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I share what I learn each day about entrepreneurship—from a biography or my own experience. Always a 2-min read or less.
What I Learned While Reading 52 Books in 2024
2/26/25 Update: I created a page with all 52 books I read last year. See it here.
2/27/25 Update: I’ve created a searchable library of every book I’ve read and update it weekly. See it here.
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!
How One Entrepreneur Uses AI to Run His Life
Today I had a conversation with a friend and entrepreneur about how he works. He described his system, which relies heavily on an AI assistant that he chats with daily. He graciously showed me what he built and how it all works.
I won’t get into all the specifics, but a few things stuck with me:
- MCP – He’s using model context protocol (MCP) to connect all his various tools to Claude’s AI assistant so the assistant has proper context around what’s important to him.
- Database – He stores everything—contacts, goals, etc.—in a Notion database, which Claude accesses via MCP.
- 10 items max – In any given day, Claude gives him no more than 10 action items to focus on getting done.
- Specialization – He built a different AI assistant for each part of his life (work, personal, etc.). Each acts according to specific instructions and accesses the appropriate data in a Notion database.
- Update permissions – He gives Claude update permissions so it can update his calendar, his Notion database, and other systems it has access to.
I was impressed with his setup. He’s leveraging AI to manage various aspects of his life and help him pinpoint what to focus on every day.
Automate Everyday Work by Connecting AI to Your Tools
Today I read a blog post (see here) that had caught my eye. It was supposed to be about how to create a personal customer relationship management (CRM) system. Like a lot of people, I struggle to maintain relationships, so I gave it a read. The article turned out to be more than I expected. It’s a great read for anyone trying to understand how to use AI to help with manual tasks and how AI can connect with various tools you already use.
It presents a high-level overview of how you can use AI to talk to the tools you commonly use (Slack, Calendar, Gmail, Google Sheets, Notion, etc.) using the model context protocol (MCP). It describes how MCP works, who created it (Anthorpic), and how the average person can easily download and use it. MCP is powerful because most manual tasks involve shifting between systems. MCP connects all those systems to an AI assistant like Claude, empowering the AI to see the same data you do and execute on it just as you would. You can have an AI assistant complete tasks that would have taken you tons of time or energy, or you can have it do 90% of the work so you have to do only 10%.
The author then takes it a step further and shows you, pretty much step by step, how to use MCP to connect to Gmail and Calendar. It then provides example prompts for instructing AI to do tasks that you’d normally have to manage manually in a CRM. For instance, the author has AI prepare a list of names, using specified criteria, of people he needs to follow up with. He also has AI analyze his calendar for the past week and summarize all his meetings so he can report to his cofounder on Monday what he’d done that week.
I found this post helpful and will be sharing it. Not everyone needs a personal CRM, but the post does a great job of showing how anyone can use MCP and AI assistants to become more efficient and also explaining how to set it up.
I Replaced Weeks of Work With AI
Last week I was working on a data project. I needed to get information from a website and manually enter it into a spreadsheet. In the past, I’ve used Upwork to find data entry resources to help with this sort of thing, and I did that again this time. But as they worked (I have them do tests before I give them the full project), I soon realized that at the rate they were working, it would take someone weeks to build the spreadsheet and cost several times more than I wanted to pay.
I wanted to be frugal and get this task done faster, so I reached out to a developer friend for suggestions. He showed me how to extract the data using the website’s API instead of the user interface (i.e., webpage). All I had to do was figure out how to parse and store the data. Normally, I’d have a developer do this for me, too, but I turned to AI instead. I cracked open Google Gemini and explained the project. Within minutes, it had written a Google Apps script that I could run. It would take the data returned by the API, parse it, and store the data in Google Sheets. The script required one manual step, too, but I was happy to do that. It was very efficient and way less prone to error as compared to someone manually doing it over a few weeks. So, I spent the weekend using the script, Gemini, and the website’s API to build a large data set.
In the end, a project that was projected to take weeks, cost a significant amount, and require me to manage another resource was instead completed by me (with help from Gemini) in several hours over the weekend.
Once people realize they don’t need developers to write code and can build things on their own with AI tools, we’ll see an explosion of people building tools to solve their own problems (and do their jobs more efficiently).
Early Signs: Founders Piece Together How to Work
Last week, I shared (see here) that I was curious about how entrepreneurs learn to work. My thesis is that many don’t know how to work, and the ones who do are self-taught out of necessity. In the last few days, I’ve talked to a few entrepreneurs and asked these point-blank questions:
- How do you decide what to work on each day?
- What did your last workday look like?
- What did your last workweek look like?
- How did you learn how to work as a founder?
The first three questions are to understand how they work. The last question is the most important one.
I’ve done only a handful of these sessions, but so far, the answer is that they learned over time by piecing together what people shared with them. Also, the forcing function was stress and anxiety, which made them realize that how they were working was a big problem.
It’s early days, and I’m curious. I’ll have more of these conversations with entrepreneurs. This might be an overlooked problem that many entrepreneurs face.
Weekly Update: Week 303
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: 98
- Total blog posts published: 651
This week’s metrics:
- Books read: 1
- Blog posts published: 7
What I completed in the week ending 1/18/26 (link to the previous week’s commitments):
- Read The PARA Method, a framework for implementing the PARA Method from Building a Second Brain
What I’ll do next week:
- Read a biography, autobiography, or framework book
- Write a post sharing what I learned from synthesizing The Art of Execution
Asks:
- No ask this week
Week three hundred three was another week of learning. Looking forward to next week!
What I Learned Last Week (1/18/26)
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:
- Same as last week: I had trouble getting started on synthesizing another book. I need to make more changes to my approach.
What I learned:
- No material learnings related to this project this week.
That’s what I learned and struggled with last week.
Most Entrepreneurs Are Never Taught How to Work…They Learn The Hard Way
Yesterday I shared (see here) that a friend who is an entrepreneur learned how to work—meaning how to work efficiently and consistently to meet goals—while employed by a large corporation known for its world-class training. That’s more the exception than the norm, in my opinion. Most people don’t get world-class training on how to work. That got me thinking about myself—how did I learn how to work?
Thinking back, this isn’t something I was ever taught. Not in college and not in corporate America. After I became an entrepreneur, I felt like I was drowning in a never-ending to-do list. I was stressed out. That pain helped me realize that how I was working wasn’t sustainable or effective. So, I sought out other entrepreneurs and asked them how they worked. Over time, I pieced together a system that worked to some extent. But it wasn’t until years later that I read books on the topic that helped me understand what a methodical approach to work looks like and how to implement one.
Now I’m curious. How do most entrepreneurs learn how to work? I don’t know the answer, so I’m going to ask a few and see. My gut tells me that many don’t know how to work and are stressed out—and that those who do know are self-taught out of necessity. Let’s see if I’m right.
Nobody Teaches You How to Work
This week, I caught up with a friend who’s an entrepreneur. During our chat, I inquired about how he works. How does he determine what he’s working on each day? How does he know what needs to be done for each objective or project he’s working on? You get the idea. He said that he learned how to work—meaning he learned the process of working efficiently and consistently—while employed by a large corporation known for its world-class training. But that was a few decades into his career.
What I took away from this conversation is that most people are never taught how to work. They’re taught skills, and they gain expertise. But they’re never taught how to effectively execute their skills from day to day to accomplish goals or objectives. Instead, they try to remember and manage everything in their head and end up stressed or burnt out as their responsibilities at work and home increase.
To take this a step further, entrepreneurs experience many times more pain than the average person because of not knowing how to work. They often start out by doing literally everything in the business—much of which they have zero skills or experience in. Over time, many of them experience high levels of stress and anxiety because of this, which causes other problems.
My big takeaway is that the costs of never being taught how to work are high, especially for entrepreneurs.
Howard Marks: The Secret to Great Partnerships
Yesterday, I shared an interview featuring Howard Marks and his four steps to dealing with change (see here). Toward the end of the interview, Marks talked about his partnership with one of his Oaktree Capital cofounders, Bruce Karsh. He described partnership as an important part of a healthy work environment, which he has with Karsh and other Oaktree Capital founders.
So what’s the key to healthy partnership? Marks has a simple framework. Here’s the key to a healthy partnership (in all aspects of life):
- Shared values – You have to believe the same things about how you want to operate in the world. Marks gave the example that he and Karsh shared the view that they should invest by seeking moderate gains and avoiding losses. Said differently, they would aim for consistent returns rather than grand slams. Neither believed in shooting for the stars. Their values regarding their investment strategy were the same.
- Complementary skills – The key to success is having a well-rounded team that covers all the important areas—the team is strong in all key areas although each individual is not. If you have a team of really smart people who all specialize in the same thing, the team has a skill set hole that will likely cause execution and other issues. A better approach is to work with people who are strong where you’re weak, so you complement each other. This enhances the team’s ability to execute, and people won’t be stepping on each other’s toes.
I agree with Marks. I think partnerships that have both these things can do well. My gut tells me that many people understand the second point and seek complementary skills—opposites attract. But I don’t think as many people understand how important shared values are in a partnership. If you have complementary skill sets but polar-opposite views on how to go about things, you’re bound to have a day of reckoning and maybe even a huge blowup between partners.
If you’re interested in Mark’s full thoughts on partnership, take a listen here.
