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I share what I learn each day about entrepreneurship—from a biography or my own experience. Always a 2-min read or less.
Stripe + OpenAI Just Changed Online Shopping
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.
New Books Added: Liar’s Poker and Business Drama Classics
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.
Weekly Update: Week 290
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!
What I Learned Last Week (10/19/25)
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.
Wrapping One Project, Choosing the Next One
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 Week's Book: How to Reverse-Engineer Stock Prices
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.
New Books Added: Creating Luck, Steve Cohen and SAC Capital’s Downfall, KKR’s RJR Nabisco Buyout, and Silicon Valley’s Dark Side
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.
What One Founder Learned Raising $Millions Too Early
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.
Goldman Sachs Buying a $7B VC Firm
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.
Weekly Update: Week 289
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!
