People of Yellowstone Country: The Wickens

Meet Jason and Jackie Wickens

Jason and Jackie Wickens are the definition of a Montana Power Couple. Self-proclaimed serial entrepreneurs, the Wickens have been partners, in every sense of the word, since 2007. 

Jackie, a reputable real estate broker with a notable background in construction, is a proud co-owner of Yellowstone Brokers and, alongside her husband, runs their family business Live from the Divide. Jason, a western-style Renaissance man with a passion for music, also works hand-in-hand with his brothers and their direct-to-consumer beef business: Wickens Ranch. However, their success was no easy feat, and their journey to where they are today can be largely credited to their down-to-earth personalities and ambitious approach to life. Their openness and warmth make you want to cozy up with another cup of Joe, and immerse yourself in their wildly entertaining stories.

A proud, 4th-generation Montanan, Jason grew up on his family’s ranch near Winifred. With a childhood love for music and songwriting, he pursued his dreams as a young adult and left for school at the Conservatory of Recording Arts and Sciences in Tempe, Arizona. Like many a cowboy, Jason thinks of himself as a “bit of a gypsy,” and bounced around from job to job traveling throughout the US. Meanwhile Jackie, a competitive snowboarder, fell in love with Bozeman upon her first visit in 2001, and decided to attend school at Montana State University. Her warm smile grows wide as she reminisces, “Yep, this is my place. I’ve never felt so free.” Only a handful of years later, Jackie met Jason, who had made his way back to Montana, and won over Jackie while leaning up against a jukebox at The Eagles Bar in Bozeman. The couple has now laid down roots outside of Bozeman, Montana, in Bear Canyon, where they raise their children and run multiple businesses.

Live From The Divide

Live From The Divide in Bozeman, Montana, resides in a century-old brick-and-wood building near the historic rail yard. With an intimate capacity of 50, the venue curates an authentic American Roots music experience, where artists connect intimately with the audience in a space that transcends the conventional concert setting. Jason and Jackie founded Live From The Divide in 2009 as a traditional recording studio, eagerly booking singer-songwriters to perform for the local community. Over the past decade, the venue has defined itself as a premier live music destination, bringing a theater-like experience to its guests with a central focus on artistry and performance.

“Jackie and I are real nerdy when it comes to songwriters. We’re just fans, so we started inviting people to play. We’ve had the honor of hosting a lot of our heroes and a lot of folks that are well-known today in the Americana genre,” Jason says. The Wickens joke that maybe they were “too ahead of the curve.” “About 10 years ahead of the curve. I would’ve taken five,” Jason says with a laugh. Since those early days when Jason and Jackie had to practically “beg” their friends to help fill the room, many of the venue’s singer-songwriters have gained significant popularity, including artists like Grammy-winner Sturgill Simpson, Tyler Childers, Paul Cauthen, and Billy Strings. Jason credits their sponsors for keeping them going from the beginning. “After doing it for over a decade, there are just so many stories, and it’s rare to go out and not meet someone who says ‘hey’ and tells us their experience with Live from the Divide. It feels like a community. It’s hard because of how much change has happened recently, but we’re still a community. It’s still a small town. We’re still connected.”

Yellowstone Brokers

Jackie’s career in real estate began in 2013, and the couple reflects on it "keeping [them] afloat while Live from the Divide continued to grow." It wasn’t until Jackie met her now-business partner Trecie Wheat Hughes that she felt as though she really started to carve out her place in the real estate world. Together, Jackie and Trecie opened their own brokerage, Yellowstone Brokers. The pair also starred in an HGTV show called “Mountain Mamas,” which provided momentum for the agency.

“My favorite saying is ‘There’s an ass for every saddle.’ And there is. When you’re able to put yourself out there and show people who you are, you attract clients who really align with you,” expresses Jackie. “People want to move out this way for the quintessential Montana lifestyle,” and Jackie is happy to act as a guide in helping people navigate Montana. “If having a home is a goal, helping people accomplish that dream and finding that space that can be their haven away from the craziness that can be the world—that is really rewarding to me.”

Wickens Ranch

Although Jason was raised on the family ranch, he knew from an early age that he would pursue a career in music. However, in 2020, during a time when much of the world was shutting down, a lightbulb went off for Jason. During a drive, Jason turned to Jackie in the passenger side of their truck and said, “I think I’m going to call my brothers and find out if they want to start a direct-to-consumer beef business.” Jackie was hesitant at first to dive into another business, but knew there was no stopping Jason once the idea began to take shape. This conversation was the birth of the D2C side of Wickens Ranch.

Since Jason had long admired the regenerative practices of his brothers, he felt it was important to highlight the quality of the beef and sustainability that the ranch was committed to honoring. He also made it part of his mission to successfully market to consumers the level of care and dedication that went into their beef. Although getting the word out took some time, Jason now finds humor in going from the “music guy” to the “beef guy,” and knows that using his voice in the community helped aid in the success of the business.


It’s no secret that Montana is growing, and it would be easy to attribute the success of the Wickens' businesses to luck. Jackie even calls it “big fish, small pond luck.” However, their success can be more accurately attributed to good, old-fashioned, perseverance and hard work. “We legitimately starved it out for a decade—it was hard to live here. I was glad I experienced those years. It was brutal. I’m grateful also for the people coming in and bringing industry and bringing in growth, because that’s why we can also survive,” Jackie reflects. She is, of course, speaking on those recession years and the years that followed—the early years in Jackie’s career, prior to the tourism boom incited by COVID and the popularity of the Yellowstone television show. 

“There was a big turnover after the first recession where a lot of people had left. But a lot of them started to trickle back in after things got better. I think Montana, once it’s in your soul, it calls you back,” Jackie adds. It is with this perspective that Jackie and Jason are able to view growth and the changing landscape of Montana in the most positive light. “If you want innovation and growth, you have to be part of the conversation. All of that happens with your voice. Decide to be active participants in how you would like to see your community grow. It takes all the different perspectives to be heard and move everything forward. Us as small business owners, we have more impact than we know. Growth is going to happen. If you feel compelled one way or the other, then get involved,” urges Jason.


While discussing their love for Montana, Jason and Jackie laugh about their many wildlife encounters: from waiting for moose to cross the road on their way to school drop-off to a baby bear sneaking into Jackie’s truck. But, moose crossings and bears breaking & entering aside, it really is the tight-knit community that makes Montana home to the Wickens, and largely influences why they do what they do. Their businesses allow them to make connections with so many people in the region, and the community in itself helps fuel the success of its local businesses. The creativity and work ethic of Montanans is one of many draws to the state, as well as one of the reasons that the Wickens hold such deep love and ties to the place they call home. 

The Future

As for the future, the couple plans to further their efforts as active members of the community. In reflecting on their role in their neighborhood, Jason expresses that “growing with Bozeman, and the privilege of being able to grow with the community, allows us to be leaders.” To which Jackie exclaims, “Are we old now, Jason, is that what you said?!” The two laugh, while acknowledging that they are in community-driven businesses, which makes the work feel “really special.” They also recognize that they are in a “season of trying to be more calm, present, and settled in with the kids.” Plus, after casually mentioning his album with members of the “Turnpike Troubadours” in 2018, Jason mentions his plans to record a new album this summer.

The Wickens’ humility, among so many other admirable traits, lends to their charm, and is likely a major driver in the couple’s success. Whether it’s musical endeavors, HGTV specials, or a modern revamp of their family ranch, the Wickens continue to be a couple to watch.


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