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!

This week, I chatted with a CEO who has a software solution that’s been on the market for a few years. The product is both powerful and complex. It does a lot of things, which is both a gift and a curse. Earlier this year, he was struggling to get traction. This week, though, he shared that things are trending up rapidly; they’ve landed over 10 new customers, each paying roughly $25k a year.

So, what changed? Two things:

• The messaging changed from describing what the product does to describing the problems it solves.
• The company identified several problems that their core customers face and that their solution addresses. Instead of cramming them all on one site, they created a stand-alone site for each problem. Prospective customers with a particular problem can learn more about how this software solves that problem, and they can sign up and try it for free.

All this happened in a two- or three-month period. They didn’t build more stuff; they just focused on the customer’s problems and made it crystal clear, via better messaging, how they solve each of them. Perspective customers now have an oh, that’s for me moment when they visit the site and are converting to paying customers.

Having a great product that solves a problem is critical, but so is the messaging you use to tell the world about what you’ve built.

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 77 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 my thirteenth weekend, and I added two more books:

• Unique Ability by Catherine Nomura, Julia Waller, and Shannon Waller
• Hatching Twitter 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 was listening to The Slow Hunch podcast, on which the founders of the venture capital firm Union Square Ventures (USV) were interviewed. Fred Wilson and Brad Burnham are the founding partners; they shared stories of founding the firm and notable investments such as Twitter, Etsy, Cloudflare, and Coinbase.

Burnham mentioned a framework they used to develop their initial investment strategy. Where he and Wilson thought they were in the period’s technology cycle played a big role in their strategy. It led them to focus on investing in the application layer of the internet because, they realized, the infrastructure phase was behind them. They got this framework from a book Burnham had read. It had a profound impact on him and positioned USV to become one of the top investment firms by identifying the right founders and companies given their understanding of the technology cycle. You can listen to the sections of the interview where Brad talks about the book and how they used it here and here.

This piqued my interest and led to my booking that book, Technological Revolutions and Financial Capital, by the Venezuelan economist Carlota Perez. The book is a blend of a history and a framework. It describes a way of thinking about cycles created by new technology and financial capital and analyzes the five major technology revolutions over the last 250 years and their implications for society: the industrial revolution; steam and railways; steel, electricity, and heavy engineering; oil, cars, and mass production; and information technology and telecommunications.

The core premise of this book is that the combination of new technology and financial capital applied to it creates a technology revolution that leads to speculative bubbles.

According to Perez, each technology cycle lasts roughly 50 years and follows a consistent evolution through three phases:

• Installation. New technology is created, and infrastructure is created to support it.
• Turning point. Speculators’ unrealistic expectations related to the new technology cause a recession or financial crisis.
• Deployment. New technology is distributed widely across society and is accepted, with new rules and regulations being implemented to avoid future crashes.

The book dives deep into the economic and societal impact of each phase, which I found very useful.

Anyone interested in understanding how long technology cycles work, how capital and new technology complement each other, or how speculative technology bubbles work should consider giving Technological Revolutions and Financial Capital a read. It’s dense and full of lots of material that will make you stop and think, so it isn’t a casual read. But Perez’s framing is especially helpful to me as I think about the current AI wave and where we likely are in the long AI cycle.