Authenticity, Ambition, and Betting on Yourself with Fitzann Reid
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Description
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.
Chapters
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 the highest levels, serving across Examinations and Enforcement as well as Senior Counsel to Commissioner Allison Lee. Then she moved on to become the Chief Compliance Officer and Deputy General Counsel at impact-focused hedge fund Engine No 1. Her work spanned rulemaking, enforcement, litigation, whistleblowers, and on-site examinations of registrants, including broker-dealers, investment advisers, private fund advisers, and mutual funds.
Fitzann has a BBA from Pace University, an MBA from Wharton at UPenn, and a JD from Washington University School of Law in St. Louis, where she later taught federal regulations and enforcement as an Adjunct Professor. Off the clock, she serves on several boards, including the National LGBTQ Plus Bar Association, and is registered with the state bar in D.C. and New York.
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Sponsor for this episode
This episode is brought to you by PGE Consulting Group LLC.
PGE Consulting Group LLC empowers individuals and organizations to lead with purpose, presence, and impact. Specializing in leadership development and personal branding, we offer keynotes, custom programming, consulting, and strategic advising—all designed to elevate influence and performance at every level.
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Transcript
Paula Edgar: Welcome to Branding Room Only, the podcast where your personal brand gets a front row seat. I'm Paula Edgar and if you're here, it's because you know your brand isn't just about what you do, it's about how people experience you. In each episode, you'll hear stories, strategies and lessons from leaders and influencers, who built their brands and made their mark. And I'll share the tools you need to do the same.
Let's go. Hi, everybody, it's your host, Paula T. Edgar. We're back in Branding Room and today, I have a fantastic guest, I can't wait for you to meet. Let me tell you about her. Fitz Reid, she is a Partner, General Counsel, and Chief Compliance Officer at Hunterbrook, a startup media company and hedge fund, an avid sports investment and co-founder of VeraWest Sports and Entertainment. Prior to Hunterbrook, she spent the bulk of her career at the U.S. Securities and Exchange Commission at the highest levels and was the Deputy General Counsel at Activist Investment Firm, just kidding, into number one. Off the clock, she serves on several boards, including the National LGBTQ Plus Bar Association and is a proud dog mom to Huey. Fitz, welcome to the Branding Room.
Fitzann Reid: Thank you for, I know it was… thank you for having me and I know that was a mouthful, so, you know, I appreciate you.
Paula Edgar: It’s all good, all good. All right, so let's jump on in. I ask everybody this, what does personal brand mean to you? How would you define it?
Fitzann Reid: Yeah, I mean, look, for me, personal brand is the impression people have of you, even if you're not in the room. You know, it's the expectations, the beliefs, the values that people ascribe to you, even if they've never met you. Right. I can't tell you how many times I've gone to an event, spoke on a panel. Somebody will come up to me and say, hey, I've heard of you. So there's a conversation about me happening, even when I'm not in a room and maybe with people I'll never meet. And you always want that conversation to be obviously positive, but actually reflect who you are as a person, like you truly are. And that to me is what it means to kind of be authentic, when it comes to your brand as well. But, you know, I think the question is not necessarily how I want to be perceived, but you want to be consistent enough and visible enough that people form the right perceptions about you.
Paula Edgar: I love the right perception as a sort of carve out, because it can be they are talking about you in the rooms and it's not what you want it to be.
Fitzann Reid: It could go the wrong way, right.
Paula Edgar: Yeah, exactly. So how would you describe yourself in three words, or short phrases?
Fitzann Reid: Oh, man, I think. First things first is authentic. I'm from New York, born and raised. I'm the child of Jamaican immigrants. I have big New York energy, big energy for first generation folks that have come to this country and contributed so much. And I think I walk into any room that I'm in right now and this has not always been the case, but… And I always present myself in the same ways, because I'm consistent in how I present and who I am. And there's no need for me to hide any part of myself. So I would say authentic first. Relentless, definitely. I refuse to accept the ceilings that other people have imagined for me. And what I mean by that is I can't tell you how many times, you know, I've said I wanted to do something, or I put that out into the world. I always express where I think I'm going or want to go. And, you know, people have said, oh, that's not possible. Oh, you can't do that or like that's never been done before. And I'm like, OK, I mean, I'll be the first to do it. I'll just do it. And so it's either going to be, you know, I get your help to get in the door, to do the thing, or I'll figure a way out around you. And that's been so true throughout my career. I have so many examples of that. But yes, definitely relentless. I don't give up. And the last thing I would say is empathetic. I try to meet people where they are without judgment. I know that we all come to a space with different backgrounds, different life experiences and there's so much that I can learn from other people and their experiences. And I think there's a lot that folks can learn from me. So I try to be, always walk into a space being empathetic to those around me.
Paula Edgar: We need so much, so much of that these days, all times, but definitely these days. So, love that. So what about, do you have a favorite quote or motto that resonates for you right now?
Fitzann Reid: I'll tell you a quick story. I do. I'll tell you a quick story around it, though. When I was in law school, I went to Washington University in St. Louis and from New York moved to St. Louis, didn't know anything about St. Louis. I couldn't point to St. Louis on a map for you, but I moved out there, because I got into Wash U and I got a scholarship. And I said, well, they're going to give me money, so I better go down there. And so I did. And there weren't many Black folks in our class, there were some, but not many. And this is the first time I've had any experience with the law. I don't come from a family of lawyers or anything like that. And so for folks who don't know, your first year of law school is a bit of a hazing exercise, right? They're trying to separate you out a bit. And it's really hard. Law school is not easy, no matter what school you go to. And I had a rough time. I was trying to understand the law and learn quickly. It's a very competitive environment. And I remember my first year, Bryan Stevenson, the executive director of the Equal Justice Initiative, came to the school and he gave a talk, he gave a lecture. And a lot of it was about his background growing up and how he ended up founding the Equal Justice Initiative and all of his work that he does for his clients. And again, he's a titan in the legal industry. And he was so inspiring. I mean, he too didn't come from a background of lawyers or anything like that. He talked about his struggles going through law school. So after that, I'm a very forward person. So I emailed him actually, after this session, I sent him an email. And I said, hey, my name's Fitz. I saw you speak, you're really inspirational, I just want to let you know I'm struggling, too. I have a similar background to you, and I'm doing my best. And I didn't expect a response from him. But the next day, I actually did. He wrote me a nice response. I actually have it framed, I printed it out and framed it. And I look at it pretty much every day as I walk into my office. He said, keep your eyes on the prize, don't give up, the world needs you. Your voice and your understanding that life has taught you is important. So I wish you the very, very best. And he signed it. And it was just so meaningful to me. And it really inspired me to keep going. So I shout out to him all the time. If he could do it, I could do it. And I've done it. So that is definitely my favorite quote.
Paula Edgar: I love the story and I love that. I mean, it resonates even from, you know, from him through you to everybody else. It's just a good reminder that we're here on purpose and we should maximize the opportunity to add value, where we can. So thank you for sharing that.
Fitzann Reid: Of course.
Paula Edgar: What about this? What's your soundtrack? We're going to get full Fitz, coming to the stage. What song is playing in your head? What's your hype song?
Fitzann Reid: Right now. So I'm a big Knicks fan, I am from New York. The Knicks are doing really well. My Knicks are doing really well. Right now it would have to be New York by Ja Rule. They play it all the time in Madison Square Garden as a hype song for the team. It's all over the New York Knicks socials. It is definitely one of my hype songs. Anything by Jay-Z at this point. Jay-Z's back out here performing. Definitely a big fan of New York rap, New York music and anything that takes me back to growing up in New York.
Paula Edgar: Love it. So tell me, where did you grow up in New York and how do you think that that shaped you?
Fitzann Reid: Southside Jamaica, Queens, all the way. We didn't have a lot of money growing up. I grew up in the hood. I grew up in Jamaica, Queens. Born in Jamaica Hospital, went to Jamaica High School. Parents from Jamaica, so Jamaica all around. And, you know, I went to a school, where less than half of the people who graduated, New York State Public School, where less than half of the people graduated, I went on to college. And so definitely, definitely in the minority there, in terms of, you know, moving on to college and getting a degree and that kind of thing. But I've always been internally motivated. And, you know, there was no world in which I wouldn't continue my academics and try to go to college and beyond. But, you know, I grew up as a latchkey kid. I don't know if you know what a latchkey kid is.
Paula Edgar: I do, I was…
Fitzann Reid: All right, so you know what a latchkey kid is.
Paula Edgar: I do.
Fitzann Reid: So, a latchkey kid, just for anybody listening, there was a time and I don't know if it's unique to New York or if this was everywhere, but if your parents had multiple jobs, or couldn't pick you up from school or anything like that, it wasn't uncommon that from a young age, kids would have a key around their neck, or in their pocket, or something like that, to get home. And so I had to, at a very young age, probably six, seven, eight, I started like walking myself to school and get on the bus and get on a train and navigating the streets of New York on my own, because my parents were working and they had multiple jobs. And my responsibility was and this is before the days of the cell phone. So, you know, you kind of, my responsibility was to get myself home and call my mother and let her know I was home, take the chicken out the fridge and you know, all the things that you need to do, so that when they get home, we can have some dinner. But you know, I was, that means I was very self, sustaining in some ways, you know, even from a young age, I knew how to navigate, if the bus didn't come what I was supposed to do. Right. And so I'm very street smart to this day. I know how to get around on my own, even in new places. And so that's kind of how I grew up. And I think it's shaped me, because you can put me in any new situation and I'll figure it out. Like, that's how my brain works. Right. I'll figure it out, because I've had to face that even from a very, very young age.
Paula Edgar: Yeah, that New York latchkey kid resilience. I was taking the subway at eight. I would have to meet my mother at the World Trade Center in the…
Fitzann Reid: That's right.
Paula Edgar: I would wait in the corner of the [inaudible 00:10:13] in the World Trade Center or in Learners. They knew me. They were like, she's down here. But yeah, you got to figure it out.
Fitzann Reid: You got to figure it out.
Paula Edgar: Mighty, mighty Gen X and some millennials in there, too. We got to get it done. So tell me, I also am half Jamaican, half Bajan, the West Indian experience. What do you think about being a first-generation Jamaican-American? How does that Jamaican piece impact and influence your leadership, your ambition? Responsibilities.
Fitzann Reid: Yeah. I mean, I think if you talk to… it's again, not uniquely Jamaican, I think it's a lot of immigrant communities that we all want something better for the next generation. And so, for example, for my family, my grandmother came to New York from Jamaica when she was in her 20s. She's now in her 80s. So she spent more time in the U.S. than she spent in Jamaica at this point, but she left everything she knew to come to the U.S. and ultimately got my mother and all of my other relatives into the U.S. from there. And they've all gone on to do amazing things in their own rights. But when you talk to her, first of all, she still sounds like she is from Jamaica. She has the thickest Jamaican accent, even though she's been here for like 60 years. But, you know, you talk to her and you talk and you talk to her about, you know, how scared she talks about how scared she was to come to the US. But she did it because she wanted a better life, not only for herself, but for her children and her children's children. She's very open about that. And it's funny, because every accomplishment that I've had, every accomplishment that any of my cousins or anything have, whether it's graduating high school, college, whatever it is, she always says, you know, you're the reason why I came to this country. She's very, you know, adamant and open about that. And, you know, it's a reminder of the responsibility that I have to see that through. She did a very brave thing and a hard thing, coming to a place, where you don't know anybody and building a life. And so I do feel an immense sense of responsibility to do well, to, you know, every time something big happens in my life, big or small, I call grandma, let her know, you know, because, you know, this is the stuff that she imagined and didn't know could be real for us. And now that is. So I do feel that's where my ambition comes from, I think, is just making sure that I'm making her proud.
Paula Edgar: I love that. That resonates for me deeply as well. You know, my parents, you know, would say, remember that the prayers that your grandmother prayed for you are what, you know, you're living right now. And it's so, I feel that all the time. And I think about when my kids leave the house, I go, what do you remember? And they're like, remember, you're an Edgar, don't do anything stupid. I'm like, exactly. All right, now go on out there. Do not embarrass me. Go, go forth and prosper.
Fitzann Reid: Well, I have a question for you then. Do you think that sometimes the weight of that responsibility can be a lot, right? And, you know, we're always pushing, immigrant parents in particular, always pushing their kids to, you know, be engineers, lawyers, doctors and that kind of thing. It's an immense weight on the world. How do you, how did you handle it? Or how do you, you know, try to convey that to your children? I mean, they have a lot of responsibility as did you, to carry this forward.
Paula Edgar: It’s a great question. I think I felt the weight more. You know, my parents, they were, you know, working folks. They just got it done. And I have always been decidedly ambitious, always. And so I took the “people have done this before you, you have to do more”, I still take it very, very seriously. For my children, I didn't want them to have the weight, but I wanted them to have the freedom of being able to choose. So I want them to be excellent, but I don't care what they're excellent at. I want them to go off and do what they want, where I had to be excellent in something that was something established. Like, you're going to be a lawyer. I still own a license, even though I don't practice, I still keep my license because my family was like…
Fitzann Reid: All that hard work.
Paula Edgar: That's how I navigate it. I tell them the standard of excellence is never going to go away. It's always going to be respected, but be excellent in whatever you choose. Right.
Fitzann Reid: So, yeah, yeah, yeah, absolutely. Absolutely.
Paula Edgar: So let's talk something about your career. You know, you have done a lot and you built a career in industries that have historically lacked diversity.
Fitzann Reid: A little bit, just a little bit.
Paula Edgar: What has it meant for you to navigate those spaces as both a Black woman and somebody who's LGBTQ plus as a leader? How does that impact you?
Fitzann Reid: Yes, I'm constantly in spaces, where I'm the only one, although I will say it's getting better. You know, I go to more finance events and law events and there are other Black and brown folks for sure, more women, LGBTQ plus folks as well in those spaces, in those rooms. The obligation for me is always to remember to bring others with me. I'm now in a position at the startup. So I'm a general counsel at a startup. I'm now in the position and have been for a while, where I have real decision-making power. Like I decide who comes into our company, right? And I decide, you know, who we employ and who we give, or one of the people who decides who we give promotions to and that kind of thing. So that, you know, that means that I can make decisions that include diverse thought and diverse folks, in terms of like building a company that I wish, an environment that I wish existed when I was coming up. Right. And so at Hunterbrook, we have like our full-time folks, very diverse group of folks and we all work together and really love and have a passion for the work that we do. But it was intentional, like we've been really intentional about how we're building this organization and who's coming into it. And so, you know, that's a difference, right? Like I'm in the decision making seat now. And so that means I have a responsibility to figure out how to, like, implement the things that I wish were implemented, when I was coming up, because for a long time, I was the only. So, for example, I'll give you two quick examples. One, when I was at the US Securities and Exchange Commission, so I worked there, I worked in the federal government for about seven years, prosecuting things like insider trading and Ponzi schemes, working at the highest level, working for one of the commissioners. When I got to the San Francisco office at the SEC, I worked in enforcement. I was the third ever Black person to work in that office. And that office has been around for at least the 80s. And the other Black woman that had worked there, she had been there for, I want to say, 18, 19 years as the only Black person there. And so that to me is a shame. There's no other way to state it. That means there was no intentionality in trying to get Black folks and other folks of color into the office, right? When I then went on to work at an activist hedge fund, we were trying to get companies to be more environmentally friendly. I had a boss, Nate, who you know, Nate was the first ever, first time in my career ever that I had a Black boss. And so, you know, again, like you see these structures and you see these things and I always envision like, how would I do it differently? Well, now I'm in the position to do it differently. And so, you know, that's the thing that I think about these days.
Paula Edgar: I love that you talked about the intentionality, in order to make these places more inclusive and more representative. And, you know, speaking of brand and Nate, I recall him telling me about you. And one of the best things I think about him is that he is decidedly, like, he's like, if you're my person, you are my person. And so my ears are wide open, when he's trying to tell me about someone, because he's like, now it has to be all of our persons, not just mine. And so branding wise, I already liked you before I knew you. So the power of having somebody else as a sponsor who understands and sees your potential and can talk about you when you're not in the room. This is an example of that, that I was a part of. So I'm glad.
Fitzann Reid: Yeah. I will say the same exact thing of you. I knew of you before I met you. Like very much so because of Nate. You know, he's a great example of someone, who very much promotes people, even if they're not there, right? And so even if you're not in a room, you need somebody in your life that will, multiple people in your life, whether it's professionally or otherwise, that will just promote you, talk really well about you and talk about your successes and big you up, even when you're not there, because it really is meaningful. And I do think that's the kind of energy that will not only come back to you, but to them, too, when we're talking positively about each other.
Paula Edgar: A hundred percent. Tell me, what do you think about your background in sports helping you shape who you are, how you approach leadership as well? I think there's a lot of people who I know who have really strong brands, who have a connection to sports in their past. And I want to see what your thoughts are about how that helped you to be where you are right now? Tell the folks about the background.
Fitzann Reid: Yeah, I grew up playing and watching sports my entire life. I played soccer growing up.
Paula Edgar: Yeah, Jamaican.
Fitzann Reid: I'm Jamaican, that’s right. I played soccer growing up. To this day, I'm such a big sports fan that I have ESPN on like 24-7, even when I'm working. My wife makes fun of me, because every day she walks in the house, she's like, there's another game on? I'm like, yeah, there's always a game. There's always a game. I'm always watching something. But, you know, there's a lot in sports that teaches you more than a classroom can teach you. And that, you know, for example, resilience, when things get hard, when you lose, it teaches you how to lose, lose with grace and figure out how to adjust and learn from that. Because… and there's so many times you're going to make a mistake in your career. Right. That's natural. No one's perfect. And so you're going to make a mistake in your career and you're going to have to figure out how to rebound from that. So figuring out like resilience, accountability, being accountable to people around you, being accountable to yourself, something bigger than yourself, right? And then leadership, I think, is the big one, right? For me, I was never the star player. I was a very good role player. And the thing that I focused on was how do I make everyone around me better? How do I pick up folks, when their heads are down? You know, like, how can I bring the energy and support people, whether we're having a good or bad day on the pitch. And so that's how I think about it in life and in work today, is like we have a community of folks, we have employees that have to operate at a very high level all the time, which is exhausting. And so how do I support folks? How do I give folks time and space to maybe need a week off, you know, because you've been working hard for three months, right? Like we need some time off to break and, you know, get away from work to come back refreshed. How do I make sure that my team is operating at the best that they can, at any given time, because the industry we work in is so high pressure. And so, you know, that's how I think about leadership. And, you know, I really learned that from just growing up and playing sports.
Paula Edgar: I mean, it's a really sort of good connection, because as I was listening to what you were saying, I also played soccer, when I was growing up and definitely was not leading anything. But I remember specifically having a game where we lost and I am not a very good loser. I don't like to lose. Losing is not a part of my trajectory. You know at the end of soccer games, they say make you go, good game, good game, good game, good game, like with the other team? I refused. And I remember the coach was like, Paula. And I was like, it wasn't a good game. I'm not saying good game. But what his response was is that, what are you teaching the other people on the team if you don't? And so it really stuck out for me that people were watching me. So it wasn't just my bad mood and inability to lose well, but it was also what I was showing folks, so that we could be a better team as we went forward. So I do think, you know, that teamwork is a really great way. And that inclusive leadership you were just talking about and thinking about where somebody is, much more leaders need to do that. Now, tell me about this, moments where you felt pressure to be less you less of your full identity. Have you had that? And how did you navigate it if you have?
Fitzann Reid: That's a good question. So I'd go back to law. One of the best examples I can think of is in law school. My first year of law school and I don't know if law schools still do this, but I know it was a common practice. We took an etiquette kind of class, where they talk to you about how to interview at law firms and what do you wear? It's very gendered, right? Women must wear heels and skirts that look like this and men must present this way. And in my class, there were a number of folks, including myself, who have locks. I have locks and it's very part of who I am. I've always had locks. And there were young Black men in my class, who also came in with locks. And the message was effectively, you won't get a job with locks. You have to cut your hair. I was like, first of all, that's not happening. We're going to start there. I guess I'm never going to have a job. I don't know. Like, I don't know. So I drew this line in the sand. There were some people who did cut their hair. I mean, there was there's a number of Black folks in my class who did change their appearance, because they thought it would be better for them in the job market. And I get it. I get it. I get why you would do that. There were just some things about myself I was never going to conform to. And I knew, for me, it was like, I will find the space that's for me. And if the law firm won't take me, despite my great grades, in spite of all the things I've done in life, if you won't take me, because of the way I look, then it's not meant for me to be there, right? I strongly believe that there's a place and a space for everybody. And it's a matter of finding that place and space for you. And those people, you've got to find your community. And it's not easy to do in any stretch of the imagination, but they're there. I was like, I'll find my people. If it's not this law firm, I'll go to the next one and figure it out. And so there was a lot of pressure in law school to conform, because everybody does the same exact thing. You go to the law firm, you summer here, you go to be associated with this law firm, you become a partner and that's the track. And that's kind of what they feed you. But you don't have to do that. That was not my reality at all. And I've met many successful lawyers who didn't do that and they're very successful today. And so there's an immense sense of having to conform. And the ability to stand out and fight against that is, again, not easy. And I know not everybody can do it. We all got student loans to pay. You got to do what you got to do. I get it. But for me, I had to draw the line in the sand on my appearance.
Paula Edgar: Yeah. You know, I am just thinking about conversations that I've had a lot recently talking about folks who are first generation and then sort of knowing some of the rules of the road and what is supposed to be the trajectory for you to be successful in any space. And there's a pushback on that, no, I'm not doing that and knowing who you are. And then there's the knowing that people are going to push back against you if you don't conform to like that kind of power and being okay with it. And it takes confidence. And so I'm sitting here talking to you and I'm imagining people listening, being like, well, she's just confident. She just already knows who she was. She already said she was going to make her own table, build her own house, do these things. What do you think about, you know, you said that you understood when people had to make these decisions and I get it as well. But where do you grab that confidence, that ability to know that you can rely on yourself, regardless of the place that you're in. Like am [inaudible 00:26:19] I'm like, wow, that's great. But I'm wondering for the people who are listening, is there something that you tap into?
Fitzann Reid: Yes, I will. I'll answer that. But I also say that I haven't always been confident. I mean, confident is evolved over time. And my level of confidence has evolved over time. I'm at peak confidence now, because like, you can't tell me nothing now, I've accomplished so much, like, nothing you can tell me. But that hasn't always been the case, right? And people, it evolves, it changes. You're early in your career. You see everybody doing one thing. You're like, well, I guess I should do that same thing too. For me, early in my career, it was, you know, I speak in a way sometimes that I don't always use the biggest words and, you know, it's not very complex. I, you know, didn't grow… I sometimes say words wrong or I do, you know, I look at something wrong and, you know, I have all these degrees. And, you know, I am still not perfect and everything, right? And I definitely had some code switching when I was very, you know, coming up, because I was like, well, I have to speak in this exact way for people to think of that I'm credible and all these other things. Even though I have, you know, a law degree, I went to Wharton, I got a JD, I mean, an MBA. And, you know, I've done all these, you know, all these other awards. I was like, well, I have to present in this specific way when I speak. And like, if I mess up, then, you know, people are going to think that I don't know what I'm talking about and this and the third. And it was a lot of pressure. And over time, like, who cares? Like, I know what I'm talking about, right? And I don't need to speak in a certain way for people to think that I'm credible. And so, you know, it evolved over time that I felt the less pressure to code switch in different spaces. I could just be me, you know and just say, you know, speak how I speak. And one of the things actually I got a compliment on is I try to explain things in a way that, no matter what level of education or, you know, what you have, your level of understanding of a topic, anyone can understand it, you know? And I think sometimes lawyers get into this space, where we're talking above people. Yeah. It's like, no one talks like that. Like, what are you doing, say it in plain English.
Paula Edgar: Right.
Fitzann Reid: So it actually works to my benefit. People understand what I'm saying when I say it, even if they're not a lawyer. But yes, I have not always been this confident. It has evolved over time. And I think where it comes from is I was a gay kid growing up in New York at a time where, I guess, 80s, 90s, where, you know, times are more accepting now, I will say that. But I always knew I was gay. Since I was a child, I knew I was gay. And I wasn't necessarily bullied for it, but I knew it was different. And I couldn't put words to it at the time, but I knew it was different. And whenever somebody pointed out that difference, I had to build up this level of confidence in myself to, like, in some ways, not let it affect me. And, you know, over time, again, over time, as I grew up, I found spaces that were affirming for me. I didn't let negativity kind of impact who I was, or trying to change who I was. And I had to learn that on my own and I think it's just translated into different spaces. But, you know, being a gay kid, you know, in a place where everybody's straight or thought of straight at the time and during a time where things were less accepting, you kind of build up that kind of ability to block out the negativity in a lot of ways.
Paula Edgar: I'm glad we went down that sort of side road, because I do think that folks need to hear that confidence is not an on and off switch. And it really is… It's kind of like a, you know, like a long haul, in terms of getting there and feeling that, you know, I walk into rooms and I own them, because I do. But I didn't always do that. And there's a lot of fake it till you become it. And when you add the different layers of, you know, your identity, I do think that it brings a lot more, as you were talking, I was thinking, like, you kind of have to build a callous to, you know, what other people are going to do and just know that you've got what the thing is. And so I'm really glad that we kind of went down there.
Fitzann Reid: It's funny. Sorry, I was just going to say, it's funny that I think people always think of nothing's linear, things, you know, change and evolve and you have your ups and downs. But when you think about success, to me, it sometimes means that you're doing the thing that nobody else is willing to do. And it requires you to instinctually be different. And you're going to hear, people are going to have negative comments about that, right? When you're starting a business and nobody quite understands it, or, you know, think it's a tough area to get into, you have to have the confidence to be like, no, actually, I think this is a great idea. I'm going to continue to do this and I might refine it over time, but, you know and it'll get you places further than those people who had negative thoughts or ideas, comments to you. And so you gotta have that, a little sense of that resilience, a little sense of that confidence to know that, no, this is the right path for me.
Paula Edgar: Yeah. And to know that if it's not, that you can have confidence in yourself that you can recover for something else.
Fitzann Reid: Yes, yes, yes.
Paula Edgar: Yeah, I think that that's a really important piece, because every… I've tried a whole bunch of things that didn't work.
Fitzann Reid: That's the thing that we all have. We all have.
Paula Edgar: Well, let's go backwards a little bit. So talk about sort of the trajectory going from where you've gone. What are some of the pivotal moments in your career? You talked about the SEC, you talked about working at Engine One, but you've done so much more. Give the folks a little bit of a mountain view of your career.
Fitzann Reid: I'll start from the top. So when I was coming up, I didn't know exactly what I wanted to do. I knew what I was good at. I was good at math and numbers. That was pretty solid for me, all the time, even in high school and all of that. So I went to college. I studied business and finance, because I figured those classes would be the easiest for me. And my last semester of undergrad, I had the opportunity to intern for Hillary Clinton when she was senator of New York. And so I worked on her constituent affairs staff and actually stayed a little bit after graduation. This was the first time she… just before the first time she ran for office for president. And I thought, well, maybe I'll go into politics. Right. And I looked around and everyone on the staff was a lawyer, even though they weren't practicing law. A lot of lawyers in the room. So I thought to myself, well, I guess going to law school would be the best thing to do, because it seems like everybody… that's what everybody else does. If I take the LSAT and I get a good grade on it, that might be a good sign that I need to go to law school. I took the LSAT and got pretty much near perfect grade on every section. I was like, that's a great sign.
Paula Edgar: Go ahead and flex on us.
Fitzann Reid: Great sign. I guess this is what I'm going to do. So I went to law school, like I said. And again, I saw everybody going in one direction of going into law firms. I interviewed at all these law firms and I met so many lawyers that were just miserable. They did not enjoy the work they were doing. They were doing it, but they didn't enjoy it. And I was like, well, life is short, man. I don't want to do things where I'm not actually enjoying what I'm doing. Let me figure out another way. And so I ended up clerking for two federal judges and then immediately going in-house at Wells Fargo, where I worked for many years on the legal regulatory side of the company and compliance implementation and all these things that they had going on. I knew I did not want to be there for my entire career, but it would set me up well, because I'm working at a big company, working in compliance and working on things that, you know, regulatory issues. And I always wanted to work for the government, so I applied to the SEC and I got it. And they were like, well, you can come and work in the Philly office. And so that's kind of what started my career at the SEC. And then I became known very early on in my career as a very hard worker. I had all these cases that I was moving and I had great decisions coming my way and all that kind of thing. And so obviously it gave me more and more work. And I ended up moving very quickly up the ladder, moved to San Francisco to work in the San Francisco office and then ultimately worked for one of the commissioners on the policy side. And then after that, I said, well, been at the SEC, I've done all the things, done all the cases. So what's next? And I decided to leave and just try something new. That's, you know, I'm just the type of person that I'm always willing to just like, what's the new idea? How can I challenge myself? And so that's when I met Nate and I ended up working at our company. And we had a great time working there. About two years in, I met two founders, who said to me, we want to start a media company and a hedge fund and the hedge fund will help support the work of the media company, so that we can produce really good articles and reporting and trustworthy work and be able to actually finance it, without having to do ads or paywalls. People can see this information for free. And I said, well, this is interesting. And they said, well, we need help setting this up. And I decided to join them. And we built this company, Hunterbrook, that has been just taken off. And we've done something like 200, 250 pieces of in-depth reporting on companies of all types, sizes and places and what they're doing, good or bad. And we've done really well for ourselves. That's just been an exciting, exciting journey. Again, just taking a leap of faith. These guys came to me with an idea and I was like, sounds pretty cool. Let me try it. I have no idea if it's going to work, but let's try. And I was able to do that and all of that somewhere. I decided to get my MBA at Wharton. When I was at Wharton, I met some incredible, incredible entrepreneurs and other folks. I ended up buying an Italian basketball team with a couple of other students. So it was five of us as the majority owners. And we bought a team in Trieste, Italy. Again, big sports fan. I've never owned a team before. I don't even know what it means to own a team. We ended up buying, it started as a class project and it turned into a real thing. I actually came home one day and told my wife, I think we're actually buying this team. She thought I was insane. I don't speak Italian. I've never been to Trieste. Like there's just a lot of barriers here. And we bought the team. And the first year after we bought the team, the team ended up winning the championship. And we did really, really well in owning this team. We ended up exiting the opportunity. And since then, I've rolled that into that investment, into other investments. And I've bought into other teams as a minority owner and leagues and wearables and all types of things. And I've been deeply into women's sports in particular. I've got some projects cooking up there. But, you know, I think… And when you talk about pivotal points, each time I'm just the type of person that one is always willing to build something new. If you have a vision, I'm the type of person that's like, all right, let's, let's figure out how to make it reality. Like, I don't know how we're going to do it, but we'll do it. Right. Let's sit down and figure it out. And two, just willing to take the risk. Like if something doesn't work, it doesn't work. What's the worst that… it doesn't work, okay, great. Then you move on to something else, but I'm always willing to just take the risk. So when they said, hey, we want to buy this basketball team. I said, all right, let's do it. I mean, I'll download Duolingo and I'll do my best with Italian, but let's do it. And we had a lot of success, a lot of success. And it's an experience that, you know, if I was to say no to, I'd have missed out on a really, really incredible experience.
Paula Edgar: I love the callback to, yes, it's risky and I did it, right? There's a lot of things that are risky. There's a lot of things that you don't know what's going to happen. But if you're looking at the balance, the reward opportunity is also great, too. And I think that, for me, that's what resonates about your brand, because I'm like, I like sports, too, but I'm not… But, you know, it takes a certain kind of person to say, well, yeah, that's great. I'm going to try that. And then there's the people who wave at you from the couch and the people who are standing next to you who are doing it with you. And I just think, you know, whatever your thing is and all of the points you just talked about, you ask yourself a reflection like, These people aren't happy, can I do something different? You know, what is it that's next for me? That's strategy. And when I talk about branding, I always say, like, when you are strategic and thoughtful and self-aware, it is a better outcome than it is when you're just kind of flowing with whatever's happening, when you actually see it happen.
Fitzann Reid: Yes, yes. You know, and it's funny, buying the Sports team has opened up so many more opportunities. Once you've owned a team, big or small, you know, people reach out to you, like, we also want investors for this team and that team. There's no like Craigslist or whatever, no ad, no LinkedIn for buying into sports teams. But once you're kind of in the circle, people know you've done this thing, all types of opportunities start coming your way. And that's what happened to me. And so that's, you know, and I was strategic in the sense that I knew that would happen. So I didn't know what was going to happen with the team itself. I knew that it was a good opportunity for me to get that experience, because there would be more opportunities like that along the way, if I did this. And so I knew that from the very beginning and I wanted to learn what it would be like to operate and own a professional team. This is a top team in Italy. What does it actually mean to figure out the best players to bring onto the team and be strategic about, you know, who the GM is and who the coach is? And how do you deal with all these moving parts of an organization? Because that's what… it's a business, it's an organization. How do you deal with the sponsors and the players and the fans and all these things? If you could figure that out in a microcosm, then you can move to a bigger and bigger scale of it. And so, you know, my dream one day is maybe I'll own a Knicks, right? But you got to start somewhere.
Paula Edgar: I'm here for it. Just like the New Yorker. I want that to happen. Let us vision that. Let us do it.
Fitzann Reid: You got to vision it, right? But you gotta start somewhere. You can't start with owning the Knicks, you got to start somewhere else and you build over time. So that's always been the vision. So when I thought about owning this team, it was, okay, this is the first step in many that's going to lead to larger opportunities.
Paula Edgar: So let's talk a little bit more about how you've been intentional about, as you've gone to these spaces, about building your brand. Again, you're adding on commas, commas, commas, and then I did this and then I did this and then I did this. And you just talked a little bit about some of that intentionality and being open to risk, but is it you start with the vision and then you go get it, or as you're in it, you're like, okay, I'm going to build this skill and I'm going to have this role and all those things roll into the brand. Like, how do you stay visible in the, like you're an investor, you're an owner, you're all these things. What's your strategy in terms of that?
Fitzann Reid: When I started law school, I knew I wanted to work in the government. So my strategy has changed over time, depending on where I am, right? So when I was in law school, I knew I wanted to work in the government. That was the goal, right? And then so the strategy was like, how do I do that? How do I best position myself to get into the SEC? And I knew working in-house at a large financial institution would do that. It was very strategic for me to go to Wells Fargo. That was fully intentional and it worked out. And then when I was at the SEC, I knew I wanted to leave and I knew I wanted to do something in the private sector. I didn't know what. And it was just fortuitous that I met Nate. And he said, we have this opportunity. Right. And we're doing this thing. I'm very mission driven. So I love the mission of what they were doing. And so I said, yeah, I'll absolutely jump and make the leap of faith and do that. So it wasn't as intentional. I knew I wanted to leave, but I didn't know where. I knew I had to be mission driven and I had this opportunity and I was ready to make the jump. So maybe a little bit of luck happened there or something happened where me and Nate met and this all came together. And then when it came to my current business at Hunterbrook, very mission driven, but it was also about building something new. And that was intriguing to me, because I had other opportunities. I could have gone to a lot of other places and done a lot of other things. I could have stayed at my former company and all these things. But there was something attractive to me, about building something new and doing something different, that I was like, we can actually make this thing work. And it will be a public good in some ways, at a time where people don't trust the news. They're not sure what to read, you know and that kind of thing. We can actually have an impact in a space that is struggling right now. And so, again, at that point, it wasn't necessarily intentional, but something fell in my lap and I was ready to act, at the time. I had the background that allowed me to come in and from the jump, help set up this company, get it running. And then with sports, it was very intentional. I think it's been intentional for me. I've always wanted to be a sports investor and build a portfolio. And I have started to do that. I'm starting to do that in many different ways. Buying the Italian basketball team, being the majority investor in that space, being an owner operator. It was very intentional, because I knew that good or bad, that experience would take me to the next place I wanted to be, which is like continuing to invest in other spaces. And, you know, I'm well set up now to, right now I'm working on, buying into a women's soccer team. Like I wouldn't have that opportunity if I didn't start with this basketball team. So it was always very intentional from an investment standpoint that let me do this first thing. And then I know it's going to lead to these other opportunities and ultimately greater opportunities for me to invest in the future.
Paula Edgar: Well, let's talk about that. So, you know, now women's sports are popping off now. Not everybody…
Fitzann Reid: Everybody wants to invest, everybody.
Paula Edgar: So, you know, I think that while there's lots of momentum, there's still we have work to do. I mean, given the world that we're living in.
Fitzann Reid: Yes, yes.
Paula Edgar: You know, tell me why specifically women's sports, you know, through VROS is important to you. Like what? Why is that the lane?
Fitzann Reid: I grew up playing soccer, playing sports and I didn't, you know, you had some idols to look up to, like Mia Hamm comes to mind. You had some, but you didn't have a lot. And even in basketball, you didn't have a lot. And I just look at where we are now and I'm just, first of all, I feel like I've been watching women's sports my entire life. Now I feel like everybody else is catching up. I'm like, I've been on this. I don't know where y'all been.
Paula Edgar: Welcome back.
Fitzann Reid: I guess we're here now. I'm glad you're here. But we've been on this. But it's just amazing to see. I go to these games and it's not just young girls just like you know, going crazy over these players, basketball, soccer, whatever. It's young boys too, right? It's, you know, kids generally just getting more into the sports, dads, parents, all these folks that are loving the game, loving the product and, you know, seeing women and being super athletic in amazing ways and showing up. And, you know, it's amazing to see where women's sports has come. I think that there's a ton of opportunity still. There's still a lot for these leagues and teams to do, but there's a ton of opportunity. For example, I remember coming up and the Liberty, they used to play like in, when I was in college, they used to play like in a jersey in some arena that wasn't really an arena. There was like no respect on the game at all. And I remember there was an investor I had met and he had said to me, you know, there was an opportunity to invest in Liberty. And at the time I'm in college, so I'm like, I can't, I don't have money for that. I deeply regret that. I deeply regret that. Man, I should have cobbled some coins together, because I would be so rich right now, right? So the WNBA is very hard to get into as an investor today, because of where the sport is. The Valkyries selling out entire seasons, they have more season ticket holders than the Warriors, which is insane. And so, you know, you look at stuff like that and you're like, wow, we've come so far. But there's still a lot of opportunity in the NWSL where valuations are increasing, but they're not exactly, I think, where there's much more room for it to increase over time. I wish I got into NWSL years ago, when the valuations were a little bit lower, but there's still, I think, an opportunity to come in. And media rights are increasing, viewership is increasing, the league is expanding. There's still a lot of opportunity there. Women's volleyball is taking off. A ton of opportunities. Hockey, same thing. And softball, college women's softball is drawing huge numbers on ESPN. Again, you see this attraction that folks are having more in the women's sports sector. And it's just amazing to see. There's a lot of opportunity to get into women's sports in a way that you can't get into men's sports in the US at this point.
Paula Edgar: You got me hyped up like I got to buy a team.
Fitzann Reid: You got to get in there.
Paula Edgar: I'm going to call you right after this, girl.
Fitzann Reid: I got you. I got you.
Paula Edgar: So going back, so, you know, the sports has a connection to you having played sports and how you came up and that being an interest. Talk to me about your leadership, you know, specifically talking about being on the LGBTQ Plus Bar Association board and thinking about advocacy work, particularly at a time when it is wild out in these streets and still choosing to take a leadership role despite all of the headwinds that exist. Tell me about that.
Fitzann Reid: It's hard, especially now. You don't want to be the target of anything. But I do think about the folks that have come before us, who put so much on the line, whether it's Black folks, LGBTQ plus folks, who literally put lives on the line to advance us to where we are today. And, you know, I think, well, I have no excuse. You know, like I have to carry that forward. And, you know, one of the things that's really hard for me and I'm still working through it is visibility. I am definitely going back to be actually a role player. Like I'm definitely the type of person that I could just work and not be the face of anything and just like go about my day. And you would never hear from me. And I'll just be fine. I'll be sitting on the couch watching sports and just doing the good work in the background and letting somebody else take all the kind of visibility and credit or whatever it may be. But I realize that while I could do that, it'd be to my benefit for sure. But it's a disservice to everybody else in some respects, because I still have people who come up to me, adults, in particular teenagers, who are like, who've never seen a Black lawyer. Like really, I've never seen at least a Black lawyer in finance, right? They think all Black lawyers may be public defenders or something, but not doing what I'm doing. And so I still walk into spaces and people are just like in awe of the fact that I'm a finance lawyer and I've done all these things, because they've never seen it before. And if they've never seen it before, then you can't imagine what you can't see. And so sometimes you can't imagine, especially as children, you can't imagine, you can't imagine yourself doing it if you've never even seen somebody do that. And so I feel the immense responsibility to be visible in certain ways so that, you know, folks know that it's possible to do what I'm doing. It's possible to do it better, you know, be more innovative than me or do something differently so that there is space for us in these places that historically has excluded us. And that I exist, there's so many lawyers like myself that exist and there's a community and a space for anybody of a minority background. And that even when it's hard and you're trying to do the thing, that you have folks like me that are willing to support you and to figure it out and elevate you. Visibility is something I struggle with. I try to put myself out there. Being on the board is part of that, because I do want people to know that what I'm doing is very possible.
Paula Edgar: And it's, you know, to your point about the importance of folks seeing, you know, when you started the conversation, you said when somebody says you can't do it, you're like, OK, watch me. I feel the same way very deeply, because when I came into the legal profession, it still is very white. But, you know, you see people with flashy nails, like showing up the way that they show up. And so I aspire for leadership roles, where I am very visible to show people that yes, lawyers look like this too. You can find value with some blonde braids. All of these things, there's not a boss that you put folks in. And that's important so people can see themselves in all these spaces. So I knew that the hour was going to go by super quickly, because it always does. I have two questions that I ask everyone on the podcast. And so one is this, stand by your brand. What is the authentic aspect of your personal brand that you will never compromise on?
Fitzann Reid: How I show up. I'll never, I can't say I'll never cut my hair, but my locks is like so integral. I've had it my entire life and it is a throwback to my Jamaican-ness. And like, it's just such a part of me that I can't see myself changing that part of me or, you know, how I dress or anything like that. That's true to who I am and something that I'm just not willing to change.
Paula Edgar: I love it. So the podcast is called BRANDING ROOM ONLY, because I'm clever. It is a play on standing room only. And so I ask everyone, what is the magic that you have that would have a room full of people with no seats left to experience about you?
Fitzann Reid: I think I would say I'm a bit of a magician in that I can really take whatever your vision is of what you want to do in life and help you make it a reality. I've done that time and time again with people. I'm doing that now at Hunterbrook. You know, no matter the idea, I talk to people and young entrepreneurs all the time who come to me with ideas. Hey, I'm trying to build this thing and they think it's hard or impossible to do. And I'm just the type of person that's like, if we can put people on the moon, there's nothing that we can't do. We can figure this out. We're going to figure this out together. And we'll do it in a way that will be innovative and smart and thoughtful and compliant and all these other things, but we're going to get it done. And so I'm very good at that. I've done it, like I said, time and time again. And so whatever idea that you have that you think is possible to do, I would challenge you to say, let's do it.
Paula Edgar: Finally, what is a piece of advice that you wish you had when you were younger that you want to give to folks to hear now?
Fitzann Reid: Ooh, that I wish I had. I would say I think of myself as being a Black queer woman as a superpower. And I think you should think about your difference in any aspect that you may be different from other people as your superpower. It's not something to hide. It's not something to be ashamed of. I walk into a room and I know it's my superpower, because it allows me to relate with people in different ways, right? If I walk into a room of, you know, all men, probably there's some Black men there and probably everybody likes sports. And I still can talk about that and relate to people. And so I'm not one dimensional. What makes you you is all these pieces, all the intersecting pieces of you that give you your superpower to walk in these spaces with your head held high. And I think we spend a lot of time thinking about our differences as a disadvantage. And I challenge that and I'd say, it's actually an advantage to have all these different intersecting identities.
Paula Edgar: What an inspirational way to end the conversation, because no matter who you are on the other side of this or watching us, I know that you needed to hear that, that there's space for you wherever you are. And I will see you all next time in the BRANDING ROOM. Fitz, thank you so much for being a part of the conversation.
Fitzann Reid: Thank you.
Paula Edgar: [inaudible 00:55:07] the next.
Fitzann Reid: I got you, I got you.
Paula Edgar: Bye, everybody. Talk to you soon, next time in the Branding Room.
That's it for this episode. I appreciate you hanging out with me on Branding Room Only only. Now, please do me a quick favor. Head over to RateThisPodcast.com/branding, so more people can join this conversation. And make sure to stop by PaulaEdgar.com/events to see what's next. Whether I'm live, online or in person, I'd love to see you there. See you next time in the branding room.
And until then, stand tall, shine bright, and always stand by your brand.
