The book The Money Masters: Nine Great Investors: Their Winning Strategies and How You Can Apply Them by John Train introduced me to Thomas Rowe Price Jr. (aka T. Rowe Price). I’m familiar with the investment firm bearing his name but not the man himself. I wanted to learn more, so I’m reading T. Rowe Price: The Man, the Company, and the Investment Philosophy by Cornelius Bond.

The book says that Price was one of the first investors to recognize the value of growth investing and adopt it as a strategy. After the Depression began, many people focused on preserving capital, so bonds were popular. In 1934, he recognized that the largest fortunes in the country had been created by owning growing businesses. He developed an investment strategy based on this insight and pitched the investment firm he was working for to test the approach.

With the country still feeling the Great Depression, the firm turned him down. Frustrated and having conviction about his approach, Price quit in 1937 to launch his investment firm, which would become T. Rowe Price Group.

After reading several biographies about famous investors, I’ve noticed that they all came to similar realizations about their investment approaches: investing in growing businesses is the key to outsize returns (Price’s biography details why this works so well). However, how these investors executed their strategies and built their firms varies drastically. Price built a firm that made decisions by committee and was paid by fees from customer accounts. Buffett created a decentralized conglomerate (after he shuttered his investment partnership) and increased his wealth through equity ownership in the conglomerate.

There’s more than one way to capitalize on an insight, as the stories of these investors prove. The most important thing is doing so in a way that aligns with the beliefs of the founder of the investment firm (or the investor, if they’re independent).

I’ve been struggling to articulate the problem I’m solving with my “book library” project. It’s critical to clearly state the problem in such a way that people will understand why it’s worth solving. When you can do that, people are more engaged and want to hear about your solution. But I wasn’t doing it, so I had to fight to keep people’s attention. And this was when I was talking to friends, not strangers, and I wasn’t asking them to use or pay for the solution.

I decided to use the holiday to review all my notes and start crystallizing the problem in a clear sentence. Creating a problem statement is something that sounds simple, but it’s been hard for me in the past. Getting to a concise statement is usually a process of refinement and wordsmithing. In the past, I’ve done it alone (with no success) or with a group of entrepreneurs as part of a retreat.

I didn’t want to do it alone and had no planned retreats, so I decided to use Google Gemini and ChatGPT as thinking tools. Both offer mobile apps that allow you to speak your thoughts instead of typing them. For this kind of ideation exercise, I wanted to capture my thoughts as they were flowing, so speaking was key.

I chose to use two models because no model is perfect. They all have strengths and weaknesses. But I’ve found that feeding my thoughts to both, reviewing their outputs, incorporating the outputs into my thinking, feeding my updated thoughts to both, and repeating that loop has worked well. I also ask each model to rate and give feedback on the output from the competing model. Together, this created a rapid iteration cycle, something I can’t normally do alone.

After many cycles, I’ve finally landed on two versions of what I think is a clear problem statement. I feel pretty good about both, but I’ll get feedback before I make final decisions.

Clearly articulating the problem sounds like an obvious thing that all entrepreneurs do, but many don’t have clear problem statements, which causes lots of issues down the road.

A few days ago, I shared that a founder friend suggested that I start my book library project with the end in mind—that is, with the desired output. The idea was that since I’m building a solution to a problem I’m experiencing, I’m in a position to produce hypothetical examples of the kind of output this solution could create that would solve the problem.

I've created three hypothetical outputs over the last few days. I wasn’t sure how to approach this at first, but I decided to base it on my journey with this project so it’s somewhat grounded in reality. I started with problems I’ve solved for myself during this journey or am actively trying to solve. For two examples, using problems I solved the old-fashioned way with the help of my notes and highlights from various biographies, I figured out the ideal outputs that would have gotten me to the same results more efficiently.

This was a fun exercise. Having already solved the problems, figuring out how this solution could have helped me get there more efficiently was interesting. What kind of information should it have provided to me? What kind of questions should it have asked me to get me thinking? What stories needed to be shared for suggestions to resonate with me?

I shared these outputs with my developer friend today. Having them to work backward from led to a productive discussion. We narrowed our focus to what must be built to make those outputs a reality. We realized that a structured approach to solving certain problems is required for consistent results. This reinforced the importance of data structure.

This exercise has been helpful and something I want to do going forward when I’m trying to build a solution to my own problem. I’ve got three example outputs that are complete now, and I’ve got another two or three that I want to document before the end of the year.

This past weekend, my developer friend and I chatted with a founder friend about the book library project. This founder has a unique perspective because he’s a self-taught developer, a trained designer, and a self-taught user experience (UX) person. He can take a product from idea to launch by himself—and has done so successfully by scaling and selling a software company—so he has credibility.

I wasn’t sure how the user experience should flow, so I wanted his input. The conversation was helpful, and he made a key suggestion: since the solution is being built to solve a problem that I’m experiencing firsthand, I could start with the output I’d be happy to see as a user instead of starting with the user experience. That is, I could create hypothetical examples of what kind of output I’d want this solution to create that would be tremendously valuable to me.

His point was that we could work backward to determine what the UX would need to create the output. But also, looking at this way would inform what would technically need to be built to create that output. My developer friend and I agreed that’d be a great exercise, so I’ve been working on it.

Doing this analysis has been a great exercise. It’s forced me to think about how the tool will improve my current workflow and, hopefully, that of other users. With so much information in so many books, whittling it down to the key pieces of valuable information in response to a specific question was thought-provoking. Thinking about how information and the connections between it (ideas, people, books, etc.) should be presented and how to do this without drowning myself in information was eye-opening.

I’ve completed one of these, and I’ll do a few more. A big takeaway is that the connections between information in various books make the library unique and valuable. Connections can uncover new insights. New insights help entrepreneurs develop unique solutions to problems or identify the unconventional next action to take given their goals. Today, the people who are able to take advantage of this process are mainly those gifted with a photographic memory, which isn’t me (more thoughts on that here). Showing these connections can’t be done using only text. A visual component allowing people to easily see the connections from a high level and decide where to double-click is necessary.

I’m a big proponent of starting with the end in mind and working backward, but I didn’t do a great job of doing that with this project. My friend pointed out that since I’m experiencing the problem myself, I’m too close—it’s hard to see past the details and stay focused on the big picture. He’s right. His suggested exercise is forcing me to articulate what will add value and how it looks. This will help my developer friend and me reprioritize the features and also highlight shortcomings in what we’ve already built and plan to build.

Sometimes, bringing in a fresh pair of eyes to look at things from 50,000 feet can be helpful. I’m glad my friend made the time to chat and share his candid feedback.

Today, I caught up with a founder friend who sold his software company for a few hundred million dollars. As entrepreneurs do, we started talking shop about business ideas and what each of us is working on. I pitched the idea of the “book library.”

I’ve talked to him about this project as it’s evolved throughout the year, and he’s been skeptical each time—rightfully so, because I wasn’t clear on many things. Today was different. He listened as I described the MVP I was building. He immediately got it. He had some great questions and great feedback.

One big point he brought up was that though entrepreneurs often have hair-on-fire problems and want ideas about how to solve them, there’s also a desire for ideas about the tactics of executing solutions. He gave an example: needing to reduce burn. The solution could be to significantly reduce the workforce (which he’s done). Most entrepreneurs don’t do that often, so they’d want to understand the nuances of executing the reduction in a way that treats employees as well as possible. To fill this tactical knowledge gap, most entrepreneurs learn from others who’ve recently made a reduction or botch it and learn from their own mistakes.

His points were valid and got me thinking. There’s a difference between tactical learning and strategic learning. Tactical learning involves learning what’s working in the current environment. And tactics are constantly evolving. Strategic learning is about learning the concepts and frameworks that solve problems that all entrepreneurs encounter. Strategies do evolve, but they tend to be more timeless. The bid ideas around marketing haven’t changed in decades, but how those strategies are executed continuously evolves. Marketers advertised heavily in newspapers forty years ago, but today it’s Google and Facebook.

I wasn’t aiming to provide entrepreneurs with a library of tactical wisdom. I feel like many resources, such as YouTube, make tactical learning accessible. But my friend got me thinking. The application of wisdom is a big thing entrepreneurs struggle with. Am I overlooking an opportunity to bring massive value to entrepreneurs by not including tactical wisdom? I’m not sure now, but I want to think about this more, with an open mind, during the holidays.

Last week, I shared that I want to learn more about psychology to improve my decision-making and because it seems like a fun topic. Charlie Munger famously studied the failures of others to understand thinking errors. That approach resonates with me, and I decided it’s best to start by regularly analyzing my own failures. I wasn’t sure how, though, so I started looking for ways others have done this.

I started rereading The Warren Buffett Way by Robert Hagstrom and found a great idea. Hagstrom says that Buffett included in his Berkshire Hathaway annual shareholder letter a section called Mistake Du Jour. In it, he “confessed not only mistakes made but opportunities lost because he failed to act appropriately.” He was transparent about his mistakes and shared them broadly.

I’m a huge fan of update emails (see here, here, and here). But I can’t recall ever seeing an update email with a section dedicated to the founder's mistakes. The more I thought about it, the more I thought it’s brilliant. It’s a great way to make a habit of analyzing your own mistakes—and also to build trust with others and maybe even get unexpected advice based on how other people navigated similar mistakes.

My weekly update blog posts are inspired by update emails. Including a mistake du jour–type section in them would be cool. It would check the box regarding forming a habit to analyze my mistakes and force me to crystallize and communicate them concisely. If I also force myself to include the lesson learned, this could be even better. I’m not sure about some things and need to think about them (e.g., will I have enough to do this weekly, or should I do it monthly?). But I like this idea and want to add my mistakes to my 2025 weekly updates.

One thing that resonated with me in Warren Buffett: Inside the Ultimate Money Mind was the idea of studying failure. The book mentions that Charlie Munger studied failure to improve his decision-making. Munger studied the failures of others as a way of understanding thinking errors, which is studying psychology.

This got me thinking. I want to be more intentional about studying failure. I get excited about hearing what worked from entrepreneurs, but I need to be equally (or more) excited to learn about their failures and the why behind them. I’m really curious about psychology and want to keep improving my own decision-making, so this approach is appealing.

I think the first step is to regularly analyze my own failures and mistakes. I’m going to put some thought into ways I can make this a habit and see if I can adopt strategies others have used successfully.

In a post last week, I shared an unexpected data issue with the “book library” MVP project. The book databases we planned to use have quality issues. Lots of other companies use the data, so it’s not terrible, but it’s not ideal. I initially saw two paths: we can use data with flaws, or we can build a pristine data set from scratch.

I thought about it, and I decided to do both. I want to keep things moving, so we’ll start with the data from the existing book databases. That will allow us to launch the MVP’s next version faster. The data won’t be 100% accurate and might limit what features can be built. But the starting database will have a limited number of records, and we’ll start with a small number of early users. It won’t be perfect (and doesn’t need to be), but we can get something out and start the feedback loop sooner, which will lead to improvements.

After that phase, we can tackle creating a pristine database (if it’s needed). The learnings from the prior phase should also help us figure out what features to build or, more importantly, not build, around the pristine data.

I’m reading Warren Buffett: Inside the Ultimate Money Mind, which is a book about the mindset of Warren Buffett and other investors. One of the things it discusses is how Buffett and other investors make decisions. Robert Hagstrom points out that to understand psychology is to understand human decision-making. That’s why successful investors like Charlie Munger studied psychology to improve their own decision-making.

I’ve never thought much about psychology,  but this book got me thinking about it in relation to entrepreneurship—specifically, entrepreneurial wisdom. In this post, I shared that wisdom is the ability to apply knowledge in a manner that aligns with the outcome you desire. Wisdom means changed behavior and improved decision-making—knowing what to do and when to do it.

I’m always looking for ways to improve my decision-making (and share what I learn). But I’ve never really thought about trying to understand psychology to accomplish this until now. Hagstrom has me interested in learning more about psychology.

I’m going to try to find one of two books about psychology and add them to my reading list.

My book project started with me reading biographies about entrepreneurs and sharing what I learned. During that process, I realized there’s no central repository of all the wisdom of entrepreneurs who came before us. I decided to create one and came up with this mission:

Create a library of wisdom from notable entrepreneurs that current entrepreneurs can leverage to increase their chances of success

This project is super early, but I’ve been thinking about the impact it could have. The thing I keep coming back to is economic mobility. Starting a business that becomes successful is the fastest way to climb the economic ladder, which is why I think entrepreneurship is such a powerful force. Families who struggled financially for generations have seen their circumstances change in a few years because they started a successful business. There are numerous examples of family patriarchs and matriarchs starting businesses and their families still benefiting economically many generations later. Their descendants have continued to climb the economic ladder because of their business (or the resources it created).

Entrepreneurs still must do the work. There’s no substitute for execution and no shortcut to it. But if this project is successful, I can see it boosting many entrepreneurs. Making learnings of notable entrepreneurs easily accessible and helping other entrepreneurs figure out how to apply them could accelerate their velocity and increase their chances of success. If more entrepreneurs are successful, more people, and their families, will experience economic mobility and, hopefully, economic independence.