Cowboy Values in Modern Business: What Entrepreneurs Can Learn

Howdy y’all, I’m Chip Schweiger, the Cowboy Accountant, and welcome to another edition of Way Out West with The Cowboy Accountant. 

The podcast that takes you on a journey through the stories of the American West, brings you the very best cowboy wisdom, and celebrates the cowboys and cowgirls who are feeding a nation. 

There’s something about the cowboy way of life that tugs at the heartstrings. 

Picture this: an endless horizon bathed in the amber glow of a setting sun, the sound of hooves softly crunching across dry earth, and the smell of leather and campfire smoke drifting through the air. 

Out here, life moves at a different pace, where a man’s word is as steady as the stars above.

It’s in moments like these that the values of the American cowboy come to life—the kind of values that endure long after the dust has settled. 

Grit, 

self-reliance, 

and integrity... they’re more than just words out here. 

They’re a way of living, a creed that has shaped not only the West, but also the foundations of good, honest business. 

So today on the show, we’re going to journey down that very trail—exploring how the timeless values of the cowboy can inspire modern entrepreneurs and business owners like you. 

Because even in a world filled with skyscrapers and smartphones, those lessons from the open plains still hold true.

So, pull up a chair by the fire, settle in, and let’s talk about what cowboys can teach us about leadership, resilience, and staying true to ourselves in the business world.

After the episode check out the show notes at our new website at podcast.CowboyAccountant.com. 

[MUSIC]

Hi there, and welcome back. Today we’re heading down a trail that connects the world of cowboys and the world of business. That’s right, we’re talking about what entrepreneurs, CEOs, and business owners can learn from the grit, self-reliance, and integrity that defined life on the range. 

As you know, I’m not only a cowboy but I’m also an accountant. A CPA with my own public accounting firm. And so this episode is going to touch on both of these aspects. I’ve been thinking about this episode for a while, so I hope you find it interesting, even if you’re not a business owner.

Before we dive in, though, I want to ask you to picture a cowboy for a moment. 

I bet you're imagining someone out in the open plains, tough as nails, working sunup to sundown. 

But here’s the thing: the same values that helped those cowboys survive are the same values that can help entrepreneurs thrive in today’s fast-paced, ever-changing business landscape.

So let’s get to it and talk about how these timeless values—grit, self-reliance, and integrity—apply to modern business.

Let’s start with grit. Now, grit is a word that gets tossed around a lot, but what does it really mean? 

Well, in cowboy terms, grit is about more than just toughness. It’s that deep-down determination to keep pushing forward no matter what’s standing in your way. 

Whether it was surviving a brutal storm on the trail or staring down a herd of stampeding cattle, cowboys didn’t quit. 

They found a way to get the job done.

There’s a story from the old cattle drives that sums this up perfectly I think. 

Cowboys would spend months driving cattle hundreds of miles to market, facing extreme heat, rattlesnakes, and sometimes even hostile encounters. 

But one of the greatest dangers was a cattle stampede. Imagine trying to control thousands of cattle that suddenly spook in the dead of night. 

Cowboys had to ride into the chaos, with the threat of being trampled, just to turn the herd back. That takes serious grit.

Now, how does that apply to business? Well, think of the last time you faced a challenge in your business—whether it was a product failure, a financial shortfall, or a pandemic flipping your entire industry upside down. 

Grit in business is about sticking with it through the tough times, being willing to ride into the storm to steer your team or your company through the chaos. 

It’s about resilience and perseverance, qualities that define every successful entrepreneur.

Take Steve Jobs, for example. Fired from Apple, the company he co-founded, he didn’t just give up. He went on to create new ventures like Pixar, and eventually returned to Apple to lead it into becoming one of the most successful companies in history. 

That’s grit in action—just like those cowboys on the trail, you’ve got to stay in the saddle, even when the going gets rough.

OK Next up, self-reliance. Out on the range, a cowboy couldn’t rely on anyone else to do their job. They had to saddle their own horse, mend their own fences, and often survive on their own wits. Cowboys learned that if they didn’t take responsibility for their own success, no one else was going to do it for them.

There’s a saying: “Always saddle your own horse.” It’s simple, but it’s meaning runs deep. 

It means owning your responsibilities, not passing the buck when things get hard. 

In the business world, this translates to taking ownership of your decisions. Entrepreneurs can’t sit back and wait for someone else to solve their problems. If something needs doing, you have to roll up your sleeves and handle it.

I once heard a story about a startup founder who, when the business was struggling, realized he couldn’t afford to hire additional help. Instead of giving up or looking for shortcuts, he dove into learning everything he could about the different aspects of the business—from marketing to customer service to coding. 

That self-reliance didn’t just help him survive, it helped him understand his business inside and out. And when success finally came, it was because he’d taken full ownership of every challenge along the way.

This cowboy lesson is crucial for entrepreneurs. You might not always have a team to lean on or a safety net. Whether you’re just starting out or running a multi-million-dollar company, the buck stops with you.

Let’s take a quick break and when we come back, I’ll visit with you about my thoughts on integrity, which I view as the core of Trust and Leadership and the finally Cowboy Leadership or what I call Lessons from the Trail. Be right back.

[BREAK]

Welcome back. 

Now, let’s talk about integrity. In the cowboy world, still to this day, your word is your bond. Bank in the 1800’s there were no contracts signed on the back of a horse, no legal teams to hammer out the details. 

Deals were made with a handshake, and a cowboy was only as good as his word. If you promised to do something, you’d better make sure you followed through.

Still to this day, integrity is the bedrock of trust. It’s what makes people want to do business with you. As entrepreneurs, you know that your reputation is everything. 

In today’s world of online reviews and social media, word travels fast. If you’re not honest in your dealings or if you cut corners, people will find out—and once trust is broken, it’s nearly impossible to repair.

One of the most iconic cowboy figures, Charlie Goodnight, understood this well. 

A cattleman and rancher, he was known for his integrity. He didn’t just see cattle as money on the hoof; he saw them as his responsibility. 

He worked hard to keep his word to both his partners and his customers. And that’s why people trusted him with their business, even in tough times.

In modern business, integrity is about more than just honesty. It’s about transparency, fairness, and accountability. 

Entrepreneurs who lead with integrity don’t just build companies, they build legacies. It’s how you inspire trust in your team, your customers, and your investors. You make sure that when you say something, people know you mean it.

So, we’ve talked about grit, self-reliance, and integrity, but how do these values shape leadership? 

Being a cowboy in the 19th century wasn’t just about herding cattle; it was about leading a crew, sometimes across hundreds of miles of rugged, unforgiving terrain. 

The trail boss had to make quick decisions, often in the face of danger, and his crew had to trust his leadership.

One thing I’ve learned both as a cowboy and a business owner is that leadership isn’t about barking orders—it’s about leading by example. 

When a cowboy took on the role of trail boss, he didn’t sit back and relax while the others did the hard work. He was out there in the thick of it, riding alongside his men, showing them that he was willing to do whatever it took to get the job done.

In the same way, modern business leaders need to be in the trenches with their teams. Whether it’s taking on difficult tasks, being transparent in communication, or holding yourself accountable, your team will follow if you lead with conviction and authenticity.

Take a look at some of today’s most successful entrepreneurs. People like Elon Musk or Sara Blakely didn’t just build companies; they led by example. They rolled up their sleeves, worked alongside their teams, and inspired others with their vision and commitment.

At the end of the day, cowboys and entrepreneurs aren’t all that different. Both face challenges, both take risks, and both are driven by values that stand the test of time. Whether you're on the range or in the boardroom, grit, self-reliance, and integrity are the pillars of success.

So, as you saddle up for your next big challenge in business, remember these cowboy values. They’ve been guiding cowboys through the roughest trails for centuries, and they can guide you too.

Well, that about wraps up another edition of Way Out West with the Cowboy Accountant, but before we’ve go we’ve got one more thing.

[BULL SOUND]

Yep, that distinctive call from Buster the Bull means it’s time for the cowboy glossary term of the week. 

And this week’s term is Try. The dictionary describes the word “try” as a verb: “To make an effort to do or accomplish (something); an attempt.” For those of the working ranch, try when used as a noun is expanded to mean an attitude of constant effort. 

Spend even a little bit of time around a working ranch and you’ll hear “There’s a lot of try in that hand” or “He’s got guts and he’s got try.” 

For the rest of us, try is well-described as the blend of grit, guts and heart we need to succeed in progressively tough, competitive times. 

It’s a willingness to keep going when facing insurmountable obstacles. It’s an attitude of never giving up even after experiencing failure upon failure.

So, there ya go. The term try. 

[OUTRO MUSIC]

And with that, that’s all for this week’s show. And I truly appreciate you riding with me. And I hope you enjoyed this episode. I know it’s a bit different that what I normally talk about, but thought it was important. 

If you did enjoy it, please consider please consider subscribing to this podcast so you’ll never miss an episode.

Until next time, mi amigo, we’ll see ya down the road.