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 shared my decision to pick up the pace on my weekend project—updating my library—so I can finish it by mid to late October.

Last weekend, I set a new goal: add a minimum of four books each weekend until I’m done. If I have the bandwidth, I’ll add more.

This project has been fun, but I’ve started thinking about other things that also would be fun, and I’m ready for a new project. This one began at the end of May (see here), so if I wrap it up in October, I will have worked on it every weekend for five months with no breaks. To date, I’ve added 132 books to my library.

I’m in the final stretch. Wish me luck!

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 80 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. Quite recently (see here), I decided to up the pace so I can finish this project well before the holidays—and begin another one!

This past weekend was my sixteenth weekend, and I added four more books:

• The Goal by Eliyahu M Goldratt and Jeff Cox
• Red Notice by Bill Browder
• The Frackers by Gregory Zuckerman
• The Smartest Guys in the Room by Bethany McLean and Peter Elkind

That’s the latest update on my weekend goal. I hope that sharing these books will be of value.

Last week I shared that I read a biography of Joe Ricketts, founder of Ameritrade (see here). One of his main competitors—and the company that acquired Ameritrade in 2020, over a decade after Ricketts sold it—was Charles Schwab Corporation. I was intrigued and wanted to learn more about the discount brokerage model and the era that birthed the model, so I read the autobiography of Charles Schwab.

Invested describes sixty or so years of Schwab’s journey in his own words. Interestingly, what eventually became Charles Schwab Corporation started in 1962 as a biweekly investing newsletter called Investment Indicators. Annual subscriptions were $60, and at its peak it had about 3,000 subscribers. No money management, just overviews of the economy, insights on select growth stocks, and hypothetical portfolios.

This newsletter catered to independent investors who were smart and capable of making their own decisions. The understanding gained from serving this demographic formed the foundation for what Schwab built over the next sixty years: a place for individual investors to manage their own investing.

Schwab’s journey to build his namesake firm and amass a personal fortune worth over $10 billion had its share of ups and downs. He does a great job of describing each segment of his journey and how he navigated its specific challenges in detail. He also describes what it’s like to navigate multiple stock market crashes when you run a brokerage that makes money from stock trades (spoiler: volume dries up, the brokerage business gets hit hard).

The most interesting aspect of his journey to me was his position in the early 1970s, when he was in his mid-30s. He described himself as “floundering.” He had zero assets and lots of debt. He was recently divorced, had young kids, and was living in a one-bedroom apartment while still trying to build his then floundering firm. Close to giving up, he began attending evening law school classes. But he pushed through and, with some lucky breaks in 1975, had a vision for a new model for individual investors, the discount brokerage.

I’m super interested in understanding the 1968–1982 era, and this book provided another great entrepreneurial perspective of the era and how to navigate challenging macro times.

If you’re interested in learning about Charles Schwab, Charles Schwab Corporation, the asset management industry, or how a nontechnical founder built what I consider a tech company, consider reading Invested.

A few months ago I met with an early-stage founder about his growth strategy and his messaging. He hasn’t found messaging that attracts his ideal target customer profile, so he isn’t growing at the rate he’d like. We discussed some ideas and his current sales pipeline. He told me about a new outbound sales strategy that wasn’t part of his original plan, but it’s working. He’s working with a company that specializes in providing sales development representative (SDR) services to clients who don’t have dedicated SDRs or sales teams. It finds prospective customers, does cold outreach to them, and sets up demos on behalf of its client companies. It gets paid only when it books demos with prospective customers that it sourced. Said differently, it eats what it kills.  

This founder is having early success with this firm. I wondered how this SDR firm is finding the right type of prospective customers. What messaging is it using? Turns out, the founder had given it high-level information about the problem he’s solving and the solution he built. He instructed it to come up with fresh messaging that it believed would be effective in landing demos. The firm created new messaging based on what the founder provided.

Creating messaging is hard. Founders and their teams who’ve been in the weeds working on a product for months or years may struggle to come up with great messaging because they’re too close. It may be challenging for them to view things from the perspective of someone unfamiliar with their company or solution.

Working with an outside firm whose incentives are aligned with yours but that brings a fresh perspective is an interesting hack to get better messaging. You both want the same thing—more sales—but it’s able to see your solution from a perspective you can’t, which enables it to create on-target messaging easier than you or your team.

It sounds counterintuitive, but the more I think about it, the more sense it makes. An outside sales firm will take what you’ve built and explained to it and come up with simple messaging that’s more effective because it understands the outsider’s perspective (that is, the customer’s perspective!) better than you or your employees do.

This early-stage founder may have found an interesting way to solve his messaging problem in a cost-effective way. He pays only when good messaging created by an outside firm leads to demos with prospective clients. He doesn’t have to pay one firm to create the messaging and another to book the demos. He’s getting a two-for-one deal.

Today I met with another early-stage founder, and the topic of customer discovery came up. He said he’d done discovery, so I dug in and asked more questions. Two things stood out to me that we discussed in detail.

First, most of his customer discovery came from sending out surveys. (I shared my thoughts on surveys as customer discovery earlier this week—see here.) We discussed the benefits of doing more one-on-one conversations.

Second, a lot of his insights were based on a conversation he’d had with one customer. He’d built a lot of his product offering and website messaging in response to what he’d heard in this conversation. Learning from a conversation with a potential customer was a big plus. But one customer doesn’t confirm a pattern that leads to previously undiscovered insights.

Surveys are good, but not for initial discovery. Conversations are the best way to learn about pain that potential customers are experiencing. And you need lots of conversations with lots of people to uncover patterns and gain a deep understanding of problems and why they’re so painful.

I had a good conversation with a friend this week about the number of recent IPOs. He’s a physician, so this really caught my attention. If someone who isn’t a professional investor or entrepreneur is noticing the increased activity, it’s noteworthy.

I’ve noticed the uptick in IPOs and public market investors being receptive to buying shares in these companies over the last few months. Several companies have sold shares above their target range, meaning the company’s valuation and capital raised were more than anticipated. Positive signs like that excite entrepreneurs and investors to pursue more IPOs.

Though the IPO market is picking up, we’re nowhere near 2021’s gargantuan levels (see here). I’ll dig into the year-to-date IPO stats and share what I find. The end of Q3 is right around the corner, so I’ll likely wait until then.

This week I listened to the founding team of an early-stage startup describe their current traction. They’ve built a software product and have thousands of (nonpaying) users. To determine what features their customers would pay for, they sent them a survey. Twenty-five percent of the people who responded said they’d pay for a particular feature. So, the company built that feature and launched it recently. The results weren’t good. Only three (yes, three) customers bought it.

So, what went wrong?

The team surveyed customers; they didn’t talk to customers. Talking to customers involves picking up the phone or meeting a customer in person (one customer at a time is ideal). A conversation, if you aren’t leading them, will allow you to dive deeper into the customer’s thought process and experience. It’s iterative. You hear something you weren’t expecting (or didn’t know) and ask questions about it. That leads to something else you didn’t expect, and you ask more questions. The result of that loop is new insights about the customer’s problem. Do that with multiple customers, and you start to see a pattern. You now have a better understanding of the problem and how to solve it for the customer.  

What I described can’t be done with surveys. Surveys may have biased questions that don’t help you understand your customers. And they foreclose iterative interaction with your customers. Sure, they’re efficient and allow you to get a lot of feedback quickly, but the quality is often low, and it can lead you down the wrong path.

The lesson this early-stage team learned was to stop doing surveys of their users and start getting them on the phone. Conversations lead to insights. You can’t have a conversation in a survey.

Earlier this month, I shared that my weekend-only project to update my library won’t be completed until November at my current pace. I could either make peace with that or ramp up my pace to add more than two books per weekend.

Pondering the situation, I decided to finish the project well before the holiday season kicks off. I’m afraid that if I finish in November, I’d be more likely—with all the holiday distractions—to not begin another weekend project. I want to have established the habit and momentum of a new project before the holidays.

I’m going to add more books to the library every weekend. Four, or maybe even five. I’ll test it this weekend and settle on a number. My goal now: complete this project by mid-to-late October.

Wish me luck!

Weekly Update: Week Two Hundred Eighty-Five

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: 80
• Total blog posts published: 525

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed this week (link to last week’s commitments):

• Read Invested, Charles Schwab’s autobiography detailing his founding of Charles Schwab Corporation and how he built it from a pioneering discount brokerage into a financial services company catering to individual investors
• Added two more books that I read in 2018 to the library on this site—see more here; they were about the $5 billion Malaysian 1MDB scandal and the high-stakes underground poker world

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:

• No ask this week.

Week two hundred eighty-five was another week of learning. Looking forward to next week!