Dare to Overshare

Jackie Hollywood
  • 5.0 (2)
  • ENTREPRENEURSHIP

Dare to Overshare is your new favorite safe space where vulnerability meets vibe. Each week, Jackie invites artists, creators, dreamers, and doers to her cozy studio for the kind of deep, unfiltered conversations you wish more people were having. It’s not about interviews—it’s about connection. Every conversation is raw, real, and refreshingly human. From laugh-out-loud moments to jaw-dropping confessions, our guests go there—sharing personal stories, bold opinions, and the kinds of truths you usually only tell your best friend after a glass of wine.

  1. Laila Lopez: "I Don't Always Want To Be The Strong Black Woman" - Laila Lopez: "I Don't Always Wanna Be The Strong Black Woman" - Self Love and Prioritizing Peace

    5D AGO

    Laila Lopez: "I Don't Always Want To Be The Strong Black Woman" - Laila Lopez: "I Don't Always Wanna Be The Strong Black Woman" - Self Love and Prioritizing Peace

    This episode with Entrepreneur and Media Personality Laila Lopez is about growth.We talk about attachment styles and what it really looks like to date someone emotionally unavailable. We unpack the mind-body connection, manifestation, and how unprocessed emotions can live in the body longer than we think.Laila opens up about building her skincare brand, Ebon Essentials, while privately struggling with hormonal acne — and the courage it takes to show up imperfectly. We also get into career pivots, walking away from spaces that no longer feel aligned, and redefining success on your own terms.There’s a wild dating story that will have you shaking your head, but underneath it is a bigger conversation about standards, self-worth, and choosing yourself fully. Follow us! Jackie's socials: https://www.instagram.com/jackiehollywood https://www.instagram.com/daretoovershare https://www.tiktok.com/@itsjackiehollywood https://www.youtube.com/daretoovershare Laila's socials: https://www.instagram.com/mslailalopez https://www.tiktok.com/@mslailalopez

    51 min
  2. Gifted Gabe Green: "I Can Love You & Punch You In The Face" - Faith, Fighting, And Finding Purpose

    FEB 18

    Gifted Gabe Green: "I Can Love You & Punch You In The Face" - Faith, Fighting, And Finding Purpose

    This week I sat down with pro fighter and UFC athlete 'Gifted' Gabe Green, and Gabe opens up about the health battle that changed everything, his spiritual awakening after years of being a skeptic, and we address the big question: Can you be a true Christian and a fighter? Gabe explains why fighting is an art form, a craft he believes God gave him the ability to perfect — not a platform for anger or malice. We talk about the stereotype that fighters get, why men should wear skirts, his (slightly radical) solution to world war and why martial arts training should be mandatory for everyone. We get into practical self-defense advice, including what to do in worst-case scenarios. This episode is about more than fighting. It’s about identity, faith, masculinity, discipline, and questioning the systems we were handed. If you’ve ever wrestled with doubt, felt misunderstood, or tried to balance strength with softness — this one’s for you. Follow us! Jackie's socials: https://www.instagram.com/jackiehollywood https://www.instagram.com/daretoovershare https://www.tiktok.com/@itsjackiehollywood https://www.youtube.com/daretoovershare Gabe's socials: https://www.instagram.com/giftedgabegreen https://www.tiktok.com/@giftedgabegreen

    57 min
  3. Ashlee Belzo: "I Was Forced Out Of The Closet" - Breakups, Brain Injuries, and Breakthroughs

    FEB 4

    Ashlee Belzo: "I Was Forced Out Of The Closet" - Breakups, Brain Injuries, and Breakthroughs

    I’m joined by CEO of Puff Dao and Girls Gays & Theys, Ashlee Belzo, and this episode is a wild ride. We get into the car accident that caused her traumatic brain injury, the anxiety that followed, and the wake-up call she needed to slow down. We also get into the messiness of dating, the chaos of toxic relationships, and how love will always expose your shadow side. Plus, we talk love languages and the wild way Ashlee was forced out of the closet.We also get into the struggles behind being a CEO and Event Organizer. Between last-minute ticket buyers and people acting too cool to pay, Ashlee spills all the behind-the-scenes of curating a vibe while holding it all together.If you’ve ever had to rebuild after hitting rock bottom, navigated love while healing, or just needed a reminder that you're not alone, this episode is for you. Follow us! Jackie's socials: https://www.instagram.com/jackiehollywood https://www.instagram.com/daretoovershare https://www.tiktok.com/@itsjackiehollywood https://www.youtube.com/daretoovershare Ashlee's socials: https://www.instagram.com/ashleebelzo https://www.instagram.com/girlsgaystheysla https://www.instagram.com/puffdao https://www.tiktok.com/@ashleebelzo

    40 min
  4. EMoney: "I Don't Cry When My Friends Die": Repressed Feelings, Reality TV Lies & Growing Up Weird

    JAN 21

    EMoney: "I Don't Cry When My Friends Die": Repressed Feelings, Reality TV Lies & Growing Up Weird

    This week, artist EMoney is in the building and we get very real, very fast. EMoney was on Season 6 of MTV's Are You The One so he knows what goes on behind the cameras. We’re unpacking the absolute chaos of reality TV — from the psychological high of morally questionable people to the behind-the-scenes manipulation that happens with executive producers and cast members. Is it entertainment... or emotional warfare? We also dive into the heavier stuff: why some of us can cry during movies but not in real life situations like death, the quiet day-to-day sadness we avoid with dopamine scrolls, and living with Trichotillomania since childhood. Plus: the Taylor Swift discourse that might get some of y’all mad (you’ve been warned), cancel culture fatigue, and why Gen Z is basically shutting the bar scene down. It’s unfiltered, a little unhinged, and full of the kind of honesty you’re not supposed to say out loud. Follow us! Jackie's socials: https://www.instagram.com/jackiehollywood https://www.instagram.com/daretoovershare https://www.tiktok.com/@itsjackiehollywood https://www.youtube.com/daretoovershare Emoney's socials: https://www.instagram.com/emoneydoesit https://www.tiktok.com/@emoneydoesit https://www.youtube.com/@emoneymusic

    49 min
  5. Margarita Monet: "You Don't Need Trauma To Be Interesting": From Band Breakups to Self Love

    JAN 7

    Margarita Monet: "You Don't Need Trauma To Be Interesting": From Band Breakups to Self Love

    Margarita Monet, lead singer of Edge of Paradise, joins me to talk about the pressure to have “trauma” to make good art, the truth about being in a rock band, and why healing doesn't have to be performative. From band breakups and anxiety to cultural expectations around aging, marriage, and motherhood—we cover it all. In this episode, we get into what it really means to be honest, how to let go of people without losing yourself, and how Margarita built confidence without conforming to the “tortured artist” stereotype. She shares how being a frontwoman in a rock band shaped her, the guilt of not having a traumatic past, and why she’s unlearning people-pleasing for good. If you’ve ever felt like you needed to struggle to be taken seriously—or felt pressure to stay in relationships (creative or personal) that no longer align—this one’s for you. Follow us! Jackie's socials: https://www.instagram.com/jackiehollywood https://www.instagram.com/daretoovershare https://www.tiktok.com/@itsjackiehollywood https://www.youtube.com/daretoovershare Margarita's socials: https://www.instagram.com/margarita.monet https://www.instagram.com/edgeofparadise https://www.tiktok.com/@edgeofparadiseband

    53 min
  6. Tara Katchur: "I Was Ghosted By My Bridesmaids" - Wedding Drama, Addiction, and Colonoscopies

    12/10/2025

    Tara Katchur: "I Was Ghosted By My Bridesmaids" - Wedding Drama, Addiction, and Colonoscopies

    In this episode, Reality TV Casting Producer Tara Katchur gets honest in a way she never has before. She talks about the childhood friends who ghosted her on her wedding day, what it felt like to keep showing up for people who didn’t show up for her, and the moment she finally learned to listen when someone shows you who they are. Tara also opens up about growing up with a dual-diagnosed mom and the years she spent being the “parent” in her family. She shares the ultimatum that changed everything and the exhaustion of always keeping it together. She even tells the story of the colonoscopy she had at 24—how gaining twenty pounds led her to a doctor’s office, and how finding polyps early ended up saving her life. We wrap with a conversation about beauty pressures coming from shows like Love Island, and what she’s learned about putting herself out there online. As Tara says, it costs nothing to support someone’s work… even though the internet can be a strange place. Follow us! Jackie's socials: https://www.instagram.com/jackiehollywood https://www.instagram.com/daretoovershare https://www.tiktok.com/@itsjackiehollywood https://www.youtube.com/daretoovershare Tara socials: https://www.instagram.com/tarakatchur https://www.tiktok.com/@tarakatchur

    49 min
  7. Lew: "I Used to Steal Food Deliveries" - Surviving Heartbreak, Hollywood, and Hitting Rock Bottom

    11/26/2025

    Lew: "I Used to Steal Food Deliveries" - Surviving Heartbreak, Hollywood, and Hitting Rock Bottom

    In this episode, one of my favorite artists, Lew, sits down with me to chat about the messy truths of dating and the real struggle behind the artistry. This conversation is raw, reflective, and painfully relatable—especially if you've ever ignored red flags just to feel loved. We overshare about: Taking back a cheating ex and gender double standards Trusting your gut and spotting red flags early The pressure to define “exclusive” in today’s dating world How heartbreak can harden you—and how to soften again Moving to LA with no job, no money, and no backup plan The emotional rollercoaster of working in entertainment Drake being the GOAT of storytelling Lew’s story is a reminder that rock bottom builds character—but courage is what makes you stay. Follow us! Jackie's socials: https://www.instagram.com/jackiehollywood https://www.instagram.com/daretoovershare https://www.tiktok.com/@itsjackiehollywood https://www.youtube.com/daretoovershare Lew's socials: https://www.instagram.com/lewintherain https://www.tiktok.com/@lewintherain

    44 min
  8. Tyler Therapy: "Finally Free from People Pleasing" – Motherhood, Identity Loss & Rediscovery

    11/12/2025

    Tyler Therapy: "Finally Free from People Pleasing" – Motherhood, Identity Loss & Rediscovery

    In this episode, we dive into what it feels like to wear all the hats: being a mom, a creator, and a woman rediscovering herself while holding it down for everyone else. From breaking generational cycles and snapping out of people-pleasing, to navigating identity beyond motherhood and embracing the alter ego we all lean on sometimes. We talk: Early midlife crises and the “stuck” feeling no one warns you about The mask we wear vs. the healing we need How becoming a mom fast-tracks your evolution Breaking generational traumas and raising emotionally aware kids The mental load women carry and why self-care isn’t selfish The reality of “snapback” culture, identity loss, and reclaiming your body Calling out toxic masculinity and why men need safe spaces too This one’s for the mom who feels like she’s losing herself, the creative stuck in a loop, the woman learning to say no, and the human just trying to make sense of it all.Tyler said it best: "I'm a mom and still a baddie." Follow us! Jackie's socials: https://www.instagram.com/jackiehollywood https://www.instagram.com/daretoovershare https://www.tiktok.com/@itsjackiehollywood https://www.youtube.com/daretoovershare Tyler's socials: https://www.instagram.com/tylertherapy https://www.tiktok.com/@badmuthapuffa

    52 min
See All (20)

Ratings & Reviews

5
out of 5
2 Ratings

About

Dare to Overshare is your new favorite safe space where vulnerability meets vibe. Each week, Jackie invites artists, creators, dreamers, and doers to her cozy studio for the kind of deep, unfiltered conversations you wish more people were having. It’s not about interviews—it’s about connection. Every conversation is raw, real, and refreshingly human. From laugh-out-loud moments to jaw-dropping confessions, our guests go there—sharing personal stories, bold opinions, and the kinds of truths you usually only tell your best friend after a glass of wine.

Information

  • Creator
    Jackie Hollywood
  • Years Active
    2025 - 2026
  • Episodes
    20
  • Rating
    Explicit
  • Copyright
    © Copyright 2026 Jackie Hollywood
  • Show Website
    Dare to Overshare