Jon Wolfe On “Barstool Therapy (Session One)” And Building Juan Lobo Tequila

Texas country singer Jon Wolfe is leaning hard into classic honky-tonk on “Barstool Therapy (Session One)” while juggling life as a tequila brand founder.

Jon Wolfe breaks down “Barstool Therapy (Session One)” and his Juan Lobo Tequila brand

NASHVILLE, Tenn. — November 8, 2025

What Happened

Texas-based country singer Jon Wolfe joined Talk of the Town to unpack his new album “Barstool Therapy (Session One)” and explain how his traditional-leaning project connects with his growing tequila line, Juan Lobo Tequila. Over the course of the conversation, Wolfe walked through each track, his writing trio, and the long road from finance and oil to honky-tonks and agave fields.

Key Details

Album concept: Wolfe describes “Barstool Therapy (Session One)” as a return to his earliest influences, channeling the classic Merle Haggard and Hank Jr. end of his musical DNA while still living firmly inside traditional country.
Emotional tone: He says this is one of his more vulnerable records, leaning into personal themes and the challenge of showing more of who he really is after 15 years of releasing music.
Writing trio: Most of the album was crafted by a small creative circle: Wolfe, producer Dave Brainard, and songwriter Tony Ramey, who write together in a relaxed “hang” environment that sometimes includes tequila and long conversations rather than formal Nashville co-writes.
Standout tracks: Songs like “The Older I Get (The More Country I’m Getting to Be),” the title track “Barstool Therapy,” “Tequila Cowboys,” “One of Those Things,” “Back in the Glass,” “I Don’t Drink Anymore,” and “Wherever the Wind Blows” each highlight different sides of Wolfe’s storytelling and production.
Sound design: The record leans into detailed, cinematic touches, including beer can pops, barroom ambience, Spurs and arena sound for “Tequila Cowboys,” piano intros, and even seagulls on the closing track to visually place listeners inside each scene.
Tequila brand: Wolfe started developing Juan Lobo Tequila around 2016–2017, launched it in Texas in late 2019, and has spent years building relationships with producers in Jalisco, Mexico to create a 100% blue agave tequila he believes in.
Session Two plans: A second installment is already in the works, likely as a broader deluxe edition with a western swing cut featuring the Time Jumpers and a legendary Texas singer, a classic country cover, and Juan Lobo’s first theme song backed by a San Antonio mariachi band.

Why It Matters

“Barstool Therapy (Session One)” doubles down on a lane Wolfe has occupied for years but pushes it further into classic territory. Instead of chasing radio trends, he is leaning into fiddle-and-steel textures, barroom narratives, and the emotional arc of a full album experience. That choice lines up with a broader shift in country where fans are gravitating back toward more traditional sounds and deeper songwriting, even as streaming singles dominate the charts.

The project also shows how Wolfe is tying together his creative and business lives. The barroom scenes, tequila references, and “therapy session” framing echo his real-world investment in Juan Lobo Tequila, giving him a cohesive brand identity across music, lifestyle, and spirits. It is the kind of multi-lane strategy more independent artists are adopting to build sustainable careers.

Context & Fan Reaction

Wolfe notes that he has been releasing music since 2010, with early records sometimes leaning a bit more modern than this new project. Over that 15-year span, he has built a reputation as a traditionalist whose catalog pairs well with George Strait-style feel-good songs and deeper cuts that reveal more of his life as he grows comfortable telling those stories.

On “Barstool Therapy (Session One),” that evolution shows up in several ways. “The Older I Get (The More Country I’m Getting to Be)” pulls directly from his life in New Braunfels, Texas, swapping sports cars for old pickup trucks and grounding the lyric in family and slowing down. “Tequila Cowboys” was tailored with Randy Rogers in mind, turning a familiar Friday-night bar meetup into a tongue-in-cheek story about good old boys who see themselves as saving the town from their bar stools.

Wolfe also acknowledges how demanding concept records can be. His previous full-length, “Dos Corazones,” was written and recorded in roughly a year and left him unsure what he wanted to say next. Instead of forcing another big concept, he slowly regrouped with Brainard and Ramey, writing songs they simply loved until a new vision started to take shape. “Barstool Therapy” grew out of that slower, more organic process.

ByteSize Commentary

For an artist who once weighed futures in finance, the oil business, fly fishing, and ranch work, Wolfe has quietly built a career that now threads together traditional country, Texas storytelling, and a tequila brand with real roots in Jalisco. “Barstool Therapy (Session One)” feels like the moment those threads fully align.

The record leans into barroom imagery, emotional piano ballads, and little sound-design choices that make each song feel like a scene rather than just another track on a playlist. At the same time, the partnership with Dave Brainard keeps the production from drifting into nostalgia-for-nostalgia’s-sake. It is classic in feel but not a copy of older records.

On the business side, Wolfe is blunt that he underestimated how hard the tequila world would be. Pandemic setbacks, supply relationships, and brand-building have turned Juan Lobo into a long-game project, not just a celebrity label slap. That honesty fits neatly with the album’s theme: life is rarely tidy, but a barstool, a friend, and a well-made drink can help you sort through it.

What To Watch Next

Listeners should keep an ear out for Session Two details, especially the western swing cut with the Time Jumpers and the Juan Lobo theme song with mariachi backing, both of which could widen Wolfe’s musical palette while staying rooted in tradition. Any deluxe edition will also show how he sequences these songs as one larger story, an art he and Brainard clearly take seriously.

On the spirits side, Juan Lobo’s growth will be worth watching as touring ramps up around “Barstool Therapy.” In-room storytelling about the brand, themed events, and targeted Texas and Southwest markets could help tie new music directly to tequila sales. If Wolfe can keep the music-first credibility while scaling the bottle on the bar, he may carve out one of the more cohesive artist-brands in modern country.

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