#65 Kirk Kerkorian: Penniless Dropout became the Greatest Deal Maker in Capitalist History artwork

#65 Kirk Kerkorian: Penniless Dropout became the Greatest Deal Maker in Capitalist History

Founders

March 31, 2019

What I learned from reading The Gambler: How Penniless Dropout Kirk Kerkorian Became the Greatest Deal Maker in Capitalist History by William C. Rempel.
Speakers: David Senra
**David Senra** (0:00)
I want to tell you about a one-time only limited event that I don't think you're going to want to miss. I am doing a live show with Patrick O'Shaughnessy from the Invest Like the Best podcast in New York City on October 19th. Patrick has interviewed over 300 of the world's best investors and founders for his podcast. I've read over 300 biographies of history's greatest entrepreneurs for my podcast. We'll be talking about what we learned from seven years of podcasting, sharing our favorite ideas and stories, and doing a live Q&A. There will also be special event-only swag. If you live in New York City, I think it's a no-brainer. But if not, I think it's a great excuse to fly in. I've already heard from a bunch of people that bought tickets, they're flying in from other cities. Some people are flying in from other countries. That's setting the bar really high, so I will have at least four shots of espresso or four energy drinks before or during the show so we can make it a night that you'll never forget. If you're interested in attending this unique live event, I will leave a link down below. I highly recommend you get your tickets today, and I hope I get to see you in New York on October 19th. There is an inspiring life story in the 98 years that belonged to Kirk Kerkorian, a boy who ran barefoot in the rich dirt of California's San Joaquin Valley before family financial chaos made him a city boy fighting for his place on the dirty sidewalks of Los Angeles.
He was a tough guy who wept at funerals, a humble man privately proud of his accomplishments, a business genius who ignored his MBA advisors, a daring aviator and a movie mogul, a gambler at the casinos and on Wall Street who played the odds in both houses with uncanny skill. That is an excerpt from the book that I'm going to talk to you about today, which is The Gambler, How Penniless Dropout Kirk Kerkorian Became the Greatest Dealmaker in Capitalist History.
So let's start with his personality, his early life, and some of his accomplishments.
So it says, Kirk was uncomfortable in crowds and dreaded the attention of strangers. His lifelong aversion to the trappings of celebrity would make him what he remains years after his death, one of the least known of America's richest men. He seemed to burst out of nowhere onto the American business scene in the late 1960s.
A small businessman with a gambling habit and a junior high school education who struck it rich at the mature age of 50 He dropped out, and we'll get to that too, but he dropped out in eighth grade. He was a heroic wartime aviator who ferried factory fresh bombers and fighter planes for the Royal Air Force over the treacherous North Atlantic in the era before navigational aids. He nursed a small charter air service through cycles of hard times after the war until selling his company for a windfall fortune. But the gambler decided to bet it all on some kind of capitalist trifecta. Suddenly, he was on business news pages across the country, risking huge sums in a puzzling range of eclectic markets.
On the West Coast, he moved to control America's oldest commercial airline. In New York and Hollywood, he waged a takeover battle for the faltering, befabled MGM studios. In Las Vegas, he built the world's biggest hotel, despite a secret campaign to stop him by rival Howard Hughes. So let me actually just stop there. So somebody sent me, suggested I cover this book. They sent it to me on Twitter, like, a few months ago. And I had it on my wish list. I don't think I had ordered it yet. And then about a month ago, I did a podcast on Howard Hughes. And in the, the, it's, it was, the author sourcing for the Howard Hughes book, or a lot of the author sourcing, was all these memos that Howard Hughes would write, especially later on in his life, when he was basically a recluse. He'd write written instructions for, like, his staff. Like, they were known as, like, the Mormons. I mean, the staff, like, five or seven people, like, basically were his buffer between his little penthouse, where he never left, and the outside world. So anyways, a lot of those memos in the book, they brought up the fact that Howard Hughes was, even though he would never appear in public, he was insanely jealous when other people would, other entrepreneurs would receive attention. So at the same time that Howard Hughes was living in the Desert Inn in Las Vegas, Kirk Kerkorian is, like, developing a lot of the hotels there. And so because he's developing hotels there, he's written about it in the press. And so Howard Hughes actually starts writing these memos, like, on how to destroy Kirk. Now, I bring that up is because Kirk never knew that, first of all. And second of all, he admired Howard Hughes. So if you remember all the different industries that Howard was involved in, Kirk kind of... I'm not saying he copied Howard Hughes, but he certainly admired him. He was an aviator and a pilot, just like Howard was. He winds up owning a movie studio, just like Howard did. He winds up developing real estate in Las Vegas, just like Howard did. They have a lot of the same ideas, and they work in a lot of the same industries. So Howard Hughes is in this book a lot. I'll probably talk about him a few times, but it's just good to know that Kirk was about 15 years younger than him and definitely admired Howard's accomplishments that was not reciprocated. Howard was by that time a drug addict and rather paranoid, as I covered in that podcast. Okay, friends would call him a deal junkie, addicted to financial thrills, whether at a craps table or at the negotiating table. In business, as in gambling, Kirk believed that there was no point in placing small bets.

60 more minutes of transcript below

Feed this to your agent

Try it now — copy, paste, done:

curl -H "x-api-key: pt_demo" \
  https://spoken.md/transcripts/1000516289662

Works with Claude, ChatGPT, Cursor, and any agent that makes HTTP calls.

From $0.10 per transcript. No subscription. Credits never expire.

Using your own key:

curl -H "x-api-key: YOUR_KEY" \
  https://spoken.md/transcripts/1000516289662