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Brian Bailie, GolfCask | Episode No. 499

·1 hr 18 min·4 clips
Brian says GolfCask is about slowing down, putting phones in a burlap bag, and spending an hour on whiskey, cigars, and conversation.
1. The Wednesday Match Play Podcast episode centers on Brian Bailie and GolfCask, a brand built around golf, whiskey, cigars, and travel. 2. Brian Bailie is the founder of GolfCask, a golf coach by trade, and the guest explains why his background in college coaching and sports data led to the company. 3. The episode asks what happens when golf, whiskey, cigars, and travel are turned into a community instead of separate hobbies. 4. Brian says GolfCask started on a golf trip in Ireland, inside a snug where he and friends were drinking whiskey and smoking cigars with golf school participants. 5. He says that moment made him ask why he was not doing that experience for a living. 6. Brian identifies five pillars for GolfCask: golf, whiskey, cigars, travel, and community. 7. He explains that he wakes up every morning researching cigars, whiskey, and golf as part of the business. 8. Brian says COVID was his major entry point into whiskey because lockdown led him to buy different bottles, make cocktails, and then start drinking whiskey neat. 9. He argues that whiskey keeps grain flavor in a way vodka does not, and he says gin is usually out for him because he hates juniper. 10. Brian names several go-to bottles and distillers, including Devil’s Dew in West Virginia, Wild Turkey Rare Breed, Pipe Dream, Leopold Bros., and John Lane’s Cask Strength. 11. He says he prefers complexity, blind tastings, and new bottles over repeating the same familiar pour. 12. Brian gives examples of whiskey prices, saying most of his bottles cost $50 to $100, while one bottle in Ireland cost about $250. 13. He says he would rather drink bourbon than collect unopened bottles, and he describes opening bottles for friends instead of treating them like investments. 14. Brian says the GolfCask interactive map is being built to help people find golf courses, distilleries, cigar lounges, and pubs anywhere in the world. 15. He says the map covers roughly 15,000 golf courses and more than 3,000 distilleries in the U.S., with member ratings shaping the recommendations. 16. Brian describes the GolfCask lifestyle as slowing down, putting phones in a burlap bag, and spending time on whiskey tasting, cigars, and conversation. 17. He says the format is intentionally social and reflective because he wants people to be present with one another instead of scrolling. 18. Brian explains his certified bourbon steward designation as Tennessee training that covers tasting notes and the process from grain to bottling. 19. Listeners who like golf coaching, whiskey culture, and cigar-community ideas will get the most from this conversation. 20. Listeners seeking pure swing instruction or hard technical product reviews may skip this one.

As heard by us

A golf-lifestyle chat about GolfCast, with golf, whiskey, and cigar culture held together by a steady push to slow down and be present.

Wednesday Match Play presents this episode as a golf-lifestyle conversation built around GolfCast, where golf, whiskey, and cigar culture sit close together.

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Why you'd press play

Press play when you want golf talk that slips into whiskey, cigars, and a quieter hour.

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