Dare to Overshare

Jackie Hollywood
  • 5.0 (2)
  • Relationships

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 alone. Because oversharing isn’t a problem, it’s a love language.

  1. The Biggest Lie About Success: A $140M Exit Left Him Depressed | Peter Kennedy

    7h ago

    The Biggest Lie About Success: A $140M Exit Left Him Depressed | Peter Kennedy

    What if achieving everything you've ever wanted still didn't make you happy? After building and selling his company to Sprout Social in a deal worth $140 million, entrepreneur and author Peter Kennedy found himself facing something no one talks about: depression, identity loss, and the unsettling realization that success doesn't always bring fulfillment. In this episode of Dare to Overshare, Peter opens up about the emotional aftermath of success, the pressure to keep chasing bigger goals, and what it really means to reconnect with yourself after spending years pursuing external validation. We talk about the hidden cost of achievement, why so many high performers struggle in silence, and how to tell the difference between ambition that's aligned with your purpose and ambition that's driven by ego. Peter also shares the lessons behind his book, The Remembering, and the questions we should all be asking ourselves when life looks good on paper but doesn't feel good inside. Whether you're building a business, chasing a dream, or simply trying to figure out what truly matters, this conversation is a powerful reminder that success alone won't save you—and that meaning, connection, and self-awareness matter more than we think. In this episode, we discuss: • Selling his company in a $140 million exit • Why success left him feeling depressed • The emotional cost of achievement • Identity and purpose after success • External validation vs. inner fulfillment • The dangers of tying your worth to accomplishments • How to know if your ambition is aligned • What "The Remembering" really means • Practical questions to reconnect with yourself • What he wishes he knew before achieving his dreams Subscribe for more unfiltered conversations on healing, self-worth, relationships, manifestation, and personal growth. Jackie’s socials: https://www.instagram.com/jackiehollywood https://www.instagram.com/daretoovershare https://www.tiktok.com/@itsjackiehollywood https://www.youtube.com/daretoovershare Peter's socials: https://www.instagram.com/therememberingbook You can get his book The Remembering here: https://amzn.to/4eYEIzo

    1h 10m
  2. How Your Thoughts, Words & Beliefs Shape Your Reality | Lyric Perez

    Apr 22

    How Your Thoughts, Words & Beliefs Shape Your Reality | Lyric Perez

    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 can actually come from survival mode. In this episode, we go deep into healing, manifestation, and the connection between your thoughts, your words, and the reality you create. Because it’s not just mindset, it’s how you speak, what you believe, and the patterns you’re still operating from without realizing it. From dropping out of high school and getting her GED to building a career in the entertainment industry, Lyric shares what it really takes to evolve. We talk about how hyper-independence can be rooted in trauma, why receiving support can feel uncomfortable even when you crave it, and how playing small to protect yourself can quietly keep you stuck. This conversation is about: — unlearning survival mode — shifting your mindset and belief systems — manifestation + how your thoughts create your reality — why your words carry more power than you think — healing hyper-independence and learning to receive — building a career in entertainment without a traditional path — working behind the scenes and not always getting recognition — speaking your truth without trying to control outcomes — letting yourself evolve, even when it’s uncomfortable Subscribe for more unfiltered conversations on healing, self-worth, relationships, manifestation, and personal growth. Jackie’s socials: https://www.instagram.com/jackiehollywood https://www.instagram.com/daretoovershare https://www.tiktok.com/@itsjackiehollywood https://www.youtube.com/daretoovershare Lyric’s socials: https://www.instagram.com/lyricspoetic https://www.tiktok.com/@lyricspoetic

    54 min
  3. Behind the Confidence: Lexy Panterra on Fame, Insecurity & Pressure

    Apr 8

    Behind the Confidence: Lexy Panterra on Fame, Insecurity & Pressure

    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 watched by millions. From LexTwerkOut to music, business, and OnlyFans, she opens up about what people get completely wrong about her—and what it actually takes to keep showing up when you don’t feel as confident as you look. We get into: living with Crohn’s disease (and how it affects her daily life)the truth behind her OnlyFans—and why people misunderstand itwhat it’s like being a woman in entertainment dealing with blurred boundaries + unwanted attentionwhy she keeps her relationship private in such a public life This isn’t the polished version you see online. It’s everything behind it. — Subscribe for more unfiltered conversations.

    1h 2m
  4. The Cost of Being the Strong Black Woman | Laila Lopez

    Mar 4

    The Cost of Being the Strong Black Woman | Laila Lopez

    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
  5. Can Faith and Fighting Coexist? | UFC Fighter 'Gifted' Gabe Green

    Feb 18

    Can Faith and Fighting Coexist? | UFC Fighter 'Gifted' Gabe Green

    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
  6. Rebuilding After Rock Bottom: Ashlee Belzo on Love, Identity & Healing

    Feb 4

    Rebuilding After Rock Bottom: Ashlee Belzo on Love, Identity & Healing

    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
  7. Why We Feel Numb: EMoney on Grief, Reality TV & Growing Up Weird

    Jan 21

    Why We Feel Numb: EMoney on Grief, Reality TV & 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
  8. You Don’t Need Trauma to Be Interesting | Margarita Monet of Edge of Paradise

    Jan 7

    You Don’t Need Trauma to Be Interesting | Margarita Monet of Edge of Paradise

    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
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Ratings & Reviews

5
out of 5
2 Ratings

About

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 alone. Because oversharing isn’t a problem, it’s a love language.

Information

  • Creator
    Jackie Hollywood
  • Years Active
    2025 - 2026
  • Episodes
    23
  • Rating
    Explicit
  • Copyright
    © Copyright 2026 Jackie Hollywood
  • Show Website
    Dare to Overshare