Steve Caballero's love for skateboarding started at a young age. Growing up in San Jose, California, he and his friends would often skateboard around their neighbourhood for fun. Steve shares his fond memories of asking his father to take him to the local skateparks and bowls, so he could practice. At the time, there wasn't a lot of information on how to become a pro skater, and the skateboarding industry was still in its early stages. Steve found motivation from his idols such as Eddie Elguera, from seeing them at the parks or reading about them in magazines. 

Steve looks back on the early days of skateboarding, he mentions how there were no videos or films to learn from or emulate. Everything was learned through trial and error, step-by-step photos and word of mouth. For Steve Caballero, growing up skateboarding in the 70s and 80s meant seeking out fellow skateboarders and sharing tricks and techniques. Steve recalls getting the latest Thrasher magazines with the photo sequences of tricks and heading to the skateparks to study the photos and learn the tricks. Steve's dedication to the sport eventually caught the attention of legendary skateboarder and entrepreneur, Stacy Peralta. He was invited to join the Bones Brigade, a group of elite skaters who were changing the game. With his signature "half cab" trick and distinctive style, Steve quickly became recognized as one of the top skateboarders in the world.

Steve talks about Overcoming Challenges and Finding Success in the Skateboarding World, He mentions how He had to train his mind to accept that in order to succeed you must fail.

Caballero opens up about Joining the Bones Brigade and how it was a pivotal moment in his career, as it gave him the opportunity to work with some of the most influential skaters in the world, including Tony Hawk, Lance Mountain, and Rodney Mullen. Becoming a pro skater was a dream come true for Caballero, and he relished the opportunity to turn his passion into a career.

Steve Caballero shares that he is more than just a skateboarder. He's a musician and artist as well. When he's not busy shredding at the skatepark, you can find him creating new music or working on art pieces.  His love for music started at a young age, In 1986, he formed his band, The Faction, and later in life found their lane in music with his latest project and touring band Urethane. Caballero's artistic side is also something that has always been a part of him. He started drawing when he was a kid and continued to do so throughout his career as a professional skateboarder. His love for drawing inspired him to create graphics for his skateboard sponsor, Vans.

During the Motivational podcast, "It Was All a Dream," skateboarding legend Steve Caballero opened up about his family roots and the inspiration behind his love for dragons. It wasn't until he was in his 30s that he discovered his Japanese bloodlines, which gave him a new sense of pride in his heritage. In fact, he shared that he unknowingly connected with his heritage through his love for dragons. Steve also talked about how his good friend and fellow skateboarder, Tony Hawks, gave him the nickname "Cab Dragon," which has stuck with him ever since.

Steve reflects on his career as talks about his proudest moment, When it comes to achievements, Steve Caballero has a long list. He's a five-time world skateboarding champion, has multiple signature skateboard decks and the longest signature shoe collection to date with Vans, and has even been featured in the iconic video game Tony Hawk's Pro Skater.

Finally, Caballero offers some valuable advice for the future generation of skateboarders. Steve breaks down how you can look at going pro and what he can offer information to anyone out there looking to follow his path, work hard and stay dedicated.

Overall, the future of skateboarding is bright and I am excited to see where it goes. Just remember to have fun, be authentic, and never give up on your dreams.