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 before he made his first billion, and how healing his "core wound" changed his relationships, his parenting, and the way he builds companies today.
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Key Moments

02:15 - Why Blake Broke His 3.5-Year Social Media Silence 📱
After years of suffering quietly and feeling ashamed, Blake explains what finally pushed him to publish that vulnerable LinkedIn post.

6:24 - Naming the Core Wound 🔍
Blake identifies the belief that secretly drove every business he ever built: that he was never enough, and that the only way to earn love was to keep proving himself.

10:18 - How TOMS Was Really Born 👟
Blake tells the origin story — a simple idea hatched in Argentina, started out of his Venice Beach apartment with no investors and no business plan, that grew into a huge movement.

12:24 - The Night He Got a Nelson Mandela Award and Felt Terrible 🏆
One of the most striking moments in the episode: Blake describes receiving one of the biggest honors of his career and calling it one of the worst nights of his life.

15:20 - What Blake Would Tell Every Founder Before a Big Exit 💡
Hard-won advice: make sure you have something meaningful to pour your energy into on the other side — because the dopamine drop is real, and snowboarding only lasts so long.

21:45 - What Depression Actually Feels Like 🌊
Blake offers one of the most accessible descriptions of depression you'll hear: like really bad jet lag — knowing you should be awake, but being unable to move.

26:39 - What Ted Turner Told Blake Before He Made His First Billion 🏔️
In a private green room moment at the UN, Ted Turner warned Blake that when he reached the top of the mountain, the chest would be empty.

29:25 - How Healing Changed His Relationship With His Kids 👨‍👧‍👦
Blake reflects on a painful realization: that for years, his own "not enough" wound was being projected silently onto his children.

36:45 - The Advice He'd Give His 30-Something Self 🎯
Blake's closing wisdom: do something you genuinely love in your 20s and 30s, because true financial freedom almost always follows mastery — not the other way around.

37:32 - The Send-Off 💛
Maryam closes with three words that land differently after everything Blake has shared: "You are enough."

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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, why she thinks Substack isn't enough, and the advice she gives every student who wants to break into media. If you've ever played it safe when you knew you shouldn't have — this one's for you.
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Key Moments

01:28 - The Psychology Behind the Byline 🧠
Susan explains why people tell journalists things they've never told anyone else, and why being truly seen is rarer than we think.

03:15 - The Bookish Kid Who Pretended to Read 📚
Susan paints a vivid picture of her Westchester childhood — the youngest of three, already pretending to read before she could, and processing her entire emotional life through books.

09:29 - The Piano Teacher Ultimatum ⏰
Her piano teacher forced a choice: piano or the school newspaper. Susan didn't hesitate for a second.

13:07 - Imposter Syndrome at Yale 😰
Getting into Yale didn't cure the self-doubt — it deepened it. Susan opens up about feeling like a "pretty average suburban kid" surrounded by legacy admits, children of academics, and people she found genuinely intimidating.

14:25 - "I Couldn't Risk It" 😶
Susan admits she avoided Yale's competitive writing classes entirely, not because she wasn't interested, but because she was too afraid to find out she wasn't good enough.

21:13 - The Good Girl Who Waited Until 30 ⏳
Despite always wanting to be a writer, Susan spent her entire 20s as an editor — partly for job security, partly to please her parents.

27:08 - How AI Changed Susan's Entire Reporting Process 🤖
Susan goes from AI skeptic to convert in real time. She breaks down exactly how she used NotebookLM and Google Gemini on her most recent NYT piece, and why she can't imagine going back to the way she did her job before.

30:17 - The Wasserstein Book Origin Story 📖
Susan traces her obsession with the famous Wasserstein family, and reveals the question that consumed her childhood: what would it feel like to grow up in a family where someone tells you "the sky's the limit"?

33:42 - The Limits We Put on Ourselves 🪞
Maryam holds up a mirror: Susan has won Pulitzers, teaches at Yale, and writes for the NYT Magazine — and yet she still talks about herself like someone playing it safe.

40:24 - The Twitter Regret She Can't Shake 🐦
Susan confesses that when the NYT begged her to tweet out her column back in 2011, she was too uncomfortable with self-promotion. Her advice to young journalists: get on the edge of what's new, even when it scares you.

43:11 - What She’d Tell Her 30-Something Self 💡
Susan closes with a deceptively simple piece of wisdom: if something new is forming around you at work, stop wishing it away and get involved.

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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 generation. From parenting teenagers to leading thousands of employees, Gary explains why self-worth is the operating system behind success — and why forgiveness (especially of yourself) might be the most underrated personal development tool of all. If you’ve ever felt behind, afraid to pivot, or unsure of your next move in the age of AI, this episode is for you.

Key Moments

00:00 — Forgiveness Is the Answer We’re Avoiding ❤️‍🩹
Gary opens with a bold claim: most people are emotionally “clogged” because they’re holding resentment. He explains why forgiveness — especially forgiving yourself — may be the most underrated growth tool.

02:46 — “Nice Guys Finish First” 🏆
Gary unpacks the tension between competitiveness and kindness — and why he believes you can be fierce in business without losing your humanity.

05:17 — The Late Adulthood Crisis 🚨
Are we raising adults who aren’t ready to be adults? Gary shares his controversial take on over-coddling, privilege, and why independence matters more than ever.

08:52 — Why He Doesn’t Fear AI (And You Shouldn’t Either) 🤖
Using historical pattern recognition, Gary explains why AI is just the next evolution — not the apocalypse.

14:18 — The Self-Esteem Conversation Nobody Wants to Have 🧠
Gary breaks it down: almost everything — career fear, content paralysis, insecurity — comes back to self-worth.

15:33 — The Rejection He Was Actually Afraid Of 💔
Despite fearless business moves, Gary admits he was afraid to ask girls out in high school. A revealing look at how fear shows up in unexpected places.

18:38 — Kind Candor vs. Radical Candor 🎯
Gary shares his leadership “kryptonite” — struggling with candor — and why he now believes honest feedback must come with kindness.

28:57 — Walking Away From the Family Business 🏪
After building his dad’s liquor store into a $65M company, Gary explains why leaving wasn’t guilt — it was growth.

31:14 — Maximizing Joy vs. Maximizing Money 🔥
Why Gary doesn’t optimize for profit alone — and how curiosity drives his many ventures.

33:35 — Call Your Mom. Forgive Yourself. 📞
One of the most emotional moments of the episode. Gary urges listeners to make the call — to forgive others or themselves.

43:53 — At What Age Do You Stop Blaming Your Parents? 🧨
Gary poses a provocative question: when do you fully own your life? A raw discussion about responsibility and adulthood.

47:46 — The Jets Jersey Story 🧵💚
Gary shares the powerful story of his mom knitting him a Jets jersey when they couldn’t afford one — and how that shaped his confidence forever.

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Email us: hello@themessypartspodcast.com

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Thank you for listening.