There are a lot of people who inspire me, but very few of those are actually people whose numbers I have in my phone. This man is one of those. Against all odds, he worked his butt off to start Dreamapolis, a nonprofit that empowers entrepreneurs to change the world. Add to that his wit, down-to-earth personality, and good looks, and ladies and gentlemen, we have a gem. This was by far one of my favorite interviews so far and I’m sure you’ll love it too. Follow him on Twitter at @DreamerinChief and like the Dreamapolis Facebook page!
HMHW: What do you look for in a group of friends at this age?
Derrick: I look for my friends to be open-minded, adventurous, free-spirited, and have some intelligence. It’s not a requirement to be socially conscious but it’s definitely a plus.
HMHW: Fill in the blank: I am a closet _____ fan.
Derrick: *without hesitation* Justin Bieber.
HMHW: Really?? I’m judging you right now.
Derrick: *proceeds to sing not one, but TWO Justin Bieber songs*
HMHW: Moving on, do you have a type/believe in types?
Derrick: A type of what?
Derrick: Yes, I do believe in types. I’d rather call them preferences; I have my own preferences in women. I really desire to find a woman who is like my mother. My mother is very independent, ambitious, extremely intelligent not just in terms of book knowledge but also in terms of intuition. She is extremely resilient – she doesn’t give up despite the odds or despite what others may say about her. And she’s beautiful and God-fearing. I mean, what else would you want in a human being? So that’s what I’d say my preference is, but it’s very challenging to find especially in this day and age.
HMHW: Do you see yourself remaining in the same career for the rest of your life?
Derrick: If I have a choice or if I don’t have a choice?
Derrick: If I have a choice, yes. Unless Sallie Mae comes down and takes away everything I have, I want to continue to do this until Jesus comes back.
HMHW: Do you feel like you’re held to an impossible standard of perfection as a man, coming from women?
Derrick: Yes. Absolutely. I don’t want to sound like the victim – men are not the victim here. But it’s fascinating that women have these standards of what men should be, and a lot of times they’re influenced by media or by the 0.5% of men who are superhuman. And they think all of us should act that way. So we can never be sensitive enough, we can never be emotionally engaged enough, we can never be enough. And it’s fascinating that even with the women we do try to be enough for, there’s always something that we don’t have because women are so different, and each one wants a different set of things from men. More often that not, we’re inevitably going to be inadequate.
And I’m gonna get on my soapbox for a second. So I tweeted that one time that men have these expectations to treat women like queens, right? At least, I was raised to treat women like I want my sister to be treated. But in the same token, women don’t have that same standard or expectation to treat men a certain way. I just think that in relationships, the gender norms that society says we are to adhere to are a little unfair.
HMHW: Do you have a definition of guarding your heart and what does that look like for you?
Derrick: *laughs* Oh man. I’m just gonna be honest with you, and this might get me ostracized but it’s okay. At one point, I would say that I believed in the whole “guarding your heart” thing, and I believe it’s important to guard your heart. But at the same time – excuse my French – I also think it’s bullshit. People use that phrase to justify their behavior. So maybe there’s a guy that they like, or there’s something they really want to do in their hears, but they refuse to take that risk or make that move because they’re “guarding their hearts”. I think that phrase is one that’s often misapplied. The way that I live is to believe in something, be a 100% behind it and if I feel like there are some holes in it, then I’ll throw it to the side. I think I’m prudent, and if I do my due diligence, then I’m going to go full force behind it. But I think that verse is misapplied and I just choose to dismiss it.
HMHW: How valuable are friendships with your own gender to you?
Derrick: They’re invaluable. Iron sharpens iron as one man sharpens another. So I would say that the men I surround myself with have been invaluable in my personal and professional development. They keep me accountable, they say things to me that, frankly, I don’t like to hear. Most of it is unsolicited, but still very valuable. Even if I wish I didn’t have them around most of the time, if they weren’t there I could only imagine where I’d be. That sense of being a part of something much bigger than you is invaluable.
HMHW: What about friendships with the opposite gender?
Derrick: I don’t have many friendships with women, to be honest with you.
HMHW: Do you feel like it’s difficult to maintain friendships with women? And why?
Derrick: Are they attractive, or not?
HMHW: *insert uproarious laughter here* I love that! Um, both.
Derrick: You and I can’t be friends. I think I know enough about you as a very attractive woman to know that it would be difficult to “guard my heart” in a friendship with you. Inevitably, I would keep trying to build persistence and it would become uncomfortable for you. And because there’d be so much ambiguity in that relationship, it would just never work. And if you keep getting closer and closer emotionally, all that romantic stuff is just right around the corner which makes it impossible to just be friends. So I think that if there’s some level of attraction, it’s impossible for men and women to be just friends. If there’s no attraction, it’s very easy.
HMHW: Best/worst advice you’ve ever been given on the topic of love and relationships?
Derrick: The worst advice I ever got was that everybody gets lonely and everyone needs love. And “love” wasn’t being used in a romantic sense, but in a physical sense. So essentially, I need to just go out and get laid. The best advice that I’ve gotten was probably from my brother. He told me that instead of looking for the perfect person, I need to focus on myself and become that person for another. So as opposed to placing my focus on something that’s external and that I can’t control, he advised that I should focus on the things I can control, like my character, my work ethic, etc.
HMHW: Do you believe in the one? And if you do, do you believe that the person’s been chosen for you since the beginning of time or that they become the one when you choose them?
Derrick: Well, I’m an idealist at heart. So yes, I do believe in the one. However, I’m also a realist, and given divorce rates that continue to get worse and the existence of cultures where there are arranged marriages, I think there might be evidence that suggests otherwise. But personally, I want to believe that there’s “the one” out there. If I were to answer for everyone overall, I’d probably say no.
HMHW: How do you make decisions about this season of life and has that changed from before?
Derrick: Previously, my decisions were made in a very calculated way. I would take a lot of time to think about it, ask for a lot of advice and opinions, and given their consultations, I would then make a decision. Now, I’m not as fearful of making mistakes or being labeled as a failure. I may still consult people and have those conversations, but it doesn’t paralyze me the same way that it used to. I’m definitely more spontaneous in my decision-making because that fear of failure or being rejected by others isn’t there anymore.
HMHW: How far in advance do you think/plan/prepare for?
Derrick: I have my life planned up until December 21, 2012. That’s the end of the Mayan calendar, baby! Okay, that was a joke. My life is planned up until probably Sunday. I probably plan a good six days in advance, and after that whatever happens, happens.
HMHW: What’s your perception of the differences between masculinity and femininity? Do you think there’s a difference in roles based on gender, or that it varies from person to person?
Derrick: Oh no. Oh no!
(Editor’s Note: If only facial expressions could be transcribed…)
HMHW: You thought this was gonna be easy but it’s NOT!
Derrick: I think the differences are a myth. I think there aren’t specific ways a man and a woman should be. They should complement each other – because the man might be better at some things and the woman might be better at others. But I think the roles are a social construct and are really just a myth.
HMHW: What kinds of things challenge your masculinity?
Derrick: Is everything too broad of an answer? I wear these glasses with a tortoise-shell print on them, and the number of times I’ve been called gay has increased exponentially since I started wearing them. I get labeled as not masculine enough because of what I choose to wear or because I use this vernacular and I’m a man who also happens to be black. I’m told I’m not manly enough because I’m not constantly dating women, because it’s been a while since I’ve been in a relationship. So, really, everything.
HMHW: Do you feel a pressure to be thinking about/preparing for marriage based on your age? And if so, is the pressure from within or without?
Derrick: Yes. And the pressure’s from both.
HMHW: Do you think you’re making the most of your single years?
Derrick: Absolutely. I’m living my dream! It’s not easy, but it’s definitely worth it.
HMHW: What did you believe about romance and love a year ago that you don’t believe anymore?
Derrick: I used to be a lot more conservative than I am now. I believed in the attraction-courtship-marriage-make babies model. In fact, I knew someone who didn’t even believe in dating. If you found a woman that you liked, you courted her and married her. Now, I’m not so conservative. I think it could still work that way, but it doesn’t have to. And here’s the thing, I have no problems with kissing my woman. As long as there are boundaries which have been previously discussed, then I think kissing is okay. But a year ago, I would’ve felt completely uncomfortable saying that.
HMHW: Most embarrassing dating story.
Derrick: I took this girl out on a date to a really fancy place, and it was right at the beginning of trying to get Dreamapolis started so I had zero money. I decided I was gonna donate plasma so I could pay for this date. I donated plasma that afternoon and then we went on the date. So you know, I’m sitting at the bar having a beer before my dinner. And all of a sudden, I get really hot. I’m sweating like I’m playing a basketball game, it’s crazy. So I excuse myself to go to the bathroom. But when I stand up I am so lightheaded! So I decided to go outside and get some air – maybe it would help the lightheadedness. And before I knew it, I was face first on the pavement. I had passed out. When I came to, there was dirt and grass everywhere, and a group of people standing over me. I got up and went back inside the restaurant. Somehow the manager of this restaurant had heard and came out to try and find out what happened, and then I found out someone had called an ambulance. And I was like, “Oh hell no, I’m not getting in no ambulance!” There was some kid who ran in screaming, “He had a seizure! He had a seizure!”
When the paramedics got there, they asked why I was so dehydrated. And I’m thinking, “There’s no way she’s gonna hear that I donated plasma to be able to pay for this date.” So I was trying to think of some lie to tell. I told them that I had given blood earlier in the day – which wasn’t completely a lie. But they took me to the hospital to run some checks and then I got discharged. And I never heard from the girl again.
HMHW: She didn’t even call?
Derrick: Nope. But at least I knew from then that we wouldn’t have worked out. So it’s all good.
HMHW: Do you believe in the ability to be “ready” for marriage? Do you have factors you think will indicate your readiness?
Derrick: I don’t think you can be ready. I think you have to 1) accept that you’re never gonna be ready, 2) know that it’s probably gonna get worse before it gets better, and 3) learn how to communicate well. Without communication, it just won’t work.
HMHW: What are your thoughts on modesty and its effect or lack thereof on daily living?
Derrick: You know about my obsession with sundresses!
HMHW: Oh yeah I do.
Derrick: I’m the kinda guy who’s turned on more by what’s left to the imagination than when I’m shown all the goods. And what’s that they say, why buy the cow when you can get the milk for free? That might be a crass way to put it, but it’s the same idea.
HMHW: What are your opinions on pursuing/being pursued with regards to gender roles?
Derrick: Personally, I believe I should take initiative at first. But I also think it’s sexy when a woman offers to pay, or when she takes me out on a date. But that never happens.
HMHW: You’ve NEVER had a woman offer to pay?
Derrick: Not one time. And you know, I have a very strong personality and I start off by paying for things and initiating things, so I think they settle into the pattern and come to expect it. And then they never change it up.
HMHW: Wow. What kind of women live in Indy??
Derrick: Haha and you know, it would also be nice to just have a woman come up to me and start conversation. Or at least respond when I do. Like the other day, I saw this woman and I thought, “She’s really pretty, I should go talk to her.” So I walk up to her and try and make conversation, and you know what she says? “I really have nothing to say to you right now.”
HMHW: What would you say has been the hardest part of being a 20-something?
Derrick: Learning to like who I am, and not compare my happiness to others’ happiness. I could complain about how I don’t have what they have or I’m not doing what they’re doing, but I’m learning to realize that God has me in this place for a reason and I should be happy here.