Culture as a Revitalizing Force Transcript

More Elephant Intro

[00:00:38] Jason Rudman: Welcome to the latest More Elephant podcast. Today, I'm in conversation with Derek Fleming, senior advisor at HR&A Advisors and recently named by Crains New York as one of its 2023 notable Black leaders.

The excitement I have about this conversation is because we're going to go deep on culture and representation and lived experience, and, specifically, about edifying culture through real estate. Derek has a unique and deep focus on real estate and urban renewal, in complex, economically challenged communities. And his story, what he has worked on, the ideas that he has had, and the change that he has demonstrated, in a number of cities throughout America, is a story worth listening to. So, Derek, welcome to the More Elephant podcast. I'm thrilled you're here.

[00:01:38] Derek Fleming: Thank you, Jason. It's great to be here.

[00:01:40] Jason Rudman: Derek, I wanted to start with, as you and I were talking and preparing for this, you said something that really, really struck me, and that was that how you wake up today is so connected to your LA experience of the Eighties. And not that you look a day over forty; however, I’m talking about the 1980s! And so, I love that, right, because people are going to do the math, Derek, whereas 2023, I'm talking about the 80's.

But I love that because that's where I’d like to start because so much of what we do today, who we are, and how it shows up resonates with where we grew up and what that experience was like. So, would you fill out that narrative for us in terms of LA, the 80s, and how that was instrumental in who you are today and how you wake up today?

[00:02:32] Derek Fleming: Absolutely. I'll try to be detailed without being laborious about it. I think there are a lot of details to it that are interesting, but I guess the more poignant parts of it are really that I was born in Compton, California, in South Central LA. During that time, Compton was a place where many African Americans that came from the South came from the Midwest to the West Coast to find government opportunities and jobs on the West Coast.

And so, my grandparents were part of the whole migration on both sides of my family, my Dad's side and my Mom's side; both lived in Compton and were working class and hardworking. And, we had a really fantastic, I think, family foundation, but was, obviously, happening in Compton in the Eighties {where} there was a lot of what was happening across the rest of the country in Black communities. The influx of drugs, and crack in particular, and a lot of the activity that was going on around law enforcement, and it was a very tumultuous time to sort of grow up in South Central during all of that.

You know, a lot of my neighbors and kids that I played with had parents who were very protective of how to let us play and let us be free in our neighborhood and community. But it was also a great community. We were very communal and connected to each other. And so, it was really important to sort of understand the juxtaposition between what was happening around us — there were Crips, and there were Bloods and all that stuff going on in our midst — but there was also, like, really great fantastic families, kids, and things that we did together as a community, as a block, that were just like very wholesome experiences that everyone else has in every neighborhood.

So, I really experienced both sides of what people perceive as South Central LA growing up, and later moved to Long Beach, which, you know, was not too far away from Compton (but my grandparents stayed in Compton). They were still there. And so, I had cousins that were there, and so I always went back and forth and maintained that relationship with the community. And so, really, my family being very protective again of my experience and how I was being reared and where I was going, traveled, sent me to places. It's where I can see other things and have exposure and a broad view.

And so, by the time it was really ready for me to get to college and decide that was my next step, I went up north. I went to Berkeley and had the opportunity to get into a school that was close but away from home, and I think, a really formidable broad-based education that would set me up. I never forgot the experience, obviously, of where I came from and my foundation of community.

And again, by the time I got to Cal, Rodney King had happened and all of those things. Growing up in LA and going to Westwood, where everyone was break dancing, and it was about hip hop, and it was about a young Black kid being in and, in the city and out and about, there was a lot of tension between law enforcement and, what Black kids could really…what boundaries we could push, you know. And so, by the time I got to Cal [Berkeley] and really started to understand the political implications of what I was, where I grew up, the social implications of where I grew up, and where my family still was in South Central, even though I was at Berkeley, you know, number 1 public school in the country at the time, I was still very much connected to the realness of this place that people talked all sorts of ways about, you know, Compton.

So that framing, that juxtaposition, of having been places and now being at Berkeley and starting to have the opportunity to study economics, real estate, and study development, but then also having such a warm, positive perspective about where I grew up and about my community and the good things that came out of it, the good and the bad, but all the things that were instructive about life and about the importance of community. I just sort of kept that understanding with me as I started to study at Berkeley.

[00:07:13] Jason Rudman: Derek, as I listen to that story and think about my life and the blessing in my life, to have been exposed to your story, other stories, you know, people in my circle that don't look and didn't have the experience that I have. As we've shared, there are elements of my story that are very similar to yours, in terms of where I grew up, in a working-class family, and the essence of what I just heard you say is that you learned very early on, in an environment that could be perceived otherwise, that Black culture is valued. And it should be celebrated.

And the juxtaposition, you talked about this, right was you also grew up in a time where, if you looked at everything that was in the media, that is not necessarily what you saw. That Black culture, indeed, I would say, to some degree, the Black experience was not valued, was not elevated, was not talked about in positive terms. I think that colors a lot of what you have brought to everything that we're going talk about in terms of your investment in added buying culture through real estate.

[00:08:21] Derek Fleming: Absolutely. I mean, you know, growing up in South Central and, you know, having all of those very, very real experiences at the barbecues and the block parties, and, you know, again, like I said, we would trek from Long Beach and from LA, South Central, LA to Westwood and to be a part of where everyone was trying to experience the culture. And, again, the culture of hip-hop was really burgeoning at that point, and it was it. It was everything. And so, it shaped my understanding of the importance of the music, of the aesthetic of Black culture, and this was a pride for me to be able to have that as my background, you know.

[00:09:09] Jason Rudman: So how do we connect that throughline to your journey in real estate and urban renewal? Can you make that leap for the audience in terms of Black culture is valuable and I've got this rich, paradoxical experience, and I've gone to Berkeley. And some could argue that is a lifeline, right? That opens up apertures for you to be anything that you can choose to be. What's the connection to real estate and urban renewal?

[00:09:45] Derek Fleming: It was pretty organic, you know, the way it all unfolded. I, matriculating through school, through college, had different opportunities - finance or consulting or the traditional routes - and right after I graduated, I was actually offered an opportunity to go [on a] fellowship, to go to South Korea and study finance and real estate. I just applied for a fellowship and got the fellowship, so I was off to Seoul right after I graduated.

When I came back 6 months later from that experience of studying in Korea, the Chairperson of the selection committee that sent me over there said, hey, there's a real estate position at the San Francisco Redevelopment Agency, the Mayor's office. At the time, Mayor Willie Brown was the head of the San Francisco Mayor's office. He was the Mayor. And, you know, there's an opportunity for you to come and work in the real estate department in San Francisco.

And I really, you know, put 2-and-2 together in the sense that I wanted to do something that was meaningful. I wanted to go in a direction that felt connected to a personal experience for me, right? And, the idea that I could work for the Mayor's office, and at the time, the project that I was interviewing for was Bayview Hunters Point, which is a historic African American community in San Francisco, working on revitalization and neighborhood community development in the Bayview.

So, it felt connected to South Central to me, right? And this seems like where I should go. This seems like a really great opportunity. It wasn't that sort of strategic, it wasn't intentional. It really was an organic opportunity that presented itself but then felt right. It felt more tangible than just, you know, a consulting firm or, you know, some other Bank or something.

[00:12:03] Jason Rudman: Yeah. I'm smiling because, to me, you just described one of the many More Elephant moments in your life, right? If I just stand in the moment and I try to connect the person to what I want to do professionally, sometimes, you just have to stand and [be] still, and you attract what you're actually supposed to be doing at that point. A great idea that was formulated by the San Francisco Redevelopment Agency was just waiting for Derek Fleming to walk through the door in order to be the person to work on that work, to get a sense of personal fulfillment from it, but also the connection to the community piece that you talked about in your intro as to what you had learned and what had shaped you in Compton.

[00:12:46] Derek Fleming: And I wanted to be excited about my work. I just came out, I felt like I had opportunities, and I really worked hard to get into the school that I got into and to get into this position. And so, I felt like I could really push to do something that I was passionate about, that was exciting for me, not just anything.

And so, when this opportunity unfolded, I was like, that right there is something that I can be very excited about. Literally shaping and impacting a neighborhood that looked like where I grew up, right? And at all the connections and intersectionality of the culture that I was familiar with, that I was passionate about, right, that felt close to me.

So, yeah, it's being open, right, but it's also being clear about which direction you're going in and having the faith that you have what it takes once you pursue that to really be successful as long as you're being authentic In your choice making. Right? Being clear and authentic about why you're letting your passion drive you. Not running from your passion, but really allowing your passion to drive, and that's what I felt like I was doing.

[00:14:01] Jason Rudman: I talked recently in a blog post about this concept of workism in America, and I think what's critical there is, you're separating the passion of what I want to do from what it is that I do, defines me and consumes me, and doesn't allow me to actually have other opportunities within this thing that I call life. Right?

You squarely met what you knew you were passionate about with an opportunity to be a change-maker in San Francisco. And again, knowing enough about you, I think that you paid your dues, I hope that's the right word, dues but you had more public sector experience because that's the San Francisco Redevelopment Agency was then a springboard to the Empire State Development opportunity that you had in New York.

So, you continue this public sector commitment. It passionately is checking off a box, and then you have another More Elephant moment, which says, okay, I've done this. I'm really proud of what I've done. I'm not running away from it because I don't think there's more for me to do. However, there's another idea that I've got, there's another area of change that I want to effect on a grander scale.

So how did that come about? What is that pivot? What did that pivot solve for you in this arc of your story that we're talking about? And what did you ultimately end up doing?

[00:15:25] Derek Fleming: I mean, the through line, the connection, doing the development work in San Francisco, I went from the Bayview Hunters Point project, a historic African American community, to working on one of the largest revitalization projects in San Francisco at the time, which was the Mission Bay project, a 300-acre redevelopment.

That project started to get my hands, you know, dirty in design and architecture, and understanding different disciplines were involved in the development process. And so, by the time I had the opportunity to move to New York and work for a state-run development corporation, I was hired by the Empowerment Zone, which was a big federal and state initiative at the time that had $300 million to invest in Harlem and the South Bronx.

And so, okay, this is another opportunity for me to do this development thing in a community that looks like where I came from. And now I've got this background in economic development, tax increment financing, and architecture and design and open space and sustainability, affordable housing. So, all of these issues that I was that I learned in San Francisco I could apply in New York, in Harlem, which was like the capital of African American culture in our country. Right? And so that became very exciting for me.

And New York was exciting for me to stretch myself, to be away from home. And so, in that endeavor, I had the opportunity to do projects around the Apollo Theater, the Studio Museum of Harlem, and the Schomburg Center for Black Culture, but then also manage. Right? I managed a $60 million fund that, I now was learning how to invest and learning how to put public capital alongside private capital. And, again, it was just a very powerful experience for me to see, I'm actually making decisions in a part of a process that is uplifting a community that looks like where I came from that deserves it.

[00:17:33] Jason Rudman: Looks like me, and I love that, right? Perfectly. Yeah. It looks like me. And, I don't want to skip past the laundry list of places where you had an impact because those are, like, historical, cultural institutions that, without the work of the Empire State Development

[00:17:55] Derek Fleming: The empowerment zone, really.

[00:17:56] Jason Rudman: The empowerment zone within it, like, those would have fallen into disrepair. Those are phenomenal cultural institutions today. They have only gotten to be more significant, and I would argue, much better from access and a presentation perspective over the years, right? There's a level of gratefulness that I think the community owes to that work that sometimes doesn't get celebrated in the day-to-day because that work, at that time, was vital to making sure that those institutions still existed.

[00:18:30] Derek Fleming: Absolutely. And, you know, I was learning on the ground how important those institutions were. I’d heard of them, but really it wasn't until….I'm in my early- to mid-twenties at this time, and I'm really face-to-face with, like, oh my gosh, this is the Apollo. And I'm looking at a project that's going to do a revitalization, physical, you know, rehabilitation of this space. And it just was like, Wow. Right. It was very powerful for me.

And Lenox Lounge was another one of the projects that was in my portfolio which had been in, you know, in disrepair and was, again, like a Black iconic institution, right? Miles Davis, John Coltrane, Dizzy Gillespie, like the whole thing graced the halls of these spaces. And so, being able to work with my partners and team to revitalize these, you know, catalytic… they're not spaces, they're, you know, they're gosh, I guess I would just, you know, call them like cultural, they're culturally foundational, I don't know what you would call these spaces, man. They are just like cultural bedrock. And it's like this is the birthplace of the jazz era, of careers, of iconic moments that are historic in nature that all came out of these places. It was just an honor to be able to touch and to work on these spaces.

[00:20:08] Jason Rudman: I think what you're saying is these are historical, cultural, relevant stories that, if we don't preserve them, get lost, right… And I particularly get lost when we're talking about underrepresented and underappreciated communities because I think the other thing, Derek that you and I know particularly well is Harlem of the time you were talking about was the personification of a complex economically challenged community. Right?

If you look at Harlem today in 2023 and then you go back, you know, 25, 30 years ago, when you were doing the work on the Lenox Lounge and the Apollo and Schomburg, the reason you were called to do that through the development zone is because, as you mentioned, they had fallen into complete disrepair, and nobody was paying attention to.

[00:21:01] Derek Fleming: Yeah. Yeah. And along with that, you know, there was neglect, not just for these institutions, but the whole neighborhood holistically. You know, part of what the empowerment zone was about was the reinvestment, specifically, the intentional investment into these institutions and identifying them as important cultural institutions that were of African American nature. And so, it was unapologetically a Black initiative, Black/Latin initiative.

And it really was about allowing culture…this is where I learned. Right? This is where I learned the idea that if you let the Lenox Lounge, you know, if you let the Apollo Theater, you let the Studio Museum go, it's going to change the fabric, it is going to change the texture of what Harlem really is. And so cultural capital, which is something that I use as really my guiding light for my work today, really, my understanding of that, of cultural capital and the understanding of the power of culture, the importance of leaning into and allowing culture to be a business thesis, really came from these experiences. This was, like, my early, early in my career, these experiences of seeing how important these institutions were. And without them, you know, the value of the neighborhood actually diminishes, and so it was just an incredible learning process for me.

[00:22:37] Jason Rudman: I think the value of the neighborhood diminishes, Derek, and I think the value of American life diminishes. Right? So, we've talked about the importance and what those institutions and the work that you've done, the cultural capital, means to the lived experience of the community that's there and honoring the history. But we also have to acknowledge that that history is American history. And so often, we have not invested, and we have not celebrated, and we've not elevated the richness of that to the degree that I would argue is not only necessary but warranted.

[00:23:12] Derek Fleming: Absolutely. Yeah. Part of what makes these communities, these cities are communities, and cities so special and unique is the diversity, is the texture. Right? And so, when you talk about America and its global relevance and differentiation and importance, it is because of our contributions and our cultural attributes that we bring to the table, right, our distinct communities. And so, you're absolutely right. It's like, this is America that we're talking about, and so you're not rebuilding Black America, you're rebuilding America.

[00:23:52] Jason Rudman: I love it. And it shouldn't be lost on people that that's actually, you know, again, it's the rebuilding of America and celebrating the richness of tradition and culture through art, through music, the aesthetic. You talked about that, celebrating the aesthetic. So, at some point, you say, runway in the public sector is great. I've done all of this work, but there's a different calling. What fueled the pivot? And then describe what you did next.

[00:24:23] Derek Fleming: You know, I had gotten so much experience and done a lot of great work in Harlem and the South Bronx at this point. And I felt like I wanted to do something new and different and see what the private sector experience could be. And I wasn't sure what that looked like specifically or what direction that was.

And so, for me, it was about, you know what? It's time to go back to school and kind of take a beat. Look at what's going on in the industry, what's out there, what your opportunities are, Derek, and just really be evaluate. Use this time to grow, to be around some really cool, interesting people, but also rethink the, you know, what you know, where I'm going next here.

So I went off and went to get my MBA at Kellogg School of Management at Northwestern. And those 2 years, to, again, reaffirm the idea that real estate and all the power and creativity that comes with it was really…that was me. It was my passion. Right? And this is after being in business school and having the full array, you know this [as] you went to business school, the full array of opportunities and options.

And it's like, no. I don't wanna do that. Nope, I don't wanna do that. This, because there's a thing about the creative, the building process and the thinking through what could be and then actually applying that and then [being] able to go back and look at it and see what you've built. That process of the real estate continuum is what I realized was just so fascinating and interesting for me.

So business school was just an affirmation of, like, I met a bunch of colleagues who were also big real estate guys and women, and had an opportunity to go to China and work on a real estate project, consulting project in business school. And then went to India and studied at the Indian School of Business, did a real estate program in India for a while, and so, which became a whole another chapter in my life.

[00:26:37] Jason Rudman: It's a whole another chapter which I know about. That's for another time. That's another wonderful experience. I don't want anybody listening to think, Oh my goodness, there's a, like, a dark cloud associated with India. It's nothing but amazing.

[00:26:53] Derek Fleming: Fabulous, fabulous stuff that came out of India, but it was, you know, at the time for me being in business school, it was transformative to be on the other side of the world and be with, again, incredibly talented people focused on development and, reconfiguring space and communities. And so, by the time I got back from India, I was just clear. I was so settled. This was the end of my business full time. I also layered in entrepreneurship as a part of the curriculum while I was in business school. And so, I just felt, again, like, very directed and, focused.

And so, after finishing business school, [I] had some conversations with different people about directions where I would go, and I'd actually worked for a private equity firm the summer in between. So I did a real estate private equity internship and went down to New Orleans. This was just after Katrina.

They were looking for a plan, a strategy, for how to address what had happened in the Lower Ninth Ward. And so the private equity firm I was working for was a green sustainability firm. And [they] said, Derek, we're going to send you down there and look at the Lower Ninth Ward and help. We're going to figure out how we could put green homes and really address what's happened there in a sustainable way. And so that was, again, a whole ‘nother layer of wow. Like, now I'm in the Lower Ninth Ward; now I'm in New Orleans and doing real estate and revitalizing. And, again, it was just like these impactful experiences, you know.

So, by the time I graduated, I was definitive, but the market had changed a bit. This was in 2009. And, you know, some of the direction. in terms of, Oh, you're going to go to this firm. Are you going to stay here? Are you going to go to the private sector? Because now, this is supposed to be my pivot to the private sector. Those opportunities were there, but they were a little scarcer, right, because the market had contracted in 2009.

And so I'm having conversations with different people, and one of the conversations that was more intriguing for me was with a good friend of mine, who happened to be a celebrity chef, Marcus Samuelson. And, you know, [he] came in and said, hey, man, I'm looking to start a hospitality group. Marcus and I have known each other for a number of years. We've been really great friends, and while he was building his culinary career and won Best New Chef and all that stuff, we were good buddies. We were hanging out.

And so he says, when you get back from business school, we gotta talk. And so, when I got out of school and had all this real estate and entrepreneurial experience, it was like, I'm ready, Derek. I'm ready to start this thing. Let's do it. And so, we launched the hospitality group right out of, again. first came out of school. And so, there wasn't a job. It was this was an entrepreneurial endeavor that I embarked on.

And we were clear that we were going to start a venture in Harlem. As we talked it through, as we really investigated what the opportunity could be, we're both aligned with centering — we had another partner, Andrew Chapman — we're all aligned in centering this project as a culturally relevant, important, and uplifting enterprise for our community because we lived in Harlem, Marcus and I. And so, that was the birth of Red Rooster in the next, you know, chapter of my passion for real estate.

[00:30:54] Jason Rudman: We got a lot of ground to cover, so we should not skip past Red…that was Red Rooster, okay, and then I did other things. However, it is a true statement to say that Red Rooster is one of probably a handful of restaurants, Derek, that essentially changed the landscape of New York City. Beyond Marcus being a chef, restauranteur, author, you know, the greatness that is Marcus, and I would dare say the greatness in his partnership with you and who you are, buut it has such a relevance beyond simply being a great restaurant that changed the aesthetic or brought back this cultural aesthetic to Harlem. It's much bigger than that in terms of its impact.

[00:31:38] Derek Fleming: Yeah, and we had lofty goals, and we went all in on the culture and, you know, in terms of the art and the way that I designed the space. This was my first time getting my hands dirty in design and construction, and so I lived and breathed every piece of tile and woodwork and all the way up to, you know, every art piece. Marcus and I worked with Thelma Golden in curating all the art in the space.

And so, this was such an educational, it was a rough learning process, deep learning curve, to really do the design and development, but it was so educational and informative. [And] We were clear that we wanted this to be a gift. We wanted it to be an homage. We wanted it to be a representation of the best of what Harlem's historic, black, Malcolm X and 125th Street Intersection could be.

And, you know, we went all in, and we invested quite a bit. And we were getting some naysayers who were like, wow! Are you really going all in like this on that? Like, that's insane. We were like, no, this has to be purposeful, and it's gotta be something that is a destination, right? And I knew from my experience of now doing development that if you wanted to create place-making, you know, you had to do something that was game-changing and distinct, just out of the box. So that's what happened.

We had this partnership with the Studio Museum and with the Apollo, and literally like 2 months - before we even opened, actually -we got a call from the Apollo saying Paul McCartney is performing at the Apollo. [And] we have this partnership we're going to be doing with you guys, Paul is looking for a place to do an after-party, and we told him about Rooster almost being done, and you guys were almost there. So, we end up throwing a party for Paul McCartney.

[00:33:47] Jason Rudman: Of course you do. Just, you know, just Paul McCartney.

[00:33:51] Derek Fleming: Of course. I say this to say, you know, again, none of this was planned, but that happened, and then Bono did the same thing at the Apollo and then came to Rooster, and we had a whole celebration for Bono. And then there was Sting and Seal.

And then, after we'd opened the restaurant, we were barely open, and Marcus had just cooked for the White House; Marcus was the first chef to cook for President Obama. And so, you know, Obama was looking to do a big fundraiser. He was looking to do it in a place that represented the life and vitality of urban America. We got chosen as the place.

So then President Obama ends up coming to Rooster, doing a big dinner, having a whole experience. And this was, like, again, the first two months into opening Red Rooster. So you don't plan these things. right? They just happen. But, again, when you meet the moment when you meet the moment with your intention.

You know, had we just sort of, like, just try to do something kind of interesting with Rooster and just enough… But to actually go all in, you know, Marcus, Andrew, and I, we were committed to making this thing special. And my design on this was it wasn't high-end, but it was just really about excellence at every level. And so that became a beacon. I think we became a beacon for what could be.

[00:35:33] Jason Rudman: As I listen again, you know, it's almost a love letter to Harlem. Like the experience that you create, and there's so much, we could take this in so many different places. You know, there's a dose of luck, you know, McCartney's down the road, except that it's more about opportunity and preparedness. Right? Like, opportunity and preparedness, you know, a little bit of luck.

However, you go back I think, Derek, you have to go back to the fact that when you were working on a New York Empowerment Zone, you were connected to the very places that then paid it forward. Because with Marcus and Andrew, you had said it was excellence, but it's also high-end excellence. There's no, that's not a bad thing. It's really, really hard to do with low-end excellence. It just is, right?

And so your fascination with and your investment in every tile, in every piece of art, it ultimately, having been to Red Rooster, it's a museum piece on some level and a love letter to Harlem. And we also shouldn't lose sight of the fact that you're living in the very community in which you are changing the way the world thinks about that community. Because, again, at that time, Harlem was not idyllic by any standards, right? It's still going through this metamorphosis that continues today. Not quite, I think, where it was when you were doing the work with the Apollo, but certainly, you know, work to be done on that neighborhood, and still complex and economically challenged.

[00:37:15] Derek Fleming: Absolutely. In that context, when we think about what our opportunity was, not just to be a love letter, right, which could be like a beautiful jewel box. The opportunity was to be much more.

I have had these experiences of working for economic development agencies and empowerment zones, and really, understanding, wow, this is a job creator. This is a socioeconomic ladder for people to be able to participate in something that's going to train them, give them skills they hadn't had before, and give them an elevated, direct pathway to a whole new set of career opportunities.

And so, in that context of what was happening in Harlem at that time, this was a job creator as much as it was a new amenity for our community, for our neighborhood. But also, this, you know, kiss to the culture. It was like a warm hug to the culture. And because I've established these relationships with the Studio, with Thelma Golden, through the whole empowerment zone process, and with the Apollo Theater, these connections and relationships were warm by the time I was doing the development.

And so, it became like a very clear direction for me. Hopefully, we'll stand on the shoulders, as a new institution, of these places that you've helped support. But then also, you're about to create some great career opportunities, and so that is great.

[00:39:05] Jason Rudman: I'm going sell this a little harder, right, because, again, I don't want to underestimate the impact of the establishment of Red Rooster on the confidence measure of other developers and other like-minded business saying, well, if that works, then we should do something in the Harlem neighborhood.

[00:39:26] Derek Fleming: It absolutely was a proof of concept. It was proof of business, right? It was absolutely a catalyst. I mean, shortly after we opened, there were all sorts of developers who were now coming up past Central Park and hanging out and having lunch at Rooster.

And then once we heard that Whole Foods, in fact, was on its way, and again, we were having discussions with people, we're like, you guys are doing really great, this is really amazing, I think a Whole Foods would work here. Like, we literally were hearing those conversations.

[00:40:14] Jason Rudman: I think the point, Derek, again, having lived in New York without the resonance of what Red Rooster is, I find it hard to draw a link to Whole Foods saying, well, we're going to put a Whole Foods here. They might have eventually got there, but I think that that was absolutely a significant moment that enabled those conversations to happen.

[00:40:36] Derek Fleming: You know, it happened right across the street, the Whole Foods. And then, you know, there were fifteen (15) other restaurant/hospitality experiences that popped up around us in our immediate circle. And it wasn't lost on us that we had done a lot. We changed the footprint, the culinary, and the dining footprint of what New York considered to be spaces where they could enter and enjoy. And so, when the New York Post came out with that article, like, oh, the five places have changed, the New York, da da. You know, we were like, wow, that's crazy, you know. I guess we did. Like, that was pretty, you know, pretty phenomenal.

But what was more gratifying was all of the folks that became family at Rooster. Like, we were just, I felt like we were just having we had a living room, a living room that every week, you know, it was the Halloween party, it was the Christmas party, it was the, you know, the bachelor party, the wedding, the bridal shower. I mean, it was just so many wonderful memories that, You know, Marcus and I were able to experience through our community coming together at Rooster. It was just fantastic.

[00:41:56] Jason Rudman: But I think the point, Derek, again, having lived in New York without the resonance of what Red Rooster is.

I find it hard to draw a link to Whole Foods saying, well, we're going to put a Whole Foods here. They might've eventually got there, but I think that that was absolutely a significant moment that enabled those conversations.

[00:40:18] Derek Fleming: You know, it happened right across the street, the Whole Foods, and then, you know, there were 15 other restaurant slash hospitality experiences that popped up around us.

In our immediate circle. And, you know, it wasn't lost on us that we had done a lot of, we changed the footprint, the culinary, the dining footprint of what New York considered to be spaces where they could, they could enter and enjoy. And so when the post came out with that article, like, oh, the 5 places that changed the New York, you know, we were like.

Wow. That's crazy. You know, I guess we did like that was pretty, you know, pretty phenomenal, but what was, you know, more gratifying, more gratifying was all of the folks that became family at Rooster, like we were just, I felt like we were just having, we had a living room, a living room that every week, you know, it was the Halloween party.

It was the Christmas party. It was the, you know, the bachelor party, the wedding, the bridal shower. I mean, it was just so many wonderful memories that, you know, Marcus and I were able to experience through our community, you know, community coming together at Rooster. Yeah, it was just fantastic.

[00:41:56] Jason Rudman: It comes right back to…the community aspect is where we started this conversation, right, about what you know, how that fueled you, right, in terms of, you know, the arc of what you what you've done.

So phenomenal success in Harlem. Then you go to Harlem of the South, right, which is Overtown. And so, I'd love for you to talk a little bit about Overtown. Overtown, which was called Colortown in the Jim Crow era.

This is a Black community that was also the resting and the refuge spot. You mentioned some of the greats of Harlem. Similarly, in Overtown, the black mainstream players, you know, black mainstream artists that were booked at the Fontainebleau but couldn't stay at the Fontainebleau. Like, they stayed in Overtown — we're talking Ella, Billy, Josephine Baker, Nat King Cole.

You've got this neighborhood Harlem of the South, that is unapologetically Black, and then you go to Overtown, and Overtown that I described in that Black Renaissance era is not the Overtown that you experienced when you went there and well, okay…what might we do here?

[00:42:56] Derek Fleming: Right. Right. You know, after building Rooster and nurturing and getting that in a solid space, and so I was leading the development effort for the hospitality group, Marcus, and we were building things. You know, this opportunity, I got a call from a real estate colleague and said, “Hey, I need you to come down to Miami and look at something.”

And when she said that, you know, it was like, Oh, I know Miami. I've been there. She said, “No, no, no. I don't know if you've been in this neighborhood before. it's not South Beach. You gotta get down to come and meet me in Overtown.” So, I said, OK, and, you know, getting down there, and I have to admit, I had not understood, at all, the significance or even the geographic connection of what this fantastic, historically powerful place of Overtown was.

And so, I proceeded to just sort of be and spend time there. And my colleague owned property and was like, look, the city is really interested in revitalizing this historic African American district. And, you know, the real quick, not, you know, sort of doing it justice story of Overtown is that it was the birthplace of Black Miami between, you know, there was Coconut Grove, and then there was Overtown.

And Miami could not have been incorporated were it not for some of the men who lived in Overtown, worked on the railroads, came from the Caribbean, but they were actually brought in to sign the final proclamation for the establishment of the city of Miami because they didn't have enough people. And so, they used these Black rail workers to finalize that documentation.

And so, what you had in Overtown was this working middle class, actually, in segregated Miami, population of people, doctors, all the lawyers, the dentist, you know, hotels and restaurants, and it was really, if you think of Black Wall Street, you think of what Tulsa was, Overtown was Black Wall Street in Miami, thriving. And so, when they, the government, decided to put a highway literally, in the middle, as they did in several cities in the US, it obviously destroyed all of that Black progress, that Black entrepreneurship.

[00:45:33] Jason Rudman: Yeah. And when you say, like, literally, right, they cut the neighborhood in half, right, with the highway. And the neighborhood just precipitously declined. Literally, right? They cut the neighborhood in half, I think, right? The highway and the neighborhood just precipitously declined.

[00:45:42] Derek Fleming: Cut through where people were living, cut through social spaces, and so people, there was flight. People left. Like, this is, I can't believe this won't work. And the only people who could stay were those who couldn't, who didn't have the economic capacity to leave. So that, created an organic, poverty situation.

And then you layer that with, you know, sort of societal governmental neglect and racism that was prevalent at the time. And then, again, you've got the drug, the crack epidemic, which hit every major city in the U.S. So that became came the story, unfortunate story of Overtown for a few decades.

And so, then when the city decided, you know, and there are some people at the helm, in a decision-making capacity to revitalize and to change, I was contacted because I've done this work in New York, because I've done the empowerment zone work, because I, built Rooster, quite frankly.

“Marcus, Hey, we wanna talk to you about what that could look like down here.” And so proceeded to go through a planning process for the neighborhood revitalization and looking at a master plan. And as a part of that process, it was like, we've got this…there's a building here. And this building, which is right across the street from the Lyric Theater, and the Lyric Theater…

[00:47:08] Jason Rudman: I was going to say, if you tell me it's right across the street from the Whole Foods now, I'm going be like, hold on a minute.

[00:47:14] Derek Fleming: There's no Whole Foods here. There's no Whole Foods at all. Exactly. But it's right across the street from the Lyric Theater, which is sort of the Apollo version of what, you know, this venue represented for Overtown. Billie Holiday, Eartha Kitt, Sam Cooke, and Count Basie all played here at the Lyric Theater.

Right across the street from the Lyric Theater was a space that used to be a pool hall, right? In its era, as a pool hall, it was owned by a gentleman named Clyde Killens. And Clyde was just, you know, the brother who hosted everybody. If you were Black and came to Miami, you knew Clyde Killens. And so, he owned this pool hall, and Muhammad Ali, Aretha Franklin, Patti LaBelle, [they] would all hang out, and everyone would hang out in this pool hall to the wee hours of the night. And, actually, the pool hall was a site in the Green Book, right? It was a place of refuge. So, when people were traveling and needed a place of refuge along their travels from the South to the North, the pool hall was a stop within the Green Book.

So, the city came to me and said, hey, Derek, we got this pool hall here. We're trying to figure out what to do with it. Could it be a Rooster? And then this is in the midst of us planning the revitalization of a much broader district, a much broader footprint, so that became the next chapter.

[00:48:44] Jason Rudman: It's uncanny how related it is to the previous chapter and, again, just the thread of everything that you've talked about, where each chapter of what you've said “I'm going to do next” just builds on the previous one. And, you know, as I'm sitting across from you, it shouldn't be lost that there is just you know, there's joy as you describe these experiences.

Because this, to me, listening to you, it's not a job. It's so much more than it's…so how would you describe it if it's not a job, right, because I think so much of what we now, we go to work. Work is a job. I do something in order to put food on the table and to live the life that I want for myself. So, if it's not a job, well, how do you describe it?

[00:49:40] Derek Fleming: As you were formulating that question, Jason, there's an emotion that sort of hit over me a little bit. Because when I really think about it, it really is an expression of my family. It really is an expression of everything that was poured into me. When I think about my Dad who, you know, had me at a very young age, too young. He was 18 when he had me. But I do remember my dad reading books about the Panthers and reading to me books about Malcolm X, you know, and King. And he poured into me the importance of our culture and our history.

And he played music, and he loved Miles Davis. I say played; he's still very much here and alive and loves music, but my Dad taught me a lot of what I know about that part of the culture, of the aesthetic, right, the music piece. And my grandmother, both my grandmothers, you know, make sure that I went to visit our family in Indiana and back home, what we call it. And so, understanding the food, the basis for our coming together around food. Everything that…my Dad would take me to museums and things, you know, show me art. And so that was really foundational for me.

And so, when I marry that with the opportunity to have a pretty good education, and then, just like, the universe looking out for me with opportunities that organically presented themselves, it's like I dive into my work by diving into what's a part like, it's an expression of me, and everything that I think is beautiful about what I've learned.

When I hear certain music, when I hear Aretha Franklin, it's like, you know, it's like my Dad, my grandmother used to play that, and it's like, oh my gosh. Now I'm putting that in a playlist, in a space that really sets the tone for how people experience this historic building, like this pool hall where Aretha used to hang out. That just is very powerful for me.

And I'm doing it in a way that…it's a hurdle. Like Overtown's got a lot, and Harlem had a lot to lift, but it's like when you're lifting something that's like, you know, this is good. I know you're gonna love it. I know you're gonna appreciate it, you know, and so I'm giving you the best of what we have to offer here.

And not just Black people should enjoy that, but everyone should appreciate and enjoy that because it's beautiful. It's excellence. It's magic. And so that's why it doesn't become work for me because it's just sort of an expression of everything that I appreciate and love.

[00:52:33] Jason Rudman: I didn't know that we were going to get you emotional, but what I just love about that is, and the reason I asked the question, not knowing where you were going to go with it, is because I think it's a love letter to yourself, right?

I think the work that you've done and the work that you will continue to do to amplify and edify culture through urban renewal is as much a love letter to yourself. I think you started with your family, but then your family, what I was just listening to you, and again, for those of you that are listening, Derek and I have known each other for nearly three decades. However, Derek, we've not gone as deep as we have gone in the recent past and today on the why of what you do, right?

I mean, I know the story, but the why of what you do, and I just give to you, I think, on behalf of everybody that's experienced Red Rooster in Harlem and the Red Rooster in Overtown and everything that you're going to do in the future, on behalf of everybody, give it back to you and make sure that you're taking a moment to appreciate the impact that you've had through cuisine, through art, through music, through the aesthetic, on Black people, specifically, that are in those communities, but American people at large.

And I give to you again that I think it's a love letter to yourself because you're fully realized.

[00:54:04] Derek Fleming: Well, I'm still evolving. Right?

[00:54:09] Jason Rudman: Sure, because we're not done yet, But at the end of it, there is a level of realization and authenticity, and just I know me, what I'm capable of and what I want to do, that I think just comes out of this conversation that I don't think you get from everybody that you talk to in this life.

[00:54:25] Derek Fleming: Yeah. I mean, it is one of those things that you have to be; I have to count it as a blessing. You know, I have to be very appreciative that the stars have aligned, the universe has sort of been, you know, God has been behind me. It's not been golden and easy and smooth. There's been some rough patches.

But, again, following my heart, following my, you know, my passion and really having faith that it's worth it pouring into the culture, pouring into my passion, and it's all sort of just, you know, it's worked out in a really beautiful way.

[00:55:06] Jason Rudman: So, It's not lost on me that throughout this, what you've practiced is listening. Listening to yourself, listening to what's around you. You know, working within the communities that you serve is an art of listening because you're creating an experience that is resonant with the history of what they were and the vitality that you want to reemerge in each of those communities.

So, it's such an honor to actually have spent time listening to you with a story that's grounded in saying less and listening more to who you are and what it is the impact that you want to have on this world.

[00:55:51] Derek Fleming: Thank you, Jay. I wanna say this. The irony of how this really unfolds for me, when you think about it, is that a lot of the work that I do is about service and giving. And whether it be in the hospitality space, right, in service, in giving, and providing, and just, you know, I also think about, the fun of it all, right, in creating these, like, enjoyments, moments.

I love seeing people happy and having good, you know, and it's an opportunity for me to entertain. But the service of it, the service of building community, the service of providing new amenities and space, and the service of expressing the best of the culture for everyone else to enjoy. Giving and serving, you know, I think we all get a little bit of benefit out of like, oh, wow, it felt good to do that. It felt good to give. And I learned early on, it was like, that fuels me having, you know, being able to give.

[00:56:56] Jason Rudman: The More Elephant tagline, Derek, is listen, learn, live, better. You've basically just described, I think, the altruistic nature of, at the end of the day, who we are as human beings. I think sometimes we're so far removed from it, but at the end of the day, I do think a large part of what fuels many of us is to be in service of somebody else, to give somebody else joy through your actions and the impact that you take.

So Overtown. What are you up to now? I dare to ask what the next chapter is and where you're going to go next.

How are you reflecting on, you know, we've come through a pandemic, 2023 into 2024. What does the next chapter look like? What's the next idea that you want to frame and have a significant change story around?

[00:57:47] Derek Fleming: Well, what came out of the pandemic, ironically, we opened Rooster. Marcus and I opened Rooster, and our partner, Michael, in the middle of the pandemic, March. You know, we were gonna open, and then we delayed and did a whole program around food and, you know, providing, becoming a community kitchen.

But then we formally opened a restaurant that December, so we opened in the middle of the pandemic. And we got Best New Restaurant. We're been able to somehow piece together what now, you know, is a Michelin establishment, and it is giving the neighborhood something, this neighborhood that no one wanted to go to, that no one even knew about — flying to Miami, you go straight to South Beach — never knew anything about this historic, fantastic place. All these great people resided and socialized, and so now it has another reason. You know, Rooster was another reason to really celebrate, a new reason to celebrate Overtown. And so that's established.

In the midst of that, I was approached about joining a real estate firm, HR&A, which is a national firm that’s really focused on economic development, real estate development advisory work, and policy, or equitable policy, In communities across the country. So, I'm incredibly honored. I'm the senior executive here, and they've given me the space to build a practice around cultural capital; like, that is my practice here.

And so, I literally go all over the country and help municipalities and developers and philanthropy think about how to develop in an equitable way and keep culture centered in that process. So, that's really an extension, again, right, of, like, this is the through-line from, you know, Berkeley to Bayview Hunters Point, San Francisco, New York Empowerment Zone, Harlem, South Bronx, Overtown, and now I'm doing that work for a firm across the country at scale.

And so that's happening, but then also, I get approached about different opportunities. So, I was just informed that a project in San Francisco, in the Filmore District, which is the historic Black district of San Francisco, [the] jazz district. I joined it, I led a team to put through an RFP process, and we were just awarded a project to revitalize a 50,000-square-foot center, the Fillmore Heritage Center, in historic San Francisco.

And so that looks like, it might be the next entrepreneurial, you know, again, still wearing my hat here at the firm, but it looks like it might be the next entrepreneurial venture for me.

[01:00:35] Jason Rudman: I come back to anybody listening to this would say he's been really lucky. And what I would say is without opportunity and preparedness, because I think Derek, at the heart of this conversation, is a rabid sense of, I know who I am, I know the impact that I want to have, and I am prepared for when the opportunity comes. And if there's a little dose of luck that comes my way, I'll take it. You know, if it comes my way, I'll take it.

But at the end of the day, you don't get anywhere without the preparedness piece, and so I want to acknowledge that you start talking about, well, Filmore's coming, and we’re, “absolutely. Yeah. Of course, it is. Of course, it is.”

I'm waiting for you to tell me that, you know, the next opportunity is the fusion of Black community revitalization in China or something like that. I'm not, you know, it's not going to surprise me if somehow you connect those two places that I'm reading about.

Derek, it's been an honor, really, just to listen to your story. I'm so inspired and blessed to know you beyond this conversation. I feel like I've gotta go out and, like, do 100 push-ups and figure out what my next chapter is going to be based on just, you know, the fact that ...

[01:02:28] Derek Fleming: Can I say something?

I wanna say that, You know, again, knowing you for almost three (3) decades, but, like, our youth through our adulthood and now through our parenthood, I have been so impressed with you. You know, it's like when we talk about our parallel sort of backgrounds and upbringings and knowing how hard you have worked. And all the success that you've had, right?

I've always been so impressed and always been so really proud of you, man. And so now you're creating and building a new platform, and this platform here, which I think has such laudable, important merits to it. And so, I just, I mean, I continue to be proud of you and see how you evolve and grow and build, and you never let the grass grow under your feet. Like, Jay is always up to something new.

[01:03:01] Jason Rudman: I try not to, man. Try not to. No. Listen. I think we're 2 peas-in-a-pod on that. I think without experimentation, in a sense you're moving forward and you're learning, right?

Again, I think when you take a step back, Derek, I come back to why I created this platform. I'm not the right messenger, clearly, for all of the stories I'm talking about, right? Like, you've got your message of what you know, of who you are, and what it means to do this work. That's what I wanted to create because I am infinitely interested in those types of stories, and I think many more people are.

And so if we can give an opportunity to get these stories out and inspire a new generation of thought leaders to think differently about how they interact and the impact that they have on this world, if we do that for 1 person, Derek if this conversation impacts just 1 person, then it's a win.

How do people learn more about Derek Fleming, about the work that you're doing, about HR&A Advisors?

[01:04:06] Derek Fleming: You know, so folks can go to my LinkedIn page. I actually need to get better at that, Jason, just in terms of, I'm not the biggest social media person, you know, I'm periodic. I, you know, mostly pour into the kids and that sort of thing.

Like sharing what, you know, I feel like my IG is like, okay, Dex and Zane are going to be able to look back 15, 20 years from now and see, like, where they were what they were doing in May of ‘21 or some you know, it's like, it's their site, essentially.

[01:04:35] Jason Rudman: You mean if we didn't create a photo book for it? Oh, that's another… So, a whole another chapter. We're going to come back, and we're going to talk about what we've learned through parenthood, Derek. That's the next conversation.

We'll make sure that we feature your LinkedIn in the show notes so people know how to find it. Awesome.

Final question, Derek. If you were to boil this down to one thing, like one element, one More Elephant moment you would leave with our listeners about your story, your experience, what you've been able to do - could you encapsulate it in one central thought that leaves people with a sense of, I can do that too?

[01:05:15] Derek Fleming: I would say work hard, and work incredibly hard in following your passion and pursue it with faith. Because if you work hard at something that you're intrinsically, authentically interested in, and you have the faith that everything that you're doing is right, is just, is giving, is for benefit, and you have faith in that, you're going to be fine.

So, whatever that means, whatever that is for anyone if you are, you know, working hard and you're true. Right. You're true to it. Like, you're passionate, and you're true to what is what's bubbling up inside. Like, what just like, oh, excites you. Like, brr, brr, brr, you know, and then you have faith in that, you're gonna be good! That's where I think I wanna leave.

[01:06:14] Jason Rudman: I appreciate you, man. Thank you, thank you, thank you so much for your time. I'm inspired. As I told you, I think I've got to kinda scratch the 100%...I feel like, after this conversation, I've got to go and do something. I'm not too sure what it is. And it looks but, again, I think that comes back to what, you know, we we like a few plates spinning, Derek Fleming. We like a few plates…

[01:06:35] Derek Fleming: Thank you for having me.

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