Dogs barked as I rolled up to Guess Family Farm in Spencer, Oklahoma. Within seconds, Richie was out the door with a warm wave. Richie showed me around the farm, highlighting the new pond that they put in after clearing out a pasture and the new dirt track his sons, Cory and Zach, come to practice on.
From the Pony Express wrapped trailer to the horses in the pasture, it is clear there’s one thing on this family’s mind: rodeo. But rodeos are something Tiffany and her brothers started getting the family involved with. While so much of rodeos and agriculture in general has generational legacies guiding it, for the Guess family, they dove in headfirst into this world.
"I don’t remember going to my first rodeo. But I remember going to the Okmulgee Rodeo a while back after graduating high school and seeing my brother ride Pony Express."
"I was just like, man, this is a rodeo. It was amazing. The crowd interaction, the announcer - everything was on point.”
That feeling had Tiffany hooked. But curating a party has always been a part of Tiffany, long before then. Richie told me more than a few stories about Tiffany in high school taking the mic and getting energy rising at events.
"I just get uncomfortable and feel like there should be more interaction from the crowd. It’s cringy, because you’re there not getting the whole experience. It doesn’t matter what the event is, you have to make it fun in order for people to come back.”
It didn’t take long for Tiffany to find her way to get involved with rodeos. After meeting the MC and producers of rodeos, Tiffany got comfortable enough to ask to run the sound.
“I remember just, like, asking, ‘Can I play the music?’ And then finally, one of the music directors, Roy "Musicman" Henderson, gave me a good recommendation to Marcous Friday to let me start helping him out. And just from there, Marcous and I have been inseparable.”
After years of working with Romon Jones to get started, Tiffany began traveling the country MC’ing rodeos, weddings, and even funerals. It only takes a few minutes upon meeting her to understand just exactly why this is her thing. Working a crowd takes more than just a personality, it takes a lot of awareness to read people and understand them. When you attend one of her events, you can see her working the crowd like a conductor would command an orchestra. And the results are easy to see. Go to a few different rodeos and you can feel a difference attending one where Tiffany is on the mic.
But just handling a mic during the event wasn’t all that Tiffany wanted to do.“I actually tried to get in on other rodeos just to co-produce. Wanting to be a part of the rodeo, that’s always been something in me. I always just want to do more and more. So I wanted to start having my own and getting into the producing part."
Starting a business is difficult; however, most of us know a few entrepreneurs in our communities. While so many rodeos stand on decades of experience, building one from scratch feels like a daunting undertaking. But Tiffany had built a strong community over the years to help her get started.
“Everyone was like, just have your own, you know. So I went ahead and did it.”
After years of thinking about it, Tiffany finally took the leap and began planning Legacy Rodeo. She began gathering her network of who she knew was the best in the business to put it together. Plans began coming together, as did the anxiety.
“I was very nervous going in, especially with the risk that there is. You can have a rodeo and nobody show up. You have all this money tied into it. It was pretty much me on my own. Then I told my parents about it, and they always support me in everything I do. And then Marcous Friday, just everybody pulling together and helping me encourage these cowboys and cowgirls to come down to Purcell.”
The result? The inaugural Legacy Open Rodeo was an instant hit. With a huge platform from the Pony Express teams, crowds gathered in Purcell to kick off one of the highlights of summers in Oklahoma. Lines formed as cars crowded to get in to find a seat under the halogen lights.
“Everyone was really supportive. I even had some contestants say, ‘Hey girl, I’m coming out of retirement to come ride.’ (That night) I did the DJ'ing and Marcous was just like ‘Tiffany, look at the crowd.’ He’s been throwing rodeos for 20 something odd years, so hearing it from your mentor that you did great, I shed a couple tears. I was very happy.”
The name Legacy Rodeo speaks for itself. It stands as Tiffany’s gift to Oklahoma. Her hope is it continues on, carrying the name for generations forward. And each year, she has plans to grow it. In its second year, the rodeo began a kids area to keep families entertained as the parents competed or watched. More riders came out, crowds continued to grow.
And it is still only year two.
“I think the rodeo is bringing back the family aspect to rodeo life. And I hope it shines a light on Pony Express. Pony Express is a great event that deserves way more recognition than it gets from open rodeos.”
Tiffany might not come from generations of riders, but there’s no doubting her family's commitment to the rodeo.
From the Guess Family Farm to the Legacy Open Rodeo, the Guess family reminds us that it is never too late to start building a legacy.
