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.

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.

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.

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.

Last week, I shared (see here) that I was curious about how entrepreneurs learn to work. My thesis is that many don’t know how to work, and the ones who do are self-taught out of necessity. In the last few days, I’ve talked to a few entrepreneurs and asked these point-blank questions:

• How do you decide what to work on each day?
• What did your last workday look like?
• What did your last workweek look like?  
• How did you learn how to work as a founder?

The first three questions are to understand how they work. The last question is the most important one.

I’ve done only a handful of these sessions, but so far, the answer is that they learned over time by piecing together what people shared with them. Also, the forcing function was stress and anxiety, which made them realize that how they were working was a big problem.

It’s early days, and I’m curious. I’ll have more of these conversations with entrepreneurs. This might be an overlooked problem that many entrepreneurs face.

Yesterday I shared (see here) that a friend who is an entrepreneur learned how to work—meaning how to work efficiently and consistently to meet goals—while employed by a large corporation known for its world-class training. That’s more the exception than the norm, in my opinion. Most people don’t get world-class training on how to work. That got me thinking about myself—how did I learn how to work?

Thinking back, this isn’t something I was ever taught. Not in college and not in corporate America. After I became an entrepreneur, I felt like I was drowning in a never-ending to-do list. I was stressed out. That pain helped me realize that how I was working wasn’t sustainable or effective. So, I sought out other entrepreneurs and asked them how they worked. Over time, I pieced together a system that worked to some extent. But it wasn’t until years later that I read books on the topic that helped me understand what a methodical approach to work looks like and how to implement one.

Now I’m curious. How do most entrepreneurs learn how to work? I don’t know the answer, so I’m going to ask a few and see. My gut tells me that many don’t know how to work and are stressed out—and that those who do know are self-taught out of necessity. Let’s see if I’m right.  

This week, I caught up with a friend who’s an entrepreneur. During our chat, I inquired about how he works. How does he determine what he’s working on each day? How does he know what needs to be done for each objective or project he’s working on? You get the idea. He said that he learned how to work—meaning he learned the process of working efficiently and consistently—while employed by a large corporation known for its world-class training. But that was a few decades into his career.

What I took away from this conversation is that most people are never taught how to work. They’re taught skills, and they gain expertise. But they’re never taught how to effectively execute their skills from day to day to accomplish goals or objectives. Instead, they try to remember and manage everything in their head and end up stressed or burnt out as their responsibilities at work and home increase.

To take this a step further, entrepreneurs experience many times more pain than the average person because of not knowing how to work. They often start out by doing literally everything in the business—much of which they have zero skills or experience in. Over time, many of them experience high levels of stress and anxiety because of this, which causes other problems.

My big takeaway is that the costs of never being taught how to work are high, especially for entrepreneurs.

Yesterday, I shared an interview featuring Howard Marks and his four steps to dealing with change (see here). Toward the end of the interview, Marks talked about his partnership with one of his Oaktree Capital cofounders, Bruce Karsh. He described partnership as an important part of a healthy work environment, which he has with Karsh and other Oaktree Capital founders.

So what’s the key to healthy partnership? Marks has a simple framework. Here’s the key to a healthy partnership (in all aspects of life):

• Shared values – You have to believe the same things about how you want to operate in the world. Marks gave the example that he and Karsh shared the view that they should invest by seeking moderate gains and avoiding losses. Said differently, they would aim for consistent returns rather than grand slams. Neither believed in shooting for the stars. Their values regarding their investment strategy were the same.
• Complementary skills – The key to success is having a well-rounded team that covers all the important areas—the team is strong in all key areas although each individual is not. If you have a team of really smart people who all specialize in the same thing, the team has a skill set hole that will likely cause execution and other issues. A better approach is to work with people who are strong where you’re weak, so you complement each other. This enhances the team’s ability to execute, and people won’t be stepping on each other’s toes.

I agree with Marks. I think partnerships that have both these things can do well. My gut tells me that many people understand the second point and seek complementary skills—opposites attract. But I don’t think as many people understand how important shared values are in a partnership. If you have complementary skill sets but polar-opposite views on how to go about things, you’re bound to have a day of reckoning and maybe even a huge blowup between partners.

If you’re interested in Mark’s full thoughts on partnership, take a listen here.

This week, I was catching up with an entrepreneur. It’s the end of the year, so I asked how 2025 has been for them. It’s been hard, they said. They feel like they’ve been getting beaten up all year and that nothing has gone their way. They survived the year but aren’t excited about what the future holds.

As they talked, it became apparent that they’ve navigated very painful situations in their business this year. While this entrepreneur was a bit pessimistic, I was more optimistic for them. Why? I think that pain is a necessary component of growth. Very rarely do people who achieve outsize success do so without first experiencing a period of what feels like extreme pain.

Why can pain be a good thing? Because what you learn from painful experiences becomes critical to helping you successfully navigate future situations. You learn lessons and gain wisdom that improve your decision-making. Better decision-making leads to more rewarding situations and more wins.

I think Ray Dalio put it best in his book Principles when he said this:

Pain + Reflection = Progress

I’m excited for this entrepreneur. I hope they take the time to reflect on the pain they’ve experienced so they can set themselves up to make serious progress in their business in 2026.