I had a conversation with an entrepreneur who’s an avid reader and history buff. He pointed out something that stuck with me: biographies and autobiographies about business founders are the most challenging historical books to write. He based that on a few insights:

• Authors who write about entrepreneurs aren’t entrepreneurs and don’t usually understand business. They focus on telling a compelling story and don’t deep dive into an entrepreneur’s actions or why they took them. This leaves entrepreneurs who read their book craving more details about some parts of the journey.
• Entrepreneurs who write autobiographies usually aren’t gifted writers. They know all the details about their journey, but putting it down on paper is challenging for many of them, and they need help. If they move forward with the book, many will get a coauthor to fill the gap.
• The more time that passes, the harder it is to piece together exactly what an entrepreneur did and why they did it. This isn’t as true of other historical events, such as wars.

The details of what an entrepreneur did and why they did it are what make a journey resonate with me and help me figure out how to apply it to my situation. When that’s missing from a biography, I tend not to enjoy it as much. My favorite books are autobiographies. Reading them is the closest you can come to getting inside an entrepreneur’s mind without talking to them. They usually include the nitty-gritty, reasoning, and emotions.

This entrepreneur made a great point today. I’m going to think about this more.

I’m reading The Thomson Empire by Susan Goldenberg. It’s a biography about Roy Thomson and his son Kenneth Thomson, but it also describes the inner workings of the Thomson empire and its reinvestment strategy through 1984, when the book was published. The books about Roy Thomson that I’ve already read, as well as this one, highlight Roy’s and his company’s focus on growth through acquisition.

Roy and his son heavily emphasized maintaining high profit margins and strong cash flows by tightly controlling costs. That was more important than revenue growth. In fact, they owned dozens of newspapers in small communities where they knew revenue-growth potential was limited but margins and cash flow could be favorable because they were the only paper in town.

Every acquisition of a company was based on its cash flow, not what it could be if they grew it. The Thomson empire typically used that cash flow to acquire more cash-flowing businesses. With this blueprint, they grew their company into a massive empire.

Other entrepreneurs, such as John Malone of TCI and Henry Singleton of Teledyne, have used this strategy. It works well and is the foundation of Warren Buffett’s strategy with Berkshire Hathaway.

The entrepreneurs I’ve read about who embraced this growth strategy weren’t customer focused. They weren’t obsessed with a customer’s problem. They didn’t aim to provide the best solution for a customer’s problem and grow by scaling the solution. They were okay with offering a decent or subpar solution if it provided the cash flow needed to acquire more companies. The result was the ownership and decentralized management of many companies. Some companies didn’t provide good products or services and didn’t have a good reputation with customers. Some did, and did have good reputations. But all of them generated good cash flow.

If growth is an entrepreneur’s goal, these examples highlight different ways to check that box:

• Solve a single problem well and scale it to as many people as possible
• Find businesses that generate cash and use it to buy more businesses
• Take a hybrid approach

The right approach depends on the entrepreneur.

Last week, I shared my updated thoughts on reading multiple biographies about one entrepreneur. Multiple books provide multiple perspectives on an entrepreneur’s experiences, which gets me closer to a 360-degree view of that person’s journey. From a data perspective, I’ve been thinking about the best way to capture an entrepreneur’s journey so it adds value to others.

Multiple books can be written about a person, so there’s a one-to-many relationship between people and books. Therefore, a data record needs to be created for each entrepreneur, and information from various books enhances that record with details about the entrepreneur’s journey.

So, what’s the best way to structure this record for each person? I talked with a few developer friends with experience working with large data sets. Among other ideas, most strongly suggested that I create a proprietary framework optimized for entrepreneurs and fit details from each person’s journey into it. I didn’t like that idea for various reasons, so I continued to ponder. I asked myself, what biographies are best and worst at communicating an entrepreneur’s journey? And why? I also looked for clues in the digests I’ve created.

I realized a few things. The biographies I gained the most from portrayed an entrepreneur’s life with a clear, chronological story. The hardest to digest were the ones with lots of jumping between different periods throughout the book. The person’s journey wasn’t clear, or I didn’t know where I was in the journey. One of my favorite entrepreneur autobiographies, and a highly regarded bestseller, is Shoe Dog: A Memoir by the Creator of Nike by Phil Knight. I read parts of it again and concluded that one reason so many entrepreneurs like this book is its concise chronology of the struggles Knight endured in Nike’s early years. The book makes sure the reader knows where they are in Knight’s journey by making the title of each chapter a calendar year in Knight’s life (e.g., 1966). Chronology was a key to communicating Knight’s journey effectively.

I read a few digests that I created about books. In each one, I structured the information with a chronological tilt. It wasn’t intentional, so it must have been the best way for me to make sense of and document an entrepreneur's journey. I was trying to create a timeline of the entrepreneur’s journey.

As I thought about this more, I got comfortable with the idea that time could be my framework. Everyone has a birth date and a death date. Their journey is everything that happens in between. People learn from other people’s journeys and the wisdom they gain along the way. I can enhance every entrepreneur’s record in my data set with events and actions at specific times to chronologically document their journey. Every biography or autobiography helps create a clearer picture.

I still have more thinking to do around this, but chronology as a framework resonates as a logical way to organize a data set of entrepreneurs’ journeys.

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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.