The Root of All Success with The Real Jason Duncan
The Real Jason Duncan
328 episodes
5 days ago
Welcome to The Root of All Success with The Real Jason Duncan—a podcast where I uncover the real stories behind today's most successful entrepreneurs, creatives, athletes, artists, and leaders. In every episode, I dive deep into honest, unfiltered conversations that reveal how these trailblazers define success, overcome challenges, and craft transformative strategies to excel in their industries.
I'm not just your host—I'm an entrepreneur behind 12 thriving ventures and the founder of The Exiter Club, a mastermind community dedicated to living #TheExitLifestyle. I built XOS™ (The Exiter Operating System) to empower business owners to transition from the daily grind to becoming strategic owner-investors, creating a life that blends professional achievement with personal fulfillment.
Based in Nashville, Tennessee, my journey—from an 8th-grade history teacher to a serial entrepreneur—has been fueled by a passion for authentic success. Outside of my business interests, you'll find me enjoying motorcycle rides, RV adventures, and cherishing everyday moments with my high school sweetheart of 30 years and our two grown children. My life, both personal and professional, is guided by unwavering faith in Jesus. Tune in on all major podcast platforms and YouTube for actionable insights, fresh perspectives, and inspirational stories that can spark your own journey toward balanced success.
And if you’re feeling overwhelmed or burnt out in your business, visit businessburnouttest.com to take our Business Burnout Test and get personalized recommendations to reignite your passion and transform your life.
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Welcome to The Root of All Success with The Real Jason Duncan—a podcast where I uncover the real stories behind today's most successful entrepreneurs, creatives, athletes, artists, and leaders. In every episode, I dive deep into honest, unfiltered conversations that reveal how these trailblazers define success, overcome challenges, and craft transformative strategies to excel in their industries.
I'm not just your host—I'm an entrepreneur behind 12 thriving ventures and the founder of The Exiter Club, a mastermind community dedicated to living #TheExitLifestyle. I built XOS™ (The Exiter Operating System) to empower business owners to transition from the daily grind to becoming strategic owner-investors, creating a life that blends professional achievement with personal fulfillment.
Based in Nashville, Tennessee, my journey—from an 8th-grade history teacher to a serial entrepreneur—has been fueled by a passion for authentic success. Outside of my business interests, you'll find me enjoying motorcycle rides, RV adventures, and cherishing everyday moments with my high school sweetheart of 30 years and our two grown children. My life, both personal and professional, is guided by unwavering faith in Jesus. Tune in on all major podcast platforms and YouTube for actionable insights, fresh perspectives, and inspirational stories that can spark your own journey toward balanced success.
And if you’re feeling overwhelmed or burnt out in your business, visit businessburnouttest.com to take our Business Burnout Test and get personalized recommendations to reignite your passion and transform your life.
326: From Meta to Menswear: How Anya Cheng Built an AI Fashion Startup
The Root of All Success with The Real Jason Duncan
35 minutes
4 weeks ago
326: From Meta to Menswear: How Anya Cheng Built an AI Fashion Startup
What if AI could solve one of fashion’s biggest problems—waste—while helping men look sharp without ever setting foot in a mall?
In this episode of The Root of All Success, I sit down with Anya Cheng, a Silicon Valley tech executive turned founder of TAELŌR, an AI-powered clothing rental and styling platform for men that’s transforming how fashion meets technology and sustainability.
Before launching TAELŌR, Anya helped build Facebook and Instagram Shopping at Meta, led innovation at eBay and Target, and scaled McDonald’s global food delivery. Today, she’s using AI to make fashion smarter, more sustainable, and accessible to busy professionals.
We dive into how Anya turned a personal frustration into a groundbreaking business model—and what her journey reveals about innovation, leadership, and courage in a male-dominated industry.
💡 In this episode, you’ll learn:
How AI is transforming the fashion industry from waste to sustainability
Why Anya left big tech to build a purpose-driven startup
The mindset shift needed to move from executive to entrepreneur
How TAELŌR uses AI + human stylists to create personalized fashion experiences
The surprising link between style confidence and business success
Why sustainability isn’t just a buzzword—it’s the future of business
Anya’s story is proof that true success starts when you stop chasing trends—and start creating them.
🎧 Watch or listen to the full episode now to discover how innovation, purpose, and sustainability can reshape entire industries.
Who is Anya Cheng?
Anya Cheng is the Founder & CEO of Taelor, an AI-powered men's clothing subscription service promoting sustainable fashion. A Silicon Valley entrepreneur, she has been recognized among "Girls in Tech 40 Under 40" for her expertise in tech product management and marketing.
Anya played a pivotal role in launching Facebook and Instagram Shopping at Meta, led new business expansion at eBay, and helped grow McDonald’s global food delivery. She also shaped Target’s mobile commerce and has led teams in AI, product management, UX, and marketing across Fortune 500 companies.
Her work has earned 20+ prestigious awards, including the Webby Award for Best Shopping App, Best Mobile App Award, and The Communicator Award. A best-selling author, adjunct professor, and two-time TED speaker, she lectures at Northwestern University and 500 Global and is a sought-after keynote speaker.
Anya’s award-winning venture, Taelor, won first place at Draper University’s Startup Competition and was named a Startup to Watch by Bay Area Inno. She holds a Master’s in Integrated Marketing Communications from Northwestern University and an MBA from the University of Chicago Booth School of Business.
Anya Cheng’s Website Link: https://taelor.style/
Anya Cheng’s Social Media Link:
Taelor: https://taelor.style/pages/membership
Anya LinkedIn: linkedin.com/in/anyacheng
Taelor LinkedIn: https://www.linkedin.com/company/taelor/
Taelor Instagram: https://www.instagram.com/taelor.style/
Anya Photo: https://tinyurl.com/anyaphoto
Anya Detailed Bio: https://tinyurl.com/anyasbio
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The Root of All Success with The Real Jason Duncan
Welcome to The Root of All Success with The Real Jason Duncan—a podcast where I uncover the real stories behind today's most successful entrepreneurs, creatives, athletes, artists, and leaders. In every episode, I dive deep into honest, unfiltered conversations that reveal how these trailblazers define success, overcome challenges, and craft transformative strategies to excel in their industries.
I'm not just your host—I'm an entrepreneur behind 12 thriving ventures and the founder of The Exiter Club, a mastermind community dedicated to living #TheExitLifestyle. I built XOS™ (The Exiter Operating System) to empower business owners to transition from the daily grind to becoming strategic owner-investors, creating a life that blends professional achievement with personal fulfillment.
Based in Nashville, Tennessee, my journey—from an 8th-grade history teacher to a serial entrepreneur—has been fueled by a passion for authentic success. Outside of my business interests, you'll find me enjoying motorcycle rides, RV adventures, and cherishing everyday moments with my high school sweetheart of 30 years and our two grown children. My life, both personal and professional, is guided by unwavering faith in Jesus. Tune in on all major podcast platforms and YouTube for actionable insights, fresh perspectives, and inspirational stories that can spark your own journey toward balanced success.
And if you’re feeling overwhelmed or burnt out in your business, visit businessburnouttest.com to take our Business Burnout Test and get personalized recommendations to reignite your passion and transform your life.
