Should’ve Been A Cowboy Podcast
Saddle up with hosts Cowboi Cole & Filipe Masetti as they take you for a ride into the world they love and know: the western & cowboy lifestyle! Cole & Filipe team up to bring you engaging, fun and wild west chats with guests from all walks of life. Mount up and let’s chat!
Episodes

2 days ago
2 days ago
Cowboy Kynan in the house! The man who has produced the Calgary Stampede, The American and all the way to your local bull riding! Kynan is a lover of the sport and a lover of telling the stories of the athletes in our world. Growing up in a rodeo family, fighting bulls professionally to producing incredible events all over North America, Kynan has some great stories to tell!
@shouldvebeenacowboypodcast @filipemasetti @cowboi_cole @kynanvine

Tuesday Apr 15, 2025
Tuesday Apr 15, 2025
Long Rider, mental health advocate and a lover of horses, Jodie Morton! Jodie sat down with the boys and talked about her nomad lifestyle, traveling and living off the back of the horse and how a traditional 9 to 5 just doesn't fit the life she wants to live. Great episode with the Aussie cowgirl!
Follow our socials: @shouldevebeenacowboypodcast @filipemasetti @cowboi_cole @greengoldandblues

Tuesday Apr 08, 2025
Tuesday Apr 08, 2025
The boys schedules align and are in studio for an episode of shooting the sh*t about the previous Texas Swing of rodeos! They talk Riley Webb, who would win a match between Logan Bird VS Kyle Lucas and future guests!
Follow our socials: @shouldvebeenacowboypodcast @filipemasetti @cowboi_cole

Tuesday Apr 01, 2025
Tuesday Apr 01, 2025
Courtenay Dehoff has told the FUNNIEST story on this podcast to date! You NEED to listen to the end to hear about an old college rodeo story. Courtenay has lived an incredible life and has the stories to show for it. From growing up on a cow calf operation, living in the big cities as a network news host and having her come to Jesus moment that brought her back to her western roots, this cowgirl is paving her own path in this bustling world!
FOLLOW OUR IG's: @shouldvebeenacowboypodcast @cowboi_cole @filipemasetti @courtdehoff

Tuesday Mar 25, 2025
Tuesday Mar 25, 2025
Our first Olympic athlete, Nicole Silveira! A Brazil native who moved to Calgary with her family as a young girl, she found herself pursuing a sport she would've never considered had she stayed in Brazil. in 2018 when she had an opportunity to try Skeleton and loved it, she set her sights on the 2022 Olympics and she found herself making the trip to represent her country!
FOLLOW OUR IG's: @shouldvebeenacowboypodcast @cowboi_cole @filipemasetti

Tuesday Mar 18, 2025
Tuesday Mar 18, 2025
Southern Alberta cowgirl, CFR qualifier and NFR Open Breakaway champion, Jenna Dallyn! The daughter of team roping legend, Rocky, Jenna is making her own waves in professional rodeo! A top competitor in the Canadian circuit, Jenna finds herself top 12 in the world as she hits the winter PRCA rodeos for the first time. The boys chat with Jenna about Calgary Stampede adding breakaway roping to the main rodeo, transitioning from being a goat tier to a breakaway roper and much more.
FOLLOW OUR IG's: @shouldvebeenacowboypodcast @cowboi_cole @filipemasetti @jennadallyn

Tuesday Mar 11, 2025
Tuesday Mar 11, 2025
The boys are back together for an exclusive episode and boy oh boy do they have a lot to catch up on! Between Cowboi Cole's 'Denied Access to the USA' story and Filipe GETTING MARRIED in Patagonia, you're not going to want to miss this episode.
FOLLOW OUR IG's: @shouldvebeenacowboypodcast @cowboi_cole @filipemasetti

Tuesday Mar 04, 2025
Tuesday Mar 04, 2025
22 years in the Army, SkiMo athlete and co-founder of War Party Ranch! Jeremiah Wilber talks to Cowboi Cole about his time as a kid in Las Vegas, training to become a Green Beret and using the power of the horse to help others build up their own personal strength after hardship.
Follow our socials: @shouldvebeenacowboypodcast @filipemasetti @cowboi_cole @jeremiah_blackbeard

Tuesday Feb 25, 2025
Tuesday Feb 25, 2025
CORB LUND!! Need we say more? The legend in western music himself, Corb chat with Filipe and Cole about his days in a metal band, his friendship with Ian Tyson and his pure passion for performing his music for the people. This is a must listen front to back episode! Enjoy!
FOLLOW OUR IG's: @shouldvebeenacowboypodcast @cowboi_cole @filipemasetti @corblund

Tuesday Feb 18, 2025
Tuesday Feb 18, 2025
From pucks to bucks! Nick Tetz is a 2x PBR Canada Champion but it didn't used to all be about ridin bulls. A talent on the ice and pressure from his dad to take hockey as far as it could go wasn't enough to hold back the drive to be a cowboy and a top tier bull rider!
FOLLOW OUR IG's: @shouldvebeenacowboypodcast @cowboi_cole @filipemasetti @tetznick_

YOUR HOSTS
Cowboi Cole! A southern Allberta