial privatisation deal for the national phone company turned him into the richest man in the world. I also look at the huge criticism he's faced for monopolistic practices that cost ordinary Mexicans billions and also held back the development of an entire country, and how he's used that fortune combined with this intrinsic and intangible gift for numbers to make savvy investments in everything from Apple to the New York Times. It's a cracking story — enjoy.

This is a guy who grew up in a village in rural China with no running water and today is now worth $110 billion. I examine his relationship with Sam Bankman Fried- and his subsequent involvement in the multi billion dollar collapse of Bankman Fried’s company FTX. I also look at how he tried to keep Binance away from any type of regulation, and this ultimately led him to serve time in jail but then very controversially get a presidential pardon. It's a cracking story — enjoy.

I nitially I had intended to do just 1 episode on Hyundai, focusing mainly on the car business and it’s current leadership, but the story of Ju-yung is just too remarkable to be consigned to a footnote- this is a guy who, from nothing, built a conglomerate that at it’s peak in the 90s was one of the biggest companies in the world, with revenues of $90 billion, 200,000 employees, operating in everything from semi conductors, to cars, to ship building, to construction, to retail outlets- you name it, they did it and Ju-yung built it all through wars and military rulers, it’s a cracking story, enjoy.

Now, I’m not into fashion and I really didn’t know anything about Klein before I did my research for this episode and I found him to be such a fascinating character-how he, together with Ralph Lauren and Ann Klein, no relation, dragged American fashion out of the shadow of Paris and made it stand on its own two feet. How he didn’t do it on his own- Calvin Klein the business was always 2 people- Klein and Barry Schwartz, how Klein pioneered designer jeans, how he built his company while partying in Studio 54 and burning the candle at both ends, and how the business was just days from bankruptcy before David Geffen came to the rescue. Also, his marketing genius, he was behind some of the most controversial and influential ads of the 1980’s and 90’s. He makes for a cracking story, enjoy.

Sacks is a very interesting and powerful figure. He started his tech career with PayPal, and it was Sacks, together with other PayPal founders, who organised the coup that got Elon Musk fired as PayPal's CEO. He went on to start up Geni.com and Yammer, selling Yammer for $1.2 billion dollars. He then set up a venture firm and has risen to prominence through the All In podcast, and then in 2024 was made President Trump's AI and Crypto Tsar. It is he who is advising Trump on the type and the amount of regulation required for AI — an extremely powerful and important position. So who is Sacks, how did he get to where he is? This is a cracking episode — enjoy.

This is a story that I’ve wanted to get to the bottom of for years- for those of you who aren’t aware of who Calvi is- he was known as God’s Banker- the guy who managed the vatican;s money back in the 70’s and early 80’s and who was found hanged under Blackfriars bridge in 1982, and here's an excerpt from the BBC on Calvi: "Calvi was at the centre of an incredibly complex web of international fraud and intrigue. It involved the Italian banking world, the underworld, the Mafia, Freemasonry and, most startling of all, the Vatican. The banker's death would trigger a wide-ranging political and financial scandal in Italy. It would involve the disappearance of millions of dollars, and leave behind an enduring mystery.” So as you can imagine- this is a story that has so many different strands- you could do probably a dozen different stories from all of the characters and plot lines-but Calvi’s story shines a light on how corrupt Italy was- this is a cracking story- enjoy

The edge in the title refers to an advantage that Cohen had over the rest of the market-because he is considered without doubt one of the best intuitive traders ever- good enough that he took home $3.5 billion last year, rich enough to lose more than $1.5 billion in the whole Gamestop short squeeze and shrug it off but is his wealth and success all down to skill or does he cross the line, as prosecutors have tried to prove numerous times? It’s a cracking story enjoy

I chose this episode not only because it’s brilliant, but also because my youngest listener and favourite nephew has been bugging me to do the story of a leary for a long time now I’ll start with an excerpt from a profile the journalist Philip Watson did on O Leary: “Through a series of audacious business moves and a decidedly gunslinging approach to his opponents, Michael O Leary made Ryanair the most profitable low-cost carrier in Europe. As one business associate bluntly puts it: "When he goes into battle he boots the shit out of anyone or anything that gets in his way." And to give you an idea of O Leary view of business: “When you look at the number of stupid people who have succeeded in business, you clearly don’t have to be very bright. Business is all about getting your sales up and your costs down, the bit in the middle is profit.” O Leary took a tiny airline from almost bankruptcy into what is now the third most valuable airline in the world- he is without doubt one of the most unconventional, uncompromising and yet I think in a very round-about way, one of the most endearing and self-aware business people in the world and he makes for a cracking story- enjoy

I’ll open up with an excerpt from a fantastic New Yorker article on Altman: "Altman has a relentless will to power that, even among industrialists who put their names on spaceships, sets him apart- and according to an OpenAI board member: “He’s unconstrained by truth. He has two traits that are almost never seen in the same person. The first is a strong desire to please people, to be liked in any given interaction. The second is almost a sociopathic lack of concern for the consequences that may come from deceiving someone.” So in this episode I look at Altman’s progression from app developer to a massively successful investor- eventually accumulating a $3.5 billion fortune from his investments, to taking over and growing Y Combinator, the most influential incubator and to then battling Elon Musk to eventually take charge of Open AI and by the time we get to the end, at the age of just 38 he’s become one of the most influential and powerful people in business and technology. It’s a cracking story- enjoy.

I’m going to kick it off with this excerpt from Oliver Shah’s excellent book on Green called Damaged Goods : “Mr Toad-like in appearance, with a bulging belly and a mischievous grin, Green turned into a business celebrity, often spotted on the front row of fashion shows between Kate Moss and Anna Wintour. Nut-brown from the Riviera sun, his silver hair slicked back into a rat’s tail, he relished the role he had carved out for himself as the retail industry’s roguish uncle. Bankers from Goldman Sachs and HSBC fell over themselves to offer him money and advice. Simon Cowell and Ronnie Wood attended his parties. He paid his wife almost £2bn of offshore dividends from his high-street empire and made two headline-grabbing hostile takeover attempts for Marks & Spencer. He was knighted by Tony Blair. It all came crashing down in 2016.” And that is the story I’m going to tell today—Philip Green, the one-time king of the high street. The opulent lifestyle, the aggression, the bullying, the greed—it’s a cracking story. Enjoy.