Gypsy Tales

Bobby Regan joins us for Chapter 381. Bobby has taken Star Racing Yamaha from a small privateer operation to the most dominant team in the sport over the last decade, leading riders like Cooper Webb, Haiden Deegan, and Eli Tomac to championships. Bobby shares his story from his younger years to where the team is today, opens up about how gambling helped fund the early days of Star Racing Yamaha, and breaks down the team dynamics and tactics he used to get the most out of his riders—including pinning Cooper Webb and Jeremy Martin against each other. He also explains why he was so committed to Cooper Webb, what he saw in him early on, and even shares what Haiden Deegan is really like as both an athlete and a person. Gypsy Gang, as always, thanks for listening. Drop a comment, like, and subscribe! Monster Energy 🟢 https://www.monsterenergy.com/en-us/ Get the Gypsy Tales Dixon Flannel! US 🇺🇸: https://www.dixxon.com/products/gypsy-tales-flannel?srsltid=AfmBOoqrfeo5qXJKfpnnZpUMapDkyCUniuPeqkDWDfYkbwX03iAQY6hx AUS 🇦🇺: https://www.dixxon.com.au/collections/new-releases/products/gypsy-tales-flannel The most potent & natural testosterone stack on Earth 💪 Check it out here: https://mengotomars.com/ 🖼️ Frame your biggest moments https://auraframes.com/ 🧤 FIST HANDWEAR: http://www.fisthandwear.com CODE: GYPSYGANG for 15% off 🛒 Shop Gypsy Tales merch: https://us.gypsy-tales.shop/ 🎙 SUBSCRIBE TO THE PODCAST: https://www.youtube.com/channel/UCsBG… 📸 FOLLOW GYPSY TALES ON INSTAGRAM: @gypsytalespodcast 00:00:00 Intro 00:01:30 Welcome Bobby Regan to The Podcast 00:02:57 A Brief Background on Bobby 00:08:37 Dixxon Flannel Ad 00:09:28 Rewinding to the Start of Bobbys Career 00:16:50 How Star Racing Yamaha Began 00:20:43 The Stewart Family 00:22:34 How Star Racing Became a Winning Team 00:35:20 Aura Frames Ad 00:36:36 Gambling Stories 00:41:24 Bobby's Secret to Success 00:48:28 Buying the Goat Farm and Becoming Dominant 00:57:07 Star Racing Yamaha's First Champion! Jessica Patterson 01:01:42 Men go to Mars Ad 01:03:21 Star Racings First Pro Motocross Championship 01:13:20 What Cooper Webb's 2025 Supercross Championship Meant 01:17:44 Losing Chase Sexton to Geico Honda 01:21:20 Eli Tomac 01:22:37 What is Haiden Deegan Really like!? 01:26:21 Untold Haiden Deegan Story 01:27:26 Why Riders Leave the Program 01:30:12 Star Racing's Next Champion 01:32:19 Fist Handwear Ad 01:33:45 Star Racings Biggest Rule 01:39:00 Cole Davies Whoop Speed 01:40:59 Millsaps Training Facility 01:42:20 Best Rookie Season Ever!? 01:46:44 Australias Next Champion!? Blake Bohannon 01:48:51 What you Need to Know about Bobby Regan 01:54:01 Haiden Deegan is like a Son to Bobby 01:54:44 Outro See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.