Serial entrepreneur and brand technologist, Hajj Flemings, joins Cayden to offer insight for Black professionals adjusting to life in corporate America and to talk about the stereotypical “brand guidelines” that bind their hands.


CAYDEN BROWN: Hello. How are you?

HAJJ: Doing good doing good. How you doing? 

CAYDEN: I’m good. I’m very glad to hear that.

HAJJ: Glad we can connect. 

CAYDEN: Absolutely. Thank you so much.

HAJJ: Oh, yeah, it’s all good. So, how’d you get the idea for the series?

CAYDEN: You know, I always did a little bit of commentary. People would consistently ask for my opinion on social issues, because I would always be so outspoken about injustices. And so, multiple people had told me a few months ago, “you need to start a podcast.” And I’m like, I don’t really have time. But I thought a blog would be a perfect way for people to be able to read at their own leisure, whenever they can, and it’s up there forever. I thought it was a very good idea. And I really wanted to make sure that it was a transcript of a conversation. Because I think the most- that’s what’s kind of missing in the community right now is the tabletalk discussions that we have at our family gatherings about these things. Those are the most impactful to me, personally. So that’s what I want to bring to this.

HAJJ: Okay, gotcha, gotcha. And your Jacob’s son, right? 

CAYDEN: I am! 

HAJJ: Okay, cool. Cool, cool. I thought to myself “I’m pretty sure that’s his son so, yeah. That’s, my guy. So man, proud of your father doing his thing. I don’t know it might have been 10 years ago at Central Michigan at a speaking gig and you know, just seeing him taking off. But also note, it’s always good to be able to see the next generation doing their thing. 

CAYDEN: Thank you so much. It’s funny. When I had got the notification that you followed me back and were willing to be a part of it, I went and showed my dad so fast, and he was like, “That’s my friend!”

[Both Laugh]

CAYDEN: I was like, dang, I could’ve jumped over all this.

HAJJ: [Laughs] It’s a small world. 

CAYDEN: It truly is.

HAJJ: So yeah, let’s get it though. 

CAYDEN: Let’s get it!

CAYDEN: Well, I really wanted to ask you about your experience, just seeing everything that you’ve done, especially with your Modern Athlete. That’s something that I really relate to. The things that are on on them. I wanted to know why you created that brand. What was your reasoning behind that?

HAJJ: So I’ve always had a love for fashion. So so when I was in college when I was about your age, I worked for a all Black footwear company called ‘Movataye Footwear.’ And so I was an engineering student, I had had already written every single footwear company in the continental United States. Like I literally sent letters. And back when I was doing this, this is back in like ’89/ ’90. So there wasn’t a website, there wasn’t big internship programs. And I couldn’t go online and look at this stuff, I had to send them a letter, and hope it got to the right person. And hopefully they sent me something back. But I ended up working for Movataye Footwear. Our lead designer was D’Wayne Edwards. D’Wayne Edwards runs Pensole Academy, which is a HBCU in Detroit. 


HAJJ: I didn’t even know that there was an HBCU historically, he was able to get it resurrected and run something called Pensole Lewis Design Academy. So he’s the former, lead footwear designer for Brand ‘Jordan’. He left there started this and has been doing his thing. So I self-designed sneaker back when I was in college, a sneaker made it to the market. You know, I interned in New Balance. So, I love sneakers, and you know, and clothes and stuff like that. We also did an apparel design company called ‘Glorify God,’ 


HAJJ: Which was kind of like Fear of God, like 25 years ago, like, we did all the same stuff about 25 years ago. Obviously, his took off a lot, you know, a lot bigger than ours did because we’re working with the church. So that’s kind of some foundational things from a design standpoint. But Modern Athlete was birthed out of out of a health challenge. I had a tumor where I got it removed and I got diagnosed with cancer. And they wanted me to do chemo and other kind of stuff. And I was like, I just want to, I want to go about it from a from a holistic standpoint. And so I did. And so in that process, I realize that there are athletes around us that might not make it to the league. So, it’s really about defining a new class athlete, which are just high performers. People who are doing amazing work. And that’s where the concept of a modern athlete came, came into being because we all have routines, we all have things that help us to be able to do the work that we do, even if we’re not doing it professionally. And so the concept for Modern Athlete, derived from that.

CAYDEN: I love it. Now, you call yourself a brand technologist.

HAJJ: Mhm.

CAYDEN: What does that mean to you? Can you break that down to me? 

HAJJ: Yes, yes. So for me, like, I play this intersection of branding, marketing and technology. And one of the things that from a brand standpoint, you always want to try to figure out how can you own the space? So there’s a lot of people who are brand strategists and brand experts. But if you go do research on brand technologist, there’s really not a lot of people in that space.

CAYDEN: Right. 

HAJJ: And so I said, let me let me plant my flag in that area. 

CAYDEN: I love that.

HAJJ: Because every brand is trying to figure out how to integrate technology. So if you have Nike, there’s NFT’s and they are acquiring different companies, or there are people who are doing stuff in the Metaverse. And we’re pulling AI into all of these things where we’re creating all these different experiences or even if it’s doing stuff that’s social. So every brand has an aspect where they’re pulling things in from a technology standpoint. And I see that so I’m going to, you know, that’s intersection that I’m already in anyway, but I’m going to coin it that because nobody else is doing it. And so that’s really kind of how I configured or constructed that name. So even in terms of the work that you do, figure out how you kind of position yourself if you look at Tim Ferriss, he wrote ‘The Four Hour Workweek.’ And so it’s an amazing book. When he came out with the book he decided to call himself a lifestyle expert. And so that’s really kind of how I came up with that. But we do a lot of work in technology and branding and marketing. So we’ve got a lot of work helping small businesses do their digital transformation journey. And that’s kind of how I constructed that.

CAYDEN: I love that. I feel like that aligns perfectly with what Trespass is about. Because the whole point is to make sure more people who look like us enter those spaces and start dominating in those spaces. And so I love hearing that story. On the topic of branding, because that’s, you know, I’ve worked in branding spaces as well. I know that when it comes to speaking about a brand of any entity, there are guidelines to that brand, right?

HAJJ: Yup.

CAYDEN: So I kind of put a twist on it when I’m thinking about this, which is why entitled this segment ‘Rebranding Black.’ And I think for so long, there has been a stereotypical brand, image, you know, whatever you want to say, regarding our community.

HAJJ: Yep.

CAYDEN: However, I’m seeing more and more people like you and I, and, you know, my father, etc, who are starting to kind of defy those guidelines placed on us.

HAJJ: Yeah, yeah!

CAYDEN: I wonder what your experience has been integrating from being a small entrepreneur to starting huge companies. And what your experience has been trying to break down those guidelines and make new ones.

HAJJ: Yeah. Lots of times, people want to put you in a box. 


HAJJ: And so, you know, it’s really up to you to not allow people to define you how they met you. 


HAJJ: Right. So, so if they met you, and your student and you’re doing one thing, you know, so they like to typecast. And again, like, so that happens to actors, it happens to, you know, athletes, etc. So people will -put you in a box. So it’s really up to us to make sure that we don’t get defined. So where God has put a comma, other people want to put a period.


HAJJ: And so you become jest to somebody else. Where it’s like, you know, as a person, we’re not monolithic. We’re not just one thing. And when I say that, I did a lot of other stuff out there where people are trying to get into things that don’t jive with what I believe in, you know, and they try to try to marginalize and put a whole bunch of other stuff into it. But the reality is, is that if I look at myself, like I love branding, but I also love fashion. I love storytelling. So if somebody says, “Hey, you can only work with this type of small business,” I’m like, “No, I can work with them. But I can also do work with Nike.” And when Nike got the community store downtown, they reached out to me to do the casting, to identify models, and to be with them to shoot this stuff. 


HAJJ: Now, I had not at that point, I really did casting like that. So I could have said, “well, you know what? I’ve never done that before. So I’m not going to do that.” 

CAYDEN: Right.

HAJJ: But Nike is one of my favorite companies. I know what aesthetic looks good, what they’re looking to do, and we’re able to make it happen. And so I say that to say, you know, sometimes you have to create your own table. Sometimes, there might not be room at the table. There might not be a chair at the table for you. You might not get invited to the table. But at the end of the day, I believe that everybody has a God given purpose. 

CAYDEN: Absolutely.

HAJJ: And one of the things that I talk about is, is genius culture, and people identifying the genius that’s inside of them. And part of that, one of the aspects is understanding your God given purpose. And so when I understand my purpose, I don’t let other people define me, or stop me from getting to where I want to go, right? Because at the end of the day, I believe everybody’s selfish in buisness. And I’m not saying that that’s a bad thing, but at the end of the day, everybody’s looking out for their personal needs, and they’re not looking out necessarily for you. And so you have to find a way to say, look, you know, what, you know, even if you don’t care whether this is a success or not, I put in my blood, sweat, tears, my money, my finances, my time and my energy. And this is going to happen with or without you. And so I try to change their mindset. 

CAYDEN: Absolutely, I love every single thing that you just said. And it leads me exactly where I want it to go. Because back to what you were saying about having to create your own table. And we’re not monolithic. I think that a lot of times- and I want your opinion on this, being in that space, but I think a lot of times those brand guidelines, quote unquote, that our community is binded by, we tend to not break away from that. And we tend to follow that. Like, if you have ever heard somebody say, “Oh, Black people have to work 10 times harder to get this, this, this and this.” There’s a lot of truth to that statement, but I feel like we often put a cap on ourselves and put our own ceiling there. 

HAJJ: Yeah, yeah… Yeah. So in fact, sometimes we have to work harder. But at the end of the day, it’s gonna make us better. Right? And so, is it fair? No. Do other people start on third base sometimes? Yep. You know, so like that’s, that’s how it goes, sometimes at the end of the day, don’t allow that stopping you from doing what you’re doing. Like, you’re going to have a chance to be able to connect with people and to do things as you get older, and when ask people for favors now, or for interviews, they might be slower to do it. But they’re more apt to do it because of your age. So you have to leverage the timing, and the opportunity that exists. And you use to your advantage. Because other people that don’t look like us, that’s what they do. 

CAYDEN: Yes. That’s so true. 

HAJJ: So, we gotta leverage everything. 

CAYDEN: Absolutely. Absolutely. What is your advice to people like me? People my age who are trying to trespass into these spaces that nobody like them really has, or where they’re unwanted?

HAJJ: Yeah. So a couple of things is that failure is not an option. You know, so lots of times, we look at failure as being permanent. And just because something didn’t initially work out, or the path that you thought was going to work, didn’t didn’t work the way you thought it was gonna work. It doesn’t mean that your time it doesn’t mean that it’s not gonna work. You know, it might just mean that you might need to have another path to get there. Also, this age, you have more time now than you have at any other point in time in your life. Because I’m assuming that you’re not married right now. 

CAYDEN: [Laughs] Right.

HAJJ: Okay. So, you know, I have responsibilities where I can’t just do what I want to do. Right? So now, you you don’t have the full amount of bills that you’ll have later on in life. You don’t have the responsibility of a wife and children, all those things. So right now, you can be selfish.


HAJJ: You can experiment, you can try stuff, you can launch a content platform or a content company. And you can test it out. And you can experiment. And what I would say is I would go for it, because putting in the time now, put you in a position down the road, that you can do stuff that other people won’t be able to do. Because over time, as you build this up, you want to be able to interview people that you dreamed of interviewing. And so it’s an interviewing somebody like me will end up being like, small potatoes down the road, there’ll be like, “Okay, that was cool, he was good.” But when you have a chance to interview Mark Cuban’s of the world, Richard Branson’s, or to Kevin Hart’s, you know, I’m saying, like, people like that, you know, so interviewing me is more of a stepping stone to something bigger. But you have people who you can now connect with, because you’re telling their story and then now other people want to tell your story, where Oprah wants to tell your story, or Good Morning, America wants you to come on and say, “hey, look, you know what, there’s a young cat from Michigan, who is telling amazing stories, and inspiring people to live their dreams.” Right? And so I think for you, part of it is to think big, you know, if you can do it in your own strength, then you don’t need God, and you’re not thinking big enough. 

HAJJ: Because like at the end of the day, people don’t remember or think about the people that follow the rules. And again, I’m not saying to do stuff illegally. What I am saying is that, if we think about the Steve Job’s in the world, we think about the Mark Zuckerberg’s. Those are the people who were able to figure out ways to do stuff that was not the regular, standard way of doing it. And those are the people that we talk about, and that we chronicle. We don’t talk about people who color inside the line. 

CAYDEN: Absolutely. I love that. And that’s so true. And it’s also something I see now, I know that being not only Black, but also a child. 16 years old. People don’t really look at me as somebody important until they see my work. You know what I’m saying? They don’t look at me as somebody who can produce the things I talk about. How were you able to keep going in the midst of having little to no support?

HAJJ: Yeah, you know, “the journey of a thousand miles begins with a single step.” And so even when I pitched to big companies, what they know is what they can see. You could pitch ideas to people all day, and it’s like, okay, but once you have proof of concept, then it’s gonna be easier to get sponsors and strategic partners. When they can look at “Oh, okay, he went and started, etc” it’s going to be easier to be able to do something with it. You can point people to stuff that already exists. Right? And so, it’s about putting something into the earth. It’s about taking a concept, and being able to construct that idea, so that people can experience it. And then that’s going to open up doors. So, don’t worry about the people that don’t see your vision, because it’s not for everybody. God gave you the vision, and so everybody’s not gonna see what you see. Everybody’s not gonna want you to be successful. And again, I’m not saying people are gonna be against you. I’m just saying that everybody might not run through a wall for you. 

CAYDEN: Mmm! I needed to hear that.

HAJJ: And that’s okay. Because there might be something that you have to learn, and you have to get it out of the mud.

CAYDEN: Absolutely. That is 100%. What I’m feeling right now, definitely appreciate it. The last thing I want to touch on with you is- back to the brand guideline piece- we talked about how there have been historical brand guidelines placed on our people, we’ve talked about how to break out of them. But I want to talk about what are the new brand guidelines? As a brand technologist. What would you suggest our community start doing in the rebranding process?

HAJJ: So I will say, in a lot of things, people are going to put a lot of stereotypes on us. 


HAJJ: And again, going back to the idea before, they want to try to put us in a box. And so people might think that it’s not gonna be quality, or it’s gonna be ghetto, or it’s gonna, you know, it’s gonna be okay, or we’re not as smart as somebody else, or somebody who comes from a certain school or background or family dynamic, you know, there’s is gonna be better or they have, or they went to an Ivy League school. And so, you know, sort of might be certain things that, you know, that other people can check the box on that maybe we don’t have and so. And so they tried to place us in this box. And so what I would say is, be excellent. Whatever you do, you know, you want to be excellent. So there’s a term in a business called ‘first mover advantage.’ And so sometimes you get opportunities because you’re the first one there.

CAYDEN: I really, really appreciate your insight. It was very wise and it’s something that a lot of young Black people- and all people, really- need to hear. So thank you for coming and dropping gems on us.

HAJJ: Yeah, yeah. If there’s anything else you need from me, let me know.

CAYDEN: I will, thank you!

HAJJ: Absolutely, just keep me posted.

CAYDEN: Alright, I’ll speak to you soon.

HAJJ: Alright. Bye bye.

Featured Image: Kevin “WAK” Williams

Production: The Black Art Depot

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