Tip Your Caddie

Ep. 35 - Looping at Whistling Straits ft. CaddieTales | Tip Your Caddie

Some loops you never forget. Mark caddies at Whistling Straits — and he's got the stories to prove it. This week we're joined by the man behind CaddieTales, talking life

Ep. 34 - From a Food Truck to Cabot Citrus Farms ft. Dillon Garcia

Dillon Garcia went from running a pancake food truck to caddying at Cabot Citrus Farms — and two years later he's looping his way around the world, from Nova Scotia to Ne

Ep. 33 - Matt Ginella aka 40 Caddies, One Phone

Matt Ginella has spent decades around the best courses in the world — and around the people carrying the bags at them. From Sports Illustrated to Golf Digest to Golf Chan

Ep. 32 - Trey Wingo on Pebble Beach - The Caddie Union & Life After ESPN

Trey Wingo joins Dougie Buckets, confirmed the biggest guest in Tip Your Caddie history. 23 years at ESPN, two decades as the voice of NFL Sundays, now running The Wingo

Ep. 31 - Pebble Beach, Mushrooms & The Future of YouTube Golf

What does the future of golf actually look like? And what really happens behind the scenes at Pebble Beach? This week on Tip Your Caddie, Tim Palmer from Looper Talk joi

Ep. 30 - LIV Golf Insiders Only - Caddies Stick With Their Guy

What happens to the caddies when the tour they work for might not exist next year?   This week on Tip Your Caddie, we sit down with Adam, Jonathan and "Ricey" — three o

Ep. 29 - Good Good or Dude Perfect? Who Tips Better? - Inside Whistling Straits

What REALLY happens out on the golf course after the members leave?   This week on Tip Your Caddie, we sit down with Mike The Caddie to talk life at Whistling Straits,

Ep. 28 - Inside Bandon: The Loops Locals Don't Talk About

Inside Bandon Dunes with caddie Mason Shamion—this one’s for the caddies and the guys who get it.   We sat down to talk about what it’s really like looping at one of th

Ep. 27 - Sawgrass Caddies Reveal the Secrets of 17 - Crazy TPC Stories

The island green. The roars. The carnage. We pulled up a couch with the caddies who loop TPC Sawgrass and asked them everything — how many balls you really need for 17, t

Ep. 26 - How a Caddie Became the Fist Bump King

From pizza deliveries to fist-bumping a president.   In this episode of the Tip Your Caddie Podcast, we sit down with Pistol Pete to break down his 10-year journey in t

Ep. 23 - Lucas Is Back, Kon Pulls Up - Miami Reloaded

The boys are officially BACK. Episode 23 of Tip Your Caddie might be the wildest one we’ve filmed in a long time.   Doug returns from an insane overseas run — playing

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, J

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

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 fina

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 g

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

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 eve

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 th

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

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 eve