In 1994, Jolyon Connell recognized that newspapers were bigger but people were busier, so they had less time to read them. He created a weekly digest magazine, The Week, to solve this problem. When Felix Dennis heard about the magazine, he invested. Within a year, he had 51% ownership. According to the biography about Dennis, he saw the magazine’s potential and had the resources at Dennis Publishing to take it to the next level. Realizing “the reader was king,” he focused on building a solid subscription base by adding value for readers. It worked, and the U.S. version launched in 2001. The Week was on a par with Newsweek and Time magazines and gained Dennis a level of respect from other publishers, which had avoided him before.

In 1995, Dennis Publishing launched Maxim magazine. The secret to its breakout success was a gap in the market. No one was publishing magazines for young men, ages 18 to 34, as they were for young women. Women’s magazines were more general. Magazines targeting men were specialized. Young men interested in science or physical fitness also “watched sport[s], talked about girls, and ate chicken wings.” Maxim filled this void by appealing to the universal interests of all men in a bold way. It sold 350,000 copies in the UK when it launched.

In 1997, Maxim U.S. was launched by Dennis and his two U.S. partners, Peter Godfrey and Bob Bartner. Creative marketing became a key to U.S. success. Maxim became known for throwing unbelievable parties, which gained celebrity attention and made attractive female celebrities inclined to pose on the magazine’s cover. It also creatively engineered getting promotion from Howard Stern, whose radio show was one of the most popular in the nation. Maxim was a gigantic success in the U.S. and sold 1.2 million copies per issue—10 or 20 times more than rivals like GQ and Esquire. At one point, Maxim U.S.’s ad rates rivaled TV ad rates. Maxim gained a cult following because, as Dennis put it, “it was the first beer truck to reach the desert.” Maxim positioned itself as the best conduit to connect advertisers with a large audience in this hard-to-penetrate demographic.

In 2007, Maxim was wildly successful in various countries when Dennis Publishing sold Maxim, Blender, and Stuff magazines to private equity firm Quadrangle Capital Partners, netting $240 million.

Flush with cash, Felix started to lean more into a passion he'd be developing for almost a decade, poetry. He bought a home on Mustique Island in the Caribbean and spent most of his time there, writing poetry. He published books of poetry and even went on tours reading his poetry in the U.S. and UK. Then, in 2011, Felix began to have health issues. First it was throat cancer, which shocked him. He was lucky; he survived after successful neck and mouth surgery. He eagerly resumed his poetry tours when, in 2013, he was diagnosed with terminal lung cancer. That diagnosis was devastating, and Felix decided to spend his remaining time mostly alone. On Sunday, June 22, 2014, Felix passed away.

Dennis was a pirate and maverick who happened to also be an entrepreneur. He enjoyed going against the establishment and shaking things up. He forced his way into what was then a stuffy industry and left a lasting impression on it. His outsize success forced his peers to respect him and change how they thought about the publishing business. Dennis’s track record of success over decades was undeniable, and many of the publications he started still exist today. But for all his success in publishing, his true passion ended up being writing and sharing his poetry. Building a publishing empire was a means to that end for Dennis.

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Felix Dennis began to hit his stride after selling MacUser magazine in 1986. According to the biography of his life, he’d landed on a strategy: creating magazines in growing markets, building them up, and selling them to larger publishing houses. That strategy helped him build his initial capital base, but it was about to change.

When MacUser was sold, Dennis and his partners realized that the biggest ad source was computer component sellers. Ads were driving massive revenue for those sellers, they discovered. The trio decided to launch Micro Warehouse as a mail-order company selling computer parts. It helped that they’d managed to secure 24 pages of free advertising as part of the MacUser sale.

The trio landed on two magic ingredients. They used sales to individual users of Mac computers inside corporations as a trojan horse to eventually sell parts to PC users (a much bigger market) in those organizations, too. And they offered $3 overnight shipping to build trust with corporations that weren’t yet comfortable with mail order. These ingredients, along with Dennis creating an attractive catalog, quickly produced $500 million in annual revenue. When the company held its IPO in 1992, it was receiving ten thousand calls from customers daily. The IPO was a huge financial success for Dennis and his partners.

During this period, Felix launched and acquired several other publications and renamed his firm Dennis Publishing. But he was also dealing with personal demons. He began to hire prostitutes to feed his sex addiction. He also developed an addiction to crack cocaine. These problems and a grueling work schedule led to Dennis being hospitalized and almost dying at age 41. This near-death experience, combined with financial freedom and other factors, would lead to Dennis discovering his true passion and next career.

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After the Oz trial, Felix Dennis was on a mission: to make money so he’d have the resources to defend himself if necessary. And he would make that money doing what he knew best: publishing. Oz magazine shut down in 1973, and Dennis set up a new company, H. Bunch Associates, with Dick Pountain.

Their first foray was into the world of Bruce Lee and Kung Fu. They published a poster magazine, which was wildly successful. This led to a variety of merchandising products and a book. All these items did well, and the money rolled in. Bruce Lee saved them.

Dennis started seeking other magazine opportunities. He co-authored a book about Muhammad Ali, which did well. He tried a variety of poster magazines, including Starsky & Hutch. Dennis’s new mindset had taken him from idealistic hippie publisher to opportunistic, mainstream publisher.

He also searched for opportunities in the United States, and set up a new company, Paradise Publications, with Peter Godfrey and Bob Bartner. This partnership would change Dennis’s life.

Around 1980, Felix acquired majority ownership in Personal Computer World magazine because the owner had followed the Oz trial and greatly respected Felix. In 1982, Felix sold the magazine to a large publisher for £3 million. It was his first taste of real money.

In 1984, Felix launched MacUser and began managing his company from New York City. MacUser was in partnership with Godfrey and Bartner. Felix handled creative work, and they handled distribution and printing in the States.

Circulation soared, and in 1986, Ziff Davis bought MacUser magazine for $21 million. Felix and his partners had life-changing money. But Dennis wasn’t done yet; in fact, he was just getting warmed up.

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Felix Dennis founded Dennis Publishing, created Maxim magazine, and cofounded Micro Warehouse Inc. I read Dennis’s book How to Get Rich: One of the World's Greatest Entrepreneurs Shares His Secrets last month and wanted to know more about his journey, so I read the biography of his life, More Lives Than One: The Extraordinary Life of Felix Dennis by Fregus Byrne.

Dennis was born in the United Kingdom in 1947. His father was a war veteran who opened a general store. Though his parents worked fourteen hours a day, the store failed. When Felix was four, his father went to Australia in search of a better life for his family. He never returned. Dennis never saw his father again, and his parents divorced years later.

Like his mother, Dennis was dominant and abrasive, and the two butted heads constantly. Growing up without a father forced Felix to grow up quickly and assume the role of head of the house. He had a disdain for authority from an early age, which led to his expulsion from multiple schools.

Dennis joined a band in 1962 and developed his showmanship skills on stage, but he was kicked out because he was too aggressive and needed to run the show. Around this time, he was expelled from Harrow Technical College and School of Art.

At this point in his life, Dennis was directionless. Then he noticed a magazine called London Oz and, after a night of drinking, recorded his thoughts about the publication. He mailed the tape to the magazine’s headquarters, and it was featured in a BBC story. The founder gave Dennis a bale of magazines to compensate him. Dennis immediately sold all of them, and that led to a 50/50 sales deal. After continued sales success, Dennis joined the magazine’s team. He brought energy and helped the magazine realize that reader demand was stronger than they’d known.

Dennis spearheaded focusing advertising sales on the music industry, which kept the company afloat. He then became the business manager and got the business operations and finances in order. He also developed a keen eye for what would resonate with readers and assisted in the editorial direction of each issue.

The magazine’s 1960s hippie vibe clashed with the conservative views held by the British establishment. When the magazine published an edgy issue, its offices were raided by the Obscene Publications Squad. Dennis and the two other founders were arrested and tried. They were found guilty on two of three charges and Dennis was sentenced to nine months’ incarceration.

The media, realizing the repercussions of these sentences for the media industry, railed against them. The public was outraged. People demonstrated. After political pressure from Parliament, the convictions were overturned on appeal. Decades later, this trial was still talked about as an event that changed British society by advancing freedom against the establishment and challenging its authority.

For Dennis, the trial was life-changing. It highlighted the fact that without money, he couldn’t fight back against “bogus” charges. Had he had money, his case would never have gone to trial. He realized how lucky he was to not be in jail. He’d never thought about money before, but after that experience, it was all he thought about. He never wanted to be unable to defend himself again. He was determined to make money, and a lot of it.

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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 (+7)
• Total blog posts published: 112 (+7)
• Average recording: roughly 12 minutes (-4) for a biography or autobiography

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

• Read the biography of Felix Dennis, founder of Maxim magazine
• Continued reading Building a Story Brand: Clarify Your Message So Customers Will Listen by Donald Miller
• Had four additional feedback sessions
• Compiled and sorted feedback from sessions completed the week of 7/8/24

Content:

• Refined the intro to include the problem I’m helping entrepreneurs solve
• Tested making episodes shorter

What I’ll do next week:

• Read one biography or autobiography
• Write seven blog posts and record seven audio posts
• Continue reading one of the books about storytelling that I purchased; this is a carryover from last week
• 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-five was another week of learning. Looking forward to next week!

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Last Week’s Struggles and Lessons (Week Ending 7/21/24)

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:

• No major struggles  

What I learned:

• After reading a biography, I do a series on that entrepreneur in, typically, five parts. Recording and publishing daily meant each part was created in isolation, so the series didn’t flow as smoothly for the listener.
• Enhancing my blog posts with context and using them as outlines has made the recordings more concise.
• Listeners are indifferent to whether I publish audio podcast episodes daily or weekly.
• A Netflix-style drop—publishing an entire five-part series on a single day—garnered more listens for that series compared to previous series.

Those are my struggles and learnings from the week!

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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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In December 1946, William Richard “Billy” Wilkerson received a call from J. Edgar Hoover, the director of the FBI. According to the biography of his life, the two were cordial friends who enjoyed betting on horse races and opposed communism. Hoover warned Billy that Benjamin “Bugsy” Siegel was dangerous and that the investor group might try to take control of his project, the Flamingo Hotel—and that Billy’s life might be in danger. The warning came too late; Billy was in too deep.

Two weeks before the Flamingo Hotel’s rushed opening, Bugsy called a meeting of shareholders in Las Vegas and announced there that he’d sold 150% of the project to investors. All shareholders would need to take a haircut to resolve the situation. Bugsy told Billy that he’d have to give up his 48% ownership stake and wouldn’t be paid for it—and if he didn’t, he (Bugsy) would be killed, and further, that if he were going to die, he wouldn’t go alone; he’d kill Billy first. Billy then realized that Bugsy had no intention of honoring his legal commitments.

His life in danger, Billy rushed back to Hollywood that same night. His lawyer threatened Bugsy and filed affidavits about the meeting with the district attorneys in Las Vegas and Los Angeles, the FBI, and the attorney general.

Billy went to Paris to hide. He still believed the investor group would fire Bugsy once they found out what Bugsy was doing. Billy decided to make sure the investors knew how bad things were. He used The Hollywood Reporter to publicize the project’s cost at the time: over $5 million, five times Billy’s original budget. The investor group now knew what had been hidden from them. This was a dangerous move by Billy.

Bugsy moved forward with the opening on December 26, 1946, and it was an epic failure. As Billy had predicted, with no hotel rooms available to gamblers, they took their winnings elsewhere. Within two weeks the casino had lost $275,000. Bugsy couldn’t understand what was happening and shut down the entire operation in late January. He had spent an additional $750,000 on operating and building costs. By April 1947, the total project cost was over $6 million.

Billy’s lawyer urged him to sell, but he refused. He believed his 48% ownership in the $6 million investment would do well once Bugsy was replaced. But hiding in isolation in Paris wore Billy down, and he instructed his lawyer to sell for $2 million. Bugsy’s lawyers countered at $300,000, and Billy came back at $1 million. The final offer from Bugsy was $600,000. Billy didn’t want to accept, but he didn’t want to die either, so he accepted the deal. On March 19, 1947, Billy signed the deal for a $300,000 initial payment with the remainder to be paid in August.

With the deal done, Billy returned to Hollywood in March. Within days, he got a call saying there was a contract to kill him. Within 48 hours, Billy was back in Paris.

The Flamingo reopened in March 1947, the same month Billy had planned for initially. Bugsy asked his investors for more time, and the property even generated a surprise profit in May. But it was too late. Bugsy’s credibility with the investor group was damaged beyond repair. In late May 1947, Billy was about to return to Hollywood when his office got an anonymous call warning him to stay in Paris until everything was over. On June 21, 1947, Billy opened the newspaper to learn that Bugsy had been murdered. He returned to Hollywood on June 23, 1947. His partnership with Bugsy was over.

Minutes after the shooting that killed Bugsy, Gus Greenbaum and Moe Sedway took control of the Flamingo. They changed some things to make it appeal to more people—not just to people with huge budgets. In the first year of their management, the Flamingo turned a $4 million profit.

Billy’s vision for Las Vegas was surpassed, to his astonishment. Developers took Billy’s vision to new heights and transformed the sleepy desert city into a luxury gambling mecca. The stretch of land outside of town where Billy started became the famous Las Vegas strip. Even though his vision for the Flamingo and Las Vegas became reality, Billy never spent a night in the Flamingo. In fact, he gave up gambling cold turkey when his son was born in October 1951. After six decades, becoming a family man gave Billy the strength and purpose to kick his gambling addiction.

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William Richard “Billy” Wilkerson had a policy of working with the best people. According to the biography of his life, sometimes that meant working with gangsters. During Prohibition in the 1920s, Billy ran several speakeasies for New York City Mayor James “Jimmy” Walker and later owned several himself in the city. Billy relied on gangsters to supply his liquor because they were the best.

In 1942, Ben “Bugsy” Siegel had murder charges against him dismissed after witnesses died during his trial. Bugsy was from New York City and well respected in organized crime circles, but he was known for being short-tempered. He moved to Hollywood to go legitimate and become a movie star, but his ego got in the way. Instead, he became a playboy and made money in familiar illegal ways.

Myer Lansky and Bugsy were close, and Lansky ordered Bugsy to explore expanding organized crime gambling activities in Nevada. Bugsy hated the desert and the extreme heat and stayed in Beverly Hills. He turned his responsibilities over to Moe Sedway. But when Lansky pressured Bugsy to oversee the investment group’s Flamingo Hotel investment and Billy Wilkerson, Bugsy reluctantly agreed.

Billy was shocked that Bugsy was his partner, but he made the best of it and mentored Bugsy. He even had his service providers sit with Bugsy to fill his knowledge gaps regarding all aspects of the project. Bugsy was glad to learn and worked to win Billy over. He was in awe of Billy’s visionary and business skills and tried to emulate him.

It wasn’t long before Bugsy became jealous of Billy’s talents. He contradicted Billy’s decisions behind his back and told people the Flamingo idea was his, not Billy’s. He demanded more of a hands-on role. Billy didn’t want that, but he gave in to keep the project moving. Bugsy would manage the hotel portion; Billy would manage everything else.

Bugsy went crazy spending and, within one month, spent the entire budget for the hotel and demanded more money. Billy was alarmed and realized that Bugsy could be stopped only by the investor group, but they refused to rein him in.

Bugsy demanded control of the entire project and talked the investor group into this, but he promised that Billy would have creative control and manage the operation when it opened. In reality, Bugsy wanted to destroy Billy, and Billy started to realize this as he witnessed Bugsy’s irrational behavior and outbursts. To get complete control, Bugsy bought creative participation from Billy by giving him an extra 5% ownership stake in the project. In June 1946, Bugsy formed the Nevada Project Corporation of California and named himself president and the largest principal owner. Everyone else—including Billy—was listed as merely a shareholder.

With Billy entirely out of the picture, Bugsy went on a spending spree. It was clear to everyone except Bugsy that he didn’t know what he was doing. His changes added to the project costs and forced him to raise more money from investors.

Bugsy still wasn’t happy because Billy owned 100% of the land. He offered to buy the land, and they struck two deals in 1946 that resulted in Billy getting an extra 10% ownership in the project in exchange for the land. Billy owned 48% of the project.

Costs kept increasing, and by October 1946, the project cost was over $4 million—four times the original budget. Investors were upset and asked for a full accounting of the project—and said that if they didn’t get it, there would be no future funding. Bugsy got a loan for $600,000 from Valley National Bank in Phoenix and started raising cash by selling nonexistent stock in the project. With pressure mounting, Bugsy planned to open the hotel early during Christmas 1946, even though the hotel rooms wouldn’t be ready. He was hoping gambling profits would help him pay back investors and buy him more time. Billy knew that Hollywood’s elite didn’t travel during the Christmas holidays and that opening without hotel rooms was a death wish.

When Billy shared his views, Bugsy didn’t listen; in fact, he exploded. That would come back to haunt him.

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By the end of 1944, William Richard “Billy” Wilkerson sought ways to gamble legally without incurring personal losses. According to the biography of his life, he looked hard at Las Vegas because Nevada was the only state with legal gambling at the time. The extreme desert heat and seclusion initially turned him off, but he realized the location was perfect for limiting distractions to gamblers. In December 1944, he leased the El Rancho Vegas for six months for $50,000, but he had bigger plans. He wanted gambling to be an elegant experience as it was in Europe, not a rustic experience as it was in the few casinos in Las Vegas at that time.

In January 1945, Billy purchased thirty-three acres several miles outside the city for $84,000. People thought he’d made a mistake, but Billy knew he couldn’t get that much land in the town and wanted to avoid competing with existing casinos.

In February, Billy started putting his vision on paper and hired architects. He wanted to build an oasis that would be heaven for gamblers and a relaxing spot for non-gamblers. He envisioned it as a luxurious vacation destination with a casino, showroom, nightclub, hotel, restaurants, health club, and more. He wanted his project to resemble European luxury and rival a Monte Carlo casino, with black-tie evening attire. Billy leaned on his gambling addiction to create the perfect gambling environment—including no windows so gamblers wouldn’t be distracted by sunlight. Most importantly, his project would be the first hotel in the United States to offer air conditioning, making the desert comfortable for the rich and famous patrons he wanted to target. Billy loved birds, so he named his project the Flamingo Hotel after the beautiful pink birds he’d seen on a trip to Florida.

Billy didn’t know how to run a gambling operation, so he hired Gus Greenbaum and Moe Sedway, who were overseeing lucrative gaming operations at the El Cortez Hotel. Both got good at running gambling operations by doing it illegally as bookmakers. They became silent partners and assumed responsibility for gaming, including staffing and permits.

With plans complete, the project was budgeted at $1.2 million, money Billy didn’t have. Bank of America reluctantly agreed to finance $600,000, and Howard Hughes loaned Billy $200,000. Billy decided to gamble with $200,000 to get the rest but lost it all. Frustrated by this and his continuing gambling losses of up to $10,000 a day, Billy erratically bowed out of the project and signed the land deed over to Sedway in September 1945 to settle a debt.

After seeing what Billy had done with Arrowhead Springs, Joseph Schenck believed in his vision for The Flamingo and convinced Billy to keep pursuing the project. Billy listened and bought the land back from Sedway. In November 1945, construction started, but post-war, materials were scarce and expensive, so the inflated costs exceeded Billy’s budget. The project was 33% complete and Billy had $300,000 invested and not enough to finish. He bet $150,000 of his last $200,000 to make quick money to keep the project going. He lost it all. In January 1946, construction was halted.

In February, a well-dressed businessman from the East Coast named G. Harry Rothberg offered Billy a $1 million investment for a 66% stake in his project. Billy would remain the operator and manager, and Rothberg’s investment group would be silent partners. Billy wouldn’t have to put any more of his own money into the project. Billy was intrigued. He didn’t like having partners, but investors who stayed out of the way he could live with. He negotiated to retain 100% ownership of the land and closed the deal.

After Billy received the funds, Sedway and Greenbaum introduced Billy to his new partner, Ben Siegel, better known as Bugsy Siegel. Billy didn’t know it then, but things would never be the same.

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