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 related to this project

What I learned:

• This is more of a personal realization than anything, but synthesizing what I read is key to enhancing my understanding of what I read.

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

Last year, I was creating a blog post series for each book I read. After reading a book, I had to go through all my notes and highlights to create a digest in the form of a Google doc that detailed, by chapter, all the important points in bullet format. The result was a summary of each book, by chapter. Most were between 5% and 10% of the book’s length, so for a 250-page book I’d have a Google doc of 12–25 pages. Creating a 12–25-page Google doc takes a ton of time.

I read a book a week, so I had to create these digests weekly. In addition, I was publishing a series of blog posts on each book and experimenting with podcasting by creating a series of episodes on each book. It all felt unsustainable, so I didn’t continue.

I’m reflecting on this today, and I realized a few things:

• Too many new things. Creating the podcast was a ton of effort. Creating the book digest was a ton of effort. Writing a blog post series was a ton of effort. Taking on all these new activities at once likely contributed to it feeling unsustainable. I was never able to find a “groove” for any of the three that felt like second nature. I was just trying to get through it all, but I never felt comfortable with any of it. In hindsight, I should have started with one, gotten that under my belt, and then moved to another.
• Synthesis enhanced my understanding. Creating those digests, which were the foundation for the blog post series, forced me to read analytically. Doing so led to a deeper understanding of what I was reading and helped me uncover more insights and achieve a level of retention I hadn’t experienced since college. When I stopped creating digests, I got less from the books I read. In retrospect, this step, which felt painful, was tremendously beneficial.
• AI can’t save me. I thought I could use AI to help me. My idea was that I could feed AI my highlights and notes from a book and it could create a digest for me. I now realize that this detracted from my understanding of what I read. Reviewing and synthesizing my highlights and notes to create a digest wasn’t fun, but it enhanced my understanding by forcing me to think more deeply about what I’d read. I had to identify the book’s key points, evaluate whether I believed them, and determine whether they supported the book’s main arguments or ideas. Outsourcing that to AI would get me a digest quicker, but I wouldn’t learn, understand, or retain as well—which is the whole point of reading these books to begin with.

I’m really glad I’m doing this Thanksgiving challenge now (see here). I think it’s the start of my figuring out how to sustainably synthesize and share what I learn from books. I’m not trying to check boxes; I’m trying to learn as much as possible from the books I read and share it openly so others can learn too. That’s something I’d strayed away from a bit, but I’m laser focused on it now.

Every holiday I like to give myself a challenge. In 2023, I read an 800-page book during the Thanksgiving break (see here). I’m definitely not doing that again, but I want to continue the tradition and challenge myself. I spent last weekend thinking about what the challenge should be.

Since spring 2024, I’ve been developing the habit of reading a book every week. That’s pretty ingrained now; it feels like second nature. What I haven’t mastered is consistently synthesizing what I learned from each book. I did a series of posts on some books (see here), but that habit wasn’t sustainable.

I now think that synthesizing doesn’t have to be creating a full digest of each book. It can be any of the following:

• Implementing a framework or idea by applying it to a problem (see example here)
• Describing the ideas that resonated with me and why I think they’re valuable (see example here)
• Summarizing a book

That isn’t an exhaustive list, but you get the idea.

I want to make sure I’m learning from these books and that what I learn sticks. One of the best ways I’ve found to make this happen is to share what I’ve learned.

So, my challenge this Thanksgiving holiday is to synthesize what I learned from three books in separate posts. Hopefully, this will help with synthesis after I read and make it second nature.

Wish me luck!

Happy Thanksgiving!

I hope everyone has a great holiday!

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Today I was listening to investor David Dredge on a podcast. He's based in Singapore and deals in somewhat exotic investments but considers himself a value investor. He said something (see here) that grabbed me: “Low doesn’t mean cheap.”

Just because something has a low price, that doesn’t automatically mean it’s a cheap price. Price is the amount you pay for something. Value is what the thing is worth. The two concepts are often confused, but they’re different. And price alone can’t tell you the cheapness of something.

The key element that many miss is value. Once you calculate an item’s value, you can determine whether it’s cheap or not by comparing value to the price it’s being offered at. If the price is less than the value you’ve determined, it’s priced cheaply and is likely a deal. If the price has also been reduced, the item is low-priced and cheap.

Conversely, if an item has been reduced in price but is still selling for more than the value you’ve determined, it’s priced lower, but it’s also overpriced (i.e., not cheap).

For a long time, I looked for bargains. If something was on sale, I’d think it was a deal. That was a naive way of looking at things, and it led me to overpay for things (most notably my first residence). I now think much differently. I no longer start with price or how much the price has gone down. Instead, I try to first figure out the value of something (this isn’t always easy). Then, after I feel comfortable with the value I’ve determined, I look at the price. If the value exceeds the price, I feel confident about pulling the trigger because I’m getting more value than I’m paying for.

I’ve read several biographies of and books by notable investors who started their own investment firms: Howard Marks, Warren Buffett, Charlie Munger, T. Rowe Price, Mohnish Pabrai, Joel Greenblat, Adam Seessel, and more. They all mention value investing and its founder, Benjamin Graham. Graham was the only boss Buffett ever had, and Buffett still speaks well of his mentor, some 70 years after working for him. All this intrigued me and made me want to learn more about the man so many people hold in high regard. So I read The Einstein of Money, the biography of Benjamin Graham.

After reading this book, I understand why Graham developed the value-investing concepts that have endured for a century. His approach was the result of personal and professional pain. Graham watched his widowed mother struggle to raise her children, which left a deep scar on him. It made him aware of the value of money and motivated him to obtain it so he could have freedom and avoid what he endured as a child. After starting his own Wall Street investment firm, Graham lost substantial money in the 1929 stock market crash and the ensuing Great Depression—so much that his partnership almost went bankrupt and he had to move his family to a cheaper home and generate side income as an expert witness in legal cases to make ends meet. Graham reflected on what went wrong to cause all this pain. This led to insights that shaped his value-investing framework, which he documented in his investing classics Security Analysis and The Intelligent Investor.

Graham went on to tremendous professional success, becoming a wealthy and highly respected investor and professor at Columbia and UCLA. But his personal life was filled with highs and lows. The lowest points were the deaths of his two sons. And he was imperfect and dealt with personal challenges, some of which led to marrying three times.

Graham was a brilliant person, and I now understand why so many accomplished investors respect him. His value-investing principles have endured the test of time, shaped the thinking of great investors like Buffett, and led to a cult-like value-investing movement.

I’m glad I read this book, and I want to read The Intelligent Investor too. Anyone interested in learning about the man Warren Buffett names as a major contributor to his success should consider reading The Einstein of Money.

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: 90
• Total blog posts published: 595

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed in the week ending 11/23/25 (link to the previous week’s commitments):

• Read Einstein of Money, a biography of Benjamin Graham, the father of value investing, the only boss Warren Buffett ever had, and one of Buffett’s most influential mentors
• Finished my latest weekend project. I tested and updated every book image and confirmed and updated all links to Amazon.com. I’ll share more details in the coming days.

What I’ll do next week:

• Read a biography, autobiography, or framework book

Asks:

• No ask this week

Week two hundred ninety-five 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 related to this project

What I learned:

• The pain entrepreneurs experience when they make a material mistake is immense. That pain leads them to reflect, which in turn leads to insight and a valuable lesson. Entrepreneurs want to hear other entrepreneurs’ stories to fully understand the mistakes that led to insights and lessons learned. This is best done through conversation so questions can be asked.

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

Today I looked at the calendar and realized that Thanksgiving is next week. I feel like it snuck up on me. In 2023, I challenged myself and set an aggressive reading goal: read an 800-page book during that break (see here). I enjoy these holiday challenges. Even though I sometimes make them too aggressive, it’s definitely something I want to keep doing.

That said, I need to figure out what my 2025 Thanksgiving challenge will be. I haven’t thought about it at all and have no clue what I want to do this year. I do know it won’t be reading an 800-page book!

I’ll spend some time thinking about it this weekend so I can go into next week with a clear goal.

This week I listened to an entrepreneur explain an interesting situation with a large pilot customer. He’d had a six-month contract for a paid pilot with a large company. The idea was for the company to test his software and then agree to a longer-term contract. Because of internal dynamics at the large company, the pilot ended without a new contract being signed. So, the entrepreneur disabled the customer’s access to his software platform.

An interesting thing happened. The company reached out and asked if they could still access the platform while they worked toward another contract (which was expected to take several more months). Said differently, they wanted access to the platform again even though a new contract hadn’t been agreed upon and they weren’t paying the entrepreneur. The entrepreneur was in a tough spot because he didn’t want to say no and jeopardize ongoing contract negotiations. But he didn’t want to get the large company used to accessing his software for free either. He wasn’t sure whether to grant them access as a good-faith effort or to ask for advance payment.  

While this situation didn’t feel great to the entrepreneur, I viewed it as an overall positive that showed his software is valuable to this large customer. A classic product–market fit question is “What would you do if this service or product went away?” If the customer is unbothered, then you know the solution is a nice-to-have; they can live without it. You either don’t have product–market fit or the problem you’re solving isn’t painful enough to the customer. Neither is a positive sign. If the customer is worried about it going away, that’s a great sign that the solution solves a serious pain point and is a must-have for them. A very strong signal.

This founder’s situation went a step further. When he disabled access, his large customer requested that it be restored. To me, this is a sign that his software is solving a serious pain point for that customer. They’d grown used to his solution, and when it was removed, the pain was real and they realized how much they needed it. The sequence of events that led to this wasn’t ideal. Rolling the pilot into a new long-term contract without service disruption would have been ideal. But if I had to bet, I’d say this customer will end up agreeing to a longer-term contract with this entrepreneur.