Every week, I post an update of what I’m working on and what I’ve accomplished. I’ve been doing some form of this weekly update for several years. Yesterday, I realized that I forgot to do an update for the week ending September 28, 2025. So, I published that week’s update today. You can see it here.

I still need to share an update of last week (week ending October 5), and I plan to publish it before the weekend. That means you’ll see two weekly updates in the span of a few days. It’s not a mistake; it’s intentional (kinda). Hopefully this makes sense.

Current Project: Reading books about entrepreneurs and sharing what I learned from them

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: 82
• Total blog posts published: 539

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed this week ending 9/28/25 (link to last week’s commitments):

• Read Positioning, a framework for thinking about perception and using it to own a position in the customer’s mind from a marketing perspective
• Added four more books to the library on this site—see more here; these, which I read in 2018 and 2017, were about financial crisis winners, open-book management, and mental clarity

What I’ll do next week:

• Read a biography, autobiography, or framework book
• Add four more books that I read before 2024 to the library on this site—see more here

Asks:

• No ask this week

Week two hundred eighty-seven was another week of learning. Looking forward to next week!

Current Project: Reading books about entrepreneurs and sharing what I learned from them

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 last week

What I learned:

• Last week I shared what I learned about Pipecat and Livekit, two open-source orchestration frameworks that can be used to build real-time voice and multimodal AI agents (see here). This week I learned about turn detection: “determining when a user begins or ends their ‘turn’ in a conversation.” Turn detection makes for polite AI conversations—AI and the user don’t talk over each other because the AI waits until the person is done before it speaks.
• The best conversations between entrepreneurs aren’t polite. They’re high-energy. Ideas are shared rapid fire. One entrepreneur’s idea sparks more ideas from the other. They interrupt each other. They talk over one another. These types of conversations, replicated using the above frameworks and paired with a library of knowledge from biographies and other books, could lead to entrepreneurs having great thinking or sparring sessions with AI.

That’s what I learned and struggled with last week.

In 2024, I challenged myself to accelerate my learning by reading a book (usually a biography) a week. To date, I’ve done it for 82 consecutive weeks. I wanted to share what I was reading and also keep track for myself, which was difficult (see here), so I created a Library section on this site. I added to it all the books I’ve read since my book-a-week habit began in March 2024, and I’ve committed to adding my latest read to the Library every Sunday (see the latest here).

That left the books I’d read before 2024 unshared and untracked. I set a goal to add my old reading to the Library over time. It began with a Memorial Day Challenge to add five books (see here) and continued with my challenging myself to add two books every weekend until my backlog is gone. This month (see here), I decided to up the pace so I can finish this project well before the holidays—and begin another one!

This past weekend was my eighteenth weekend, and I added five more books:

• Principles by Ray Dalio
• Den of Thieves by James B. Stewart
• When Genius Failed by Roger Lowenstein
• Margin of Safety by Seth A. Klarman
• King of Capital by David Carey and John E. Morris

That’s the latest update on my weekend goal. I hope that sharing these books will be of value.

Last week I shared the 22 timeless principles of marketing that I learned from Al Ries and Jack Trout’s book (see here). I enjoyed that book and wanted to learn more, especially about positioning (i.e., perception), so I read their book Positioning, which focuses on how to get noticed and be perceived in the way you’re trying to be perceived.

This book came out in 1981. Ries and Trout argued that positioning was a new way of communicating that works well for advertising, politics, and other areas. “Positioning is what you do to the mind of the prospect,” they said. “That is, you position the product in the mind of the prospect.” It’s a way for companies, products, or services to be heard and seen in a world full of ads.

My key takeaway is that positioning focuses on leveraging what’s already in someone’s mind (instead of trying to introduce a new idea). You begin by concentrating on people’s perceptions and work backward to figure out how to message in a way that aligns with what they already think (this is the opposite of how most people approach marketing). Positioning “manipulates what’s already up there in the mind, to retie the connections that already exist.” It leverages the fact that people are bombarded with so much information that they discard most of it unless it matches their existing knowledge or experience. Don’t try to jam something new into someone’s mind; reconfigure what’s already there.

The book went further, saying that oversimplifying is the key to being received and you should focus on being narrow and selective with your messaging.

The book has 23 chapters, each dedicated to a distinct aspect of the positioning strategy. Several case studies in each chapter support the concept being covered.

Marketing is foreign to me, but this book, combined with The 22 Immutable Laws of Marketing, was helpful. They lay out the principles and strategies of marketing, which I never understood. When I view certain marketing tactics through the lens of what’s in these books, things make a lot more sense.

If you want to learn how to get people to think about something in a certain way, consider reading Positioning.

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I’m making great progress on my weekend project. I estimate that if I add four to five books each weekend for the next three weekends, I should complete this project by the end of the third weekend. I’m excited to wrap this up and share my complete library with others. I really hope people find it helpful. I haven’t seen anything like this that caters to entrepreneurs or investors.

Now I have to narrow down my list of potential projects and pick the weekend project I want to work on for the next few months. I also need to figure out what the optimal length of time is for these weekend projects. This one will have taken about five months by the time it’s done. I feel like that might be too long. My gut tells me that something in the three- to four-month range is about right. That way, I can complete three or four weekend projects a year. I’ll think more about this over the weekend.

This week, I had a conversation with an entrepreneur who’s considering closing his business. The business breaks even or runs at a slight loss most months. When someone is considering closing a business, I wonder why, so I asked.

This entrepreneur has had his business for about a decade. He’s no longer excited by it and hates the thought of going back to being involved in its day-to-day operations. He’d rather spend his time on new entrepreneurial pursuits, which he’s already doing. This makes sense to me. Around the decade mark with my company, I began to lose enthusiasm and remove myself from certain aspects of the operations. I’ve heard other entrepreneurs share similar experiences.

Next, I wanted to understand the issue with the business. Why wasn’t it generating a profit? Operationally, it’s running smoothly with a small team. The work gets done as expected and customers are happy. But they’re not getting enough customers through the door to generate the revenue needed to turn a profit. I asked how they acquire customers and let customers know they exist. It turned out that the entrepreneur hasn’t done any marketing in a few years. He did big marketing pushes years ago, which were successful, and he’s been coasting on word of mouth ever since. But word of mouth is dwindling, and the result is fewer customers.

Marketing is just like other business functions, with one important difference. When you stop operations, you notice immediately because the work isn’t getting done and customers are mad. When you stop marketing, you often don’t see the impact right away. Awareness of your business gradually declines. Revenue gradually declines. One day, you realize you don’t have enough business.

I told this entrepreneur that it seems like he’s got a marketing issue. If he can dedicate himself to a few months of restarting his marketing function and incorporating metrics that quantify his return on marketing spend, he’ll likely see a profit again in a few months. Instead of closing the business, he’ll have a good shot at getting marketing running smoothly without him—just like the rest of the business—and then selling the business. Instead of getting nothing and walking away, he may be able to sell it, get a nice chunk of change, and pursue his new entrepreneurial ideas with a clear mind and capital to fund them.

Today I read an article (see here) about James Dyson’s annual dividend from the namesake company he founded decades ago. He reportedly owns 100% of the firm and received a 2024 dividend of $303 million (converted from British pounds). He received a $1.5 billion dividend in 2022, and over the last four years he’s received a total of roughly $5.39 billion. That’s an astonishing amount considering that he still owns his company, Dyson, outright, and that ownership is worth well over $10 billion.

I read Dyson’s autobiography last year (see here), so I know that his journey to building his company was anything but smooth. What stands out to me is that after all these years, he hasn’t sold it. He created and continues to own a valuable asset that generates substantial annual dividends, which he invests in diversified assets.

That’s very unlike today’s entrepreneurial culture, which celebrates exits (i.e., selling a company). When you look at the entrepreneurs who’ve created the most wealth for themselves, they didn’t exit. They built great companies that are wildly profitable, and they continue to hold significant stakes in them.

As I added books that I read years ago to the library section of this site, I realized that I didn’t retain a lot of what I read. That makes sense, given that I read some of them seven years ago, in 2018. But I want to retain more of the important concepts and ideas in the books I read. I try to review my notes from books, but that hasn’t been effective because I haven’t been consistent and intentional about digging them up and reading them.

I’m starting to think that reviewing things I’ve learned by rereading them isn’t the best method. To read, I have to focus and not be doing anything else, which means carving out time to do it. That’s proven to be easier said than done.

I’m starting to think that although reading is a good way to introduce a new idea or concept to my brain because I’m focused and able to fully absorb it, it isn’t the best method for later review. Audio might be better. I can listen and do things at the same time, and I can easily fit that kind of multitasking into my schedule. The audio doesn’t have to be super in-depth—just enough information to spark my recollection of a concept.

I’ve been thinking about this more. I’ll try to test it to see if my hypothesis holds up.

In 2024, I challenged myself to accelerate my learning by reading a book (usually a biography) a week. To date, I’ve done it for 81 consecutive weeks. I wanted to share what I was reading and also keep track for myself, which was difficult (see here), so I created a Library section on this site. I added to it all the books I’ve read since my book-a-week habit began in March 2024, and I’ve committed to adding my latest read to the Library every Sunday (see the latest here).

That left the books I’d read before 2024 unshared and untracked. I set a goal to add my old reading to the Library over time. It began with a Memorial Day Challenge to add five books (see here) and continued with my challenging myself to add two books every weekend until my backlog is gone. This month (see here), I decided to up the pace so I can finish this project well before the holidays—and begin another one!

This past weekend was my seventeenth weekend, and I added four more books:

• The Big Short by Michael Lewis
• The Greatest Trade Ever by Gregory Zuckerman
• The Great Game of Business by Jack Stack and Bo Burlingham
• Declutter Your Mind by S.J. Scott and Barrie Davenport

That’s the latest update on my weekend goal. I hope that sharing these books will be of value.