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

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

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.

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/

Key Topics:

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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

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Timestamps:

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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

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Interested in getting off the sideline and into the sport of horse racing? Learn more at firstrodeoracing.com

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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

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

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.

Summary This conversation centers around the questions submitted by those that are partners in First Rodeo / own a piece of Two Seven O. Matthew and Eric Gary discuss their recent win at Oaklawn Park, Eric's journey in horse racing, and the training regimen for TSO. They delve into the strategies for future races, the need for uniform regulations in horse racing, and share personal insights through rapid-fire questions. The discussion highlights the dedication required in the sport and the camaraderie among those involved. Interested in owning a piece of Two Seven O and all the horses in First Rodeo? Learn more at firstrodeoracing.com Takeaways - Eric's journey into horse racing began at age 13. - He transitioned from aspiring jockey to trainer due to injuries. - Training horses requires perfect preparation for success. - Winning a race is a significant achievement in a competitive field. - Uniform regulations in horse racing are essential for fairness. - The dedication of horsemen often goes unnoticed by the public. - Horse 270 has a unique personality and training needs. - Future races for horse 270 are being carefully considered. - The camaraderie in horse racing is a key aspect of the sport. - Eric emphasizes the importance of enjoying the journey in racing.

Summary

Justin Adakonis, the current championship leader of the MX-5 Cup, shares his journey from karting to professional racing. He discusses the intricacies of race strategy, particularly at Daytona, and explains the structure of the IMSA series. The conversation delves into the business model of racing, highlighting the importance of sponsorship, funding, and personal branding for drivers. Justin reflects on his experiences, the challenges of balancing education with racing, and his aspirations for the future. The discussion also draws parallels between motorsports and horse racing, emphasizing the strategic elements common to both sports.

Interested in owning your own sports team?

Limited spots open in 2026 - Text Matt (732-947-2792) or go to www.firstrodeoracing.com for more info

Summary

In this engaging conversation, Olivia Witkowski shares her journey into the world of horse racing photography. From her childhood love for horses to her experiences at the Saratoga Special, Olivia discusses the importance of storytelling in racing through photography. She highlights the unique energy of mornings at the track, the excitement of big race days, and the differences between Saratoga and Gulfstream Park. Olivia emphasizes the need to preserve the history of horse racing and expresses her hopes for the future of the sport. The conversation concludes with rapid-fire questions that reveal Olivia's favorite aspects of racing and her aspirations in photography.

Interested in owning your own sports team?

Limited spots open in 2026 - Text Matt (732-947-2792) or go to www.firstrodeoracing.com for more info

Summary

In this conversation, Jamie Haydon shares his extensive experience in the horse racing industry, detailing his journey from working on the Keeneland maintenance crew to his current roles at the Jockey Club and Grayson Jockey Club Research Foundation. He discusses the importance of equine research, the role of the Jockey Club in regulating the sport, and the future of horse racing, emphasizing the need for increased purses and better wagering options. The conversation also touches on the cultural significance of horse racing in communities and the importance of educating new fans about the sport.

Interested in owning your own sports team?

Limited spots open in 2026 - Text Matt (732-947-2792) or go to www.firstrodeoracing.com for more info

Summary

In this engaging conversation, Brian hosts Marcus and Brendan from Horse Racing Kings, who share their journey into the horse racing industry at a young age. They discuss their interview approaches and their aspirations to grow their community and content creation efforts. The conversation highlights their experiences, challenges, and the excitement of engaging with notable figures in the industry, as well as their goals for the future.

Interested in owning your own sports team?

Limited spots open in 2026 - Text Matt (732-947-2792) or go to www.firstrodeoracing.com for more info