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!

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.

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!

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.

One of my favorite maxims is from the autobiography of John H. Johnson, founder of Johnson Publishing Company, which published JET and Ebony magazines. Early in Johnson’s career, he worked for Harry H. Pace, CEO of Supreme Liberty Life Insurance. John was upset that Pace had negotiated a settlement with a man who owed the company money and, when Pace tried to collect it from him, was disrespectful to him.

In that moment, Pace told Johnson something he’d never forget:

If you want to succeed in business, young man, you’ve got to learn how to work with people that you don’t like. And you’ve got to learn how to compromise. After you compromise, you have to forget the past and go on to the future. For in business, you have no permanent enemies or permanent friends—only permanent interests.

This quote is powerful. It stuck with me. I took a screenshot of it, and I look at it periodically to remind me to stay focused on my interests and to work with people and compromise to work towards them—even people who aren’t my favorites. I’ve also shared that screenshot with friends when they’re working with people they don’t care for.

To get anything material accomplished in business, you can’t do it all yourself. You must work with people. Some of them you won’t like. But you must figure out how to work with them anyway, compromise, and keep progressing toward what matters to you.