Essential listening for anyone romanticizing startup life, founders considering outside funding, people in major transitions, and anyone who needs to hear the whole truth about building and letting go.

Everyone celebrates the start-up. The acquisition. The big payday. But nobody talks about what it actually costs to sell something you poured your soul into. Or the fact that when you take venture capital, you're signing up for an outcome you might not want.

Ashley Mills co-founded obé Fitness after leaving a successful career at CAA. She created a fitness platform before digital fitness was a thing, raised millions, and then it was time to sell. Not because the business failed, or because she necessarily wanted to, but because that's the trade you make with venture funding.

This conversation is honest in ways most entrepreneurship stories aren't. About the corners outside investment can back you into. About choosing purpose over profit and still ending up in a transaction. This is ultimately about the liminal space - when you're left asking who you are without the thing you built.

Listen Below Or Enjoy On Your Favourite Podcast App

• Apple Podcasts
• Spotify
• Youtube

Covered In This Episode

• When a successful lifestyle job stops being compatible with the life you're actually living.

• The relationship between humility and power in the people who achieve lasting success.

• Why thriving in chaos might be a strength rather than something to fix.

• The inevitable end that comes with raising venture capital and what nobody tells you about it.

• How selling a business you built feels like selling your own child.

• The liminal space after an exit, when you're left asking who you are without the thing you created.

• What it means to be a clean channel for ideas that are ready to find their host.

• Why following intuition over logic might be the only way truly transformative work happens.

• The difference between building a business to sell and building something you're called to create.

Chapters

00:00 Welcome to The Courageous Pivot Podcast
03:53 Ashley's Early Dreams
11:52 From Talent Agent To Founder
16:12 Building the obé Fitness Experience
23:11 Funding And Growth
27:39 COVID Chaos
32:33 Venture Capital Pressure And Exit
33:27 Profitability Versus Growth
40:02 Selling And Letting Go
44:18 First Months After Exit
45:53 New Work And AI Consulting
54:40 Creativity As Healing
56:53 Staying Open In Transition 

Special Offers

• Free Heart Coherence Masterclass – A complimentary session with Meghan Telpner exploring how to create alignment between your heart and mind, access inner calm, and live from your most authentic self.

• Click here to get 30% off Rise & Shine: A Guided Approach To Heart-led Living and Leadership. (Click here if you reside in Canada)

Related Episodes

• EP 013: Why Releasing What You Built Could Be Your Greatest Move — For anyone wrestling with the question of when letting go becomes the path forward

• EP 015: Tenacity for Ongoing Reinvention with Chef and Author Christine Flynn — For anyone who knows reinvention isn't a one-time event but an ongoing practice

• EP 021: A Creative Pivot: Why Being Good at Something Isn't Enough with Textile Artist Jen Arron — For anyone discovering that mastery alone doesn't equal fulfillment

Links + Resources

• James Turrell — Contemporary light artist whose work inspired obé's aesthetic

• Dan Flavin — Light artist known for fluorescent installations

• CAA (Creative Artists Agency) — The talent agency where Ashley spent a decade before founding obé Fitness

• EBLI (Evidence-Based Literacy Instruction) — Nora Chahbazi's evidence-based reading program that Ashley used for her son

• The Truth About Reading — Documentary about dyslexia and reading instruction that led Ashley to EBLI

• Happy Medium — New York art cafe where you create art while enjoying food and drinks

More About Ashley Mills

• Ashley's Instagram

• obé Fitness — The digital fitness platform Ashley co-founded*

Ashley Mills is a founder, strategist, and lifelong learner with a deep passion for literacy, wellness, and storytelling. She began her career in the entertainment industry as a talent agent at Creative Artists Agency (CAA), where she represented some of the world’s leading voices in media and culture. Drawing on that experience, she went on to co-found obé Fitness, a groundbreaking digital health and wellness platform on a mission to empower women to discover the joys of daily movement. As Co-CEO, Ashley scaled obé into a category-defining brand, forging strategic partnerships with companies like Disney, American Express, and Samsung. Today, Ashley is focused on the literacy crisis in America, particularly how neurodivergent children and adults are underserved by traditional systems. Drawing from her own lived experience with ADHD and dyslexia, she’s building tools and narratives that demystify how we learn to read—bridging cognitive science, creativity, and technology to ensure literacy is accessible, achievable, and empowering for all.

Ashley is a recipient of numerous awards, including being named one of the “100 Most Intriguing Entrepreneurs” by Goldman Sachs, recognized as a Changemaker at Glamour’s Women of the Year Awards, and leading a company that was honored as one of the Most Innovative Wellness Companies of 2022 by Fast Company.

*post contains affiliate links