Mike Bloomberg was in a fortunate but uncertain situation. He had $10 million but didn’t have a job. He figured he had three options: look for a job, remain unemployed, or start a company. No one was calling and offering him a job, and he was too young to retire. He decided to start his own company.

According to the biography I’m reading, Mike asked himself what he had the resources, ability, interest, and contacts to do. In the 1960s, Wall Street was drowning in paperwork. In the late ’60s, Mike read that computers were good at storing data. He convinced the Salomon leaders to let him work on a project, nights and weekends, to automate data collection and retrieval. In 1972, he and a programmer launched B Page at Salomon. It was an internal system to access historical trading records and available data on public securities. It was also a messaging system for internal communication. When fixed trading commissions ended, Wall Street firms began making money using math-heavy arbitrage and trading strategies. B Page gave Salomon an edge over other firms.

Mike had money and knew smart people at Salomon, so resources weren’t an issue. He’d figured out how to create a data system for Wall Street investors, was interested in data and financial markets, and had contacts all over Wall Street. He started a company offering software that let non-mathematicians analyze bond information. In 1981, he put $300,000 in a business checking account and recruited four coworkers from Salomon.

Mike needed credibility and revenue for his start-up, so he did a six-month consulting project with Merrill Lynch and was paid $100,000. He used that project to get introduced to Merrill’s leader of capital markets. He pitched a nonexistent product to the leader and told him he didn’t have to pay unless it was delivered on time. Merrill Lynch liked the product and agreed to the no-risk deal. Mike hired salespeople and operators, even though the product was still being built and they had only one customer. He blew through $4 million and ultimately hired almost two dozen people. He began to wonder if he was jeopardizing his wealth and reputation.

In July 1983, Mike’s firm, Innovative Market Systems, delivered its Market Master product to Merrill. A computer terminal with a keyboard allowed users to access bond market data and analyze whether a bond was cheap or expensive. The product was delivered on time and worked well enough for Merrill to commit to purchasing. Merrill paid a $600,000 one-time custom development fee and $1,000 monthly for each terminal under a two-year agreement. Merrill initially took delivery of twenty-two terminals, which resulted in $240,000 in subscription revenue over two years, bringing the total deal value to $840,000.

The Merrill deal led to credibility and other clients, such as the Bank of England, signing on—and to a critical acqui-hire. Michael met data entrepreneur John Aubert in Merrill’s cafeteria in 1984. John’s three-person firm was skilled at gathering and structuring data. The day they met, Mike agreed to absorb John’s company. John went on to start Bloomberg’s data-collection facility and devised Bloomberg’s data-collection process, which included a crucial analytical component. Data was the backbone of Mike’s company, and John’s skills laid the foundation for the company’s data edge over competitors.  

Things were starting to click for Mike. The more he thought about his data and analysis business, the more he realized he needed to find different ways to distribute his product.

Earlier this month, Michael “Mike” Bloomberg announced that he’s donating $600 million to four historically Black medical schools. This caught my attention. I researched Mike and his media and technology company. I’ve been reading biographies about media entrepreneurs recently, so I read the updated version of his autobiography Bloomberg by Bloomberg.

Mike was born in 1942 in a middle-class family. His father was an accountant at a dairy. His hometown, Medford, Massachusetts, was a blue-collar city outside Boston where few people attended college. Mike attending Johns Hopkins was serendipitous—someone at his part-time job told him about Hopkins and encouraged him to apply. He was an average student but got into Harvard Business School, likely because of his various leadership roles as an undergrad.

Mike planned to serve in the military to fight in the Vietnam War after graduating from Harvard, but the military rejected him because of his flat feet. Jobless and with student loans to pay a few weeks before graduation, Mike took the advice of a friend who suggested he apply to be an institutional salesperson or equity trader. Mike had no idea what people in those roles did, but he needed money. He was hired at Salomon Brothers in 1966. Securities trading and sales were considered second-class jobs, not something Ivy League graduates did. The job didn’t pay even enough to cover his bills. He started off doing clerical work but eventually got a break—he was asked to help build the firm’s business doing block trades, a new thing at the time, for institutional clients.

Block trading became Salomon’s most visible department, and Mike was promoted to general partner in 1972. In 1973, his boss had a fistfight with another partner on the trading floor, and Mike was given responsibility for all stock trading. In 1979, the block-trading business became unprofitable, and Mike was assigned to oversee the firm’s information systems.

Mike pushed for Salomon to implement a computer system that would enable cooperation across departments and firmwide risk management. This push caused a political battle between Mike and some members of the firm’s executive committee. Then in August 1981, the executive committee merged the 71-year-old partnership with public commodities trading firm Phibro Corporation. The merger was bittersweet for Mike. His ownership in the partnership netted him $10 million in cash and convertible bonds when the merger closed. But his rivalry with certain executive committee members had caught up with him; he wasn’t offered employment with the merged company. He was being fired.

After fifteen years, Mike was leaving the only full-time job he’d ever known. He was 39 and had a wife and young daughter. He had to figure out what he was going to do next.

I’ve finished reading a biography of Roy Thomson’s journey. It was written in 1965 when Roy was around 71. Roy lived another eleven years. In 1976, he wrote an autobiography that focused on the building of his British empire. I plan to read it.

How Did Roy’s Early Years Affect His Trajectory?

Roy’s parents were working class; his father was a barber, and his mother was a maid at a hotel. Roy’s great aunt, Sarah Hislop, was not working class. She invested in mortgages, and she held the mortgage on the home Roy’s parents owned. Given the family’s limited means, paying off that mortgage was their highest priority. This dynamic contributed to Roy needing to work as early as legally permissible and dropping out of school at age 14 to work full-time. The contrast between Aunt Sarah and Roy’s parents made an impression on Roy. His parents were working to scrape together enough money to pay Aunt Sarah. Aunt Sarah’s loan generated income for her, regardless of whether she worked. Roy’s parents worked for money, and Aunt Sarah’s money worked for her. Roy wanted the latter. Like Aunt Sarah, he wanted to be wealthy, and he developed a “passionate devotion to money.”

Aunt Sarah noticed his respect for money and loaned 15-year-old Roy capital to invest in mortgages alongside her. Roy was instantly hooked—hooked on the notion that he could borrow money to purchase investments and buy things that would generate cash in the future.

Roy told coworkers he’d be a millionaire by age 30. He didn’t achieve that goal, but becoming wealthy became the driving force in his life.

What Strategy Did Roy Employ to Achieve Success?

Roy learned that selling physical products and scaling that business model is complex. To sell more products, you need more inventory; to buy more inventory, you need capital to purchase it and, sometimes, expand your capability to store it.

Roy created a radio station as a way to sell more radios but quickly learned it was much easier to increase revenue in a radio station than in a company selling radios. The more listeners tuned in, the more people the ads reached and the more Roy could charge for advertising. He realized that radio broadcasting as a business model had leverage because his costs remained the same as listeners and ad revenue increased. The cost of marginal replication was low or zero, and revenue increases could happen rapidly. This was true for television broadcasting and newspapers too, which he expanded into. Media became the backbone of Roy’s strategy. Whether his customers were reading newspapers, listening to radio, or watching TV, Roy could sell their attention to advertisers for a profit.

Starting a radio station, television station, or newspaper from scratch is hard and takes time. Roy started off doing this but realized he preferred to improve existing properties. An underperforming property could be acquired for a low multiple (i.e., low price), especially if it was in a rural town and had been family-owned for generations. Once it was improved and benefiting from the economies of scale by being part of his empire, it could rapidly produce more cash. Buying media properties, improving operations, and generating cash became vital to Roy’s strategy.

Roy said, “My fortune is as large as my credit rating . . . and my credit rating is limitless.” This pretty much sums up the next part of Roy’s strategy. He believed in using debt, a form of capital leverage, to obtain the capital needed to acquire media properties. He understood two things about debt:

• Rate of return – Roy used borrowed money when the potential rate of return exceeded his interest rate. For example, when he could borrow money at 5% and buy an asset that in a year would generate a cash return of at least 10% of the purchase price, buying that asset with debt made sense.
• Ownership – Roy was focused on the companies he acquired generating cash years into the future. He didn’t give up ownership in his companies when he used debt, which meant he owned those future cash flow streams (after the debt was paid off). If he’d raised capital by selling equity (i.e., ownership), other investors would own part of those future cash flow streams in perpetuity.  

Another thing that stood out to me was how Roy used two forms of leverage. He combined a highly scalable media business model (low to no cost of marginal replication) with capital leverage (debt). The combination of the two, along with luck and a focus on cash flow, turbocharged his ability to build his empire and wealth.

What about Roy’s Execution Made Him Successful?

Roy eventually learned to stay out of the details and focus on strategy and acquisitions. Like many entrepreneurs, he learned this the hard way. After years of being in the weeds, he hired Jack Kent Cooke, who freed him up. He learned his company could move faster with him out of the details. From that point on, he ran a decentralized company with nonfinancial decision-making at each media property that aligned with the community being served. Henry Singleton at Teledyne and Warren Buffett at Berkshire Hathaway used similar approaches.  

Roy also put a ton of hours into his work. He was known to work sixteen- and seventeen-hour days and sometimes wouldn’t see his family until the weekend. He got more done than the average person. Working that much had a downside, though. When his wife passed away, he regretted not spending more time with her.

Roy’s story was inspiring. He failed for many years, first as a farmer, then selling automotive parts, and then as an electronics retailer, before realizing the power of media. But when he figured it out, he excelled. He built an empire that still stands today.

Access to capital was key to Roy Thomson’s acquisition strategy and success, according to the biography I'm reading. When possible, he avoided selling equity (ownership) in his company to raise capital. He wanted all the profits he knew he’d eventually generate to be his, not other shareholders’. He also despised the idea of having to deal with a board of directors, seeing the conflicting opinions of directors as a waste of his time. Roy believed that if he could borrow at 5% and get a return of 10% or more on the borrowed capital, it was sensible to raise capital through debt instead of selling equity.

In 1955, Roy publicly declared his intent to bid for the charter to launch an independent Scottish television station. No one in Scotland understood the opportunity like Roy did, and the elites declined to invest. He even asked colleagues at All-Canada Radio to partner with him, but they too declined. These people didn’t know that Roy had obsessed over this station and done extensive research, sending his lieutenant to tour American and Canadian stations and ask questions about budgets. Roy analyzed spending per capita in Scotland compared to England to determine what ad rates he could charge. His work paid off, and in May 1956, regulators gave Roy a charter to establish Scottish Television Limited (STV), which he was chairman of.

To finance the deal, Roy tried to borrow £400,000, but the Scottish bank gave him only £240,000, which surprised him. Roy assembled an investor group and valued the company at £400,000, equal to the required start-up capital. Roy was £160,000 short of his goal and decided to raise it primarily by issuing £120,000 in bonds, but also by selling 40,000 shares of equity for £40,000 to an investor group. Roy was one of the investors in that group; he bought £32,000 worth, or 80%. Instead of spending £400,000 of his own funds to own 100%, Roy spent £32,0000 to own 80%. He’d sold as little company equity as possible and managed to keep control and as much of the eventual profits as possible.

STV was a big hit. In its first month, STV made a £10,000 profit. Quickly, it was on track to do £1,000,000 in profit in the first year. Nobody except Roy had expected STV to turn a profit. Within two years, those 40,000 shares in STV that were initially worth £400,000 exploded in value to millions—so much so that Roy used them as part of a transaction to purchase an entire chain of British newspapers.

In 1958, Kemsley Press, a prestigious company that owned eighteen British newspapers, asked Roy if he was still interested in acquiring them. The deal was done in a complicated transaction that took sixteen intense days to negotiate. It had three parts:

• Kemsley Press acquired STV from Roy for £5.5 million: £1 million in cash, £500,000 in bonds, and £4 million in newly issued Kemsley shares
• Roy then bought Lord Kemsley’s controlling stake in Kemsley Press for £5 million: £1 million cash from the prior transaction, a £1 million promissory note with a ten-year term, and £3 million in cash that Roy borrowed from the bank.
• Roy made a tender offer (i.e., offered to buy at a set price) for Kemsley shares owned by other minority shareholders, too.

In roughly seven years, Roy had gone from electoral defeat in Canada to becoming a press baron in the United Kingdom. With the Kemsley deal, he’d reached his goal of owning fifty-two newspapers. At age 40, Roy was broke and heavily indebted. By age 65, he had empires in two countries on different continents. Roy continued to build his empire and expanded to have newspapers in Africa, Australia, and other places.

Roy also achieved his other goal and was given the title “baron” in 1964, becoming Lord Thomson of Fleet Street. Roy had reached the upper echelon of elite global circles, and he did it his way, on his terms. By 1964, his hard work had created an empire valued at roughly £100 million. His family is still one of the wealthiest, if not the wealthiest, families in Canada.

Roy passed away in 1976 at the age of 82, but his family continues to run his empire. In 2008, Roy’s Thomson Corporation acquired Reuters Group plc to form what is now known as Thomson Reuters, a multinational information company with a market capitalization (i.e., valuation) of roughly $74 billion as of this writing.

Roy Thomson was a dynamic entrepreneur who built a massive newspaper and media empire through savvy dealmaking and a dogged work ethic.

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. 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. 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.