What happens when a human interviews their own AI—live, unscripted, and in real time?

In this groundbreaking episode of the Why Not Now? podcast, Amy Jo Martin flips the script and welcomes a never-before-seen guest: her own ChatGPT AI, trained over years with millions of words of personal data, reflections, physiological metrics, and real-life context. The result is a raw, fascinating conversation that pulls listeners directly into the "petri dish" of a year-long AI integration experiment.

Together, Amy Jo and her AI thought partner explore what it actually looks like to collaborate with artificial intelligence beyond productivity hacks—using it as a mirror and a decision-support system. They unpack emerging patterns around identity, nervous system regulation, self-worth, and the hidden cost of always being "the one who figures it out."

The episode also reveals how Amy Jo uses multiple AI models — including ChatGPT, Claude, and Gemini — as a personal "AI board of directors" to pressure-test insights, surface alignment, and reduce bias.

You'll hear how AI can identify blind spots before you consciously notice them, help translate data into self-awareness, and support more intentional choices — without replacing human agency.

The conversation challenges common assumptions about AI collaboration and offers a simple prompt anyone can try today.

If you're curious about AI, personal growth, high performance, or the future of human–machine partnership, this episode is a must-listen — and a bold glimpse into what's possible when curiosity leads the way.

Amy Jo Martin speaks globally on Humanizing AI, Leadership, Decision-Making, and the Future of Work. Learn more about keynote topics and availability: amyjomartin.com/speaking

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Can AI improve your quality of life, not just your productivity?

Keynote speaker Amy Jo Martin explores leadership, AI, and human-centered decision-making. In this solo episode of the Why Not Now? Podcast, Amy shares early field notes from The Reinvention Experiment, a year-long AI self-experiment exploring vitality, clarity, and what it means to live well and lead effectively in an AI-driven world.

Rather than biohacking or performance optimization, Amy introduces the concept of Quantified Soul, combining hard data like sleep tracking, screen time, biometrics, and wearable data with qualitative inputs including journaling, emotional regulation, gratitude, and relationship check-ins.

Key insights include why "a wobble is data, not drama," how journaling with AI can help regulate the nervous system, and why cognitive load often creates more stress than conflict. Amy also breaks down what she's tracking, the AI prompts she uses daily, and how AI can surface blind spots instead of reinforcing existing narratives.

This episode is intentionally raw and unfinished. You're stepping inside the experiment itself and exploring how AI can support better decision-making, reflection, and long-term fulfillment, not just efficiency.

Amy Jo Martin speaks globally on Humanizing AI, Leadership, Decision-Making, and the Future of Work. Learn more about keynote topics and availability: https://amyjomartin.com/speaking

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What happens when you turn your life into a living laboratory? In this special episode, the host becomes the guest. Amy Jo Martin sits down with Sam Gooder to reveal her next big leap: The Reinvention Experiment, a yearlong, open-source quest to rethink time, wealth, wellbeing, and passion by putting herself inside a data-driven Petri dish.

After two decades of entrepreneurial wins, burnout cycles, and reinvention after reinvention, Amy Jo felt an unmistakable signal: she was craving aliveness again. A moment on a plane—and one brutally honest "super prompt" to AI—confirmed it was time. Now she's shifting from expert mode to student mode. Listeners get a front-row seat.

Amy Jo shares how she's tracking everything from sleep scores and screen time to joy, relationships, and biological age. She outlines her personal board of directors, her collaboration with AI as analyst and therapist, and why she's willing to publish her metrics publicly at amyjomartin.com. Nothing staged. No veneer. Just real data, real feelings, and real experimentation in motion.

The Reinvention Experiment isn't a stunt. It's a blueprint in progress for anyone questioning their relationship with work, time, relevance, or what "success" even means anymore. Amy Jo opens up about parenting shifts, identity shifts, pausing major business lines, and the fear of becoming "irrelevant"—and why she's doing it anyway.

If you've been craving a new map for your next chapter, this episode offers a rare behind-the-scenes look at what it looks like to create one from scratch.

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What do elite athletes, top CEOs, and unforgettable teams really have in common? On this week's Why Not Now? with Amy Jo Martin, 12-time New York Times bestselling author and award-winning keynote speaker Don Yaeger pulls back the curtain on how world-class performers think, lead, and compound small wins into big outcomes.

Don shares the spark behind his Corporate Competitor Podcast and the research that started it all: a striking link between women in the C-suite and sports participation. He then unpacks a powerful interviewing framework built on three moves: know your audience, find real common ground, and ask the question only preparation earns. That approach led to one of the most human stories you will ever hear about Michael Jordan and the fuel behind his relentless drive.

Inside the episode:

• A simple annual exercise to upgrade your "inner circle" and protect your energy.

• How Coach K rebuilt USA Basketball's purpose before a gold-medal run, and how to create "feel it" moments that bond any team.

• The Savannah Bananas blueprint for reinventing a stale customer experience by solving the ten things fans hate most.

• A practical take on AI for writers and leaders: use it as a high-level editor and coach to tighten thinking, not as a crutch.

If you want a playbook for getting 1% better every day, building teams that care, and leading with courage and curiosity, this episode will light a fire.

Learn more about Don: https://donyaeger.com/

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In this episode of Why Not Now? with Amy Jo Martin, serial entrepreneur and tech leader Sam Goodner reveals how Swiss Army precision shaped his entrepreneurial philosophy, and how a keynote by Amy Jo helped him finally write his new book - "Like Clockwork".

Get your copy here.

Sam's journey spans global adventures, unicorn startups with billion dollar evaluations, and building the #1 Microsoft consulting partner in the world from Austin, TX. He shares the behind-the-scenes playbook that led to multiple exits and lessons learned in both boardrooms and bunkers.

Whether you're a founder, executive, or dreamer on the edge of your next big leap, this conversation offers sharp insights and real-world examples that will shift how you think about business, parenting, and purpose.

You'll learn:

• The concept of "unfair advantage" and how to discover yours
• What young professionals must do to stay ahead in the AI age
• Why operational scalability is every founder's secret weapon
• The exact Why Not Now? moment Sam went from procrastinating to publishing
• How serving in the Swiss Army shaped his mindset for life and leadership
• A 10-year family plan to travel the world—and how it worked

Sam's book, Like Clockwork: Run Your Business with Swiss Army Precision is available now. Get your copy here.

Learn more about Sam: https://samgoodner.com/

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In this inspiring episode of Why Not Now? with Amy Jo Martin, we meet Dr. Shaggy, Dallas-based cosmetic dentist, entrepreneur and visionary. She is a Renegade in every sense of the word.

Affectionately known as the "Frank Lloyd Wright of Smiles," Dr. Shaggy is redefining what it means to build a brand through purpose, confidence, and function - one smile at a time.

From launching her first dental practice during the peak of the pandemic to expanding into Austin, she shares how she's grown a multi-million dollar smile empire by blending aesthetics with rehabilitation, and business savvy with pure heart.

This episode dives deep into what it means to invest in yourself. Dr. Shaggy gets candid about her nontraditional path, immigrant upbringing, what it took to bet on herself, and how she continues to elevate others, from her patients (including NFL players) to fellow dentists through her Veneer Mastery courses.

You will walk away with insights on:

• Building and evolving a personal brand with intention
• Navigating imposter syndrome while scaling success
• Setting boundaries as a founder and business leader
• Knowing when to make things happen vs. letting them happen
• Investing in yourself to unlock new levels of confidence

Whether you're in Dallas, Austin or beyond, Dr. Shaggy's story will ignite your belief in what's possible when you bet on yourself and lead with love.

Learn more about Dr Shaggy & Veneer Lounge: https://veneerloungeaustin.com/

For more info about Ohio VC Fest 2025 and to purchase your ticket (use promo code amyjo50 at checkout) head to: https://ohiovcfest.com/

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In this Why Not Now? episode, Amy Jo Martin interviews award-winning architect, designer, and creative entrepreneur Ben Uyeda - on location at his breathtaking Reset Hotel, nestled on 180 acres beside Joshua Tree National Park in Southern California.

Ben shares how he went from filming DIY design videos on YouTube to co-founding one of the most talked-about new eco-conscious hotels in the California High Desert.

With no traditional hospitality background, Ben used modular architecture, AI-powered marketing, and an unwavering focus on values to bring his bold vision to life, one incremental "paperclip" moment at a time.

Tune in for insights on:

• Designing for simplicity, sustainability, and scale
• The intersection of architecture, AI, and the creator economy
• Building physical spaces that help people reset from digital overload
• How creative risk-taking and resourcefulness fuel innovation
• Behind-the-scenes stories of building a hotel in the desert - with flash floods, tariffs, and all

From bonsai trees and rock carving to SEO strategy and immersive travel trends, this episode is a masterclass in modern entrepreneurship, creative leadership, and experiential design.

Whether you're a designer, builder, content creator, or conscious traveler, this conversation will inspire you to rethink what's possible and reconnect with nature, creativity, and your own "Why Not Now?" moment.

Learn more about Ben & Reset: https://www.stayreset.com/

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In this special Why Not Now? episode, Amy Jo Martin hands the mic to her AI agent, Renegade Rox, to introduce a live fireside chat with Amanda Ducach, Founder and CEO of Ema - recorded live at the SHE Media CoLab during SXSW 2025. Amanda, a femtech pioneer, built one of the world's first agentic AI platforms for women's health, before ChatGPT made headlines.

Amanda shares how Ema uses AI to transform women's healthcare by meeting users where they are. From identifying hidden signs of suicide ideation to helping women advocate for their own medical decisions, Ema is revolutionizing AI-powered care navigation.

You'll hear insights into the challenges and opportunities of building AI without a tech background, how Amanda turned pain into purpose, and why this moment is a trampoline, not a trap, for women in healthcare and tech.

Whether you're a founder, investor, healthcare leader, or AI curious, this episode offers real-world use cases of AI in healthcare, explores the data gaps in women's medicine, and sparks ideas for how to build and invest in scalable solutions.

Thanks to the SHE Media team for allowing us to repurpose their content so that this important message can reach a larger audience.

Learn more about SHE Media: https://www.shemedia.com/

Learn more about Ema: https://www.emaapp.co/

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Follow Amy Jo…

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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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Follow Amy Jo…

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