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!

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 synthesized a book this week—a painful process that took longer than expected. I hoped to write the blog post based on the synthesis by this weekend, but that hasn’t happened.

What I learned:

• Synthesizing a book requires a fair amount of rereading, even though I highlighted important parts during my initial read. The material sticks better the second time around, but the process still feels like it could be more efficient. Hopefully, with more reps, I’ll get better and develop some hacks too.

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

This week, I was catching up with an entrepreneur. It’s the end of the year, so I asked how 2025 has been for them. It’s been hard, they said. They feel like they’ve been getting beaten up all year and that nothing has gone their way. They survived the year but aren’t excited about what the future holds.

As they talked, it became apparent that they’ve navigated very painful situations in their business this year. While this entrepreneur was a bit pessimistic, I was more optimistic for them. Why? I think that pain is a necessary component of growth. Very rarely do people who achieve outsize success do so without first experiencing a period of what feels like extreme pain.

Why can pain be a good thing? Because what you learn from painful experiences becomes critical to helping you successfully navigate future situations. You learn lessons and gain wisdom that improve your decision-making. Better decision-making leads to more rewarding situations and more wins.

I think Ray Dalio put it best in his book Principles when he said this:

Pain + Reflection = Progress

I’m excited for this entrepreneur. I hope they take the time to reflect on the pain they’ve experienced so they can set themselves up to make serious progress in their business in 2026.

So, I’m adding one more thing to my Christmas and New Year holiday challenge. I haven’t been consistent with the Getting Things Done (GTD) method. I read David Allen’s Getting Things Done in 2024, and if I’m being honest, I loosely implemented it. I want to be more productive in 2026, and I think the GTD method could play a big role.

So, my goal is to read the GTD book again, create a clean, short-term (completed within a year) project list, and define next actions for each project.

That’s it. Wish me luck.