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!

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:

• Keeping the momentum going on projects is important. I lost momentum but got back on track this week with focus video meetings. See more about this here. Lesson learned: don’t lose momentum.
• Diagrams and charts that explain my thinking are helpful to others, especially developers. Creating them forced me to think through things that I might not have if I’d just had to explain verbally. Also, a lot of people are visual learners.
• I want to attend a conference and show the early version of the product to a few people at the conference. This conference deadline has motivated us and forced us to focus on what can and must be done before the conference. Lesson learned: Targeting industry events is a way to heighten focus and intensity. See more here.
• I need to share my posts about the biographies I’m reading on other platforms. Links on other platforms to my blog posts aren’t effective today.
• SEO is changing a lot. People are using ChatGPT and other AI apps to answer questions instead of going to Google. However, based on my testing this week, many of these AI tools seem to use Google’s search results to answer their users’ questions.
• I pitched the idea a few times this week. The problem statement I crafted over the holiday resonated with and excited listeners. That felt great. I need to trim the wording, but I can clearly state the problem, and people get it quickly.
• When Google’s Gemini releases new models, it doesn’t always make them available via API. The Gemini 2.0 Flash Thinking Experimental model just got released and is impressive. I’m using it for personal things, and I love it. We tried to use it via API for this project, but there isn’t an API for the model yet.

Those are my struggles and learnings from the week!

A few weeks ago, I read The Money Masters: Nine Great Investors: Their Winning Strategies and How You Can Apply Them by John Train. The book introduced me to T. Rowe Price, and I read his biography, too (more here). I really enjoyed learning a little about several people from a single book. I decided to make biographical anthologies a bigger part of my reading and discovery strategy (more here).

This week, I’m reading another book by John Train, Money Masters of Our Time, and I’ve been reintroduced to another investor I want to learn more about. Julian Robertson founded Tiger Management. I learned about him two years ago while exploring an idea for a studio for venture capital managers. During my research, I was lucky enough to get connected to someone who worked in Robertson’s back office during his heyday who explained to me how the operation ran with the Tiger Cubs.

Robertson was a successful hedge fund investor, and he also seeded and incubated tons of investors who wanted to start their own investing firms. These budding investor entrepreneurs worked out of his office and were known as the “Tiger Cubs.” The list of people Robertson helped in this way is impressive; it includes well-known investors such as Chase Coleman of Tiger Global and Philippe Laffont of Coatue Management.

I think Robertson pioneered a model of seeding and incubating budding investors that’s needed today. The model is clearly lucrative, as Robertson’s economics in the firms of some of his successful Tiger Cubs made him another fortune.

I want to learn more about Robertson, so I’m going to see if I can find a biography of him.

One of the things I want to do is expand the reach of the content I share on my blog. I’ve been studying marketing for the last few months (see here), and I’ve learned that a big part of marketing is making people aware that something exists. I figure my blog content is a good way to do some more learning by doing.

One thing I noticed and have read about is that people are now posting blog-type content directly on platforms instead of directing them back to their website. Instead of sharing a link to their blog, they’re posting the blog content directly on X (formerly Twitter) or LinkedIn, for example. Apparently, if your post includes a link to content off the platform, the platform’s algorithms show that post to fewer people.

Learning this reminded me of how I started. When I began blogging in March 2020, I wanted to start in as frictionless a way as possible. I didn’t have a blog site, but I did have a LinkedIn profile. LinkedIn allowed you to post “articles,” so I started sharing my daily posts as LinkedIn articles. Those did well because of my built-in LinkedIn connections. After my writing habit was fully formed months later, I bought a domain, designed a website, transferred my old posts to the website, and started posting daily on both platforms. Then, I stopped sharing content via LinkedIn articles and started creating posts that linked back to my blog site. Eventually, I stopped LinkedIn altogether after about two years and posted exclusively on my blog.

Well, I want to test some of the marketing tactics I’m learning by helping my blog content reach more people, so I’ve been debating posting my content on other platforms. Basically, I’ll start doing what I used to do. I’m familiar with LinkedIn, so it makes sense to start posting there again. I want to learn X, so it also makes sense to post there.

The concern is that I’ll have to manage posting on three platforms—my blog, LinkedIn, and X—every single day. One is fine, but three I’m not sure about. I’ll continue to ponder it a bit, but maybe instead of going from one to three, I should go to two and then move to three after I’m comfortable with the second platform.

The last few weeks have been full of distractions. It snowed twice in Atlanta, shutting the city down. Before that were the holidays. Traction on software development of my personal project slipped. A developer friend is helping as a favor. All of the above, plus other stuff, impacted our ability to schedule time to work in person on the project.

With snow forecasted for this week, we made a change to get going again. We couldn’t meet in person, so we decided to try a video meeting instead. But we didn’t want to have sessions where we talked. We wanted to have sessions where we got stuff done. So here’s what we did:

• We booked two-hour blocks to meet over video twice this week.
• Beforehand, we defined what we would each do during the working sessions.
• If my friend’s work depended on my completing something, I did it in advance so he wouldn’t be blocked during our session. And vice versa.
• At the end of each session, we discussed, and demoed if applicable, what we worked on.
• And we discussed what we would work on during the next session and what needed to be completed beforehand.

During our working sessions, he wrote software, and I fine-tuned class diagrams, workflows, etc. Our work didn’t overlap unless we had a question. This is where the benefit of this working style became clear to me. Instead of stopping what I was working on, sending an email or text to him, waiting for a response, and restarting work hours or a day later, I could get an answer instantly and keep working. Of course, this was true from his perspective too.

There are a few names for this type of work. Some call it “parallel working.” My developer friend called it “pair programming.” Whatever the right name, I’ve never tried it before this week, but so far, I’m a fan. We were able to get a lot done in a short time.

I was thinking about why the sessions were so effective. A few things stood out to me:

• People block out focus time on their calendars. These sessions are the equivalent of scheduled focus time on a specific project, but for a team.
• Friction and blockers are removed as soon as they arise, so more continuous work gets done.
• There’s an increased level of accountability. You can’t BS during these sessions.
• The work is planned beforehand, so sessions are execution focused, not discussions or attempts to figure out what to work on. I think this is a big reason this works so well.

I’m happy my friend suggested we work like this. I feel like it’s time spent efficiently. I’m also happy this project is rolling again.

I’ve been making daily learning a top priority for the last few years. Some time ago, I shared how I approach daily learning (see here). That list is still relevant, but the prioritization of the items has changed. I aim to read a biography a week, so that’s the method I focus on most. But I do a lot of other learning throughout the week. For example, I challenged myself to learn the big concepts around marketing (see why here) and have consumed a ton of information. I now have a better understanding of the big marketing concepts and how marketers think.

I’ve recently started creating notes documenting what I’ve learned, and from what sources. I’ve been sharing some of that with founders and friends. They’ve found it helpful. In blog posts, I share what I’m learning from books—but not non-book learning. I want to find a good way to share on my blog the best non-book information I’ve consumed.

I haven’t settled on how to do this, but an idea I’m thinking about now is a weekly list of the top five to ten sources I consumed that week and what I learned from them. I don’t want to keep good information to myself. I want to get into the habit of sharing more useful sources from which others can learn. I just need to figure out how to do it in a way that’s not a huge lift so I can do it consistently. I’m open to ideas. If you have suggestions, send them my way.

I finished reading Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger last week. It’s a memoir and collection of famous speeches by Charlie Munger. I’d put off reading it for a while. Looking back, I regret that decision. The book unlocked a different way of evaluating decisions and exposed me to new psychological concepts—some that aren’t even taught in schools. It felt like an introduction to practical psychology for entrepreneurs and investors. I made tons of highlights and notes while reading this book.

I’ll eventually create a blog series on this book, so I won’t go into everything here. But here are a few more takeaways:

• Checklists – Countless times throughout the book, Charlie mentioned using mental checklists as a way to avoid mistakes in your decision process. Checklists are also a central part of David Allen’s Getting Things Done (unrelated) framework. My takeaway is that checklists are simple tools that are available to everyone, but they’re more powerful than people realize when used consistently.
• Multidisciplinary learning – I mentioned this in my post last week (here). If you have a narrow understanding of topics or a small tool set, you increase your risk of the cognitive bias of relying too much on one tool or a limited number of tools. Mark Twain described it well: “To a man with a hammer, everything looks like a nail.” You apply tools to situations for which they’re not appropriate and increase the chances of making subpar decisions. Broad learning about topics that interest you helps prevent this. Often, you discover nonobvious relationships between topics that others have missed, which improves your decision-making and gives you an edge. Charlie mastered this, and it led to a life of curiosity-driven learning and a billion-dollar fortune from shrewd decisions.
• Hard work – Acting and getting things done is one form of hard work. But learning and thinking is another form, one that many people underestimate. Learning and thinking are preparation. Good preparation leads to better decisions and allows you to practice “extreme decisiveness,” which is valuable during extreme uncertainty. From an investing perspective, preparation allows you to identify when something is mispriced and gives you the confidence to bet heavily based on your work, even if everyone else is selling for dear life.
• Incentives – Incentives heavily influence individual decision-making. Getting them right is critical for entrepreneurs and managers. If you want to understand someone’s actions or thought process, think about how they’re being incentivized.
• Lollapalooza effect – When two or more factors work at the same time, they magnify outcomes. This works positively and negatively. This reminded me of twin tailwinds, which I’ve noticed when reading about Henry Singleton (see here), Warren Buffett (see here), and 2021’s IPO explosion (here). These are lollapalooza-effect examples that led to massive wealth creation.
• Mastering wisdom – Mastering the best things others have figured out is a discipline. It’s also a hack. Trying to figure out everything from scratch on your own is hard to do, and most people aren’t smart enough to do it (Charlie’s words, not mine). It’s better to take what others have figured out and build upon their wisdom. Everyone can do it, but many people won’t because it requires a passion for learning and curiosity and is hard work.
• Inversion – If you’re not sure what to do about a problem, think it through backward to figure out what not to do. By knowing what not to do, you’re one step closer to understanding what to do.
• Outsourcing thinking – You can’t outsource your thinking. You must think for yourself and, ideally, in a multidisciplinary manner.

Those are just some of my takeaways from this book. I’m glad I read it and will likely reread it someday.

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: 46
• Total book digests created: 15
• Total blog posts published: 287
• 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 Poor Charlie’s Almanack: The Essential Wit and Wisdom of Charles T. Munger, a memoir and collection of famous speeches by Charlie Munger
• Picked three types of output and associated user problems and created a lucid chart to document the process flow to solve them
• Created class diagram showing proposed linkages between various classes (tables) in the database
• Documented the required elements for the UI of the MVP

What I’ll do next week:

• Read a biography, autobiography, or framework book
• Get feedback on the problem, vision, and mission statements from two seasoned entrepreneurs
• Create a concise hypothesis statement  
• Share the draft taxonomy with two people
• Continue linking blog posts about the same book
• Continue updating descriptions for blog posts about the same book

Asks:

• None

Week two hundred fifty-one 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:

• Creating a class (database table) diagram for all the links between data classes is hard if I try to draw it on paper from the start. It was easier to walk through one class at a time, defining its relationship with other classes and the type of relationship (one-to-one, one-to-many, many-to-many) with each class. AI helped me through this exercise and created a JSON output that documents all the relationships. I then used the JSON output to create the class diagram.
• The UI doesn’t need to be spectacular for an early version of a software product. It just needs to work. But engineers who aren’t full stack want an example of the UI they should build. Finding examples of UIs from other products and asking a developer to clone one of them (or parts of it) is an efficient way to get a developer what they need.
• Categorizing the use-case types that entrepreneurs will want to use the “book library” tool for was a great exercise. Each type of problem can have a specific, repeatable solution. Creating an approach or framework for each problem type was a nice unlock.
• Thinking about the use-case types as one big process and creating a flow process diagram to document it was a big step forward. The document also fostered alignment between my developer friend and me because he could see how I envision the user flow.
• I need to collaborate with people who complement me, especially in marketing. I had a chat with a friend who’s skilled in marketing. We uncovered some low-hanging-fruit opportunities that could be great ways to drive long-term awareness of this tool organically (i.e., not through paid marketing).
• Headway is a bootstrapped book-summary app founded in 2019. It’s rumored to do over $200 million in annual revenue with 30% profit margins (source). It raised $100 million at a $2.3 billion valuation in 2024 (source).

Those are my struggles and learnings from the week!

Today, I had a good chat with a founder friend. He mentioned an idea that I thought about for the rest of the day. Sometimes, early-stage founders struggle to reach their next milestones. They know what they want to do to get there, but they don’t have the necessary skills. Their weaknesses hold them back, and they can’t afford people with high-level expertise. However, they often know tons of other founders—and some are strong where they are weak. And vice versa.

My friend’s observation was that early founders, especially those who are bootstrapping, may be able to complement each other temporarily. For example, Bob struggles with marketing but is strong in engineering. John is a killer marketer, but nontechnical. Instead of complaining to each other about not being able to afford or find high-level talent to get them to the next milestone, maybe the two entrepreneurs should temporarily partner with each other. Bob helps John with his technical problems. John helps Bob market his software. Again, temporarily.

My friend took this even further and suggested that these two founders not accept cash compensation. Instead, they pay each other with a very small amount of equity ownership in their respective companies. This aligns interests, helps both companies be capital efficient, and allows each to get high-level talent it otherwise couldn’t access (or afford). Again temporarily. Of course, vesting and other things would need to be clearly outlined.

My friend’s thesis was that certain high-level expertise can make a big difference in the early days. It can help you reach those critical milestones, but it isn’t a full-time job. It’s more of a gap that needs to be filled until you have sufficient traction and resources to hire someone full-time. Also, discussing strategy with another founder who has expertise in a critical area makes those strategy conversations richer and results in better ideas and solutions. Lastly, no one goes as hard as founders. Having a founder on your side, even part-time, can be a game changer.