LS Episode 526: Confidence Hits Different (feat. Connie Diiamond & Leela James)

Connie Diiamond and R&B legend Leela James join Angela Yee for a raw and honest conversation about confidence, growth, and life in the industry. From navigating love and forgiveness to balancing motherhood, music, and self-worth, this episode dives deep into what it really takes to thrive as a woman in entertainment. Leela reflects on 20 years in the game, her evolution since R&B Divas, and the meaning behind her new single “Right On Time.” Connie opens up about Underdog Season 2, finding her voice through vulnerability, and why being real will always outshine being perfect. The ladies also get candid about marriage, independence, social media pressure, and the blurred lines between talent and popularity in today’s industry. Plus, they share wild early hustle stories and some hilarious dating drama that’ll have you cracking up. Whether you’ve been following Leela’s soulful journey or Connie’s New York come-up, this one’s full of gems, laughter, and truth. Chapters:00:00 – Intro & Energy Check01:05 – Leela Reflects on 20 Years in Music02:17 – Connie Diamond on Forgiveness & Staying Real03:47 – Vulnerability & Industry Challenges06:20 – Reality TV & Finding Authenticity09:50 – The Story Behind “Right On Time”11:22 – Marriage, Divorce & Clingy Love15:25 – Dating in the Industry19:31 – Motherhood & Taking Breaks from Music22:13 – Recording Energy & Location Vibes26:00 – How the Industry Has Changed30:11 – Talent vs. Popularity34:08 – Early Hustles & Funny Odd Jobs37:20 – Crazy Dating Stories & Red Flags43:04 – Money, Gender Roles & Independence49:00 – Does the Past Define You?53:36 – Confidence vs. Insecurity56:00 – Creative Process & Artistic Pressure58:38 – Closing Thoughts on Legacy & GrowthSee omnystudio.com/listener for privacy information.