To the Moon & Beyond: A Personal Journey and Solid Financial Advice from Entrepreneur, Mr. Henry Culbreath - Part I

Recently, I had a chat with an old college colleague, whose story is both inspiring and profound. He went from growing up in public housing in DC, to being a self-employed entrepreneur of two successful businesses. He has a passion for teaching financial empowerment and literacy, and I think he is the perfect person to kick off my ‘To the Moon & Beyond’ interview series. We chatted for over an hour, and as a result, this interview is delivered to you in two parts. I hope you are as inspired as I was by his story to get fiscally motivated to reach new heights and push yourself beyond self-imposed barriers.

Let’s start off with your current occupation.

I’m self-employed and I have what amounts to two core businesses. I have Culbreath Estates which is a cluster of properties in the DC Maryland area, houses and other units.  I rent to relatively moderate to low income families. I also have a company:  Children, Children, Children Inc. It provides educational and other social services to children and teenagers from disadvantaged backgrounds, so it could be those who have been neglected or abused. My largest contract is with those in the juvenile justice system. Helping them to achieve their educational goals, secure their GED, graduate from high school, and even get involved or engaged in post-secondary programs. Going off to college and what have you. Recently,  I’ve just noticed the distance or the gap if you will, between myself and so many hard-working or well-intentioned folks that I’ve taken on a passion to give financial advice or financial consultation to the 9-5er, on ways to ultimately secure wealth or be as close to financial independence as possible.

What was your background growing up financially?

I was broke. Very much so. Actually, my mother was a heroin addict. My father was a heroin addict. I was ultimately adopted by my aunt, who had to raise me along with three of her children in DC public housing. I was in DC public housing until I went to college. Hobart & William Smith. Now interestingly enough, my father was released from prison when I was a teenager, early teen, and he got back in my life and remained cleaned and out of jail and so I was able to build a rapport and a relationship with my father.  I did have the guidance of my father in my teen years. Very important. You need someone to whom I would hold myself accountable (sic). Right? That was important. I grew up in the public housing projects near Howard University, so I always looked at Howard students and I would see them walk by and I remember two guys. I’m not in contact with them now, who really, really inspired me. I was in an afterschool program. They worked there and I would see them there.  I also had the sad privilege, Javi, of watching, I call them my brothers, but they’re really my cousins, because I was raised by my aunt, right? My older brother just being in jail the entire time I’ve known him,  so I’ve learned early that the street game does not work. Now this was during the crack era so quite frankly I should have been swallowed up.  I watched him in and out of jail and the brother behind him, he was in and out but then he figured it. I watched things fall apart around me. The women who raised me, God bless her, did her best, but she was very abusive. Physically and verbally. I’m sure that creates problems in my personal life.  I always had a chip on my shoulder; I’m going to show them. I know I’m the adopted kid. I know my parents are on heroin and I used to get teased to be honest with you. “Your mom and dad are on heroin’ I remember keeping this chip on my shoulder. I said to myself, “but, I’m going to show y’all”. So I‘ve always had that silent motivation.

I always had a chip on my shoulder. I’m going to show them. I know I’m the adopted kid. I know my parents are on heroin...So I’ve always had that silent motivation.

 The turning point

The thing that really caused things to turn for me was when I got into high school. I got into ROTC and I have a natural kind of alpha male personality. I always kind of liked the idea and the regimen of being disciplined and following orders so I latched on to that. There was a junior ROTC program in my high school so I latched on to that and I was very successful at that and I probably could have gone on to the naval academy but I was always fearful of going to the military and still had my aversions to serving in the military, to make a long story short, I learned a lot about discipline. Our motto was “Practice doesn’t make perfect. Perfect practice makes perfect,” so I focused myself academically to the point where out of 240 students, I was ranked #4.

Practice doesn’t make perfect. Perfect practice makes perfect.

Those who knew me knew in high school back then, would say it would not surprise them if I came out from the woods and was running for mayor of DC. I was really slated to be politically, the GUY. Interestingly enough in the 90s, I held an office. I had an office in downtown DC. I was the student member the Board of Education so I literally served on the Board of Education.  They only elect one student each year and I don’t think that they do it anymore. I had to go to a fair, give a big speech, campaign. So I was elected to represent at that time  80,000 students. I was a very politically oriented guy and was slating myself to do that. Now I’ll be honest with you, when I got to college, I was studying political science at HWS, and English and economics right? And I learned something. My goal was to study political science, come out and do politics. And then the Monica Lewinsky thing happened and you can share as much of this as you want because I like to share the whole play and what my evolution has been. I realized it’s hard to do politics and have a personal life. Whether your personal life is sketchy or not, I always believed in a personal life. You knew me in college and I had a personal life.

But I remember saying, I don’t know. Politics is too unforgiving but I was still very much into politics, and then I took economics. I took microeconomics and I will never forget just taking the course and saying to myself “hmm this is different. This is it. This is the ticket,” and what pissed me off the most, here I am considering myself fairly educated and at no point, at no time EVER had this conversation been had with me about economics and how money works and how it truly is the lifeline of our society. I remember growing up thinking it was politics. Political power. I had never even been introduced to what economic power meant.

I remember growing up thinking it was politics. Political power. I had never even been introduced to what economic power meant.

Sorry – let me just back up a bit. So, at no point while you were growing up, did anyone speak to you about savings, checking, etc?

Nope. Not at all. Fortunately, I don’t have money at that time, so I’m not blowing it. I’m still a broke student but I’m undergoing my enlightenment phase. At least my first level of enlightenment.  I’ve been introduced to a way that the world works, to a discipline that I had not known about, and my lightbulb goes off. The switch has been flipped. I don’t know how bright the light is at this point, but the switch has been flipped. So I rushed to take as many economic courses as I could. So here I am, I’m pressing to learn as much about economics as possible. I applied for a fellowship in public policy to get my Masters.  The way the fellowship works, if I win the fellowship, I then have to apply to certain schools that are participants of the fellowship. If I get into that school, then virtually my graduate degree is paid for. It’s two layers; I win the fellowship. Yes, thank God.  My graduate school is paid for, but I still gotta get accepted into one of the participating graduate schools. So to make a long story short, I’m doing my thing at HWS, you know, I was very a successful student there. I did win the fellowship and then ultimately I applied to grad school. Let me tell you this, Javi. It never dawned on me.  Now this is the psychology of a young man who was born and raised in public housing, but really doesn’t know his potential. When I applied for undergrad, I got accepted into every school I applied for. It never crossed my mind (at the time) to apply to an Ivy League school. I got accepted into every school I applied to. I’m matriculating into Hobart & William Smith, but it still never crossed my mind “Dude, why didn’t you apply to an Ivy League school?” because you can subconsciously limit yourself. Here I am, I’m about to go to college. That’s a huge success story. Here I am. Born in public housing, parents are addicts. But, I created my own ceiling.

.... you can subconsciously limit yourself

That’s a gem right there.

Here I am thinking I am blessed, and I still didn’t realize that my ceiling can actually be higher. I don’t even know this. So, that’s important. The reason why I say that is because when I applied to graduate school, I remember saying this to myself “you know I’m going to apply to the Ivy League schools and make them tell me, no”. The only thing the school can do is tell me no, so damn, I didn’t lose anything. I’m not going to tell me ‘no’. So now, I’m in the driver seat. I’m the one who is running this thing. To make a long story short, I got accepted into all the Ivy League schools. I chose Harvard, obviously. At this phase I’m telling myself, I’m not completely sold on this political thing because I’ve been rubbed the wrong way. This is before social media, so I believe career wise, I made the right move. I would have been tanked just by virtue of my dating life to be honest. I mean I’m sure someone would have popped up on twitter or Facebook and would have said “you dog” and they would have been right.

I chose Harvard, because I remember saying to myself, just in case, I’m not that sold on politics, at least I have the brand of Harvard. And the goal is, no matter what I want to do, at least when I got into the room, people will pay attention to me, because they’ll think I may know what I’m talking about. That’s the brand, Harvard gives you. I met a lot of stupid people there, but when you have that brand, you are at least allowed to participate in the conversation to prove that you are intelligent or to disappoint people, and let them learn that you are indeed stupid. But you are at least invited to the conversation. That’s the reason why I chose Harvard.

To make a long story short, while there, I focused on a lot business-oriented stuff even though my degree is in public policy. The track I took was Business & Government policy and Financial Management. I tried to focus this thing to learn as much as possible on business and finance.

And the goal is, no matter what I want to do, at least when I got into the room, people will pay attention to me, because they’ll think I may know what I’m talking about. That’s the brand, Harvard gives you.

Are you hooked? My favorite line from this part, "you can subconsciously limit yourself". Please check back in for Part 2, which I will be posting in a few days. Alternatively, you can subscribe to be notified immediately when it goes up. Are you feeling this series? Let me know either here or on my Facebook!


Image from Neon Brand