The Messy Parts

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Why Selling TOMS Destroyed Blake Mycoskie’s Mental Health (And What Saved Him)

July 20, 2026

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 every founder in their 20s and 30s, what Ted Turner told him b...

NYT Writer Susan Dominus: "I Couldn't Risk It"

July 13, 2026

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 fix. Plus: what AI has changed about her reporting, wh...

Gary Vee: Forgiveness, Fear, and the $540 Million Mistake (Replay)

July 06, 2026

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 career killer, and how over-coddling may be delaying independence for an entire ...