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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.
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What I Learned Last Week (9/14/25)
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:
- The lawsuit by a group of authors against Anthropic, parent company to Claude AI, resulted in a $1.5 billion settlement last week. I’m still learning about this and similar cases brought against firms like Anthropic. From what I can tell, using books to train the Anthropic models isn’t what got Anthropic in trouble. The lawsuit was for copyright infringement and Anthropic not compensating the creators of the copyrighted books. Anthropic used pirated books to train its models, which means authors weren’t paid for the use of their books in model training, a key issue that appears to have led to the settlement. I get the impression that if Anthropic had purchased the books, it could have used them freely to train the models because the authors would have been compensated for the use of their copyrighted work.
That’s what I learned and struggled with last week.
Weekly Update: Week 284
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: 79
- Total blog posts published: 518
This week’s metrics:
- Books read: 1
- Blog posts published: 7
What I completed this week (link to last week’s commitments):
- Read The Harder You Work, the Luckier You Get, Joe Ricketts’s memoir detailing his journey to found Ameritrade, pioneer the discount brokerage model, and sell Ameritrade for over $2 billion
- Added four more books that I read in 2019 and 2018 to the library on this site—see more here; they were about an empire built on cocaine, how twins turned their Facebook winnings into a billion via Bitcoin, the Theranos fraud, and how Ross Ulbricht built the Silk Road and got arrested
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-four was another week of learning. Looking forward to next week!
What I Learned Last Week (9/7/25)
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:
- 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.
The Weekend Project That’s Taking All Year
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.
Weekly Update: Week 283
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!
What I Learned Last Week (8/31/25)
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:
- 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.
Labor Day Challenge: Log 4 Books in My Library
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!
2,000 Consecutive Daily Posts
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!

Weekly Update: Week 282
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: 77
- Total blog posts published: 504
This week’s metrics:
- Books read: 1
- Blog posts published: 7
What I completed this week (link to last week’s commitments):
- Read Technological Revolutions and Financial Capital, a historical recount of the relationship between financial bubbles and new technologies. Venezuelan economist Carlota Perez describes a cycle driven by the relationship between the two that can be traced back over one hundred years.
- Added two more books that I read in 2019, these an inside perspective on angel investing and a biography about the opioid crisis and one of America’s biggest pain clinics, 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-two was another week of learning. Looking forward to next week!
What I Learned Last Week (8/23/25)
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 this week
What I learned:
- Many AI entrepreneurs leverage models from OpenAI, Anthropic, and others. They access them via API and build solutions on top of them. Some students at top engineering schools are building their own models from scratch and completely avoiding using OpenAI and other well-known providers of LLMs.
- Speed is one of the biggest advantages entrepreneurs can have. The faster they can move, the more experiments they can run. The more experiments they run, the more they learn and the closer they get to an ideal solution. Reading is pretty slow, but books contain solutions to many problems entrepreneurs face. Helping entrepreneurs quickly sift through books to find the right piece of information at the exact time they need it is tremendously valuable to them.
That’s what I learned and struggled with last week.