<![CDATA[Dare to Overshare]]>6c875a35-5fb1-5197-b359-1ccac505646bWed, 12 Aug 2026 07:00:21 +0000Captivate.fmJackie Hollywoodhttps://artwork.captivate.fm/afca95ae-8958-493e-be64-f6431d2700bc/zEZqFAzXsxbFHuT9096VVw7_.jpgDare to OvershareJackie HollywoodJackie HollywoodThe 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.https://daretoovershare.captivate.fmtrueepisodicnopodcastThe Man Behind Real-Life AI Holograms | David Nussbaum, Founder of ProtoThe Man Behind Real-Life AI Holograms | David Nussbaum, Founder of ProtoJackie sits down with David Nussbaum, founder of Proto, to talk about AI holograms, real-life holoportation, entrepreneurship, and what it actually takes to build something before the world understands it.

David created Proto around a wild idea: what if someone could appear right in front of you from anywhere in the world and actually feel like they were there? What started as a futuristic vision has become a real company using hologram technology, AI avatars, and human-like digital presence in airports, doctor’s offices, museums, entertainment, and beyond.

David shares how he came up with the idea for Proto, what it was like getting rejected over and over again, why entrepreneurs have to be a little delusional, and how he knew this was the idea worth betting on. He also opens up about building a company from scratch, pitching a technology people didn’t understand yet, balancing ambition with family, and learning how to turn impossible ideas into something real.

This conversation is for anyone with a big dream, a business idea, a creative vision, or a goal that feels too weird, too early, or too impossible. It’s about trusting your vision before other people understand it, building through rejection, and learning when an idea is actually worth betting your life on.

In this episode:

  • What Proto Hologram is and how it works
  • The future of AI holograms and AI avatars
  • How David Nussbaum founded Proto
  • Why presence is the secret sauce behind hologram technology
  • Getting rejected while building a startup
  • Howie Mandel sliding into David’s DMs
  • Proto on Big Brother
  • AI avatars in airports like SFO, JFK, LaGuardia, and Boston Logan
  • Hologram technology in healthcare and doctor’s offices
  • The Ozzy Osbourne AI avatar and digital legacy
  • Entrepreneurship, manifestation, persistence, and betting on your vision

]]>Jackie sits down with David Nussbaum, founder of Proto, to talk about AI holograms, real-life holoportation, entrepreneurship, and what it actually takes to build something before the world understands it.

David created Proto around a wild idea: what if someone could appear right in front of you from anywhere in the world and actually feel like they were there? What started as a futuristic vision has become a real company using hologram technology, AI avatars, and human-like digital presence in airports, doctor’s offices, museums, entertainment, and beyond.

David shares how he came up with the idea for Proto, what it was like getting rejected over and over again, why entrepreneurs have to be a little delusional, and how he knew this was the idea worth betting on. He also opens up about building a company from scratch, pitching a technology people didn’t understand yet, balancing ambition with family, and learning how to turn impossible ideas into something real.

This conversation is for anyone with a big dream, a business idea, a creative vision, or a goal that feels too weird, too early, or too impossible. It’s about trusting your vision before other people understand it, building through rejection, and learning when an idea is actually worth betting your life on.

In this episode:

  • What Proto Hologram is and how it works
  • The future of AI holograms and AI avatars
  • How David Nussbaum founded Proto
  • Why presence is the secret sauce behind hologram technology
  • Getting rejected while building a startup
  • Howie Mandel sliding into David’s DMs
  • Proto on Big Brother
  • AI avatars in airports like SFO, JFK, LaGuardia, and Boston Logan
  • Hologram technology in healthcare and doctor’s offices
  • The Ozzy Osbourne AI avatar and digital legacy
  • Entrepreneurship, manifestation, persistence, and betting on your vision

]]>aab41500-62cd-4756-982b-533a74d85c94Wed, 12 Aug 2026 00:00:00 -070001:02:53truefull3443Reality TV Gave Her Fame... But Took Away Her Identity | Simone KellyReality TV Gave Her Fame... But Took Away Her Identity | Simone KellySimone Kelly became known through MTV's Are You The One? and The Challenge, but fame came with a price she never expected: losing her sense of identity. In this episode, we talk about what it's really like to be judged by millions, how reality TV can blur the line between who you are and who people think you are, and why walking away from something that made you famous can be one of the hardest decisions you'll ever make. Simone opens up about rebuilding her confidence through music, healing from an emotionally abusive relationship, the surprising lesson she learned about manifesting fame, and why she believes "selling your soul" isn't always what people think it is. If you've ever felt misunderstood, trapped by other people's expectations, or like you had to reinvent yourself to become who you really are, this conversation is for you.

]]>Simone Kelly became known through MTV's Are You The One? and The Challenge, but fame came with a price she never expected: losing her sense of identity. In this episode, we talk about what it's really like to be judged by millions, how reality TV can blur the line between who you are and who people think you are, and why walking away from something that made you famous can be one of the hardest decisions you'll ever make. Simone opens up about rebuilding her confidence through music, healing from an emotionally abusive relationship, the surprising lesson she learned about manifesting fame, and why she believes "selling your soul" isn't always what people think it is. If you've ever felt misunderstood, trapped by other people's expectations, or like you had to reinvent yourself to become who you really are, this conversation is for you.

]]>8a6c23d1-b6bd-47f2-b5c7-6ae363e6f392Wed, 22 Jul 2026 00:00:00 -070001:05:54truefull3333The Biggest Lie About Success: A $140M Exit Left Him Depressed | Peter KennedyThe Biggest Lie About Success: A $140M Exit Left Him Depressed | Peter KennedyWhat 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

]]>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

]]>ba771ed1-6286-4b24-988a-da4f57d80ce0Wed, 01 Jul 2026 00:00:00 -070001:10:05truefull3223How Your Thoughts, Words & Beliefs Shape Your Reality | Lyric PerezHow Your Thoughts, Words & Beliefs Shape Your Reality | Lyric PerezLyric 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

]]>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

]]>615859d9-2463-4ab1-8cf1-020b4c4f7b1dWed, 22 Apr 2026 00:00:00 -070053:56truefull210102Behind the Confidence: Lexy Panterra on Fame, Insecurity & PressureBehind the Confidence: Lexy Panterra on Fame, Insecurity & PressureEveryone 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 it
  • what it’s like being a woman in entertainment dealing with blurred boundaries + unwanted attention
  • why 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.

]]>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 it
  • what it’s like being a woman in entertainment dealing with blurred boundaries + unwanted attention
  • why 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.

]]>b1f19daa-cc72-4172-85ea-404d58bfb98eWed, 08 Apr 2026 00:00:00 -070001:01:44truefull3113The Cost of Being the Strong Black Woman | Laila LopezThe Cost of Being the Strong Black Woman | Laila LopezThis 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

]]>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

]]>0e76e30b-2f87-45e5-a138-090fd86ea2c0Wed, 04 Mar 2026 00:00:00 -070051:09truefull2992Can Faith and Fighting Coexist? | UFC Fighter 'Gifted' Gabe GreenCan Faith and Fighting Coexist? | UFC Fighter 'Gifted' Gabe GreenThis 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

]]>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

]]>b80deeec-7e2d-4760-a25e-ff1e0fe9fa00Wed, 18 Feb 2026 00:00:00 -070056:31truefull2882Rebuilding After Rock Bottom: Ashlee Belzo on Love, Identity & HealingRebuilding After Rock Bottom: Ashlee Belzo on Love, Identity & HealingI’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

]]>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

]]>844e4bf5-79d1-4436-beac-0311eddf6bdaWed, 04 Feb 2026 00:00:00 -070040:22truefull2772Why We Feel Numb: EMoney on Grief, Reality TV & Growing Up WeirdWhy We Feel Numb: EMoney on Grief, Reality TV & Growing Up WeirdThis 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

]]>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

]]>53db98f6-55f1-43da-900c-579369081c91Wed, 21 Jan 2026 00:00:00 -070048:46truefull2662You Don’t Need Trauma to Be Interesting | Margarita Monet of Edge of ParadiseYou Don’t Need Trauma to Be Interesting | Margarita Monet of Edge of ParadiseMargarita 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

]]>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

]]>8f19e202-6a07-4742-b239-fad1b85d834bWed, 07 Jan 2026 00:00:00 -070052:43truefull2552When People Don’t Show Up: Ghosting, Addiction & Boundaries | Tara KatchurWhen People Don’t Show Up: Ghosting, Addiction & Boundaries | Tara KatchurIn 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

]]>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

]]>f0c0025b-7af1-4668-a8d5-dba0b8263860Wed, 10 Dec 2025 00:00:00 -070049:13truefull2442What Rock Bottom Teaches You About Love, Art & Survival | LewWhat Rock Bottom Teaches You About Love, Art & Survival | LewIn 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

]]>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

]]>eaa0a087-0d39-4c49-966e-66479977e022Wed, 26 Nov 2025 00:00:00 -070043:49truefull2332For the Mom Who Feels Like She’s Losing Herself | Tyler TherapyFor the Mom Who Feels Like She’s Losing Herself | Tyler TherapyIn 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

]]>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

]]>10803cdd-6f41-4207-88c4-1c035124d2caWed, 12 Nov 2025 00:00:00 -070051:31truefull2222Healing Without Hating Men: Phenix Red on Feminism, Beauty & Self-WorthHealing Without Hating Men: Phenix Red on Feminism, Beauty & Self-WorthArtist 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 dysmorphia, emotional sensitivity, and the very real struggle of trying to “heal” while still being pissed off at the systems that broke us.

We get into everything from WebMD spirals to chasing beauty trends to looking for meaning in a culture obsessed with productivity and perfection. Phenix opens up about growing up with a father who didn’t like women, why she’s been hesitant to speak on feminism, and the fine line between fighting for equality and just... hating men.

We also touch on imposter syndrome (she doesn’t believe in it), human design, and why playing like a child might actually be the secret to success.

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

Phenix's socials:

https://www.instagram.com/phenixredmusic

https://www.tiktok.com/@phenixredmusic

]]>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 dysmorphia, emotional sensitivity, and the very real struggle of trying to “heal” while still being pissed off at the systems that broke us.

We get into everything from WebMD spirals to chasing beauty trends to looking for meaning in a culture obsessed with productivity and perfection. Phenix opens up about growing up with a father who didn’t like women, why she’s been hesitant to speak on feminism, and the fine line between fighting for equality and just... hating men.

We also touch on imposter syndrome (she doesn’t believe in it), human design, and why playing like a child might actually be the secret to success.

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

Phenix's socials:

https://www.instagram.com/phenixredmusic

https://www.tiktok.com/@phenixredmusic

]]>8ee9bba4-6311-4dbc-9c35-1f514ced51ceWed, 15 Oct 2025 00:00:00 -070056:14truefull2112Life After Breast Cancer: Dating, Identity & Feeling Like Yourself Again | Amanda ButlerLife After Breast Cancer: Dating, Identity & Feeling Like Yourself Again | Amanda ButlerAmanda 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 looks like to navigate womanhood, dating, and identity when your body and life are completely redefined — seemingly overnight.

We get into:

– Life post-cancer and what doctors don’t prepare you for

– Dating while in medical menopause

– Brain fog, no libido, and the silent mental toll it takes

– Comparing dating in the US vs Internationally

– What cancer clarified about love, friendship, and her future

– The unexpected wisdom we gain from our parents

and so much more!

This is for anyone who's ever felt like their body betrayed them, or like they’re grieving the life they thought they’d have. You are not alone.

Wanna overshare? Apply to be a guest on the show!

https://www.daretoovershare.com

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

Amanda socials:

https://www.instagram.com/hiamandabutler

https://www.tiktok.com/@hiamandabutler

https://www.instagram.com/cancerbaddies

]]>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 looks like to navigate womanhood, dating, and identity when your body and life are completely redefined — seemingly overnight.

We get into:

– Life post-cancer and what doctors don’t prepare you for

– Dating while in medical menopause

– Brain fog, no libido, and the silent mental toll it takes

– Comparing dating in the US vs Internationally

– What cancer clarified about love, friendship, and her future

– The unexpected wisdom we gain from our parents

and so much more!

This is for anyone who's ever felt like their body betrayed them, or like they’re grieving the life they thought they’d have. You are not alone.

Wanna overshare? Apply to be a guest on the show!

https://www.daretoovershare.com

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

Amanda socials:

https://www.instagram.com/hiamandabutler

https://www.tiktok.com/@hiamandabutler

https://www.instagram.com/cancerbaddies

]]>fa49adf5-9370-47ae-858f-87d46dbb5bb3Wed, 03 Sep 2025 00:00:00 -070039:12truefull111111Big Brother’s Kaitlyn Herman on Reality TV, Trauma & Life After the ShowBig Brother’s Kaitlyn Herman on Reality TV, Trauma & Life After the ShowI 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 reality shows, and how the version of someone you meet on screen is not always the same as the energy you’d get in real life. Kaitlyn shares what it’s really like being judged by millions and how that experience shaped who she is and what she does for a livng today. We also get into the chaos of separating the art from the artist and why sometimes it's okay to be a hypocrite. This episode is part tea, part therapy — and we hope you’ll leave with a new level of compassion for the people you see on TV.

Wanna overshare? Apply to be a guest on the show!

https://www.daretoovershare.com

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

Kaitlyn's socials:

https://www.instagram.com/kaitlyn_herman

https://www.tiktok.com/@kaitlynherman_

]]>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 reality shows, and how the version of someone you meet on screen is not always the same as the energy you’d get in real life. Kaitlyn shares what it’s really like being judged by millions and how that experience shaped who she is and what she does for a livng today. We also get into the chaos of separating the art from the artist and why sometimes it's okay to be a hypocrite. This episode is part tea, part therapy — and we hope you’ll leave with a new level of compassion for the people you see on TV.

Wanna overshare? Apply to be a guest on the show!

https://www.daretoovershare.com

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

Kaitlyn's socials:

https://www.instagram.com/kaitlyn_herman

https://www.tiktok.com/@kaitlynherman_

]]>5d11f547-756d-4c18-8673-1a5920756f91Wed, 27 Aug 2025 00:00:00 -070047:30truefull110101How to Rewire Your Brain When You Feel Stuck | Flor TapiaHow to Rewire Your Brain When You Feel Stuck | Flor TapiaIn 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 relationships with weed, bed rotting, and the constant challenge of building structure when you work for yourself. We discuss rewiring your brain and the power of shifting your mindset in real-time using the 5 second rule. From psychedelics and spiritual awakenings to the dark side of concerts, this episode is full of moments that’ll make you feel seen.

Wanna overshare? Apply to be a guest on the show!

https://www.daretoovershare.com

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

Flo's socials:

https://www.instagram.com/highitsflo

https://www.tiktok.com/@highitsfloo

]]>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 relationships with weed, bed rotting, and the constant challenge of building structure when you work for yourself. We discuss rewiring your brain and the power of shifting your mindset in real-time using the 5 second rule. From psychedelics and spiritual awakenings to the dark side of concerts, this episode is full of moments that’ll make you feel seen.

Wanna overshare? Apply to be a guest on the show!

https://www.daretoovershare.com

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

Flo's socials:

https://www.instagram.com/highitsflo

https://www.tiktok.com/@highitsfloo

]]>6b126c47-4013-4865-8915-dba14454e79dWed, 20 Aug 2025 00:00:00 -070048:59truefull1991What Gut Health & Mindful Eating Teach Us About Feeling Everything | Zamaria ThompsonWhat Gut Health & Mindful Eating Teach Us About Feeling Everything | Zamaria ThompsonIn 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 often more helpful than doing more. We also dive into the mindset side of wellness: how the universe is never on a budget (so yes, you can ask for more when manifesting) and why even the most positive, uplifting people still need to fully feel the “hard” emotions. Plus, a little detour into relationship talk — the art of soft vs. hard launching your partner.

Wanna overshare? Apply to be a guest on the show!

https://www.daretoovershare.com

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

Zamaria's socials:

https://www.instagram.com/happyfitzam

https://www.tiktok.com/@happyfitzam

]]>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 often more helpful than doing more. We also dive into the mindset side of wellness: how the universe is never on a budget (so yes, you can ask for more when manifesting) and why even the most positive, uplifting people still need to fully feel the “hard” emotions. Plus, a little detour into relationship talk — the art of soft vs. hard launching your partner.

Wanna overshare? Apply to be a guest on the show!

https://www.daretoovershare.com

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

Zamaria's socials:

https://www.instagram.com/happyfitzam

https://www.tiktok.com/@happyfitzam

]]>d54f08d7-7a43-4c31-8641-f60e9851ee1cWed, 13 Aug 2025 00:00:00 -070037:38truefull1881Breaking Out of Toxic Love & Showing Up Authentically Online | Kimmy TanBreaking Out of Toxic Love & Showing Up Authentically Online | Kimmy TanIn 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 cannabis content and embracing her full, authentic self online. Kimmy opens up about what it really means to break out of toxic relationships and how your brain isn't fully developed before 25. We also discuss the fear of our significant others passing away amongst other fears we have. This episode is raw, real, and full of wisdom and laughs.

Wanna overshare? Apply to be a guest on the show!

https://www.daretoovershare.com

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

Kimmy's socials:

https://www.instagram.com/kimmytanofficial

https://www.tiktok.com/@kimmytanofficial

https://www.youtube.com/@kimmytan420

https://www.youtube.com/@kimmytan2.0

]]>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 cannabis content and embracing her full, authentic self online. Kimmy opens up about what it really means to break out of toxic relationships and how your brain isn't fully developed before 25. We also discuss the fear of our significant others passing away amongst other fears we have. This episode is raw, real, and full of wisdom and laughs.

Wanna overshare? Apply to be a guest on the show!

https://www.daretoovershare.com

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

Kimmy's socials:

https://www.instagram.com/kimmytanofficial

https://www.tiktok.com/@kimmytanofficial

https://www.youtube.com/@kimmytan420

https://www.youtube.com/@kimmytan2.0

]]>b724f1c3-4cd3-49db-9543-d3c720dbfbceWed, 06 Aug 2025 00:00:00 -070039:43truefull1771Astrology Should Guide You, Not Control You | Chad the Maverick on Modern SpiritualityAstrology Should Guide You, Not Control You | Chad the Maverick on Modern SpiritualityIn 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 decision. Chad shares his experience navigating the world as a Black male astrologer in a field often dominated by white women, and how his presence is helping shift the culture of modern spirituality.

They talk about using astrology as a way to deepen self-awareness rather than control relationships or obsess over cosmic timing. Chad opens up about why he doesn’t read his partner’s birth chart unless asked, and why we shouldn't let things like Mercury in retrograde run our lives. This episode is all about reclaiming your intuition, tuning out the noise, and aligning with your passions.

Wanna overshare? Apply to be a guest on the show!

https://www.daretoovershare.com

Follow us!

Jackie's socials:

https://www.instagram.com/jackiehollywood

https://www.instagram.com/daretoovershare

https://www.tiktok.com/@itsjackiehollywood

Chad's socials:

https://www.instagram.com/chadthemaverick

https://www.tiktok.com/@chadthemaverick

]]>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 decision. Chad shares his experience navigating the world as a Black male astrologer in a field often dominated by white women, and how his presence is helping shift the culture of modern spirituality.

They talk about using astrology as a way to deepen self-awareness rather than control relationships or obsess over cosmic timing. Chad opens up about why he doesn’t read his partner’s birth chart unless asked, and why we shouldn't let things like Mercury in retrograde run our lives. This episode is all about reclaiming your intuition, tuning out the noise, and aligning with your passions.

Wanna overshare? Apply to be a guest on the show!

https://www.daretoovershare.com

Follow us!

Jackie's socials:

https://www.instagram.com/jackiehollywood

https://www.instagram.com/daretoovershare

https://www.tiktok.com/@itsjackiehollywood

Chad's socials:

https://www.instagram.com/chadthemaverick

https://www.tiktok.com/@chadthemaverick

]]>532da451-1858-47af-b520-6a53490f8d04Wed, 30 Jul 2025 00:00:00 -070042:47truefull1661When Money Tests Your Morals: V The Plug on Self-Worth & BoundariesWhen Money Tests Your Morals: V The Plug on Self-Worth & BoundariesIn 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. Vanessa opens up about signing up on a sugar baby site, seriously considering selling feet pics, and the internal moral tug-of-war that followed. This is a deep conversation about self-worth, boundaries, and what truly aligns with one's values.

]]>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. Vanessa opens up about signing up on a sugar baby site, seriously considering selling feet pics, and the internal moral tug-of-war that followed. This is a deep conversation about self-worth, boundaries, and what truly aligns with one's values.

]]>a7d40283-947a-42c9-a51f-39cc98d7314aWed, 23 Jul 2025 00:00:00 -070041:16truefull1551She Made $500K on OnlyFans to Fund Her Startup | Alicia WaldnerShe Made $500K on OnlyFans to Fund Her Startup | Alicia WaldnerIn 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 OnlyFans to navigating the tech world as an unapologetically 'sexy' female founder, Alicia holds nothing back.

We dive deep into her personal journey—what drove her to take risks, how she handled judgment, and what it really takes to build an empire on your own terms. Alicia also opens up about surviving a toxic relationship that nearly derailed her path, and how she found the strength to leave, heal, and rebuild stronger than ever.

Wanna overshare? Apply to be a guest on the show!

https://www.daretoovershare.com

Follow us!

Jackie's socials:

https://www.instagram.com/jackiehollywood

https://www.instagram.com/daretoovershare

https://www.tiktok.com/@itsjackiehollywood

Alicia Waldner's socials:

https://www.instagram.com/aliciawaldner

https://www.tiktok.com/@aliciawaldner

https://www.tiktok.com/@existapp

https://www.instagram.com/theexistapp

]]>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 OnlyFans to navigating the tech world as an unapologetically 'sexy' female founder, Alicia holds nothing back.

We dive deep into her personal journey—what drove her to take risks, how she handled judgment, and what it really takes to build an empire on your own terms. Alicia also opens up about surviving a toxic relationship that nearly derailed her path, and how she found the strength to leave, heal, and rebuild stronger than ever.

Wanna overshare? Apply to be a guest on the show!

https://www.daretoovershare.com

Follow us!

Jackie's socials:

https://www.instagram.com/jackiehollywood

https://www.instagram.com/daretoovershare

https://www.tiktok.com/@itsjackiehollywood

Alicia Waldner's socials:

https://www.instagram.com/aliciawaldner

https://www.tiktok.com/@aliciawaldner

https://www.tiktok.com/@existapp

https://www.instagram.com/theexistapp

]]>b333159a-bdbf-4a91-8624-6b65955bc3b2Wed, 16 Jul 2025 00:00:00 -070042:08truefull1441He Chased Women, Money & Status—Then Chose Celibacy | King HoodieHe Chased Women, Money & Status—Then Chose Celibacy | King Hoodie“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 quiet breakdown that forced him to face himself.

We talk about hyper-independence, ego, toxic love, celibacy as a path to peace, and what healing really looks like when no one else is watching. This isn’t just about faith — it’s about finally asking: who am I without all the noise?

]]>“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 quiet breakdown that forced him to face himself.

We talk about hyper-independence, ego, toxic love, celibacy as a path to peace, and what healing really looks like when no one else is watching. This isn’t just about faith — it’s about finally asking: who am I without all the noise?

]]>c928d226-cb1d-4d81-bac1-4d0b37820257Wed, 09 Jul 2025 08:00:00 -070043:15truefull1331The Dark Side of Being Known Online, Boundaries Beyond the Algorithm | Dare TaylorThe Dark Side of Being Known Online, Boundaries Beyond the Algorithm | Dare TaylorYou 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 figure skating, embracing her inner child, and learning to create for herself — not just the algorithm.

]]>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 figure skating, embracing her inner child, and learning to create for herself — not just the algorithm.

]]>dbadb8cd-fc83-41b4-9518-37134a1ed212Wed, 02 Jul 2025 09:00:00 -070040:35truefull1221Love Island Made Him Famous, But He Still Felt Lonely | Calvin CobbLove Island Made Him Famous, But He Still Felt Lonely | Calvin CobbWhat 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 comforting.

]]>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 comforting.

]]>e6c36c4a-b961-4764-bdf7-6d8ae0e38d1aWed, 25 Jun 2025 10:15:00 -070044:40truefull1111