Episodes

  • Ep. 34 - From a Food Truck to Cabot Citrus Farms ft. Dillon Garcia
    Jun 11 2026

    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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    47 mins
  • Ep. 33 - Matt Ginella aka 40 Caddies, One Phone
    Jun 4 2026

    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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    1 hr and 9 mins
  • Ep. 32 - Trey Wingo on Pebble Beach - The Caddie Union & Life After ESPN
    May 28 2026

    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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    Stick around for the Last Call poured by SpikedAde.

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    #tipyourcaddie #treywingo #caddie #pebblebeach #golfpodcast

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    47 mins
  • Ep. 31 - Pebble Beach, Mushrooms & The Future of YouTube Golf
    May 23 2026

    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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    #tipyourcaddie #pebblebeach #golfpodcast #youtubegolf #golfleague

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    1 hr and 8 mins
  • Ep. 30 - LIV Golf Insiders Only - Caddies Stick With Their Guy
    May 14 2026

    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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    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.

    🎧 Tip Your Caddie Podcast — new episodes weekly

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    #tipyourcaddie #LIVgolf #caddielife #golfpodcast #caddie #PGATour #golf

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    1 hr and 6 mins
  • Ep. 29 - Good Good or Dude Perfect? Who Tips Better? - Inside Whistling Straits
    May 7 2026

    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

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    59 mins
  • Ep. 27 - Sawgrass Caddies Reveal the Secrets of 17 - Crazy TPC Stories
    Apr 17 2026

    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.

    🎧 Tip Your Caddie Podcast — new episodes weekly.

    👕 Shop TYC → tipyourcaddie.com/collections

    🤝 Join The Loop → tipyourcaddie.com/join

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    44 mins