A show about nothing...and...everything at the same time. A podcast that connects, sharing learned experiences drom different perspectives through thoughtful dialogue and organic wit and truth. Each episode starts with a cookie from Whiskey Brown and is paired with bourbon, scotch or whiskey. What ensues is a genuinely improvised and authentic conversation laughter and newfound knowledge, insight and respect over Whiskey with a Buddy.
S2:E4 The Importance of Being Earnest ... About Red Flags
Glenfiddich 15, Dark Matter Cookies, and the Judge’s Red Flags
Whiskey Brown and Buddy Robinson catch up on Whiskey With a Buddy, promote whiskeybrown.com cookies, and taste Glenfiddich 15-year single malt, rating it around 8.5–8.7 while pairing it with Whiskey Brown’s Dark Matter salted bourbon caramel chocolate cookie topped with spicy flakes and Portuguese fleur de sel. They discuss missed guest plans with the “kombucha lady,” recent cookie deliveries and gaining podcast followers, and plans for a future cocktail party. Whiskey Brown recounts ongoing, complicated dating with “the judge” (a former judge now practicing estate-planning-related law), including her backpedaling after drinking, two “red flags” she raised, and canceling a planned Sunday brunch for golf. They play a drinking trivia card game, struggle through questions, and end the episode with closing plugs for the podcast and cookies.
23 Sept 2026
S2E3: A Whiskey Runs Through It
Buffalo Trace Barrel Pick vs. Standard, Mint Julep Cookies, and Wisco Bourbon’s Story
Whiskey Brown hosts an episode of “Whiskey with a Buddy” without Buddy, joined by returning guest Josh Charleston of Wisco Bourbon LLC, which grew from a 2020 Facebook club into a business with about 13,000 group members and nearly 20,000 followers across platforms. Josh brings a Wisco Bourbon Buffalo Trace barrel pick selected in Kentucky from remaining barrels in a 36-barrel drawing; the pick is aged eight years, nine months, and bottled at 90 proof, while the standard Buffalo Trace is described as a six-to-seven-year small-batch product. They compare both, describing the regular as sweet and caramel-forward (rated about 6.5) and the barrel pick as more complex with cinnamon heat (rated about 7.5–7.9). They eat a “May the Horse Be With You” mint julep chocolate bourbon cookie, discuss allocations and pricing, travel plans (including Banff), future cookie collaborations, and play “Soul Trivia: Who’s Blacker?” before closing with plugs for whiskeybrown.com and Wisco Bourbon.
18 Sept 2026
Coffee Talk: Much Ado About Everything
Coffee Talk: Telluride Recap, Family Updates, and Life Check-Ins
In this informal “Coffee Talk,” Whiskey Brown and Buddy catch up with no agenda, starting with small talk about haircuts, hats, and coffee shops before Whiskey recounts an 11–12 day Telluride trip centered on Butcher and the Baker, hiking (including the steep Telluride Trail), and the Film Festival atmosphere, where he saw Yo-Yo Ma play in Town Park and spotted celebrities like Jesse Eisenberg, Paul Giamatti, and Julianne Moore, plus heard about Bill Gates’ AI talk. He discusses making local connections (poker, tennis), a tense encounter with a stranger, and concerns about house security and missing keys after a property manager change. They share family updates: Lily’s Wharton activities and Antarctica trip, Willow apartment-hunting, Margot nearing graduation and job searching, and Stella planning to ED to Tulane. They also touch on therapy, podcast distribution/analytics, upcoming visits and dinner plans, and sports chatter.
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
Apple Podcasts (US)
5.0 / 5
5 ratings
Podcast Authority Score: 34 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
56
Social presence
0
YouTube
0
Engagement
32
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