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Daring to Leap: Dinah Chapman on Reinvention, Entrepreneurship, and Motherhood

My Most Authentic Life
My Most Authentic Life
Episode • Mar 19 • 28m

Join host Fede Vargas for an inspiring conversation with Dinah Chapman, a bold entrepreneur and mother who walked away from the corporate grind to build a thriving business and a life on her own terms. From selling everything to travel the world, to launching Little Trouble, Dinah shares her journey of taking big leaps, trusting her instincts, and redefining what success and balance truly mean.

Listeners will gain insights on embracing uncertainty, building a purpose-driven brand, and navigating the challenges of entrepreneurship while raising a family. If you've ever felt stuck between stability and chasing your dreams, this episode will remind you that once-in-a-lifetime opportunities happen more than once—if you're willing to take the leap.

What You’ll Learn

  • How to embrace reinvention and make bold life decisions
  • The reality of running a business remotely while raising kids
  • The emotional impact of branding and storytelling in entrepreneurship
  • How motherhood fuels creativity and leadership
  • The mindset shift required to take life-changing leaps

Episode Highlights

[00:00] Fede’s thoughts on redefining once-in-a-lifetime opportunities
[01:13] Dinah’s bold move: Selling everything and traveling the world
[03:31] How New Zealand changed her view on success
[05:22] The work trip that made her realize everything had to change
[07:06] What motherhood teaches about resilience and entrepreneurship
[12:57] The inspiration behind Little Trouble and its mission
[15:27] Running a business remotely: Challenges and advantages
[18:28] The deeper impact of a brand: Customer stories that matter
[21:41] Creativity vs. data: What makes a brand truly last
[23:25] Dinah’s biggest lessons on confidence, reinvention, and trust
[25:21] How once-in-a-lifetime moments happen more than once
[26:30] Dinah’s definition of authenticity

About the Guest

Dinah Chapman is the founder of Little Trouble, a seven-figure direct-to-consumer kids clothing brand built on creativity, joy, and purpose. After experiencing corporate burnout, Dinah took a leap, traveling the world with her family and ultimately building a brand that inspires smiles. She’s passionate about entrepreneurship, motherhood, and helping others find the confidence to reinvent their paths.

Connect with Dinah Chapman & Little Trouble

Website: www.littletrouble.com
Instagram: @littletrouble | @dinahm_chapman

My Most Authentic Life Distributed by: Genuina Media

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