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’m trying to enhance a large language model (LLM) with specific information using retrieval-augmented generation (RAG). I’m not technical, so I’ve struggled with this.

What I learned:

• I probably can use a combination of a book scanner and an LLM to create a large percentage of a book digest.
• Creating a record (e.g., digest, profile, or something else) for each entrepreneur and enriching it with information from various books is likely the best approach to creating the best data set about entrepreneurs. But there’s a step beyond this I need to figure out.
• ChatGPT’s custom GPTs are helpful, but they have many limitations, and getting the prompting right requires extensive testing.

Those are my struggles and learnings from the week!

This year, I’ve read roughly twenty biographies and autobiographies about entrepreneurs in media—broadcasting, publishing, and cable. I didn’t plan to read so many books about this industry; it just happened as I followed my curiosity. As I read about one entrepreneur, I learned about competitors or business partners I wasn’t familiar with, so I found books on them too. Almost every book led me to at least one other person I wanted to learn more about.

Before I read all these books, I had zero understanding of media. I didn’t know its history, how people made money, or how it has impacted other industries and society. Now, I’m far from a media expert, but I have a working, high-level understanding of the industry and the strategies used to build large media companies. Reading books about numerous entrepreneurs back to back (mostly) helped me see the industry from different perspectives by way of each entrepreneur’s journey. This gave me a clearer picture of the industry and an understanding I wouldn’t have if I’d read about only one or two media entrepreneurs.

I gained lots of value from this media deep dive, and I want to mimic it in the future, but more intentionally. Next time, I’ll do a few things differently. The main thing is to start with a desire to understand a specific industry—and a clear reason why. Ideally, I’d be highly motivated to understand the industry to help me solve a specific problem. The other thing is to research the major players who helped create the industry and try to find books about them. Entrepreneurs who help build an industry in the early days and achieved outsize success are likely to have done business with, employed, or be connected to other entrepreneurs in the space.

Reading the life stories of multiple entrepreneurs in an industry feels like a major hack. I can’t wait to find out what the benefits are when I’ve studied several industries this way.

For the last few months, I’ve been creating a digest for each book I finish reading. Doing this has many pros, but the significant time it takes has been too big of a con. I started searching for ways to do it more efficiently. Many of the books I read don’t have digital or e‑book versions, and I decided to start with this, the most difficult use case.

I discovered that digitization of printed material is a known problem, and various solutions are available. The solution I’m most impressed with is scanners designed specifically for books. A few companies, such as ScanSnap and Czur, have products that do a great job. Some people have reviewed these products and publicly posted the digital books they created with them (see here, for example). Some people have even gone to the trouble of building homemade book scanners (see here).

I’m going to try to find one of these scanners to test locally. I want to see for myself how good a job they do and whether the digital files they create are searchable. If they pass that test, I’ll move to the next step in creating book digests more efficiently.

Last week, I finished reading Roy Thomson’s autobiography, the second book I’ve read about him in the last month. I found another biography about him, and I’m considering reading that, too. Last month, I read a biography about Felix Dennis, the second book I’d read about him.

I initially resisted reading more than one book about an entrepreneur, but I don’t feel that way anymore. Some material may be repetitive, but subsequent books usually contain new information too. Multiple books provide multiple perspectives on an entrepreneur’s life and get closer to a 360-degree view of that person’s journey. Reading too many books about a person would yield diminishing returns, but right now, my gut tells me that two or three books about a person is likely a good number.

I’ve also changed my thinking about how I record information about entrepreneurs I’m studying. Before, I thought in terms of books. Each book was an individual record, and I created a digest for each book. This meant I could have multiple digests about a single person. But now I’m thinking in terms of people. I need to consider how I want to capture the information. Ultimately, I want to do more than create blog posts and podcasts with these digests. Do I create one digest per person and add information from multiple books? Do I keep creating one digest per book? Or do I do something completely different?

I’ll be thinking about this question more and getting perspectives from people with relevant data management experience. In the meantime, I might experiment with my digest and blog post formats a bit.

I published a six-part podcast series on Ted Turner, the visionary entrepreneur who created CNN and other cable channels like Cartoon Network and TNT under Turner Broadcasting System. He also owned the NBA’s Atlanta Hawks and MLB’s Atlanta Braves, and had a fortune of $10 billion at its peak. I really enjoyed his autobiography and learned a lot from it. If you're interested in learning more about Ted and his remarkable journey, you can start listening to part one in this series on Apple Podcasts here or Spotify here. Ted's journey is covered in episodes 98 through 103.

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

Cumulative metrics (since 4/1/24):

• Total books read: 28
• Total book digests created: 12
• Total blog posts published: 154
• Total audio recordings published: 103
• Average digest length: 5.69% of the book’s length
• Average recording length: TBD

This week’s metrics:

• Books read: 1
• Book digests created: 1
• Blog posts published: 7
• Audio recordings published: 6
• This week’s digest length: 7.28% of the book’s length
• This week’s recording length: 17 minutes

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

• Read Roy Thomson's autobiography
• Finished creating a digest of the biography of Jack Kent Cooke
• Had one additional feedback session
• Edited and published an audio podcast series about Ted Turner’s autobiography

Content changes:

• Tweaked the introduction to the podcast a bit

What I’ll do next week:

• Read Claude Hopkins’s autobiography
• Write and publish blog posts about Roy Thomson’s autobiography
• Create a GPT using one of my book digests

Asks:

• Introductions to developers with deep experience in AI large-language models or working with big, unstructured data sets

Week two hundred thirty-two 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:

• No notable struggles this past week

What I learned:

• “What would they do in my situation?” is a question entrepreneurs always ask themselves when they’re learning about or speaking with other entrepreneurs. Entrepreneurs are constantly trying to determine what actions they should take to solve business problems.
• The blog posts and podcasts were helpful in the early part of this project. My energy shifted as I realized they’re ways to share the information I’ve compiled on entrepreneurs. I’m more excited about compiling information on entrepreneurs and figuring out how to make it easy for others to use it.
• I’ve been conducting feedback sessions on the podcasts I’ve created. They’ve been really helpful, but because of my shift in focus, I don’t need to do them as frequently.
• If you want to build an app, you can verbally describe what you want and AI can write the code for you.
• ChatGPT has a privacy setting that prevents it from training its models on content you upload to ChatGPT. You can make this and other privacy requests here.

Those are my struggles and learnings from the week!

I finished reading the biography about Jack Kent Cooke. The book detailed Jack’s journey from high school dropout to billionaire entrepreneur and sports mogul.

How Did Jack’s Early Years Affect His Trajectory?

Jack bet on himself early in life. He dropped out of high school and turned down a college scholarship to play hockey. Instead of pursuing education, he tried many things—and failed at most of them. He ended up going broke, and he and his wife had to move in with his parents. He didn’t give up, though. He picked himself up and kept trying. Experiencing failure and hitting rock bottom at a young age transformed Jack. From that point forward, he was no longer afraid of failure. And he realized he could outwork everyone else to increase his chances of success. With a fearless mindset and a dogged work ethic, Jack positioned himself to conquer almost any challenge.

What Strategy Did Jack Employ to Achieve Success?

Jack was a content master. He had a superior understanding of how people wanted to be entertained in their leisure time and knew how to create or acquire content that captured people’s attention. He started by creating programming for radio stations but eventually moved into magazines, newspapers, and professional sports. The type of content Jack focused on shifted, but the goal was always the same: provide people with something that captured their attention. Once Jack had captured an audience’s attention, advertisers paid him handsomely to make his audience aware of what they were selling.

Jack also understood the importance of distribution. He didn’t just want to create or buy content; he also owned content distribution mechanisms. He started with radio stations but eventually made a fortune in cable systems. The genius in Jack’s distribution strategy was that he preferred to own distribution mechanisms in areas where he could have a monopoly or where the barrier to entry was extremely high. This limited his competition and kept his margins high.

This isn’t unique to Jack, but he used leverage strategically throughout his career to acquire assets and build his empire. He also got extremely lucky when the S&L crisis allowed him to buy back, from the government agency that took over the S&Ls, hundreds of millions in bond debt issued a few years earlier for pennies on the dollar.

Jack achieved outsize success despite humble beginnings. But his health and relationships suffered because of how he went about achieving success. Anyone interested in publishing, broadcasting, professional sports teams, or the early days of cable could benefit from reading this book about Jack’s life.

According to the biography about Jack Kent Cooke, while he was still recovering from his heart attack in October 1973, Jack flew to New York to install himself as CEO of TelePrompTer Corporation to save the company. The stock price suffered after the CEO, Irving Berlin Kahn, was convicted of bribery. Jack’s stock in the company fell in value from roughly $50 million to less than $2 million, stirring Jack to action. Jack split his time between running his sports empire in Los Angeles and TelePrompTer in New York City. He cut 25% of the cable operator’s staff and stopped expanding into new areas. Over time, he was able to get the company back on solid footing.

At the same time, Jack was making winning championships a priority. In 1968, he signed superstar Wilt Chamberlain to the biggest NBA contract ever: $250,000 a year for four years. The Lakers won a championship in 1972. In 1975, he acquired superstar Kareem Abdul Jabbar in a trade. Jack ultimately drafted Earvin “Magic” Johnson in the 1979 draft and set the Lakers up for a decade of dominance.

His sports teams were doing well, but his marriage to Jean was falling apart, and in 1976, she tried to commit suicide again and left him. A contentious divorce and asset-separation process ensued. The divorce was finalized in 1977, but the division of assets wasn’t finalized until March 1979 after Jack’s underhanded tactics to hide information from Jean came to light. After over forty years of marriage, their assets were spilt as follows:

• Jean received their $1 million Bel-Air home, $24 million in TelePrompTer shares, and 28% ownership in Raljon Corporation, an entity that owned the Los Angeles Kings NHL team, the Los Angeles Lakers team, the Forum arena, the 13,000-acre Raljon ranch, and a videotape enterprise.
• Jack received a home in Las Vegas, all of his ownership in the Washington Redskins, and 72% ownership in Raljon Corporation.

Each of them received roughly $42 million in assets. It was the largest divorce settlement up to that point and was included in the Guinness Book of World Records. Three months later, in June 1979, Jack sold the Forum, the Kings, the Lakers, and Raljon Ranch to Jerry Buss for $67 million. The Buss family still owns the Lakers. Looking for a fresh start, Jack promptly moved to Washington, D.C., that summer to be closer to the NFL team of which he was the majority owner.

Jack owned 82% of the football team, and he put his stamp on the team. On the basis of his experience, the team leaned on ads and sponsorships to generate additional revenue. During his tenure as owner, he hired legendary coach Joe Gibbs, and the team appeared in three Super Bowls, winning two titles. The other owner of the team, until Jack bought him out in a contentious battle, was Edward Bennett Williams, an attorney and eventual owner of MLB’s Baltimore Orioles.

Jack also got into commercial real estate when the New York City market struggled. He bought the iconic Chrysler Building there for roughly $87 million in August 1979 from an insurance company that had foreclosed on the property. Jack finished their $58 million renovation project and added another $30 million to the budget. He refinanced his purchase in 1982 with an interest-only loan, paying $553,000 monthly at 10.5% interest on a $60.5 million loan. He refinanced again in 1987 for $250 million. The building was worth an estimated $550 million a decade after his purchase.

The 1980s were a busy time for Jack. He moved forward in his personal life and, in 1980, married Jean Maxwell Williams Wilson, but they divorced ten months later in 1981. In 1981 Jack sold TelePrompTer to Westinghouse for $650 million, netting himself over $70 million and a $4.65 million consulting contract. He won the bid to purchase Elmendorf Farm in Kentucky in 1984 for $43 million, using a controversial add-on bid. And in late 1985, he acquired the Los Angeles Daily News, paying the Chicago-based Tribune Company a whopping $176 million, or roughly twice what other bidders had offered for a paper generating $100 million in annual revenue and $12.5 million in annual profit. His biggest purchase was McCaw Communications, the twentieth-largest cable system with over 464,000 subscribers in forty-two communities. Jack paid roughly $1,800 per subscriber, or $755 million, for the company.

To finance all these deals, he used leverage. He did what everyone else was doing at that time: he used junk bonds to raise capital. In April 1987, he hired Michael Milken of Drexel Burnham, and a $951 million bond offering was completed. Jack used most of the proceeds to pay for the McCaw purchase and to refinance debt on and enhance operations at the Los Angeles Daily News. Jack wasn’t done. In 1987, he bought First Carolina Communications, a cable system with 156,000 subscribers. Jack paid $1,900 per subscriber, or $300 million.

In 1989, Jack decided to cash in. He exited the cable business for good in grandiose fashion. He sold all his cable holdings for a staggering $1.6 billion, or $2,300 per subscriber, likely making himself a roughly $400 million profit. With this deal complete, Jack liked to remind people that he’d become a billionaire. This was a rare accomplishment in the 1980s and early 1990s, even among the fraternity of NFL owners that Jack was part of.

Between 1987 and 1990, Jack married two more women and had a daughter by one of them. Both marriages were messy, making the pages of Washington, D.C., newspapers, and are detailed in the biography. At the time the book was published in 1992, Jack was still alive and running his sprawling empire. He passed away in 1997 at the age of 84.

Jack was a wildly successful entrepreneur whose gift of deeply understanding how people wanted to spend their leisure time allowed him to build sports, cable, and publishing empires.

In 1959, before becoming a U.S. citizen, Jack Kent Cooke purchased an AM radio station in Pasadena, California, for $900,000 in his brother’s name.  In 1960, a contest the station ran caused an FCC investigation that uncovered Jack’s majority ownership. In 1962, the FCC ordered the station shut down, and Jack lost the license. It was a major financial blow. While he was licking his wounds, Jack stayed in a remote California hotel. He was surprised to get clear television reception. He learned the hotel was wired for CATV—cable TV—and that people were paying $5 a month for the service. Jack immediately recognized the potential of cable TV and jumped into action.

Cable was simple then, just a way to bring six or so channels to a community from broadcast networks that didn’t have strong enough signals. In the fall of 1964, Jack made his first cable TV antenna system investment for $4.6 million. The profit potential of a protected cable franchise was obvious and reminded him of the early days in northern Ontario when Roy Thomson had a license to print money in broadcast radio. The formula was simple to Jack. Current customers plus projected growth of a cable system’s coverage combined with current and future subscriber rates told you how much each system could generate in revenue. Having calculated these figures, Jack paid $300 per cable subscriber when he purchased a cable system. With customers paying $5 monthly, one deal was netting Jack $80,000 in monthly cash flow. Jack named his company American Cablevision.

Jack’s broadcasting and publishing background gave him an advantage in understanding the potential of the cable market. He moved fast and, in 1965, added tons of communities to his coverage area by buying existing franchises in rural areas. He created two subsidiaries, too—one that “engineered other CATV systems” and one that sold cable equipment. Jack built American Cablevision to 85,000 subscribers and, in 1968, merged it with H&B Communications in a stock deal valued at $30.8 million. In 1970, H&B was bought by TelePrompTer Corporation, then the largest cable system in America, in a stock deal. After the acquisition, Jack owned almost 12% of TelePrompTer’s publicly traded stock, meaning Jack’s shares were worth roughly $40 million. In about five years, Jack had created a $40 million cable fortune.

Cable wasn’t enough for Jack, and in 1965, he purchased the NBA’s Los Angeles Lakers basketball team for $5,175,000, a record price. Jack viewed a team in Los Angeles as one of the three most valuable NBA properties, teams in Boston and New York being the other two. Jack was also gunning for the rights to start an NHL expansion team and thought owning the Lakers and having partial ownership of an NFL team legitimized him as a sports mogul. He was right. Less than a year after purchasing the Lakers, he was granted rights to Los Angeles’ expansion NHL team for a $2 million fee and a promise to play in an arena that seated at least 12,500 people. Jack also paid $250,000 for the right to have a team in the United Soccer Association.

Jack kept pushing and, in 1966, added real estate to the mix. He started building the Forum, a modern, roughly $17 million sports arena in Los Angeles that his basketball and hockey teams could play in. The arena opened in 1967 and was unlike anything anyone had ever seen. It was a huge success.

While Jack was thriving as a sports entrepreneur and also running other enterprises, his health and home life were suffering. In 1965, his wife Jean was unhappy and attempted suicide for the first time. And Jack’s brutal work schedule led to him having a heart attack in 1973. This slowed Jack down, but it didn’t stop him. He was just getting started and was focused on his teams becoming champions.