What happens when one of the most influential cultural forces of the last 40 years walks into The Stiletto Room? Baby, you get Flavor Flav — rapper, Rock & Roll Hall of Fame inductee, icon, activist, reality TV pioneer, and one of the realest humans alive.

And let me be clear: Flav isn’t just America’s hype man — he’s an American treasure. A living, breathing reminder of what it looks like to turn survival into joy, pain into purpose, and personality into pure cultural impact.

In this electrifying, emotional, hilarious, historic conversation, I sit down with Flav as he takes us from Public Enemy’s early days and his brotherhood with Chuck D, to grief and legacy, to watching politics shift from “fun” to “dangerous.” We talk Ruby Bridges, civil rights, community impact, and yes — Flav sponsoring the U.S. Olympic water polo team (and getting in the pool himself).

Then we go deep: sobriety, relapse, honesty, redemption. Flav opens up about his mom, his guardian angels, and why secrets keep people stuck — and how telling the truth is what sets you free.

And of course… the Taylor Swift era. The friendship bracelets. The “King Swifty” coronation. The kids losing their minds when they see him.

This episode is history, humor, heart, and healing wrapped in a clock the size of a dinner plate. Flavor Flav isn’t just a legend — he’s a lesson in survival, joy, and pure authenticity.

Expect big laughs, real vulnerability, and a reminder that icons aren’t made by perfection—icons are made by impact. Yeah boyyyyy!

About Flavor Flav

Flavor Flav is the most iconic hype man in history and one of the most recognizable legends in entertainment. A musical prodigy proficient in 15 instruments, he rose to fame in the late ’80s as a co-founder of the legendary hip-hop group Public Enemy. Possessing one of the most sampled voices in hip-hop history, Flav and Public Enemy were inducted into the Rock and Roll Hall of Fame in 2013 and received a Lifetime Achievement Award at the 62nd GRAMMY Awards in 2020. Beyond music, Flav became a reality TV phenomenon with Flavor of Love, VH1’s highest-rated show of all time and a defining pop-culture milestone of the era. In 2024, he made headlines worldwide as the first individual to sponsor a U.S. Olympic team, serving as official sponsor and hype man for the men’s and women’s water polo teams through the 2028 Los Angeles Olympics. He continues to use his platform to advocate for mental health, sobriety, humanitarian rights, and women’s sports, inspiring audiences across generations worldwide.

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What happens when one of your closest friends — and one of the most fearless humans you know — sits down in The Stiletto Room? You get Chaz Bono, baby. Actor, activist, producer, trailblazer, and someone I’ve walked through sobriety, transformation, and truth with for decades.

In this raw, powerful, beautifully honest conversation, Chaz opens up about growing up as the child of Sonny & Cher, navigating identity long before the world had language for it, and what it really took to step into himself at 40 years old. We talk about transition, chosen family, the brutal political climate, LGBTQ+ rights, the fear and freedom of hormones, and how activism becomes a lifeline — not a choice.

Chaz shares how acting saved him, how independent horror became his unexpected creative playground, and why living authentically at ANY age is not just possible — it’s non-negotiable.

This episode is for anyone who’s ever felt “different,” anyone who’s ever had to fight for their place in the world, and anyone who believes in living boldly, bravely, and unapologetically.

About Chaz Bono

Chaz Bono is an American character actor and activist, and the only child of famed entertainers Sonny and Cher. He is best known for his work on American Horror Story and Curb Your Enthusiasm. An acclaimed author, Bono has written three books, including NY Times Best Sellers, Family Outing 1998, and Transition published by Dutton in 2011, a candid account of a forty-year struggle to match his gender identity. Adding to his multiple hyphenated talents, he has shared his life and experiences in, and produced the three-time Emmy nominated documentary, "Becoming Chaz."Bono has a rich history of advocating for LGBTQ rights, having worked for two national LGBTQ organizations, and as public speaker on college campuses and at events around the world. He continues to be a strong voice the for LGBTQ community, and is a passionate champion of equality for all Americans, especially those discriminated against and targeted because of race, religion, sex, age, ethnicity, sexual orientation, and gender identity. In 2012 Bono decided to pursue his lifelong dream to have a career as a character actor. He’s guest stared in the films Dirty, Reborn, Three From Hell, Reboot Camp, The Bell Keeper, and Burry The Bride and Little Bites, which he also produced. Bono has also guest starred on American Horror Story: Roanoke and American Horror Story: Cult, Curb Your Enthusiasm, The Bold and the Beautiful.

If you love the topics we unpack in the podcast, then you'll love Dina LaPolt's new motivational book, Street Smart: Succeeding in a Man's World. Order Now!
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There are artists… and then there are American treasures. And today in The Stiletto Room, I sit down with one of the women who shaped my entire life: Melissa Etheridge.

When I tell you her first album catapulted me into my identity, my career, my purpose — baby, that is not an exaggeration. Melissa talks about writing every song herself, getting discovered in a Long Beach women’s bar, breaking through a male-dominated industry, and the moment she realized her authenticity was her superpower long before the world was ready for it.

We talk Grammys, Oscars, touring overseas, her iconic Janis Joplin performance at the Grammys while she was still in cancer treatment, and the spiritual awakening that reshaped her entire life. Melissa opens up about manifesting her dreams — including her new album Rise, her duet with Chris Stapleton, and the foundation she created in honor of her son to revolutionize addiction treatment.

This conversation is about music, resilience, motherhood, activism, joy, and the wild courage it takes to stay authentic for four decades.

Melissa Etheridge doesn’t just inspire — she changes lives. Mine included.

ABOUT MELISSA ETHERIDGE:

Melissa Etheridge is a Grammy- and Oscar-winning rock icon celebrated for her unmistakable vocals, confessional songwriting, and decades of fearless authenticity. She broke through in 1988 with her self-titled debut and became a defining voice of American rock with hits like “Bring Me Some Water,” “Ain’t It Heavy,” “I’m the Only One,” and the Grammy-winning “Come to My Window.”

Her landmark albums Yes I Am and Your Little Secret cemented her place in music history, earning her ASCAP’s Songwriter of the Year. In 2007, she won an Academy Award for “I Need to Wake Up,” written for An Inconvenient Truth. Etheridge has long been a pioneer in LGBTQ+ visibility and cultural impact, famously performing bald at the 2005 Grammys during cancer treatment — a moment that inspired millions.

She’s continued to evolve with acclaimed projects like Memphis Rock & Soul, The Medicine Show, and One Way Out. Her powerful solo show My Window debuted Off-Broadway before opening on Broadway in 2023 to critical praise.

In 2020, she founded The Etheridge Foundation to advance research and compassionate solutions for opioid use disorder. Her 2024 docuseries and live album I’m Not Broken, recorded inside the Topeka Correctional Facility, showcases the profound healing power of music, storytelling, and

If you love the topics we unpack in the podcast, then you'll love Dina LaPolt's new motivational book, Street Smart: Succeeding in a Man's World. Order Now!
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Welcome to a very special Thanksgiving edition of The Stiletto Room, and by special, I mean my children hijacked my show. Yes, baby, this week I’m joined by Buddy, Wilson, and their brilliant (and brutally honest) friend Tallulah Sykes… and let me just say: the turkey is not the only thing getting roasted.

In true holiday spirit, we talk about everything, school trends (including the unholy nightmare known as “pepper yucky”), Shark Tank projects, hummingbird sanctuaries, bullying, politics, superpowers, and why Gen Alpha apparently speaks its own language. I try to keep control, but listen… These kids have more opinions than a Thanksgiving dinner table after dessert.

We get into phones, friendships, football, Broadway dreams, and gratitude, real gratitude. The kind you feel when you look at your kids, their giant hearts, and their growing sense of justice, and realize: yeah, the next generation might actually save us.

This episode is hilarious, chaotic, tender, and full of Thanksgiving heart. A perfect reminder that family, chosen or biological, is messy, loud, loving, and worth every second.

About Wilson, Buddy, and Tallulah

Wilson Ray and Buddy Lee LaPolt are Dina LaPolt’s 12-year-old twin boys. Wilson loves street art, making slime, and going to Sephora. Tallulah is his best friend. Buddy loves playing football and basketball and is a model represented by LA Models Jr. They love animals and all together have three dogs; Elsa, Doodles, and Gatsby.

Tallulah Sykes 11 years old. Born in New York and raised in Los Angeles. Tallulah loves performing, traveling, making slime, and walking her dog, Baxter.

If you love the topics we unpack in the podcast, then you'll love Dina LaPolt's new motivational book, Street Smart: Succeeding in a Man's World. Order Now!
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In this episode of The Stiletto Room, I sit down with one of my favorite people on the planet - Allison Statter, CEO & Founder of Blended Strategy Group and XOa Fragrance, and devoted boy mom. She is the daughter of my dear friends, legendary music executive Irving Azoff and powerhouse matriarch Shelli Azoff, and she is a true baller in her own right.

We get real about what it actually feels like to be stretched in a million directions as working mothers, entrepreneurs, and connectors in an industry that still doesn’t put nearly enough women in the top jobs. Allison talks about what it was like for her growing up Azoff, going on the road in the summers with the Eagles, and how listening in on her dad’s calls and watching her parents build community made the business feel like it was “in her DNA.”

Allison breaks down why authentic partnerships beat clout-chasing every time, how her intuition drives fast, decisive choices for brands, and the unglamorous truth about launching and sustaining a business — from Blended Strategy Group to her signature fragrance line, XOa. I share the wild story of my clair-sentient astrologer’s predictions, and we dive into energy, karma, and the power of trusting your gut.

This episode is a front-row seat to a conversation between two women who love hard, work hard, and refuse to apologize for being both: mothers, bosses, and believers in our own magic.

About Allison Statter

Allison Statter launched entertainment marketing agency Blended Strategy Group in 2015 with her business partner Sherry Jhawar. Allison is a forward-thinker with deep experience in talent management. She spent 10+ years at Azoff Music Management where she managed A-list talent such as Gwen Stefani, Jennifer Hudson, Adam Levine, Jewel and Mariah Carey to name a few. She also led the brand division negotiating major deals with top brands from American Express to L’Oréal, and Weight Watchers among many others. Allison created Blended Strategy to help brands develop integrated 360 marketing initiatives that focus on the unique intersection of brands & talent within pop culture. What started as a celebrity procurement and influencer marketing business now includes Marketing Communications, Social Media and Paid Growth services. BSG’s client roster includes top household names like Shake Shack, Schwarzkopf, OLLY Wellness, and the Radio City Rockettes to talent and founder-led brands like GXVE Beauty by Gwen Stefani, Rael Holistic Cycle Care and Jennifer Meyer Fine Jewelry. Allison currently resides in Los Angeles with her husband and 3 boys.

If you love the topics we unpack in the podcast, then you'll love Dina LaPolt's new motivational book, Street Smart: Succeeding in a Man's World. Order Now!
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What happens when you tell a little girl her voice is “weird”? She grows up to be Morgan Wade — one of the most powerful songwriters of her generation.

In this brutally honest and deeply moving episode of The Stiletto Room, Dina LaPolt sits down with country-rock phenom Morgan Wade to talk about everything — from growing up in small-town Virginia and discovering Elvis, to battling addiction, rebuilding her life, and rewriting the rules of country music.

Morgan opens up about getting sober at 22, the moment that changed everything in New York, and how fitness, discipline, and authenticity became her survival tools. She also talks about the story behind her latest record The Party Is Over (Revisited), her Guinness World Record pull-up goal, and the next chapter of her creative empire.

This is Morgan like you’ve never seen her — raw, grounded, and powerful as hell.

About Morgan Wade

Virginia-born singer-songwriter Morgan Wade has carved out a reputation as one of country music’s most authentic and fearless voices. After breaking through with her debut album Reckless and earning nominations from the Academy of Country Music and Americana Music Association, Wade found herself longing for simplicity amid the chaos of fame and touring.

That search for clarity fuels her latest album, Obsessed—a raw, 14-track project written entirely by Wade and produced by her guitarist Clint Wells. Returning to her roots as a storyteller, the record captures themes of love, home, heartbreak, recovery, and self-reflection. From the driving opener “Total Control” to the soulful “2AM in London,” Wade balances the ache of distance with the pull of connection.

Highlights include “Moth to a Flame,” a testament to lasting love; “Juliet,” a reimagined tale of forbidden affection; and “Walked on Water,” a stirring duet with Kesha that showcases Wade’s emotional depth, lyrical honesty, and vocal power. Through Obsessed, she chronicles growth, vulnerability, and a reckoning with her past—emerging renewed, grounded, and unapologetically herself.

Wade’s evolution proves why she remains one of modern country’s most compelling artists, blending country, Americana, and rock influences into bold, honest storytelling that continues to resonate deeply with fans. Her music speaks to resilience, redemption, and the courage to face change head-on—a reflection of her personal journey toward balance, healing, and artistic freedom.

If you love the topics we unpack in the podcast, then you'll love Dina LaPolt's new motivational book, Street Smart: Succeeding in a Man's World. Order Now!
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What happens when the daughter of a rock legend decides to write her own story?

In this powerful and emotional episode of The Stiletto Room, I sit down with Jesse Money, daughter of the late, great Eddie Money — my former client and dear friend — to talk about love, loss, recovery, and finding her voice as an artist and woman.

We go deep: from life on the road with her dad and the family band, to how the Real Money TV show came to be, to the heartbreak of losing both her father and grandfather — and finding sobriety in the middle of it all. Jesse opens up about carrying her father’s legacy through her new music, her stunning new song “Legacy”, and the moment Eddie told her, “I’m leaving you with my legacy.”

This conversation is raw, real, and full of heart — about breaking cycles, honoring family, and finally stepping into your own light.

Jesse Money’s Bio:

Jesse Money is a singer/songwriter and the daughter of Rock legend Eddie Money. Jesse grew up in the music business, touring alongside her Dad and singing on stage with him since she was a little girl. Her vocal influences range from Etta James to Janis Joplin, Paul Rodgers, and many more, including of course her dad. Jesse's new music is an expression of her journey while going through the different stages of the grief that she experienced after losing her father. Each song on her EP expresses all of the emotions of loss that she went through, while also trying to break through her addiction to drugs and alcohol. Jesse hopes to reach others that are going through similar journeys by sharing her story . Her Rock/Pop sound is raw and soulful, while showcasing the pain and resilience through her songs.

Jesse continues to honor her father’s legacy by paying tribute to his music and performing his songs onstage alongside her brother Dez.

If you love the topics we unpack in the podcast, then you'll love Dina LaPolt's new motivational book, Street Smart: Succeeding in a Man's World. Order Now!
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What do you do when everyone tells you you’re crazy for leaving a cushy executive job to run a haunted hayride? If you’re Melissa Carbone, you go all in—and end up creating what becomes the largest Halloween-themed entertainment company in the world.

From building LA’s iconic Haunted Hayride out of her own front yard to securing the biggest Shark Tank deal in history with Mark Cuban, Melissa has redefined immersive entertainment. She now co-owns Thirteenth Floor Entertainment Group, runs attractions across 19 markets, and continues to innovate in live experiences.

In this episode of The Stiletto Room, Melissa opens up about her early days in Connecticut, the power of believing in yourself, being a gay woman breaking into a male-dominated industry, and how failure became her superpower. She also teases her next project—an unprecedented event coming to Los Angeles that will be the biggest of its kind.

This is a masterclass in risk-taking, resilience, and creativity.

Melissa Carbone Bio:

Melissa Carbone is an entrepreneur, best-selling author, and owner/producer at Thirteenth Floor Entertainment Group (TFEG), the largest themed entertainment company in the world. After a decade leading major markets for Clear Channel Media + Entertainment (now iHeart), Melissa founded Ten Thirty One Productions (TTO), the first company to create and produce live horror attractions. She made history on ABC’s Shark Tank with the show’s largest deal, partnering with Mark Cuban and later Live Nation. After selling TTO, she launched Tailgate Fest and Dirt Road Entertainment, while publishing her best-selling book “Ready, Fire, Aim: How I Turned a Hobby into an Empire.” TTO’s LA Haunted Hayride became one of the country’s top independent haunted attractions before Melissa sold the company to TFEG in 2018. Today, TFEG operates in 16 markets with more than 20 attractions, drawing millions of visitors annually to its immersive entertainment experiences. Her Tailgate Fest redefined the country music festival scene, featuring Toby Keith, Florida Georgia Line, Brett Eldredge, Nelly, and Hardy. During the pandemic, she partnered with LA County Parks to produce the first Drive-In Movie Series and launched Boat Cinema, a sellout hit that earned the 2022 “Best Experience” Award. Featured in Forbes, Fortune, Billboard, Rolling Stone, Entrepreneur, Inc., and Bloomberg, Melissa is recognized as a pioneer in immersive entertainment. She lives in Los Angeles with her dogs Macy, Gwen, and Gayle, and loves horror films, country music, and fitness.

If you love the topics we unpack in the podcast, then you'll love Dina LaPolt's new motivational book, Street Smart: Succeeding in a Man's World. Order Now!
https://a.co/d/6sGKcer

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