The Wealthy Cowboy

September 26, 2026

A year ago, I would have laughed if you told me I would be sitting behind a microphone and in front of a camera as a guest on The Wealthy Cowboy Show. For starters, I am not entirely sure I qualify as either wealthy or a cowboy.

That thought was probably the thing rattling around in my head most as I drove to the studio this week. I have owned Halcyon Ranch for a little over a year. I have cattle, horses, pastures, equipment, fences that always seem to need something, and a growing list of lessons learned the hard way. But put me in a room with someone who has spent forty years raising cattle, and I know which one of us should be doing most of the listening.

On the other hand, I have spent nearly 30 years in business and leadership. I have been a teacher and principal, led technology in a school district, helped build businesses at companies like CDW and Amazon, worked in startups, managed teams, carried a P&L, led growth organizations, and been a CEO. Those are spurs I have earned. And maybe that was what made this particular invitation so interesting.

Before the Microphone

When Ambrook invited me to appear on The Wealthy Cowboy Show, my first reaction was excitement. My second was probably some version of, “Why in the hell would they want me?”

I have listened to enough of Crockett’s interviews to know that some of his guests have spent their entire lives in agriculture. They run enormous cattle operations. They understand livestock and land at a level I may never reach. I am a guy who bought a ranch in his fifties and is still learning every day. I didn’t want to walk into that studio pretending otherwise.

What I did feel like I had earned was the right to talk about the experiment happening at Halcyon. From the beginning, I have wondered whether some of the principles I have spent my career using to grow organizations could be applied to a ranch. Can you start small, establish a baseline, understand the economics, test assumptions, measure results, and then use what you learn to decide where to invest next?

That is essentially what I have been doing.

I started with a goal of five head of cattle, not fifty. I invested in the bunkhouse and know what it cost, what it produces in rent, and roughly how long it takes to pay back the investment. I am building horse boarding as another revenue stream. I track expenses across the different parts of the operation because I want to know what is actually working, not just what feels like it is working.

None of that makes me an expert ranch owner. But if I understand the economics of five cattle, maybe I earn the right to try ten or twenty. If one revenue stream works, maybe I invest more there. If something doesn’t work, I would much rather learn that while the experiment is small.

There is an old business saying that what gets measured gets done. I think there is another piece to it. What gets measured gives you the confidence to decide what to do next. That was what I hoped I could contribute to the conversation.

Then Something Interesting Happened

The show started a little late, which turned out to be a gift. Crockett and I sat around talking before we ever started recording, and pretty quickly it stopped feeling like I was waiting to be interviewed. We were just talking.

Then the microphones and cameras came on, and the conversation went somewhere I wasn’t expecting. Crockett wanted to talk about leadership.

He asked some really specific questions about things I have experienced during my career. We spent considerably more time talking about education and education technology than I expected. He was interested in what schools looked like during different periods of my career, how organizations change, and what I had learned leading people through those changes.

Suddenly, I wasn’t the new rancher trying to keep up on a cowboy podcast. We were talking about things I have spent most of my adult life thinking about.

That opened the door to something else I’ve been thinking about quite a bit lately: the parallels between EdTech and AgTech.

Technology doesn’t become valuable simply because it exists. It has to solve a real problem for a real person. You have to understand the customer, earn trust, prove value, know your numbers, and ultimately make someone’s life or business better. Whether that person is running a school district or running cattle, I’m finding that some of the foundational principles aren’t all that different.

Curiosity Works Both Ways

At some point, Crockett told me something I found fascinating. Some of the show’s most popular episodes are conversations with big cattle ranchers. But some of the conversations he personally enjoys most are the ones where he gets to learn about business, investing, startups, and companies. I laughed because in a funny way, we were almost opposites.

He grew up around livestock. Cattle and agriculture are familiar territory to him, while he is curious about the world I have spent my career in. I have spent three decades around education, technology, leadership, and business, while I can’t seem to learn enough about cattle, horses, land, and agriculture.

I think that is part of why the conversation became so comfortable. Neither of us needed to pretend to know everything. We could bring what we knew to the table and be curious about what the other person knew.

There might be a leadership lesson in that by itself. Too often, experience becomes something we defend rather than something we exchange. We enter conversations wanting to demonstrate what we know instead of discovering what somebody else knows. Some of the best conversations I’ve had are with people who are confident enough in their own experience to still be genuinely curious about someone else’s.

The Customer’s Chair

There was another interesting part of the experience for me. Ambrook sponsored the episode and helped make the connection, which meant that for once I was sitting in the customer’s chair.

I have spent years on the other side of this equation. I have recruited customers for panels, coached them before interviews, built customer stories, and worked with advocates who could tell a company’s story far more credibly than the company ever could.

There is always a temptation in those situations to make the product the story. That almost never works because nobody wants to listen to a thirty-minute commercial disguised as a conversation.

The best customer stories are actually about the customer. The company or product belongs in the story because it helped them accomplish something, but it shouldn’t become the main character.

I thought Ambrook and Crockett handled that really well. We talked about Ambrook several times, and Crockett made sure there were opportunities to explain how I use it. But Ambrook wasn’t the story. Halcyon was the story.

More specifically, the story was about trying to build something and understanding that if you want it to grow, you need to know your numbers. You need a baseline. You need to understand where money is being made and where it is being spent. You need enough information to make the next decision intelligently.

Ambrook happens to be one of the tools helping me do that. That’s a much better story than a commercial.

The Other Side of the Spurs

Last Saturday, I wrote Earn Your Spurs about the strange place experience occupies in leadership. After enough years, you have earned the right to trust some of your instincts, but you haven’t earned the right to stop questioning them.

When I wrote it, I knew this week was going to put me on the other side of that lesson.

I was about to walk into The Wealthy Cowboy Show very conscious of the spurs I haven’t earned. I wasn’t going to sit behind a microphone and in front of a camera pretending to be a lifelong rancher or cattleman. I’ve been doing this for a little over a year. There are people all around me who have forgotten more about cattle, horses, and agriculture than I currently know.

But something became clearer to me during the conversation. I don’t need to apologize for the spurs I have earned either. Thirty years of business and leadership experience doesn’t disappear when I walk through the ranch gate. Some of those lessons transfer. Some don’t. Figuring out which is which might be one of the most interesting parts of this entire chapter of my life.

That was essentially what happened during the interview. Crockett didn’t need me to teach him about cattle. He grew up around them. I certainly didn’t need to pretend that I could. Instead, his curiosity about business and leadership met my curiosity about agriculture, and we found a whole lot of interesting ground in between.

Maybe that’s the larger lesson I’m taking away from the experience. Earning your spurs doesn’t mean you eventually become the expert in every room. It means knowing which spurs you’ve earned, which ones you haven’t, and being comfortable enough with both to keep learning.

You don’t have to have everything figured out before you start. Bring what you know. Acknowledge what you don’t. Find people who know things you don’t. Stay curious enough to learn from them, and then pay attention to what happens.

If it works, maybe you’ve earned the right to take the next step.

And if you’re lucky, every once in a while the process puts you behind a microphone and in front of a camera with someone you probably never would have met otherwise. You exchange a few ideas, learn something from each other, and expand the circle of people you can call the next time you encounter something you don’t understand.

For me, that’s already a pretty good return on the investment. And I’m still not calling myself a cowboy.