I’ve been posting daily since 2020. After three years, it’s still something I enjoy and get a lot out of. When I first started, lots of low-hanging fruit was available—I had many experiences as a founder that I could reflect on and identify insights from. I wasn’t used to sharing my thoughts publicly, though, so it took energy to crystallize my thoughts and craft a post that people could understand.

Now that I’ve been doing this for a few years, I can write a post with minimal effort. I’ve built muscle memory around writing and gaining clarity of thought.

I focus my effort now on identifying interesting things and insights to share. I’ve become more intentional about acquiring knowledge related to concepts I want to understand and attempting to develop unique insights about them.

The result of all this is that writing daily posts is still challenging, but in a different way. I began by being more intentional about developing the habit of sharing my crystallized thoughts. I’m now more intentional about understanding a concept and identifying insights related to it. Focusing on concepts is more difficult. I’ve had to adjust my habits to support the change, but I’m happy with the adjustments. I’m excited to be learning about interesting and difficult concepts. I’m even more excited by the challenge of coming up with unique insights.

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

• Decision feedback – I’m curious to try out the new technique for improving decision-making that I wrote about recently. I’m going to start asking a few people I think highly of if they’ll provide feedback.
• Jump start – Sometimes it’s good to have a change of scenery for thinking. For some reason it jump-starts my creativity and my ability to recognize insights.
• Frustration – Earlier this week, I was frustrated about a few things that were out of my control. Exercising and talking through my frustrations with others was helpful.

Week one hundred seventy-two was a frustrating week. Looking forward to next week!

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

• Adjust solutions, not people – Trying to bend customers so they can use what you’ve built doesn’t end well. The best solutions are built and scaled when you’ve listened to what customers want and adjusted the solution to meet their needs and solve their pain point. Adjust the solution to people, not people to the solution.
• Holiday – It was great to spend time with family and friends. I was able to get some good reading in, too.  

Week one hundred seventy-one was a short week. Looking forward to next week!

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

• Entrepreneurial swings – I caught up with an entrepreneur friend. Two years ago, things didn’t look good, and he wasn’t sure his company would survive. Today it’s thriving and kicking off more cash than he knows what to do with. Things can swing from one pole to another fairly quickly for entrepreneurs. The key is to persevere.
• Q2 – The quarter is officially over. It went by quickly. Hard to believe we’re halfway through the year. Looking forward to the second half of 2023.
• Workflow management – I’m optimistic about workflow management technology. Companies can’t just throw people at problems anymore and will actively be seeking software solutions. Many companies’ focus on efficiency is blowing up a strong tailwind for start-ups solving painful workflow management problems. These are B2B companies solving unsexy problems, which is a combination that can create a great foundation for a business.
• July 4th – Next Tuesday is a holiday. Looking forward to spending time with family and friends and reading a few new books.

Week one hundred seventy was a steady week. Looking forward to next week!

When I started posting daily in 2020, I had a decade-plus of entrepreneurial experience from building a company. I thought about those experiences and identified insights about entrepreneurship. Then I shared my insights in a way that people could understand (and hopefully find useful).

Lately, I haven’t been getting as much from the process of creating my posts. I thought about why I feel this way and concluded that I haven’t been as consistent in sharing insights in my posts. More of my posts have contained information but not shared deep understandings. I realized that the process of gaining an understanding of a topic and then distilling and sharing it concisely is fulfilling. It isn’t always easy to come up with insights and communicate them, but I’ve enjoyed it when I have.

I want to get back to writing more insightful posts. To do so, I’ll need to accelerate the rate at which I acquire knowledge on certain topics and come to understand them.

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.