Yesterday, I shared a post (see here) that includes my reading stats for 2025. After writing it, I realized that since I began my book-a-week reading habit in April 2024, I’ve read 100 books in roughly 100 weeks. For whatever reason, that hadn’t occurred to me before yesterday. It made me feel accomplished and motivated, and it feels like a material milestone that I want to keep extending. So now I’m more motivated than ever to read a book every week!

In 2024, I began reading a book every week. I wanted to share what I’d read, so I posted a recap of my 2024 reading stats and lessons learned (see here). I was frustrated by how hard it was to share a list of all the book titles (see here), so I created a page about each book I read in 2024 (see here). I wanted to replace the Google Sheet I use to track all my reading, so I created a searchable library of all the books I’ve read (see here). I update it weekly.

Last year, 2025, was year two of consistently reading a book every week, and I want to share a recap of my stats and lessons learned. Sorry it’s late (the goal was January).

High-level stat for 2025:

• Books read: 51

2025 breakdown by month:

• January: 4
• February: 4
• March: 4
• April: 4
• May: 4
• June: 5
• July: 4
• August: 5
• September: 4
• October: 4
• November: 5
• December: 4

If you’d like to know what those 51 books were, see my 2025 reading list here.

Here are a few things I learned along the way:

• Reading for general information is critical if I want to generate new ideas—and I do. A Technique for Producing Ideas reinforced this. I have to learn about ideas so I can borrow from them when I’m trying to come up with a new one myself.
• Rereading high-quality books is sometimes better than reading new books. I reread a few books last year, and that helped me a ton. I’m now trying to reread at least one book every month.
• Synoptical reading is key to leveraging books to solve hard problems or deeply understand something. See more here.
• Framework books are a good fit for my personality, and they’re helpful. They give you the framework or process to use when you’re trying to accomplish something. They don’t give you the answer, but they show you how to get to the right answer.
• I get the most out of books when I read with intention; that is, with a clearly defined purpose for reading that book. That purpose should be a problem I’m actively trying to solve or a topic I want to understand better. This year, I’ve started writing down the problem I need to solve or the topic I want to understand before I choose a book. That’s helped me do more synoptical reading and get more from my reading that I can quickly put to use.
• There are no hacks with reading. I have to not only read but also do the work to understand what I’m reading. The best way to do that (that I’ve found so far) is to synthesize a book and share what I learned with others. But I haven’t found a way to be consistent with that.
• Learning through reading doesn’t feel like a chore anymore. It’s something I enjoy doing in my downtime. The personal-growth aspect of it appeals to my curious nature, and I feel like I can sustain it for a long time.
• Application of knowledge is the key to getting better outcomes. A priority of mine in 2025 is to apply what I’ve learned from reading, specifically around decision-making with imperfect information and probabilistic thinking.

Those are my takeaways and reading stats for 2025!

At the beginning of 2025, I shared a post that included the number of books I read in 2024 and what I learned while establishing my reading habit. It also links to a page where you can see every book I read in 2024. Writing that post led to my creating a book list page (see here) populated with all the books I’ve read over the last decade or so. Every week, I update that book list with my latest read.

I read consistently in 2025, but I haven’t created a dedicated page for each book I read, posted my reading stats, or shared what I learned during my second year of consistent reading. So that’s my project for this weekend. I’m going to knock those three things out and pin that new post as the first one on my blog.

Next week, everyone will be able to see a bunch of info about the books I read in 2025.

This week I had the opportunity to participate in my first book club. For context, this book club was virtual and academically oriented. A few initial thoughts:

• Over 250 people attended, which shocked me. I didn’t have any expectations, but I hadn’t considered that such a crowd would take part.
• The virtual nature of this club allows it to cast a wide net. There were people from other countries, including Canada. The internet removes boundaries—this group could find people anywhere.
• The author of the book was part of the session and shared his thoughts, which I enjoyed. It’s always nice to hear authors’ deeper thoughts.
• This meeting was styled as something of a debate. It began with people arguing for and against the argument in the book. The author then responded to points against the book.
• Many of the arguments presented were prepared statements.

Overall, I enjoyed my first book club experience. The scale and reach of this club were much greater than I could ever have imagined. That definitely stuck with me and has me thinking much bigger about the possibilities of book clubs.

Last week, I reread Felix Dennis’s book How to Get Rich. Dennis was the founder of Dennis Publishing, Maxim magazine, and Micro Warehouse, a mail-order computer parts company. He was a colorful person who lived an extreme lifestyle, but his thoughts on creating wealth through entrepreneurship were based on his experiences and, in my opinion, spot on.

After reading this book in 2024, I wrote a blog series that captured its main ideas. You can read them:

• Felix Dennis Part 1: Getting Going as a Founder
• Felix Dennis Part 2: Succeeding as a Founder
• Felix Dennis Part 3: Winning and Walking Away

Today I read those posts again, and even after a second reading of the book, I think they capture its essence in a concise way.

His lessons on getting started as a founder got me thinking, especially his advice to find new industries that are growing fast. Lots of people are doing this with AI. His advice to never think small and to act big also resonated with me. He’s right that people stop doing the things that led to their success once they become successful, or they think small and don’t embrace new ideas and ways of doing things.

I’m glad I read this book again. It was a nice refresher.

Side note: I read Dennis’s biography More Lives Than One too. You can learn more about his life journey  here, in the blog post series I wrote based on this biography.

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.

I’m working on establishing a habit of synthesizing the books I read and sharing what I learn. I want to not just consume what’s in books but also digest and understand their ideas. I’ve set Thanksgiving and Christmas goals to synthesize a few books for each holiday. Here’s what I’ve learned so far:

• Painful – I don’t have a good rhythm or any tricks for synthesizing, so every time I sit down to do it, it’s painful. It reminds me of the pain when I first started blogging in 2020. It feels like the pain of learning to do something new.
• Daily is better – I started out doing marathon sessions. The problem was that it’s hard to consistently carve out time for them. So, I’ve moved to working on this as close to daily as possible. I’m basically breaking the synthesis up into smaller sessions.
• 50 pages – This seems to be the limit of what I can do in a single day before it becomes painful. That’s not a bad pace because I could hypothetically synthesize a 350-page book in a week. Luckily, most books I read are in the range of 250 to 300 pages.
• Time – Synthesizing 50 pages takes a few hours—a lot more time than I’d like. I want to get to the point where I can synthesize 50 pages in an hour or less.
• Outline – Creating an outline of key information in each chapter feels natural and is working well.
• My wording – Rewording what I read, instead of copying verbatim, forces me to really understand what I’m synthesizing. Copying word-for-word defeats the purpose.
• Blog-post prerequisite – Creating an outline while synthesizing a book makes it possible to write a rich blog post. When I don’t do this, it feels impossible to write more than a surface-level post.
• Creating assets – Creating syntheses is painful, but I think each one is an asset, and I could end up with a library of valuable (to me) assets that will likely pay dividends in the future. I can’t say how, but I know having these in electronic format will make it easier for me to use this knowledge in the future, versus being trapped in physical books. Pretty sure I’ll run these through LLMs to help me make decisions in the future.

That’s what I’ve learned so far. I’m still working to try to find my groove and establish the habit of synthesizing books. It’s not easy, but hopefully, as I get more reps, the habit will form.

In several books, I’ve read about a particular family and their above-average deal-making skills. The Pritzkers are a Chicago-based family known for turning Hyatt hotels and numerous ventures into a sprawling, wildly successful empire of closely held private companies. According to a 2013 WSJ article (see here), the family empire of over 150 companies was worth $30 billion in 2011. Curious, I started researching them, but I couldn’t find much. I did find one book, a biographical anthology—not quite what I was looking for, but it was all I had.

The Fortune Builders, written in 1986, profiles the wealthiest Chicago families who built companies that had significant impacts on America. Most chapters are dedicated to telling a single family’s multigenerational story, beginning with these patriarchs:

• Cyrus Hall McCormick: McCormick Harvesting Machine Company/Navistar
• Philip D. Armour: Armour & Company
• Marshall Field: Marshall Field & Company
• The Pritzker family (including Jay Pritzker): Hyatt Hotels
• John D. MacArthur: Bankers Life and Casualty
• William Wrigley Jr.: Wrigley Company
• Arthur C. Nielsen Sr.: A.C. Nielsen Company
• Gustavus Franklin Swift: Swift & Company

The Pritzker family profile was exactly what I was looking for. It went deep into the family’s origins. Interestingly, they were all lawyers as of the book’s publication date and the law firm they started decades earlier stopped taking outside clients to do legal work only for the family and its companies. The book tells the story of how the family acquired the original Hyatt hotel and grew it into a leading international hotel brand. It also talks about the family’s vast portfolio of companies.

The other profiles that stood out were those of Marshall Field, the department store magnate, and Cyrus McCormick. Marshall built an enormous business (it was doing roughly $35 million in revenue in 1895 or $1.35 billion in 2025 dollars). Subsequent generations turned it into a diversified empire with stakes in real estate, newspapers, magazines, radio stations, TV stations, and various other industries.

Cyrus McCormick was a controversial figure who took his father’s concept for a wheat reaper and turned it into the McCormick Harvesting Machine Company, which changed farming and global food production. That company then became International Harvester, one of the largest tractor manufacturers, and later became Navistar International Corp, a major global manufacturer of commercial and heavy-duty trucks. So, any school bus, dump truck, or 18-wheeler with an “International” logo is the result of the McCormick family’s efforts across a century.

I had no idea about the origins of these families and the impact they had on American society. I’m glad I read this book. I’ll definitely look for more to read on several of these families.

Anyone interested in how entrepreneurs shaped Chicago and the nation should consider reading The Fortune Builders.

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

Earlier this year and last year, I read several books by people who’d achieved outsize success. All of them talked about the importance of checklists. I was curious to understand why checklists were so helpful, so I read The Checklist Manifesto by Atul Gawande. Here’s what I learned:

Main idea: Checklists increase your chances of success in situations with extreme complexity. Catching errors early and forcing consistent execution, they reinforce discipline.

Extreme complexity is a significant problem. As a society, we’ve created more know-how about difficult situations and problems than has ever before existed. We’ve armed the most intelligent people with all this know-how, but it’s unmanageable. There’s too much of it, and it’s exceedingly complex. No one can consistently apply it correctly, safely, and reliably.

In certain fields—medicine, for example—managing extreme complexity has become an art form. Most people struggle with doing it consistently. In a life-or-death field like medicine, the result can be tragedy.

I find it helpful to think about any failure as falling into one of these three categories:

• Necessary fallibility – Some things are beyond your capacity to understand or do, but you try anyway.
• Ignorance – You don’t have a full understanding of how something works. A doctor isn’t aware of the latest studies on treatment of a particular condition and gives a patient the wrong treatment plan for his illness.
• Ineptitude – You have a full understanding of the relevant knowledge, but you failed to apply it correctly. A five-story building that you designed collapsed due to a flaw.

Why is the main idea important?

Professions in which risk, reward, complexity, and uncertainty are high benefit most from checklists. The discipline involved in following processes and procedures improves decision-making and consistency of action and increases the chances of positive outcomes.

Increasing your chances of success in fields with power-law distributions, such as entrepreneurship or investing, means that checklists can pay significant dividends.

Before I get into the requirements for a checklist, it’s helpful to understand that there are two types of checklists:

• DO–CONFIRM  – A job was performed from memory and experience. Then you run through a checklist and confirm that everything required was done.
• READ–DO – People carry out tasks as they check them off on a checklist. It’s more like following a recipe. High-pressure, time-sensitive situations benefit from READ-DO checklists. Think of an airplane with a mechanical issue mid-flight.

So, what makes a good checklist? Most of us have seen good checklists, but here are a few things to keep in mind:

• Have a clear and concise objective for the checklist.
• Focus on “killer items,” critical steps that are dangerous to overlook but sometimes skipped.
• Make them actionable, with a specific response for each item.
• Include five to nine items, which is the limit of working memory. There’s flexibility in this, though.
• Checklists aren’t comprehensive how-to guides. They’re quick, simple tools to help people navigate tough situations using skills they already have.
• Use simple, easy-to-understanding wording.
• Always test the checklist in the real world before finalizing it, because the real world is always more complex than expected.
• Bad checklists are “vague, imprecise, too long, hard to use, and impractical.” They’re often created by people who aren’t doing the work themselves or aren’t familiar with its details.
• Good checklists are “precise, straight to the point, and easy to use in difficult situations.” Provide reminders of only the most important steps, not every single step. They’re practical and created by people who understand the work being done.

That’s it; that’s what I learned from reading this book. My big takeaway is that checklists are simple and effective tools with an outsize impact in critical situations. There’s nothing terribly complicated about creating them. The hardest part is having the discipline to use them consistently.