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: 119 (+7)
• Average recording: no recordings this past week

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

• Read the autobiography of Ted Turner, founder of CNN, TBS, and TNT
• Had three additional feedback sessions
• Compiled and sorted feedback from sessions completed the week of 7/15/24

Content:

• No recordings this past week

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-six was another week of learning. Looking forward to next week!

Prefer listening? Catch audio versions of these blog posts, with more context added, on Apple Podcasts here or Spotify here!

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:

• I struggled to create the upcoming series on Felix Dennis. The problem was that the biography focused deeply on Dennis’s personal side and was surface level on his career as an entrepreneur. I had a hard time creating a series about his entrepreneurial journey that satisfied my curiosity and met my expectations.

What I learned:

• I’m getting comfortable with the quality of the content. Before, I wasn’t happy with the preceding week’s work, but I knew I was getting better. I’m still not satisfied with the quality, but it’s good enough that I’m comfortable sharing it outside my immediate circle.
• Reaching out to people individually to make them aware that a series was published had a material impact on the number of listens for the John H. Johnson series. This won’t scale, but I want to do this strategically going forward.
• Don't read books that don’t resonate with me after fifty pages. If the first fifty pages don’t discuss what I care about in someone’s journey, the rest of the book won’t either. I knew this already, but I didn’t follow it for the Felix Dennis biography.
• When I’m picking which book to read for the week, I should factor in the book’s quality or story. I’ve been weighing the length of the book too heavily. A shorter book takes me longer to read if I’m not into it.

Those are my struggles and learnings from the week!

Prefer listening? Catch audio versions of these blog posts, with more context added, on Apple Podcasts here or Spotify here!

I finished reading more about Felix Dennis. The first book I read about him, which he wrote, detailed his thoughts on how to succeed as an entrepreneur. The second, a biography, described his journey from his early years through his passing at age 67 in 2014. The latter book contained less detail about Felix’s entrepreneurial journey than I’d hoped, but I still learned some new things about him.

How Did Dennis’s Early Years Affect His Trajectory?

His parents’ dynamic had a big impact on Dennis. His father leaving when Dennis was four put pressure on his mother to provide for her sons. Working as a bookkeeper, she realized a career in accounting could be her savior. She became laser-focused on becoming an accountant so she could provide. The positive was that Dennis saw work ethic and focus pay off for his mother. But her sons were neglected and didn’t get much, or any, motherly warmth from her. Felix followed in his mother’s footsteps: he was laser-focused on his goals and outworked everyone else to make them happen.

His parents struggled to keep their general store open, and his mother struggled as the sole provider. There wasn’t a lot of money, and at one point, Dennis’s living arrangements included an outside toilet and no electricity. Dennis was determined never to live like that again. “Under no circumstances would I stay poor,” he wrote. His determination fueled his pursuit of financial freedom.

Felix was in his early twenties when the Oz trial ordeal began. It was a rude awakening to how the world really works and how unfairly the establishment treats certain people. He decided he needed money to put himself on a fairer playing field with the establishment and to make it possible to defend himself if necessary. This realization about money was another factor that fueled his pursuit of financial freedom.

How Did Dennis Become So Successful?

The Oz trial had a significant impact on British society. It made Dennis an icon and gave him an edge, especially in the publishing world. This standing opened doors for him and allowed him to make several critical deals. His name alone would get him meetings with people or allow him to steal deals that competitors considered won but that weren’t closed.

Dennis was a master at identifying market gaps and filling them with something people would love. He was highly gifted at being in tune with what people wanted. He had a deep understanding of how customers thought and how to create publications that resonated with them. He was what the venture capital world would call a hipster and played this role repeatedly, especially in his partnership with Peter Godfrey and Bob Bartner. Maxim's outsize international success was a result of Dennis’s hipster abilities.

Felix was also an unapologetic opportunist who had a keen sense for markets that were severely underserved or would be underserved because they would grow rapidly.

Another contributor to his success was that he didn’t have a wife or children, so he could work longer hours and take bigger risks without worrying about the impact on his family.

Dennis was gifted with words. He knew how to talk to people in a way that resonated deeply with them. He made everyone he conversed with feel like they were the only thing that mattered. He mesmerized people when he spoke with them. This made him a superior salesman who could close almost any business deal. It also made him a gifted poet and womanizer.

What Kind of Entrepreneur Was Dennis?

Dennis was a founder. Most of the businesses he was involved in started from nothing. As his empire and resources grew, he bought some publications, too.

Dennis believed that making money was a skill. He applied it to publishing, but he believed he could have applied it to any industry and done well. His confidence in his moneymaking skill led him to take risks that others wouldn’t dare take.

Dennis was also a marketing genius. He instinctively knew how to get and keep people’s attention. This served him well in publishing because attention was what he sold to advertisers.

Dennis was a colorful entrepreneur who changed publishing in the UK and the United States. I’m still curious about some aspects of his journey and will be reading more about him.

Prefer listening? Catch audio versions of these blog posts, with more context added, on Apple Podcasts here or Spotify here!

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.

Prefer listening? Catch audio versions of these blog posts, with more context added, on Apple Podcasts here or Spotify here!

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.

Prefer listening? Catch audio versions of these blog posts, with more context added, on Apple Podcasts here or Spotify here!

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.

Prefer listening? Catch audio versions of these blog posts, with more context added, on Apple Podcasts here or Spotify here!

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.

Prefer listening? Catch audio versions of these blog posts, with more context added, on Apple Podcasts here or Spotify here!

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!

Prefer listening? Catch audio versions of these blog posts, with more context added, on Apple Podcasts here or Spotify here!

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!

Prefer listening? Catch audio versions of these blog posts, with more context added, on Apple Podcasts here or Spotify here!

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.

Prefer listening? Catch audio versions of these blog posts, with more context added, on Apple Podcasts here or Spotify here!