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.

I’ve been working on the next version of the “book library” MVP with a developer friend. Living the problem this past summer by reading, taking notes, blogging, podcasting, etc. is coming in handy. The insights are helping with feature prioritization and nuances around how it’s built.

One thing I didn’t expect that we’re encountering this week has to do with data. We’re finding errors and weird record relationships in book databases that we’d planned on using. My gut instinct is to create our own pristine database by aggregating and cleansing the data from various sources. But that’s a decent amount of work, and I’m not sure we need to do it for what I want to accomplish with the MVP. I’ll think about it some more over the next few days.

This weekend, I was working on the “book library” MVP. I checked X, formerly Twitter, to see if others were experiencing the same pains around reading that I’ve experienced. I came across a thread from a notable CEO complaining about the same pain I’m trying to solve.

Because he’s well known, the thread got tons of exposure, which resulted in lots of replies. The replies were a gold mine. I learned about other founders who’ve built solutions to solve this problem. I started a list of competitors and added each of them to it. I also read every reply because people articulated their perspective on the problem and suggested solutions. I noted the suggestions and added some to a list of potential features.

My takeaway was that X is a pretty good tool for researching a problem, given the crowdsourced nature of the platform. Despite lots of noise and downsides, it quickly helped me find competitors I might not have known about otherwise and get candid thoughts on the problem from users I wouldn’t have had access to.

This week, I received a call from a founder. He’s in a disagreement with the other cofounder of his company. Disagreements between people who spend significant time together regularly are inevitable (e.g., family, romantic partners). So, they’re bound to happen between entrepreneurs, who often have stronger opinions than the average person.

Disagreements between founders can fracture the relationship beyond repair and seriously impact the company if they’re not resolved. Cofounder disagreements are one of the top reasons early-stage companies fail.

These two founders decided to get help from a neutral third party. They hired a counselor who specializes in helping founding teams work through disagreements. Through this process, they got to the root cause of the issues and are now trying to work through them.

I’m hopeful that they’ll be able to resolve their disagreement and the company can get back to focusing on customers.

This week, I chatted with the founder of a growing company. The business is doing well, but he’s uncertain about the future because the business is in a heavily regulated industry. This makes planning more challenging, especially since a new presidential administration will take over here in the U.S. in January.

The regulations he’s concerned about will determine what customers he can sell to. If the regulations are loose, the number of customers he can serve will be large. If they’re strict, the market of potential customers will shrink materially. There are lots of competitors in the market, so loose regulations mean plenty of business to go around for everyone. Strict regulations will lead to steep competition and, probably, price wars, which will reduce profit margins.

So, while he’s watching the regulatory environment, what he’s primarily worried about is the future size of his market. Markets can make or break a company. This founder hopes that regulation doesn’t shrink his market and put his company in a challenging situation.