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I share what I learn each day about entrepreneurship—from a biography or my own experience. Always a 2-min read or less.
What Reading 51 Books Taught Me in 2025
In 2024, I began reading a book every week. I wanted to share what I’d read, so I posted a recap of my 2024 reading stats and lessons learned (see here). I was frustrated by how hard it was to share a list of all the book titles (see here), so I created a page about each book I read in 2024 (see here). I wanted to replace the Google Sheet I use to track all my reading, so I created a searchable library of all the books I’ve read (see here). I update it weekly.
Last year, 2025, was year two of consistently reading a book every week, and I want to share a recap of my stats and lessons learned. Sorry it’s late (the goal was January).
High-level stat for 2025:
- Books read: 51
2025 breakdown by month:
- January: 4
- February: 4
- March: 4
- April: 4
- May: 4
- June: 5
- July: 4
- August: 5
- September: 4
- October: 4
- November: 5
- December: 4
If you’d like to know what those 51 books were, see my 2025 reading list here.
Here are a few things I learned along the way:
- Reading for general information is critical if I want to generate new ideas—and I do. A Technique for Producing Ideas reinforced this. I have to learn about ideas so I can borrow from them when I’m trying to come up with a new one myself.
- Rereading high-quality books is sometimes better than reading new books. I reread a few books last year, and that helped me a ton. I’m now trying to reread at least one book every month.
- Synoptical reading is key to leveraging books to solve hard problems or deeply understand something. See more here.
- Framework books are a good fit for my personality, and they’re helpful. They give you the framework or process to use when you’re trying to accomplish something. They don’t give you the answer, but they show you how to get to the right answer.
- I get the most out of books when I read with intention; that is, with a clearly defined purpose for reading that book. That purpose should be a problem I’m actively trying to solve or a topic I want to understand better. This year, I’ve started writing down the problem I need to solve or the topic I want to understand before I choose a book. That’s helped me do more synoptical reading and get more from my reading that I can quickly put to use.
- There are no hacks with reading. I have to not only read but also do the work to understand what I’m reading. The best way to do that (that I’ve found so far) is to synthesize a book and share what I learned with others. But I haven’t found a way to be consistent with that.
- Learning through reading doesn’t feel like a chore anymore. It’s something I enjoy doing in my downtime. The personal-growth aspect of it appeals to my curious nature, and I feel like I can sustain it for a long time.
- Application of knowledge is the key to getting better outcomes. A priority of mine in 2025 is to apply what I’ve learned from reading, specifically around decision-making with imperfect information and probabilistic thinking.
Those are my takeaways and reading stats for 2025!
Cash Crunches Can Spark Your Startup’s Best Ideas
This week, I had a long conversation with a founder. He’s been building his start-up for several years, and he relies on government grants for a large part of his operating budget. He’s getting paying customers too, but not enough of them that he can rely solely on that revenue to fund his operations. He has a multiyear grant from the federal government, but those funds can’t be disbursed to him until a certain act that allows a particular agency to disburse funds is passed. The founder was banking on that money to fund 2026, but he hasn’t received the funds yet and won’t until the legislation passes. He’s in a tough spot. He has about 30 days’ worth of cash left. After that, he’ll have to start reducing expenses and headcount.
This isn’t great, but it’s not unheard of for entrepreneurs. Being short on cash, for whatever reason, happens a lot. I’d argue it’s more the norm than the exception. While the times we’re living through can be stressful for founders and their teams, opportunities exist. When everyone knows that the survival of the company (and their job) is on the line, they get laser-focused. People quickly buy into any changes that align with survival and put their all into making them successful. Alternatively, these moments force founders to think about sources of capital from perspectives they hadn’t considered before. Said differently, the crisis forces founders to think creatively about how they can fund their business. I know founders who, faced with cash crunches, launched new products and services that became so successful that they generated most of the company's revenue.
Being short on cash is no fun when you’re an entrepreneur, but when it happens, consider how you can use the situation to think creatively and get your team focused on what matters most.
Zara Founder’s $3.7 Billion Dividend Lesson
Today, I read a Bloomberg article about Inditex SA (see here) that interested me. Inditex, which owns retailers, including fast-fashion juggernaut Zara, was founded by Amancio Ortega sixty years ago. The company is publicly traded, but he owns more than 59% of its shares, according to the article. Ortega is the fifteenth-wealthiest person in the world, according to the Bloomberg Billionaires Index, and has a net worth of around $126 billion as of this writing.
The article I read caught my attention because of the dividend Inditex is about to pay to shareholders, including Ortega. Based on the number of shares he owns, Ortega will receive $3.7 billion. I assume the dividend is based on the prior year’s financial results.
This article highlights that selling your company isn’t the only way to generate cash, even outsize wealth, for yourself. If you build an amazing company that generates a ton of cash, you can maintain your ownership in it, which increases your wealth, and receive dividends (or distributions) from it, which provides cash flow that you can use to pay living expenses or invest in other assets.
Building to sell is popular, but building to hold forever is how many of the world’s wealthiest people created their wealth.
The Interview Question That Instantly Reveals Curiosity
I was listening to a founder describe his hiring process. One of the things he looks for is people who are naturally curious and learn about new things in their free time. I thought this was a great trait to look for in team members (or people in general), but I wasn’t sure how you identify it in an interview. Then he shared what he calls his most important interview question: “What’s the last Wikipedia rabbit hole you went down?”
I instantly thought about the last thing I researched, and sure enough, Wikipedia was part of it. Because of AI, this might change a bit, but I think this is a great question to quickly gauge someone’s level of natural curiosity and how motivated they are to satisfy it.
What I Learned from Sharing What I Consumed Each Week
For over a year, in every Sunday’s post, I shared what I’d learned from a personal project I was working on. This past week, I changed the format of that post, making it broader and sharing where I learned things. More about my thinking on this change here.
It’s early, but one effect of this change was noticeable to me immediately. Creating the new type of post forced me to review all the pieces of content I consumed that week, evaluate which ones added value, and synthesize my big takeaways from each (I need to work on this). This stood out to me because although I often save pieces to review again later in my GTD system, I don’t consistently go back and synthesize them. Creating the post was a forcing function for the review and synthesis of the most-value-added content I learned from.
Not something I thought about before making the change, but definitely a benefit.
Weekly Update: 310
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: 105
- Total blog posts published: 700
This week’s metrics:
- Books read: 1
- Blog posts published: 7
What I completed in the week ending 3/8/26 (link to the previous week’s commitments):
- Read Big Money Thinks Small, a framework book about biases, blind spots, and how to think to be a smarter investor. This book is helpful for decision-making, but it’s tailored more for thinking like a probabilistic investor.
What I’ll do next week:
- Read a biography, autobiography, or framework book
Asks:
- No ask this week
Week three hundred ten was another week of learning. Looking forward to next week!
What I Learned Last Week (3/8/26) and Where I Learned It
I’m trying something new this week. I’m going to share content I consumed and learned from.
What I struggled with:
· No material struggles this week
What I learned:
- 19-year-old makes $400,000 a month – Bloomberg article about how teenagers are becoming millionaires by creating games on Roblox. This is a big market and a trend that isn’t widely known or understood.
- A Wall Streeter bought one of NYC’s biggest clubs – WSJ article about a club that was doing a shocking amount of revenue. After the owners borrowed money, they ended up losing control of the club.
- “College Freshman Sells $50M AI Company” – My previous post includes links to the TechCrunch article and the founder’s X account post about the sale.
- Howard Marks memo: AI hurtles – YouTube video of Howard Marks’s latest memo on AI. This complements his December memo on AI’s ramifications for investing.
- My First Million: The product is you – YouTube video from My First Million, which is about entrepreneurship. Ideas that stuck with me: the concept of the product you’re uniquely suited to build, being you pushed out. Also, I like the impatient-with-action, patient-with-results mindset.
- Alpha Comes from a Differentiated View – YouTube video about investing from someone who worked at hedge funds like Steve Cohen’s Point72. I liked the hit rate vs. slugging thought, being right vs. getting it right, questions to ask when tracking change, and thinking in frameworks.
- Neil Howe on the Fourth Turning – YouTube interview of Cem Karsan and Neil Howe about how differences in generations lead to big societal changes and impact public markets.
- Cem Karsan’s views on current state of stock market – YouTube interview with Cem Karsan. He shares his thoughts about the current stock market and Citrini’s infamous AI report.
That’s what I consumed and learned from and struggled with last week.
What Happened When I Started a Decision Journal
I’ve read several books about decision-making over the last few months. One concept that stood out to me, and that was mentioned in multiple books, is the decision journal. The idea is to write down your thoughts and feelings about a big decision before you make the decision. Later, after you’ve made the decision and the outcome has played out, you can reflect and record your lessons learned. The idea is to record your thinking as it’s happening so you can more easily analyze and spot patterns later. You won’t accurately remember your thinking and feelings if you don’t write them down.
I liked this idea and have wanted to implement it for some time. I finally decided to try it out when I had a decision to make recently. The outcome hasn’t played out yet, but the exercise of writing down my thinking and feelings helped me crystallize which choice was best and why. Since making and executing my decision, I’ve reviewed my thinking and already spotted a few errors. One, my thinking in one area wasn’t as tight as I thought it was, and I could have put in more work into it. Two, how I executed my decision didn’t totally align with what I said I was going to do. Close, but not exactly what I was aiming for.
My takeaway so far is that the decision journal is helpful because without it, I likely wouldn’t have spotted those errors so early or at all. The ability to compare what I was thinking, what I did, and the result should be a great tool to help improve decision-making. I hope this becomes a habit when I make big decisions.
Who Speaks for the Customer at Big Box?
A friend started a new company. It’s not a tech company; he makes physical products to sell to consumers. The products are traditionally sold through big box retailers as the main method of distribution (think Walmart or Target). This poses an interesting problem because consumers don’t interact with my friend’s company. The big box retailers sell tons of stuff, and they aren’t going to spend time trying to understand or get insights from their customers who buy my friend’s products. They’ll share information like sales metrics, and if my friend’s products aren’t selling they’ll tell him that, but they won’t be able to tell him why.
My friend recognizes that not being connected to the end consumer will be an issue. He wants his finger on the pulse of his customers so he can adjust as needed to keep his products relevant to them. Otherwise, their tastes could change, and he wouldn’t know it until his sales at big box retailers decline materially. Even then, he wouldn’t know why.
So, he’s considering adding someone to his team whose entire job is to be the voice of the customer. They’d be responsible for staying in touch with end users of the products, gleaning insights from them, and translating those insights into data that their team can use to make decisions.
I’ve heard of voice-of-the-customer-type roles in software and tech, which I think is much easier to accomplish. There’s often a direct relationship with customers because they’re buying from your website. And there are plenty of tools that help you gauge how customers are using (or failing to use) your products. But I’ve never considered how you keep a finger on the pulse of customers who buy physical products through retailers like Walmart.
I’m really curious about this and can’t wait to see how this plays out for my friend. I think he’s on the right track with his voice-of-the-customer role.
Why Stack Ranking Raises Everyone’s Game
When I was in college, I took a course that was 100% based on group presentations. The goal of the class was to turn people into better team members. The idea was that if you work better in a team, your chances of success in most careers rise. But one thing they had to solve was helping people understand where they stood. Am I a good team member and just need to stay the course? Or am I a not-so-great team member who needs to make serious changes?
Their solution: stack ranking.
At the end of each project, every team member had to rate the rest of their team. The catch was that we had to order group members from best to worst. Each person submitted something that looked like this:
- Sue
- John
- Bob
- Mary
- Tim
Sue got the most points, and Tim got the fewest. After several projects, you began to see a pattern. If you were consistently ranking low, you had to look in the mirror and ask yourself why your peers were consistently giving you low ratings. Your class grade was heavily dependent on your overall ranking at the end of the semester.
That experience was eye-opening. It showed me the power of group members stack ranking each other. Getting a low rating from a teacher was different than getting one from your peers, with all your peers seeing it. The latter felt much worse, partly because it was public but mostly because it came from peers, not an authority figure. No one wants their peers to think less of them. So, what happened was that the stack ranking caused people who weren’t great team members to change their behavior and try to become better team members.
The stack ranking also fostered a competitive dynamic that elevated the effort of the entire class. There could be only one person in the top spot, so everyone dialed it up a notch, hoping to become #1. Ranking highest was a direct result of your ability to be a better team member than everyone else. If someone was ahead of you, you had to try harder. The other person would then try harder too, hoping to hang on to their position. The result was a bar that was continually being raised by group members.
I’m a fan of stack ranking and publicly displaying the results in group settings. It’s a great way to raise the quality of the group effort, and it gives members feedback that’s hard to ignore.
