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

• Schedule experiment – I’m almost two months into my schedule experiment. It’s no longer an experiment. It’s a habit now. Dedicating more time daily to reading to acquire knowledge led to my realizing that I was approaching reading the wrong way. I spent time learning how to be intentional about reading, and I began implementing a new approach this week. The early results are impressive. This could have a big impact on me going forward.
• Compounding – Most people think about interest and money in connection with compounding. But it applies to much more in life than money.
• Closing windows of opportunity – Some opportunities won’t be around forever. This week was a reminder to make opportunities with expiration dates—in all aspects of life—priorities. I may not know when they’ll expire, but I know they will and that I need to make the most of them while I can.

Week one hundred sixty-nine was a short but productive week. Looking forward to next week!

I’m a fan of evaluating people by how far they’ve traveled in addition to what they’ve accomplished. Two people may start at the same time and end up accomplishing the same thing, but one may have traveled twice as far because his starting position was much farther back. For example, if you’re evaluating two runners who finished a race in 10 minutes, you surmise they’re equally talented. Now consider that one runner’s starting position was twice as far back: he ran 2 miles while the other ran 1 mile. They both finished in an amazing time, but one runner outworked the other by traveling twice as far in the same amount of time.

My dad is the runner who traveled twice as far. He was born into a great but extremely poor family, in a place with limited economic opportunities, in a less-than-equitable period in America’s history. Through thirty-plus years of hard and consistent effort, he accomplished more than many of his peers, elevated his family’s economic well-being, and gave his children access to opportunities he couldn’t even imagine. All without a college degree.

From him I learned the following:

• The improbable is possible if you consistently work hard.
• You can win the game of life even if you’re dealt a bad hand. Focus on playing the hand you’ve been dealt as best you can—don’t dwell on your hand being bad.
• Don’t let yourself be defined by your starting position in life. You’re in control of your destiny.
• You can’t do what everyone else is doing if your situation is different than theirs. Make decisions and act based on your situation, not what others are doing.

Happy Father’s Day, Pops! Thanks for being a great example and putting in the effort to win even though you had to travel twice as far as everyone else.

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

• Valuation methods – I’ve learned about another evaluation method. It’s interesting to listen to investors look at the same company and, using different valuation methods, arrive at different values. Sometimes great investments are in plain sight, but no one sees them. Investors just need to adjust the lens they’re looking through to see their true value.
• Wisdom – A friend shared a quote from Benjamin Graham. The publication of one of his books was delayed, but the book included better material because the delay allowed him to include “wisdom is acquired at the cost of much suffering.”
• Odds – I’ve been learning about how successful investors think about odds and risk. Sometimes you can reduce the risk materially by waiting until the odds of the investment having success tilt more in your favor.

Week one hundred sixty-eight was an enlightening week. Looking forward to next week!

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

• Contract details matter – This week was a reminder that details matter in contracts. It’s worth taking time to understand the details before agreeing to a contract.
• Schedule experiment – I’m a few weeks into my schedule experiment. The schedule change has had positive impacts that I didn’t anticipate. It’s led me to adjust what I read, when I read, how I read, and why I read. I’ll dive into the adjustments in another post; for now, I’ll just say that I’m happy with this new habit. I believe it will turbocharge my ability to acquire and compound wisdom. And I also believe it will increase the frequency with which I uncover insights.
• Back to growth – I’ve been talking with early-stage founders and tracking a few public technology companies. Anecdotally, there’s a trend of companies getting things cleaned up and returning to growth mode or discovering how to enter growth mode for the first time. Sentiment for some company leaders is shifting from negative to optimistic, which is a big shift from six months ago.

Week one hundred sixty-seven was an insightful week. Looking forward to next week!

Yesterday I was at a social gathering. The topic of markets and investing came up because a few of the people there make relatively small personal investments in their spare time. The gathering included people from various backgrounds, locations, and professions, so I was very curious to hear what everyone had to say. I observed three notable points:

1. Negative sentiment – These people are interested in investing only in traditional cash-flowing businesses. This wasn’t surprising; I’ve heard the same from other investors and entrepreneurs. What stood out was the negative sentiment my friends had about start‑ups, technology companies, and to a lesser degree public equities. Their views applied to all start-ups and technology companies (excluding mega caps such as Google).
2. Historical trends – They expect certain asset classes, including real estate, to continue to perform well even in the current interest-rate environment.
3. Debt – They’re still embracing the use of debt to purchase physical assets.

Here are my thoughts on each point:

1. Sentiment about start-ups and technology companies may have swung from too optimistic to too pessimistic.
2. Understanding why a trend occurred in the first place is important. Then you can assess whether the same conditions still exist and gauge the probability of the trend continuing.
3. Everyone must make the decision that’s appropriate for their personal situation when considering whether to assume debt.

I enjoy going to social events that include people from various backgrounds and perspectives. I get a lot out of conversations at these events. It’s a great opportunity for me to understand how different people think about things.

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

• May – May went by quickly. We’re now ~40% through 2023. In the first few months of the year, we’ve seen unexpected events like bank failures. I suspect that more surprises await as the year unfolds—hopefully positive ones.
• Successful investing – I listened to a successful investor share why he continues to invest after several decades. He’s doesn’t do it for the money—he’s wealthy. Rather, he likes the fact that to continue being successful he must continuously learn because the investing landscape evolves continuously. The mental stimulation and motivation to stay curious are enjoyable to him.

Week one hundred sixty-six was a productive week. Looking forward to next week!

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

• Investing opportunities – I had a great conversation with a good friend and fellow entrepreneur about investing. Convincing people to take the action you want them to take is critical to success in closing a deal. But building a strategic and thoughtful process to identify investment opportunities before other people do is key in investing. After studying successful investor entrepreneurs who’ve had outsize success, I know that the great ones realize this and built solid processes.
• Twin tailwinds – I shared a post about twin tailwinds. I’m thinking more about how to use the concept of twin tailwinds to understand market cycles and spot overlooked investing opportunities.
• Schedule – This was the fourth full week of my schedule experiment. The results are clear. Starting my day by reading long-form writings by experts on topics I want to learn more about has been a game changer. I’ve gained knowledge at an accelerated pace, and I’ve had new insights more frequently. This will become a daily habit. I still need to tweak goals and a few other things as I continue this habit.

Week one hundred sixty-five was a productive week. Looking forward to next week!

I’ve been sharing my thoughts daily for over three years now. I was recently asked how I’ve come up with a topic every day for 1,000+ consecutive days. It’s taken a bit of time, but I’ve developed a simple system. Here’s how it works:

• I keep in the back of my mind that I must write a post. So, I’m subconsciously on the lookout for insights and interesting information. If I read an article that catches my attention, I note it. If I’m thinking about something or have an insight, I note it.
• I capture a note in one of two ways. The first is email. I’ll send myself an email with the thought as the subject line. Sometimes I add links or additional thoughts in the body of the email. I tag these emails as blog content and archive them. The second is the Notes app on my iPhone and laptop. I have a single note with a running list of thoughts, insights, and links to other people’s writings that caught my attention. Lately I’ve been capturing more notes via email.
• At the end of each day, I review emails tagged as blog content and my Notes app. I choose the topic that resonates most with me. Then I think about it a bit more and start writing.

The most important and unexpected benefit I’ve gotten from this system is that it instilled in me the habit of capturing my thoughts. Recording my “lightbulb” and “shower” moments has been invaluable. Instead of losing these thoughts when the moment passes, I now keep them top of mind or at a minimum recall them later. This has enhanced my reflection process and ability to uncover insights I otherwise would have missed.

That’s my system. It’s simple and fairly low-tech.

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

• Schedule – This was the third full week of my schedule experiment. My purpose for reading something and the type of material affects how fast I read. For example, if I’m trying to understand a new, complex subject, I read more slowly (which I think is a good thing). Mornings are best for me for this kind of reading.
• Supply and demand – When supply far outpaces demand, people on the supply side will experience unwanted outcomes. In investing, this can occur when capital far exceeds quality destinations for capital. It’s better to be investing when the opposite is true.

Week one hundred sixty-four was a productive week. Looking forward to next week!

My early years were foundational for me. I had lots of energy and crazy ideas as a kid. My mom always listened to those crazy ideas and gave me the leeway to make mistakes. She encouraged me to work hard and, when things didn’t go well, reflect on it, dust myself off, and try again. Over the years I learned, became confident, and realized I love business and entrepreneurship. I’m super appreciative of her approach, her love, and most all, her patience with me!

Happy Mother’s Day, Mom! Thanks for being a great mom!