Last month, I posted about a book about William Richard "Billy" Wilkerson, who founded The Hollywood Reporter and the Flamingo Hotel in Las Vegas. The Man Who Invented Las Vegas, written by his son, W.R. Wilkerson III, focused on Wilkerson’s Flamingo Hotel project. I wanted to learn more about how Wilkerson built The Hollywood Reporter and his other Hollywood businesses, so I read Hollywood Godfather: The Life and Crimes of Billy Wilkerson, also by W.R. Wilkerson III.

Billy’s dad, William Richard Wilkerson Sr., was a prolific gambler and alcoholic who passed out drunk after gambling while Billy was being born in 1890 in Nashville, Tennessee. He physically and verbally abused Billy, his only child, to the point where Billy’s mother, Mary, transferred him to a school run by Benedictine monks in Alabama. Billy flourished in the religious environment and transferred to Mount St. Mary’s prep school in Maryland in 1904. When Billy declared his intention of studying for the priesthood, his father went ballistic. He forced Billy to attend medical school.

In 1912, his father died, and Billy, who had failed almost half his courses that year, dropped out to support himself and his mother. He also married Helen Durkin that year. Billy started working at Lubin Manufacturing Company, which produced low-budget comedic shorts in Philadelphia. Lubkin shuttered five years later, and in 1916 Billy began managing a New Jersey nickelodeon his medical school friend had won in a bet. Billy renovated the nickelodeon to appeal to the highest-end customers so he could charge the highest prices. Within six months, it was doing well, and Billy bought a Ford Model T.

Billy was drafted for World War I in 1917, but during his medical exam, the doctor left the room to take a call, leaving behind Billy’s personnel record. Billy swiped it and bolted. With no record of him ever being in the Army, he never reported for service. When the 1918 influenza pandemic struck, it decimated the nickelodeon’s business. Billy quit and started working for Universal Studios delivering movies to nickelodeons. He was promoted to district manager of film distribution in Kansas City. Helen stayed in New York and Billy split his time between the two cities. In 1920, Billy returned to find Helen had left him for another man. After eight years of marriage, Billy was devastated. In 1921 he quit his job and traveled Europe to escape his grief. In 1922, he started working for what would later become Paramount Pictures as a film salesman. This job sent him on sales trips to Hollywood, where he saw the early beginnings of the film industry’s migration from New York City to this new location.

Billy was restless by the end of 1923. In 1924 he held several jobs in the industry, and in 1925 he started selling ads and writing for Film Daily, the main motion picture trade paper. The owner was a tyrant, and Billy missed being his own boss and keeping some of the profits he generated. He wanted to own a film studio, so in 1926 he took a train to Hollywood. Using a fake-it-till-you-make-it approach, Billy convinced popular actor/comedian El Brendel to star in the movie he and his friend Joe Pasternak would produce. Billy shopped the film to studios in New York, but they were controlled by autocratic moguls who “rivaled robber barons.” Billy failed to convince the studios. Wilkerson Studios never got off the ground.

To make money, Billy opened a speakeasy in November 1926 to fill a gap he saw in the Prohibition-era market. His operation was high class but illegal. By February 1927, he opened a second one and charged a $1,500-per-person initiation fee. He paid off police and DAs and worked with the mafia and Joe Kennedy to get his liquor supply. He did such a great job that James Walker, mayor of New York City, asked Billy to manage his speakeasies for 45% of the profits. Billy was making $1 million per year, although he lost much of that in the backroom card games he hosted. He also started dating Edith Goldenhorn, the 25-year-old daughter of his ethically challenged lawyer. Billy, then 35, married Edith in Las Vegas in June 1927. When he returned, his speakeasies were raided, which spooked him. He immediately quit the speakeasy business for good.

Billy was still resentful about his film and believed Jewish studio heads didn’t give him a chance because he wasn’t Jewish. He took the rejection personally and wanted revenge. His time at Film Daily taught him that trade papers could be powerful, and he decided to start the first daily trade paper for the Hollywood motion picture industry. In February 1929, he acquired 50% of a faltering Manhattan trade paper. He turned it around and sold the paper seven months later, pocketing $20,000. He borrowed $25,000 from a loan shark and bet the combined $45,000 on a single company in the stock market. It was October 29, 1929, better known as Black Monday. Forty-five minutes after his purchase, the market crashed. Billy was wiped out. Unable to pay the loan shark, Billy, Edith, and Billy’s mother Mary drove cross-country to start over in Hollywood.

Little did Billy know that his decision to start a trade publication in Hollywood would change his life and the movie industry forever.

I finished reading about Robert Edward “Ted” Turner III’s journey. His autobiography details his life through 2009, when he was about 71. Today Turner is 85 and lives a less public live.

How Did Turner’s Early Years Impact His Journey?

Turner’s father had an outsize impact on him and was the reason he became an entrepreneur. His father was a complicated man. He instilled a strong work ethic in his son at an early age. He openly shared with Ted the wisdom he’d gained building his billboard business, and he gave Ted the opportunity to learn lessons by leading a division within his company. However, he was also controlling, an alcoholic, and a womanizer. He physically beat, psychologically manipulated, and rarely praised his son. His suicide shattered Turner’s world and left a void that would never be filled.

The McCallie School, then a Christian military academy, had a positive impact on Turner and turned him into a leader. The structured environment was different than his unstable upbringing and one that he thrived in. It allowed him to channel his high energy and work ethic toward positive outcomes. As he succeeded and led others, he received positive reinforcement, which made him strive for more achievement. His desire to excel and be noticed drove him to join the debate team, where he developed analytical and persuasion skills that were critical to navigating problems as an entrepreneur.

How Did Turner Become So Successful?

Turner inherited a sizable business from his father, so he avoided the challenging start-up period during which many businesses fail. Instead, he was able to focus on building on his father's success. Turner inherited this company when he was just 25. Considering that runway length is one of the most important inputs in the compounding formula, his inheritance at an early age positioned him well for outsize success.

Turner quickly understood the impact that new technology would have on his ability to grow his business rapidly. Turner realized that billboard advertising was no longer a growth business and shifted to television advertising. This led to his owning a television station, which led to his discovery of cable TV and satellite distribution. He understood that cable was growing rapidly and that as more houses were wired for cable, subscriber fees from cable operators would grow rapidly while his costs stayed relatively flat. Cable distribution was an amazing form of leverage to create a rapidly growing and highly profitable business.

Turner understood the value of good content and how to maximize its value creation. He bought libraries of movies and cartoons that weren’t being used. He knew he could create cable channels dedicated to these content genres and distribute them to millions of households via cable TV. He could pay more than rival bidders for these libraries because he had the know-how and distribution means to maximize their value.

Turner was a master at using stock-based deals to grow his business and his wealth. He used his company stock to acquire companies when he could, which preserved cash and reduced the debt required to close deals. It also aligned his interests with the owner of the company he was acquiring. When he sold Turner Broadcasting, he didn’t sell for cash. He was compensated in Time Warner stock. He didn’t have to pay taxes on the sale and was able to continue compounding his wealth through significant ownership of Timer Warner shares.

What Kind of Entrepreneur Was Turner?

Turner preferred to buy businesses rather than build them from scratch. He had some founder traits and was gifted at launching new channels, but that’s different than launching new companies. He did more buying of existing businesses than starting them from zero. The foundation of Turner Broadcasting was a company he inherited from his father, and he continually built on this foundation through acquisitions.

Turner was a visionary entrepreneur. He was not operationally gifted or detail oriented. He focused on identifying growth opportunities and left the details of execution and managing day-to-day operations to his managers.  

What Did I Learn from Turner’s Journey?

Turner’s journey taught me that you can maximize the value of evergreen content by repackaging and distributing it differently. Turner created immense value from decades-old movies and cartoons by repackaging them as part of channels focused on those types of content. He also was able to get the content to consumers who otherwise wouldn’t have access to it by distributing it via cable TV. The content was old, but it was new to viewers of his channels, and it helped those channels generate high ratings.

Turner is an amazing entrepreneur and an Atlanta legend. His autobiography describes a life of extreme highs and extreme lows. Anyone interested in learning more about him will benefit from reading this book.

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In 1995, Robert Edward “Ted” Turner III sold his company in a $8 billion deal with Time Warner. After almost twenty years of ownership, his Atlanta Braves won the World Series. And his marriage with Jane Fonda was the “most intense and fulfilling” of all his marriages. Turner was riding high.

According to his autobiography, Turner began adjusting to being an executive at Time Warner. The extravagant sums spent at headquarters while post-merger cuts were being made bothered Turner. The culture was also different. Turner Broadcasting’s strength came from the division heads working together toward the parent’s goals. Timer Warner was a series of fiefdoms that didn’t work together. Turner and Time Warner CEO Jerry Levin worked well together, but they never became friends and didn’t socialize outside work. Regardless, the business was doing well, and by 1997, Ted’s Time Warner stock holdings were worth $3.2 billion.

Part of the reason Time Warner was growing wasn’t obvious at first. But eventually Turner noticed that “dot-coms” were showing up frequently in his sales reports for the cable networks he managed. Start-ups had raised tons of money and spent it with traditional media companies like Time Warner to acquire customers. Turner realized the internet craze was boosting their ad sales.

Time Warner’s business was doing well, but public market investors perceived it as an “old media” company. As a result, they sold Time Warner stock to buy dot-com stocks. Jerry Levine felt pressure from financial media and analysts to do more on the internet to lift the company’s stock price, so he rushed to develop a digital strategy. Around this time, Ted and Jane started having difficulty communicating and started attending counseling sessions as a couple and individually.

AOL founder Steve Case and Jerry Levine met in fall 1999 and began discussing working together. At the time, Time Warner had revenue five times greater than AOL’s, but AOL’s stock market value was twice as large. Then on Friday, January 7, 2000, Levine called Turner and told him they were merging with AOL. The news shocked Turner, who wasn’t aware a deal was in the works.

Ted had a few days to decide whether to vote in favor of the deal at an emergency board meeting and whether to vote his 100 million shares in favor of the deal. He was asked to sign an irrevocable agreement that prevented him from selling shares before the deal closed, which was estimated to take a year. Turner supported the deal, and the $160 billion deal caused a media frenzy when it was announced the following Monday. Time Warner’s stock rose 40% that day, and Turner was worth $10 billion.

A few months later, things took a turn. The stock market tanked and the NASDAQ Composite Index lost a third of its value in a three-week period. AOL’s stock dropped, which made the all-stock deal less appealing. The dot-com crash had begun, and Turner knew AOL wasn’t worth what people thought, but he had no power to protect himself or do anything about it. To make matters worse, Levine informed Turner that post-merger, he would have no responsibilities and no direct reports but would continue receiving his salary. Ted felt that he was being fired. In January 2001, regulators approved the deal to close.

This was a period of extreme difficulty for Turner. He’d lost his job and his wife. His fortune was steadily declining, and insider trading laws prevented him from selling any of his shares. To make matters worse, his two-year-old granddaughter died from a rare genetic disorder. The weight of this all caused severe anxiety, and Turner couldn’t sleep.

Things went from bad to worse. The September 11, 2001, terrorist attacks drove the stock market down further and slowed the economy. Jerry Levine and Steve Case were forced to acknowledge to Wall Street that AOL Time Warner would not meet its lofty projections. The stock, which had tanked to $40 months earlier, dropped to $30. Ted’s frustration spilled over, and he pushed Jerry Levine to step down as CEO, which he did in December 2001.

In April 2002, the stock dropped below $20. Ted couldn’t take it anymore and sold $190 million in shares at $18.50 to pay off his bank debt. In July 2002, the stock fell to $13, and then the bottom dropped out when the Washington Post ran a story about accounting irregularities at AOL. The SEC opened an investigation, and the stock dropped to below $9. Turner was in shock. Over two-and-a-half years, Turner’s net worth went from $10 billion to $2 billion. He’d lost $8 billion in 30 months, which was equivalent to losing $10 million every day for two-and-a-half years.

Ted, enraged, forced Steve Case to resign as chairman of the board of directors, which he did in January 2003. In February, Ted resigned as vice chairman of the board. The company was laying off people and selling assets to stabilize itself. Ted found this painful to be part of, and he continued selling his shares. By May 2003, he’d reduced his ownership from 100 million to 7 million shares. That year, he decided not to stand for reelection to the board of directors, and in August 2003, he sold his remaining 7 million shares for $16 each.

The AOL and Time Warner ordeal was extremely stressful for Ted and gave him bouts of anxiety and frustration, but it didn’t stop him. He left the company he’d been with for fifty years, but he was still full of energy that he wanted to put to good use.  

Ted Turner is a remarkable entrepreneur with a colorful personality. His journey was inspirational—he was an outsider entrepreneur who not only thrived but built a massive company. Turner isn’t perfect, and his journey is also full of cautionary tales. Anyone interested in learning more about media, sailing, owning sports teams, ranching, or growth through acquisition will likely enjoy his autobiography.

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In the early 1980s, Robert Edward “Ted” Turner III was worried that Hollywood movie studios would hike prices beyond what he could afford and cut off content that his audience valued. Merging with a movie studio would ensure a steady supply of movies. Kirk Kerkorian owned 50% of MGM/UA, and in July 1985, he told Ted he was selling everything except United Artists (UA) for $1.5 billion in an auction the following month. He invited Turner to purchase the assets before the auction.

In August 1985, Turner and Kerkorian struck a deal. Turner Broadcasting would acquire MGM/UA for $1.4 billion and Turner would immediately sell UA back to Kerkorian for $480 million, resulting in a net purchase price of just below $1 billion. Turner would also have to assume $700 million of MGM’s existing debt, which meant a total price tag of $1.6 billion. To close the deal in March 1986, Micheal Milken of Drexel Burnham helped Turner reduce the cash portion of his bid. He issued high-yield junk bonds. He also issued new preferred stock in Turner Broadcasting to Kerkorian. Deal terms gave Turner nine months to pay off $600 million in junk bond debt, and he had to pay Kerkorian a dividend on his preferred shares.

According to his autobiography, Ted realized that asset sales wouldn’t be enough to cover his $600 million obligation—he needed to refinance his debt. He went to John Malone of TCI and other cable operators for help. By June 1987, a deal was in place for Turner to raise $565 million from thirty-plus cable operators in exchange for the group owning 37% of Turner Broadcasting. Ted kept majority ownership, but the deal had other strings attached.

Ted’s autonomy was reduced, and his biggest customers, cable operators, were now on his board of directors and had input into his company strategy.

After he refinanced his debt, Turner launched a new channel that would show original movies and high-profile events such as the Emmys and the Miss America pageant. The new channel was called Turner Network Television (TNT) and would generate revenue from advertising and a subscription fee, paid by cable operators, of $0.15 per cable subscriber per month. TNT launched in October 1988 with 17 million households, and by its first anniversary it was in 50 million households and generating almost $100 million in subscriber revenue alone. By 1989, Ted was about 51 years old and his ownership in Turner Broadcasting Systems was worth over $1 billion.

Professionally, things were going well for Turner, but personally, things weren’t as smooth. By the end of 1988, he and Janie had divorced after more than twenty years of marriage. Ted was diagnosed with bipolar depression. He aggressively pursued Jane Fonda after reading about her divorce in the newspaper, and the two married in 1991.

Operation Desert Storm in early 1991 put CNN on the map. It was the first time a war was reported on from behind the lines live on TV. Ratings skyrocketed. Turner’s strategy was now clear: own as much programming as possible and air it on networks he owned and controlled. Content was the key to great programming. In 1991 he bought Hanna-Barbera Studios, creator of Scooby Doo and the Jetsons, for $312 million. Combining it with MGM’s cartoon library, he owned two-thirds of all cartoons ever made. He then launched a twenty-four-hour-a-day cartoon channel and named it Cartoon Network.

Turner was still worried about movie content. He had a library of old movies, but he was worried about being cut off from new movies by Hollywood studios. Because of the board-control issue, he couldn’t buy Paramount, so he purchased Castle Rock Entertainment and New Line Cinema for $600 million in the summer of 1993. He also maximized the value of his older movies by launching a new channel, Turner Classic Movies, in April 1994.

Turner believed that vertical integration was the key to long-term success in his industry. Owning a broadcast network and movie studio was the best way to create, distribute, and monetize proprietary content. He continued to pursue merging with a broadcaster, but his desire to own a movie studio killed a potential deal to merge with ABC’s owner, Capital Cities, because major shareholder Warren Buffet disliked the movie business. Turner even started talking to Bill Gates about getting a $1 billion investment to make a bid for CBS and came close to becoming a 50/50 partner with Gates.

In 1995, the company was doing well. It had gone from $1 billion in revenues to $3.5 billion in just six years. But Ted was frustrated with the board of directors’ veto ability, specifically the board member representing Time Warner. It limited his ability to acquire a broadcast network. He went public with his frustration and started discussing buying Time Warner’s position back at a premium. Around this time, Ted began to rethink not wanting to own a cable system. Because so many channels were launching, and FCC rules were changing, it now made sense. The board of Time Warner, which owned a cable system, was also rethinking its position and decided that owning Turner Broadcasting would provide synergies and could lift its sagging stock price. A deal was struck, and in September 1995, it was announced that Turner Broadcasting was acquired at a value of more than $8 billion in a stock deal. Turner would no longer be CEO and would have a boss. This decision would set Turner up for an epic ascent of his wealth and a terrifying crash that he had no control over.

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When Robert Edward “Ted” Turner III launched Cable News Network (CNN), he was taking a financial risk. According to his autobiography, he didn’t have enough capital to fund the channel until it reached breakeven. He saw two potential outcomes: The value of the channel would become clear, and raising capital would become easier. Or he’d built a channel valuable enough to be acquired. Both were acceptable, so he plowed ahead.

The CNN launch almost gave Turner a nervous breakdown. It launched on time but was a financial disaster. Expenses were twice the budget and revenues were half the budget. Turner was losing four times more than he projected. To make matters worse, ABC and Westinghouse, two multibillion-dollar companies, were teaming up to launch a CNN competitor, Satellite News Channel. They planned to offer the new channel to cable companies for free alongside a short news channel they would also create.

Ted went to war. He created an “all-news channel with a thirty-minute cycle of headline news.” He called the new channel CNN2 and aimed to beat his competition to market in 1982 by six months. He couldn’t afford space on a satellite for CNN2, but he found a solution. Warner Communications wasn’t using its leased satellite space. Turner took Warner’s space and paid for it by allowing Warner to take over all ad sales for Turner Broadcasting and collect a royalty on all ad revenue it generated. It was a risky deal because it meant losing control of his sales operation, but Turner had no choice. He took it further and offered cable operators a 70% yearly discount on CNN subscription fees for three years if they carried CNN and CNN2. He even filed a $300 million antitrust lawsuit against ABC and Westinghouse.

Turner’s strategy worked, but it was costly. ABC and Westinghouse agreed to discontinue their channel if Turner paid them $25 million and dropped his lawsuit. His warfare strategy was costing him $4 million a month, so $25 million, while steep, was cheaper than a prolonged war.

By 1984, CNN, Headline News, and SuperStation were growing, but Turner Broadcasting was too small to compete against the big three broadcast networks for audience and advertising dollars. Turner’s company was generating $280 million in revenue and $10 million in profit. CBS alone was generating $5 billion in revenue. Turner decided that merging with one of the big three was his best option.

But merger conversations with the networks went nowhere. At the time, unfriendly corporate takeovers by raiders were popular. Turner got close to T. Boone Pickens, a famous corporate raider, and learned how that game worked. He then partnered with Michael Milken of Drexel Burnham to issue junk bonds and, in 1985, made an unsolicited offer to take over CBS. CBS fought the effort vigorously and the takeover died. But the publicity from this attempt led to Kirk Kerkorian calling Turner with another offer.

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After his father’s suicide, Robert Edward “Ted” Turner III was CEO of Turner Advertising Company, which he had saved. According to his autobiography, his work life was improving, but his personal life was hectic. His son Teddy was born in March 1963, three months after his father’s death. And by the end of that year, he was getting divorced and Judy had moved with the children to Chicago to be near family. Turner was 25 years old and a divorced father of two. In 1964, he met Jane Smith and married her in less than a year. Shortly thereafter, his son Rhett was born.

Ted wanted to expand. He acquired a Chattanooga, Tennessee, billboard company for $1 million and a Knoxville, Tennessee, billboard company at an estate auction for $53,000. Shortly after these deals, the outdoor advertising business began looking less attractive to Turner because of proposed legislation and advertisers’ exploration of television. Television’s future looked bright, and Turner decided to model his company after Combined Communication, which Karl Eller expanded from a billboard company to include radio and television. Ted bought radio stations in Florida and South Carolina, but he decided he didn’t like the radio business.

By the late 1960s, Turner set his sights on Channel 17, eventually known as WTCG, a financially struggling UHF television station in Atlanta. The owner wanted $2.5 million. Turner didn’t have cash, so he merged with the station. He retained 47% ownership and changed the company name to Turner Communications Group. Turner also bought a bankrupt Charlotte, North Carolina, station, WRET, for less than $1 million; he did this investment personally. The stations were a financial drain. Low on cash, unable to pay suppliers, and at risk of going off the air, Turner did an on-air telethon to raise money. He raised $25,000 and generated goodwill in the community.

Ted recognized that programming should be his focus because it attracted viewers, which led to more revenue from advertisers. His strategy was to find areas where competitors weren’t meeting viewers’ needs and fill those gaps. He paid $600,000 to air sixty Atlanta Braves baseball games a year and went on to cut deals to air Atlanta Hawks basketball games and Atlanta Flames hockey games. His strategy worked: WTGC went from $900,000 in losses in 1970 to $1 million in profit in 1973.

The Braves ownership, losing $1 million a year, offered Turner the chance to purchase the team for $10 million, which he did in 1976. This gave him control of long-term TV rights and guaranteed unique programming.

Turner was still focused on growing his TV stations. This required growing viewers, but there weren’t unlimited viewers in Atlanta. He needed to gain viewers in other markets. He kept hearing about “community antenna television,” so he investigated it. This new technology, better known as cable TV, allowed him to access views in other markets. He learned through trial and error that satellites were the key and built the first satellite uplink station in Atlanta. He changed his company name to Turner Broadcasting System Inc. (TBS) and changed the Atlanta TV station name to SuperStation. The first satellite transmission occurred in December 1976.

With TBS distributed by satellite throughout the southeast, Turner recognized he was sitting on a gold mine. Cable was growing rapidly. As cable operators expanded their coverage areas, they added subscribers. As they added more subscribers, the per-subscriber fees they paid increased, which meant more revenue—but few or no incremental costs—for TBS. Programming (i.e., unique content) was the key to capitalizing on this gold mine and growing revenues and profits rapidly.

Tuner saw news as great content, but it was delivered at times that weren’t convenient for everyone. Turner decided to start a twenty-four-hour-a-day news channel to fill this gap and named it Cable News Network, or CNN. He decided to launch on June 1, 1980. This decision would change his trajectory forever.

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Robert Edward “Ted” Turner III is an entrepreneur known for the Turner Broadcasting System, which birthed the CNN, TBS, and TNT cable channels. Everyone in Atlanta knows of Turner, but I decided to buy his autobiography, Call Me Ted, after reading about his financing deal for MGM/UA in the biography of Kirk Kerkorian.

Turner was born in 1938 in Cincinnati, Ohio. He was sent to boarding school when he was four years old, when his father joined the Navy and his younger sister Mary Jean and mother joined his father on base. Ted’s father was a complicated man. He moved the family to Savannah, Georgia, when he acquired a small billboard company in 1947. He enrolled Ted in The McCallie School, then a Christian military academy in Tennessee. At age twelve, Ted began working 42-and-a-half hours a week at his father’s company in the summers, usually doing manual labor with outside crews.

Growing up in Savannah, Turner learned to sail by joining his dad on sailing trips. His love for sailing was the deciding factor in attending Brown University, which is located on Narragansett Bay in Providence, Rhode Island. After his freshman year, his parents divorced, and his mother and sister moved back to Cincinnati. After Turner lost a bet and failed to honor a commitment to his father, his father stopped giving him a weekly $5 allowance. Frustrated about the situation with his father, he fell in with the wrong crowd and got suspended for the rest of the school year. To fill his time, he joined the Coast Guard as a reservist until he could return to Brown the following semester. Then, after declaring classics as his major, Ted had a nasty falling out with his father, who refused to pay his tuition any longer. He was forced to leave Brown.

Turner briefly moved to the Miami area but was broke, so he started working for his dad’s company, Turner Advertising Company, in 1959. At 21, Turner married Judy Nye, a fellow sailing enthusiast he’d dated long distance. A few months later, his sister Mary Jean died; she was just 17.

Turner moved to Macon, Georgia, with his new bride to take over a small billboard company his dad had acquired. At just 21, Turner ran the company, and within two years he’d doubled its revenue. His marriage with Judy was rocky, but they welcomed a daughter, Laura, in 1961.

In 1962, Ted’s father made a deal with an entrepreneur from Minnesota to purchase General Outdoor Inc., a larger billboard company based in Atlanta. The $4 million deal was financed with debt, and Ted’s father split the acquired assets with the other entrepreneur. Ted moved to Atlanta to help run the leasing department of the acquired company; his family stayed in Macon.

After closing the deal, the fear of losing everything because of the debt load consumed the elder Turner. His behavior became erratic, and he checked into rehab. One day he announced he was selling a big part of the company to the Minnesota billboard entrepreneur, which shocked Ted because it had only been a few months since the closing. A few days later, in March 1963, the elder Turner committed suicide.

Ted was in shock, but he had to pick up the pieces. He was the executor of his father’s estate. The deal to sell General Outdoors assets was signed the day before his father died. It was an informal handwritten note, but it was binding. Turner started renewing billboard leases with General Outdoors customers in the name of his Macon company, which reduced the value of General Outdoor assets being acquired. The buyer was angry and offered to pay $200,000 to have all leases returned, or Turner could pay him $200,000 to retain all the General Outdoor assets. Turner picked the latter but didn’t cash; he paid using his company stock. Cash was still an issue because the $600,000 first payment on the General Outdoors debt was coming due. Turner went into fire-sale mode and sold his father’s 1,000-acre plantation and commercial real estate to raise the funds. He kept his father’s company intact.

Turner was now ready to start rebuilding his family’s empire, but first he’d have to resolve his personal troubles.

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I finished reading more about Felix Dennis. The first book I read about him, which he wrote, detailed his thoughts on how to succeed as an entrepreneur. The second, a biography, described his journey from his early years through his passing at age 67 in 2014. The latter book contained less detail about Felix’s entrepreneurial journey than I’d hoped, but I still learned some new things about him.

How Did Dennis’s Early Years Affect His Trajectory?

His parents’ dynamic had a big impact on Dennis. His father leaving when Dennis was four put pressure on his mother to provide for her sons. Working as a bookkeeper, she realized a career in accounting could be her savior. She became laser-focused on becoming an accountant so she could provide. The positive was that Dennis saw work ethic and focus pay off for his mother. But her sons were neglected and didn’t get much, or any, motherly warmth from her. Felix followed in his mother’s footsteps: he was laser-focused on his goals and outworked everyone else to make them happen.

His parents struggled to keep their general store open, and his mother struggled as the sole provider. There wasn’t a lot of money, and at one point, Dennis’s living arrangements included an outside toilet and no electricity. Dennis was determined never to live like that again. “Under no circumstances would I stay poor,” he wrote. His determination fueled his pursuit of financial freedom.

Felix was in his early twenties when the Oz trial ordeal began. It was a rude awakening to how the world really works and how unfairly the establishment treats certain people. He decided he needed money to put himself on a fairer playing field with the establishment and to make it possible to defend himself if necessary. This realization about money was another factor that fueled his pursuit of financial freedom.

How Did Dennis Become So Successful?

The Oz trial had a significant impact on British society. It made Dennis an icon and gave him an edge, especially in the publishing world. This standing opened doors for him and allowed him to make several critical deals. His name alone would get him meetings with people or allow him to steal deals that competitors considered won but that weren’t closed.

Dennis was a master at identifying market gaps and filling them with something people would love. He was highly gifted at being in tune with what people wanted. He had a deep understanding of how customers thought and how to create publications that resonated with them. He was what the venture capital world would call a hipster and played this role repeatedly, especially in his partnership with Peter Godfrey and Bob Bartner. Maxim's outsize international success was a result of Dennis’s hipster abilities.

Felix was also an unapologetic opportunist who had a keen sense for markets that were severely underserved or would be underserved because they would grow rapidly.

Another contributor to his success was that he didn’t have a wife or children, so he could work longer hours and take bigger risks without worrying about the impact on his family.

Dennis was gifted with words. He knew how to talk to people in a way that resonated deeply with them. He made everyone he conversed with feel like they were the only thing that mattered. He mesmerized people when he spoke with them. This made him a superior salesman who could close almost any business deal. It also made him a gifted poet and womanizer.

What Kind of Entrepreneur Was Dennis?

Dennis was a founder. Most of the businesses he was involved in started from nothing. As his empire and resources grew, he bought some publications, too.

Dennis believed that making money was a skill. He applied it to publishing, but he believed he could have applied it to any industry and done well. His confidence in his moneymaking skill led him to take risks that others wouldn’t dare take.

Dennis was also a marketing genius. He instinctively knew how to get and keep people’s attention. This served him well in publishing because attention was what he sold to advertisers.

Dennis was a colorful entrepreneur who changed publishing in the UK and the United States. I’m still curious about some aspects of his journey and will be reading more about him.

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In 1994, Jolyon Connell recognized that newspapers were bigger but people were busier, so they had less time to read them. He created a weekly digest magazine, The Week, to solve this problem. When Felix Dennis heard about the magazine, he invested. Within a year, he had 51% ownership. According to the biography about Dennis, he saw the magazine’s potential and had the resources at Dennis Publishing to take it to the next level. Realizing “the reader was king,” he focused on building a solid subscription base by adding value for readers. It worked, and the U.S. version launched in 2001. The Week was on a par with Newsweek and Time magazines and gained Dennis a level of respect from other publishers, which had avoided him before.

In 1995, Dennis Publishing launched Maxim magazine. The secret to its breakout success was a gap in the market. No one was publishing magazines for young men, ages 18 to 34, as they were for young women. Women’s magazines were more general. Magazines targeting men were specialized. Young men interested in science or physical fitness also “watched sport[s], talked about girls, and ate chicken wings.” Maxim filled this void by appealing to the universal interests of all men in a bold way. It sold 350,000 copies in the UK when it launched.

In 1997, Maxim U.S. was launched by Dennis and his two U.S. partners, Peter Godfrey and Bob Bartner. Creative marketing became a key to U.S. success. Maxim became known for throwing unbelievable parties, which gained celebrity attention and made attractive female celebrities inclined to pose on the magazine’s cover. It also creatively engineered getting promotion from Howard Stern, whose radio show was one of the most popular in the nation. Maxim was a gigantic success in the U.S. and sold 1.2 million copies per issue—10 or 20 times more than rivals like GQ and Esquire. At one point, Maxim U.S.’s ad rates rivaled TV ad rates. Maxim gained a cult following because, as Dennis put it, “it was the first beer truck to reach the desert.” Maxim positioned itself as the best conduit to connect advertisers with a large audience in this hard-to-penetrate demographic.

In 2007, Maxim was wildly successful in various countries when Dennis Publishing sold Maxim, Blender, and Stuff magazines to private equity firm Quadrangle Capital Partners, netting $240 million.

Flush with cash, Felix started to lean more into a passion he'd be developing for almost a decade, poetry. He bought a home on Mustique Island in the Caribbean and spent most of his time there, writing poetry. He published books of poetry and even went on tours reading his poetry in the U.S. and UK. Then, in 2011, Felix began to have health issues. First it was throat cancer, which shocked him. He was lucky; he survived after successful neck and mouth surgery. He eagerly resumed his poetry tours when, in 2013, he was diagnosed with terminal lung cancer. That diagnosis was devastating, and Felix decided to spend his remaining time mostly alone. On Sunday, June 22, 2014, Felix passed away.

Dennis was a pirate and maverick who happened to also be an entrepreneur. He enjoyed going against the establishment and shaking things up. He forced his way into what was then a stuffy industry and left a lasting impression on it. His outsize success forced his peers to respect him and change how they thought about the publishing business. Dennis’s track record of success over decades was undeniable, and many of the publications he started still exist today. But for all his success in publishing, his true passion ended up being writing and sharing his poetry. Building a publishing empire was a means to that end for Dennis.

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Felix Dennis began to hit his stride after selling MacUser magazine in 1986. According to the biography of his life, he’d landed on a strategy: creating magazines in growing markets, building them up, and selling them to larger publishing houses. That strategy helped him build his initial capital base, but it was about to change.

When MacUser was sold, Dennis and his partners realized that the biggest ad source was computer component sellers. Ads were driving massive revenue for those sellers, they discovered. The trio decided to launch Micro Warehouse as a mail-order company selling computer parts. It helped that they’d managed to secure 24 pages of free advertising as part of the MacUser sale.

The trio landed on two magic ingredients. They used sales to individual users of Mac computers inside corporations as a trojan horse to eventually sell parts to PC users (a much bigger market) in those organizations, too. And they offered $3 overnight shipping to build trust with corporations that weren’t yet comfortable with mail order. These ingredients, along with Dennis creating an attractive catalog, quickly produced $500 million in annual revenue. When the company held its IPO in 1992, it was receiving ten thousand calls from customers daily. The IPO was a huge financial success for Dennis and his partners.

During this period, Felix launched and acquired several other publications and renamed his firm Dennis Publishing. But he was also dealing with personal demons. He began to hire prostitutes to feed his sex addiction. He also developed an addiction to crack cocaine. These problems and a grueling work schedule led to Dennis being hospitalized and almost dying at age 41. This near-death experience, combined with financial freedom and other factors, would lead to Dennis discovering his true passion and next career.

Prefer listening? Catch audio versions of these blog posts, with more context added, on Apple Podcasts here or Spotify here!