Inside Chewy’s Lounge: Tampa’s Ultimate Music and Cigar Venue

On this episode of Smoke Dogg’ Cigars presents Puff, Sip, Chat join Reggie Kimble at Chewy’s Lounge in Tampa for a candid conversation with Chewy and Stuart about building a live music venue rooted in Tampa’s cigar and music culture. Get the inside scoop on what makes Chewy’s different—and what it takes to run a business with friends. • The origin story and unique vibe of Chewy’s Lounge • Challenges and honesty in business partnerships • How live musicians and auditions are curated for the venue • Integrating cigars, music, and bar culture in Tampa • The long-term vision for Chewy’s Lounge and what guests can expect Chapters 00:00 Introduction to Chewy's Lounge 04:37 Meeting Stu and his influence 08:02 Forming a business partnership 10:51 Auditioning new band members 14:54 The value of live music 16:44 Stu's AI music request 20:02 Challenges of Cigar Retail Business 25:18 Expanding weekly music events 26:42 Struggling at early jam sessions Support the show