As Kirk Kerkorian transitioned from aviation entrepreneur to investor, he also got into real estate development. Per his biography, he took $960,000 from the sale of Trans International Airlines in 1962 and bought eighty acres in Las Vegas. In 1963, a developer leased the land to build Caesars Palace. Kirk would get lease payments and 15% of casino profits.

Caesars Palace educated Kirk on casino development. He made plans to build his own hotel and casino. The International Hotel would have 1,000 rooms and be the world’s largest. He paid $5 million for sixty-five acres and another $12.5 million to buy the Flamingo Hotel so he could train staff while his hotel was being built.

The Flamingo was built by Bugsy Siegel in the 1940s and had been run by the mafia since then. It reported profits of less than $500,000 annually. In its first year under Kirk’s ownership, it made $3 million, more than Kirk’s $1 million projection. This increase in profits would be a double-edged sword.

Kirk wanted to focus on his project, so he sold the land underneath Caesars Place for $5 million, returning $9 million total on his five-year investment.

Kirk was thinking big. He believed leisure travel was on the verge of exploding. He bought the bankrupt Bonanza Hotel and Casino and the second mortgage on Circus Circus resort and created the International Leisure Corporation (ILC) to own them and the Flamingo and International Hotels.

In 1969, he took ILC public and raised $26 million. Later that year, the International Hotel, which cost $60 million to build, opened and was wildly successful. With two successful hotels and casinos, ILC’s stock rose. Kirk’s eighty-two percent ownership was worth $180 million.

ILC had $50 million in debt, which Kirk planned to pay off by issuing more ILC stock. Unfortunately, the SEC wouldn’t let him because it questioned the recordkeeping at the Flamingo before Kirk bought it. Simultaneously, a bear market hit stocks. ILC’s stock dropped 90%, from $65 to $6.50. Kirk needed to raise cash. He sold his yacht, private plane, and roughly half of his ILC stock. His stock had been worth $180 million months earlier, but Hilton Hotels bought half of Kirk’s position for $19.4 million. Hilton owned 50% of ILC, for which it paid only $21.4 million. Leverage forced Kirk to sell at the worst possible time and lose control.

Kirk hated having partners. By 1970 Hilton was renaming the International Hotel as the Hilton Las Vegas. This, combined with wanting to pay off other debts, led to Kirk selling his remaining ILC shares. He was no longer in control of what he’d built and was out of the casino business for the time being. Things weren’t all bad. He made a roughly $30 million profit after ILC’s stock sales and dividends were factored in.

“I have no regrets,” Kirk said. But he learned valuable lessons: first, that ownership and control mattered in the companies he created, and second, that he, like his father, was susceptible to being crushed by financial leverage at the worst possible time.

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Kirk Kerkorian’s charter airline, Trans International Airlines (TIA), was doing well—so well that in 1962, Studebaker Corporation offered to acquire it by assuming all Kirk’s debt and giving him $1 million in Studebaker stock, for a total deal value of $10 million. Kirk agreed and became a millionaire.

Kirk's biography says Studebaker fell on hard times and sold TIA back to Kirk two years later, in 1964, for just $2.5 million. He borrowed $2 million from Bank of America and closed the deal. By now having a better understanding of the stock market, Kirk took TIA public in 1965. As the company’s performance improved and the Armenian community supported the stock, it soared. In a few months, Kirk paid off the bank loan and owned stock worth $66 million at the age of 48. Three years later, in 1968, he sold TIA to Transamerica Corporation in a deal that gave him $100 million in Transamerica stock.

To recap, Kirk started his first flight school and charter company around 1945. Roughly twenty years later, he’d turned that idea into a publicly traded company in which he had a personal ownership worth $66 million. Three years later, he was Transamerica Corporation’s largest individual shareholder with ownership exceeding $100 million. That’s a remarkable accomplishment, especially considering his humble beginnings.

During this period, Kirk evolved. He transitioned away from being solely a hands-on aviation operator and builder, learning and acquiring skills around mergers and acquisitions and navigating the stock market. He used those skills to add public market investing to his resume. Kirk was no longer just an aviation entrepreneur.

His ability to level up stood out to me, especially considering that the above was only part of what he juggled during this period. He was also beginning to acquire land and consider entering the casino market.

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In Sumner Redstone’s autobiography, he told us about his epic battle with Kirk Kerkorian over MGM/UA Home Entertainment Group. I know nothing about MGM/UA or Kerkorian, so I started reading William C. Rempel’s biography of him, The Gambler: How Penniless Dropout Kirk Kerkorian Became the Greatest Deal Maker in Capitalist History. I’ve read a third of the book so far, and it’s an incredible entrepreneurial story.

Kirk’s first business was cleaning up old cars and reselling them for a profit. After getting the flying bug, he became a pilot for the Royal Air Force Ferry Command (RAF) during World War II, earning hefty hazard pay of $1,000 a month to deliver warplanes across the Atlantic. He did all this despite having only an eighth-grade education.

After World War II, the aviation industry took off, as did the demand for pilots. In 1945, Kirk started a flight school and eventually a charter airline, too. His customers flew frequently to Las Vegas, a desert city of saloons and small casinos. Kirk loved the excitement of the city, something he’d missed since flying dangerous missions for RFA.

Kirk decided he wanted his own airline, but he was short on capital. He started buying surplus World War II military planes, refurbishing them, and reselling them. At roughly age thirty-five, Kirk was making over $100,000 a year. He learned that pilots don’t make big money, but businessmen do. He became a major player in the used airplane brokerage and charter businesses between his home base in Los Angeles and Las Vegas.

Kirk’s chartering niche to Las Vegas led to friendships with celebrities and casino bosses (including Bugsy Siegel). His clients schooled Kirk on the lucrative casino business. He wanted in and, in 1955, invested $50,000 for a roughly 1% stake in the Dunes Hotel & Country Club, which ran into trouble. Kirk’s investment went to zero, but by then he was making roughly $300,000 a year from aviation. The loss was a painful and important lesson about the casino business.

By 1962, commercial airlines were moving to jetliners, and Kirk recognized an opportunity to become the first charter service using jetliners. He wanted to be the first government contractor to move cargo worldwide via jetliners. The planes cost $5 million, money he didn’t have. He convinced Bank of America to loan him $2 million and for the aircraft manufacturer to finance the remaining $3 million (unheard of at the time). He was officially in the postwar charter business, flying loads between US military bases worldwide. The move was lucrative. His company’s annual profits soared from $250,000 to $1.1 million in year one.

By his forties, Kirk was wildly successful. A key to his success was recognizing trends early. He repeatedly found and capitalized on them, often finding other trends in the process. His relationships and early understanding of Las Vegas and the casinos would play a major role in his future.

I’m looking forward to reading the rest of this book.

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I finished reading How to Get Rich: One of the World's Greatest Entrepreneurs Shares His Secrets by Felix Dennis today.

This book isn’t just about getting rich. It’s about succeeding as an entrepreneur. Riches are a byproduct of building a successful company. That mental framing was helpful as I read the book.

Here are my takeaways from the last third of the book:

Part Three: Succeeding as an Entrepreneur

• Focus – Felix Dennis’s goal was to create wealth for himself. After stumbling into magazines and succeeding, he believed he was “born a magazine publisher.” He regrets lying to himself. Focusing on something he didn’t love but happened to be good at “cut me off from more lucrative endeavors,” he said. Magazine publishing is a mature business, so outsize success was harder to achieve and took longer. He advises staying focused on your objective (for him, wealth) and picking the best path to that goal (i.e., an industry with a tailwind).
• Luck – Dennis and a partner decided to write a biography of Bruce Lee. Sadly, Lee unexpectedly died young just as they were finishing the book. International demand for their biography rocketed, and that led to several other opportunities. Their focus on Lee’s biography put them in a position to capitalize after his tragic passing. This morbid story highlights Dennis’s psychology (for better or worse) and how luck isn’t always blind. Focus and hard work often precede lucky breaks.
• Do an outstanding job – Your company should always do an outstanding job. High-quality people are attracted to quality products and services, so you’ll attract and hire the best talent. The company will make fewer errors, which will reduce costs. If your company is known for quality, it will get a premium valuation and you’ll be wealthier (on paper). And doing a good job is just more fun.

Part Four: The Endgame

• Closing costs – The cost of shuttering a business can be material, and founders underestimate that fact. Selling the business for anything is better than shutting it down.
• Selling a failing business – Determine your financial runway. Think about ways competitors can use what you’ve built. Think of ways you can modify the business. Articulate how your business could add value to acquirers as-is or in a modified form. Start letting people know the business is for sale and how it can add value to their operations. Two interested parties equal a sale process. It takes only one to close a deal.
• Shuttering the business – Closing is the last resort. Pursue this path only after you’ve tried to sell the business. Never announce the business is winding down until you’ve exhausted all options for selling.

I now understand why Dennis wrote this book. He genuinely wanted to help other people become successful entrepreneurs and achieve financial independence. Sharing what he learned the hard way was his way of giving back.

Dennis was a colorful, mercenary entrepreneur. He started multiple businesses, and I didn’t pick up on a burning passion for any of them. He wanted financial freedom and everything that came with it, which wasn’t always good for Dennis.

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I’ve read two-thirds of Felix Dennis’s book How to Get Rich: One of the World's Greatest Entrepreneurs Shares His Secrets. Dennis pairs the wisdom he gained with entertaining stories from his journey. Dennis was a colorful person, and I’m starting to get a feel for the type of founder he was.

As I said yesterday, this book is about how to succeed as an entrepreneur, not just how to get rich. That mental framing was helpful as I read the book. I’ll keep swapping the two terms in this post.

Here are my takeaways from the second third of the book:

Part Three: Succeeding as an Entrepreneur

• Persistence – Persistent people have the conviction that they’re right and that that will be confirmed shortly. Stubbornness is persisting even when there’s plenty of evidence that you’re wrong or that you shouldn’t. Acknowledging a mistake and realizing a new plan is needed are signs of clear thinking and help focus your persistence on the right activities. The most successful people I know are persistent but also rational and clear thinkers.
• Instincts – Trusting your own judgment is essential to success. Always be on high alert and looking for opportunities. When you find one, trust your instincts and move fast. Making judgment calls quickly is instinctual. If you deliberate too much, it’s hard to develop your instincts or trust your judgment.
• Evolve or die – Learning to evolve is essential to survival. If someone is going to “strangle your baby,” it’d better be you. If your product is going to be cannibalized, it’d better be by you, not your competitor.
• Listen and learn – Talking to team members and industry friends is necessary, but the real learning happens when you talk to people you don’t know, or who work in an obscure corner of your industry you’re less familiar with. If you’re not learning, you’re slowly dying. Make listening and learning priorities, or your days are numbered.
• Luck – Two things are part of getting lucky. Preparation is required to capitalize on an opportunity. “Do the heavy lifting work and homework in advance.” You must also recognize an opportunity when it happens. Don’t be so buried in the details you can’t see an opportunity that’s right in front of you. Luck tends to evade micromanagers and people who can’t let go. Stay alert and on the lookout for your lucky break.
• Balance of weakness – In negotiations, usually, both parties have a weakness—to one degree or another. Determining which weakness is most pressing and “potentially catastrophic to which party” is key. The “immediate balance of weaknesses may well prove more decisive than any long-term balance of strengths.” Weaknesses are usually hidden. Make it your top priority to determine the balance of weakness in negotiations. If their need outweighs your greed, you’re in a great negotiating position.
• Delegation – People are your most precious asset. Delegation is a tool to incentivize your people and bring out the best in them. They’ll make mistakes as they learn, but as your people succeed, your company succeeds.

Dennis’s wisdom is simple but not easy. I’m looking forward to finishing this book.

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Today, I started reading a book that’s outside my norm. Felix Dennis, the founder of Dennis Publishing and Maxim magazine, wrote How to Get Rich: One of the World's Greatest Entrepreneurs Shares His Secrets. The book is a collection of lessons Dennis learned during his journey. The title isn’t my favorite, but it matches the author’s personality.

Instead of how to get rich, I think this book shares how to succeed as an entrepreneur. I used this mental framing as I read the book. I’ll swap the two terms in this post.

Here are my takeaways from the first third of the book:

Part One: Pole Positions

• Young, penniless and inexperienced – People in this state are more likely to succeed for a few reasons. Because they lack experience, they’re likelier to learn new problem-solving methods. They have more stamina. Their risk tolerance is higher because they have almost nothing to lose. Dennis suggests that seasoned professionals considering entrepreneurship partner with someone young, broke, and inexperienced.

Part Two: Getting Started

• Fear of failure – People often fail to launch a company because they’re afraid. Failing publicly highlights mistakes and errors in judgment to others, which is embarrassing. I believe that entrepreneurs will experience a lot of failures as they experiment, so a thick skin and viewing failures as opportunities to learn are essential. Also, winning fixes everything. Success is what people remember, not failure.  
• New industries – New or rapidly growing industries increase your chances of success. Often, more risk capital is available from investors seeking large returns, which can lead to founders maintaining more control. Not much is known in new industries, so you can establish yourself as an expert quickly (if you work to learn), and a rising tide masks mistakes.
• The trifecta – Look for opportunities that align with your inclinations, aptitude, and fate. Inclinations are your natural interests. Aptitude is something you’re naturally good at (ask others if you’re unsure). Fate is luck or serendipity. When an opportunity aligns with all three, ignore the naysayers and quickly seize it before it’s gone.
• Reinforcing failure – A common start-up error. Knowing whether to keep pushing when something isn’t working or give up is difficult but important. Success may be just around the corner, or it may never come. Dennis believes timing plays a big part in success. Looking at the data beneath the surface level for signs of being too early or too late can help you avoid reinforcing a failure.
• Thinking small and acting big – Another common start-up error. Never disregard bold or new ideas (thinking small). Never think you’re above doing the things that lead to your success (acting big). Dennis regretfully shares a crazy period in his life when he spent over $100 million within ten years thinking small and acting big. Keep doing the things that led to your success (acting small) and thinking of bold ways to succeed (thinking big).

So far, this book is colorful and full of entrepreneurial wisdom. I’m looking forward to finishing it.

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I finished reading Sumner Redstone’s autobiography, A Passion to Win. The book gave me insight into Redstone as a person. It describes how Redstone took National Amusements, Inc. (NAI) from a family-owned, drive-in theatre business to a publicly traded media empire worth tens of billions of dollars. At the time of the book’s publication in 2001, Redstone’s empire included cable channels, movie theatres, radio stations, broadcast stations, and much more.

Redstone recognized that he needed to be in the content business. Drive-in theatre growth was slowing because of cable, and he was tired of fighting studios. If he couldn’t beat them, he would own them—partially at least. He used NAI’s cash flow to buy substantial ownership in publicly traded movie studios such as Disney and MGM. Redstone scored profits of tens of millions of dollars each on several investments. He profited by $26 million—a roughly 100% return—when Coca-Cola bought Columbia Pictures in 1982. Redstone’s ownership in studios was profitable, educated him on the business, and deepened his industry relationships.

When the leveraged-buyout craze began in the 1980s, Redstone found himself battling with raiders and others who were trying to buy public companies he owned at valuations he thought were too low. In 1986, at age 63, he found himself in a battle over Viacom International, a cable and television programming business that owned MTV, Lifetime, and other assets. After digging into the company’s potential, he decided to buy it outright. He learned to raise debt and fought ferociously to secure the deal (crazy story in the book!). In 1987 he closed the deal. After spending $3.4 billion, he was finally in the content business.

The deal proved lucrative. MTV ended up being a cultural force with a young audience. The channel was the cornerstone of Viacom, “providing more than 50 percent of Viacom’s cashflow” annually in the 1990s. The Cosby Show was another amazing asset. In 1989, its syndication sales were $4 million for each of its 125 episodes. The syndication of that show brought in $500 million to Viacom that year, a record at the time.

Redstone took things further in 1994. He acquired Paramount Pictures for over $10 billion after a brutal battle against Barry Diller and John Malone (another crazy story!) while simultaneously acquiring Blockbuster Video. At roughly age 71, he was in the business of creating movies and producing broadcast television shows (e.g., MacGyver). He owned a library of almost 800 classic films, including The Godfather and the Indiana Jones movies. He also owned the leading video rental company, which would quickly become a thorn in his side.

In 1999, at age 76, Redstone acquired CBS Broadcasting Inc. for $32 billion. CBS was an advertising powerhouse offering radio, cable, and broadcast channels and outdoor advertising (billboards). Surprisingly, this mega deal didn’t involve any battles.

He was number one in radio, cable programming, and outdoor advertising and “would own the number-one audience deliverer both nationally and locally in television.”

Sumner was “the king of content as well as king of distribution.” He had finally won.

Read my first and second parts of this series on Sumner Redstone here and here.

Note: If you’re interested, the book provides granular specifics on negotiations and financials for each deal mentioned above.

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I’ve read two-thirds of Sumner Redstone’s autobiography, A Passion to Win. The intensity and drive that Sumner Redstone developed in his early life served him well when he transitioned from practicing law to being an entrepreneur.

Redstone joined his father’s company, eventually known as National Amusements, Inc. (NAI). His annual salary went from $100,000 as a lawyer to $5,000. The company was a drive-in movie theatre business, and Redstone rapidly expanded it. NAI was a smaller player with theatres outside urban areas. Getting allocation for popular films, or the right to play them as soon as they were released, was an issue that hampered the company’s growth. Redstone saw this as unfair. Wanting the right to show the most desirable movies just like his big-city competitors did, he pleaded his case to studios with no luck.

Refusing to lose and accept unfair business practices, he sued the studios in 1958. Redstone’s move was risky because he was suing his suppliers. It was a David-vs.-Goliath battle that other theatre owners refused to fight. If he lost, his suppliers could severely punish NAI for challenging entrenched business norms.

The studios gave in and settled, giving Redstone most of what he wanted. Winning this battle was pivotal for Redstone. It told him the legal system could help him change an industry that was set in its ways and level what he saw as an unfair playing field. Redstone had found his edge. He’d found a way to fight and win.

He used the law again to fight Disney over a practice of blind bidding. Movie companies made theatres pay large, guaranteed advances for the right to show a new movie though they couldn’t screen it to evaluate its quality. NAI lost $400,000 on one movie, a massive sum for the company, and Redstone sued Disney and other major movie companies for acting as an oligopoly. He wanted a fair marketplace with “asymmetry of information” eliminated; i.e., he wanted theatres to be able to evaluate the quality of movies before bidding for the right to show them. Disney settled with him, and over time the practice disappeared from the industry.

Redstone’s intensity, drive to win, and advanced understanding of the law made him a formidable opponent and a force to reckon with. His hard-nosed strategies paved the way for NAI’s growth for the next twenty years. But not even Redstone could fight the change sweeping the entertainment industry in the 1970s and 1980s. Cable television was a Goliath like nothing he’d seen before, and he would have to devise a new strategy for NAI to continue growing and for him to continue winning.

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Reading about John Malone’s journey with TCI and Sheila and Robert “Bob” Johnson’s BET journey led me to Sumner Redstone. Redstone’s Viacom purchased BET for $2.3 billion in stock in 2000. Malone received $850 million; Johnson, $1.4 billion. I wanted to understand the man behind this transaction, so I began reading his autobiography, A Passion to Win.

What immediately stood out to me were Redstone’s years before his business career and his intensity. Redstone’s father was a street-smart entrepreneur, and his mother was a homemaker who made education a priority and instilled the importance of diligence and concentration in her children. He said that his mother “was a constant driving force in my life, and though I often resented her presence, I could never challenge her.”

Redstone attended Boston Latin School, one of the most rigorous schools in Boston and the oldest existing school in the U.S. Redstone said that the “school demanded an obsessive, driving commitment to excellence from everyone. A passion to win.” He wrote that the “competition [at his school] was cruel, it seemed inhuman . . . . And it taught [students] to pursue excellence for the rest of [their] lives.” There Redstone “was first exposed to the idea that thinking, educated and disciplined people have the power within themselves to create a new and better world.”

Sumner did nothing but study. “Throughout high school I don’t remember eating,” he said. He graduated with the highest grade-point average in the school’s three-hundred-year history and was awarded a full scholarship to Harvard University.

As an undergraduate, Redstone was disappointed by Harvard. "There was no feeling of daily individual competition, no sense of intensity, no battle of intellects." He said, “I was disappointed; the rigor I expected from the educational world was nowhere present.” He promptly finished all the required coursework in a little over two years. During World War II, he joined the army, where he worked to break codes transmitted by the Japanese military.

Based in DC, he worked the graveyard shift for the army and attended Georgetown Law School during the day. His first year, he ranked first in his class. After he left the army, he was accepted to Harvard Law for his second year.

He took a coveted clerkship for a judge in San Francisco for a year and then worked as an attorney for the Department of Justice. There, he handled and argued “tax cases involving hundreds of millions of dollars.” He won seventeen straight cases. After five years, he joined a private practice.

At his firm, he did antitrust and tax work and eventually argued an important tax case before the Supreme Court. He won the case, cementing his reputation as a top tax attorney.

In 1954, he was six or seven years out of law school, about 30 years old, and making $100,000 a year, or roughly $1.1 million in 2024 dollars. He came to realize that “[w]hen you’re practicing law, it’s just a business. It’s not a crusade for humanity, it’s a business.” This realization led to his decision to quit and go into business for himself.

Redstone’s early years shaped who he became. He was an intense, driven person who enjoyed a battle. These characteristics fueled the building of a media empire.

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I’ve finished rereading Ed Thorp’s autobiography, A Man for All Markets: From Las Vegas to Wall Street, How I Beat the Dealer and the Market.

My last two posts covered Thorp’s rise from living in a house with fourteen people to academia to founding the hedge fund Princeton Newport Partners (PNP). PNP turbocharged his life’s trajectory, but then it encountered problems it would never recover from.

Jay Regan, Thorp’s partner, ran the Princeton, New Jersey, office, while Thorp ran the Newport Beach, California, office. In late 1987, Rudy Giuliani, US Attorney for the Southern District of New York, was after Michael Milken and Robert Freedman. Regan was friends with both of them and did business with them through PNP’s Princeton office. The office was raided by federal authorities, and Regan and four other leaders in that office were charged with various crimes. They were convicted, but years later their convictions were reversed on appeal; all charges were eventually dropped. Authorities never questioned anyone at the Newport Beach office, and Thorp and his office weren’t aware of what allegedly was happening in Princeton. They learned the details from PNP’s lawyers and news reports. The ordeal resulted in PNP winding down.

After leaving PNP, Thorp reflected on his next steps. He had more money than he could spend and decided to optimize his time for travel, time with his wife and kids, and exploring interesting problems.

Thorp went through a “period of adjustment,” he said. He consulted for an institutional investor, which led to his uncovering Bernie Madoff’s Ponzi scheme in 1991. He restarted his hedge fund operations with only four team members and focused narrowly on hedging Japanese warrants and investing in other hedge funds. In 1990, Ken Griffin was trading options and convertible bonds from his Harvard dorm room. Thorp recognized Griffin’s potential, shared PNP’s secrets with him, and became the first investor (i.e., limited partner) in Griffin’s new Citadel Investment Group. Thorp also came close to seeding David Shaw, founder of DE Shaw, the hedge fund that Jeff Bezos quit to start Amazon.com.  

In 1992, Thorp restarted his statistical arbitrage operations, choosing to manage a single large account for a large institution. In 1994, he launched Ridgeline Partners to manage his and others’ money. Between the two, he managed over $450 million (PNP’s peak had been $272 million). Thorp’s staff at PNP had been roughly eighty people across both offices. To run Ridgeline and the managed account, he had six people. He’d figured out how to run his new hedge fund in a way that suited the life he wanted to live.

In 2002, Thorp decided to wind down Ridgeline. More hedge funds were using statistical arbitrage strategies, which reduced the number of investable opportunities and thus his firm’s returns. More importantly, he wanted to have more time to enjoy his children and grandchildren and his wife. When she died of cancer in 2011, Thorp was thankful he’d prioritized time with her over making more money.

PNP’s demise was “traumatic” and likely destroyed future wealth in the billions for Thorp. Thorp wisely used that event to transition to the third phase of his life—one centered on spending time with people he cared about, not wealth accumulation. He continued to invest and solve interesting problems in a way that best served his new way of living. Thorp had created his ideal life.

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