We caught up with the brilliant and insightful Mychal Greenwood a few weeks ago and have shared our conversation below.
Alright, Mychal thanks for taking the time to share your stories and insights with us today. Coming up with the idea is so exciting, but then comes the hard part – executing. Too often the media ignores the execution part and goes from idea to success, skipping over the nitty, gritty details of executing in the early days. We think that’s a disservice both to the entrepreneurs who built something amazing as well as the public who isn’t getting a realistic picture of what it takes to succeed. So, we’d really appreciate if you could open up about your execution story – how did you go from idea to execution?
Well, it’s funny I’ve worked with kids my entire life. As a high school student, I worked at a basketball camp, with elementary and middle school age kids. From there as a young adult in college I worked several years at a before and after school program in the suburbs of Cleveland, Ohio this was during a time that we now refer to as the recession. As a young parent trying to provide for my family I decided to leave the Midwest and head south to Tennessee. Upon arrival I was just looking for work and so I turn to the quick fix of applying and doing factory work. This paid the bills, however it did not make me happy and I felt there was a void. Around the same time my nephew approached me about coaching him and his friends in basketball. These interactions with these young men helped me to feel a void, but also provided a spark. As I spent more time with these gentlemen, who were all early in their teenage years, we began to have more conversations about life and manhood. Through these conversations is when I start to get the notion of doing this on a full-time basis. I tried applying to organizations like big brother, big sisters and boys and girls club unfortunately or should I say fortunately, those situations didn’t work out. My next thought was maybe I should go back to school to get my teaching degree, but trying to work full-time and get my degree simultaneously were two things that I didn’t do well at juggling. so, that led me to the idea of what if I could start my own organization why, not as this idea was tossed around in my head, I spent more and more time with these young men who I affectionately called my nephews, and they now refer to me as “Unk” so to crank things up a notch, I decided with the help of my brother to organize a college field trip to Northern Kentucky University. The young men were excited. I on the other hand was super nervous. After all, I’d never been on a college tour myself. That aside with very little money out of our own pockets, my brother and I packed the boys in my car and his SUV, and drove them up to NKU‘s campus. To my surprise and relief, the boys loved it from that moment forward I knew what I wanted to do. The next steps was to do the research on how in the world do you start a organization like this, and what exactly is a nonprofit as I was researching reading books, asking questions, I continued to create activities and events for the young men and myself to get involved in. Although these activities were enjoyable and fulfilling for me, as well as educational and enjoyable for them, they were taking a toll on me financially, and putting a strain on my family life. So next I had to figure out, how can I do this as a career and not lose my job before then. A few years later I had the “mis”fortune of having to have knee surgery. While recovering from knee surgery, I received unemployment and decided to enroll in barber school. My plan was to obtain my barbers license. Being self-employed would provide me with financial stability and a flexible schedule to be able to do field trips in the future. I’ll never forget, wanting to take a group of young men and ladies to Atlanta to visit Spelman Morehouse and Clark Atlanta‘s campus and having to lie to my boss that I was sick, so I could take this trip. It left me with a terrible feeling having to lie to someone and hide something I otherwise felt so excited about. This also led me to the thought process of no longer wanting to work for someone else. With finances still at a minimum my first thought was I to come up with ways to lessen my expenses on things I did with the guys. I didn’t like going to their parents for money anymore than I had to because at the end of the day I knew that they were struggling and I feared a response of them removing their son from the program. So in order to lessen the expenses, I decided to pursue the local schools and recreation centers that me and the boys all resided in. Unfortunately, this was not met with open arms and so I had to go to Plan B. Plan B was to see if what I had to offer would be excepted in the bigger inner city of Nashville Tennessee, however, the biggest hurdle in doing this was I didn’t live in Nashville, I wasn’t from Nashville and had no connections to anyone in Nashville. So I literally had to start from Ground Zero. Through the help of social media, I would learn about community meetings going on throughout the city. I’d go to these community meetings, take notes and network, introducing myself, and my program, to anyone who would listen. One of those people happened to be a school superintendent. This gentleman gave me some phone numbers and names to contact that would help me get into the schools. Neither of these people got me into the schools, lol. However, they did invite me to a meeting which several other school administrators attended. There I met a young administrator name Brent Dean who had a matching desire to educate and provide opportunity for our youth. He took a chance by giving me a shot and six years later we’re still proud partners of Metro Nashville Public Schools.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?
I’m originally from Cleveland Ohio second oldest of five, husband and father of five… grandfather of four. I am the founder of Humble Beginnings & Humble Beginnings Academy I honestly always had a passion of working with kids, but one of the biggest motivating factors is I was just wanting to create a better community and environment for my children. Growing up going through some hard times financially watching my mom struggled which limited opportunities for me. I remember being in middle school working as a janitor over the summer in that middle school, while the rest of my friends participated in a basketball camp. The same camp I later worked at. I wasn’t able to be a participant because our family didn’t have the resources and that type of upbringing is a big motivating factor for why and how I do what I do. What we do is simply try to provide young people with opportunities. Now we’re not equipped with billions of dollars so the opportunity that we provide is education we feel like education is the best thing to change an individual’s circumstances. One of the things that we do that’s different is that although most of our interactions are in group settings, we make sure to individualize our interactions with our scholars as much as possible we have a base format that we follow. However, people are not all the same so we cannot approach, deal with, nurture or educate as if everyone is the same. People are dealing with different traumas, obstacles and hurdles and so we have to, best we can, meet them on that level. We don’t just look for students who are straight A students, athletes or students who all have a history of getting into trouble. We like to meet with a variety of students and put them together because what we’ve found is they all learn from each other and lean on each other when given the space and opportunity. One of the things we are most proud of is the fact that when you are a part of our program, it is as long as you want to be a part of our program. There is no end date that once you get to this grade or that grade or this age with that age that you are now out of the program life goes on you go to college, you get older and you still need guidance or just someone to have a conversation with. Someone to help you hold yourself accountable to certain goals and obstacles that life will present to us all. So with that being said, the proudest thing is to see some of our earliest members still come back and call about of how to be a father, marriage advice, career choices. And it’s not just calling with problems. We get to celebrate you know, the birth of children, promotions, and things of that nature. I have a lot of the young men that I started with who call and give back either with time or monetarily. For example, one of our earlier members Parrish Gaines, who went on to serve in the United States Navy, and also play football for the Naval Academy, started the Create Your Own Path Scholarship foundation. Which Humble Beginnings has partnered the last two years and honored to give small scholarships to individuals who graduate high school. Some of my “nephews” are now team members and coaches. That type of connection, bond and commitment is one of the things that set us apart. I believe we’re able to create that because we ask our team members to be 100% themselves and program members to be themselves, which creates a space for authenticity and growth.

Have any books or other resources had a big impact on you?
Early on in my starting a nonprofit program, I reached out to my best friend’s uncle; he had experience of starting, and operating a successful nonprofit program. Dealing with youth called target excellence in Sacramento, California. He’s giving me great advice in guidance, and in the process of that suggested I read a book called “The E-Myth Revisited” by Michael E. Gerber. This book was great because it helped me mentally transition from being an employee to being self-employed to being someone who runs an organization with employees and volunteers on his team.
What’s a lesson you had to unlearn and what’s the backstory?
The biggest lesson I had to unlearn was the thought process that I didn’t belong in certain rooms without certain credentials, certain backgrounds, certain friends, and family members that your jazz grow up with you can’t believe it’s easy to believe your idea your philosophy your perspective is not as great as those with Larger titles so the biggest lesson I had to unlearn was that we are all human and just because they got certain credentials does not mean that they have all the answers my life experiences, my vision, my blessings from God are my credentials, and that validates my perspective
Contact Info:
- Website: https://www.humblelegends.org/
- Instagram: https://www.instagram.com/_humblelegends/
- Facebook: https://www.facebook.com/HumbleBeginningsTenn

