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!

A few weeks ago, I wrote about how one start-up lawyer is changing his business model because of AI’s impact (see here). A few people reached out to me after that post and shared their perspectives on the disruption of legal services and other industries by AI. This topic is clearly top-of-mind for more people than I realized.

Today I read a blog post (see here) from Fred Wilson, founder of the famed venture capital firm Union Square Ventures (USV). Wilson describes having always been uncomfortable with the legal costs that USV incurs to close financing rounds for new start-ups they invest in. His latest quote was $50k for a deal he was working on last month (and the start-up’s lawyers probably charge it something similar, so the total for both parties is about $100k).

Wilson decided to try something different. He loaded Google’s NotebookLM with all his firm’s historical closing docs and the start-up’s data room docs. He asked NotebookLM a bunch of questions, and it pinpointed one issue, which he resolved with the start-up and its lawyers.

The end result was that with two hours of Wilson’s time and no legal fees, he was able to get comfortable with the deal docs (and, I assume, close the deal or get it close ready). That’s a tremendous cost and time savings.

This is a very interesting use case of AI empowering law firm customers, specifically investment firms, to move faster and at lower cost. It confirms what the start-up lawyer I spoke with last month believes: AI is disrupting the legal industry by empowering lawyers’ clients, and law firms will be forced to adapt.  

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: 96
• Total blog posts published: 637

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed in the week ending 1/4/26 (link to the previous week’s commitments):

• Reread Getting Things Done, a framework for boosting productivity while reducing stress
• Synthesized The Little Book of Market Wizards

What I’ll do next week:

• Read a biography, autobiography, or framework book
• Write a post sharing what I learned from synthesizing The Little Book of Market Wizards
• Write a post sharing what I learned from synthesizing The Art of Execution

Asks:

• No ask this week

Week three hundred one 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:

• I’m still synthesizing the second book (The Little Book of Market Wizards) of my holiday challenge (see here). I thought I’d be done by now, but making this a daily habit hasn’t stuck yet. I want to find hacks that let me synthesize books more efficiently.

What I learned:

• I posted one synthesis of a book, and it resonated with people. I assume they appreciate getting the main points of the book in much less time than it would take to read it.
• When I synthesize a book, I create a digest in Google Docs and then write a post based on that doc. This week, I was trying to remember something from a book. Instead of grabbing the book, I used the digest and post to refresh my memory. Reviewing either or both is much more efficient than digging into the book itself. I’ll be doing more of this when I want to revisit material from books.

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

A close friend was telling me about how the company he works for completed its IPO in December. I realized I haven’t done an IPO update since Q2 (see here). I know that IPO activity picked up in 2025, but I wanted to know by exactly how much. So today I dug through data. Here are the updated IPO stats for calendar year 2025:

• 2025: 347

Here’s the breakdown by month:

• January: 28
• February: 28
• March: 19
• April: 32
• May: 33
• June: 26
• July: 37
• August: 28
• September: 32
• October: 35
• November: 18
• December: 31

For comparison, here are previous years’ IPO stats:

• 2024: 225
• 2023: 154
• 2022: 181
• 2021: 1035
• 2020: 480
• 2019: 232
• 2018: 255
• 2017: 217
• 2016: 133
• 2015: 206

IPO activity picked up significantly last year. In 2025, IPOs increased by 54% year over year. And increased by 125% from the 2023 post-COVID, post-ZIRP low. Another interesting fact is that if you exclude the COVID years of 2020 and 2021, when interest rates dropped rapidly, and look at more normal years, 2025 was the most active year for IPOs in the last decade.

I imagine that technology CEOs and their PE or VC investors are watching these IPO stats and thinking about taking their companies public in 2026, given public market investors’ appetite for buying shares in tech companies.

I’m curious to see how Q1 IPO activity looks and if 2025’s trend continues.

If you want to see the IPO stats—recent or historical—try here (where I get my IPO data).

I use AI daily, and for most of 2025, I used ChatGPT as my main AI tool. This week, a friend asked me if I wanted some candid feedback. A look in the mirror, so to speak, with the reflection generated by AI’s understanding of me. I love getting candid, raw feedback, so I said yes.

They told me to run this prompt in ChatGPT: “Be blunt and honest with me and tell me what I need to change for 2026.”

Using the 5.2 model, I did. Even though ChatGPT doesn’t have full context about me because I don’t run everything I’m thinking or doing through the platform, it still gave me a thorough, thought-provoking response. It got me thinking, which I enjoyed.

If you’re a ChatGPT user and you’re curious about what it thinks you should change about yourself, run this prompt. It’s fun!

Happy New Year!

I’m in the middle of synthesizing The Little Book of Market Wizards. I like this book because it details how some of the top market participants (traders and investors) avoid psychological errors that lead to bad decisions. It’s essentially wisdom on how to execute an investing strategy without making errors.

One of the people quoted in the book is Ray Dalio, founder of hedge fund Bridgewater. What he said stuck with me:

[T]here is an incredible beauty in mistakes because embedded in each mistake is a puzzle and a gem that I could get if I solved it (i.e., a principle that I could use to reduce my mistakes in the future).

I really like this framing. Mistakes are a puzzle to be solved, and solving them yields a gem. I think that’s a great way to think about future and past mistakes. Each one is an opportunity to figure something out and find a gem that will help you going forward.

This past weekend, I posted in the Library on this site the last book I’ll read in 2025. For anyone interested, it’s The Little Book of Market Wizards. This year, 2025, is the second year of my daily reading habit and the first year that I read a book every single week.

Last year, I created a page that lists all the books I read in 2024 (see here). I’ll do the same this year and should have that published early in the new year.

I’m still getting a lot out of the daily reading habit. My plan is to keep it up and read a book a week in 2026.

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: 95
• Total blog posts published: 630

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed in the week ending 12/28/25 (link to the previous week’s commitments):

• Read The Little Book of Market Wizards, a framework on the core psychology principles that elite public-market investors used to execute their investing strategies and generate outsize returns over long careers
• Synthesized The Art of Execution

What I’ll do next week:

• Read a biography, autobiography, or framework book
• Synthesize The Little Book of Market Wizards
• Write a post sharing what I learned from synthesizing The Art of Execution

Asks:

• No ask this week

Week three hundred was another week of learning. Looking forward to next week!