Flyana Boss sit down for a wide-ranging conversation about ageism in rap, Teezo Touchdown & Tyler, the Creator, Missy Elliott defending them on Twitter for their viral "running" marketing campaign, building a career without industry permission, their futuristic aesthetic, the importance of whimsy, cats, the Grateful Dead, and much more.Make sure you hit that follow button & leave a comment letting us know what you thought about the show. 00:00 How Flyana Boss Met at Music School1:30 Moving to LA to become stars3:40 Tyler the Creator & Teezo Touchdown14:13 Eyrkah Badu 16:30 Family & Upbringing19:30 First Musical Influences21:30 Building their Futuristic Aesthetic22:50 Missy Elliott Defending Them On Twitter for Running & Viral Marketing29:00 Selling Weed & Working Before Breaking Through 30:30 Are Artists Ever Too Old To Be Creative?42:00 Leaving Their Label & Going Independent 50:00 What It Takes to Break Through Today57:30 Unpopular Truth1:03:28 Lightning Round1:08:30 What's nextShout out to https://www.gold-diggers.com for hosting the show!
Flyana Boss: Going Viral, Missy Elliott, Twitter Controversy, Label Drama & Ageism in Rap
Jan 27, 2026
The Truth Hurts w/ Jeff Weiss, Rosecrans Vic and Free
The Truth Hurts is the antithesis to hip-hop podcasts dedicated to shameless clout-chasing and nihilistic exploitation. Instead of contrived drama and sinister gossip, the show seeks to chronicle the stories and lives of America's most compelling artists. It features journalists who've been embedded for years in the West Coast scene, but covers topics and personalities impacting popular culture at large. Each week, hosts Jeff Weiss, Rosecrans Vic & Free sit down at Pro Club in LA with musicians to break down their art, life and career from an honest, unflinching, music-first perspective.
The Truth Hurts is the antithesis to hip-hop podcasts dedicated to shameless clout-chasing and nihilistic exploitation. Instead of contrived drama and sinister gossip, the show seeks to chronicle the stories and lives of America's most compelling artists. It features journalists who've been embedded for years in the West Coast scene, but covers topics and personalities impacting popular culture at large. Each week, hosts Jeff Weiss, Rosecrans Vic & Free sit down at Pro Club in LA with musicians to break down their art, life and career from an honest, unflinching, music-first perspective.Listen on
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