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.

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.

Whiskey Brown and Buddy Robinson open season two of “Whiskey with a Buddy,” joking about cookies, therapy, neediness, and the show’s “bumper,” then preview topics like breakups, heartache, and a vasectomy before eating a gluten-free “Big Friendly Giant” monster cookie (peanut butter cups, oatmeal, toffee, caramel, kettle chips, popcorn, sunflower cups, candy pieces) and day-drinking scotch. They compare Glenmorangie (smooth, citrus notes) with Oban (peatier, spicier) and discuss how modern culture mishandles endings, including ghosting, as Buddy recounts an employee quitting without notice and his feelings of failure. Whiskey shares insecurity around feedback, shipping/packaging causing cookies to arrive dry, and learning not to take things personally, then they play Soul Trivia and banter about slang, race, and repeated cards.

Whiskey Brown launches season two of “Whiskey With a Buddy” with guest Michelle Bryant, host of WNOV’s “Say Something Real,” as they share their playful, long-running friendship while sampling a bourbon vanilla bean sugar cookie called “Tiny Tim” (a Whiskey Brown cookie originally named for A Christmas Carol) and sipping Willett bourbon. Brown walks Bryant through a basic whiskey tasting framework (appearance/color, smell, taste, complexity) and discusses whiskey color, barrels, proof, and aging, including Bryant’s preference for Macallan 25. Bryant describes her 20+ years in politics and community work, recounts early canvassing that led to a new playground, and summarizes her column criticizing NFL player Saquon Barkley’s highly visible association with the president, arguing politics and sports are inseparable and citing issues like Kaepernick and racial inequities in the league. They end with “Soul Trivia,” joking about who is “Blacker,” and close with banter and a brief singalong.