I had a good text exchange with a friend about my book project. It got me thinking. He said that because I’ve read so many biographies about entrepreneurs, in media at least, the wisdom is natively engrained in me and it will be hard for others to compete with me. Here are a few thoughts on this comment and our text conversation:

• I love it when people give me unsolicited feedback and ideas. It usually gets me thinking about things from a different perspective.
• Lots of entrepreneurs have read significantly more biographies about entrepreneurs than I have. True, I’ve done it at a rapid clip this year, but others have been doing it for years or decades and are far ahead of me. Consistent execution is the difference maker in something like this, especially when considering knowledge's compounding nature. If I can maintain this pace for years or decades, then I might have a shot at having an edge over others, but I’ve got a lot of ground to make up and I’m not doing it to get some title or prize. A big positive from this project is habit formation. I can comfortably read at least one book a week, and I think maintaining that pace for years is doable.
• To make something really stick in my brain, I have to do extra work. Reading doesn’t, by itself, ingrain in me the wisdom from an entrepreneur’s story. Creating the digest for a book forces me to understand their journey clearly and make connections (i.e., insights). Writing blog posts and creating a podcast series to share what I’ve learned forces me to get crystal clear on the strategies and ideas that propelled that entrepreneur. This entire process helps ingrain the wisdom and insights from each book. It’s time consuming, but it’s helpful. Doing it all manually isn’t sustainable, though.
• I don’t have a photographic memory. What I’ve learned is pretty fresh in my mind now, but to keep it at the forefront of my mind, I need to begin reviewing my highlights and digests regularly. Developing that habit will be painful—but a game changer, I suspect. Thirty minutes a day reviewing takeaways from biographies will be enough. I just need to cut out something that wastes thirty minutes a day to make room for this new habit.
• I want to lean into helping more entrepreneurs benefit from the valuable lessons in these biographies, but I don’t want to be the product. I want to share the information so others can use it as they see fit. I don’t want people to come to me to help them apply what I’ve read to their situation. I’m only one person, and that isn’t scalable. I want maximum impact; therefore, I can’t be the product. Figuring this out is top of mind.

Thanks to my buddy for initiating the text conversation that got me thinking!

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: 29
• Total book digests created: 12
• Total blog posts published: 161
• 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: 0
• Blog posts published: 7
• Audio recordings published: 0
• This week’s digest length: no digest this week
• This week’s recording length: no recording this week

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

• Read Claude Hopkins’s autobiography
• Had one additional feedback session
• Created first version of custom GPT in ChatGPT

Content changes:

• No changes this week

What I’ll do next week:

• Read biography about Roy Thomson and his son Kenneth Thomson
• Create draft of a pitch deck
• Continue tweaking custom GPT
• Find a commercial-grade book scanner in Atlanta

Asks:

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

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.