After his separation from Jack Kent Cooke, Roy Thomson kept moving forward. He continued to try to pierce the upper echelons of Canadian society by joining the board of the prestigious Albany Club in Toronto. According to his biography, he bought three more Canadian newspapers and issued $3 million in bonds to finance these and other purchases. He hired a right-hand man with an encyclopedic knowledge of Canadian newspaper statistics who improved his sourcing of newspapers to purchase. He was well on his way to achieving his publicly stated goal of owning 52 papers, one for each week of the year. Everything was trending upward until his wife, Edna, was diagnosed with cancer in 1951 and passed away in 1952. After she passed, Roy regretted working so much and not spending more time at home with her.

As a widower, Roy did what he knew best: he dove into his work and his presidency at Canadian Press, a trade association. As president, Roy preached to publishers that broadcasting wouldn’t kill newspapers, technology was expensive up front but cheap in the long run, and television shouldn’t be feared because television and radio stations could buy news from Canadian Press. Roy also bought seven more Canadian newspapers during his tenure as president and a Florida newspaper while vacationing in the state.

Continuing to try to grow his networks and influence in the upper echelons, Roy ran for Parliament of Canada as a progressive conservative candidate. He was defeated. Undeterred, he refocused on his business and decided to expand into Great Britain. In 1953, he began printing a weekly magazine for Canadians living in Britain. Then The Scotsman, a prestigious newspaper in Scotland, asked Roy if he was still interested in buying it. The newspaper had been mismanaged after the World War II boom and was losing money. To transfer ownership to the next generation, its owner would face a death tax it couldn’t afford. Roy bought The Scotsman and two sister papers. The deal stipulated that he become a resident publisher. At 59, he moved to Edinburgh, Scotland, to build another empire.

Roy transferred management of his North American and Caribbean businesses to his son Kenneth and executives. He focused intensely on turning around The Scotsman, but things didn’t go as planned. Roy cycled through a few editors, and circulation dropped. Edinburgh’s high society, which initially wanted to get to know Roy, shunned him because of his blunt demeanor and changes he made to their local newspapers. Unsure how to turn things around, Roy offered Jack 25% ownership for free if he’d move to Edinburgh to run the newspapers. Jack, successful in his own right, declined.

Things were going well in Canada. His team was steadily buying newspapers in Canada and Florida. They even acquired two television stations in partnership with a local senator. But it would be three years before Roy’s Edinburgh newspapers stopped losing money, which happened in 1955. Even with this significant turnaround complete, Roy was not content; he was back in grow-my-empire mode and considering how to start Scotland’s first independent television station.

November 1936 changed Roy Thomson’s business life. According to his biography, that’s the month when Jack Kent Cooke, a 24-year-old traveling salesman, asked for a job at Roy’s radio station CJKL. Roy was having problems with a newly acquired station, CJCS, in Stratford, Ontario, and hired Jack to turn the station around. Within six months, the station was profitable, and Roy decided to sell it for $10,000 for a profit of $6,000. Roy became fond of Jack and hired him to oversee sales in a newly created Toronto office.

Jack’s superior sales skills took that responsibility off Roy’s plate. He spent more time “figuring,” as he called it. In 1938, Roy convinced Jack to move to Timmins to manage all aspects of all five radio stations. Everything was going well until a fire in April 1939 burned down the building that housed station CKGB and the Press newspaper in Timmins. Roy was underinsured, but he bounced back. He borrowed to build a building for both his companies.

The world was on the cusp of World War II, and rumors circulated that paper would be rationed and sent to the United States. Roy figured this would lead to more advertising dollars flowing to radio, especially since more people were listening to their radios to receive war news. Not wanting to share the profits he envisioned his stations would produce in 1940, he bought back as much of his company stock as he could.

By 1940, the radio stations were running smoothly under Jack’s management. As Roy had predicted, the war was good for his radio business. Jack also found reinvestment opportunities for the profits that Northern Broadcasting and Publishing was generating. He and Roy partnered to buy their first French-language radio station in Quebec for $21,000. Two other purchases followed. Roy owned 66% of the partnership, and Jack owned 33%.

Roy and Jack expanded their radio empire by agreeing to manage Ontario radio stations owned by a senator. This capital-light approach gave the two partners 49% ownership in them.

The war, after it began, became a massive tailwind for Roy’s newspaper, too. Paper rationing made advertisers buy space in smaller rural papers, like the Press, because papers in big cities like Toronto were limited in pages and ad space.

The war had put Roy’s empire on solid financial ground for the first time. The depression years had conditioned Roy to keep salaries and expenses within budget, which boosted his profitability when wartime ad revenue surged. Roy standardized his accounting, making comparing the performance of his stations, apples to apples, easy.

Eager to reinvest profits, Roy upgraded his stations, paid off bank debt, and bought back outstanding stock in his company from outsiders. In 1943, Roy spent $880,000 to buy four newspapers with a $375,00 bank loan; the rest was seller financed. He owned eight radio stations and five newspapers after that deal closed. He and Jack agreed to a partnership in which they shared in each other’s deals; Roy got 66% and Jack 33%. The two started sourcing deals independently and evaluating and investing as a team.

Jack, eager to do more radio deals, found a Toronto radio station he could buy for $500,000. He didn’t have the money, so he convinced Roy to sell their Quebec stations. When those stations were sold, Jack's share of the proceeds provided him with capital he used to complete the purchase of the Toronto station. Roy declined to be part of the deal to buy the Toronto station, but within a few months, Jack had turned the station from unprofitable to solidly profitable. Jack became known as a radio station entrepreneur.  

Roy bought two more newspapers in small towns for $750,000 and realized there was a big opportunity to purchase more small-town newspapers. Families had owned them for generations, had underinvested in them, and had to pay inheritance tax each time the ownership transferred to the next generation. Roy worked with investment bankers and issued $1,000,000 in bonds so he could go on a buying spree. Roy’s economic blueprint for buying and running rural newspapers would make him the millionaire he’d dreamed of being years earlier.

After Jack successfully managed the Ontario radio station for the senator, ran Roy’s stations, and turned around his Toronto station, a prominent media family approached him. They offered him a massive contract to manage their Ottawa radio station. On one condition: Roy could not be part of the deal. Jack accepted, and when he told Roy he wasn’t part of the deal, it was the end of their decade-plus friendship and partnership. Feeling betrayed and cut out by his young protegee, Roy started seeing Jack as a rival. The two divested themselves of ownership in each other’s companies and went their separate ways. Jack would later call that deal “one of the great mistakes in my life.”

With a thriving empire, Roy would soon begin to set his sights on taking his empire international.

According to the biography about him, Roy Thomson was determined to learn how to start a radio station. He tracked down the company that owned the license to broadcast in his area and struck a deal to acquire the license for $1. He struck another deal to set up his station in a building owned by a theatre company, paying in advertising time, not dollars. Station CFCH went live in March 1931.

Roy had solved his problem. Radio orders began rolling in. But he needed cash to pay for radios he’d gotten from the manufacturer on consignment. He landed a big contract with a large store in a rural community and leveraged that purchase order to borrow enough money to pay the manufacturer. Roy narrowly avoided bankruptcy.

Things remained tight for a few years, to the point that Roy’s employees knew they couldn’t immediately deposit their paychecks. Despite the shaky ground his business was on, Roy was elected North Bay alderman in 1931 and lost a bid to become mayor of North Bay in 1932. He then refocused his energies on expanding his business and eyed Timmins and Kirkland Lake, both in Ontario, as promising cities. Roy borrowed money from a bank and launched station CKGB in Timmins.

With CKGB flourishing, Roy partnered with a politically connected friend to get a radio license in Kirkland Lake. He raised money from wealthy Kirkland Lake residents and launched CJKL, which was well received. Roy was on a roll but still on thin ice financially.

When the local newspaper in Timmins, the Citizen, attacked Roy’s station CKGB for running ads for a competing newspaper, Roy offered to buy the unprofitable Citizen for $6,000. The owner, a gentleman named Bartleman, accepted, and Roy financed the deal by providing $200 at closing and giving Bartleman twenty-eight promissory notes for $200 each, payable over twenty-eight months. Roy sold his supply store to an employee. He changed the Citizen to the Timmins Press, and in 1934 Roy was a publisher.

To learn best practices for newspapers, Roy looked up the names of a hundred American cities the size of Timmins and ordered a copy of each one’s paper. He measured the layout of each paper and estimated the earning power of a small rural paper. Using his analysis, he optimized the size of each section of the Press to maximize its earning power.

Roy also realized that he had to publish more frequently to beat the competing town paper. He went from weekly to twice a week and, finally, daily in September 1935. Going daily was painful for his staff to execute. Readers got their papers late for a few months until his team got the hang of things. Roy ended up having to borrow $4,000 to upgrade his equipment to make daily publication feasible, but the investment paid off. Readers enjoyed having a daily paper, and the Press became the popular town newspaper.

Roy wasn’t able to pay the promissory notes, so he made Bartleman and his associate directors on his board and gave them ownership stakes in his company. With an eye on growth, Roy bought another station, CJCS, in Stratford, Ontario. The fact that he never had enough money in his accounts to cover payroll didn’t stop Roy from acquiring to grow.

By this time, Roy was managing four radio stations, a paper, and team members in various cities. He didn’t have a partner, so he worked sixteen or seventeen hours a day, negatively impacting his time with his family. He lost some of his connection with them. But Roy was 42, and in his mind he was twelve years behind on becoming a millionaire, so the sacrifice was worth it. Little did he know he was about to meet someone who would help him take his company to the next level and improve his personal life.

A few weeks ago, I listened to an interview with Syed Balkhi, founder of WPBeginner and Awesome Motive. He recommended the trilogy of books on Roy Thomson, who founded what became the Thomson Reuters media empire and whose family is one of the wealthiest families in Canada. I wanted to learn more about Roy, so I read Roy Thomson of Fleet Street by Russell Braddon.

Roy was born in 1894 and raised in Toronto, Canada, by working-class parents. As a kid, he developed a love for numbers. For fun, he manually calculated the statistics of all baseball players from information he found in newspapers. At age 14, to help his family, he dropped out of school and started working full-time doing administrative work for local businesses.

Roy’s aunt was a shrewd investor. But Roy was shocked to learn she didn’t keep any records. He used his newly acquired bookkeeping skills to record her investments. She rewarded him by loaning him money to invest alongside her. Roy was obsessed with making money and was excited to invest with his aunt. At 17, he proclaimed to coworkers he’d be a millionaire by age 30.

The investments with his aunt did well, and Roy reinvested profits to buy his employer’s stock. He built an impressive $15,000 portfolio. Roy excelled at work. He became a branch manager and did outside sales for a local company. That role was pivotal because it taught him how to sell and, more importantly, helped him discover his passion for doing deals.

In 1917, Roy married Irma, and by the end of 1918, they had two children. Anxious to get rich, he took his $15,000, quit his job, and moved his family to remote Saskatchewan to become a farmer. The decision to purchase and farm 640 acres was a disastrous mistake. Roy lost much of his investment when he gave up farming within a year. He was 25, and he realized he couldn’t take losses like that if he wanted to become a millionaire by 30.

Automobile sales were exploding in 1920. Roy and his brother Carl pooled their money to start a company selling replacement parts to garages. To expand, they bought a machine shop, and by 1924 they’d grown the company to $700,000 in sales.

Roy was buying parts from manufacturers and selling them to garages. Expanding this business required inventory, which required capital, which Roy and Carl didn’t have. When the garages were slow to pay their bills, Roy and Bill had cash flow issues. They almost went bankrupt.

The brothers reworked their debts, and Roy left Toronto for Ottawa, which he saw as an untapped market for automotive parts. He and Carl set up a new Ottawa company, Service Supplies Limited. At the same time, in 1925, radios were new. Manufacturers were eager to sell them to businesses that sold to consumers. Trying to dig himself out of debt, Roy started selling radios too. By 1928, the new company was doing $80,000 a year in sales and the debts from their shuttered business had been paid off.

Roy wasn’t satisfied. He wanted to grow the company more. Hearing about Trimmis and Kirkland Lake, two rural cities thriving because of gold mines in Ontario, Roy moved his family to North Bay, Ontario, in 1928. Roy realized he had to help rural dealers. They didn’t know how to sell radios to consumers. Roy devised a door-to-door sales strategy that let consumers test radios for a week. If they liked them, he hoped they’d buy them. The strategy was innovative, but there was a significant problem that Roy and his dealers had overlooked: there was no radio signal in this remote area. There was nothing for people to listen to on the radio.

With the depression beginning to affect Roy’s dealers and payments from them to Roy slowing, Roy started to ponder how he could solve this problem. The more he thought about it, the more he realized there was only one way to solve it. He had to start a radio station.

I finished reading a second biography on William Richard “Billy” Wilkerson’s life. Unlike the first one, this one detailed his entire journey until his death in 1972. It also focused more on what led to his founding The Hollywood Reporter and his various entertainment and restaurant ventures.

I shared many of my concluding thoughts on Billy’s journey in an earlier post after reading the first biography. This post is about additional insights from the second biography.

How Did Billy’s Earlier Years Impact His Journey?

The death of his father led to Billy working in the film industry. Over roughly fifteen years, he worked in various roles at various companies in film production and distribution. He also managed his friend’s nickelodeon (i.e., theatre) and sold ads and wrote for a motion picture trade paper. These years of experience schooled Billy on the industry from various perspectives and led to key insights about himself and the industry. First, he was an entrepreneur and wanted to be his own boss. Next, the owners of movie studios amassed more of the industry’s profits than anyone else. Last, trade publications could wield immense power over an industry. These three key insights shaped his trajectory.

Billy’s first wife leaving him scarred him deeply. He was married five times. He wasn’t particularly close with wives two through four because he put his work ahead of them. Only after he had children with his fifth wife did he make spending time with his family a priority.

How Did Billy Become So Successful?

This book details Billy’s questionable actions and associations with criminal figures. It painted a picture of someone who didn’t mind using illegal means to accomplish a goal or obtain wealth. Partly this may be a sign of his time and place, but it’s clear that Billy’s comfort with doing things that weren’t aboveboard led to financial success and outsize influence. Billy was willing to do things and go places others weren’t to get what he wanted. This approach came with a cost. Billy went into hiding in Paris to avoid being killed by Bugsy Siegel, he owned several bulletproof cars, and his house was stocked with guns.

Billy was driven to succeed by hatred for movie studio bosses. Movie studio heads ran monopolies and operated similarly to robber barons. Billy felt wronged when they didn’t give his film a chance and held that grudge for decades. His desire to topple the studio bosses fueled his passion to make the Hollywood Reporter successful and dismantle what he viewed as an unfair studio system.

Billy was naturally gifted at understanding the psychology of the rich and famous. He repeatedly used this understanding to create content in the Reporter and numerous successful entertainment and dining venues that resonated with this group and made them want to be associated with Billy.

What Kind of Entrepreneur Was Billy?

Billy was a founder who enjoyed taking an idea from inception to an operating business, but he got bored easily and didn’t enjoy managing businesses. He ruled with an iron fist, which wasn’t uncommon for that period in history. This book highlighted Billy’s ability to weather massive misfortunes. Billy refused to be taken out of the game regardless of what life threw at him. He simply took the hit and kept going.

What Did I Learn from Billy’s Journey?

Billy’s journey is a cautionary tale. He had outsize success and impacted the movie industry, but the costs of operating unethically were high. His relationships, personal and professional, weren’t healthy. He was hated by many people whose lives he harmed. And the book never described a man who lived a happy life.

Billy had an outsize impact on Hollywood and Las Vegas. He was a complex man who lived a complicated life. Anyone interested in learning more about Billy or old Hollywood may enjoy this book.

In 1938, William Richard “Billy” Wilkerson and Edith divorced. Once again, Billy wasn’t single long. According to the biography I’m reading, he met Estelle Jackson Brown in October 1939, and they were married by December 1939. Billy’s personal life was stable again, but his business empire was shaky. He’d sold Café Trocadero so he wouldn’t have to pay bribes anymore, and California cracked down on vices like gambling.

Billy wasn’t the only one with business problems. Joe Schenck began having trouble coming up with $100,000 in cash for Willie Bioff every month to avoid unions striking at his 20th Century Fox. In early 1939, he gave Bioff a $100,000 company check, knowing that if the gangster deposited it, that would be enough evidence for authorities to bring Bioff down. Schenck alerted authorities to the deposited check, which instigated an FBI investigation. Schenck had opened Pandora’s box.  

With investigators’ scrutiny heightened, Schenck convinced Billy to revamp his new investment, Arrowhead Springs Hotel, three hours from Hollywood in San Bernardino. Billy agreed and turned the hotel into an exclusive getaway for the rich and famous. Unable to shake his old habit, he introduced gambling, which exploded in popularity. It was so popular that U.S. Marshals raided the hotel and shut it down.

In April 1941, Schenck was convicted of tax evasion and faced three years in prison. He agreed to testify against Bioff for a reduced sentence. In May 1941, Bioff was indicted for tax evasion and extortion, but he turned the tables. He entered federal witness protection and agreed to spill everything he knew to have all charges dropped. In 1942, Schenck began serving eighteen months but was released in four months after favors were called in. In December 1943, Johnny Rosselli was convicted of extortion and sentenced to ten years. The Hollywood Syndicate had collapsed, but Billy was never arrested. He narrowly escaped jail, but he couldn’t avoid another divorce. He and Brownie divorced in August 1942.

Around this time, Billy embarked on his Flamingo Hotel project and inadvertently ended up partnering with Bugsy Siegel, which I detailed in posts here, here, and here. In February 1946, Billie met 27-year-old Vivian Dubois at his Hollywood restaurant LaRue. In May they were married in Las Vegas. Billy started expressing his hatred for communism and displeasure that the U.S. didn’t stop Russia and Joseph Stalin from drawing an iron curtain around Eastern Europe. With the help of Howard Hughes, Billy obtained an FBI list of movie-industry people who supported communism. He then published editorials in the Reporter naming these people. Billy was a free speech advocate, but not when it came to communism. The Reporter’s sales increased, and other publications followed suit. Congress issued subpoenas, and studio heads were forced to testify. Billy created an anti-Communist movement. Many people on the Hollywood blacklist lost their jobs or were denied employment, even if they were innocent.

As this crusade was happening, movie studio bosses were grappling with competition from television and an antitrust lawsuit that reached the Supreme Court. In 1948, the Court ruled 7 to 1 that movie studios owning theatres constituted a monopoly. Studios tried to negotiate a compromise with the government, and Billy sensed that he could finally get revenge against the studios. He convinced recently paroled Rosselli, who was angry that studio bosses refused to help him after he got out of prison, to pressure government contacts Rosselli had paid off for years to reject any compromise from studios. The studios were forced to sell their theatres, their revenue declined, and they could no longer lock talent into long-term contracts. Actors and agents gained leverage by forcing studios to bid against each other for their services. After twenty years, Billy had finally exacted revenge on the studio bosses who rejected him and the studio system he hated.

In 1950, Billy and Vivian divorced, and in 1951, he met Beatrice Ruby Noble, known as Tichi. The 24-year-old was a housekeeper at Schenck’s beach house. Tichi became pregnant within a year, and after Billy realized she wasn’t trying to shake him down and medical tests confirmed he wasn’t sterile, the 60-year-old was excited to become a father. The two wed in 1951 and their son was born in October. Their daughter was born in 1953. Billy, now a family man, stopped gambling and started spending more time enjoying his wife and children.

Billy entertained the idea of selling the Reporter, but he decided to keep it. He continued running it in his mercurial style. Going to great lengths to end his partnership with Tom Seward after Seward sued him for paying gambling debts with partnership funds, Billy burned twenty years of business records. He ended up paying Seward $150,000 after much litigation, subpoenas, and search warrants, but he maintained complete control of his empire, which he ruled over until he died in 1962.

Billy was a complicated and flawed entrepreneur. Despite his shortcomings, he had a significant impact on Hollywood and entertainment in the United States. The Reporter is still in existence over ninety years after its founding.

As prohibition ended, organized crime, needing new revenue streams, began looking at the movie industry. Mobster Johnny Rosselli approached William Richard “Billy” Wilkerson about taking over Hollywood labor unions. According to the biography I’m reading, Billy brought in Joseph Schenck, head of 20th Century Fox, and the trio formed the Hollywood Syndicate. The group helped gangster George Browne get elected as the president of the International Alliance of Theatrical Stage Employees (IATSE), and Browne appointed Willie Bioff, also a gangster, as “his personal representative.” If IATSE called a strike, no movies could be produced. The Hollywood Syndicate started extracting a roughly $ 50,000-a-year bribe from each studio.

Around this time, Edith and Billy divorced. Edith was frustrated by their inability to have children and blamed Billy for not paying his 1929 debt to the New York City loan shark when her sister disappeared. Even though they divorced in August 1935, Edith continued working at The Hollywood Reporter until she retired in 1948. Billy was about 45, and he didn’t stay single long. In September, he met 20-year-old Rita Anne “Billie” Seward and married her by the end of that month. Billie’s brother, Tom Seward, became Billy’s right-hand man.

Gossip was a big part of what the Reporter published, and it sometimes led to scandals. This rubbed the studios the wrong way, and they would pull advertising from the publication. Billy’s response wasn’t always aboveboard. Sometimes he’d sell the same charity ad to several sponsors. Billy’s trick was to name only the charity in the ad, not the sponsor, so he could sell the ad up to a dozen times. This and other questionable tactics helped Billy fight back against the studios, and by 1936, the Reporter was known as “Hollywood’s Bible” and was capable of launching or killing careers. The studios had to respect the power Billy wielded.

As Billy’s success continued, he wanted to expand. He viewed London as a rapidly growing film market and launched the London Reporter in 1936. But British advertisers were part of an old-boy network, and Billy wasn’t invited in. The publication failed within five months. Billy next expanded his building and decided to try a new concept in the unused space. He started a high-end barbershop and men’s clothing store called Sunset House. It failed, and Billy lost $250,000.

By 1937, Billy’s marriage was falling apart. Billie wanted to adopt children, but the sterile Billy refused. In 1938, they divorced. That wasn’t the only thing falling apart. The Hollywood Syndicate was having problems with Bioff. Drunk on power, be began shaking down people the Syndicate hadn’t approved. Then he took things to the extreme and started to shake down Billy, demanding 50% of his restaurant profits or he’d have the workers strike at Café Trocadero. He demanded a $100,000 monthly payment from Schenck to avoid a strike at his 20th Century Fox studios. Both men agree to pay, with Billy paying roughly $20,000 a month. That same year, Billy decided he wanted out of the restaurant business and hired gangster Nola Hahn to stage a kitchen fire at Café Trocadero. Billy collected the insurance money and sold the property to Hahn for $268,000.

Billy’s problems were far from over. The secretive Hollywood Syndicate wouldn’t remain a secret for much longer.

William Richard “Billy” Wilkerson arrived in California in 1930 and set up Daily Printers Corporation in July. According to the biography, he borrowed $5,000 and launched The Hollywood Reporter. Printing costs were so high at the time that he bought a printing company so he could print in-house. His wife, Edith, handled administration and customer accounts and wrote much of the editorial copy.

Billy focused on writing a front-page editorial column called “Tradeviews.” It was part gossip and part Billy’s opinions. This column made him famous and would be a valuable weapon. Billy used it to criticize the Hollywood studio system, and the studio heads didn’t appreciate it. They tried to strong-arm Billy into writing what they wanted, but he refused. The studios retaliated and refused to advertise with him until he did as they said.

Billy was focused on providing content that readers wanted, which would grow his reader base. He instructed his reporters to do whatever had to be done to gather information—even go through the studios’ garbage. And Billy knew the studios didn’t treat workers well, so he championed the causes of blue-collar studio workers, directors, and others, which built him a loyal fan base. When newspapers around the country started picking up the Reporter’s editorials, Billy had the power to stop people from going to the movies, which reduced studio revenue.

By 1931, the Reporter was flush with ads and had power over the studios, who realized their plan to crush Billy had backfired. When Billy proved to Metro-Goldwyn-Mayer (MGM) head Louis B. Mayer that 5,000 papers nationwide reprinted the Reporter’s articles, Mayer was dumbfounded. Mayer and other studio heads agreed to yearly ad contracts with the Reporter to keep the peace with Billy. In just two years, Billy made the Reporter the most important film industry publication in Hollywood and was getting revenge on the people who killed his dream of owning a studio.

Billy and Edith missed New York food, and Billy was tired of driving around town for meetings. In May 1933, Billy opened Vendome, a lunchtime restaurant in Hollywood. He stocked delicacies from Europe and even sold European booze under the counter. This, combined with daily ads in the Reporter, made the restaurant the place to be seen by celebrities and the wealthy. It was wildly successful.  

In 1933, President Roosevelt’s five-day bank holiday closed banks nationwide to prevent bank runs. Studios took advantage of this, and MGM forced employees to take a 50% pay cut for eight weeks or be fired. Billy learned about MGM’s plan to make the reductions permanent and wrote a blistering piece in the Reporter backing the writers’ union. Furious, Mayer reversed the pay reduction at MGM. He was so worried about Billy’s power and influence through the Reporter that he tried to buy Billy’s business for $300,000. Billy refused to sell.

Billy didn’t just fight the studios; he also had to fight competition. New York City–based Variety was a successful weekly trade publication that began covering Hollywood in 1933 when it launched Daily Variety. Realizing he could be put out of business by the larger competitor, Billy began a war to stop Variety from getting advertising sales. He even set up a dirty-tricks department to wage this war. The tactics worked and Billy fended off the competitor, albeit with questionable tactics.

In 1934, Billy faced a challenge when his insurance required that the abandoned building he was renting for wine storage not remain vacant. Unable to rent it out or find another use, he decided to open Café Trocadero, a French-themed restaurant and nightclub. To get people to come to the empty establishment, he claimed reservations were booked two weeks out and put velvet ropes outside to make people wait. In 24 months, it had grossed $3.8 million, making it the most successful Depression-era restaurant and nightclub in America. Billy had the Midas touch.

In a few short years, Billy had gone from broke to the upper echelons of entertainment and business by fighting against the studio heads. Billy was about to take his hatred of the studios to another level—one that was illegal.

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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