Tip Your Caddie

Ep. 22 - Gretzky's Caddie Calls Out BizNasty - Hollywood Golf Stories

Wayne Gretzky’s longtime caddie, Jimmy, joins Tip Your Caddie to drop legendary stories from inside the ropes — from Hollywood icons to golf’s biggest names. Joe Pesci, Jack Nicholson, Clint Eastwood, Sean Connery, and plenty more make their way into Jimmy’s unbelievable tales from the fairways. Plus, he throws down a challenge to Wayne and BizNasty from TNT for an unforgettable golf match.
 
⛳️ Celebrity loops. Caddie life. Hockey meets golf. Jimmy brings stories, laughs, and a challenge The Great One can’t ignore. This one’s all-time.
#tipyourcaddie #golfpodcast #waynegretzky #caddielife #golfstories

Ep. 21 - 14 Years at The Bridge: Wildest Loops Ever

Evan’s been looping at The Bridge for 14 years — and he’s seen it all. From celebrity loops to locker-room rumors, wild member stories, and a love life tangled up in the caddie yard. In this episode, he and his girlfriend sit down to tell the unfiltered truth about what really goes down behind the ropes.
 
⛳️ Topics: Caddie life, dating on the loop, scandalous stories, biggest loops, and The Bridge culture.
🎧 Authentic. Hilarious. Slightly dangerous.
#tipyourcaddie #caddielife #hamptons #golfpodcast #caddie

Ep. 20 - When the Loops End, the Stories Begin

Every caddie knows this feeling — the last loop of the season. The bags are lighter, the days are shorter, and the stories start pouring out like the beers after the final round.
 
In Episode 20, we talk about what really happens when loop season ends — the chaos, the downtime, and the plans that somehow always involve another trip and another bet. 🎲
 
From end-of-season reflections to gambling picks that definitely won’t hit, this one’s all about that in-between zone: when golf slows down, but life doesn’t.
 
This episode isn’t just about caddying — it’s about chasing the next story. Because when the loops end, the real ones don’t stop showing up.
 
So grab a drink, crack a laugh, and hang with the crew one more time before the season fades. 🍻#tipyourcaddie #caddielife #golfpodcast #golfstories #golfcommunity

Ep. 19 - Asia, Loops & Absolute Madness ft. Tarik

In Episode 19 of Tip Your Caddie, we sit down with the legend himself — Tarik.
From private club loops to full-blown adventures in Asia, this one’s got it all:
✅ Wild golf stories
✅ Caddie life overseas
✅ Culture shocks
✅ Absolute madness
 
Whether you're in the yard or the clubhouse, you're gonna want to hear this.
 
🔔 Subscribe for more caddie chaos, golf deep dives, and real-ass conversations.
 
👇 Drop your favorite moment in the comments — especially if you've caddied abroad. #tipyourcaddie #golfpodcast #caddielife #golfstories #asia

Ep. 18 - NFL Week 2 & SPINZ: Kissing the Season Goodbye

It’s the end of loop season, and we’re kicking off something new…
Introducing the first annual Tip Your Caddie SPINZ tradition — our way of saying goodbye to summer with NFL Week 2 bets and a spin through the online casino chaos.
This episode’s got football picks, slot machines, end-of-season emotions, and enough degeneracy to make a bookie blush.
 
🎰 Welcome to SPINZ — where the bets are bad and the vibes are elite.
#tipyourcaddie #nflweek2 #FirstAnnualSPINZ #DegenerateSeason #caddielife

Ep. 17 - When Caddie Life Goes Off the Rails ft. Cheese

Welcome to Episode 17 of Tip Your Caddie — and trust us, this one’s different.
 
Cheese pulls up with hands-down the wildest caddie story we’ve ever heard. It’s got everything: chaos, characters, unbelievable moments, and a whole lot of laughs. If you’ve ever looped a day that made you question reality... this one’s for you.
 
We get into:
 
Cheese’s most outrageous bag yet
 
What happens when a bag goes totally off the rails
 
The kind of story you only hear in a caddie yard
 
Why we do it anyway
 
If you’ve ever tipped a caddie, been a caddie, or just love wild golf stories — hit play.
 
⛳️ COMMENT your wildest loop story
🎧 SUBSCRIBE for more madness from the yard
💰 Tip Your Caddie. Carry Greatness.
#tipyourcaddie #caddielife #golfpodcast #looper #golflife

Ep. 16 - NFL Picks, Looper Life & Degenerate Stock Talk

Tip Your Caddie Ep. 16
NFL season is here and we’re firing off picks like we know what we’re doing (we don’t). This week we break down our best bets, worst ideas, and the wild world of caddie life in peak season.
 
We talk about a week full of loops, some stock moves that might make you rich or ruin your weekend, and why caddying during football season hits different. Plus a few laughs, bad beats, and classic “tip your guy” moments.
 
Drop your LOCK of the week in the comments. If it hits, we’ll shout you out next episode.
Sub if you like golf, gambling, and greatness. We’re building something special here — don’t miss it.
 
⛳️ Loop Season forever
💸 Bet responsibly… or don’t
📈 This is NOT financial advice (but it might be hilarious)
#tipyourcaddie #nflpicks #caddielife #golfpodcast #sportsbetting

Ep. 15 - Footballers Golfing, Degenerate Bets & The Battle of August

Tip Your Caddie Ep. 15
The boys are back with a wild mix of stories from the fairways and beyond.
 
We kick things off with some hilarious takes on footballers trying to play golf (spoiler: not all athletes can stripe it). Then it’s straight into the chaos of August in the Hamptons — loops, heatwaves, and survival mode on the bags. Toss in a few degenerate bets, some stock picks we absolutely don’t recommend following, and a couple of classic golf stories you won’t believe.
 
If you’ve ever caddied, played hungover, or bet the over on a hunch… this one's for you.
 
Hit that like button, subscribe, and drop a comment with your funniest golf story or worst bet.
 
⛳️ Loop Season never ends.
📈 Bet responsibly-ish.
🍺 Spiked Ade collab soon?
#tipyourcaddie #football #funnygolf #caddielife #golfpodcast

Ep. 14 - Hamptons Caddying & Blackout in the Bahamas ft. Tom

Tom joins Tip Your Caddie for one of our funniest episodes yet — packed with wild caddie stories, travel chaos, and unforgettable moments. From hilarious member-guest events to a day at Trump Bedminster, this one’s full of insider golf tales you won’t hear anywhere else.
 
We also get into the infamous blackout in the Bahamas, what really goes down when the drinks start flowing, and the kind of behind-the-scenes moments that make the caddie life so unpredictable. If you’ve ever wondered what it’s like to work at the highest levels of golf, travel with characters, and collect stories that get better every time you tell them — this is your episode.
#golf #podcast #golfpodcast #caddielife #tipyourcaddie #trumpbedminster #golflife

Ep. 13 - The Boys Are Back - Lucas & Jose Unfiltered

Lucas and Jose are back... and somehow even more unhinged. In Part 2 of their Tip Your Caddie takeover, we dive deeper into the chaos of caddie life — from ridiculous loops to the weirdest things we’ve seen on a golf course.
 
If you liked the first one, buckle up — this one’s louder, looser, and way less filtered.
 
Tip Your Caddie Podcast Ep. 13 – real caddie stories, dumb jokes, and maybe a little wisdom if you squint.
#tipyourcaddie #caddielife #golfpodcast #golfstories #golfvibes