I came across an interesting quote today from Winston Churchill that stuck with me:

The farther back you can look, the farther forward you are likely to see.

I’m no history buff, but I have spent time studying select historical events related to concepts I want to master. Doing so has helped me connect the cause-and-effect dots. That, and historical context, improved my thinking about what future scenarios are possible and their likelihood. The future is unknowable, but understanding the past helps me understand what could happen in the future, better prepare for those potential scenarios, and navigate them more effectively.

Over the last few weeks, I’ve been learning about a new topic. Part of that effort has been seeking out credible people who deeply understand it. It’s not always easy to figure out who deeply understands a particular topic. I’ve noticed that finding the first person can be a challenge, but once you do, they’ll usually lead you to others.

YouTube has been a helpful source. I’ve been able to find videos of interviews from fifteen years ago up to today for some of these people. This has been an efficient way to evaluate people and learn the new topic. When I’m comfortable that someone is a master of the topic, I’ll watch as many interviews of them as possible and buy any books they’ve written on the topic. 

Six months ago, I began experimenting with a new schedule. I wanted to be more intentional about how I use the time when my brain is most productive (mornings). Specifically, I wanted to read long-form writings (books, papers, etc.) when I first wake up instead of exercising. (I still exercise, but usually at lunch or in the afternoons.)

This change has had a much bigger positive impact than I anticipated. A few takeaways:

• Optimized learning – My brain absorbs new, and sometimes complex, concepts better in the morning when it’s fresh. After reading something new, I think about it throughout the day and sometimes have a new insight. I don’t do mindless or busywork activities when my brain is fresh.
• Relearning how to read – I took time to study the most effective way to read. I’m now more intentional about focusing on a single concept I want to learn about and seeking out books by those who have mastered the concept (or have a superior understanding of it). I read these materials with the intent to understand the critical part of their argument, not the supporting details. This has accelerated the pace at which I read and understand a concept. After I understand one concept, I move to the next concept and repeat the process.  
• Pace – I finish books much faster, which means I’m learning much faster. 
• Habit – Reading first thing in the morning has established a habit that is second nature now. My brain expects to learn something new every morning.
• Book list – I've found that as I’ve accelerated the rate at which I consume books, I've also accelerated the rate at which I add new books to my reading list.
• Challenge – I initially set a daily goal for my reading that pushed me. I now regularly hit that goal and will expand that goal to push myself a little harder.  
• Night reading – I still read in the evenings too, but I tend to read historical books, such as biographies. For me, nighttime reading is not optimal for learning new concepts.

This experiment has instilled a new habit into my life that I think will have a big impact in the long run. I’m still tweaking things a bit but should have my approach fine-tuned and daily goals solidified by the beginning of the new year.

A friend recently asked about posts I wrote two months ago summarizing the IPO filings of Instacart and Klaviyo. Specifically, he asked why I spent time reading through hundreds of pages for each company. Couldn’t I have gotten the same understanding from reading summary articles in the financial press—the Wall Street Journal or Bloomberg?

I wanted to determine the strength of each underlying business for myself before they went public. Whenever I’m evaluating something, I aim to come to my own conclusions. Therefore, I try to find first-source data, not interpretations by people removed from the situation. These filings, while long, were great first-source data. They laid out facts and numerical data relevant to all facets of each business, helping me to reach a conclusion about each company with a high degree of conviction. 

I could have saved time by reading summaries in the financial press or listening to the opinions of others. But I wouldn’t have had as good an understanding of each business, might have missed critical things because others overlooked them, and wouldn’t have had strong conviction in the evaluation of each business because I hadn’t done the work myself. 

A handful of books that I’ve read over the years were so insightful and full of wisdom that I marked them as books I must reread. This weekend, I revisited one of them. I read it a year ago and got immense value from it because it simplified concepts I’d been trying to make sense of.

Rereading parts of the book this weekend, I walked away with additional insights. I began wondering why I missed them the first time. The material in the book hadn’t changed, so it had to be something to do with me.

When I first read this book, my understanding of concepts discussed in it was nonexistent. I was green, with a massive knowledge gap that I was trying to fill. Since then, I’ve consumed lots of long-form content to better understand these concepts. Applying that understanding, I’ve reflected on my successes and failures. All of this has given me a better theoretical and practical understanding of these concepts, which I view as my foundation. 

With books that contain an abundance of wisdom, it’s not always possible to absorb all of it on first reading. The wisdom is layered, in a sense. Understanding one aspect of a concept unlocks your ability to understand something deeper about it. Your ability to understand deeply builds on itself.  

Recognizing how this layering effect works, I now I want to make it a priority to revisit books that I thought were packed with wisdom and that were written by people who’ve mastered concepts that I too want to master.

Over the last few weeks, several things have been top of mind for me. I had a feeling they were related, but the connection wasn’t clear, and why they stayed top of mind wasn’t exactly clear either.

This week, I decided to get some clarity by writing about them. I created a document and recorded in it my thoughts about all these ideas. Over a few days, I ended up crystalizing my thoughts about each of them and uncovering a connection between all of them.

I already knew there’s power in writing, and this document reminded me of it. Writing helps me refine my thoughts and uncover connections and insights that I’m not conscious of. The process also better prepares me to orally explain my thoughts to others.

I think of writing as a mental clarity tool that’s accessible to everyone, yet few take advantage of it.

This is my one-hundred-seventy-ninth weekly reflection. Here are my takeaways from this week:

• IPOs – I learned a lot from the IPO filings of Klaviyo and Instacart, and I had some interesting conversations about these offerings. They could have a material impact on public and private tech markets.
• Holiday weekend – Looking forward to a long weekend and Labor Day holiday.

Week one hundred seventy-nine was another week of learning. Looking forward to next week!

This week I read a quote that made me stop and think:

Formal education will make you a living; self-education will make you a fortune.

                                                   ~Jim Rohn

Simple but powerful! Self-education is how people accelerate wealth accumulation (and their life trajectory). As knowledge accumulates, it compounds. This leads to a better understanding of the world, improved decision-making, and unique insights. These benefits lead, in turn, to identifying unique ways to create value. And value creation often leads to wealth.

Self-education is a slow process, but as with any type of compounding, if you stick with it, the backloaded results are outsize when all’s said and done.

I’ve been learning about successful entrepreneurs who happen to be investors—I call them “investor entrepreneurs.” They invest as their full-time profession, but not by working for someone else. I’ve been reading as much as I can about these people, including biographies about them.

 A biography, of course, is written by someone who spends a lot of time learning about their subject—in this case, an investor entrepreneur. They talk to family members and coworkers. They read files. They interview the investor entrepreneur. All to get a better understanding of the life of the person they’re writing about.

Sometimes the author can’t fit everything they learned in the book, or the investor entrepreneur won’t agree to certain information being published. Sometimes these missing pieces of information can clarify what made the person exceptionally successful.

Biography authors sometimes talk about what didn’t make it to print. Whenever I read a well-researched biography, I search for recordings of interviews and speeches the author gave about the book. This simple hack has led to stories and facts that helped me better understand some of the greatest investor entrepreneurs.

One of my personal goals is to acquire knowledge daily. I focus on knowledge related to concepts I want to better understand so I can attempt to develop unique insights about them.

One of my favorite tools for consuming knowledge is YouTube. I subscribe to the premium membership to avoid ads and to access extra features. I start by deciding what concept I want to understand better. Then I identify people who have a deep understanding of it and search for videos of them sharing their knowledge. I add those videos to my watch list. During my daily treadmill walk, I watch these videos (usually at 1.5X speed to challenge myself). I’ve found that consuming videos while walking is the best fit for me. It feels productive, as I’m exercising and learning at the same time.

I’m a fan of the YouTube platform. It’s been a helpful tool in my quest to learn daily.