I like to keep my finger on the pulse of new technologies and emerging trends, but it’s easier said than done. One of the ways I do it is by catching up with early-stage founders who are building in that space. The founders in the early days of launching a company are typically as close to ground level as you can get. They’re usually hands on keyboard and in the weeds of everything. Hearing how they’re applying new technologies and what positives and negatives they’ve experienced helps me understand things from a practical perspective. I also try to make sure these conversations are bidirectional by providing feedback on anything that’s on the top of their mind (that I can help with).

I’ve found that this is a great approach to staying abreast of new things and maintaining relationships with and giving back to early founders.

A few months back, I purchased a book that was recommended by several investors who’ve had outsize success over a long period of time. I typically buy a book only if credible people recommend it and the Amazon reviews are 4.5 stars are higher. This book fit both criteria, so I quickly ordered it.

When I received the book, I realized two things. It’s 800 pages long, and it was first published almost a century ago. Both facts made me cringe. I generally read books of 300 pages or less. In my experience, the longer the book, the more fluff it contains. I enjoy books that get their points across succinctly. With verbose books, my attention wanders. I also personally don’t enjoy books written long ago because the writing style is so different. It can be a struggle for me to grasp the authors’ points because I’m not used to that way of writing. I put the book on the shelf to read later. That was months ago, and I haven’t touched it.

This book is so well regarded that I don’t want to keep putting it off or, worse, never read it. Today I set a goal: read this book by the end of the Thanksgiving weekend. That means I need to read all 800 pages by November 26. Setting this challenge for myself reenergized me in relation to this book. I can’t wait to hit this goal and learn the insights in it.

Early in 2023, I challenged myself to read more SEC filings of publicly traded technology companies. I’ve been reading S-1 initial registration reports for companies preparing to go public for several years. This year I’ve incorporated 10Q quarterly reports and 10K annual reports into my reading. I wasn’t sure when I began whether it would be worth the time and energy, but I figured I had more to gain than lose by trying it. 

Here are my takeaways:

• Financials – The company’s financial performance is laid bare in these reports. The good, the bad, and the ugly are there for everyone to see. Some company financials are complex; others, simple. Interpreting what the numbers mean sometimes requires work. It isn’t always fun, but once I figure it out, I’ve usually learned something useful.
• Business model – Companies detail their inner workings and how they generate revenue. They share all kinds of interesting tidbits, such as plans for future revenue sources and concerns about the stickiness of current revenue. I usually got lots of ideas after reading the specifics of a company’s business model.
• Risks – Companies detail all risks associated with the business. This is basically a list of what keeps the CEO up at night. Sometimes the risks listed surprise me.
• Competitors – Most companies list their top competitors.
• Trends – After I’ve read multiple reports from a company, I start to see trends and patterns (good and bad).
• Executive compensation – Executive compensation usually has its own section, with compensation plans described in detail. Large stock option grants based on hitting lofty stock price or market cap objectives seem common in CEO incentive packages.
• Ownership – The S-1, and sometimes other reports, detail how much of the company executives and investors own. Very interesting. Especially if it was VC backed.
• Stock-based compensation – A good number of technology companies have high stock-based-compensation expenses. This is essentially the expense the company incurs for paying employees with RSUs, stock options, etc. I’m curious whether this practice will continue at the levels seen in the last fifteen years, given how much it dilutes the holdings of other shareholders.
• Perception – After reading these reports, I sometimes reach a conclusion about a company that differs from popular opinion in the financial media.
• Dense – These reports are typically long. I can read them only when I’ve got an uninterrupted block of time when I can focus.

The filings of public companies are full of information that entrepreneurs and investors will find helpful. I wish I’d read public filings from companies in my industry when I was building my company. I’m sure it would have positively influenced my thinking and decision making. Anyone interested in reading these reports for their favorite company can search for them on the SEC Edgar website here.

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!