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November 5, 2025 76 mins

Debbie gets real with Kim Miles, the powerhouse behind Miles in Heels Productions, a woman who’s turned charisma into a career and authenticity into an art. Together, they unpack the unfiltered reality of entrepreneurial women who play by their own rules. A TEDx speaker and former media pro, Kim shares her journey from sales hustler to event-production maven, revealing how strategy, humor, and authenticity drive her success. From career pivots to the power of connection, this episode is a masterclass in owning your vibe, breaking molds, and building your empire your way.

 

Topics

00:26 Introducing Kim Miles: Founder of Miles in Heels

01:49 A Toast to Paper Planes and Bartending Stories

03:23 The Art of Sending Back Drinks

09:34 Kim's Journey: From Syracuse to Financial Advisor

12:47 Embracing the Zigzag Path of Entrepreneurship

14:09 The Birth of Miles and Heels Productions

14:45 Launching MAHJ House: A New Venture

32:26 The Importance of Knowing Your Worth

36:49 The Value of Knowing Your Worth

37:23 Behind the Scenes: The Hidden Efforts

38:06 The Importance of Asking for What You Deserve

39:40 Overthinking and Its Impact

42:00 The Power of Human Connection

47:00 Authenticity in Branding

56:15 Networking and Building Relationships

01:08:29 Embracing Different Life Paths

01:13:23 Conclusion and Final Thoughts

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