Tip Your Caddie

Hailey Ostrom turned pro at 16 — not by choice. Someone ratted her out to the USGA for accepting too much Nike gear, forcing her to turn professional early… and the very next day she made a hole-in-one on the 16th at TPC Scottsdale. In this episode of the Tip Your Caddie Podcast, Doug sits down with pro golfer and content creator Hailey Ostrom (@haileyostrom) — fresh off Doug caddying for her at The Bridge — to talk about growing up in the hidden golf mecca of Bend, Oregon, playing D3 golf, grinding the Cactus and Symetra Tours, and pivoting to become one of golf's biggest creators during COVID. Plus: playing a LIVE Pro-Am with Caitlyn Jenner, the time she shook President Trump's finger, her 3x-Olympian snowboarder husband, and her invite to the $4 million Internet Invitational.

🎙️ The Tip Your Caddie Podcast — POWERED BY SPIKEDADE.
CHAPTERS 00:00 Intro — new studio, meet Hailey Ostrom
00:22 Caddying for Hailey at The Bridge
00:46 Her top 3 golf courses of all time
02:26 Growing up in Bend, Oregon — a hidden golf mecca
03:41 Her dad & when golf "wasn't cool"
04:20 D3 golf at George Fox (and why she loves D3)
05:22 Turning pro: Cactus Tour & Symetra
05:57 Ratted out to the USGA at 16
07:45 Hole-in-one at TPC Scottsdale the next day
09:12 The COVID pivot to social media
11:22 The phantom heavy bag & meeting Doug
6:15 Favorite YouTube golf collabs
16:45 Playing a LIVE Pro-Am with Caitlyn Jenner
21:08 The $4 million Internet Invitational invite
25:01 Dream teammates (Justin Gaethje?!)
27:44 Should YouTube golf bring in caddies?
31:03 Meeting President Trump at Bedminster
33:45 "I shook his finger"
36:43 The "Caddy Daddy" story
38:48 Her husband — 3x Olympian snowboarder
42:18 Snow golf on snowboards
43:18 Her on-course philosophy
49:46 Last Call
53:08 Who's on next?

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🎙️ TIP YOUR CADDIE — EP. 36 | Nate Scott Darren Clarke handed Nate Scott the putt to win the American Family Insurance Championship — the first read Clarke had asked him for all week. Nate said two words: "straight putt." Clarke buried it dead center, fished the ball out of the hole, and handed it to him — "Great read, Nate." It was Nate's first career win. Nate is one of the youngest caddies on PGA Tour Champions, and after five years grinding on the Korn Ferry Tour and looping at TPC Sawgrass, he got his breakthrough on Ben Crane's bag — teamed with Open champion and Ryder Cup captain Darren Clarke and his caddie Keith Nolan. But the road there was anything but straight. Nate walks Dougie through the whole ride: caddying for his college roommate Chandler Blanchett, a 24-hour drive to Winnipeg for his first pro loop, quitting sales, surviving the brutal Stadium Course at Sawgrass (where he says he's seen maybe 10 people break 80 in five years), four years and a million miles with Thomas Walsh, and a rocky start with Ben Crane that — between a missed cut and snapping his new boss's driver clean in half — probably should've ended his run before it began. Ben's response is one of the best moments in the episode. Then there's the win itself: Clarke's fire-up speeches ("no sorrys this week — we're trying our nuts off"), Ben Crane catching absolute fire on the greens and putting the team into the record books, a white-knuckle Sunday in 20 mph Wisconsin wind, and that final putt on 18. In this episode: How a college favor turned into a pro caddie career The nine-missed-cuts-in-a-row stretch that got him fired — by his best friend Why TPC Sawgrass is the hardest loop in golf The rocky start with Ben Crane that nearly ended it before it began Reading Darren Clarke's winning putt — and the game ball that came with it AimPoint, life as the "young buck" on the senior tour, and the Last Call Real caddies. Amazing stories. Built from the bag up. 👉 Subscribe and join the movement — and check the latest hat drops for The Yard and The Loop: https://tipyourcaddie.com/ Last Call poured by SpikedAde 📲 Follow: @TipYourCaddie IG | TikTok @tipyourcaddie Nate Scott — https://www.instagram.com/808andnate/ #tipyourcaddie #CaddieLife #PGATourChampions #DarrenClarke #BenCrane

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 on the bag at one of the most iconic courses in the game. Wild loops, what it takes to read those greens off Lake Michigan, the stuff that never makes the timeline, and the kind of insider advice that'll make your own caddie glad you walked up. Real golf, no filter, straight from the bag room. #tipyourcaddie #golfpodcast #whistlingstraits #caddielife #interview

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 New Zealand.

In this episode of the Tip Your Caddie Podcast, Doug sits down with Dillon (@dillongarcia) to talk about falling into resort caddying after a broken leg, what Cabot Citrus Farms is really like now that the old World Woods is unrecognizable, the caddie life at Cabot Cape Breton (Links vs. Cliffs), and why he's chasing summers in Nova Scotia and a full year at Tara Iti in New Zealand. Plus: caddie pet peeves, the best chirps in the yard, and the Last Call.

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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 Channel's Round Trip, now founding Fire Pit Productions and serving as Chief Storyteller at Kemper Sports, Matt's the rare golf-media figure who treats caddies the way TYC treats them: as the people the game is actually built around.

In Episode 33, Dougie Buckets and Matt go deep on the loopers who shaped his career, the caddie academies giving kids a real path into the game, the philosophy of taking a caddy in a world that's increasingly built for carts, and the single best caddie call Matt has ever heard — on the 18th tee at St. Andrews, in the wind, with a re-tee already in the burn behind him. Plus: how Matt's son ended up with the name Bandon, why caddies make the best tour guides anywhere outside the ropes, and the white whale of golf media that Matt has agreed to help us land.

Stick around to the end for "Last Call" poured by SpikeAde

GUEST

Matt Ginella — Founder, Fire Pit Productions · Chief Storyteller, Kemper Sports

Instagram: @mattginella

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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 Network — and as it turns out, a serious caddie guy.

Doug and Trey get into the unionization fight at Pebble Beach, the loopers and courses that defined Trey's golf life (Pebble, Spyglass, Bandon, Sand Valley, St. Andrews, Carnoustie), the best caddie advice he's ever been given, the boys-trip moments he'll never forget, and what it actually took to walk away from ESPN and build something of his own.

If you care about caddie culture, this is the one

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GUEST Trey Wingo — The Wingo Network ⭐

/ trey.wingo

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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 joins us for an honest and entertaining conversation covering Pebble Beach stories, boys golf trips, psychedelic mushrooms, bold new golf league ideas, union talk, and the future of YouTube Golf.

This episode is packed with fresh perspectives and inside golf talk you don’t hear everywhere.

We cover:

• Pebble Beach stories and secrets

• Boys golf trips & unforgettable memories

• Mushrooms and golf

• Game-changing new golf league ideas

• Golf union talk

• The current state and future of YouTube Golf

If you love real golf conversations, behind-the-scenes stories, and new ideas for the game — this episode is for you.

Powered by Spiked Ade — “Because we need one.”

Subscribe to Tip Your Caddie for weekly podcasts, raw golf stories, and the side of the game most people never hear about. For the ones carrying the game.

#tipyourcaddie #pebblebeach #golfpodcast #youtubegolf #golfleague

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 of the guys looping on LIV — to talk about the moment everything changed. They were at a tapas restaurant in Mexico when the news hit. Their jobs were potentially in jeopardy. Ten minutes earlier, life was normal. Ten minutes later, nobody had answers.

This one goes places most LIV coverage won't. No talking points. No corporate spin. Just caddies who've lived inside both worlds talking honestly about what comes next.

From the £5 tip at Queenwood… to Augusta dreams, Riviera nerves, and a phone call from mom that nobody saw coming.

What's in the bag this week:

The LIV uncertainty — what they actually heard, and when

Inside the LIV locker room the night the news broke

What happens to caddies if LIV folds back into the PGA Tour

The £5 Queenwood tip that gave this show its name

A Maidstone loop that ended in three holes of silence

The Mexico encounter with an Augusta member nobody saw coming

Hong Kong, a tied-second, and the moment Ricey will never forget

A first look at Caddy Clubhouse — building the future of caddy work

Augusta: the last loop they'd ever take

If you've followed LIV from the outside but never heard from the guys actually carrying the bags out there… this is the episode.

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For the ones carrying the game.

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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, massive tips, absolute horror stories out on the grass, unforgettable loops, and the best moments he's had with players over the years.

From dream rounds… to complete disasters.

This episode is pure caddie yard storytelling:

Huge tips & unbelievable members

Horror stories from the course

The reality of looping at Whistling Straits

Funny player moments

Golf personalities behind closed doors

The best parts of caddie life

How golf content is changing the game

If you’ve ever carried a bag, worked in golf, or just wondered what REALLY goes on inside the ropes… this episode is for you.

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“Because we need one.”

Subscribe to Tip Your Caddie for weekly podcasts, golf stories, and the side of golf most people never hear about.

For the ones carrying the game.

#tipyourcaddie #caddie #golfpodcast #whistlingStraits #golf

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 the most iconic golf destinations in the world. From wild stories on the bag to dealing with all kinds of players, this episode dives into the side of golf most people never see.

If you’ve ever carried a bag, thought about caddying, or just love the game—this is your episode.

Tip Your Caddie is about the stories, the people, and the culture behind the game. We’re here to elevate caddies and the ones who make the game what it is.

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Send in your caddie stories (anonymous or not)—we might feature it on the podcast.

#tipyourcaddie #golfpodcast #bandon #caddie #golfcontent

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, the wildest things they've seen on that tee box, what The Players week is actually like from inside the ropes, and the loops they'll never forget.

No filters, no PR answers. Just the guys who've been watching the splashes, reading the putts, and carrying the bags at the most famous stadium course in golf.

Grab a drink, pull up a chair, and tip your caddie.

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🎧 Tip Your Caddie Podcast — new episodes weekly.

👕 Shop TYC → tipyourcaddie.com/collections

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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 the caddie world — how he got started, how he stuck around, and how he somehow ended up caddying for celebrities, pro athletes, and even fist-bumping Donald Trump along the way.

We get into baseball stories, clubhouse chaos, and the real behind-the-scenes life of a career caddie — plus plenty of unplanned moments, including a pizza delivery mid-pod and a banner falling on my head (yes, seriously).

This one’s about the relationships, the randomness, and the kind of stories you only hear in a caddie yard.

If you’ve ever wondered what really goes on off the scorecard, this episode is for you.

Subscribe for more caddie stories, chaos, and conversations you won’t hear anywhere else.

#tipyourcaddie #golfpodcast #caddielife #golfstories #fistbump

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 Carnoustie, St Andrews, and then flying straight to Bandon Dunes. Lucas is fresh off a long stay back home in Kentucky with stories of his own…

And then Kon shows up out of absolutely nowhere for his first appearance in YEARS.

This episode has everything:

• Caddie life updates after weeks away

• UK + Scotland golf stories from the bucket-list courses

• Behind-the-scenes from Bandon Dunes

• Why Lucas disappeared to Kentucky

• Kon popping in unannounced

• Impressions, chaos, and Miami energy

If you love golf, caddie stories, travel adventures, or just unfiltered conversations that go off the rails… you’re gonna love this one.

#golfpodcast #caddielife #tipyourcaddie

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

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

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

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

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

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

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💰 Tip Your Caddie. Carry Greatness.

#tipyourcaddie #caddielife #golfpodcast #looper #golflife

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