I learned something else from my Thanksgiving Day challenge. From synthesizing and writing posts about books I read months or years ago, I realized how much I’d forgotten. I now see that it’s valuable to refresh knowledge. Secondarily, synthesizing and sharing is the ultimate way to do a refresh, because I can’t write good posts explaining something if I don’t understand it myself.

So, what does this mean? My weekly reading habit has mostly been about reading a new book every week. I want to change this a bit so I’m rereading books at some regular (to be determined) interval  and sharing what I learned from them. I’ll get a lot out of this, especially since I’ve marked a few books as worth reading annually but don’t have a process to make sure it happens.

It's my first new habit for 2026! I’ll think it over more and share what I settle on.

After revisiting How to Read a Book and synthesizing it (see here), I realized that I prefer synoptical reading and had spent most of the year doing it. Hence, in the library section of this site, you see that each book lists the number of books it’s connected to. I also read analytically, but less often, and honestly that isn’t my first choice.

Another thing I realized is that I haven’t been consistent in doing Stage 1 (which, ironically, I added to the process). Stage one is “Define the problem you need to solve or the topic you want to understand.” But most times, I pick up a book based on what feels good at the time. I read it, and if it mentions another book, I read that book too. The result is that I’m not reading to solve top-of-mind problems or understand the very issues slowing me down. I’m just gathering knowledge that might not be what I need to move forward.

I thought about it today and realized that it takes effort to crystallize a specific problem. It’s not easy or natural for many people, which explains why so many early-stage founders can’t articulate the problem they’re solving (see here). But, as Kidlin’s Law says, if you write a problem down clearly, then the matter is half solved.

So, going forward, I’ll write down the problem I want to solve or the topic I want to understand better before I start reading synoptically. My hunch is that I’ll read more intensely and accelerate my progress by focusing on that problem or topic as I read.

I’m wrapping up my blog posts about the three books I synthesized as part of my Thanksgiving challenge (see here). As I was working today, I thought about several insights:

• The synthesis of the books happened within the time frame I planned (i.e., Thanksgiving weekend). But sharing what I learned in a way others could easily pick up took longer than I estimated.
• Creating a post that summarizes an entire book is something I can do, but it’s likely to be rare.
• Creating the digest is helpful, albeit painful and time-consuming. It forces me to pick out the most important points from the book. But the process of turning it into something useful to others forces me to understand the material deeply. I didn’t realize how much of what I’d consumed, even after I created the digest, I didn’t fully grasp. Sharing is a force function in understanding.  
• The more poorly a book is written, the more work it is to create a digest and post. One book, written in the 1940s, was wordy and poorly structured. Piecing together what the author was trying to convey in a simple way that people could grasp quickly took more effort. Good content, but not presented well.
• The concept of ideas is starting to resonate with me. What ideas in a book got me excited, and why? If I can answer those questions, those ideas are probably worth sharing.
• Breaking complex frameworks down into something easily understood by others (and giving myself a quick reference) is something I toyed with and enjoyed. Lots of work, but curation and simplification are valuable to others (and will be valuable to my future self when I need my memory jogged quickly).
• You don’t deeply understand something unless you can communicate or teach it to others in a way they can easily grasp. If I want to force myself to understand something deeply, I should make myself write a blog post about it.
• Investors who teach or openly share what they know may have a secondary motive. It helps people, which is great. But it also forces them to learn things more deeply, which likely has a positive impact on their decision-making and investment returns. This is likely true for other professionals outside investing, too.

Those are a few quick takeaways from my latest holiday challenge. I’m glad I decided to do it. It reminded me of the value of synthesizing my reading, and it’s forcing me to figure out how to develop the habit of doing so consistently.

Earlier this year, I shared a video (see here) that Andrej Karpathy made about how he uses large language models (LLMs). According to his website, Karpathy was “a research scientist and founder member at OpenAI” before spending several years at Tesla as Senior Director of AI. His video jumped out at me because he uses LLMs to help him read and understand books and research papers. He did this manually, and he described how painful it was, which I summarized in this post.

He’s taken his habit of reading with LLMs even further and developed a process with three passes: first, manual reading; second, having the LLM “explain and summarize”; and third, Q&A with the LLM. See his post about this here.

In addition, he solved his own pain: He shared that he’s built a simple tool for implementing this process with less friction. It enables him to read books in ePub format and feed the text of the book to the LLM, so he can ask the LLM questions while he reads. See more details in his post here.

He shared the code for his tool so others can use it, which is pretty cool. It’s available on GitHub here.

This sounds really interesting, and I can’t wait to give it a try.

Last year, I was creating a blog post series for each book I read. After reading a book, I had to go through all my notes and highlights to create a digest in the form of a Google doc that detailed, by chapter, all the important points in bullet format. The result was a summary of each book, by chapter. Most were between 5% and 10% of the book’s length, so for a 250-page book I’d have a Google doc of 12–25 pages. Creating a 12–25-page Google doc takes a ton of time.

I read a book a week, so I had to create these digests weekly. In addition, I was publishing a series of blog posts on each book and experimenting with podcasting by creating a series of episodes on each book. It all felt unsustainable, so I didn’t continue.

I’m reflecting on this today, and I realized a few things:

• Too many new things. Creating the podcast was a ton of effort. Creating the book digest was a ton of effort. Writing a blog post series was a ton of effort. Taking on all these new activities at once likely contributed to it feeling unsustainable. I was never able to find a “groove” for any of the three that felt like second nature. I was just trying to get through it all, but I never felt comfortable with any of it. In hindsight, I should have started with one, gotten that under my belt, and then moved to another.
• Synthesis enhanced my understanding. Creating those digests, which were the foundation for the blog post series, forced me to read analytically. Doing so led to a deeper understanding of what I was reading and helped me uncover more insights and achieve a level of retention I hadn’t experienced since college. When I stopped creating digests, I got less from the books I read. In retrospect, this step, which felt painful, was tremendously beneficial.
• AI can’t save me. I thought I could use AI to help me. My idea was that I could feed AI my highlights and notes from a book and it could create a digest for me. I now realize that this detracted from my understanding of what I read. Reviewing and synthesizing my highlights and notes to create a digest wasn’t fun, but it enhanced my understanding by forcing me to think more deeply about what I’d read. I had to identify the book’s key points, evaluate whether I believed them, and determine whether they supported the book’s main arguments or ideas. Outsourcing that to AI would get me a digest quicker, but I wouldn’t learn, understand, or retain as well—which is the whole point of reading these books to begin with.

I’m really glad I’m doing this Thanksgiving challenge now (see here). I think it’s the start of my figuring out how to sustainably synthesize and share what I learn from books. I’m not trying to check boxes; I’m trying to learn as much as possible from the books I read and share it openly so others can learn too. That’s something I’d strayed away from a bit, but I’m laser focused on it now.

Every holiday I like to give myself a challenge. In 2023, I read an 800-page book during the Thanksgiving break (see here). I’m definitely not doing that again, but I want to continue the tradition and challenge myself. I spent last weekend thinking about what the challenge should be.

Since spring 2024, I’ve been developing the habit of reading a book every week. That’s pretty ingrained now; it feels like second nature. What I haven’t mastered is consistently synthesizing what I learned from each book. I did a series of posts on some books (see here), but that habit wasn’t sustainable.

I now think that synthesizing doesn’t have to be creating a full digest of each book. It can be any of the following:

• Implementing a framework or idea by applying it to a problem (see example here)
• Describing the ideas that resonated with me and why I think they’re valuable (see example here)
• Summarizing a book

That isn’t an exhaustive list, but you get the idea.

I want to make sure I’m learning from these books and that what I learn sticks. One of the best ways I’ve found to make this happen is to share what I’ve learned.

So, my challenge this Thanksgiving holiday is to synthesize what I learned from three books in separate posts. Hopefully, this will help with synthesis after I read and make it second nature.

Wish me luck!

As I added books that I read years ago to the library section of this site, I realized that I didn’t retain a lot of what I read. That makes sense, given that I read some of them seven years ago, in 2018. But I want to retain more of the important concepts and ideas in the books I read. I try to review my notes from books, but that hasn’t been effective because I haven’t been consistent and intentional about digging them up and reading them.

I’m starting to think that reviewing things I’ve learned by rereading them isn’t the best method. To read, I have to focus and not be doing anything else, which means carving out time to do it. That’s proven to be easier said than done.

I’m starting to think that although reading is a good way to introduce a new idea or concept to my brain because I’m focused and able to fully absorb it, it isn’t the best method for later review. Audio might be better. I can listen and do things at the same time, and I can easily fit that kind of multitasking into my schedule. The audio doesn’t have to be super in-depth—just enough information to spark my recollection of a concept.

I’ve been thinking about this more. I’ll try to test it to see if my hypothesis holds up.

This week I heard multiple people compare the current AI revolution to the period when the internet was introduced in the ’90s. One was an accomplished entrepreneur I had a conversation with. Another, a seasoned VC investor who founded his firm in 1994 and has ridden the wave since, was on a podcast.

One of my takeaways from both conversations was that the internet introduced a new technology paradigm that reshaped society and led to a financial gold rush that lasted decades.

All of this got me thinking. I’m curious about how the cycles around new technologies work and how to identify what stage of a technology cycle you’re in. I have a rough idea, but not as detailed an understanding as I’d like. I’m going to look for some historical books on this topic to help fill my gaps.

I used to journal first thing in the morning. I gained a lot from the process and thoroughly enjoyed it. But my routine has since changed—the first thing I do in the morning now is read a book. I’ve been thinking about how to incorporate some form of journaling into my day, and this week I started testing something new: voice recordings.

When I take my daily walk, I’ve started recording what I’m thinking about and what lessons, if any, I learned that day. I didn’t have any expectations when I started doing this, but I’ve been surprised by how much I enjoy the process—specifically, being able to listen to my lessons as I walk. It’s also a daily feedback loop that allows me to listen to and critique how I communicate my thoughts.

It's low tech, which I like: just a phone, Voice Memos app, and EarPods. The one thing I do miss is being able to read my thoughts in a written journal format. I’m sure I can turn these recordings into clean docs with AI. I’ve chatted with a buddy who’s done this, and he gave me some useful tips and ideas on how to write the prompt to achieve this.

Looking forward to using AI to help with this. If it all works as I envision, I may have created my new digital journal.

The more I read biographies, the more I learn about different historical periods. The early 1900s are fascinating, especially the 1929 stock market crash and its economic and psychological impact on society. Another interesting time that I keep reading about is the late 1960s through the early 1980s.

That was when inflation skyrocketed to double digits, resulting in the federal funds rate reaching roughly 20%.

This period had a profound impact on entrepreneurs, investors, and society. I want to understand what led to its extremes and how entrepreneurs and investors navigated them. I’ve heard stories from my parents about 18% rates on mortgages in the early 1980s, but I want to go deeper.  

To learn more, I’ll read a few books about this period and reread books that contain context about it and how people navigated it. I’m also going to reread the letters Warren Buffett wrote to investors in his hedge fund (pre–Berkshire Hathaway), given that he announced he was closing his hedge fund in 1969, the start of this volatile period.

I’ll likely have to read some political and monetary history books—obviously not my usual entrepreneur biographies—because I think it’s important to gain context about the period.

I’m curious about the late 1960s through the early 1980s  and excited to learn about that time in history. My gut tells me it has valuable lessons to teach that could be useful to entrepreneurs and investors in the not-so-distant future.