Last week, I shared a post about Roy Thomson’s strategy for growing his media empire. It focused on cash flow. He bought small-town newspapers, many of them monopolies in their communities, that had strong cash flows. The newspapers were low to no growth in some cases but generated healthy cash. Roy then used those yearly cash flows to purchase more cash-flowing newspapers and other media assets.

I’m now reading Newhouse: All the Glitter, Power, & Glory of America's Richest Media Empire & the Secretive Man Behind It by Thomas Maier. It’s about Samuel “Si” Newhouse Jr. and his family’s media empire. This billionaire family owns numerous newspapers through Advance Publications and also owns Condé Nast, which publishes famous magazines like Vogue, Vanity Fair, GQ, and The New Yorker. Advance Publications owned 26.5% of Reddit when it began trading on the public stock market this year (see here, page 194). As of this writing, Reddit’s market capitalization (i.e., valuation) is just under $12 billion.

As I read more about Si and his family’s growth strategy for their media empire, I see that it’s similar to that of the Thomson family and others, including Warren Buffett and Mark Leonard of Constellation Software. The Newhouse family initially purchased cash-flowing newspapers and used the cash from those businesses to buy more businesses. They’ve done this over decades and built a sizable empire.

It’s notable that several people (and families) who’ve achieved outsize business success have used a similar strategy.

I’m curious to learn more about the Newhouse empire and family members, especially the patriarch, Samuel Irving Newhouse Sr.

A friend read my post about reading multiple biographies and autobiographies to understand an industry. He suggested that I also read books that explain how an industry works. His argument is that information in these books will fill gaps in my understanding of the industry that exist because everything isn’t covered in biographies. Reading both should give me a superior understanding.

I’m always open to trying new things, so I agreed to read a book on the media industry, given the biographies I’ve read recently. I’m going into this with an open mind, but I have some reservations. I learn best by hearing about the experiences of other people. If there’s no story, no personal journey, it may be harder for these books to keep my attention. We’ll see.

I’m excited to see if doing what my friend suggested resonates with me and leads to a better understanding of the media industry, or at least a subset of it.

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: 30
• Total book digests created: 12
• Total blog posts published: 168
• Total audio recordings published: 103

This week’s metrics:

• Books read: 1
• Book digests created: 0
• Blog posts published: 7
• Audio recordings published: 0

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

• Read biography about Roy Thomson and his son Kenneth Thomson
• Created first draft of a pitch deck
• Located commercial-grade book scanner in Atlanta
• Had one additional feedback session

What I’ll do next week:

• Read biography about Samuel “S.I.” Newhouse Jr.
• Continue tweaking the pitch deck
• Continue tweaking custom GPT

Asks:

• None

Week two hundred thirty-four 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 material struggles this week

What I learned:

• The more information you upload to ChatGPT’s custom GPTs, the more the quality of returns diminishes.
• Study groups (e.g., Bible study groups or book clubs) are valuable because they bring people together to share ideas about what they read. The varied interpretations and perspectives are helpful.
• Chronology is likely the best framework for a dataset that captures a person’s journey.

Those are my struggles and learnings from the week!

This week, I was asked several times about my personal project, so I took the opportunity to work on my pitch. A few learnings:

• Starting by describing the problem and the emotion it creates in entrepreneurs got people hooked. Then when I said I’m solving the problem, they wanted to talk more about their experience with it.
• Technically oriented founders dove deep into how to build the solution.
• Communicating the supply-and-demand dynamics around the problem helped people understand the size of the opportunity.
• Expressing the “why now” resonated with people.
• Shorter responses from me were better and led to a conversation about the problem and the solution.
• When I shared my vision, it missed the mark. I need to work on this.

Getting the pitch right is a process. The best time to start was yesterday. The more I pitch and work on my deck, the better it should get.

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.

‍

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