I used to journal first thing in the morning. I gained a lot from the process and thoroughly enjoyed it. But my routine has since changed—the first thing I do in the morning now is read a book. I’ve been thinking about how to incorporate some form of journaling into my day, and this week I started testing something new: voice recordings.

When I take my daily walk, I’ve started recording what I’m thinking about and what lessons, if any, I learned that day. I didn’t have any expectations when I started doing this, but I’ve been surprised by how much I enjoy the process—specifically, being able to listen to my lessons as I walk. It’s also a daily feedback loop that allows me to listen to and critique how I communicate my thoughts.

It's low tech, which I like: just a phone, Voice Memos app, and EarPods. The one thing I do miss is being able to read my thoughts in a written journal format. I’m sure I can turn these recordings into clean docs with AI. I’ve chatted with a buddy who’s done this, and he gave me some useful tips and ideas on how to write the prompt to achieve this.

Looking forward to using AI to help with this. If it all works as I envision, I may have created my new digital journal.

I’m working with a founder on his pitch deck, and his market-size slide was one we agreed needed work. Lots of founders use a top-down approach to sizing their market. For example, they estimate the market to be $10 billion and assume they’ll capture, say, 20% of it, resulting in a total market share of $2 billion. Coming up with this is easy, but it’s not the best approach. It doesn’t add much value to the entrepreneur who did the exercise, and investors won’t put much weight on it either.

The better approach is one that’s bottom-up. I’ve written about this before (see here), and I won’t rehash everything in that post. But for entrepreneurs looking for an example of how to do a bottom-up sizing of their market, I like this blog post from Bling Capital. It’s detailed and includes a link to a market-sizing template that’s very helpful. (Note: Its site has been updated, so I’m linking to the post on Internet Archive.)

In 2024, I challenged myself to accelerate my learning by reading a book (usually a biography) a week. To date, I’ve done it for 72 consecutive weeks. I wanted to share what I was reading and also keep track for myself, which was difficult (see here), so I created a Library section on this site. I added to it all the books I’ve read since my book-a-week habit began in March 2024, and I’ve committed to adding my latest read to the Library every Sunday (see the latest here).

That left the books I’d read before 2024 unshared and untracked. I set a goal to add my old reading to the Library over time. It began with a Memorial Day Challenge to add five books (see here) and continued with my challenging myself to add two books every weekend until my backlog is gone. This past weekend was my eighth weekend, and I added two more books:

• Thinking in Bets by Annie Duke
• The Price of Tomorrow by Jeff Booth

That’s the latest update on my weekend goal. I hope that sharing these books will add value to others.

In addition to entrepreneurship, I love investing. It’s an intellectual sport that you can never master and that requires continual learning. A few weeks ago, I listened to a podcast with investor and Columbia Business School professor Michael Mauboussin in which he described the concept of expectations investing. The gist is that it’s a method of figuring out what’s already factored into a stock’s current price. He mentioned his book, which details the method, so I bought a copy.

I read the updated and revised version of Expectations Investing, which describes an interesting framework for deconstructing a stock price. The main principle in this framework that makes it different from other valuation methods is that you don’t forecast cash flows to determine the worth of a company and its stock price. Instead, you estimate expectations that are factored into the current stock price to determine what the market anticipates cash flows will be and how many years into the future the market is forecasting those cash flows (i.e., the forecast period). It’s akin to starting at the end and working backward, which intrigued me. Once you know what the market is expecting, you can determine if those expectations are reasonable or will likely lead to revisions (i.e., changes in the stock price).

The framework is great, but it’s not for beginners. I think of it as a graduate-level approach to value investing. It’s not easy to execute initially, but with work and practice, it can be learned by anyone. The book’s website offers useful tutorials that supplement learning.

Other things I like about this book are the “expectations infrastructure” frameworks around thinking about company value creation (value triggers, value factors, and value drivers). The three methods for estimating the continuing value of a company in a discounted cash flow model that incorporates inflation expectations were very useful. And I found his step-by-step approach to determining a company’s cost of capital useful.

I’m glad I read this book. It led to my doing some modeling and analysis of companies using this method, which was both frustrating and fun. If you’re interested in learning about advanced value investing and understanding what’s priced into a stock already, consider reading Expectations Investing.

Current Project: Reading books about entrepreneurs and sharing what I learned from them

Mission: Create a library of wisdom from notable entrepreneurs that current entrepreneurs can leverage to increase their chances of success

Cumulative metrics (since 4/1/24):

• Total books read: 72
• Total blog posts published: 469

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed this week (link to last week’s commitments):

• Read Expectations Investing, an advanced value-investing framework by Michael Mauboussin and Alfred Rappaport
• Added two more books that I read in 2023, these from Gautam Baid and Bill Carr and Colin Bryar, to the library on this site—see more here

What I’ll do next week:

• Read a biography, autobiography, or framework book
• Add two more books that I read before 2024 to the library on this site—see more here
• Create a digest of one biography, autobiography, or framework book

Asks:

• Seeking technical lead or cofounder – I’m looking for a senior full-stack developer skilled in AI retrieval. If you know one who’d have an interest in working on the software project related to books, please introduce us!

Week two hundred seventy-seven was another week of learning. Looking forward to next week!

Current Project: Reading books about entrepreneurs and sharing what I learned from them

Mission: Create a library of wisdom from notable entrepreneurs that current entrepreneurs can leverage to increase their chances of success

What I struggled with:

• A lot was going on this week, so I didn’t read as much each day as I should have.

What I learned:

• No material learnings this week.

That’s what I learned and struggled with last week.

I set a goal to read a book a week, and I’ve hit that target for 71 consecutive weeks since March 2024. But this week, there’s a decent chance that I won’t. It’s been a busy week. I’ve read every day, but fewer pages each day. I’ve spent some of my morning time designated for reading instead thinking about another project.

The streak of 71 weeks is something I’m proud of, and it motivates me. I don’t want to break it. I’ve told myself I’m going to do everything I can this weekend to keep it going. I’ll wake up extra early and cut out some other stuff I had planned so I’ll have more reading time.

Hopefully, this will do the trick and I’ll finish the book. Wish me luck!

Every once in a while, I have a crazy day that makes it hard to focus and think clearly. When this happens, the rest of my day is unproductive. It feels like I wasted a day.

This week, something hit my radar in the morning that threw me off mentally. I tried, but I couldn’t get back in the zone to finish working. I needed to think clearly because I had important decisions to make later that day, so I tried something different. I went to the gym. I do this regularly, but not in the middle of a work morning. But I figured I had nothing to lose since I couldn’t focus. I did a heavy-weight workout for about an hour, ate a snack, and then returned to my computer.

When I began working, my head was clear. I was extremely productive. The rest of the day was smooth, and I felt great about the decisions I made that afternoon.

I can’t explain why the workout helped so much (I plan to research the science behind this), but it felt like a 180 that put me back where I needed to be mentally.

I haven’t tried this before, and I’m glad I gave it a shot this week. It’s a new hack in my toolbox. If something throws me off to the point where I can’t focus, I’ll close my computer, go to the gym, and hit the weights.

This week, I had the opportunity to catch up with an entrepreneur who has an idea-stage company. He and his cofounders have built an MVP and are now looking to raise money from investors and acquire customers. When a seasoned entrepreneur and I chatted with him, both of us zeroed in on a material issue: he couldn’t quickly and concisely articulate the problem his product solves.

We brought this to his attention, and he agreed that he and his other cofounders need to get specific about the problem. When I talked to him a few days later, they’d spent significant time debating the point. He presented the new problem statement to me. It was better, but still not clear. They’re back working on it again.

A business exists to solve a problem for customers. If the solution is good, it creates value for customers by resolving their problem and the customers pay the business for the value it created. It’s that simple.

If a business isn’t clear on what problem it’s solving, customers won’t be clear on how the business can help them. They’re less likely to buy.

My point is that clarifying the problem is a crucial step. The problem is the entire reason the business exists. It’s the foundation of the business. Without clarity about the problem, the business is built on a weak foundation and everything about building the company becomes significantly harder (it was never going to be easy).

If you can’t articulate the problem you’re solving in a way anyone can understand—in one sentence—ask yourself, What problem am I really solving?

In 2024, I challenged myself to accelerate my learning by reading a book (usually a biography) a week. To date, I’ve done it for 71 consecutive weeks. I wanted to share what I was reading and also keep track for myself, which was difficult (see here), so I created a Library section on this site. I added to it all the books I’ve read since my book-a-week habit began in March 2024, and I’ve committed to adding my latest read to the Library every Sunday (see the latest here).

That left the books I’d read before 2024 unshared and untracked. I set a goal to add my old reading to the Library over time. It began with a Memorial Day Challenge to add five books (see here) and continued with my challenging myself to add two books every weekend until my backlog is gone. This past weekend was my seventh weekend, and I added two more books:

• The Joys of Compounding by Gautam Baid
• Working Backwards by Bill Carr and Colin Bryar

That’s the latest update on my weekend goal. I hope that sharing these books will add value to others.