Dare to Overshare

Why do smart, self-aware women stay in toxic relationships even when they know they deserve better? In this episode of Dare to Overshare, bestselling author and relationship coach Sabrina Bendory joins Jackie to break down the psychology behind toxic love, love bombing, narcissism, attachment styles, dating anxiety, self-worth, and why unhealthy relationships can feel so addictive. Sabrina opens u...

If you’ve heard of Neville Goddard but have no idea where to start, this episode is for you. I’m breaking down 8 of his most popular manifestation techniques — including Living in the End, SATS, Revision, I Remember When, Mental Diets, the Lullaby Method, and more — and explaining how to actually use them in real life. A lot of these techniques sound similar because they all fall under one main id...

You may know Kyland from Big Brother, The Challenge, and The Amazing Race, but in this episode, we get into the person behind the competitor. Kyland opens up about being diagnosed with autism as an adult, living with ADHD, masking in social situations, and looking back at some of his biggest reality TV moments with a completely different understanding of how his brain works. We also get into commu...

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...

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 de...

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...

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 m...

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 c...

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 strugglin...

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...

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 language...

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...

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...

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 t...

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 T...

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 war...

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 tr...

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 – Da...

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 exp...

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...

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,...

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...

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....

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, boundari...

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 judgm...