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:

• Anthropic, parent company to Claude AI, settled a lawsuit for $1.5 billion this week (source). A group of authors accused the company of copyright infringement arising from downloading millions of pirated books and training their models with this pirated content. This is a huge settlement in monetary terms, and it could also be a precedent-setting settlement with respect to using book content for training models. Claude is paying about $3,000 per book for each of the 500,000 books covered in the class action lawsuit. That’s pretty expensive relative to the ~$8 that I pay for books (used, of course). It must also destroy the pirated books it downloaded. The good news is that their revenue run-rate went from $1 billion at the start of this year to over $5 billion as of last month and they just raised $13 billion from investors at a $183 billion valuation (source). I want to understand this better and will be digging into the specifics of this and possibly other related cases. This case could have a material impact on LLMs’ ability to use copyrighted book content legally.

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

I’ve been updating my library’s backlog of books since May. Every weekend, I upload two books. I’ve uploaded all the books I’ve read from 2019 to 2023, so, five years’ worth. I’ve still got a few years’ worth of books to do. I was looking at my list and doing the math. Considering this is a weekend-only project, it will likely take me through November to complete it.

I’m enjoying having a project to work on every weekend for a few months. I think I’ll keep up with this habit. It’s given me ideas for other weekend projects that I’m excited about working on. The problem is that I can’t start working on any of them until I finish this one, which is a bit annoying. One thing is certain: I can work on only one weekend project at a time; otherwise, nothing will get done.

I either need to make peace with my current pace and timeline or ramp up how much I do each weekend so I can finish this project and start the next one.

I’m not sure which is the right answer. I’ll think about it this weekend and during the upcoming week.

An entrepreneur friend sold his software company a few years back for over $100 million. We caught up this week, and he updated me on his new company. It’s a non-tech company selling a simple, physical, paper-based product that’s small, light, and easy to manufacture. He started the company about eight months ago and is seeing explosive growth.

The market for this product isn’t sexy, he said, but it’s surprisingly massive. I realized that he’d found a market that’s not attracting the smartest entrepreneurs because the opportunity isn’t sexy and doesn’t attract much attention or publicity. Because of many entrepreneurs’ lack of awareness of this market, they don’t understand the full extent of the market opportunity. The result is that my friend is competing against old-school entrepreneurs who’ve been in the industry for decades and haven’t innovated at all because they haven’t needed to. My friend is running circles around them—so much so that he thinks this old-school industry is going to make him more money than his software company did.

My takeaway is that markets matter a lot, but equally important is understanding the competition in a market. If you can find an overlooked market that’s large, ripe for innovation, and full of players who innovate slowly or not at all, there’s likely pent-up demand for innovation. If you innovate and execute well, the pent-up demand will be unleashed and may slingshot your company to success.

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 78 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 a holiday weekend and my fourteenth weekend. I challenged myself a bit and added four more books instead of two:

• BLOW by Bruce Porter
• Bitcoin Billionaires by Ben Mezrich
• Bad Blood by John Carreyrou
• American Kingpin by Nick Bilton

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

A few months ago, I learned about a biography of John Bogle that describes how he created the index-investing revolution in America by building Vanguard. I didn’t read the book then, but when I heard that he started Vanguard in 1975, I got very interested because that’s in the 1968–1982 Nixon era I’m researching. Eric Balchunas, a senior ETF analyst at Bloomberg who wrote the book, also covers the topics of how Vanguard got into the ETF business and how the mechanics of ETFs work because he was curious about them.

The Bogle Effect is part biography and part history lesson on index investing. It details Bogle founding Vanguard as a way to save his job but then realizing the power of index investing and its potential impact on investors. Fees to buy or sell stock were high in those days, and Bogle’s decision to structure Vanguard as a company owned by the investors in its funds, not Bogle, was a game changer. It led to Vanguard disrupting the Wall Street fee structure, offering the cheapest index investing funds, amassing over $10.1 trillion in assets under management as of April 2025 (source), and employing 20,000 people. I was also interested to learn that even though Vanguard is the leader in index ETFs, Bogle wasn’t a fan of them.

This book gives a great overview of Bogle’s life and personality. It’s also an interesting education on the history of index investing and how it became such a big force in today’s stock market. Anyone interested in either of these should consider giving The Bogle Effect a read.

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: 78
• Total blog posts published: 511

This week’s metrics:

• Books read: 1
• Blog posts published: 7

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

• Read The Bogle Effect, a biography about John Bogle and his journey to found Vanguard and transform it into a pioneer and worldwide leader in indexing
• Added two more books that I read in 2019 and 2018, these about pinpointing your unique ability and the founding of Twitter (now known as X), 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

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

Happy Labor Day!

I hope everyone had a great holiday!

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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 latest AI tools enable users to connect their personal file storage (think Google Drive or Dropbox) so LLMs can use files to create more-tailored responses. Feeding the content of books to an LLM and connecting to something like Google Drive would be helpful to entrepreneurs as they try to solve problems. The LLM would have more context on that entrepreneur’s situation. The downside is that the information in file storage systems is unstructured, which makes it challenging for LLMs to use it effectively and provide consistent responses.

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

I’ve gotten used to setting a challenge for myself each holiday. It’s fun and has pushed me to do more with my off time. Sometimes I hit my challenge goal, sometimes I don’t, but I always learn something.

The Library on this site has been a project for the last few months. It contains all the books I read in 2024 and so far this year, and I’ve been adding those I read before 2024 as a long-term weekend project. I usually add two books per weekend. All the books I read from 2020 through 2023 are in it now, and the total is up to 119.

This long weekend I’m going to push myself to add four books instead of two. Wish me luck!

Yesterday, I hit a milestone with this blog: my 2,000th post. I’ve posted every day for 2,000 straight days—roughly 5.5 years. I started writing because of a challenge (see here). I didn’t know where it would take me or how long I’d do it. Five years later, I’m still at it and thankful that I picked up this habit and stuck with it. It’s become the main way I reflect, think, and crystallize my thoughts and learnings. It’s been a great tool that has helped me evolve and fully embrace lifelong learning. It’s also been a great way to document my thinking and see how it’s evolved.

They say that taking a simple concept seriously can result in outsize results if you stick with it consistently. I’m doing that with this blog. It’s simple, I take it seriously, and I’m sure it will lead to an outsize impact on my life.

Thanks to everyone who has supported me and read my posts. I appreciate it and hope that sharing what I’ve learned has helped you in some way.

2,000 down, 20,000 to go!