Great Business Stories

Michael O Leary: The Jumped up Paddy Who Doesn’t Give a Shit

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

Sam Altman: 1985-2023

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.

Philip Green:The Unacceptable Face of Capitalism

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.

Bill Ackman: 1966–2008

I’m breaking up Ackman’s story into three, maybe even four parts because, like him or loathe him, Ackman is a very interesting character. I’ll kick it off with a quote from Carl Icahn, the legendary Wall Street investor who has tussled with Ackman on more than one occasion, and this kind of encapsulates the core of Ackman’s character: “I would be a very happy man in life if I could be as certain of just one thing as he is certain about everything.” And really, that’s Ackman in a nutshell—supremely, annoyingly confident, to the point of arrogance. Yet it is this confidence, combined with intelligence and persistence, that has resulted in the Ackman we know today—sticking his nose into everything from college admissions, to DEI, to Israel and Ukraine, while also building up a fortune estimated to be $9.6 billion at the time of recording. So in this episode, I dig into how he started off. It’s a fascinating story. Enjoy.

Ross Perot: Shorty Got Game

I’m having a bit of a dig at Ross Perot’s height, but for a little guy, this guy had a lot of game—not just as a businessman. This guy could have been the US President. Here is a quote from Time Magazine from 1992, when he threw his hat into the ring to become president: "It's hard to envision a seriously short guy who sounds like a chihuahua as a charismatic threat to democracy, but it is delicious to watch the thrills of horror running through the establishment at the mere thought." Because as we’ll see in the story, Perot came this close to becoming the President of the United States in 1992. But this is a business story, so we will also, of course, be talking about his business achievements, which are just as big. He was IBM’s top salesman. He coined the term facilities management and created the first professional business model around it. Then he built and sold two multi-billion dollar companies. And even more intriguingly, he hired a special ops commander who then trained some of his own employees, and then they flew into Tehran and helped break two of Perot’s employees out of a jail in Iran. I mean, this story has it all. It is brilliant. Enjoy.