Episode Details

What happens when the very things that make you different become your greatest strengths?

For Fitzann “Fitz” Reid, showing up fully, taking calculated risks, and creating opportunities where none existed before have been defining themes throughout her career.

A lawyer, investor, entrepreneur, sports owner, and leader, Fitz has built a career that defies traditional expectations. From growing up in South Jamaica, Queens, as the daughter of Jamaican immigrants to serving at the highest levels of the SEC, helping launch Hunterbrook, and investing in professional sports, she has consistently chosen growth over comfort and possibility over convention.

In this episode of Branding Room Only, Fitz and Paula explore what it means to build a career intentionally rather than simply following the path laid out for you. They discuss the power of sponsorship, the leadership lessons learned through sports, the responsibility that comes with visibility, and the confidence required to remain authentic in spaces that were not always designed with you in mind. Fitz also shares her experiences as a Black queer woman and a first-generation Jamaican-American, and how those experiences have informed her perspective while never limiting the scope of who she is or what she can accomplish.

The conversation covers career pivots, entrepreneurship, investing, leadership, and personal branding through the lens of someone who has repeatedly stepped into unfamiliar spaces and found ways to succeed. Fitz's story is a reminder that growth often requires courage, that visibility creates possibility for others, and that some of the most meaningful opportunities appear long before there is certainty about the outcome. Her approach to life and work demonstrates the value of trusting yourself, staying open to possibility, and being willing to take the first step before you have every answer.

1:26 – Fitzann’s personal brand definition and why she describes herself as authentic, relentless, and empathetic

4:20 – Why a Bryan Stevenson (director of Equal Justice Initiative) quote that hangs on Fitz’s wall made such an impression

7:43 – How Fitz learned independence and resilience as a kid growing up in South Jamaica, Queens 

10:25 – How being a first-generation Jamaican American has influenced Fitz’s leadership and ambition

13:02 – The weight of responsibility often facing children of immigrants and how Paula conveyed that to her kids

14:25 – How Fitz has navigated her career and assumed leadership positions as a Black, queer woman in industries often lacking diversity

19:05 – How her background in sports has played a major role in Fitz’s leadership style

22:38 – How Fitz stood her ground against conforming in law school and grew her confidence over time

31:45 – Fitz outlines her career trajectory, from an early interest in politics and law school to buying an Italian basketball team and building Hunterbrook

39:02 – How that initial sports investment opened up bigger doors of opportunity

41:00 – How Fitz has been intentional about building her brand while navigating her career

44:32 – The root of Fitz’s personal and strategic interest in women’s sports, and investment opportunities still available

48:10 – Why advocacy through the National LGBTQ+ Bar Association is so important to Fitz

51:48 – Why Fitz will never compromise on how she shows up, and the magic she offers to others

53:41 – The importance of treating your difference from others as a superpower, not a disadvantage

Connect With Fitzann Reid

Fitzann “Fitz” Reid is a partner, general counsel, and chief compliance officer at Hunterbook, a startup media company and hedge fund. She’s also an avid sports investor and co-founder of Vera West Sports and Entertainment. 

Before Hunterbrook, she spent the bulk of her career in the U.S. Securities and Exchange Commission at th