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: 89
• Total blog posts published: 588

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed in the week ending 11/16/25 (link to the previous week’s commitments):

• Read The Checklist Manifesto, a framework for improving how you think and act by reducing errors of omission—missing critical steps under pressure—and errors of ineptitude—failing to apply what you already know

What I’ll do next week:

• Read a biography, autobiography, or framework book
• Pick my next weekend project and start working on it

Asks:

• No ask this week

Week two hundred ninety-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 related to this project

What I learned:

• Some people learn best in group settings, while others learn best when they have time to reflect alone. Entrepreneurs seem to tilt more toward the former. They build on each other’s insights to accelerate their learning. Conversely, investors tend to be in the latter camp, which makes sense when you think about it. Their goal is to get above-average returns. If they do what everybody else is doing, their results will be average, by definition.

That’s what I learned and struggled with last week.

I looked at the books I’ve read over the last few months and realized it’s been mostly framework books. That’s likely a reflection of two things: I was trying to understand or solve something, and I went down a rabbit hole when one framework book led me to a related one. This is especially true of Michael Mauboussin’s books—I read four of them in five weeks.

I got a ton out of these framework books, but I do want to get back to reading more biographies and autobiographies because of the personal stories in them. Personal stories are what make these books special.

The year will be over soon, and I want to read more personal stories before it ends. I’ve decided that I want at least half the books I read in the next few weeks to be biographies or autobiographies.

Some pages of specific blog posts weren’t loading correctly. In fact, some pages weren’t loading at all or were only partially loading. As a result, the page would freeze on some desktop and mobile browsers. My friend looked into this, found the root cause of the problem, and fixed it. As of now, all blog post pages should load quickly on all devices.

If you’re still seeing this issue (or any other issue), please let me know so I can fix it.

Since reading The Success Equation, I’ve been thinking about how I can improve my chances of future success. Understanding where the things I’m thinking about fall on the luck-skill continuum has changed both how I think about them and my expectations. A lot of things I want to accomplish as an investor and entrepreneur are materially influenced by luck, so I need to hone my decision-making process to increase the chances of getting the outcomes I want.

I’ve also been thinking about past outcomes—both good and bad—to determine how much luck and skill factored into them. When an outcome was good, I generally assigned too much weight to skill. The truth is that skill played a role, but factors outside my control heavily influenced many outcomes. I couldn’t predict that things would happen the way they did. But they did, and I benefited from them. I’ve had more luck on my side than I’ve previously acknowledged when outcomes were good.

When an outcome was bad, I assigned too much weight to luck. In reality, it’s been a mix of skill and luck. In some instances, I didn’t have sufficient skills to get the outcomes I wanted and thus failed. In others, luck just wasn’t on my side.

It’s interesting to think about outcomes in terms of the influence of skill and luck. I’m glad I read this book and can’t wait to use its analysis to evaluate future decisions.

I first read Expectation Investing by Michael Mauboussin this past summer, and I ended up reading that book twice and starting to read all of Mauboussin’s other books. This post is about the fourth of his books that I’ve read in the last few months, and it didn’t disappoint.

The Success Equation is about understanding the impact that luck and skill have on your successes and failures. The book provides a framework for understanding, in advance, how much skill and luck will impact a decision or activity. Understanding how what you want to do is affected by skill and luck can alter your planning, expectations, learnings, and a host of other things.

This book is full of things I’ve found helpful, two of which I’ve written about already:

• Rationality quotient (RQ) matters more than intelligence quotient (IQ)
• How checklists tame luck

Another concept that stuck with me is what he called the “luck-skill continuum.” Mauboussin explained how to gauge the extent to which an activity is influenced by skill and luck by visualizing it on a continuum. He then explained why the sample size required to draw a reasonable conclusion about future expectations differs for activities heavily influenced by skill vs. luck. He also explained reversion to the mean and why it impacts activities of skill and luck differently. I have lots of notes and highlights in the chapter on the luck-skill continuum that I’ll revisit often.  

This book was a great read. Anyone interested in improving their chances of success by improving their decision-making should consider reading The Success Equation.

I’ve started on my new weekend project: cleaning up the images of all the books that I’ve uploaded to this site. Several issues need to be resolved, including these two:

• Load time – It takes too long for the page listing all the books I’ve read to load. This causes the list of returned books to be incomplete, the count to be wrong, etc. Part of the issue is that some book cover images are too large.
• Social sharing – When a link to a book page is shared via text message or social media, the link should load the book cover image. That isn’t happening consistently. I know of two reasons for this: an improper file type and a too-small file size.

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To fix these and other issues, I’ve been going through all the book cover images and changing the file type, renaming the file, compressing the file, etc.

I should complete this project by the end of November at the latest. I’ll provide more details on what I’m doing and my progress in later posts.

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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: 88
• Total blog posts published: 581

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed in the week ending 11/9/25 (link to the previous week’s commitments):

• Read The Success Equation, a framework for improving your decision-making by understanding how luck and skill impact outcomes

What I’ll do next week:

• Read a biography, autobiography, or framework book
• Pick my next weekend project and start working on it

Asks:

• No ask this week

Week two hundred ninety-three was another week of learning. Looking forward to next week!

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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 related to this project

What I learned:

• When it comes to learning, the human element can’t be replaced. It may be possible to come somewhat close to replicating the process of learning by talking with others, but you can’t fully replicate it. Therefore, people will always prefer interacting with other humans over other forms of learning.

That’s what I learned and struggled with last week.

This week I had lunch with a group of entrepreneurs. One of them, a CEO, had a pressing issue he wanted input on. He had a few million in revenue and was having trouble finding a firm to handle his company’s marketing. They all pitch the same strategy, which doesn’t resonate with him. He’s frustrated and wanted to know what other founders have done to get their marketing efforts off the ground.

When clarifying questions were answered, we learned that the CEO’s focus has been solely on outsourcing the marketing function to an agency. He wants to achieve a specific output or goal and wants an agency to figure out how to do that.

The feedback from founders centered on two points:

• You can’t outsource marketing entirely. It’s hard for an external company to develop a strategy when they don’t have a great understanding of your customer or the problem(s) you solve for your customers. Some founders have had success hiring a full-time marketing leader, who developed the marketing strategy and outsourced some tactical work to agencies. The function and strategy were owned internally by a full-time company employee.
• Deep understanding of the customer, their problem, and their journey lives with the CEO. It’s the CEO’s job to get others in the company to understand those things too and, in the case of marketing, to create appropriate strategies. The CEO can hand his or her understanding off to marketing, but it’s not realistic to expect marketers to develop that understanding and the messaging around it.

I’m no marketing savant, but I’m actively learning to understand it better. Based on my past mistakes and what I’ve read from marketing thought leaders, I agree with these points.

The feedback was useful to the founder with the problem, who walked away thinking differently about marketing. Instead of outsourcing, he’s now considering finding someone to lead his marketing strategy. He’s also thinking about how to convey his deep understanding of the customer’s journey on day one to his new marketing lead so he can set them up for success.