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.