The Farrynheight Podcast23 Des 2025

The Power of Growing Together: Friendship, Career, and Building Brands with Jessica Graboff of CAA

No one pushes you, challenges you, or calls you on your bullshit quite like your best friend.

Farryn’s ultimate boss and best friend of nearly 20 years, Jessica Graboff—an agent at CAA—joins the Farrynheight Podcast for an intimate conversation about friendship, career, and the lessons that shaped them both.

From early days as ambitious twenty-somethings in New York to building brands and storytelling on opposite coasts, Jessica and Farryn unpack what it really means to evolve side-by-side both personally and professionally. This is an intimate, full-circle conversation about loyalty, reinvention, and the beauty of building your life—and your career—with people who see your potential before you do.

Timestamps:

00:00 – Introducing Jessica Graboff: Agent, Mentor, Best Friend

03:29 – Would We Live Together Again? Absolutely

05:49 – Moving to NYC & Becoming Real Friends

06:55 – Early Ambition & Career Drive

08:18 – Discovering We’re Both Storytellers

09:58 – Law, Talent, and the Birth of Brand Storytelling

12:06 – The Rise of Talent-Driven Brands

14:07 – Learning From Each Other’s Worlds

15:59 – Shanghai, Michael Kors & Early Career Lessons

18:21 – Learning Through Failure as a Young Agent

20:31 – Why Moving to LA Changed Everything

21:23 – What Makes a Successful Agent

22:16 – Building Trust With Talent & Brands

24:05 – Defining Your Personal Brand & Lane

25:41 – Working With Powerful Women in Hollywood

27:50 – Motherhood, Ambition & Identity Shifts

29:06 – Returning to Work After Kids & COVID

30:00 – Sacrifice, Guilt & Balance as a Working Mom

31:26 – Growing Careers Side by Side

32:59 – Diverging Paths: Marriage, Divorce & Growth

34:36 – How Motherhood Changes Perspective

40:22 – What’s Next in Brand & Celebrity Marketing

45:15 – Creativity, Growth & Staying Curious

46:09 – Rapid Fire

46:22 – Fear of Scaling & Letting Go of Control

50:47 – Final Thoughts & Outro

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Interested in raising brands? Send us a note at hey@farrynheight.com or visit us at https://farrynheight.com/

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