On January 27, 2020, I had lunch with an entrepreneur friend. He encouraged me to share what I’d learned from scaling my bootstrapped company to over $10 million in annual revenue. I’m private and was reluctant, but I wanted to help others who were just like me when I started my company—people who didn’t know what they didn’t know. I agreed, and we began a 60-day challenge. We both posted content daily to help other entrepreneurs (see our challenge details here). That challenge began on March 9, 2020, and ended on May 10, 2020. I didn’t miss a day—and I learned to enjoy the habit of reflecting and writing every day.

That was five years ago. Since then, I’ve written and shared a post every single day. That’s over 1,825 consecutive days of sharing my thoughts. When I agreed to the challenge, I had no idea I’d still be posting five years later, but I’m glad I am.

Every March, I reflect on my writing journey. Here are a few reflections:

• Strike zone – I read a book a week, mostly biographies. I used to think of reading and writing as independent hobbies. But writing about the books I’m reading has enhanced my learning and thinking. Combining them feels like it’s put me in my strike zone.  
• Format – I’ve played with a few different formats for creating posts about biographies I’ve read. The format I like best is a deep-dive series about a biography (see examples here and here). I’m aiming to get back to that format, and I’m building software to help with the creation process.
• Luck – Bringing value to others by writing has increased my luck surface area and led to magnetic luck (more on luck types here). When I focused more on writing about biographies, it led to more magnetic luck. Entrepreneurs want to know what other entrepreneurs have figured out but don’t always want to read an entire book.
• Audio – Last year, I tested doing a solo podcast about the books I was reading. It was really an audio version of this blog. I did 100 episodes to get reps and learn. Audio is a powerful format but requires significantly more work than writing. Publishing a podcast episode daily wasn’t sustainable. I’ll revisit doing a podcast, but I’ll need more support next time, and I’ll test different formats.
• Level up – I want to take this blog to the next level and create more value for others. Adding a page detailing all the books I’ve read and creating a profile page for each book (see here) is an experiment and just the beginning.
• Annual contract – Every March, I’ve asked myself if I’m enjoying this and want to keep doing it. If yes, I re-up for another one-year contract with the option to renew. I’ve now signed through 2026.

Those are my reflections. I’m looking forward to the next year. I feel like year six will be epic!

This summer, I set a goal of creating 100 podcasts about books I was reading. It forced me to start tracking my reading in a spreadsheet. It’s nerdy, but it was necessary because every week, I read a book, wrote a blog post series, and created a podcast series about each book. The spreadsheet helped me keep everything organized. I paused the latter two after the summer because they were too inefficient and time-consuming, but I kept updating the spreadsheet and reading a book a week.

I looked at the spreadsheet as I was reflecting on the books I read in 2024. I figured I’d share some stats and learnings.

High-level stat for 2024:

• Books read: 52

2024 breakdown by month:

• January: 0 (I did read, but I can’t remember what books)
• February: 2
• March: 6
• April: 6
• May: 7
• June: 5
• July: 4
• August: 5
• September: 4
• October: 3
• November: 5
• December: 5

Here are a few things I learned along the way:

• Reading two books a week was too aggressive. I tried it in the March–May period, but I wasn’t absorbing as much of what I was reading or making as many connections. I was focused on finishing the books, which isn’t why I read. The pace was too fast, so I reduced it to a book a week, which feels more sustainable.
• Sharing what I learned from my reading was the big unlock. It took my learning and thinking to another level. Writing a blog post series and recording a podcast series forced me to identify insights and organize and communicate my thinking. The key tool in that process was creating a digest of each book, which was an extraction of the information I found important in each chapter, along with my insights.
• E-readers, such as Kindles, are great devices, but I prefer reading physical books. I highlight and add notes about insightful sections and ideas in the books. Those highlights and notes are trapped in each book, so finding and using them later is difficult. See here for more. As I’ve read more, this has become a painful problem. Trying to find something sometimes means reviewing several books’ notes and highlights. Experiencing this pain led me to several feature ideas for the “book library.”
• Reading a book is simple—but learning from what I read is more involved. It’s inefficient and involves lots of steps. The process of sharing what I learn from my reading is complex. It’s hard and has many steps and lots of moving pieces. This realization led me to add several more feature ideas to the “book library.”
• The value in reading lots of entrepreneurial biographies is that you’re exposed to the best ideas and experiences of entrepreneurs, and you can pull from them when you’re faced with a problem. The challenge is that this requires a great memory or knowing exactly where to look to quickly find something you’ve read. I don’t have a photographic memory, and I don’t always remember where I read something. I want to make it easy to find what I’ve read, which will be a big part of the “book library” MVP.
• My best ideas in 2024 came from piecing ideas together from various books. Making those connections was a great way to build upon what other entrepreneurs figured out. Solving a problem by building upon the knowledge of others rather than starting from scratch led to my having better ideas. I’m not an idea guy, so this was perfect for me, and I want to do more of it going forward. I don’t think this has to be completely manual and inefficient. Figuring out how to solve this and incorporate it into the “book library” is challenging, but I think it can be done, and I’m excited to figure this out because it’ll be a huge unlock for myself and others.

Those are my takeaways and reading stats for 2024!

2/26/25 Update: I finally published a list of all 52 books. You can see the list here.

2/27/25 Update: I created a searchable list of all the books I’ve read, and I’ll be updating it weekly. See here.

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: 54
• Total book digests created: 15
• Total blog posts published: 343
• Total audio recordings published: 103

This week’s metrics:

• Books read: 1
• Book digests created: 0
• Blog posts published: 7
• Audio recordings published: 0

What I completed this week (link to last week’s commitments):

• Read Empire: The House That John H. Johnson Built, a biography about publishing entrepreneur John H. Johnson
• Got feedback from five people regarding alternative layouts for a list of entrepreneurs on my blog
• Selected one of those layouts

What I’ll do next week:

• Mainly, focus on helping my family resolve the medical situation
• Read a biography, autobiography, or framework book
• Make it possible for software to be hosted in the cloud instead of locally

Asks:

• If you know any full-stack developers interested in working on the software for my current project, please introduce us!

Week two hundred fifty-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:

• No material struggles this week

What I learned:

• This week, I helped one of my parents with a medical situation. I learned a ton about medicine, but not much related to this project.  

Those are my struggles and learnings from the week.

A friend sent me a video 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.

Karpathy shares lots of good info in his video, but it was one use case that prompted my friend to send it to me—and that stood out to me. Karpathy uses LLMs to help him read and understand books and research papers. Here are my takeaways:

• Nowadays, Karpathy mostly reads books using LLMs.
• Here’s his process:
  • Pull up the content (i.e., text) of the book.
  • Find the chapter he’s going to read.
  • The LLM likely knows what the book is about but won’t remember what specific chapters are about.
  • Remind the LLM about the chapter by pasting the chapter text into the LLM context window.
  • Ask the LLM for a summary of the chapter.
  • Read the summary.
  • Read the chapter.
  • If he has questions about what he’s reading, ask the LLM those questions.
• Reading a book with an LLM dramatically improves his understanding and retention of each chapter. It enhances his ability to understand material in fields he’s unfamiliar with or books written long ago.
• No tools exist that make it easy to do this, so he uses a “clunky and back-and-forth” process.
• He mentions that having the ability to highlight text and ask questions about the highlighted parts doesn’t exist but would be useful.
• Final thought: Don’t read books alone.

I’m glad my friend shared this video with me. It was useful to hear a detailed explanation of how someone leverages LLMs to understand book content. Although he has extensive experience with LLMs, his process is still cumbersome. The fact that he’s following this cumbersome process tells me that the value he’s getting from it must be immense.

The software I’m building will greatly enhance my understanding of the books I read with LLMs. Karpathy’s video confirmed I’m going in the right direction, that other readers are leveraging LLMs, and that they’re experiencing pain when doing so.

If you want to see this section of Karpathy’s video, it’s here. If you want to watch the entire video to see how he uses LLMs in life and work, see here.

Early this year, I read the updated version of Poor Charlie’s Almanack, a collection of Charlie Munger’s speeches on mental models and psychology. The book was a masterclass on decision-making. Since then, I’ve reread sections of the book and found recordings of the speeches. What Charlie Munger shares in those speeches is knowledge and insight that he spent decades acquiring. His wisdom feels like a cheat code, and I want to leverage it fully.

I wanted a cheat sheet of Munger’s wisdom to reference as I make decisions. During my research, I found something pretty helpful. It’s an animated video that condenses the most important lessons from Munger’s 1995 speech “The Psychology of Human Misjudgment,” which lasted about 75 minutes, into 14 minutes.

Tiny, a publicly traded Canadian holding company that acquires and owns businesses long-term, created the video. Here’s what its cofounder, Andrew Wilkinson, said this week in his newsletter about why they created the video:

In 1995, Charlie Munger, Warren Buffett’s longtime business partner, gave an incredible speech about why humans do stupid things.

In it, he breaks down all the key psychological effects that warp our thinking and cause bizarre behavior.

In 2014, I made it my mission to memorize this talk. I listened to it every single day on my drive to work and tattoo’d it into my brain.

It has been one of the most durable and important pieces of content I’ve ever consumed, and a few years ago, Chris and I decided to make it more accessible.

We took the original hour long scratchy audio recording and turned it into a shorter and more accessible animated video.

I’ll still create a cheat sheet, but I’m going to test Wilkinson’s approach and listen to this video daily to see if doing so accelerates my understanding of the concepts Munger discussed in this speech.

If you want to watch the 14 minute animated version of Munger's speech, you can find it here.

One of my favorite entrepreneurs is John H. Johnson. He was a publishing entrepreneur who created Ebony and Jet magazines. Both were iconic magazines in the Black community for several decades. Johnson bootstrapped his company, and by 1987 it was doing over $174 million in annual revenue—almost $481 million in 2024 dollars. Johnson’s autobiography was one of my favorite reads last year. I bought several copies and wrote a five-part deep dive on it (see here).

I wanted to learn more about Johnson and found Empire: The House That John H. Johnson Built, a biography of him. It was written by Margena A. Christian, who used to work at Johnson’s Johnson Publishing Company.

I’m still reading the book, but a few things have caught my attention:

• Start-up capital – Johnson “borrowed” the customer list (20,000 names) of the insurance company that employed him. He then wrote a letter to every customer asking them to prepay for a subscription to a magazine he hadn’t created yet. Three thousand people agreed to pay $2, giving him $2,000 in start-up capital—more than $100,000 in 2024 dollars. This biography highlighted Johnson’s copywriting in that letter. He worded the sales letter in a highly effective way and made people want to buy, sight unseen. Johnson noted that this letter was so unique that he could never replicate those results.
• Curation – Johnson’s first magazine, Negro Digest, didn’t include any original articles. He aggregated all its articles from various publications about Blacks. Making information readily available in a single place made his first magazine successful.
• Cloning – Johnson didn’t try to reinvent the wheel or create something new. He “borrowed” from successful magazine formats and used them to communicate to the Black community. Life magazine was a picture-based magazine that was wildly successful. Johnson used that format when he launched Ebony magazine.

Those are some of my early takeaways from the book. I’m looking forward to reading the rest of it.

My developer friend has been helping me, nights and weekends, to build the first version of my software. He has his own start-up but was intrigued by the challenge of my project and took it on as a side project. It’s been a great experience; we’ve both learned a ton. He’s deep into artificial intelligence (AI) and building systems to manage large data sets, so he was a terrific fit. It was great to have someone with the right technical experience who could complement what I envisioned. We should have a hosted version of that first product version done this week.

My friend’s start-up is hitting a critical point, and he has less free time, so he won’t be able to devote programming time to my project going forward. I’m appreciative of what he’s contributed thus far. His expertise led to some valuable insights. In the beginning, we had a candid conversation and set clear expectations; we agreed this day would come eventually, and here it is.

He’ll still help with my project, but it will be more high-level as time permits. That being the case, I need to find a developer who can help us knock out the last few features I envision for this project so others can play with it. If you know a talented, full-stack developer interested in building the Bloomberg Terminal for entrepreneurs, let me know. A love of reading books is a strong plus.

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: 53
• Total book digests created: 15
• Total blog posts published: 336
• Total audio recordings published: 103

This week’s metrics:

• Books read: 1
• Book digests created: 0
• Blog posts published: 7
• Audio recordings published: 0

What I completed this week (link to last week’s commitments):

• Read The Man Who Sold America, a biography of advertising entrepreneur and political strategist Albert Lasker
• Published a profile of the above-mentioned book on my blog
• Completed follow-up with contacts from Newsletter Marketing Summit

What I’ll do next week:

• Read a biography, autobiography, or framework book
• Make it possible for software to be hosted in the cloud instead of locally
• Get feedback from five people regarding alternative layouts for a list of entrepreneurs on my blog
• Pick layout for list of entrepreneurs and test live page with real data

Asks:

• If you know any full-stack developers interested in working on the software for my current project, please introduce us!

Week two hundred fifty-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 this week

What I learned:

• Entrepreneurs who prefer listening to books struggle to create voice or written notes about important parts of books or their thinking around parts of the book they’ve listened to.
• It can be difficult to remember to review an annotation from a book. An entrepreneur requested the ability to set an automated reminder that prompts him to do so.

Those are my struggles and learnings from the week.