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.

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.