The Messy Parts

Fired at 24. Turned down her dream job at Nike, then took it anyway. Walked into HSN as the eighth CEO in ten years. Mindy Grossman built one of the least likely careers in American business, and in this episode of The Messy Parts she tells Maryam how: leaving college at 19 to move to New York with $1,800, landing her first job by admitting she couldn't take shorthand, buying 2,000 Aeron chairs to prove a broken culture was changin...

Behind every legendary career is an unfiltered human truth. In this special compilation, 20 of our most notable guests—including Mickey Drexler, Samantha Bee, Blake Mycoskie, Bonnie Hammer, Kim Hastreiter, Sally Susman, Sari Botton, and Baked by Melissa—reveal what happens when the PR guardrails come down. From Bevy Smith’s show-stopping mandate to "have sex, a lot of it," to surprisingly vulnerable confessions ab...

Brian Kelly (aka The Points Guy) has been obsessed with credit card and frequent flyer points since childhood. At age 12, his dad challenged him to book a family vacation using only points, and young Brian successfully got his entire family to the Cayman Islands for free. In this episode, Brian tells Maryam about the reality behind his meteoric rise: ruined credit, toxic friendships, launching The Points Guy as a side hustle, becom...

"I don't believe in burnout." That's Laura Mayer, podcast industry veteran and author of Tryhard, explaining why she's never really taken a break: not after a complicated pregnancy, not after quitting a stable executive job at ABC News, not ever. In this candid conversation with Maryam, Laura traces her try-hard tendencies back to a childhood spent tracking her mother's alcoholism, unpacks the false choice between "lean in" hustle ...

"Even your dream job sucks." That's not cynicism — it's the most useful career advice Samantha Bee has. On this episode of The Messy Parts, she tells Maryam what 12 years at “The Daily Show” and running “Full Frontal” actually taught her: that no one hands you management training before you're leading 75 people, that public setbacks feel enormous and matter less than you think, and that the comparison ...

She dug through filthy sub-basements in the Bowery looking for discarded restaurant ware — and built one of New York's most beloved stores. Julie Gaines, co-founder of Fishs Eddy, joins Maryam on the blue couch to talk about 40 years of messy parts: the husband who cheated and left for Florida (then Thailand), the three CEOs who didn't work out, and the MS diagnosis she now calls a "dignity thief." Julie doesn't sugarcoat any...

"They cut me from that team." That's how Columbia women's basketball head coach Megan Griffith opens this episode of The Messy Parts — and it's just the beginning of her story. Megan tells Maryam about growing up a Chinese American kid in a homogeneous Pennsylvania suburb, playing for four different coaches in four years as a student at Columbia, and deciding to pursue a professional basketball career across Finland, Sweden, ...

What really happens after a founder sells their company? Blake Mycoskie built one of the most recognized brands in the world at TOMS — and hit rock bottom the moment he walked away. In this episode of The Messy Parts, Blake talks candidly with Maryam about founder identity, the mental health crisis hiding behind big exits, and why more money and more success never made him feel like enough. He also shares the advice he'd give...

She's a staff writer at The New York Times Magazine, a Yale lecturer, and one of the most celebrated journalists working today. So why does Susan Dominus still feel like she's figuring it out? In a candid conversation with Maryam, Susan gets into the imposter syndrome that nearly stopped her from calling herself a writer, the sibling rivalry that quietly shaped her ambition, and the career regret she wishes she could go back and fi...

In this re-release of one of our favorite episodes, Gary Vaynerchuk opens up to Maryam about fear, self-esteem, forgiveness, AI, leadership, and what he believes is a growing crisis of “late adulthood.” Gary shares why so many professionals feel stuck — not because of burnout, but because of insecurity and unresolved resentment. He breaks down his philosophy on kind candor vs. radical candor, why fear is the real ...

What happens when you walk away from the career everyone expected you to have? Chef Ayesha Nurdjaja was on a path toward law school, working at a prestigious law firm and doing everything “right.” But something was missing. In this episode of The Messy Parts, Ayesha shares with Maryam how she left a promising legal career to pursue cooking, even when her parents stopped speaking to her and everyone around her thought sh...

"No just means not right now." That's the philosophy that kept writer and Oldster founder Sari Botton going through decades of rejection before building one of Substack's most beloved magazines — at age 60. In this episode of The Messy Parts, Sari gets honest with Maryam about the messy middle: the identity searching, the failed attempts, the mean girls that never quite went away, and the moment she finally stopped contorting...

Bonnie Hammer ran 10 networks and two studios at NBCUniversal — but her career didn't start in a corner office. It started cleaning up dog poop on a kids' TV set. In this episode of The Messy Parts, Bonnie gets radically honest with Maryam about the moments that actually shaped her career: being passed over for the top job at NBC, negotiating her way into her own studio, saying yes to WWE when every instinct said no, and buil...

What does it take to build one of New York City's most recognizable social media brands — from scratch, in secret, while working a day job? Subway Creatures founder Rick McGuire tells Maryam the whole story: from working at VH1 and MTV while quietly building Subway Creatures on the side to Pizza Rat, Ed Sheeran, and a very public account hack that brought him to tears and nearly took everything. Rick gets honest about the cha...

Kerry Docherty is a co-founder of Faherty, the surf lifestyle brand she built alongside her husband, his identical twin brother, and her mother-in-law. But behind the sun-soaked brand was a woman quietly carrying the weight of secrets — from childhood, from marriage, and from a business that nearly broke her. In this episode, Kerry opens up to Maryam about growing up in an Irish Catholic household where hard things went unspo...

What if the hardest parts of your life were actually setting you up for something bigger? Assia Grazioli-Venier’s story is a powerful reminder that your worst moments don’t define you — what you do next does. In this episode of The Messy Parts, Assia shares with Maryam her journey through dyslexia, cancer, infertility, and major career pivots — and how she turned every setback into fuel. She opens up about b...

Belle Burden was raised in a family where you simply did not talk about the messy parts. So when her husband left without explanation during COVID lockdown — and then asked her to tell people it was amicable — something in her snapped. In this episode, the New York Times bestselling author of “Strangers” tells Maryam about the moment she chose radical honesty over a managed narrative, and why that single dec...

What does it take to walk away from a six-figure career with no plan, go broke, and come out the other side with a Bravo show, an Amazon Prime series, and a Broadway stage credit? In this episode of The Messy Parts, the one and only Bevy Smith tells Maryam about growing up in Central Harlem, cutting her teeth in luxury fashion advertising, landing at Vibe and Rolling Stone, and then walking away from all of it to start over —...

Joanna Coles built one of the most storied careers in media — from editor-in-chief of Cosmopolitan to running The Daily Beast. So when she says feminism got it wrong, people listen. In this episode, Joanna challenges assumptions about ambition, motherhood, and what a successful life actually looks like. She reveals why curiosity — not ambition — drove every major career move she made, what she wishes someone had t...