2/26/25 Update: I created a page with all 52 books I read last year. See it here.

2/27/25 Update: I’ve created a searchable library of every book I’ve read and update it weekly. See it here.

This summer, I set a goal of creating 100 podcasts about books I was reading. It forced me to start tracking my reading in a spreadsheet. It’s nerdy, but it was necessary because every week, I read a book, wrote a blog post series, and created a podcast series about each book. The spreadsheet helped me keep everything organized. I paused the latter two after the summer because they were too inefficient and time-consuming, but I kept updating the spreadsheet and reading a book a week.

I looked at the spreadsheet as I was reflecting on the books I read in 2024. I figured I’d share some stats and learnings.

High-level stat for 2024:

• Books read: 52

2024 breakdown by month:

• January: 0 (I did read, but I can’t remember what books)
• February: 2
• March: 6
• April: 6
• May: 7
• June: 5
• July: 4
• August: 5
• September: 4
• October: 3
• November: 5
• December: 5

Here are a few things I learned along the way:

• Reading two books a week was too aggressive. I tried it in the March–May period, but I wasn’t absorbing as much of what I was reading or making as many connections. I was focused on finishing the books, which isn’t why I read. The pace was too fast, so I reduced it to a book a week, which feels more sustainable.
• Sharing what I learned from my reading was the big unlock. It took my learning and thinking to another level. Writing a blog post series and recording a podcast series forced me to identify insights and organize and communicate my thinking. The key tool in that process was creating a digest of each book, which was an extraction of the information I found important in each chapter, along with my insights.
• E-readers, such as Kindles, are great devices, but I prefer reading physical books. I highlight and add notes about insightful sections and ideas in the books. Those highlights and notes are trapped in each book, so finding and using them later is difficult. See here for more. As I’ve read more, this has become a painful problem. Trying to find something sometimes means reviewing several books’ notes and highlights. Experiencing this pain led me to several feature ideas for the “book library.”
• Reading a book is simple—but learning from what I read is more involved. It’s inefficient and involves lots of steps. The process of sharing what I learn from my reading is complex. It’s hard and has many steps and lots of moving pieces. This realization led me to add several more feature ideas to the “book library.”
• The value in reading lots of entrepreneurial biographies is that you’re exposed to the best ideas and experiences of entrepreneurs, and you can pull from them when you’re faced with a problem. The challenge is that this requires a great memory or knowing exactly where to look to quickly find something you’ve read. I don’t have a photographic memory, and I don’t always remember where I read something. I want to make it easy to find what I’ve read, which will be a big part of the “book library” MVP.
• My best ideas in 2024 came from piecing ideas together from various books. Making those connections was a great way to build upon what other entrepreneurs figured out. Solving a problem by building upon the knowledge of others rather than starting from scratch led to my having better ideas. I’m not an idea guy, so this was perfect for me, and I want to do more of it going forward. I don’t think this has to be completely manual and inefficient. Figuring out how to solve this and incorporate it into the “book library” is challenging, but I think it can be done, and I’m excited to figure this out because it’ll be a huge unlock for myself and others.

Those are my takeaways and reading stats for 2024!

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.

This week, I listened to an entrepreneur who’s building a software platform that helps online clothing sellers manage businesses that sell mostly through social media platforms, such as Instagram. The thing that caught my attention was that the company is focused on micro SMB sellers, who make up the majority of this fast-growing market. The company is performing well and has generated over $1 million in revenue.

I’ve shared my thoughts on the micro SMB market before (see here). I think it’s a great market that’s overlooked because people don’t know how to find and convert super-small business owners into customers. There’s no proven playbook. My interaction this week with this entrepreneur further increased my bullishness about this market.

Companies are being built right now to serve this market, and they’ll be massive companies in the next five years. By the time people realize the market opportunity, these companies will be so far ahead and so critical to how the micro SMBs operate that it will be extremely difficult to compete with them.

This week, I met with someone who recently finished their MBA and is trying to decide what city to move to. Their job has given them the flexibility to choose to live in any of several major cities. This person is in their early 30s and looking for not just professional but also personal success. They want to live in a city that will help them in both areas. Succeeding professionally but not having a social life or finding a life partner wouldn’t cut it.

The more I’ve learned from my own mistakes and from reading biographies, the more clear it’s become that your personal network heavily influences the opportunities you’re presented with and your probabilities of succeeding (whatever that means to you). This is true of your personal life, too—the people you socialize with have a big influence on its direction.

I suggested that they go through all the personal and professional relationships they’ve built over the last several years, identify the important ones, and plot the cities those people live in. Then they can count the number of strong personal and professional relationships in each city they’re considering moving to.

My advice was to strongly consider the city that scores highest in strong relationships in both spheres. It’s impossible to predict what any city has in store for you, but living and working where you have the most high-quality personal and professional relationships drastically increases the chances of your finding success in both arenas.

Yesterday, I shared why I love what Andrew Carnegie said about why you should put all your eggs in one basket, which is counter to how most people think. It’s simple, but it’s far from easy to execute. And even if you execute it well, success isn’t guaranteed.

Picking the right basket to put all your eggs in is the hardest part of execution. Whether you’re founding a start-up or making a concentrated investment, this choice is critical. And you must have conviction in your decision so you can weather the inevitable ups and downs. Therefore, you can’t haphazardly pick something based on a whim. You must do the work to deeply understand each of your options. Doing the work often leads to what others might consider an obsession, but it’s what uncovers the insight that others miss—the insight that reduces your risk, tilts the probabilities in your favor, and helps you build the conviction needed to go all in.

Andrew Carnegie’s method isn’t something that everyone is suited for. Making that kind of decision and sticking with it to the end requires mental grit and toughness. But for people with the right mind-set, when it’s done well, it can lead to outsize results.

A friend reminded me of some wisdom attributed to Andrew Carnegie that I’ve always loved because it’s counter to what most people believe leads to outsize success or investing returns:

The way to become rich is to put all your eggs in one basket and then watch that basket.

Mark Twain famously said something in the same vein after hearing about Carnegie's remark (source).

This quote resonates with me because it’s what every wealthy person I know personally did. In either company building or investing, concentration (i.e., extreme focus) on one thing is what led to outsize success. If you focus on one thing, you’re more likely to know everything about it and be able to assess it better than others. You’re likely to spot what others have missed, which reduces risk and tilts the probabilities of success in your favor. When everyone else thinks the chance of success is 10%, you realize it’s 60%.

What I’ve also seen is that after someone has achieved outsize success, they embrace diversification as a means of preservation and reducing downside risk.

Said differently, concentration is for building outsize wealth (or a business), and diversification is for preserving that wealth (or that business).

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!

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.