Wishing you and your loved ones a very Merry Christmas!

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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.

For the past few years, I’ve challenged myself to do something difficult during each holiday break. I enjoy these challenges because they stretch me further than usual and give me something productive and fun to work on during “downtime.”

I’ve got my daily reading habit down now, but I never established a habit of making sure I absorb what I read. So, this year, I’ve been focusing more on sharing what I’ve learned from books to make sure I’ve really absorbed them and, hopefully, to help others. To do this, I’ve been trying to synthesize some books and write posts about what I learned from them.

It’s not an established habit, so it’s been hard to do. I felt the same way when I started blogging daily and reading books daily. In both cases, I just needed more reps to get my brain used to the activity and establish the habit.

With that said, my goal for the Christmas and New Year holidays is to make progress on establishing this habit. Specifically, I plan to synthesize two books (that I’ve already read) and share posts explaining the main ideas I learned from each of them.

Wish me luck!

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: 94
• Total blog posts published: 623

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed in the week ending 12/21/25 (link to the previous week’s commitments):

• Read The Art of Execution, a framework on the psychological mistakes that undermine investment execution and lead to poor returns

What I’ll do next week:

• Read a biography, autobiography, or framework book
• Synthesize one book and share what I learned in a post

Asks:

• No ask this week

Week two hundred ninety-nine 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 planned to start synthesizing another book during a long focus session, but it didn’t happen. I need to rethink how to make this a daily habit. Maybe shorter daily sessions would work.  

What I learned:

• Rereading books—the best ones—is as important as reading new books. I need to revisit some of the most valuable lessons and timeless wisdom periodically to remind me of what I already know. See more here.

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

This week, I had a long conversation with a start-up lawyer I’ve known for almost a decade. We talked about what’s new and what we’re thinking about for 2026. He shared that he thinks AI is decimating the legal profession. Clients are using AI tools to handle more legal work, and much of what those tools generate is of good enough quality to accomplish their goals. Side note: I know of a company that used ChatGPT to generate all its legal documents when it made an offer to acquire another company, and the deal closed. They saved probably $50,000 in legal fees.

He shared with me that clients are hesitant to use him as much as they’d like because of the several hundred dollars per hour he charges. Anytime they call for something small, they know the meter is running and they’ll get a bill. So they’re using ChatGPT and other tools for small things. As they use those tools, they’re realizing the output is good enough to meet a lot of their legal needs. They’ve become more comfortable using AI as their first go-to for legal, which means they’re reaching out to their lawyers less and less.

So, what’s this lawyer going to do? He’s changing his pricing model and service offering in 2026. He plans to offer clients the option to pay a flat monthly subscription fee so they can reach out as needed without being billed hourly. As part of this service, he’ll teach his clients how to set up AI to better meet specific legal needs. His thought is that if he makes it easier for clients to use him, they’ll engage him more. And by showing them how to use AI for legal, he becomes a trusted advisor.

I wasn’t expecting to hear this from him, but it made a lot of sense. I never built legal costs into my company’s budget because the number of hours we’d use in a year varied wildly, making it hard to predict. So when we did need legal advice, I always tried to limit the scope to avoid blowing our budget. If I could have paid a flat monthly fee, I probably would have, because that would have made it easy to add legal as a line item in my budget. If I’d had that option, I definitely would have engaged our lawyer more frequently.

It's interesting to hear from someone boots on the ground how big an impact AI is having on the legal profession. I’m curious to learn how his clients respond to his pricing model change and whether the legal profession becomes more creative as AI becomes a larger part of clients’ daily workflow.

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.

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: 93
• Total blog posts published: 616

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed in the week ending 12/14/25 (link to the previous week’s commitments):

• Read The Fortune Builders, a biographical anthology of Chicago’s most successful entrepreneurial families
• Published a post about each book I synthesized during my Thanksgiving challenge (see here); you can see the posts here, here, and here

What I’ll do next week:

• Read a biography, autobiography, or framework book
• Synthesize one book and share what I learned in a post

Asks:

• No ask this week

Week two hundred ninety-eight 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:

• The hardest part of my process for learning from reading books is sharing what I synthesized. Synthesizing requires mental effort to distill a book’s contents to its most important elements. But sharing the results in writing is more difficult because I have to rearrange the elements logically and communicate them clearly and concisely to people who don’t have any context. The upside, for me, is that I understand the book deeply when I’m done.
• Amazon’s Kindle just announced new AI features that will allow Kindle users to “Ask This Book.” It’s basically Amazon tackling the problem Andre Karpathy wrote about and solved for himself (see here): improving retention and understanding by using AI to help read books.

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

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.