The Stiletto Room

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 pu...

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 w...

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 ...

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 ...

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 dir...

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 ru...

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...

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 entertainme...

You’ve seen the helmet, you’ve heard the music—but you’ve never heard deadmau5 like this. In this episode of The Stiletto Room, Joel Zimmerman (aka deadmau5) sits down with me for a rare, unfiltered conversation about his journey from taking apart TVs as a kid in Ontario to headlining festivals across the globe.

Joel opens up about teaching himself computer music before the Internet, creating his own opportunities, and how a fried m...

What happens when a Florida girl with zero connections hops off a plane at LAX convinced she’s “arrived”? If you’re Alexis Fisher, you turn that delusion into destiny.

From unpaid internships and 6:45 a.m. calls with Hollywood legends, to being one of the first to take YouTubers seriously at Maker Studios, Alexis saw the creator economy coming before anyone else. That leap of faith became Timeline Management, the company she founded...

When Tee Kissen walks into the room, the vibe shifts—high frequency, high standards, and high heels. She’s the actress, artist, model, entrepreneur, and unapologetic original behind the viral mantra: “Bad bitches got feelings.”

In this episode of The Stiletto Room, Tee opens up about her new single “Bad”, blending R&B and pop with raw vulnerability, and why independence has always been her power play. We get into everything��her...

What happens when two badass songwriters get a $4.78 royalty check for a global hit? They start a revolution.

In this episode of The Stiletto Room, I sit down with my dear friends Kay Hanley (Letters to Cleo, “Here & Now”) and Michelle Lewis (Cher, Little Mix, Andra Day) to revisit the wild story of how we founded SONA (Songwriters of North America). From walking into my office with questions, to organizing hundreds of writers o...

Jason Lee is not here to play small — and he never has. From surviving foster care and gun violence to becoming Vice Mayor of Stockton and founder of Hollywood Unlocked, Jason’s life is a masterclass in using street smarts, grit, and unapologetic truth-telling to shake up every room he enters.

In this episode, we go all in: how he went from labor organizing and taking on corrupt unions to building one of the most influential media p...

What do Jessica Alba, Hollywood’s elite, and my own face all have in common? Shani Darden. She’s the esthetician-turned-entrepreneur who went from rolling around in music videos to creating the go-to skin care line trusted by celebrities and Sephora shoppers worldwide.

In this episode of The Stiletto Room, Shani opens up about her journey from a small town in upstate New York to becoming one of the most respected Black female founde...

What does it really take to survive—and thrive—in the music industry? In this episode of The Stiletto Room, I sit down with two of the most brilliant (and brutally honest) hitmakers in the game: Bonnie McKee (the pen behind Teenage Dream, California Gurls, Roar) and Shane Stevens (the voice behind American Honey, Fancy Like, and countless Nashville gems).

We go way beyond the highlight reel. Bonnie opens up about losing her first re...

Tinashe doesn’t just walk into a room, she floats in like she owns it, crystals in one hand, hit records in the other. From dancing at age four to leading a girl group, and ultimately carving out her own lane as a fearless solo artist, she’s lived a lifetime before most people finish high school. In this episode of The Stiletto Room, we get into it all: the freedom of creating her early mixtapes, the perfectionism that still drives...

When Prophet speaks, entire rooms shift. From being slammed to the ground by police at just 13 years old to becoming the co-founder and president of the Black Music Action Coalition, Prophet has spent his life turning trauma into transformation. In this episode of The Stiletto Room, I sit down with Prophet to trace his journey—from grabbing a megaphone in the Bronx to standing shoulder-to-shoulder with lawmakers on Capitol Hill.

We ...

When Siedah Garrett walks into a room, legends stop and listen—literally. She’s the Grammy-winning, two-time Oscar-nominated force who penned “Man in the Mirror” for Michael Jackson, sang alongside the greats, and turned every “you can’t” into “watch me.” In this episode of The Stiletto Room, we go way beyond the headlines. Siedah gets real about growing up in constant motion, dodging eviction notices every nine months, finding mus...

Welcome to The Stiletto Room—the unfiltered chat show where no topic is off-limits. I’m Dina LaPolt, entertainment attorney, advocate, and tenacious trailblazer. Each week, I sit down with creative visionaries, iconic disruptors, and unapologetic originals to dive deep into work, life, love, LGBTQ+ journeys, social justice, and everything in between. 

So, grab a seat, get comfortable, and let’s get real. Baby, this is The Stile...