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

• Schedule – I’m excited about my new schedule. Can’t wait for next week—the first full week. I’m curious to see what impact this change will have.
• Consensus – I had a few conversations with entrepreneur friends who have a passion for investing (public and private). I noticed they’re adopting the same viewpoint and risk tolerances at the same time. They all have the same reasoning (which I must admit is grounded in logic). I didn’t hear any contrarian views, which was surprising for this group. No one is considering a new or better approach.
• Patience – Sometimes people take a different path to get to the same conclusion or insight as you. You might not agree with their path or like their pace. This week reminded me to be patient and to remember that what’s important is that you both ended up at the same place.

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

I’ve developed a habit of starting my day with physical activity. Walking, weights, etc. Getting my blood flowing and working up a nice sweat. It’s been a great way to get the day going, and it gives me energy throughout the day.

I’m a morning person. My brain is firing on all cylinders when I first wake up. I have my best ideas and clearest thoughts early in the morning when it’s quiet. Knowing this, I didn’t always feel like I was getting the most out of my most productive time, since I was exercising instead of thinking.

I want to be intentional about reading more long-form pieces as part of my daily learning habit. I usually do this in the evening. Sometimes I’m tired, which affects how much I absorb. And I tend to put off reading anything that requires deep thinking.

This week I decided to tinker with my schedule a bit. My goal is to figure out what the right activity is for my most productive early-morning hours.

I’m going to experiment with starting my day reading long-form writings. I plan to focus on things experts have written about topics I want to learn more about and on dense business materials (e.g., white papers and reports). The idea is to be able to think more and absorb more of what I’m reading because my brain will be fresh. I’ll keep reading in the evening too, but I’ll focus then on stories and autobiographies where I just need to follow along. As for my workouts, I’m aiming to do those at lunchtime.

I’m curious to see how this experiment works and what I learn from it.

I was asked about my plans for retirement recently. Here’s how Merriam-Webster defines “retired”:

Withdrawn from one’s position or occupation : having concluded one’s working or professional career.

A few years ago, I had the opportunity to take a few months off after rarely taking time off for the last decade. I gave myself permission to disconnect. I wasn’t thinking about anything that resembled work. I wasn’t thinking about how to solve problems; I wasn’t tinkering with new ideas. I wasn’t checking email (regularly). I wasn’t talking business with anyone. I focused on doing things I couldn’t do while I was leading a company, like spending a few weeks with a family member who was recovering from a life-threatening medical condition. I completely withdrew from work.

I enjoyed the time off and being able to reconnect with people. It was a much-needed respite after years of grinding. But I also felt like I was at a standstill. As a founder, I was constantly having to rise to the occasion to overcome the latest hurdle. That kept me in perpetual learning and growth mode. I didn’t always enjoy the things I had to work on or learn as a founder, but I enjoyed the personal growth. My time off felt odd because I wasn’t being challenged or growing—not quickly at least. Mental stimulation was missing.

I did learn from the experience how powerful controlling your own time can be. Other people have affected my calendar since I was a child. If it wasn’t a school schedule, it was a work schedule or a business issue or something or someone else materially impacting how I spent my time. But during my time off, my calendar was under my sole control. I wasn’t working on stuff I didn’t want to work on. I wasn’t spending time with people I didn’t want to spend time with. I was in complete control of my time. It was quite liberating.

At the end of my down period, I concluded that my goal isn’t to retire. I’ll never want to retire (in the traditional sense). I’ll never want to walk away from the professional things I enjoy and the mental stimulation they bring. Instead, I want the freedom to work on the things I enjoy and that are mentally stimulating.

My goal isn’t to retire—it’s to control my time in perpetuity. I want the freedom to work on things and with people that bring me joy (so it doesn’t feel like work). If it doesn’t feel like work, I’ll end up doing more of it. I’ll be as engaged and busy as ever!

My retirement plan is to never retire.

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

• Runway – A few early-stage founders I know are running out of runway. Founders who can’t raise more capital will have to start making tough decisions. You can’t kick the can down the road when you’re out of cash.
• Venture – I chatted this week with a few high-net-worth people who made their wealth building tech companies and invested in venture capital funds. They’re more interested now in investing in traditional companies that generate cash, not venture-backed companies or venture funds.
• Founder hunger – A founder friend told me about what he’s doing now. Even though he doesn’t have to do anything (he’s financially set), he’s a founder at heart and still has a hunger and drive to try and build new things.

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

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

• Financial leverage – I spent part of this week thinking about leverage in the financial system. Leverage is common in business, but when it becomes excessive it can cause problems. I believe there’s a high probability that there’s a material amount of leverage in the financial system that we’re unaware of. It’s hidden for now. When it’s exposed, it may cause problems.
• Being present – I carved out time this week to celebrate with family, shutting down everything else to make sure I was present. I’m glad I did.

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

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

• Knowledge – Knowledge is power. If you understand complex dynamics, you can make informed decisions and take appropriate action. But obtaining knowledge isn’t easy. You shouldn’t expect people who have it to give it to you freely. It took them lots of time and energy to acquire it or to arrive at the insights that preceded it. If you want to acquire knowledge, be ready to put in time and effort.
• The frequency of little things – I just started reading a new book about relationships. The most important thing the author says is that the frequency of little things matters a lot—it sets the tone in a relationship.
• History – I’ve been digging into financial markets’ past to better understand the present. History may not repeat itself, but it appears to be rhyming.

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

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

• 1st Quarter – Q1 2023 is officially in the record books. Full of unexpected developments, it’s a quarter to remember. I’m wondering if 2023 will be the years of twists and turns.
• Zoom out – This week was a reminder that sometimes it’s helpful to zoom out and look at things over a longer period. Doing so gives context to where you are today.
• The past won’t predict the future – Many people are assuming we’ll get to a norm that looks like the past few years. That belief ignores the fact that today is materially different from the past in many ways, which decreases the chances of the future looking anything like the past. A new norm is more likely, in my opinion.

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

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

• 1,100+ daily posts – I’ve been posting daily for three years. I never would’ve imagined I’d keep up with this habit for this long, but I’m glad I have. Writing thoughts down is a powerful habit that’s had a big impact on me.
• Messaging – Working on messaging for a project. Messaging isn’t easy, but it’s important: it can have a material impact on perception and comprehension.
• Communities – This week was a reminder of the power of community. Bringing people together who otherwise might never connect is powerful and allows for serendipity.  

Week one hundred fifty-six was an exhausting week. Looking forward to next week!

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!