Jim Conroy and Boot Barn: What Really Happened to the Cowboy King of Retail

Jim Conroy and Boot Barn: What Really Happened to the Cowboy King of Retail

Jim Conroy left. Honestly, for anyone following the retail world over the last decade, that sentence carries a lot of weight. After twelve years of turning a niche western wear shop into a multi-billion-dollar juggernaut, the man who basically defined the modern Boot Barn era decided to hang up his spurs—or at least trade them for the discount aisles of Ross Stores.

It wasn't a quiet exit. When the news broke in late 2024 that Conroy was stepping down as CEO to take the helm at Ross, Boot Barn’s stock took a 6% tumble almost instantly. Investors were spooked. You can’t really blame them, though. Under Conroy’s watch, the company didn't just grow; it transformed. We're talking about a business that went from roughly 86 stores when he started in 2012 to over 420 by the time he cleared out his desk.

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The Conroy Era: More Than Just Cowboy Boots

Most people look at a place like Boot Barn and see a sea of leather and denim. But Jim Conroy saw a "lifestyle brand." That’s the kind of corporate speak that usually makes people roll their eyes, but he actually made it work. He realized early on that you can't just survive on people who actually own horses. There aren't enough of them.

Instead, he leaned into the "work" side of the business. He brought in more rugged gear—think Carhartt jackets and Timberland PRO boots—to capture the construction and oil field workers. Then he went after the "country lifestyle" crowd. Basically, if you liked country music or just wanted to look like you spent your weekends on a ranch (even if you were actually in a suburban office in Jersey), Conroy had a shelf for you.

One of his biggest moves was the "exclusive brands" strategy. He didn't want to just sell other people's stuff. He built in-house brands like Cody James and Shyanne. These weren't cheap knockoffs either. They were high-margin, high-quality lines that grew from a measly $5 million in sales to over $600 million. That is a massive swing in profitability.

By the Numbers: The Growth Story

It’s easy to get lost in the narrative, but the cold, hard math of the Jim Conroy Boot Barn tenure is pretty staggering.

  • Store Count: Jumped from 86 to 426 during his 12-year run.
  • Annual Revenue: Skyrocketed from $233 million in 2012 to nearly $1.9 billion in fiscal 2025.
  • Expansion: He pushed the brand into 46 states, proving that people in the Northeast and Mid-Atlantic actually do want to buy western boots if you give them a nice enough store to do it in.

The guy was a machine when it came to site selection. He figured out that a Boot Barn in a "non-traditional" market like Pennsylvania could actually perform as well as one in Texas.

Why the Jump to Ross Stores?

So, why leave a good thing? In late 2024, Ross Stores announced Conroy would become their CEO-elect, officially taking the top spot in February 2025. He’s replacing Barbara Rentler, a retail legend who had been with Ross for nearly 40 years.

It’s a different beast. Ross is an off-price giant with over 2,000 stores and $20 billion in revenue. It's much bigger than Boot Barn, but the core challenge is similar: how do you keep growing a massive retail footprint while keeping margins tight and customers happy?

Ross is paying him well for the move, too. We're talking a $7.6 million sign-on bonus and a restricted stock award valued at around $32 million. If you're going to leave the house you built, that’s a pretty decent way to do it.

The "After" at Boot Barn: Is the Magic Gone?

When Conroy walked out the door on November 22, 2024, he didn't leave the cupboards bare. He left a very specific playbook. The board tapped John Hazen, the Chief Digital Officer, as the interim CEO before eventually making him the permanent leader in May 2025.

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Hazen was the guy behind the scenes driving the e-commerce growth. While Conroy was building physical stores, Hazen was making sure the website actually worked and that the "omnichannel" experience (another fancy word for buying online and returning in-store) was seamless.

The strategy hasn't changed. Boot Barn is still aiming for 900 stores. They’re still pushing their exclusive brands. They’re still betting big on the idea that the "western" aesthetic is a permanent part of American fashion, not just a passing trend fueled by shows like Yellowstone.

Common Misconceptions About the Transition

A lot of people think Boot Barn is "struggling" because the stock dipped when Conroy left. That’s not really the case. The dip was more about the uncertainty of losing a proven leader than any actual problem with the business. In fact, right before he left, the company reported a 13.7% increase in net sales for the quarter.

Another myth is that Conroy "sold out." In reality, twelve years is an eternity for a CEO. Most retail execs last about five. He took the company through an IPO in 2014, navigated the pandemic, and built a dominant market leader. Moving to Ross is just the next level of the game for him.

What This Means for the Future of Western Retail

The Jim Conroy Boot Barn legacy is basically a blueprint for how to scale a niche business. He proved that "western" isn't a tiny slice of the pie; it's a massive, multi-category industry.

If you're looking for actionable takeaways from the Conroy era, here’s what sticks:

1. Don't be afraid to broaden your base. Conroy didn't just sell to cowboys. He sold to blue-collar workers, suburban fashionistas, and country music fans. He expanded the "addressable market" without losing the core identity of the brand.

2. Own your inventory. By building exclusive brands, Boot Barn stopped being a middleman for other companies and started capturing the full profit margin of every sale. This is why their earnings stayed so healthy even when inflation was hitting other retailers.

3. Physical stores still matter. In an era where everyone says brick-and-mortar is dead, Conroy opened hundreds of stores. But he made them "destinations." They are clean, well-lit, and stocked with an massive variety of inventory that's hard to replicate online.

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4. Leadership succession is key. The reason Boot Barn didn't implode when he left is that the team he built—people like John Hazen—had been there for years. They knew the plan because they helped write it.

For investors or retail fans, the next year will be interesting. We’ll see if Conroy can apply that same growth magic to Ross, and we'll see if Boot Barn can maintain its momentum without its long-time architect. So far, the foundation looks pretty solid.

If you're tracking the company now, keep an eye on the new store performance in the Northeast. If those stores keep hitting their $3.5 million revenue targets, the 900-store goal isn't just a dream—it's an inevitability.