How Cowboy Kent Rollins Went From ‘Poor As Dirt’ to a YouTube Star With 3.5 Million Fans
Chef, cookbook author and entrepreneur Cowboy Kent Rollins rustled up big success by staying true to his beliefs and passion.
On this week’s episode of How Success Happens, I sat down with Cowboy Kent Rollins, a real‑deal Oklahoma cowboy who turned his small business of feeding ranch hands out of a chuck wagon into a hit YouTube channel, bestselling cookbooks, a TV show, and a booming product line. Kent isn’t just a cook; he’s a storyteller, a brand builder, and proof that authenticity still wins in a highly polished, fake reality TV world.
Watch our full conversation in the video above or listen here, and read on to get his best insights to help your personal success giddy-up in three, two, one!
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Three Key Insights
- Challenge Yourself or Nothing Will Change
Kent admits he “made a D in high school in speech” and hated getting up in front of people, but after his dad passed away, he realized “sometimes you have to step outta your comfort zone.” That leap took him from ranch cook to national TV, including Food Network’s Chopped Grill Masters and ultimately beating Bobby Flay in a steak showdown. He told me, “If it doesn’t challenge you, it will never change you in life,” and that mindset helped him embrace cameras, crowds, and massive opportunity instead of hiding behind the stove.
Takeaway: Identify one thing that scares you in your business this week—and do it anyway, treating fear as proof that growth is waiting on the other side.
- Authenticity Is King
As TV producers came calling, Kent kept turning them down because “you’re too much reality and we’re too much real,” insisting that “people can spot a counterfeit a hundred miles away.” Instead, he and his wife Shannon built their own show on YouTube so they could stay in control of the content, pray on camera, say “God bless America,” and keep things “true and real and authentic.” He says growing their channel involved a strategy learned out in the fields. “If you’re gonna do a YouTube video and you want to be a success…be consistent, just like feeding them cows.” They released a video the same time every week, so fans knew he’d show up. And the feeding technique paid off with 3.5 million subscribers and a global fan base that “feels like family.”
Takeaway: Build your platform where you can stay true to yourself, then show up at the same time, every time, until your audience learns they can count on you.
- Cook What You Love for the Ones You Love
Kent traces everything back to his mom and a crowded kitchen in southwest Oklahoma, where “we were poor as dirt, but mama made sure we eat pretty good.” He says his childhood taught him that “the kitchen was not just a place to cook” but also a place to solve life’s problems around the table. “It’s not the legs of the table that hold it up, it is the family that has gathered around it,” he recalls her saying. Kent’s mom encouraged him to “cook what you love for the ones you love and cook because you enjoy it.” That philosophy shows up in how he tests recipes—if cowboys come back for seconds and thirds, “you better write that recipe down.” To this day he and Shannon insist on writing, shooting, and storytelling themselves so their products and content remain “totally us.” The result is a business that feels less like a place to buy “merch” and more like an invitation to pull up a chair at their fire.
Takeaway: Build offers around what you genuinely love and who you genuinely care about, then watch how much easier it becomes to create, sell, and show up consistently.
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Two Great Ways to Learn More
- You can keep up with Cowboy Kent and Shannon on their YouTube channel, and check out their pans, cookbooks, recipes and episodes of their cast‑iron‑heavy TV show The Cast Iron Cowboy at kentrollins.com.
- Read this story about the power of authentic storytelling to build your brand’s identity.
One Question to Ponder
Kent said, “Don’t read the story, be what the story’s about.” What is one concrete step you can take this month to make yourself the main character in an awesome entrepreneurial origin journey?
Email your answer to howsuccesshappens@entrepreneur.com — your response may be read on a future episode.
About How Success Happens
Each episode of How Success Happens shares the inspiring, entertaining, and unexpected journeys that influential leaders in business, the arts, and sports traveled on their way to becoming household names. It’s a reminder that behind every big-time career, there is a person who persisted in the face of self-doubt, failure, and anything else that got thrown in their way
On this week’s episode of How Success Happens, I sat down with Cowboy Kent Rollins, a real‑deal Oklahoma cowboy who turned his small business of feeding ranch hands out of a chuck wagon into a hit YouTube channel, bestselling cookbooks, a TV show, and a booming product line. Kent isn’t just a cook; he’s a storyteller, a brand builder, and proof that authenticity still wins in a highly polished, fake reality TV world.
Watch our full conversation in the video above or listen here, and read on to get his best insights to help your personal success giddy-up in three, two, one!
