Episode 41: Ray Handal - The Surprising Journey from Jamaica Handicapping to Training Elite Racehorses

Episode 41: Ray Handal - The Surprising Journey from Jamaica Handicapping to Training Elite Racehorses

Most trainers wait years for a breakthrough, Ray Handal got his in just his second start, winning at 75-1 and instantly commanding attention. It was the kind of upset that makes the racing world take notice. But that moment wasn’t lightning in a bottle. It was years in the making, rooted in resilience, early independence, and a childhood in Jamaica where he learned the game by handicapping races with his visually impaired father. Ray’s story is less about a single longshot win, and more about the discipline and vision it takes to build something that lasts. Interested in owning part of a team of racehorses? Learn more at firstrodeoracing.com In this episode, Ray takes us deep into a journey that began on the backstretch of Calder Race Course, where at just 15, he was hot walking for legendary trainers and dreaming of one day training winners. From early mornings in Colonial Downs’ dorms to riding in Kentucky, Ray shares how he transformed from a kid skipping school for his passion into a top trainer whose horses are competing at the highest levels. He discusses the importance of adaptability across surfaces, from dirt to Tapeta to synthetic, revealing how his extensive experience helps him prepare horses for any track or challenge. Discover how Ray’s focus on long-term vision and diversifying experiences—working with great mentors like Kenny McPeak and Tony Dutrow—gave him insights into both the horseman’s art and the business side of racing. He shares the lessons learned from his most influential trainers and why staying hungry kept him pushing through initial setbacks. Plus, get a behind-the-scenes look at how he’s preparing for a rising star—an Oscar Performance colt heading to his barn soon—where pedigree meets strategy, and surface versatility is key. Why does this matter? Because Ray’s story exemplifies resilience, innovation, and strategic thinking in a sport that’s constantly shifting. Whether you’re an aspiring trainer, a racing enthusiast, or just curious about what it takes to succeed in such a competitive industry, this episode offers concrete insights on evolving with the game, embracing new surfaces, and making smart investments in future generations of horses and trainers. Perfect for anyone hungry to understand the true grit behind harnessing potential, this episode will inspire you to adapt, learn from every step, and never underestimate the power of patience. Ray’s philosophy of blending diverse experiences with sharp racing instincts can reshape how you see success—on the track and in life. Whether you’re captivated by the story of a second racehorse victory or exploring how to future-proof your operation in a changing racing landscape, this episode will leave you motivated and ready to take your own shot—just like Ray did—on that big stage. Ray Handal is a leading trainer known for his strategic approach and innovative mindset, with a career spanning from humble beginnings on the backstretch to winning big in graded stakes. His journey illustrates how perseverance and adaptability can turn a childhood dream into a racing renaissance. Timestamps: 00:00 Introduction 02:00 Ray's Early Days in Jamaica 10:00 Transition to U.S. Racing 20:00 Key Mentors and Lessons Learned 30:00 Training Philosophy and Techniques 40:00 Preparing for Future Challenges 50:00 Closing Thoughts and Advice

Episode 40: Jose Santos, Jr. - Inside the World of a Jockey Agent

In this episode, jockey agent Jose Santos Jr. shares his journey from aspiring jockey to influential agent, offering insights into the horse racing industry and the role of technology in its future. He discusses the challenges and innovations shaping the sport today. Interested in getting off the sideline and into the sport of horse racing? Learn more at firstrodeoracing.com [http://firstrodeoracing.com] TIMESTAMPS [0:28] Jose's Journey Discussion on Jose's path to becoming a jockey agent and the highs and lows of the sport. [2:03] What is a Jockey Agent? Jose explains the role of a jockey agent and how it compares to the entertainment industry. [4:25] Growing Up in Horse Racing Jose shares his background, growing up in a family of jockeys, and his initial aspirations. [6:39] The Story of Funny Side A behind-the-scenes look at the legendary horse Funny Side and Jose's father's involvement. [9:06] Derby Experiences Jose talks about the significance of the Kentucky Derby and personal experiences. [11:04] Transition to Jockey Agent How Jose transitioned from aspiring jockey to agent, including challenges and successes. [13:47] Career Challenges and Opportunities Jose discusses the difficulties faced in his career and the pivotal moments that shaped his path. [19:13] Handicapping and Tools Insights into the tools and strategies Jose uses for handicapping and managing horses. [24:37] Innovations in Horse Racing Discussion on creative race conditions and the importance of transparency in the industry. [32:05] Technology and AI in Racing Jose's thoughts on the potential of AI and technology to transform horse racing. [36:30] Future of Horse Racing Ideas for improving the sport, including fan education and better support for trainers. [50:00] Rapid Fire Questions Fun, quick questions about Jose's favorite tracks, horses, and personal insights.

Episode 39: Gavin Saylor - Inside the Creative Mind of Gavzilla (Viral Hats, Celebrity Endorsements, and the Art of Standing Out in Fashion & Sports)

In this episode, Gavin Saylor, aka GavZilla, shares his inspiring story of turning a passion for barbering, fashion, and creativity into a viral brand with designs that took the internet by storm. Discover how personal branding, unique design, and bold moves can make you stand out in competitive markets. Connect with GavZilla on IG: https://www.instagram.com/gavzillaaa/ [https://www.instagram.com/gavzillaaa/] Key Topics: ‍ ‍ Gavin’s background and how he transitioned from college lacrosse at Hartford to full-time barbering and clothing design The creative process behind GavZilla’s unique hats and clothing, including jacket and accessory designs How viral videos and social media made GavZilla’s designs iconic, with millions of views on Instagram The story of celebrity and athlete endorsements, and the impact of virality on brand growth The intersection of horse racing culture and fashion, with GavZilla’s entry into the sport's apparel scene Building a community and networking at horse races, including influencer engagement and event experience Challenges of design imitation and protecting creative work in the digital age Future goals: expanding into race day attire, exclusive drops, and collaborations with sports figures The inspiring ethos of doing things differently—whether in fashion, sports, or branding ‍ ‍ Timestamps: ‍ ‍ 00:10 - Introduction to Gavin Saylor and his creative journey 02:46 - From college to barbering and clothing experiments 04:27 - What motivated him to pursue barbering full-time 06:16 - The creative techniques behind Gavzilla’s hair and fashion designs 07:29 - The process of designing custom, one-of-one pieces 09:08 - Going viral with the famous crimped hats and celebrity adoption 10:53 - The story behind viral videos with millions of views 12:24 - How viral success shaped Gavin's confidence and brand visibility 14:15 - The first celebrity to wear Gavzilla’s hats and the impact on growth 16:02 - The psychology of making pieces for specific clients and fans 17:20 - The importance of authenticity and putting yourself out there 18:37 - The approach to creating backlogged vs. client-specific designs 19:32 - Highlighting the most memorable piece—Machine Gun Cali charm 21:18 - Viral moments, international sightings, and celebrity reach 22:45 - Challenges with imitation, leaks, and protecting intellectual property 25:01 - Staying grounded despite fame and success 26:09 - Aspirations to evolve Gavzilla into a full brand beyond hats 27:20 - Collaborating with First Rodeo on custom apparel and the design ethos 28:10 - Entering the horse racing fashion scene and its potential 30:56 - The community and networking opportunities at horse races 33:20 - The culture and social energy of racing events 35:31 - The influence of celebrities and social media on horse racing’s visibility 36:53 - The modern approach to race day attire, blending tradition with innovation 39:34 - The excitement of Kentucky Derby and influence of racing culture 40:39 - Opportunities to grow within the sport’s apparel and brand ecosystem 43:00 - Designing race day gear and the evolution of fashion at major racetracks 45:00 - The intersection of style, culture, and the sport’s future 47:39 - Using racing as a platform for personal branding and community building 50:50 - The impact of social media, influencers, and digital engagement on the sport 53:36 - The parallels between golf's renaissance and horse racing’s revival 55:50 - The importance of storytelling and shared experiences in racing traditions 58:00 - Rapid-fire questions: favorite racetracks, sports icons, and future collaborations 62:44 - Wrapping up with Gavin’s plans and the excitement for future ventures ‍ ‍   ‍ ‍ Interested in getting off the sideline and into the sport of horse racing? Learn more at firstrodeoracing.com [http://firstrodeoracing.com] ‍ ‍

Episode 38: Frank Turman - From Attending the Derby as a Fan to Winning Graded Stakes As An Owner

Summary In this conversation, Frank Turman shares how a chance encounter at a Kentucky Derby laid the pathway to being a graded stakes winning owner. Frank & Matt recount their wins at Oaklawn in February, where the two met and discuss how Frank got his start as an owner. The conversation covers how Frank got connected to a bloodstock agent, Mike Maker, and Norm Casse. They talk through some of the next "firsts" that Turman Racing Stables is chasing, as well as ideas to grow the game. Interested in owning a piece of Two Seven O and all the horses in First Rodeo? Learn more at firstrodeoracing.com [http://firstrodeoracing.com]

Episode 37: Anthony Montedoro - Racing, Recovery, and Relationships: A Jockey Agent’s Story

Summary In this engaging conversation, Anthony Montedoro shares his journey from growing up near Monmouth Park to becoming a successful jockey agent. He discusses the vibrant atmosphere of horse racing, the importance of community, and his personal struggles with addiction. The conversation delves into the mechanics of entry day, the relationships built in the racing world, and the future of horse racing in New Jersey. Montedoro emphasizes the need for innovation to attract new fans and the impact of technology on gambling. The discussion concludes with rapid-fire questions, revealing Montedoro's favorite tracks and horses, and his advice to his younger self. Interested in owning a piece of Two Seven O and all the horses in First Rodeo? Learn more at firstrodeoracing.com [http://firstrodeoracing.com] Takeaways - Anthony grew up near Monmouth Park and was introduced to racing at a young age. - He struggled with addiction for many years but has been sober for eight years. - The camaraderie in the racing community is unmatched and essential for success. - Building relationships with trainers and jockeys is crucial for a jockey agent. - Entry day mechanics involve communication between trainers and agents to secure rides. - Family-friendly events and education are key to attracting new fans to horse racing. - Horse racing must evolve to compete with other forms of gambling. - The impact of technology on gambling is significant and needs to be addressed. - Montedoro believes in the importance of humanizing relationships in the racing industry. - He emphasizes the need for transparency and collaboration among horsemen and regulatory bodies.