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.

Last week, I read a post on X that caught my eye. I shared it with a few folks, which sparked some great dialogue. The post was based on this article. The gist of the post and the article is that the venture capital industry has increasingly focused on coordinating capital across multiple funding rounds for the start-ups it invests in. Therefore, investors focus on fundability—the likelihood they can attract later investors—when making investment decisions. This is a form of consensus seeking. The more capital a company requires from VCs, the more consensus is needed.

For several reasons, it’s harder for smaller VC firms to play and win this game. They need to play a different game if they want to generate alpha (i.e., outsize returns for their investors). Instead of focusing on the fundability of a company, here’s what they should be looking for:

• Companies that are capital efficient and don’t require insane amounts of growth capital to build a great business with a moat. For example, Ho Nam and his firm Altos Ventures invested in Roblox early. He says (see here) that Roblox needed only $10 million total from investors to become cash-flow positive. Roblox has a market cap today, as of this writing, of roughly $50 billion and generated over $1.3 billion in operating cash flow in the last 12 months.
• Companies that don’t need hype or investor consensus to prove they work. With very little capital, they can show in their data that customers demonstrate strong demand for the product because of how well it solves a problem for them.

Interestingly, Ho Nam commented “Agree 100%” below this post.

I’m glad I found this post. It got me thinking about how, going forward, outsize returns can be generated by the smaller funds, especially those that aren’t feeder funds to the big boys.

I tend to still think that founders (and small VC funds that back them) create a lot more optionality for themselves when they focus on providing a good product that customers will pay for (which provides growth capital) instead of on giving the VCs the story they want to invest in. Ironically, if customers love and pay for your product, VCs will love you too. The inverse isn’t always true.  

Last week, I reread Felix Dennis’s book How to Get Rich. Dennis was the founder of Dennis Publishing, Maxim magazine, and Micro Warehouse, a mail-order computer parts company. He was a colorful person who lived an extreme lifestyle, but his thoughts on creating wealth through entrepreneurship were based on his experiences and, in my opinion, spot on.

After reading this book in 2024, I wrote a blog series that captured its main ideas. You can read them:

• Felix Dennis Part 1: Getting Going as a Founder
• Felix Dennis Part 2: Succeeding as a Founder
• Felix Dennis Part 3: Winning and Walking Away

Today I read those posts again, and even after a second reading of the book, I think they capture its essence in a concise way.

His lessons on getting started as a founder got me thinking, especially his advice to find new industries that are growing fast. Lots of people are doing this with AI. His advice to never think small and to act big also resonated with me. He’s right that people stop doing the things that led to their success once they become successful, or they think small and don’t embrace new ideas and ways of doing things.

I’m glad I read this book again. It was a nice refresher.

Side note: I read Dennis’s biography More Lives Than One too. You can learn more about his life journey  here, in the blog post series I wrote based on this biography.

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: 99
• Total blog posts published: 658

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):

• Reread How to Get Rich, a framework for creating wealth through entrepreneurship written by publishing magnate and founder of Maxim magazine Felix Dennis  

What I’ll do next week:

• Read a biography, autobiography, or framework book
• Write a post sharing what I learned from synthesizing The Art of Execution

Asks:

• No ask this week

Week three hundred 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:

• Same as last week: I had trouble getting started on synthesizing another book.

What I learned:

• ·Going back to synthesize a book I’ve read after I’ve begun reading another one is hard. Might make sense to synthesize as I read.

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

The forecast is calling for bad weather to hit most of the country this weekend. An ice storm is expected in Atlanta. I hate feeling trapped, but I’m going to try to use this time to catch up. Specifically, I want to write a post about what I learned from synthesizing The Art of Execution.

Wish me luck!

Today I had a conversation with a friend and entrepreneur about how he works. He described his system, which relies heavily on an AI assistant that he chats with daily. He graciously showed me what he built and how it all works.

I won’t get into all the specifics, but a few things stuck with me:

• MCP – He’s using model context protocol (MCP) to connect all his various tools to Claude’s AI assistant so the assistant has proper context around what’s important to him.
• Database – He stores everything—contacts, goals, etc.—in a Notion database, which Claude accesses via MCP.
• 10 items max – In any given day, Claude gives him no more than 10 action items to focus on getting done.
• Specialization – He built a different AI assistant for each part of his life (work, personal, etc.). Each acts according to specific instructions and accesses the appropriate data in a Notion database.
• Update permissions – He gives Claude update permissions so it can update his calendar, his Notion database, and other systems it has access to.

I was impressed with his setup. He’s leveraging AI to manage various aspects of his life and help him pinpoint what to focus on every day.