My new weekend project begins this weekend. What will it be? I don’t know. I’m still trying to decide what idea to pursue. But I’m leaning toward trying something much shorter in duration so I can get a feel for that type of project. (I want to understand the optimal duration better.) I’m considering doing a one-month project so I can compare that duration to six months. Another advantage would be that I could complete two more weekend projects before the end of the year, for a total of three. I’ll decide in the next day or two, but that’s what I’m leaning toward right now.

I’ve read two books by Michael J. Mauboussin, an investor and a professor at Columbia University. I’ve enjoyed learning and trying his frameworks, especially the expectations investing framework. Another concept he wrote about was the investment premortem, an analysis you do before you invest when you’re objective and your mind isn’t anchored (as it will be after you’ve already invested).

To create this document, you fast-forward a year or so and pretend your investment has failed. You then list all the possible ways the investment ended up in that worst-case scenario. Most people naturally focus on what could go right and their own belief that an investment will work. The goal of the premortem is to get you to consider negative alternative outcomes and ways to mitigate them.

This approach caught my eye, and I want to try it. Thinking in terms of scenarios and the probabilities of those scenarios occurring is something I’ve noticed successful entrepreneurs and investors doing. I’ve started doing more of it, but I want to improve. This premortem idea seems like a great way to force myself to crystallize my thoughts about scenarios that are the opposite of what I hope happens. And it’ll likely help me have more confidence in assigning probability weights to the bad outcomes that I don’t expect.

A friend shared Stripe and OpenAI’s new Agentic Commerce Protocol (ACP) with me. ACP is an open-source interaction model and an open standard that lets buyers, AI agents, and businesses complete purchases. Translation: ACP will enable buyers and sellers to complete purchases, using AI agents, within an “AI surface” (think apps like ChatGPT).

As I understand it, when a buyer wants to purchase within a chat app, an AI agent works with them, showing products, offering checkout, and collecting payment. The business receives order details and payment information from the AI agent and can accept or decline the transaction. The AI agent facilitates payment via the business’s payment provider and sends payment details via a secure token (I assume after the buyer accepts the transaction), which the business can use to charge the buyer. If all goes well, the buyer can check out instantly via an app like ChatGPT without ever leaving it. It’s a seamless experience.

This is interesting stuff that could really change how commerce is done. It’s brand new, and I’m curious to learn more about it and follow its development. If you want to learn more, you can read Stripe’s blog announcement here and visit the ACP website (which links its GitHub) here.

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 85 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 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!

The backlog is finally gone. This past weekend was my twentieth and final weekend, and I added the last two books:

• Liar's Poker by Michael Lewis
• Business Adventures by John Brooks

That’s the latest and final update for this weekend project. I’m glad I took this project on. It forced me to revisit tons of books, which jogged my memory.  I hope that sharing these books will add value to others.

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.