Dare to Overshare
Jackie Hollywood
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Recent Episodes
S2E11 Lyric Perez: "Your Word Is Your Wand" — You Want It… So Why Are You Blocking It?
Lyric Perez—Producer, Director, Songwriter, and creative force—built her career without the traditional path. No roadmap, no safety net. But what looks like confidence and independence on the outside…
S2E10 Lexy Panterra: “Me? I’m The Ghetto Booty Rapper?” — Industry Advice, Harsh Truths & Misconceptions
Everyone thinks she’s the confident girl… but that’s not the full story.Lexy Panterra built a viral brand off confidence—while quietly dealing with insecurity, pressure, and the reality of being…
S2E9 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…
S2E8 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,…
S2E7 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…
S2E6 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…
S2E5 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…
S2E4 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…
S2E3 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…
S2E2 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…
S2E1 Phenix Red: "Extreme Feminism is Problematic" - Healing Without Hating Men
Artist and Director Phenix Red joins me for a raw, unfiltered convo about what it means to be a woman in a world that’s constantly telling you to be better, prettier, thinner, calmer. We talk body…
S1E11 Amanda Butler: "I Have 93 Italian Husbands” - Navigating Life After Breast Cancer
Amanda Butler joins me for one of the most raw, vulnerable, and empowering conversations we’ve had yet. Diagnosed with stage 2 breast cancer in her early 30s, Amanda walks us through what it really…
S1E10 Kaitlyn Herman: "Reality TV Is Darker & Crazier Than You Think" - The Truth Behind The Cameras
I sat down with Kaitlyn Herman — former Big Brother contestant turned Life Coach — and we're talking reality TV trauma to cancel culture. We chat about what people don’t see when they're watching…
S1E9 Flo Tapia: "I Used To Bed Rot For Weeks" - Rewiring Your Brain and Finding Your Purpose
In this episode, I’m joined by content creator Flo Tapia for a deep, unfiltered convo about the highs and the lows of being your own worst enemy. We get into struggling with laziness, toxic…
S1E8 Zamaria Thompson: "Hot Girls Have Stomach Issues" - Gut Health, Feeling All The Feels & Manifesting
In this episode, I sit down with Zamaria Thompson, who is a health and wellness coach and creator and we get into the real tea on gut health — how mindfulness while eating matters and doing less is…
S1E7 Kimmy Tan: "Go To Your Butt Doctor" - From Toxic Love to Showing Up Authentically Online
In this episode of Dare to Overshare, I sit down with the multifaceted Kimmy Tan — YouTuber, musician, tattoo artist, and all-around creative force. We dive deep into her journey of evolving beyond…
S1E6 Chad the Maverick: "People Forgot How To Be People" - We’re More Than Our Star Signs
In this episode of Dare to Overshare, Jackie Hollywood sits down with astrologer Chad the Maverick to explore how astrology can be a grounding tool in everyday life—without letting it dictate every…
S1E5 V The Plug: "I Signed Up On A Sugar Baby Site" - When Money Tests Morals
In this thought-provoking episode, Jackie is joined by V The Plug for a raw, reflective, and hilarious deep-dive into modern dating, gender roles, and the hustle behind OnlyFans / Sugar Baby culture.…
S1E4 Alicia Waldner: "OnlyFans Funded My Startup" - The Uncensored Path to CEO Status
In this raw and inspiring episode, CEO / Founder of Exist, Alicia Waldner, shares how she turned bold choices into big business. From launching her tech startup with half a million dollars earned on…
S1E3 King Hoodie: "God Told Me to Be Celibate" – Healing Insecurities About Women and Money
“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…
Frequently Asked Questions
Dare to Overshare has published 22 episodes since June 2025, covering topics in Business, Education.
Dare to Overshare is currently highly active with new episodes every 2 weeks. Average episode length is 46m.
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