Gypsy Tales

Brian Deegan joins us for Chapter 380. Brian Deegan has accomplished a lot in both freestyle motocross and business, but most importantly in raising a family and passing those lessons on to his children. Now Brian is taking a step back from his heavy involvement in Haiden and Hailie’s programs and sharing the knowledge he’s gained from competing, building business, and raising kids with his community. Introducing The General’s Army, a powerful network of high-achievers who share strategies, connections, and success together. In this chapter, we dive into everything Brian is doing with the General’s Army, talk about Haiden moving to the 450 class, and Metal Mulisha making a comeback and launching in Australia. Gypsy Gang, as always, thanks for watching. Drop a comment below, share this chapter with a friend, and hit subscribe so you never miss a new drop.

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00:00:00 Intro
00:01:04 Welcome Brian Deegan to the Podcast
00:01:33 General's Army
00:11:08 SOTA FUEL taste
00:12:42 Avoiding unhealthy foods
00:14:58 Brian sharing his knowledge
00:21:13 Disciplining his Children
00:26:15 Social Media / Speaking
00:29:56 Reading questions on the General Army
00:34:44 Why do you do what you do?
00:38:19 How much things have changed every decade
00:43:33 Working on your relationships
00:49:02 A message to motocross parents
00:56:14 Haiden still loving Moto
01:01:14 Investing in yourself
01:05:12 100 Hours with Jo / Money is suppose to come and go
01:20:00 God bless America
01:22:43 The Deegans fly private
01:26:43 Live calls with Brian Deegan zoom call
01:29:51 Brians involvement in Haiden's program going into the 450 Class
01:34:53 Deegan taking out Max Anstie
01:55:11 Haiden's changing the sport
02:03:58 The only person you can fix is yourself
02:13:58 Racing WSX
02:19:58 South African Motocross fans
02:25:38 Hows Haiden riding the 450
02:31:58 Wrecking rental cars
02:35:16 DEEGAN vs GYPSY Bike Build
02:42:34 Jo Shimoda Premier
02:45:25 More brands entering the sport
02:48:25 Electric bikes are taking over
02:51:25 Metal Mulisha expands to Australia
02:58:25 Haiden Deegan signs with Fox'
03:03:25 Haiden Deegan to the 450 Class
03:08:19 Closing

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Jason Weigandt joins us for Chapter 379! Jason is one of the most respected voices in motocross media a journalist who’s become a massive presence in the sport and a fan favorite across Supercross. What makes his story even crazier He never raced a dirt bike. So how did a lifelong moto fan go from the stands to becoming the main man at Racer X and calling Supercross races That’s exactly what we break down in this chapter. We dive into Jason’s journey the behind the scenes reality of motocross media and what it really takes to build credibility in the sport. Gypsy Gang, enjoy the show and don’t forget to like and subscribe below!

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00:00:00 Intro
00:01:16 Jo Shimoda 100 HOURS Announcement
00:02:21 Pod Starts
00:04:24 Dealing with Social Media Hate
00:05:37 World Supercross Commentary
00:17:34 Fans Don't Understand How Hard This Is
00:20:32 why everyone hates commentary
00:27:52 SOTA Fuel Taste Test
00:36:35 Appreciating the Gypsy Gang
00:39:07 Why I Quit The Podcast
00:58:34 Does Money Push Riders to Retire?
01:02:12 Brunt Workwear Ad
01:03:42 Top 5 Anaheim 1's of All Time
01:08:54 What Happen to the Party Era of Supercross
01:20:23 What got Jason into MOTO
01:27:23 How Jason Weigandt Got into MOTO
01:38:47 How Jason Learned to public speak
01:56:19 Jason's Path to Racer X
02:03:48 Jason's First Shot at Commentating
02:06:57 Being Overlooked for Years
02:14:53 Supercross has the best fans
02:29:14 Aura Frames Ad
02:30:32 Jason Weigandt's Role at Racer X
02:32:37 BlockBuster Turning Down Netflix
02:44:44 AI and Fake News in MOTO
02:55:55 Moto Fans want the real story
03:28:39 The Team at Racer X
03:37:21 Men go to Mars Ad
03:39:01 Justin Brayton
03:41:26 Supercross Racers Attention to Detail
03:53:11 Jasons Biggest Struggles
03:56:50 How to get a job in the Moto industry
04:08:16 The Early Days of Gypsy Tales
04:18:04 What makes a Great Leader
04:26:03 Closing

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Cooper Webb joins us for Chapter 378 of Gypsy Tales. Now a three-time Supercross champion, Webb heads into Anaheim 1 Supercross locked in and hungry, ready to battle for his fourth Supercross title.
Known as one of the most mentally feared competitors in Supercross, Cooper has built his legacy on resilience, pressure, and showing up when it matters most. You can never count him out. In this chapter, we dive deep into what makes Cooper tick, the mindset that separates him from the rest, and the untold stories behind his championship mentality.
We also break down the 2026 Supercross Championship, who Cooper sees as his biggest competition, and why he’s confident he can come out on top again.
A raw, honest look inside the mind of one of the greatest racers of his generation.
Gypsy Gang! Enjoy the show! — Remember to like, subscribe, and drop a comment below!

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00:00:00 Intro
00:01:11 Welcome back Cooper Webb
00:07:57 Fly Racing Ad
00:09:14 Struggles at KTM
00:19:30 Cooper Admits He Raced a Stock KTM
00:21:45 Doubt Fuels Cooper
00:26:24 SOTA Fuel Taste Test
00:27:32 Why Cooper Isn't Afraid to Fail
00:38:05 What It Took to Be a 3x Champ
00:45:33 Best Cooper Webb Yet?
00:49:25 Jett Lawrence Injured
00:53:34 Injury Plague in Supercross
01:06:24 100 Hours with Jo Shimoda
01:10:56 Drinking Beers Before the Main Event
01:16:42 Beating KTM and Chase Sexton Straight Up
01:22:39 Cooper Road to the Pros
01:31:29 Yamaha Ad
01:32:55 Coops Biggest Rivalry
01:42:31 Battling Eli Tomac
01:50:05 Why Cooper Hid an Injury
01:57:14 Inside the 2025 Supercross Title Fight
02:06:38 Out Smarting Chase Sexton
02:11:10 Inside the Mind of Cooper Webb
02:16:14 2025 Seattle Supercross
02:23:33 How it Feels Lining Up at A1
02:29:46 how Teammates Help Win Championships
02:36:00 Fly Racing's First 450 Champ
02:46:08 Buying Top Gun MX in North Carolina
02:50:20 Motosport Ad
02:51:29 Will Webb Race World Supercross
02:58:03 The Day Cooper Owned Motocross
03:03:00 Chasing a 450 Outdoor Title
03:07:45 Retiring from Pro Motocross!?
03:11:30 Can Haiden Deegan best Jett Lawrence
03:23:32 This is Why Jett Lawrence is so good
03:26:42 Cooper's Advantage This Supercross Season
03:31:46 Outro

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The 2025 Motocross of Nations did not disappoint! Team USA put on an incredible performance with their backup lineup, and we finally got to see the Coenen brothers’ raw speed go head-to-head against the Americans. There were standout rides across the board — Jo Shimoda repped Team Japan beautifully, while Tim Gajser and Team Slovenia scored their best-ever MXON finish! Team France crushed it once again with another podium, and the Lawrence brothers alongside Kyle Webster led Team Australia to back-to-back MXON victories! In this chapter of the podcast, we break down all the chaos — the crashes, track conditions, new rivalries, and the biggest storylines from the weekend. Tune in and join the debate 👇

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00:00:00 Intro
00:01:32 TEAM AUSTRALIA BACK 2 BACK MXON CHAMPS
00:05:38 Team Italy & Slovenia's MXON Performances
00:07:16 Best Ride of Hunter Lawrences Career!
00:14:45 Hunter Lawrence to MXGP!?
00:16:08 Coenen Brothers VS Lawrence Brothers
00:22:42 Team France is always in the mix
00:25:42 2027 TEAM USA ???
00:38:28 Best 250 Rider in the World
00:41:05 Kyle Websters Clutch Ride
00:49:54 Team USA's MXON Performance
00:55:53 BIKE GIVEAWAY - Honda CRF450R
00:59:07 RJ Hampshires MXON Crashes
00:59:46 Jo Shimoda Represents Japan
01:02:26 What EVERY Motocross Athlete Needs
01:03:45 Jo Shimoda MASSIVE NEWS!
01:05:23 Definition of a Privateer Budget
01:07:07 Bad Track Prep!?
01:10:39 Australian Supercross is Underway
01:18:16 Outro
01:18:51 Fist Ad

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Jason Anderson to Suzuki!? Jorge Prado NOT Going to Red Bull KTM!? Supercross Silly Season is Getting WILD! Riders are switching teams, contracts are changing, and the entire 2026 season is starting to take shape. We figured it was the perfect time to break down some of the craziest team swaps and rumors heading into the new season. Your favorite rider might be on a new team next year — where is Eli Tomac headed? Is Chase Sexton really moving to Kawasaki? What’s next for Justin Barcia? Not to mention the MXGP stars like Tim Gajser and Jeffrey Herlings, who will be lining up on new brands in 2026 as well. Let’s dive into everything happening in this year’s Silly Season — it’s one for the books.

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00:00:00 Silly Season Intro
00:01:02 Did Jorge Prado Ruin it for the Euros?
00:10:54 Destination Yamaha Ad
00:12:20 Was it Jorge or was it the bike?
00:18:55 Jason Anderson to Suzuki!?
00:23:26 F1 VS Supercross - Should we Copy the Model?
00:27:01 Tom Vialle and Jeffery Herlings to HRC Honda
00:30:35 Motosport Ad
00:32:20 Jo Shimoda keeps Honda and Drink Weird Deal
00:34:58 Australian Supercross
00:38:13 FIM World Supercross
00:42:03 Eli Tomac to Red Bull KTM
00:46:31 New rides for Chase Sexton and Christian Craig
00:48:59 Vince Friese signs with Stark!?
00:49:49 Brunt Boots Ad
00:51:18 Voice messages from the Gypsy Gang
00:56:58 Closing
00:57:58 Fist Handwear Ad

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