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

• Fundraising – I chatted this week with two founders who are finalizing fundraising rounds. They’re wrapping up diligence and have target close dates in the next week or so. I suspect most investors and lawyers are aiming to get most deals done by December 15.
• Serendipity – I ran into someone I haven’t talked to in years. We caught up, and I learned that he has expertise that will be helpful with something I’m actively working on. He even offered to help. I’ve benefited from serendipity many times, but I’m still surprised by its power.

Week one hundred ninety-three was another week of learning. Looking forward to next week!

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

• Home stretch – It’s December. We’re in the last leg of the year. I want to make these last few weeks count. My intention is to focus on only the highest-priority things for the rest of the year. 
• Daily habit – I’ve been intentional this year about learning something new every day. This week I noticed that I felt unsettled one day when I hadn’t learned anything new. It was a welcome feeling because it meant this habit had been formed and my mind was expecting something new. Before the day was over, I cracked open a book on a topic I’m interested in.

Week one hundred ninety-two was another week of learning. Looking forward to next week!

In 2022, I realized the power of a foundational habit. Identifying and committing to a daily foundational habit greatly increased the probability of my sticking with other daily habits. When I consistently complete all the things that I decided need to be daily habits, my chances of reaching a desired destination or objective increase drastically. I like focusing on habits and systems over results and goals.

With the new year approaching, I want to start working on my 2024 habits. Before the new year begins, I want to crystallize where I’d like to be by the end of 2024, identify the new habits that align with that destination, and identify the foundational habit that I need to focus on.

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

• Thanksgiving – It was great to have time off yesterday to spend time with family and friends and eat amazing food.
• Reading – I’m using my downtime during this holiday to hit my reading goal.
• VC firm origin stories – Company origin stories are always interesting. This week I stumbled upon a podcast on which the origin story of a successful VC firm was shared by one of the firm’s founders. It was great and got me thinking about a few ideas. I’m going to look for more origin stories of unorthodox investment firms.   

Week one hundred ninety-one was another week of learning. Looking forward to next week!

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

• Brainstorming – This week I spent time brainstorming with a fellow investor. We ended up landing on an interesting idea we’re both excited about digging into more. Neither of us entered the conversation with the idea. This was a reminder of the power of brainstorming with high-caliber people. I need to do it more regularly.  
• Public markets – I’ve been spending more time looking at companies in the public markets. This exercise has me thinking about early-stage investing a bit differently.
• Randomness – The world is full of randomness. Things that have a low probability of happening nevertheless happen sometimes when you least expect them. This week was a reminder of how randomness sometimes produces unexpected surprises or unexpected disappointment (or even pain).
• Fundraising – Next week is Thanksgiving. If founders haven’t received a term sheet by next week, their likelihood of completing a fundraise before year end will have decreased materially.

Week one hundred ninety was another week of learning. Looking forward to next week!

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.

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

• Suitable investments – Some generally accepted opinions about what constitutes a quality investment opportunity are illogical. They create pricing inefficiencies around supposedly unsuitable investments. Therefore, this type of investment can be acquired for less than fair value, which can lead to outsize returns. Investors who think outside the box and question the status quo are more likely to realize the outsize returns made possible by these unconventional opportunities.
• Constraints – Constraints, real or artificial, are helpful in spurring creativity and focus and business and personal pursuits. I want to experiment with adding more constraints to certain areas of my personal life. I’m curious to see what the results will be.

Week one hundred eighty-nine was another week of learning. Looking forward to next week!

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

• Learning – A superpower that people who achieve outsize success possess is learning outside a structured environment (e.g., school). They’ve testing different ways of learning and found one that suits their personality. They’ve refined their approach and continuously used it to learn new things. Their self-starter approach to learning improves their problem solving and allows them to create value for others.
• Fundraising – Founders are in the final stretch of fundraising before the holiday season begins. Any deals that will close before year-end will likely be agreed upon in the next two or three weeks. Fundraising activity doesn’t usually pick back up until February.

Week one hundred eighty-eight was another week of learning. Looking forward to next week!

Today I read Fred Wilson’s post about sleep. Wilson is a well-known VC and general partner at Union Square Ventures, which he cofounded in 2003. In his post, Wilson talks about his struggles with sleep over the years and what changes he’s made to improve it. The big takeaway is that poor sleepers can improve their sleep, and even become good sleepers, by changing their habits.

I’ve spent time researching ways to improve my sleep. I don’t have an Oura Ring like Wilson, but I’ve done a few things that have significantly improved my sleep quality:

• Eight Sleep bed – This bed has had the biggest impact on my sleep quality. I was an early adopter and have had one of these for a few years. The bed regulates the temperature, which helps me get into and stay in a deep sleep.
• Television – I don’t have a TV in the bedroom. My body knows that when I’m in my bed, it’s time to start transitioning to sleep mode.
• Bedtime – I try to stick with a consistent bedtime on weekdays. This keeps my body on a schedule.
• Reading – I like to read in bed to wind down. I try not to read anything that requires deep concentration and usually save biographies and histories for bedtime.  
• Blackout curtains – I’ve found that a dark room helps me go to sleep and stay asleep.

Sleep quality is something I’m curious about. Good sleep’s ROI is massive. Therefore, I enjoy learning about the subject and tinkering with ways to improve the quality of my sleep. I suspect that high-quality sleep will be a lifelong quest as my body continues to evolve.

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

• VC – There’s an interesting dynamic now in seed-stage venture capital. Fund managers are out fundraising for new funds—but it’s tough because limited partners (LPs) are, in general, less receptive to the venture capital asset class. Some of these managers have some companies in their portfolios that are running out of runway and having a hard time raising capital. These companies could shutter. It’s already hard to raise a new fund right now. If some of a fund manager’s investments go to zero during their fundraise process, that won’t exactly give LPs a warm and fuzzy feeling about giving them more money to invest.   
• Value-add investors – Things are tough for some founders right now. They’re likely finding out which of the investors on their cap table are truly value-add investors.

Week one hundred eighty-seven was another week of learning. Looking forward to next week!