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: 85
• Total blog posts published: 560

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed in the week ending 10/19/25 (link to the previous week’s commitments):

• Read Think Twice, a framework to improve decision-making in complex and uncertain environments by Michael J. Mauboussin
• Added two more books to the library on this site; these, which I read in 2017 and 2016, were about Michael Lewis’s time as a Salomon Brothers bond trader in the 1980s and 12 business case studies on how human behavior in stressful times shapes decision and outcomes

What I’ll do next week:

• Read a biography, autobiography, or framework book
• Pick my next weekend project and start working on it

Asks:

• No ask this week

Week two hundred ninety 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:

• No material struggles last week

What I learned:

• I learned about Kidlin’s law last week. It states that if you write a problem down clearly, then the matter is half solved. This really stuck with me, and I’ve been thinking about it all week. I’ll share my thoughts on this in the upcoming days.

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

I’m excited about this weekend. I’m on pace to finish adding all the books I’ve read to my library. I’ve been working on this weekend project for about six months. It’s been fulfilling, but I’m ready to finish it and move on to the next thing.

More importantly, this weekend I’ll need to choose what my next weekend project will be. I’m considering a few ideas. The one constraint I’ve been thinking about is that it should be something I can finish in one to four months. One month would mean a commitment over multiple weeks that requires consistent effort. And at most, it won’t require more than 16 or so weeks of consistent effort. Surprisingly, that constraint is making it harder to pick the next project.

Regardless, this will be a good weekend. I’ll get to celebrate finishing something I began half a year ago and start something new I’m excited about working on for at least a month.

This past week, I reread Expectations Investing by Michael Mauboussin and Alfred Rappaport. The book is an advanced value-investing framework that investors can apply to public companies to understand price relative to expected value. I read the book this summer. The framework made sense at a high level, but it had many moving parts that left me less confident that I could actually apply it and understand the expectations implied in a public company’s stock price. I wanted to try using the framework right after reading the book, but I never got around to it.

So, I reread the book this month, focusing heavily on my highlights and notes from the first reading. I then spent time building a model for a public company I follow. After several days of part-time effort, I finally finished it. After finishing the model and reviewing the output, I have a new appreciation for this book and the expectations-investing framework. It’s definitely something I’ll use going forward.

One of my big takeaways was that although the framework seemed daunting at first, after working through it (and getting stuck several times), I better understood its component parts. Lots of intertwining formulas. Required data from external sources. And several other moving parts. More importantly, I was able to simplify some of the more complex calculations, such as the Perpetuity with Inflation method for estimating continuing value. Said differently, going through the steps of building a model and applying the framework helped me understand it deeply and figure out ways to simplify it.

I’m glad I reread this book and applied the framework. It deepened my learning and took my understanding of this framework to the next level.

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 84 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 by challenging myself to add two books every weekend until my backlog is gone. Last month (see here), I decided to up the pace so I can finish this project well before the holidays—and begin another one!

This past weekend was my nineteenth weekend, and I added five more books:

• The Buy Side by Turney Duff
• Black Edge by Sheelah Kolhatkar
• Barbarians at the Gate by Bryan Burrough and John Helyar
• The Luck Factor by Dr. Richard Wiseman
• Chaos Monkeys by Antonio Garcia Martinez

That’s the latest update on my weekend goal. I hope that sharing these books will be of value.

This week, I caught up with a founder who’s out of runway. He raised several million dollars from VCs to fund the company for four years. After several pivots, they found a product that customers love and are paying for. But they don’t have enough cash left to accelerate the search for enough customers to reach cash-flow breakeven. Investors aren’t willing to invest additional funds.

He shared with me his biggest learning from his four-year experience:

Bootstrap as long as possible before raising venture capital. Being low on funds forces you to be laser focused on problems customers are willing to pay to solve. After you build a solution and customers are paying for it, raise capital to scale it. Raising a ton of cash too early increases the risk of building nice-to-have solutions rather than solutions to truly painful problems. A nice-to-have is like a faulty foundation under your house. You’re constantly trying to fix it, but that’s hard to do because of all the stuff on top of it.

Every founder’s situation is different, but I do agree that too many resources too early can lead to a lack of focus. When resources constrain you, you’re forced to focus only on what truly matters and what customers will actually pay for. Focus fixes everything, and constraints force you to focus.

Venture capital firms have a dilemma: there’s no exit for their founders. I read about Georges Doriot’s VC firm, American Research and Development Corporation, being publicly traded (see here). But being a public company ended up causing issues, and Doriot merged the firm with a conglomerate in 1972. Since then, VC firms have been private, and there hasn’t been a market for buying or selling them.

Today, that changed. I read this article, which says that Goldman Sachs is buying Industry Ventures (IV) for a reported $665 million plus an additional $300 million based on performance. IV has about $7 billion in assets under management. This is interesting because VC firms weren’t considered assets that could be sold. Their founders’ wealth came from carry (profit-sharing) and management fees.

I’m curious to learn about the details of this transaction and see how the market reacts to it. If VC firms become assets that can be bought and sold, I imagine we’ll see a shift in the strategies and actions of founding partners of VC firms.

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: 84
• Total blog posts published: 553

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed in the week ending 10/12/25 (link to the previous week’s commitments):

• Reread Expectations Investing, an advanced value-investing framework by Michael Mauboussin and Alfred Rappaport, because I want to use this framework to build a model to evaluate a public company
• Added five more books to the library on this site; these, which I read in 2017, were about Raj Rajaratnam and the Galleon Group, Steven A. Cohen and SAC Capital, KKR’s RJR Nabisco buyout, and how to manufacture luck

What I’ll do next week:

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

Asks:

• No ask this week

Week two hundred eighty-nine 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:

• No material struggles last week

What I learned:

• The most important thing I learned about last week is OpenAI adding apps to ChatGPT. I shared a few thoughts on this yesterday (see here). I’ve been thinking about it a lot. It has the potential to change how businesses get discovered and acquire customers. Just as Google search changed marketing and Apple’s App Store created the market for independent developers to sell apps, this could be a game-changer. I’ll follow it closely as OpenAI releases more information.

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

A friend sent me a link to an OpenAI press release (see here). This past week, OpenAI held its developer conference, where it shared new products and technical capabilities. The press release announced the launch of apps in ChatGPT. Developers can now use a new apps software development kit (SDK) to allow users to access external apps from within ChatGPT. What does that mean exactly? Zillow is one of the launch partners. If you’re using ChatGPT to ask residential real estate–related questions, ChatGPT can access the Zillow app and use data from Zillow to enhance your ChatGPT session. In short, you’ll soon be able to access your favorite apps from ChatGPT.

Why This Matters

ChatGPT has 800 million active weekly users, according to Sam Altman (see here). Getting exposure to that number of potential customers is a huge opportunity for companies.

ChatGPT users can ask for third-party apps by name (e.g., “pull in Zillow data”). But ChatGPT will also recommend apps based on a user’s questions, which are a signal of intent. High intent increases the probability that someone will use and get value from a third-party app (say, Zillow) when it solves a pressing problem or answers a pressing question. Intent-based discovery is a big opportunity for other companies to find new potential customers via ChatGPT.

This all just happened this week, but if ChatGPT executes this well, it could create an app ecosystem that helps tons of third-party app companies acquire new customers when the customers most need what the companies have to offer.