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? 👕 Shop TYC: tipyourcaddie.com/shop ▶️ Join Us: [link] tipyourcaddie.com/join 📲 @tipyourcaddie | Guest: @haileyostrom #TipYourCaddie #Caddie #HaileyOstrom #Golf #GolfPodcast #InternetInvitational #WomensGolf #LIVGolf

🎙️ 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

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

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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 ⭐

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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.

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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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