BAILEY PODCAST XCHANGE

👉 'WIN MORE OR HIT THE DOOR' SESSION 3 EPISODE 1 IS OUT NOW

POV: You sit down at Mississippi Stud thinking, “I know what I’m doing.” 😂

Five minutes later:

“WHY THE F**K DID I BET THAT?”

Welcome to Win More or Hit the Door — where the strategy is questionable, the confidence is high, and somehow the bankroll is still alive. 🃏💰

Watch the hand.

Judge the decisions.

Tell me what YOU would’ve done.

We start by ranking band merch, and Bailey has ONE artist sitting at the top. 🎤

Then things take a turn into true-crime territory. 😳

Have you seen Dane Cook’s new documentary, Funny Money? It’s not just good… IT’S BRILLIANT!

The story involves allegations of millions of dollars stolen by his own brother, a mobster-style plot twist, and a sister-in-law on camera who has Bailey raising even MORE questions. 👀

Bailey believes there’s a whole lot more to this story than meets the eye.

💰 Get the full recap, Bailey’s theories, and a masterclass in HOW TO GIVE SOMEONE A RECEIPT THEY’LL NEVER FORGET.

👉 Full video episodes FREE on Spotify + YouTube 🎥

👉 3 shows • 5 days a week • 1 feed

👉 Subscribe to unlock exclusive shows 🔓

👉 Everything at jasonbailey.com

Being sick hits differently when you’re empty nesters… but Rachel has a confession that Jason is WAY too excited to hear. 😳😂

Then Rach opens the SugarSplash sexy-time box, and suddenly things go from sick-day survival to NSFW marriage counseling. 👀

🤒 Empty nesting

🤫 A shocking confession

🔥 Dirty talk

💊 Muscle relaxers

🎁 And a box that should probably come with a warning label.

👉 Full video episodes FREE on Spotify + YouTube 🎥

👉 3 shows • 5 days a week • 1 feed

👉 Subscribe to unlock exclusive shows 🔓

👉 Everything at jasonbailey.com

👉 'WIN MORE OR HIT THE DOOR' SESSION 2 EPISODE 3 IS OUT NOW

POV: You sit down at Mississippi Stud thinking, “I know what I’m doing.” 😂

Five minutes later:

“WHY THE F**K DID I BET THAT?”

Welcome to Win More or Hit the Door — where the strategy is questionable, the confidence is high, and somehow the bankroll is still alive. 🃏💰

Watch the hand.

Judge the decisions.

Tell me what YOU would’ve done.

👉 Full video episodes FREE on Spotify + YouTube 🎥

👉 3 shows • 5 days a week • 1 feed

👉 Subscribe to unlock exclusive shows 🔓

👉 Everything at ⁠jasonbailey.com

Bailey shares a frustrating conversation with the State Attorney that leaves him seriously disappointed—and sparks a bigger question:

How many people are actually in jobs they shouldn’t be doing? 👀

Could AI fix that?

Enter “Coyotec”—the AI radio DJ making waves in LA. Is it really killing it… or is radio just pretending everything is fine? 😂

Bailey has some opinions. Radio people probably won’t like them.

And just when you think the future looks bleak, the episode ends with an AI guy that looks like a Harry Potter nerd warning us about the dangers of AI.

🎙️ Feel better about the future? Yeah… neither do we. 😂

👉 Full video episodes FREE on Spotify + YouTube 🎥

👉 3 shows • 5 days a week • 1 feed

👉 Subscribe to unlock exclusive shows 🔓

👉 Everything at jasonbailey.com

RayJay recap the big Garth Brooks night, including Rach’s favorite picture of the evening… which you’ll NEVER see.

Friends from out of town join them before heading off on a Disney cruise, which sparks a trip down memory lane about family vacations growing up.

The conclusion? Parents today are WAY better at vacations for their kids. Do you agree?

But Jason remembers one childhood vacation VERY clearly…

Because he got LOST.

Or…

WAS HE LOST ON PURPOSE?! 👀

👉 Full video episodes FREE on Spotify + YouTube 🎥

👉 3 shows • 5 days a week • 1 feed

👉 Subscribe to unlock exclusive shows 🔓

👉 Everything at jasonbailey.com

👉 'WIN MORE OR HIT THE DOOR' SESSION 2 EPISODE 3 IS OUT NOW

POV: You sit down at Mississippi Stud thinking, “I know what I’m doing.” 😂

Five minutes later:

“WHY THE F**K DID I BET THAT?”

Welcome to Win More or Hit the Door — where the strategy is questionable, the confidence is high, and somehow the bankroll is still alive. 🃏💰

Watch the hand.

Judge the decisions.

Tell me what YOU would’ve done.

👉 Full video episodes FREE on Spotify + YouTube 🎥

👉 3 shows • 5 days a week • 1 feed

👉 Subscribe to unlock exclusive shows 🔓

👉 Everything at jasonbailey.com

THE 100 BEST TV SHOWS LIST JUST GOT WEIRD.

The fellas tackle football celebrations, testosterone, shrinkflation, and… sexy-time products. 😂

Then they dive into the 100 Best TV Shows of the 21st Century—and the omissions have everyone losing their minds.

And somehow PEN15 is ahead of RuPaul and behind Chappelle which makes it weird.

At that point, the fellas realize they’re basically six-year-olds trying to discuss television. 🤣

👉 Full video episodes FREE on Spotify + YouTube 🎥

👉 3 shows • 5 days a week • 1 feed

👉 Subscribe to unlock exclusive shows 🔓

👉 Everything at jasonbailey.com

GARTH BROOKS, BOOTS & A 1X PEANUT NIGHTGOWN?!

RayJay are getting ready for the Garth Brooks show—and Jason finally tells the story of his special connection with Garth and what happened when they first met.

Then Jason decides he needs cowboy boots… except he has ZERO idea how to shop for them. Rach takes over. 😂

Is Rach going to a lesbian lunch? We’re not judging… we’re just trying to understand the event. 👀

And then comes Rach’s new motto:

“BUILT FOR COMFORT, NOT SPEED.”

Enter the 1X Peanut nightgown. 😂

Does Jason find it sexy? Does Rach care?

Absolutely nobody knows.

👉 Full video episodes FREE on Spotify + YouTube 🎥

👉 3 shows • 5 days a week • 1 feed

👉 Subscribe to unlock exclusive shows 🔓

👉 Everything at jasonbailey.com

Trying to make something out nothing in this episode

Welcome to WIN MORE OR HIT THE DOOR! ♠️

My NEW weekly gambling series is here!

Every Friday at 5AM, follow through an entire session — the wins, the losses, the swings and everything in between.

First up: MISSISSIPPI STUD!

6’s–10’s push… anything higher pays. And unlike most casino games, you’re not playing against another player — you’re playing your cards against the board trying to hit a pair of Jacks's or better to get paid.

This game has A LOT of swings. Get ready!

Big thanks to orangecitypoker.com for hosting Orange City Poker