The Power of Growing Together: Friendship, Career, and Building Brands with Jessica Graboff of CAA
Tue Dec 23 2025
No one pushes you, challenges you, or calls you on your b******t 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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No one pushes you, challenges you, or calls you on your b******t 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 Subscribe to The Farrynheight Podcast: YouTube Spotify Apple Podcasts Follow Farrynheight on social: Farrynheight Podcast Instagram Farryn Weiner Instagram Farrynheight Instagram Farrynheight LinkedIn Interested in raising brands? Send us a note at hey@farrynheight.com or visit us at https://farrynheight.com/