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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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Books
This Week’s Books: How Joe Ricketts Built Ameritrade and Disrupted Wall Street
Last week, I read about John Bogle’s journey to build Vanguard into an index-investing powerhouse (see here). That biography mentioned discount brokerages having been launched in the 1970s. Ameritrade was one of them, and I wanted to learn more about it, so I read the memoir of Joe Ricketts, founder of Ameritrade.
The Harder You Work, the Luckier You Get is a candid recount of Ricketts’s life in his own words. It details how he went from college dropout to struggling stockbroker with a growing family to founding his own discount brokerage firm in Omaha. Ricketts’s story was interesting because he didn’t found his firm (which ended up being a technology firm) near the financial capital, Wall Street, or the tech capital, San Francisco. He founded and scaled his firm in Omaha, Nebraska. Another thing that stood out to me was how regulation played a huge role in his success. In 1975, the government eliminated fixed commissions on stock trades, which opened the door to negotiated commissions and a new business model that Wall Street had never seen (and wasn’t ready for): discount brokerage. Ricketts and three partners launched First Omaha Securities, the predecessor to Ameritrade, that same year.
Ricketts’s early years were also interesting to me because they align with my interest in understanding the 1968–1982 era. Ricketts provides lots of perspective on this era and on how his firm navigated raging inflation and a bear stock market. A point Ricketts emphasized, and that I’ve read elsewhere, is that between 1968 and 1982, the Dow Jones Industrial Average lost 75% of its value, adjusted for inflation (inflation peaked around 12%).
Anyone interested in learning more about Ricketts, Ameritrade, the stock brokerage business, or how a nontechnical founder built a tech company should consider reading The Harder You Work, the Luckier You Get.
New Books Added: Cocaine, Bitcoin Billions, Start-up Fraud, and the Silk Road
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 by 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.
This Week's Book: John Bogle and $10 Trillion Vanguard
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.
New Books Added: Twitter’s Origin Story, and How to Identify Your Unique Ability
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 by 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.
This Week’s Book: The Real Cause of Every Tech Bubble
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.
New: How Connected Is Each Book?
Books are connected to other books, but it’s not easy to see the connections unless you read an entire book. That makes how books are networked, or connected, invisible. The primary way I discover books is seeing them mentioned in another book. I’m constantly making mental connections of ideas, periods, events, or people mentioned in several books. This blog shows the connections between books, but it hasn’t been easy to understand how many connections a book has . . . until now.
Starting today, when you view the Library page, you’ll notice that next to each book is the number of other books in my library with a connection to it. It’s an easy way to quantify a book’s network. If the quantity of connected books is interesting, you can easily see each connection by clicking “Learn more” to see the book’s profile.
I’m excited about this. I haven’t seen anything like it on other blogs. It’s helped me think more deeply about book connections. I hope that understanding how networked a book in my library is will help people find books they find useful.
If you want to see for yourself, check it out:

New Books Added: How to Angel Invest and America’s Biggest Pill Mill
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 76 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 past weekend was my twelfth weekend, and I added two more books:
- Angel by Jason Calacanis
- American Pain by John Temple
That’s the latest update on my weekend goal. I hope that sharing these books will be of value.
This Week's Book: 19 Investing Principles from Howard Marks
Last week I shared a framework book, Warren Buffett’s Ground Rules, which details the principles Buffett used to run his partnership, Buffett Partnership Ltd, in his pre–Berkshire Hathaway days. When I read that book, it reminded me that few investors who are active today were also actively investing in the 1960s and 1970s, like Buffett.
Another person who meets those criteria is Howard Marks, cofounder of Oaktree Capital. Marks has written two books, one of which I read twice. So, I decided to read his other book, The Most Important Thing.
This book is a framework book that details the investing principles that Marks has learned over his many decades of investing, many of which led to the outsize success of Oaktree Capital. Each chapter is dedicated to one of the 19 principles and explains it thoroughly. My favorite was the chapter on understanding risk.
This book is a good tool for anyone interested in investing or understanding how public markets work. I enjoy Marks’s writing, and this book didn’t disappoint. I’ll definitely read it periodically as a refresher.
New Books Added: Secrets, Crime, and Venture Capital
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 75 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 past weekend was my eleventh weekend, and I added two more books:
- The Mastermind by Evan Ratliff
- Secrets of Sand Hill Road by Scott Kupor
That’s the latest update on my weekend goal. I hope that sharing these books will be of value.
This Week's Book: Warren Buffett’s Playbook Before Berkshire
I’m continuing to lean into my curiosity about the late 1960s through roughly 1982. This was a period of social and economic change. Interest rates were near 20%, and inflation was double digit.
Last week, I shared a biography I read about how Thomas Rowe Price Jr, founder of T. Rowe Price Group, navigated that period. This week, I dug into how Warren Buffett handled it by reading Warren Buffett’s Ground Rules. It was pre-Berkshire Hathaway, so Buffett was managing an investment partnership, Buffett Partnership Ltd. (BPL), and investing other people’s money (his LPs’).
This book isn’t specifically about the period in question. It’s more of a framework that details the principles that governed Buffett’s investments and how he applied them during the years he was actively investing via BPL, 1956 to 1969. The book is unique in that each chapter focuses on a Buffett principle, which is explained and then supported with excerpts from various BPL letters Buffett wrote. It does a great job of explaining his thinking and some of the investments BPL made. It devotes a section to the structure of BPL. It describes the three investing strategies Buffett used at BPL to generate outsize returns: generals (buying generally underpriced securities), workouts (profiting from merger arbitrage), and controls (taking majority ownership to influence a company’s direction).
This book also explains Buffett’s thinking regarding how to navigate the period I’m interested in. I learned that Buffett opted to sit on the sidelines and not invest. In May 1969, he announced that he was closing BPL and would return investors’ money. He went on to send a 17-page letter to his investors in early 1970 about the mechanics of tax-free municipal bonds, which he suggested they invest in. After BPL closed, the stock market experienced a very volatile period with significant declines in several years.
It was great to learn about the early Buffett days, his strategies, and why they worked. It was also eye-opening to see how he sidestepped the period I’m curious about. Anyone interested in BPL or Buffett’s early days should consider reading this book.
