Earlier this month marked three consecutive years of sharing my thoughts publicly. I started posting on March 9, 2020 (my first post) because of a friend’s challenge. Here are my takeaways from my third year of posting:

• Reflection frequency –The more time between reflection periods, the less likely I am to uncover valuable insights because there’s more information. The more information to consider, the less likely I am to make connections between nonobvious pieces of information. Reflecting daily allows me to think more deeply about a shorter time period (less information) and identify nonobvious insights.
• Second-level thinking – Posting daily has enhanced my second-level thinking.
• Conviction – I have more conviction about my non-consensus views that have resulted from this process.
• Clarity of thought – Writing has helped me think more clearly on important topics. I’ve noticed this, and people close to me have commented on it too.
• Public thinking – Public writing leads to better outcomes than writing privately because it forces more clarity of thought.
• Second nature – The habit of posting daily is second nature to me now, which I enjoy.
• Quality – Every post isn’t going to be Pulitzer piece. That’s OK and normal given the daily frequency of this habit. Life is more eventful sometimes, and my posts reflect that.
• Appetite to learn – My appetite to learn has always been high, but it’s increased. I want to consume more information that I can reflect on and write about.
• Compounding knowledge – Consuming new information daily, reflecting on it daily, and writing about it daily is an effective process for building knowledge in a compounding manner.
• Topics – My writing has shifted from my experience as an e-commerce entrepreneur to my future as an investor entrepreneur.

I’m glad I picked up this habit and have stuck with it. It isn’t always easy, but after three years I can see that the positive far outweighs the negative. I want to keep this habit going and can’t wait to see what year four has in store!

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

• Geographic diversity – I’ve been thinking about my takeaways from a chat with a16z Partner Scott Kupor. I believe network distance is the biggest obstacle to achieving geographic diversity for VC investments, but many people may not understand this.
• Patience – I had a great chat with a friend who reminded me of the value of patience. Sometimes the best things take more time than expected to play out.

Week one hundred fifty-five was a busy week. Looking forward to next week!

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

• SVB – Silicon Valley Bank’s failure this week was a surprise. I’m curious to see how this failure will impact venture capital and banking more broadly. As of today, I know a few VC funds and start-ups with frozen accounts at the bank.
• New community – I joined a new community full of accomplished people this week. I’m excited to get to know them.  
• Young companies – Some of the largest companies in the US haven’t been around that long relative to their market cap (i.e., valuation). For example, Alphabet Inc. (Google) was started in 1998. Twenty-five years ago. It has a market cap of over $1 trillion. That’s a staggering rate of compounding and wealth creation.

Week one hundred fifty-four was a crazy week. Looking forward to next week!

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

• Biographies – There’s a lot to be learned from entrepreneurs who are no longer with us or at the tail end of their career. Wisdom learned over a lifetime is invaluable.
• Decision-making – I want to start developing and using more mental models to help make decision-making in complex situations easier.
• Rational thinking – Rational thinking is something I view as an advantage. I’ve observed that some people are rational thinkers in some areas of life but irrational in others. Thinking rationally in all areas of life is the key. It’s easier said than done.

Week one hundred fifty-three was a mediocre week. Looking forward to next week!

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

• Edge – Most people are good at something. They have a natural strength or skill. What you’re good at is your personal edge. If you play to your edge, you increase your chances of achieving outsize success. Play to your edge.

Week one hundred fifty-two was productive. Looking forward to next week!

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

• Context switching – A founder this week reminded me how hard it is to switch between thinking high level and being in the weeds of an early-stage company. I remember those days but haven’t lived them from a founder perspective in years. I found success using lunch as a natural mental break. It can be tempting to skip the high-level thinking when there are constant fire drills, but I learned the hard way that that’s a mistake. Consistently making time to think high level is something exceptional founders and people who achieve outsize outcomes do well.
• Gratitude – There’s always something that isn’t going right or could be better. Conversely, something’s always going right or could be worse. Continual improvement is important, but it isn’t my sole focus anymore. Practicing gratitude and being thankful have helped give me a more balanced perspective.
• Failed goal – Years ago, I set a goal. This week, I officially didn’t achieve it. Looking back, I realize why I didn’t. I should have spent more time sharing my goal. I should have spent more time learning about how others had accomplished similar goals. I should have focused on the habits required to achieve the goal. I learned a lot from this miss, so it wasn’t a failure. Just a painful learning experience. Today I set a new goal that’s bigger than the one I failed to accomplish.

Week one hundred fifty-one was a great week. Looking forward to next week!

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

• Truth tellers – Some people tell it like it is. They don’t sugarcoat things. They candidly share what they see and think about situations. People like this are valuable because they’ll say what others are often thinking but won’t say.
• Emerging markets – I had a great chat with two emerging venture capital fund managers investing in emerging markets—specifically, LATAM and Africa. I was intrigued and now want to learn more about early-stage entrepreneurship in these markets.
• Outsiders – There’s something to be said for people who’ve accomplished greatness after starting as outsiders. They tend to have fought their way into the position they’re in. They’ve traveled further than others. Their ability to learn faster than other people has usually been key to their outsize success.

Week one hundred fifty was a positive week. Looking forward to next week!

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

• Ideas aren’t original – Ideas aren’t usually new. Others have had your idea before, and someone may even have tried to execute on it. It’s always worth finding out whether that’s happened and, if so, what caused them to succeed or fail.
• Team – When you’re trying to do something difficult, you often can’t do it by yourself. You need others, but finding people who are the right fit isn’t easy. This week was a reminder of that.    

Week one hundred forty-nine was a good week. Looking forward to next week!

I’m a fan of continual improvement, and I’m always looking for techniques to make it happen. I enjoy reading about ways for individuals and teams (e.g., a company) to optimize performance. Lately, I’ve been reading about individual optimization—sleep, diet, exercise, and cognitive performance. I made some notes:

• Things that move the needle the most on personal optimization aren’t the most appealing options (sometimes you dread them). And doing them can be an unpleasant experience. But when you finish and are on the other side of your decision, you feel great and happy you did whatever it was. Examples include big things like a grueling physical workout. But they also include little things like cutting a TV show short to go to bed early.
• The things that slow or even prevent personal optimization are often attractive options that feel great in the moment. But you don’t feel great, or you have regret, when you’re on the other side of the decision. I’m thinking of things like excessive alcohol consumption (i.e., a hangover), an unhealthy meal, or even staying up late to watch a movie. All of them feel good in the moment, but later that day or the next day when they negatively affect your performance—not so much.

Sometimes I focus on the desirability of an activity—how I’ll feel as I do it. If I dread it, think it will be unpleasant, or just don’t want to do it, sometimes I opt out. That’s the wrong approach. Given my desire to optimize my performance, I want to change the criteria I use to make these decisions. I want to focus on how the activity will make me feel afterward. Said differently, I’ll ask myself “Will this make me feel better or improve me?” If the answer is yes, I should do it. If the answer is no, I should say no (though there will always be exceptions).

Asking myself this question is a simple mental hack to make better decisions that optimize my performance.

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

• Missing piece – I spent time this week with a rising entrepreneur. He shared what’s holding back his business, and it’s something I’ve heard from other entrepreneurs. He's able to find attractive deals but doesn't know how to structure deals to attract investor capital. I think there’s an opportunity to provide it to him and other founders to help unlock more value.
• Sentiment – I chatted with investors and entrepreneurs in various sectors (not just tech) this month. There’s a noticeable, albeit slight, uptick in investor and entrepreneur sentiment this month. Tuesday marks the end of the month. I’m curious to see if this slightly positive sentiment continues in February.  
• I still get things wrong – I made a decision that didn’t pan out the way I planned. It was a mistake. This week was a reminder of a couple of things: (1) I still make mistakes regularly, and (2) I should spend time reflecting on what I learned from a mistake, not dwelling on the fact that I made one.  
  

Week one hundred forty-eight was a great week. Looking forward to next week!