Jackie Hollywood

Dare to Overshare

Society EN ↓ 28 episodes

The conversations we avoid are the ones we need to have the most. Dare to Overshare is a safe space for the refreshingly human conversations we usually keep to ourselves. In each episode, Jackie sits down with artists, creators, entrepreneurs, and everyone in between to talk about the things most people are afraid to say out loud. We dive deep into topics like identity, healing, relationships, mental health, fame, failure, faith, self-worth, and more. It’s not about perfect interviews or polished answers. It’s about connection, honesty, and the kind of oversharing that makes you feel less alon...

Be sure to visit the podcast's website and support the creator: daretoovershare.captivate.fm

Author

Jackie Hollywood

Episodes

He Chased Women, Money & Status—Then Chose Celibacy | King Hoodie 09.07.2025 43:15

“God told me to be celibate.” That’s what rapper King Hoodie realized in a moment of spiritual clarity — and it changed everything. In this raw and unfiltered episode, we dive deep into the insecurities men rarely talk about: money, women, validation, and the pressure to prove your worth. King Hoodie opens up about growing up with nothing, chasing status through material things and women, and the...

The Dark Side of Being Known Online, Boundaries Beyond the Algorithm | Dare Taylor 02.07.2025 40:35

You might know her from the internet… but Content Creator Dare Taylor is here to remind you: that doesn’t mean you know her in real life. In this episode, Dare gets real about the blurry line between public and private when you live your life online. We talk about boundaries with fans, burnout, and the pressure to turn everything into content. She opens up about reconnecting with joy through figur...

Love Island Made Him Famous, But He Still Felt Lonely | Calvin Cobb 25.06.2025 44:40

What happens when a Love Island star gets vulnerable about loneliness, mental health, and… matcha? Calvin Cobb pulls up to overshare like never before. We talk panic attacks from a man’s perspective, emotional growth, loneliness that can linger even in a room full of people and why matcha just isn't for everybody. From being misunderstood to craving connection, this episode is raw, real, and comfo...