I finished reading about William Richard “Billy” Wilkerson’s journey. The biography details Billy’s life through 1947, when he was about 57. Billy passed away in 1972 at age 71.

How Did Billy’s Early Years Affect His Trajectory?

Billy’s family was financially unstable because of his father’s gambling trade. Then his father’s unexpected death thrust Billy and his mother into poverty. Fear of poverty would drive Billy’s work ethic for the rest of his life. He vowed that neither he nor his mother would ever experience that again.

Billy may have inherited a compulsive personality or developed one by watching his father. Billy began gambling as a young man, and it became a full-blown addiction by the 1940s. Trying to satisfy his need to gamble, along with his fear of poverty, is what drove him to build the Flamingo Hotel. And Billy was compulsive in other areas as well. He was known to drink an average of twenty Cokes and smoke three packs of cigarettes a day while working at his desk.

How Did Billy Become So Successful?

Billy didn’t have a safety net and feared failure, so he was extremely detailed in his planning and execution. This attention to detail served him well and led to The Hollywood Reporter and his various restaurants and nightclubs being known for quality and attention to detail. This was perfect for attracting the elite patrons Billy targeted who happily paid premium prices.

The businesses Billy launched attracted elites from various networks. People wanted favorable write-ups in The Hollywood Reporter or reservations at his popular restaurants and night spots. As a result, Billy was able to build a Rolodex of influential people who sometimes owed him favors. This put him amid the flow of information, so prime opportunities came his way. It also put him in position to open doors and get things done that might seem impossible. Billy’s businesses reduced his network distance and allowed him to create relationships with the right people, which benefited him tremendously. The more elite people who knew him, the more elite people there were who wanted to know him.

Billy got into a growing market early and rode the wave of growth. He fell into the film business in the 1910s but soon realized its potential. As it grew and advanced to motion pictures, he moved to the epicenter of this rapidly growing industry: Hollywood. He then positioned himself as the source of news about the industry. As the movie industry's popularity among the masses grew, The Hollywood Reporter’s popularity rose too. Even the President of the United States was an avid reader. Billy’s magazine was the conduit through which everyone learned about the fascinating, new, and rapidly growing industry. This gave him tremendous power and led to big profits.

Billy also combined being a visionary with an ability to think through the necessary plans and closely manage their execution. His ability to think at a high level and get into the execution weeds contributed to his success.

What Kind of Entrepreneur Was Billy?

Billy was a founder. He didn’t focus exclusively on one business, but he built his businesses from the ground up. He never bought anything. He started with a vision for each and worked to turn that vision into reality. He went from an idea to a thriving, operating business repeatedly and managed several successful companies simultaneously.

Billy wasn’t the greatest capital allocator, though. He was known to lease his restaurant locations instead of buying them and rarely reinvested profits to grow his businesses. This was likely because his gambling addiction consumed so much cash.

Billy was never content and got bored easily. This likely contributed to his bizarre pattern of selling some of his businesses on a whim when they were doing well. This never made sense to those around him, but Billy was sometimes restless and enjoyed the thrill of pursuing new endeavors.

What Did I Learn from Billy’s Journey?

My biggest takeaway from this biography is that there’s no such thing as a good partnership if your partner is a bad person. Even if that person brings tremendous complementary skills or vital resources to the table, it’s not worth it. Bad people often look out only for their own interests and don’t honor their commitments. Great paperwork can’t protect you from a bad partner, so avoid bad partners at all costs. Do your research before you go into business with anyone.

Control is why many entrepreneurs start companies. When they lose control, they become miserable.

Some businesses have properties that allow them to manufacture magnetic luck, which is the hardest type of luck to have. If a business has these properties, the returns can far exceed the financial returns.

Building businesses that generate cash flows consistently and avoiding debt is the way to control your destiny. Even if you have a gambling problem, those businesses will replenish the cash you gambled away. Limiting debt allows you to weather any rough periods and maintain ownership of your cash-generating businesses.

Billy was a colorful entrepreneur whose life was full of excitement. His vision reshaped Las Vegas from a desert town to an entertainment metropolis. Ninety-three years after Billy printed his first issue, The Hollywood Reporter is still going strong. I’m glad I stumbled upon Billy, and I plan to look for more books about his journey.

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