# “The Empty Cup,” Always the Student  ft. Courtney "Bear" Sills | Conversate with Killer Mike ep. 45

Page: https://stenobird.com/podcast/conversate-with-killer-mike-7439481/the-empty-cup-always-the-student-ft-courtney-bear-sills-conversate-with-killer-mike-ep-45
Text version: https://stenobird.com/podcast/conversate-with-killer-mike-7439481/the-empty-cup-always-the-student-ft-courtney-bear-sills-conversate-with-killer-mike-ep-45.md
Podcast: [Conversate with Killer Mike](https://stenobird.com/podcast/conversate-with-killer-mike-7439481)
Published: 2026-05-20T15:12:00+00:00
Episode link: https://mgln.ai/e/441/pscrb.fm/rss/p/tracking.swap.fm/track/GShUDppPATUMmMhYllkv/traffic.megaphone.fm/IMP8444011872.mp3
Audio file: https://mgln.ai/e/441/pscrb.fm/rss/p/tracking.swap.fm/track/GShUDppPATUMmMhYllkv/traffic.megaphone.fm/IMP8444011872.mp3
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JSON: https://stenobird.com/v1/public/podcasts/conversate-with-killer-mike-7439481/episodes/the-empty-cup-always-the-student-ft-courtney-bear-sills-conversate-with-killer-mike-ep-45
Duration seconds: 5379

## Resource

In this episode of Conversate with Killer Mike, Cutmaster Swiff, and Ashley sit down with Bear, a behind the scenes force who helped shape Atlanta’s music industry from the ground up. From cutting hair in local barbershops to working alongside icons like OutKast, Bad Boy, and some of the biggest names in hip hop, Bear’s story is a masterclass in relationships, timing, and staying solid in a business that rarely rewards it. Bear breaks down how the barbershop became a gateway into the industry, why integrity and character matter more than talent, and what it really took to build artists like 112 from the ground up. The conversation moves through Atlanta’s rise, the reality of New York’s grind, and the lessons learned from being in rooms with legends like Biggie, Puff, and Eminem. They also get personal, diving into fatherhood, discipline, martial arts, and how Bear Strong Inc. is giving back to the next generation through health, wellness, and community work. This is a conversation about legacy, humility, and what it means to play your role at the highest level without needing the spotlight. For more information on Bear Strong, Inc, please visit www.BearStrongnp.org/ Follow Bear Strong, Inc on Instagram @bearstrongnpo Conversate with Killer Mike is a Third Story Media production.biz: ConversatewithKillerMike@rightclick.gg Subscribe to Conversate with Killer Mike on YouTube: http://www.youtube.com/subscription_center?add_user=KillerMikeGTO Conversate with Killer Mike on IG: https://www.instagram.com/conversatewithkillermike/ Conversate with Killer Mike on TikTok: https://www.tiktok.com/@conversatewithkillermike Subscribe to Killer Mike on YouTube: http://www.youtube.com/subscription_center?add_user=KillerMikeGTO Learn more about your ad choices. Visit podcastchoices.com/…

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