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Many people I’ve spoken to have had an eventful start to 2025, but few have experienced as much change as Giles Cooke of Thistledown Wines. Recently, Thistledown parted ways with Alliance Wines—a bold move that, for Giles, felt like the right timing. A self-professed contrarian, he thrives on zigging while others zag, and the results often speak for themselves.

Beyond his latest venture, Giles was kind enough to offer me some feedback on a recent project of mine, which sparked the idea to bring him back on the show. Given his deep expertise in marketing and market strategy—both areas he’s incredibly passionate about—it felt like the perfect opportunity to tap into his insights.

Despite a minor connection glitch, we pulled together what I hope is an engaging and thought-provoking conversation. A huge thank you to Giles for joining me!

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