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!

Six months ago, I began experimenting with a new schedule. I wanted to be more intentional about how I use the time when my brain is most productive (mornings). Specifically, I wanted to read long-form writings (books, papers, etc.) when I first wake up instead of exercising. (I still exercise, but usually at lunch or in the afternoons.)

This change has had a much bigger positive impact than I anticipated. A few takeaways:

• Optimized learning – My brain absorbs new, and sometimes complex, concepts better in the morning when it’s fresh. After reading something new, I think about it throughout the day and sometimes have a new insight. I don’t do mindless or busywork activities when my brain is fresh.
• Relearning how to read – I took time to study the most effective way to read. I’m now more intentional about focusing on a single concept I want to learn about and seeking out books by those who have mastered the concept (or have a superior understanding of it). I read these materials with the intent to understand the critical part of their argument, not the supporting details. This has accelerated the pace at which I read and understand a concept. After I understand one concept, I move to the next concept and repeat the process.  
• Pace – I finish books much faster, which means I’m learning much faster. 
• Habit – Reading first thing in the morning has established a habit that is second nature now. My brain expects to learn something new every morning.
• Book list – I've found that as I’ve accelerated the rate at which I consume books, I've also accelerated the rate at which I add new books to my reading list.
• Challenge – I initially set a daily goal for my reading that pushed me. I now regularly hit that goal and will expand that goal to push myself a little harder.  
• Night reading – I still read in the evenings too, but I tend to read historical books, such as biographies. For me, nighttime reading is not optimal for learning new concepts.

This experiment has instilled a new habit into my life that I think will have a big impact in the long run. I’m still tweaking things a bit but should have my approach fine-tuned and daily goals solidified by the beginning of the new year.

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

• No – This week was a reminder that the power of saying no more than yes is underestimated. Saying no allows for more focus on the things that matter most and maintains the optionality of new opportunities. Saying yes to too many things can result in lack of focus and loss of future optionality.
• Strategic sales – I’m hearing more early-stage founders with diminishing runway discuss the possibility of selling their business to a strategic acquirer if they can’t raise additional capital.

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

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

• Simple business – I talked with friends about a simple business that’s performing exceptionally well. We were all surprised at how well. This was a reminder that great businesses don’t need to be overly complex. Sometimes the model can be simple and superbly executed.
• Early-stage VC – I’ve had some great conversations with early-stage VC investors the last few weeks. The consensus seems to be that early-stage entry prices are still high relative to public markets.

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

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

• Seeing the obvious – Sometimes I look at something many times. Then one day it clicks, and I see something I’d missed. Afterward, it seems so obvious that I wonder how I ever missed it. This week was a reminder that the obvious isn’t always obvious at first.
• Conviction – Having conviction in what you’re doing matters, especially when you’re doing things that are non-consensus. Doing the work to build that conviction is important.   
• Fundraising – Raising too much money too early can negatively impact a start-up. Some founders think the more money they have, the better, without thinking through the implications. I had this chat with a few founders this week.
• Investing edge – All investors need an edge to generate outsize returns. You can copy what another investor does but not generate the same returns because you don’t have the same edge. Finding the edge that’s unique to you is important—but not easy.  
• Reinventing the wheel – I want to lean more into getting exposed to great ideas and building on them instead of trying to create so many new ideas.

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

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

• Atlanta conferences – Venture Atlanta and A3C are going on this week. Both events brought people to Atlanta to attend. It was great to catch up with people and get a finger on the pulse of what’s happening in other geographies from people on the front lines.
• Teaching – This week, I explained an investing concept to a college friend. He was able to grasp it in a quick phone call, and he said it was beneficial—it helped him think about things differently. It felt good to help someone understand a complex concept quickly. This was a reminder that truly understanding something means being able to teach it to others.‍
• More entrepreneurs – Last week, I wrote about conversations I had with people considering becoming solopreneurs. This week, I spoke with two highly accomplished people considering leaving great organizations to pursue entrepreneurship. They don’t want to be solopreneurs, but this is another anecdotal data point about people leaving stability to pursue entrepreneurship so they can control their own destiny.‍
• Fundraising season – This week was a reminder that fundraising activity is high right now. I chatted with founders and fund managers about their fundraises. Some are going well; others aren’t. I think it’s good to have regular conversations with someone you trust who’s unaffiliated with your company or fund. Sometimes they can help highlight things that down-in-the-weeds founders and fund managers miss.‍
• Q3 is complete – Today was the last business day of the quarter. We’re two-thirds through 2023. Before you know it, the year will be over. I’m optimistic about what’s in store for Q4. I’m also starting to think about 2024.

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