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

Angela Yee's Lip Service

iHeartPodcasts

Comedy, Relationships, Society & Culture

4.6 • 4.1K Ratings

🗓️ 4 November 2025

⏱️ 72 minutes

🔗️ Recording | iTunes | RSS

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Summary

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 Check
01:05 – Leela Reflects on 20 Years in Music
02:17 – Connie Diamond on Forgiveness & Staying Real
03:47 – Vulnerability & Industry Challenges
06:20 – Reality TV & Finding Authenticity
09:50 – The Story Behind “Right On Time”
11:22 – Marriage, Divorce & Clingy Love
15:25 – Dating in the Industry
19:31 – Motherhood & Taking Breaks from Music
22:13 – Recording Energy & Location Vibes
26:00 – How the Industry Has Changed
30:11 – Talent vs. Popularity
34:08 – Early Hustles & Funny Odd Jobs
37:20 – Crazy Dating Stories & Red Flags
43:04 – Money, Gender Roles & Independence
49:00 – Does the Past Define You?
53:36 – Confidence vs. Insecurity
56:00 – Creative Process & Artistic Pressure
58:38 – Closing Thoughts on Legacy & Growth

See omnystudio.com/listener for privacy information.

Transcript

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0:00.0	This is an IHeart podcast.
0:22.7	What's up? It's lip service. I'm Angela Yee. I'm Gigi McGuire. I'm Jordie Jor. Connie Diamond. Leela James. Oh, I love this combination. Yes, me too. First of all, both Connie Diamond and Leela James have a voice like you could tell they do music. Period. No, for real. Y'all got like the... What you want to say?
0:23.5	What kind of voice we got?
0:20.9	Just a music voice. Diamond and Lila James have a voice like you could tell they do music. Period. No, for real.
0:21.6	Y'all got like the- What you know what to say?
0:22.8	What kind of voice we got? Just a music voice. Like you could hear it when you talk. Like it sounds good for you to my. Yeah. Okay. I'm not mad at it. And you're both have projects out right now, new ones. Yes. So congratulations. since we're going to get all into your business.
0:36.7	Okay.
0:38.6	People get nervous.
0:39.7	Connie was like, what are you about to ask me?
0:40.9	I'm so nervous. Yes. So congratulations. We're going to get all into your business. Okay. Don't me.
0:38.3	People get nervous. Connie was like, what you about to ask me? I'm so nervous. I don't know why. Yeah. Well, you know, I think, and I always tell people, we just want you to be comfortable. If there's ever anything, listen, this is the show where you like, take that out, we take it out. Right. as there was even one person that was like,
0:54.6	I don't know if we should air this.
0:56.2	And we didn't.
0:56.9	You know what I'm saying?
0:57.6	Because it ain that was like, I don't know if we should air this.
0:56.2	And we didn't.
0:56.9	You know what I'm saying?
0:57.6	Because it ain't about like trying to have a gotcha moment ever.
1:00.1	It is more about the comfortability of it.
1:02.6	You know, Lila, I think it's been like 20 years since your first project came out.
1:07.8	Well, yeah, the original.
1:09.5	Yeah, the original. Yeah, the original. Yeah, my first album came out 2005. That's crazy. It really is 20 years. Yeah, 2005. I don't know what change is going to come. That is amazing. Congratulations. Thank you. Can you imagine, like, being in the, I've been doing radio for 20 years. Yeah, it was a different thing back then, right? Yes. Think about how much has changed from when you first put out your first project, you know, to what it is now. Yeah. It's very, very different. What would you say how? Like, what's the good things? Well, social media right off the top is, you know, it's played. Changes every day. Yeah. I think that's the biggest difference. I mean. Even how music is put out though now. The music, the way it's put out. Just, I mean, the tension span now too is so short. Yeah. I feel like songs got shorter. Absolutely. Yeah. One thousand percent. Yeah.
	...

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