2/26/25 Update: I created a page with all 52 books I read last year. See it here.

2/27/25 Update: I’ve created a searchable library of every book I’ve read and update it weekly. See it here.

This summer, I set a goal of creating 100 podcasts about books I was reading. It forced me to start tracking my reading in a spreadsheet. It’s nerdy, but it was necessary because every week, I read a book, wrote a blog post series, and created a podcast series about each book. The spreadsheet helped me keep everything organized. I paused the latter two after the summer because they were too inefficient and time-consuming, but I kept updating the spreadsheet and reading a book a week.

I looked at the spreadsheet as I was reflecting on the books I read in 2024. I figured I’d share some stats and learnings.

High-level stat for 2024:

• Books read: 52

2024 breakdown by month:

• January: 0 (I did read, but I can’t remember what books)
• February: 2
• March: 6
• April: 6
• May: 7
• June: 5
• July: 4
• August: 5
• September: 4
• October: 3
• November: 5
• December: 5

Here are a few things I learned along the way:

• Reading two books a week was too aggressive. I tried it in the March–May period, but I wasn’t absorbing as much of what I was reading or making as many connections. I was focused on finishing the books, which isn’t why I read. The pace was too fast, so I reduced it to a book a week, which feels more sustainable.
• Sharing what I learned from my reading was the big unlock. It took my learning and thinking to another level. Writing a blog post series and recording a podcast series forced me to identify insights and organize and communicate my thinking. The key tool in that process was creating a digest of each book, which was an extraction of the information I found important in each chapter, along with my insights.
• E-readers, such as Kindles, are great devices, but I prefer reading physical books. I highlight and add notes about insightful sections and ideas in the books. Those highlights and notes are trapped in each book, so finding and using them later is difficult. See here for more. As I’ve read more, this has become a painful problem. Trying to find something sometimes means reviewing several books’ notes and highlights. Experiencing this pain led me to several feature ideas for the “book library.”
• Reading a book is simple—but learning from what I read is more involved. It’s inefficient and involves lots of steps. The process of sharing what I learn from my reading is complex. It’s hard and has many steps and lots of moving pieces. This realization led me to add several more feature ideas to the “book library.”
• The value in reading lots of entrepreneurial biographies is that you’re exposed to the best ideas and experiences of entrepreneurs, and you can pull from them when you’re faced with a problem. The challenge is that this requires a great memory or knowing exactly where to look to quickly find something you’ve read. I don’t have a photographic memory, and I don’t always remember where I read something. I want to make it easy to find what I’ve read, which will be a big part of the “book library” MVP.
• My best ideas in 2024 came from piecing ideas together from various books. Making those connections was a great way to build upon what other entrepreneurs figured out. Solving a problem by building upon the knowledge of others rather than starting from scratch led to my having better ideas. I’m not an idea guy, so this was perfect for me, and I want to do more of it going forward. I don’t think this has to be completely manual and inefficient. Figuring out how to solve this and incorporate it into the “book library” is challenging, but I think it can be done, and I’m excited to figure this out because it’ll be a huge unlock for myself and others.

Those are my takeaways and reading stats for 2024!

As part of my Thanksgiving challenge (see here), I said I’d synthesize three reads. This is the first synthesis.

A few years ago, I got serious about reading books to better understand investing. I decided to start on the right foot, so I read How to Read a Book. I remember that this book resonated with me, but it’s been a few years. So, I decided to brush up on it and share my takeaways to reinforce my learning. This book was written in the 1940s. It isn’t as concise as modern books usually are, and the meaning of the words isn’t always obvious, so digesting and understanding it took more time.

The main idea that resonated with me is this:

Synoptical reading is the highest level of reading. Reading multiple books on the same subject helps you gain a deep understanding of a topic from various perspectives. That deep understanding positions you to think independently and creatively to form your own conclusions.

This idea stuck with me because it matches a pattern I’ve noticed. Many people who’ve achieved outsize success read synoptically to improve decision-making and accelerate problem solving. They don’t start from scratch; they leverage what others have already figured out. They stand on the shoulders of those who came before them.

Before I get into how to read synoptically, I want to share something I find helpful to know, namely that there are four levels of reading:

• Elementary reading – Understanding what a sentence is saying. Think grade school.
• Inspectional reading – Understanding the main ideas when time is limited. This involves skimming (i.e., pre-reading) and then superficial reading.
• Analytical reading – Understanding the main argument of a book. This is intense and active (not passive) reading.
• Synoptical reading – Understanding a topic by comparing different perspectives from several books and coming up with your own conclusions.

So, how the heck do you read books synoptically? It’s a simple two-stage process (I added a third stage). Here are the stages and steps:

• Stage 1 (my addition): Define the problem you need to solve or the topic you want to understand.
• Stage 2: Identify relevant books.
  
  • Step 1: Create a list of relevant books. The library and notes or bibliography sections of other books (see here) are useful
  • Step 2: Inspect each book via inspectional reading (i.e., skimming and superficial reading).
  • Step 3: Narrow your list to the most relevant books.
• Stage 3: Synoptically read relevant books.
  
  • Step 1: Find relevant passages. Identify passages that help you solve your problem or understand your topic. Be selfish and find the parts of the books that serve your interest. You don’t have to read the book the way the author intended.
  • Step 2: Bring the authors to your terms. Authors may use different terminology to describe similar things. Come up with your own language and convert what you’re reading into it so it makes sense to you.
  • Step 3: Ask the right questions. Create a set of questions you want answered by the books. The answers should enhance your understanding of your topic or give you ideas about how to solve your problem. Every book won’t answer every question, and that’s okay. Example questions include: Does this problem or topic exist? How can we recognize it when we see it? What does this idea look like when it happens? What happens because of it?
  • Step 4: Define the issue. Authors may have differing views on the topic or problem. Identify the central question or issue underlying their disagreements.  
  • Step 5: Analyze the discussion. Look at how each author answers the central issue you identified, compare their arguments, and understand how their views relate to—or conflict with—each other.
  • Step 6: Think. Use your analysis to develop your own conclusions about the topic or solutions to your problem.

That’s it. That’s how you read multiple books synoptically.

So, what if you want to read a single book? Good question. That’s where analytical reading comes into play. Here are the stages and steps:

• Stage 1: Figure out what the book is about.
  
  • Step 1: Figure out what kind of book it is and what topic it covers.
  • Step 2: Describe the book’s main point in one short sentence.
  • Step 3: Show the book’s skeleton—break it into its major sections, figure out how they connect, put them in order, and create an outline.
• Stage 2: Figure out what a book is saying.
  
  • Step 1: Figure out what the author means when they use certain important words or phrases.
  • Step 2: Identify the author’s main claims by focusing on their most important sentences—and make sure you understand those claims.
  • Step 3: Understand the reasoning the author uses to back up the main claims by following the reasoning across multiple sentences or paragraphs.
  • Step 4: Figure out which of the questions the author set out to answer were answered, which ones weren’t, and whether the author knew they left some questions unanswered.
• Stage 3: Criticize a book.
  
  • Step 1: Understand the author’s perspective first. Don’t judge the book until you fully understand it. You can’t agree or disagree until you can accurately explain what the author meant. This usually requires outlining and interpreting the book.
  • Step 2: Don’t disagree with the author just to be contrarian or combative—your disagreement should be rational.
  • Step 3: If you disagree with the author, back up your criticism with knowledge—that is, evidence, logic, or clear reasoning, not personal opinion.
• Stage 4 (my addition): Reach your conclusion.
  
  • Step 1: Crystallize your thoughts about what you’ve read.

The steps listed above aren’t complex. They somewhat remind me of how I read textbooks in college, which was a period that felt like rapid-paced learning. So reading this way is definitely doable.

I’m not going to lie; this book wasn’t an enjoyable read. But the framework it provides around synoptical and analytical reading were worth the effort. I think they’re useful for anyone serious about self-educating and looking for ways to add more structure.

I’m glad I synthesized the ideas from this book that I found useful. It really ingrained the ideas in my brain this time around. Hopefully, this synthesis will be helpful to others, too.

I’ve been pretty religious about weight lifting and cardio this year: cardio daily and weights five times a week. The last week or two, I haven’t been as consistent with the weights, and I’ve noticed that my productivity is a bit off. Holiday mode? Maybe.

The more likely explanation is that lifting weights gives me energy, which makes me more productive.

Going into the last few weeks of the year, I want to lift consistently so I can finish the year as productively as possible and start 2026 on the right foot.

I’m wrapping up my blog posts about the three books I synthesized as part of my Thanksgiving challenge (see here). As I was working today, I thought about several insights:

• The synthesis of the books happened within the time frame I planned (i.e., Thanksgiving weekend). But sharing what I learned in a way others could easily pick up took longer than I estimated.
• Creating a post that summarizes an entire book is something I can do, but it’s likely to be rare.
• Creating the digest is helpful, albeit painful and time-consuming. It forces me to pick out the most important points from the book. But the process of turning it into something useful to others forces me to understand the material deeply. I didn’t realize how much of what I’d consumed, even after I created the digest, I didn’t fully grasp. Sharing is a force function in understanding.  
• The more poorly a book is written, the more work it is to create a digest and post. One book, written in the 1940s, was wordy and poorly structured. Piecing together what the author was trying to convey in a simple way that people could grasp quickly took more effort. Good content, but not presented well.
• The concept of ideas is starting to resonate with me. What ideas in a book got me excited, and why? If I can answer those questions, those ideas are probably worth sharing.
• Breaking complex frameworks down into something easily understood by others (and giving myself a quick reference) is something I toyed with and enjoyed. Lots of work, but curation and simplification are valuable to others (and will be valuable to my future self when I need my memory jogged quickly).
• You don’t deeply understand something unless you can communicate or teach it to others in a way they can easily grasp. If I want to force myself to understand something deeply, I should make myself write a blog post about it.
• Investors who teach or openly share what they know may have a secondary motive. It helps people, which is great. But it also forces them to learn things more deeply, which likely has a positive impact on their decision-making and investment returns. This is likely true for other professionals outside investing, too.

Those are a few quick takeaways from my latest holiday challenge. I’m glad I decided to do it. It reminded me of the value of synthesizing my reading, and it’s forcing me to figure out how to develop the habit of doing so consistently.

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: 92
• Total blog posts published: 609

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed in the week ending 12/7/25 (link to the previous week’s commitments):

• Read Quality Investing, a framework on what characteristics make a public company “high quality” and how to evaluate them

What I’ll do next week:

• Read a biography, autobiography, or framework book
• Publish a post about each book I synthesized during my Thanksgiving challenge (see here)

Asks:

• No ask this week

Week two hundred ninety-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 related to this project

What I learned:

• Andrej Karpathy created a free tool for reading books with AI (see my post here). Good idea, and useful tool. I like reading physical books, so that’s still a point of friction for me. But this tool is validation that a problem exists and people are trying to solve it (but not that the problem is painful enough for them to pay for a solution).
• In the comments after Karpathy’s post sharing his tool (see here), other people shared tools they’d built to solve this problem. I haven’t tested them, but a few seem interesting, and I want to play with them. X comments can be an overlooked gold mine.

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

Earlier this year, I shared a video (see here) that Andrej Karpathy made about how he uses large language models (LLMs). According to his website, Karpathy was “a research scientist and founder member at OpenAI” before spending several years at Tesla as Senior Director of AI. His video jumped out at me because he uses LLMs to help him read and understand books and research papers. He did this manually, and he described how painful it was, which I summarized in this post.

He’s taken his habit of reading with LLMs even further and developed a process with three passes: first, manual reading; second, having the LLM “explain and summarize”; and third, Q&A with the LLM. See his post about this here.

In addition, he solved his own pain: He shared that he’s built a simple tool for implementing this process with less friction. It enables him to read books in ePub format and feed the text of the book to the LLM, so he can ask the LLM questions while he reads. See more details in his post here.

He shared the code for his tool so others can use it, which is pretty cool. It’s available on GitHub here.

This sounds really interesting, and I can’t wait to give it a try.

This week, I listened to a founder pitch his early-stage start-up. The company raised a few hundred thousand dollars a few years ago. Today it’s out raising another $500k to $750k, which it hopes to complete in the next few months.

The company is growing, but it’s not growing rapidly. So I was curious about what milestones they plan to hit with the capital they’re raising. The company wants to extend its runway by a year or two to give it time to reach breakeven.

When investors put money into a company, they’re looking for a return that’s high enough to justify the risk of capital loss they’re assuming. Their ROI can be through appreciation of the company’s value (i.e., their stake is worth more) or through dividends the company distributes from its free cash flow.

When a company is at breakeven, it’s neither losing money (consuming cash) nor making money (generating cash). It’s covering expenses to keep the lights on. If a company is growing rapidly and is at breakeven, that can be a good situation. Cash generated by the company’s operations is being reinvested in growth initiatives. In theory, if it stopped investing in growth, it would have cash available for dividends or a rainy day. But if the company is at breakeven and not growing, or growing slowly, that means it’s generating just enough cash to maintain itself, with little left for anything else.

Breaking even is a key milestone for a company because it means it’s self-sustaining: totally funded by customer revenue. But if a company is raising capital from investors with breakeven as its goal, it’s important to keep in mind that investors are seeking a return. Breaking even means there won’t be cash to pay dividends to investors, so the investors will be looking for their ownership to be worth more. If the company is breaking even but not growing revenue at a material rate and therefore not increasing its valuation, no clear path to an ROI exists. The likelihood that investors will agree to put money into the company is low.

Any founder raising capital to reach breakeven should consider how they’ll generate a return on the capital they’re seeking from investors and include that info in their pitch.

Today, it hit me that 2025 is almost over. Only four more weeks. It feels like the year flew by. I’ve realized that it’s time to start thinking about 2026. I’m not a fan of setting traditional yearly goals. Because luck and randomness are involved, I can’t control whether I achieve a desired outcome. Instead, I like to focus on habits that, if done consistently throughout the year, materially increase my chances of a positive outcome at the end of the year.

I’ll be thinking about 2026 over the next few weeks and identifying the new habits I want to embrace.

I’ve been curious about the “Great Inflation” period of the 1970s. Reading about decisions in the 1960s and 1970s that led to it was eye-opening. A few months ago, I came across a biographical anthology that caught my eye because it talked about what happened after that period—specifically, how the Great Inflation contributed to the craziness of the 1980s: the junk-bond boom, the leveraged buyout wave, the birth of private equity, and the eventual S&L turmoil.

Dangerous Dreams was interesting because it wasn’t just a biographical anthology that talked about several people in isolation. Rather, it discussed each person’s story and the role they played in the creation and evolution of the junk-bond mania of the 1980s. It was the story of how each person contributed to the broader story and how these players influenced each another.

Louis “The Junkman” Wolfson, Charles Merrill, conglomerate builder James Ling, Michael Milken, Ivan Boesky, T. Boone Pickens, Carl Icahn, Rudy Giuliani, and others were profiled.

The main character, the man who helped birth the junk-bond market, was Michael Milken. The book details his rise and spectacular fall. It does a great job of explaining how an unheard-of book-on-bond analysis sparked Milken’s ideas that led him to build and control the junk-bond market throughout the 1980s.

I learned a lot from this book, especially about how the 1970s created an environment in which the stock market valued blue-chip companies at significantly less than their value and high-growth companies were pretty much shut out of the bond market—all of which led to craziness on Wall Street in the 1980s.

Anyone interested in Michael Milken, T. Boone Pickens, the origins of the junk-bond market, the savings and loans crisis, or how private equity got started should consider reading Dangerous Dreamers. You’ll come away with insights into all the above and more.