This week I reflected on my personal project around reading books and sharing what I’m learning via blog posts and audio podcasts. Creating a digest of each book I read has been the focus of the last few weeks. I’m currently reading older books that don’t have a Kindle or other electronic version available, so the digest must be created 100% by hand. The more I create these digests, the more I realize how foundational they are and how important it is to make them high quality. They serve as the foundation for my blog posts and podcasts. They also allow me to review concepts from a book quickly. Creating digests is something new for me, so it’s painful and slow now. But it should become easier as I get more reps.

Right now, I’m reading daily, working on a digest daily, and blogging daily about what I read. These feel like good habits that I can sustain. But I haven’t settled on a recording frequency. Daily doesn’t feel appropriate anymore. I want to focus on quality more, and it’s hard to do that and publish a recording every day.

Today, I decided to test a different approach for a few weeks. I’m a big fan of turning my goals into habits as much as possible, so I’ll try setting a goal and figuring out what frequency is needed to turn it into a habit. Instead of focusing on recording frequency, I’m focusing now on how often I publish a podcast series. For context, I publish a series of five episodes for each book I read. I’m starting by aiming to publish a series every other week, which means I’ll publish roughly two series per month. From there, I’ll test and figure out what recording and editing frequency make sense to make that happen. This will also allow me to improve the quality of the recordings intentionally.

So, to recap, this is what I’m aiming for over the next few weeks:

• Reading  – daily
• Digest creation – daily
• Publishing blog – daily
• Publishing audio podcast series – every two weeks

This feels like a good change. I’m curious to see how it plays out over the next few weeks.

When I began recording audio podcast episodes in April, the recordings were awful. I figured the more practice I got, the better the episodes would be, so I set a goal to record 100 episodes by the end of summer and then reevaluate. I’m at 92 episodes and will be at 100 soon.

The series I’m most proud of is the John H. Johnson series. I felt I’d made a breakthrough. I figured out my content format, and things started to click. I’m proud of the quality of that series, which isn’t the case for prior series. I recorded another series after Johnson’s and then took a break from recording to focus more on improving my process to create a digest of each biography I read.

I’m back recording this week. I listened to the John H. Johnson series for the first time in a few weeks. I wasn’t as impressed as I had been. The quality was better than that of prior series, but I picked up on many areas where I need to improve. I must improve my delivery, connect the dots for listeners, and do various other things. I’m still proud of this series, but it’s not the Mona Lisa I thought it was a few weeks ago.

What happened? Recording those first 92 episodes, I published one almost daily. This aggressive schedule put me deep into the weeds of creating recordings. I got lots of reps, which was needed and helpful. But it made it harder to see where I needed to improve and to gauge the quality of my recordings. Now that I’m not publishing every day, I can see things more clearly. The areas where I need to improve are more obvious.

This reminded me that when I’m aggressively doing something new, I must avoid getting caught up in hitting metrics or the minutia of execution. I need to take time to zoom out and consider the big picture.

For this project, stepping back and focusing on another part of it was helpful. I returned with a fresh perspective and could see the forest, not just the trees.

This week I’m doing more test runs before I record an episode, so the recording process is a bit slower. I hope the quality of the recordings will be higher. I’m also testing some other ideas to help me be more relaxed when I record.

Current Project: Reading books about entrepreneurs and sharing what I learned from them via blog posts and audio podcasts

Mission: Create a library of wisdom from notable entrepreneurs that current entrepreneurs can leverage to increase their chances of success

Metrics (cumulative since 4/1/24):

• Total book digests created: 9 (+1)
• Total blog posts published: 126 (+7)
• Total audio recordings published: 92 (+0)
• Recent digest length: 8% of the book’s length (+4%)
• Recent recording length: no recordings this past week

What I completed this week (link to last week’s commitments):

• Created a digest for the second biography I read about Billy Wilkerson, founder and publisher of The Hollywood Reporter and founder of the Flamingo Hotel in Las Vegas
• Finished the digest for Ted Turner’s autobiography
• Had three additional feedback sessions

Content:

• No recordings this past week

What I’ll do next week:

• Read the biography of Roy Thomson, founder of what became Thomson Reuters
• Create a digest for one book
• Write and publish blog posts about one book: roughly seven posts
• Record audio podcast about two books: roughly ten recordings
• Publish audio podcast about one book: roughly five recordings
• Complete three feedback sessions

Asks:

• No asks this week

Week two hundred twenty-eight was another week of learning. Looking forward to next week!

Current Project: Reading books about entrepreneurs and sharing what I learned from them via blog posts and audio podcasts

Mission: Create a library of wisdom from notable entrepreneurs that current entrepreneurs can leverage to increase their chances of success

What I struggled with:

• Last week I focused on honing my process of distilling a book down to a digest and testing a progressive summarization method. It’s painful to do this with books that don’t have an EPUB (i.e., e-book) file—it must be done by hand. I’m trying to find the right balance between capturing too little and too much in a digest. And trying to figure out a good length for a digest relative to a book’s length. And trying to figure out where it makes the most sense to add context and links to external sources in the digest without disrupting the flow of the story. Lots of work to do here. The quality of the digest affects the quality of what I can share with others.    
• Reading, creating a digest, and publishing blog posts for one book a week is doable. Adding on top of that recording, editing, and publishing a pod series the same week has been a struggle.

What I learned:

• I’ll start measuring the number of book digests I create and their length (relative to the book’s length). If I don’t measure this, the quality of these digests likely won’t improve.
• If an entrepreneur endorses a biography, that’s a good sign that the biography is high quality and worth reading.
• I must screen books continually. I must identify high-quality books I want to read while I’m still reading another one. Waiting until I finish a book to start screening for the next one has led to spending too much time on books that aren’t excellent.
• Biographies that include specific information about how entrepreneurs solved problems and specific financial information are more likely to include actionable insights that other entrepreneurs will find useful.
• Not creating or listening to my podcast episodes for a few weeks had an unexpected benefit. When I listened again after a break, I was able to pick out areas of improvement I’d missed before.

Those are my struggles and learnings from the week!

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.

Current Project: Reading books about entrepreneurs and sharing what I learned from them via blog posts and audio podcasts

Mission: Create a library of wisdom from notable entrepreneurs that current entrepreneurs can leverage to increase their chances of success

Metrics (cumulative since 4/1/24):

• Total audio recordings published: 92 (+0)
• Total blog posts published: 126 (+7)
• Average recording length: no recordings this past week

What I completed this week (link to last week’s commitments):

• Read a second biography about Billy Wilkerson, founder and publisher of The Hollywood Reporter and founder of the Flamingo Hotel in Las Vegas
• Had three additional feedback sessions

Content:

• No recordings this past week

What I’ll do next week:

• Distill and document one book
• Write and publish blog posts about one book: roughly seven posts
• Record audio podcast about two books: roughly ten recordings
• Publish audio podcast about one book: roughly five recordings
• Complete three feedback sessions

Asks:

• Listen to the series on John H. Johnson and provide feedback on how I can improve.

Week two hundred twenty-seven was another week of learning. Looking forward to next week!