This week I caught up with a friend, an entrepreneur who sold his company and has advised founders for over a decade. He pointed out something that differentiates entrepreneurs from others. Entrepreneurs get excited by the potential of an idea and how big the end result could be. That’s enough to get them started. They’re totally focused on the end and the one next thing they can do to move forward. That’s it. That’s all they need to press go.

When they talk with non-entrepreneurs, they can become frustrated because many non-entrepreneurs focus on something different. Non-entrepreneurs can’t wrap their head around the end result because the path to it is unclear or has imperfections. They want to labor over details, achieve clarity, and resolve imperfections before they even think about starting down the path or think about how big the idea could be. The entrepreneurs feel like they’re being dragged into the details and asked questions they can’t answer and that don’t matter yet. They want to talk about the big, high-level opportunity, but they’re being beaten up over the small details of the plan. It’s annoying.

I agree with my friend. I’ve been in this situation many times. Someone asks me detailed questions about something I want to do, and I get frustrated because I don’t think the things they’re asking me matter yet. They’ll be figured out in due course.

A lot of the disconnect is in how entrepreneurs approach getting things done. They’re problem solvers by nature and often must do things they haven’t done before. The way they do that is by focusing on their next action, not all the actions or steps they’ll need to take. They know that with every step they take, they’ll learn something (good or bad) that will help them figure out what the next step should be. Then they’ll act again. This continual process of acting, learning, and acting is essentially an iterative approach to reaching the result they want without starting with a clear path or plan.

When entrepreneurs are asked to provide a detailed plan or path, they become frustrated because they know it isn’t necessary. Things aren’t likely to go as planned, even if there is a plan. Solutions to problems will reveal themselves along the way. The best way to reach a big goal is to get started on it and figure things out along the way.

I’m still curious about the United States from 1968 to 1982. It was a crazy period that saw inflation peak of about 12%, the federal funds rate reaching almost 20%, and the stock market performing poorly. One thing I want to understand more deeply is the reasons underlying the stock market’s performance. Increasing interest rates push down company multiples and valuations, so that makes sense to me. But I think there’s more to know.

I was listening to a podcast when the guest mentioned that Warren Buffett wrote an article in Fortune magazine in May 1977 that explained how inflation robs equity investors. They spoke very highly of the article and explained part of it, which piqued my interest. So, I’m going to find that article and give it a read. Hopefully, I’ll grasp what Buffett was saying and can share my understanding.

‍

I’ve been thinking about new projects, ideas, and things to work on. I looked at what I’ve done in the past and sought themes or patterns. I think there are three high-level buckets that capture everything I’ve done (and want to do going forward):

• Building – Creating new things. It could be starting new companies or just doing fun personal projects. I like building things that interest me. Even if they’re not commercially viable (or successful), I enjoy the process because I learn a ton along the way. This category includes helping or supporting entrepreneurs who have a vision for what they want to build.
• Investing – Investing, for me so far, means investing in other companies—most enjoyably, early-stage start-ups and publicly traded companies. The process of digging into a company, its market, and the people running it is fun, and I always learn a lot from that analysis. Change is constant, so there’s always something to learn (you never master it), which I love too.
• Learning in public – Sharing online what I’ve learned (or what I’m trying to learn) has accelerated my learning, expanded my curiosity, and, hopefully, helped others along the way. Many times, I thought I understood something until I sat down to write a post or record an audio pod about it. The act of explaining something to other people exposes gaps in my understanding and crystallizes my thinking. Learning in public has also been a great way to stimulate my mind and exercise my brain.

Building companies, investing in companies, and learning about people who build or invest in companies. The common thread is entrepreneurship. That’s it. Those are my interests in a nutshell. If something falls into one of those buckets, I’ll likely be interested in it.

This week I had the opportunity to participate in my first book club. For context, this book club was virtual and academically oriented. A few initial thoughts:

• Over 250 people attended, which shocked me. I didn’t have any expectations, but I hadn’t considered that such a crowd would take part.
• The virtual nature of this club allows it to cast a wide net. There were people from other countries, including Canada. The internet removes boundaries—this group could find people anywhere.
• The author of the book was part of the session and shared his thoughts, which I enjoyed. It’s always nice to hear authors’ deeper thoughts.
• This meeting was styled as something of a debate. It began with people arguing for and against the argument in the book. The author then responded to points against the book.
• Many of the arguments presented were prepared statements.

Overall, I enjoyed my first book club experience. The scale and reach of this club were much greater than I could ever have imagined. That definitely stuck with me and has me thinking much bigger about the possibilities of book clubs.

Recently, I caught up with the founder of a high-growth company. The company exploded in growth over the last few years, and now they’re planning for the next twelve months. The founder mentioned that one of his focus areas is maturing the organization. He wants to add more process and structure so they can continue to scale rapidly without the wheels falling off.

When growth is crazy, you normally see a lot of hiring. Things are happening so fast that no one has time to delve into problems or the things holding them back, so they throw bodies at them and hope the smart people they hire will figure it out. The result is continued growth but a lack of process and structure.

When the leaders start planning for continued growth over the next few years, they realize they can’t get there by doing what they’ve been doing. They want more visibility into what’s happening operationally below them, more operational consistency, and assurance that their operations can scale as the company continues to grow.

It’s a cycle I’ve seen before: growth, efficiency, and then more growth. I like to think of it as the company catching up to the expectations implied by its revenue growth. For high-growth companies, it’s part of their normal cycle.

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: 100
• Total blog posts published: 665

This week’s metrics:

• Books read: 1
• Blog posts published: 7

What I completed in the week ending 1/25/26 (link to the previous week’s commitments):

• Read Take the Measure of the Man, the memoir of Comcast Corporation cofounder Daniel Aaron  

What I’ll do next week:

• Read a biography, autobiography, or framework book

Asks:

• No ask this week

Week three hundred five 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:

• Same as last week (and the week before): I had trouble getting started on synthesizing another book.

What I learned:

• I listened to this section of an Odds on Open Podcast episode where Alix Pasquet argued that reading books leads to more critical thinking, unique insights, knowledge building, and gaining of analytical reps, whereas using technology like AI doesn’t. AI just helps you acquire information, which is different than knowledge. Because younger people aren’t reading books, Pasquet thinks they’re at a disadvantage. Pasquet also shared and discussed extensively this quote from Henry Kissinger:

Reading books requires you to form concepts, to train your mind to relationships. . . . A book is a large intellectual construction; you can’t hold it all in mind easily or at once. You have to struggle mentally to internalize it. Now there is no need to internalize because each fact can instantly be called up again on the computer. There is no context, no motive. Information is not knowledge. People are not readers but researchers, they float on the surface. . . . This new thinking erases context. It disaggregates everything. All this makes strategic thinking about world order nearly impossible to achieve.

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

This week I spoke independently with two early-stage entrepreneurs who were trying to figure out problems their respective businesses were facing. During our conversations, I realized they didn’t understand the real problem. They just knew they had a problem and wanted to solve it, but they couldn’t articulate it or tell me the root cause. This made it harder for me to help them as I wasn’t sure what I was helping them with and don’t have enough context because I’m not in either business day-to-day.

Both experiences made me think of Kidlin’s Law, a simple but powerful law:

If you write a problem down clearly, then the problem is half solved.

A powerful aspect of this simple law that many overlook is its writing component. It doesn’t say figure things out in your head or describe the problem out loud. It says you should write the problem down. You don’t have to think clearly to sound good when speaking, but writing demands clarity. When you speak, your brain can gloss over unclear steps and still produce a convincing narrative. Writing exposes those gaps. Writing a problem down forces you to evaluate each step of your thinking and understand the problem deeply. It also forces you to figure out the best way to communicate the problem clearly (and preferably concisely) to others. Once you’ve written it down in a way that others can understand, you’ve cemented your understanding of the problem in your brain and made it easier for you to speak coherently about the problem, with extreme confidence, to people who can help you. It should also make it easier for you to articulate precisely how they can help you, which increases the probability that they will help you (if people have to figure out how to help you, they usually don’t bother).

I’m a fan of Kidlin’s Law. It’s something simple that anyone can do, but most people won’t. For those who do, it improves the chances that they’ll solve whatever problem they’re facing.

Today, I had the privilege of participating in a conversation about how to add value to founders in the Atlanta ecosystem. There were suggestions to create educational tracks that address common problems founders face, such as fundraising. All of them were valid and would add value. But they wouldn’t resonate with all entrepreneurs—only those who are experiencing a problem related to that track.

When I think about what resonates universally with founders, two things come to mind:

• Peer community – Entrepreneurship is lonely. Entrepreneurs want to be around other entrepreneurs who are going through the same things—people who can relate to the struggle. And if they’re ambitious and trying to build a company that can grow fast, they want to be around others who are trying to do the same. I once read “Iron sharpens iron, so one man sharpens another.” Founders want to be around other entrepreneurs they can compete with—entrepreneurs who’ll sharpen them.
• Peer accountability – Execution is what matters most in entrepreneurship. Founders want to get stuff done, but they’re human. Sometimes they need a friendly nudge. Sometimes they need to be held accountable by peers they respect, don’t want to let down, and compete with (in a friendly manner).

When I thought about how to present these ideas as a value proposition that would quickly resonate with entrepreneurs in the Atlanta ecosystem, or any ecosystem for that matter, I came up with this:

• Community for high-growth founders
• Facilitated accountability groups of peers at similar stages

Offer those two opportunities to entrepreneurs, and I’d bet most would jump at the chance to be part of something like that, even if they don’t know all the specifics of how it works.

Today brought a good thought exercise. I’m glad I was a part of it because it got me thinking about what value prop would resonate with ambitious entrepreneurs. I think the above would be something entrepreneurs would instantly get and want to be part of.

For the past few years, many people have been talking about diversifying their cash flow. They usually land on the idea of buying a small business that can shoot off cash to them—specifically, buying a mom-and-pop business from someone looking to retire. Buying from a retiring entrepreneur is attractive because revenue can probably be increased by upgrading the business through technology and process improvements. The business’s value increases (assuming multiples stay flat or rise), and its rising revenue translates into higher cash flow (i.e., a higher yield on investment).

This all makes sense, and I generally like how this plan sounds. As time has passed, though, I’ve noticed two hurdles for friends turning this plan into reality.

The first challenge is sourcing. This is true of all investing. How do you find the best opportunities that will generate the highest return—especially when you’re going after tiny companies that don’t publish financial information about their business performance? To properly source good deals that others aren’t aware of, you likely need a great network that’s tapped into baby boomer entrepreneurial circles, and you need to work it aggressively. Or, you could just brute-force it and start cold-calling businesses. Either strategy requires a ton of time and energy.

The second challenge is operational. Entrepreneurs are usually the glue that holds small businesses together (especially those with annual revenue under $1 million). There isn’t enough money to support hiring a staff and becoming an absentee owner. So, once the owner sells and retires, the new owner will have to step in to hold things together and implement improvements to grow the business. Again, lots of time and energy is needed.

After seeing these two hurdles (and others) stop friends, I began wondering if there’s an alternative way to solve the problem, ideally more passively. Could you diversify your personal cash flow by buying a stream of income generated by a business and benefit from some upside potential? Can you do this in a more passive way that doesn’t require as much time and energy but gives you above-average returns (assuming a risk level similar to that of buying a business)?

I think I found an alternative solution. I’ll share my thoughts on it in another post.