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