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.

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: 83
• Total blog posts published: 546

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed in the week ending 10/5/25 (link to the previous week’s commitments):

• Read The Great Inflation and Its Aftermath, a historical book focused on the policy and decisions that caused massive inflation and disinflation from the mid-1960s through the early 1980s
• Added five more books to the library on this site (see more here); these, which I read in 2023 and 2017, were about Ray Dalio, Michael Milken, Seth Klarman, Steve Schwarzman, and Long-Term Capital Management

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-eight was another week of learning. Looking forward to next week!

Every week, I post an update of what I’m working on and what I’ve accomplished. I’ve been doing some form of this weekly update for several years. Yesterday, I realized that I forgot to do an update for the week ending September 28, 2025. So, I published that week’s update today. You can see it here.

I still need to share an update of last week (week ending October 5), and I plan to publish it before the weekend. That means you’ll see two weekly updates in the span of a few days. It’s not a mistake; it’s intentional (kinda). Hopefully this makes sense.

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: 82
• Total blog posts published: 539

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed this week ending 9/28/25 (link to last week’s commitments):

• Read Positioning, a framework for thinking about perception and using it to own a position in the customer’s mind from a marketing perspective
• Added four more books to the library on this site—see more here; these, which I read in 2018 and 2017, were about financial crisis winners, open-book management, and mental clarity

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-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:

• No material struggles last week

What I learned:

• Last week I shared what I learned about Pipecat and Livekit, two open-source orchestration frameworks that can be used to build real-time voice and multimodal AI agents (see here). This week I learned about turn detection: “determining when a user begins or ends their ‘turn’ in a conversation.” Turn detection makes for polite AI conversations—AI and the user don’t talk over each other because the AI waits until the person is done before it speaks.
• The best conversations between entrepreneurs aren’t polite. They’re high-energy. Ideas are shared rapid fire. One entrepreneur’s idea sparks more ideas from the other. They interrupt each other. They talk over one another. These types of conversations, replicated using the above frameworks and paired with a library of knowledge from biographies and other books, could lead to entrepreneurs having great thinking or sparring sessions with AI.

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

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 82 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. This 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 eighteenth weekend, and I added five more books:

• Principles by Ray Dalio
• Den of Thieves by James B. Stewart
• When Genius Failed by Roger Lowenstein
• Margin of Safety by Seth A. Klarman
• King of Capital by David Carey and John E. Morris

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