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!

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.

A few weeks ago, I was reading a blog post about Costco and its founder, Sol Price. I’m familiar with the discount warehouse retail model because I’ve read biographies about the Home Depot founders, Bernie Marcus, Arthur Blank, and Ken Langone. The post I was reading thoroughly explained not just what Costco’s business model is but also why it’s been so successful. A key thing that stood out to me was how its membership model acted as a filter. It weeded out unprofitable customers and attracted highly profitable, loyal, repeat customers. That really got my wheels turning about my old company, given that it was retail oriented and we never figured out how to consistently attract the type of customer we wanted.

My takeaway is that I should have studied more businesses and industries when I was running my company. Because I didn’t, I tended to follow what others in my industry did—their business models and go-to-market strategies. What I didn’t realize was that there are tons of other models and strategies that people smarter than me had figured out. I could have borrowed from those to create something “innovative” in my industry, which would have given us a competitive advantage and likely increased profitability too.

I was “too busy” to focus on anything but my own business. But what I didn’t realize was that studying other founders and businesses would have made me more aware of the possibilities in business. That increased awareness would have helped me create better solutions, faster, to my business problems. All of which would have benefited my business tremendously.

I now believe that to achieve outsize success in the game of business, you must be a student of the game. ’m not a lifelong student of the game of business, but I’m making up for lost time now.

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: 91
• Total blog posts published: 602

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed in the week ending 11/30/25 (link to the previous week’s commitments):

• Read Dangerous Dreamers, a historical narrative about the people, especially Michael Milken, and events that set the stage for the junk-bond boom, LBO wave, and eventual S&L turmoil of the 1980s
• Completed my Thanksgiving challenge (see here)—I’ll share the results in posts this upcoming week

What I’ll do next week:

• Read a biography, autobiography, or framework book

Asks:

• No ask this week

Week two hundred ninety-six 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:

• 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!