What happens when you’re on top of the world—and everything changes overnight? In this raw and unfiltered episode of the Why Not Now? podcast, Amy Jo Martin reunites with entrepreneur, author, and cultural force Sophia Amoruso. This is Sophia's second time on the show, nearly a decade after her first appearance.

From founding Nasty Gal and Girlboss to navigating public scrutiny, financial highs and lows, and deeply personal transitions, Sophia opens up about what she's learned from building (and rebuilding) her life and career.

You will get a rare behind-the-scenes look at the real woman behind the brand, including her thoughts on intentionality, burnout, reinventing your identity, and learning to say "Why Not Stop?" as much as “Why Not Now?”

Sophia shares her approach to time, money, trust, and relationships - with a refreshingly honest take on startup culture, success, and failure.

You’ll also hear about her latest venture, Trust Fund; a disruptive early-stage investment fund, and her unexpected passion for poker, which she’s parlayed into strategic business development. She also shares what she’s learned about ambition, regret, and aging gracefully in the spotlight.

Learn more about Sophia: https://www.sophiaamoruso.com/

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What if your most painful moment could lead to your most meaningful work? In this episode of Why Not Now?, we revisit Amy Jo Martin’s conversation with Scott O’Neil - CEO of LIV Golf and former CEO of the Philadelphia 76ers - one of the most raw and riveting conversations in the show’s history.

A titan in the sports and entertainment industry, Scott shares how a deeply personal tragedy - the loss of his best friend to suicide - became the catalyst for his bestselling book Be Where Your Feet Are and a complete re-evaluation of what matters most.

From leading billion-dollar organizations to navigating family, grief, and growth, Scott talks about embracing vulnerability, managing intensity, and why "balance" is a myth, but presence is everything. He opens up about getting fired from his dream job, redefining success, and how he used 200 cold calls to pivot his career during one of his lowest chapters.

Whether you’re in the thick of a transition, craving more presence in your life, or simply trying to figure out what’s next, this conversation is for you. Scott doesn't just talk about leadership, he embodies it, with heart and humility.

You'll walk away with tools to build resilience, lead with heart, protect your time, and create meaningful connections in your work and at home.

Learn more about Scott: https://www.linkedin.com/in/scott-o-neil/

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In this episode of Why Not Now?, we revisit Amy Jo’s interview with bestselling author, speaker, and global thought leader Mel Robbins - and the conversation is as raw, real, and revelatory as ever.

Mel opens up about her incredible journey from burned-out attorney to one of the most booked female speakers in the world. At the heart of her transformation? A single moment at an Oprah Winfrey event that sparked a visceral reaction and led to a cascade of courageous decisions. Mel shares how she built her powerhouse platform by learning to trust her inner wisdom - and by inventing one of the simplest, most powerful tools for action: The 5 Second Rule.

You’ll learn how to spot your own “Why Not Now?” moments, how to use your energy gauge to make better decisions, and why starting before you're ready might just be the secret to real progress.

From facing bankruptcy to building a seven-figure business, Mel’s story is a masterclass in resilience, clarity, and courage. Whether you're feeling stuck, seeking purpose, or just need a push to get out of your head and into motion - this episode delivers.

Learn more about Mel: https://www.melrobbins.com/

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In this bold and enlightening episode of Why Not Now?, Amy Jo Martin revisits her candid conversation with NYU professor, bestselling author, and entrepreneur Scott Galloway. Known for his unapologetic take on everything from tech monopolies to personal growth, Scott shares the pivotal “Why Not Now?” moment that led him to walk away from a successful life in San Francisco and start over in New York.

You’ll learn how Scott evaluates major life decisions, why failure isn’t fatal (but playing it safe might be), the keys to healthy relationships and a healthy life, and how to build your own "kitchen cabinet" of advisors for navigating change. He also unpacks the role of social media in shaping public discourse, the coming disruption in higher education, and why forgiveness - especially toward yourself - is a cornerstone of resilience.

Whether you're facing a career crossroads, feeling pressure to conform, or simply need a reset in how you approach risk and ambition, this episode delivers both perspective and practical takeaways. Scott’s unfiltered insights and Amy Jo’s thoughtful questions create a conversation that’s as challenging as it is inspiring.

Learn more about Scott: https://www.profgalloway.com/

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In this powerful re-airing of one of Why Not Now?’s most impactful episodes, Amy Jo Martin sits down with the incomparable Glennon Doyle - author of the #1 New York Times bestseller Untamed, CEO and Founder of Treat Media, and one of today’s most vital voices in personal transformation. Glennon opens up about the life-altering “Why Not Now?” moment that began on a cold bathroom floor and led to her sobriety, awakening, and purpose-driven path. With unmatched honesty and grace, she explores what it means to feel all your feelings - especially the hard ones - and why facing life unfiltered is the ultimate act of courage.

Amy Jo and Glennon dig into imposter syndrome, the art of writing, sharing stories when scars are still wounds, and what happens when we stop chasing dirty pink bunnies and start living as the wild cheetahs we were born to be. Glennon also shares raw reflections on control, love, and the lifelong battle with body image, offering solidarity and hard-earned wisdom along the way.

This episode is a masterclass in truth-telling, filled with warmth, depth and revelations that linger long after the final word. Whether you’re navigating change, wrestling with self-trust or simply seeking a spark to live more untamed, Glennon’s words will meet you exactly where you are. Be sure to check out her newest book, We Can Do Hard Things.

Learn more about Glennon: https://glennondoyle.com/

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What happens when a high-achieving doctor and sports chiropractor decides to rewrite the rules of health? Dr Kenna Ducey-Clark, Founder and CEO of HealthStyle by Dr. Kenna, is doing just that.

In this episode, Amy Jo dive's into Dr. Kenna's transformational journey. She spent years working with elite athletes, helping them optimize their performance, but her biggest pivot came when she turned that expertise inward, confronting her own hidden health struggles.

Dr. Kenna shares how a bold Why Not Now? moment at an airport changed her life - leading her to join Renegade and build a groundbreaking approach that blends science, holistic health, and intuitive wellness. Now, she’s on a mission to help high-performing women stop keeping their health challenges a secret and start prioritizing their well-being - physically, mentally, and spiritually.

From working with champion athletes to coaching executives, Dr. Kenna reveals how women can apply an athlete’s mindset to their own lives, extending their "runway" and redefining what it means to truly thrive. She and Amy Jo also tackle why women’s health is broken, the power of listening to your body, and the future of functional medicine as wealth and influence shift into female hands.

If you’ve ever felt like you're pushing through exhaustion, waiting for the right time to prioritize yourself - this episode is your wake-up call and permission to take the first step toward becoming the champion of your own health.

Learn more about Dr. Kenna: https://www.healthstylebydrkenna.com/

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What happens when a world-class athlete, digital innovator, and fearless adventurer decides to pivot? Renegade member Georgia Sapounas, VP of Innovation & Digital at the NBA’s Cleveland Cavaliers, did just that and shares her remarkable journey from elite figure skater to leading digital transformation in sports.

In this episode, Georgia and Amy Jo go deep fast into the power of surrender, bold decision-making, and the Renegade mindset that fuels Georgia’s success. From working at the Olympics to spontaneously traveling the world, Georgia embodies the "Why Not Now?" spirit—proving that trusting your gut can lead to unexpected and extraordinary opportunities.

One of the biggest lessons from Georgia’s story is the importance of trusting your instincts - even when the logical choice says otherwise. She also highlights the power of surrendering to uncertainty, showing that real growth happens when you let go of rigid plans and embrace the unknown.

Finally, Georgia’s approach to innovation - both in her career and personal life - proves that taking small, intentional steps toward new ideas can lead to game-changing results.

If you’ve ever faced a crossroads in your career or life, this episode is for you. Georgia will inspire you to take your next leap!

Learn more about Georgia: https://georgiasapounas.com/

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Meet Bill Shufelt, the visionary co-founder of Athletic Brewing, who transformed a simple “Why Not Now?” moment into a game-changing movement in the beverage industry. Bill shares his incredible journey of leaving a stable hedge fund career to create a non-alcoholic beer brand that’s now leading a cultural shift toward mindful drinking.

In this episode, you’ll hear about a pivotal dinner conversation with his wife that sparked Bill’s bold leap into entrepreneurship, the personal transformation that fueled his passion for moderation, and how he built a brand that’s not just about great beer but about impact, community, and purpose.

Amy Jo and Bill dive deep into the mindset behind disrupting a centuries-old industry, the power of consistency over chaos, and how sticking to his “slow and steady” approach led Athletic Brewing to become a #1 selling beer. These tips alone are a must-have for entrepreneurs.

From navigating investor rejections to becoming a B Corp with a mission, Bill’s story is a masterclass in purpose-driven leadership. Whether you’re an aspiring entrepreneur, a fan of Athletic Brewing, or simply love a great underdog success story, this conversation is packed with lessons on passion, patience, and the power of asking, “Why Not Now?”.

Learn more about Bill and Athletic Brewing: https://athleticbrewing.com/

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