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Dare to Overshare

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by Jackie Hollywood

5.0(2 reviews)
23 episodes
Updated Daily
Accepts GuestsHas SponsorsLocation 🇺🇸
74

Podcast Authority

Beta
GoodBased on show quality, social media presence, reviews, charts, and more
Pod Engine
Quality85
Social97
YouTube76
Engagement32
Learn more

Podcast Overview

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.

Language

🇺🇲

Publishing Since

6/25/2025

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74

Podcast Authority

Beta
GoodBased on show quality, social media presence, reviews, charts, and more
Pod Engine
Quality85
Social97
YouTube76
Engagement32
Learn more
9
Excellent Areas
0
Good Performance
10
Growth Opportunities
excellent
Publishing Consistency
Every 6 days
Performing excellently!
poor
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Recent Episodes

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

July 1, 2026

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

<p>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</p>

Episode thumbnail for Lyric Perez: "Your Word Is Your Wand" — You Want It… So Why Are You Blocking It?

April 22, 2026

Lyric Perez: "Your Word Is Your Wand" — You Want It… So Why Are You Blocking It?

<p>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.</p><p>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.</p><p>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.</p><p>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.</p><p>This conversation is about:</p><p>— unlearning survival mode</p><p>— shifting your mindset and belief systems</p><p>— manifestation + how your thoughts create your reality</p><p>— why your words carry more power than you think</p><p>— healing hyper-independence and learning to receive</p><p>— building a career in entertainment without a traditional path</p><p>— working behind the scenes and not always getting recognition</p><p>— speaking your truth without trying to control outcomes</p><p>— letting yourself evolve, even when it’s uncomfortable</p><p></p><p>Subscribe for more unfiltered conversations on healing, self-worth, relationships, manifestation, and personal growth.</p><p>Jackie’s socials:</p><p>https://www.instagram.com/jackiehollywood</p><p>https://www.instagram.com/daretoovershare</p><p>https://www.tiktok.com/@itsjackiehollywood</p><p>https://www.youtube.com/daretoovershare</p><p>Lyric’s socials:</p><p>https://www.instagram.com/lyricspoetic</p><p>https://www.tiktok.com/@lyricspoetic</p>

Episode thumbnail for Lexy Panterra: “Me? I’m The Ghetto Booty Rapper?” — Industry Advice, Harsh Truths & Misconceptions

April 8, 2026

Lexy Panterra: “Me? I’m The Ghetto Booty Rapper?” — Industry Advice, Harsh Truths & Misconceptions

<p><strong>Everyone thinks she’s the confident girl… but that’s not the full story.</strong></p><p>Lexy Panterra built a viral brand off confidence—while quietly dealing with insecurity, pressure, and the reality of being watched by millions.</p><p>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.</p><p>We get into:</p><ul><li>living with Crohn’s disease (and how it affects her daily life)</li><li>the truth behind her OnlyFans—and why people misunderstand it</li><li>what it’s like being a woman in entertainment dealing with blurred boundaries + unwanted attention</li><li>why she keeps her relationship private in such a public life</li></ul><br/><p>This isn’t the polished version you see online.</p><p>It’s everything behind it.</p><p>—</p><p>Subscribe for more unfiltered conversations.</p>

23 total episodes available

Recent guests on Dare to Overshare

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Calvin Cobb

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Frequently asked questions

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What is Dare to Overshare?

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.

How often does this podcast release new episodes?

This podcast updates daily.

Where can I listen to this podcast?

This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.

Does this podcast accept guests?

Yes, this podcast regularly features guests.

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