The Messy Parts

Fully Clogged: Gary Vee on Forgiveness, Living Fearlessly, and the Reality of AI

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 MomentsForgiveness 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.“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.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.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.The Self-Esteem Conversation Nobody Wants to Have 🧠Gary breaks it down: almost everything — career fear, content paralysis, insecurity — comes back to self-worth.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.Kind Candor vs. Radical Candor 🎯Gary shares his leadership “kryptonite” — struggling with candor — and why he now believes honest feedback must come with kindness.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.Maximizing Joy vs. Maximizing Money 🔥Why Gary doesn’t optimize for profit alone — and how curiosity drives his many ventures.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.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.The Jets Jersey Story 🧵💚Gary shares theSend a textEmail us: hello@themessypartspodcast.com To stay up to date with The Messy Parts and get all the behind-the-scenes content, follow us on Instagram, LinkedIn, YouTube.If you enjoyed this episode, please subscribe, leave a rating and review on Apple or Spotify or where ever you get your podcasts.Thank you for listening.

Driven by Love and Addicted to “What’s Next”: Fashion Insider Sojin Lee

Sojin Lee has built startups, helped scale Net-a-Porter, won fashion industry awards — and watched businesses collapse. In this candid conversation, she opens up to Maryam about public failure, ambition addiction, and choosing love over everything else. From early executive days in luxury fashion to launching ahead-of-its-time ventures, Sojin shares hard lessons about risk, ego, shame, and survival. She talks about losing major clients, navigating market crashes, and confronting identity when success disappears. This episode is for entrepreneurs, founders, and professionals facing career pivots, burnout, or reinvention. If you’ve ever tied your worth to achievement — or wondered who you are without the title — this conversation is for you.Key Moments00:00 – The Myth of Growth Through Failure 💥Sojin reacts to the idea that “growth comes from failure” — and why that’s easy to say but brutal to live through.02:12 – Raised to Be Responsible, Not Seen 🌏Growing up Korean, the eldest of four, constantly translating and adapting — and how that shaped her identity.05:18 – The ‘Joy Luck Club’ Leadership Complex 🍽️Why giving away the biggest piece can turn into over-functioning at work — and quiet resentment.08:05 – Control, Data & the Need for Certainty 📊Why Sojin gravitated toward analytics in fashion — and how control became her survival strategy.13:42 – The Love Story That Changed Her Career ❤️Choosing Net-a-Porter wasn’t just ambition — it was a move driven by love and personal priorities.19:55 – From 5th Row to Front Row at Fashion Week 👠The scrappy early days of Net-a-Porter and the moment the industry finally took them seriously.30:38 – Ahead of Its Time… Then It Collapsed 📉Launching Fashion Air (early live shopping + UGC) — and watching it fall apart during the recession.34:05 – The Shame of Public Failure 😶‍🌫️Why she couldn’t read the press coverage about her startup’s collapse — and the saving-face instinct.36:45 – When Success Becomes Addictive 💰How financial wins and big exits unlock a hunger for more — and why that can be unhealthy.38:52 – COVID, Market Crashes & Losing It Overnight 🌪️Winning the LVMH Innovation Award — then losing major clients and investor backing during global chaos.41:08 – “200 Coffees”: The Comeback Strategy ☕Her practical reset plan: set a mourning deadline, ask for help, and book 200 coffee meetings.45:05 – Adapt or Fall Behind: Why AI Is Non-Negotiable 🤖Sojin’s blunt advice for professionals and founders navigating the next wave of disruption.Send a textEmail us: hello@themessypartspodcast.com To stay up to date with The Messy Parts and get all the behind-the-scenes content, follow us on Instagram, LinkedIn, YouTube.If you enjoyed this episode, please subscribe, leave a rating and review on Apple or Spotify or where ever you get your podcasts.Thank you for listening.

The Man Who Dressed America: Fashion Legend Mickey Drexler

Mickey Drexler built the Gap into a $15 billion empire, created Old Navy, helped redefine J.Crew, and shaped American retail culture. And then? He was fired. No warning. No thank you. Just a card, a sentence, and a door. In this episode of The Messy Parts, Maryam sits down with Mickey to talk about what actually happens when you do everything “right” and still get pushed out. They go deep on instinct vs. pedigree, why big companies break good people, how to recover from a public exit, and the price of loyalty in a system that doesn’t always return it. This conversation is for anyone who’s ever felt underestimated, overlooked, or like they were building something real while everyone else chased politics. If you’ve ever asked yourself, “What do I do now?” — you’re in the right place.Key MomentsFrom $400 Million to $15 BillionHow Mickey Drexler scaled Gap into a global powerhouse — and why he still hates the word “turnaround.” 📈“Adversity Is the Advantage”Growing up in the Bronx, losing his mother young, and how hardship shaped his drive. 💔➡️🔥Why Mickey Trusts People With Hard StoriesWhy he’s drawn to people who’ve struggled — and what today’s work culture gets wrong. 🧠❤️“Business School Is a Waste of Time”Mickey explains why he thinks degrees, grades, and pedigrees don’t equal instinct or success. 🎓🚫The Shy Kid Who Became a CEOMickey opens up about insecurity, introversion, and growing into leadership later in life. 😶➡️👔The $500 Salary Moment That Changed EverythingThe quiet injustice early in his career that taught him how systems really work. ⚖️💸“You Feel It Before It Happens”Mickey describes the instinctual moment he knew he was about to be fired. ⚠️🧭Fired After 18 Years… With a CardHow Mickey Drexler was let go from Gap — no warning, no thanks, just a sentence. 🧾💥“It Was a Gut Punch”Processing rage, humiliation, and self-worth after a public corporate exit. 🥊😞Is There a Right Way to Fire Someone?Mickey explains how leaders should handle endings — and why most fail. 🪑🤝Betting on People: Why Jenna Lyons MatteredHow choosing the right creative partner helped rebuild J.Crew — and what talent really looks like. 🎨✨Advice for Anyone Starting Out Today“Hire your boss. Trust your instinct. If it doesn’t feel right — walk.” 🚪➡️🌱Send a textEmail us: hello@themessypartspodcast.com To stay up to date with The Messy Parts and get all the behind-the-scenes content, follow us on Instagram, LinkedIn, YouTube.If you enjoyed this episode, please subscribe, leave a rating and review on Apple or Spotify or where ever you get your podcasts.Thank you for listening.

From Fired to Fashion Powerhouse: Jeweler Marla Aaron

At what point does a side hustle stop being a hobby? On this episode of The Messy Parts, Marla Aaron tells Maryam the exact moment she realized she could no longer hedge her ambition. What began as a creative outlet eventually became a full-fledged business, but not without years of doubt, rejection, and financial anxiety. In this episode, Marla and Maryam explore the tension between security and risk, why waiting to feel “ready” is a trap, and how fear can coexist with clarity. They also talk about loneliness, creativity, social media as an unexpected unlock, and what it really takes to start over later than planned.Key Moments“So Happy. Not Scared at All.” 😮Marla describes the emotional moment she finally quit her corporate job and why relief outweighed fear.Becoming Comfortable With Discomfort 🌍Marla connects her childhood independence and studying abroad at 17 to her lifelong willingness to take risks.Graduating Into a “Bad Job Market” 📉Why Marla believes focusing on opportunity matters more than economic doom narratives for young professionals.“I’m Scared of Everything.” 😬A candid conversation about fear, impostor syndrome, and doing hard things anyway.Choosing Money Over Passion (At First) 💼Marla explains walking away from journalism due to low pay and financial anxiety.Fired, Divorced, and a Single Mom 💥The emotional and financial rock bottom that forced Marla to keep moving forward.The Boring Job That Funded Creativity 🔄How working a job she didn’t love gave her space to build her dream at night.A Hobby With a Dream 💭How Marla quietly built her jewelry business at night while working full-time and raising a child.“Everyone Told Me I Was Insane.” 🔥The Cannes turning point: burnout, injury, rage, and the final decision to quit.“This Is Not a Hobby.” 🚨The pivotal boardroom moment when a CEO unknowingly pushed Marla to fully commit.Instagram Unlocks the Business How learning social media from her kids helped Marla grow a global direct-to-consumer brand.The Loneliness of Building Something Alone 🧍‍♀️Marla opens up about the isolation that comes with entrepreneurship and leadership.Send a textEmail us: hello@themessypartspodcast.com To stay up to date with The Messy Parts and get all the behind-the-scenes content, follow us on Instagram, LinkedIn, YouTube.If you enjoyed this episode, please subscribe, leave a rating and review on Apple or Spotify or where ever you get your podcasts.Thank you for listening.

Becoming the CEO of Me: Communications Icon Sally Susman

Is it possible to be successful, exhausted, uncertain, and stuck — all at the same time? In this episode of The Messy Parts, former Pfizer communications chief Sally Susman joins Maryam on the blue couch to get real about fear, ambition, burnout, and what it really takes to grow. From being told she’d never have a career after coming out, to leading Pfizer during COVID, to leaving corporate life behind, Sally shares the messy, human moments that shaped her leadership. She talks about the risks of playing it too safe, losing identity when a job ends, and why breakthrough moments rarely arrive when you feel “ready.” This isn’t a highlight reel — it’s a real conversation about pressure, reinvention, and learning to trust yourself through change. If your career looks good on paper but feels heavy inside, this episode will help you feel less alone. Key Moments“Be Ready — You Don’t Know When It’s Coming” ⏳Sally reflects on COVID and shares her core career philosophy about preparation and unexpected breakthrough moments.Growing Up With Privilege AND Pressure 🎭Sally explains what it was like being raised in an ambitious, high-expectation household.“You’ll Never Have a Career” 💔Sally shares the moment she came out to her parents — and the sentence that reshaped her entire life trajectory.“Nothing Scared Me After That” 🔥How that painful family moment became the foundation of her courage and leadership confidence.Leaving Government for Corporate America 🏛️➡️🏢Why Sally walked away from politics — and what frustrated her most about “doing good” in government.“My Heart Was in My Throat” 😰➡️💪Sally explains why fear is her signal for growth — and how discomfort became her career compass.Walking Into Pfizer’s Reputation Wall 🧱The moment Sally realized just how deep public distrust of Big Pharma really ran.COVID Changed Everything 🌍Inside Pfizer’s pandemic pivot — opening labs to media, sharing trial protocols, and racing against time.Finding Her Voice on the Global Stage 🎙️How Sally went from behind-the-scenes operator to public-facing leader during the crisis.Hiring a “Senior Intern” After Watching a Movie 🎬The unconventional idea inspired by The Intern that became a Fast Company cover story.Leaving Corporate Life Was Harder Than She Expected 🚪Sally opens up about identity loss, comfort traps, and preparing for her off-ramp.“I Was Too Transactional” — Career Feedback That Stung 🪞The tough 360 review that changed how Sally approached relationships at work.Advice to 35-Year-Old You: “Worry Less” 🌱Sally’s direct message to stressed professionals navigating pressure and self-doubt.Send a textEmail us: hello@themessypartspodcast.com To stay up to date with The Messy Parts and get all the behind-the-scenes content, follow us on Instagram, LinkedIn, YouTube.If you enjoyed this episode, please subscribe, leave a rating and review on Apple or Spotify or where ever you get your podcasts.Thank you for listening.