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