Today we’d like to introduce you to Dwight Dale
Hi Dwight, we’re thrilled to have a chance to learn your story today. So, before we get into specifics, maybe you can briefly walk us through how you got to where you are today?
I’m a 48 year old husband, and father of 4 girls. Entrepreneur & business owner, living in Orlando, Florida for over 30 years. Born in Queens, New York to Jamaican immigrant parents, I grew up in Jamaica Queens in the 80’s. I was raised in Urban, New York, which is a melting pot of cultures & ethnicities. Fully enriched in my family’s Jamaican culture, I was always surrounded by reggae music, delicious Caribbean food, and traveled to Jamaica frequently throughout my childhood. Raised in my mother’s Christian faith, but exposed to Rastafarian lifestyle & ideology from my father. Very close-knit family, I grew up in the same house as with cousins, as if we were siblings.
My family moved to Orlando, Florida in 1992, as I was halfway through Highschool. Quite the culture shock, but I acclimated quickly with my New York state of mind, and fast talking, hustle mentality. Had my first daughter at age 22, and spent many years in the work-force, to support my family, and eventually became a licensed health insurance agent. Remarried at 35, and had 3 more daughters with my current wife, and spent years climbing the corporate ladder, while simultaneously running side businesses, like Pest Control, Cutting Hair, or any other hustle I could think of to support my family.
Throughout these years, my cousin, who I was very close with, lived a very carefree Rastafarian lifestyle. Almost like a modern day hippie. College educated, with no children, I would follow him around fondly posting videos of him and his carefree lifestyle & flowing dreadlocks, in a joking manner, calling him an “Urban Rastaman”. Jokingly mocking Natural Geographic style posts about the “Urban Rastaman, in his natural habitat.” He hated it. he preferred his anonymity, but my followers LOVED it, demanding “MORE URBAN RASTAMAN”. We were onto something. But my cousin wouldn’t approve, Feeling I was mocking him, and wanted nothing to do with it. So I proceeded to create the Urban Rastaman concept, without him. He wasn’t THE Urban Rastaman, he was simply the inspiration.
Instead I looked inward, as we shared similar ideologies. But I was working in Corporate America. An insurance agent, family man, and a hustler, I had to figure out a way to invent the “Urban Rastaman” concept on my own. At first, I thought it to be the Corporate Rasta. The Lion in a suit, if you will. So that’s where I began. I created a logo of a lion in a suit, to represent my walk within the corporate structure. Holding on to my culture, while confined to the rules of the system. The Lion in Babylon! At the time, I had no idea what I was doing, but the idea of the “Urban Rastaman” remained prevalent in my mind, and they say if you cant stop thinking about something, then don’t stop working toward it.
All I had was a logo. So I figured the best way to get this idea out was to put it on a T-Shirt. But let’s be clear, I never wanted it to be a T-Shirt company. It was a brand. A movement. A Concept. A feeling. A lifestyle. The Lion in the suit represented Culture, Independence, and strength, in a world where those things were typically stripped away from you.
Meanwhile, my father was diagnosed with cancer. He lived with us, and I was the sole source of income in a household of 7. My wife, my 4 daughters, my father & myself. The unempathetic walls of my corporate position began to close on me, as I refused to go with the mundane flow of idiotic & illogical ideals, while dealing with a dying parent, and several other medical issues & life challenges in my household. My once respected role in Corporate America & the income I used to support my family was now in jeopardy, along with my mental health. Eventually too much pressure will break any man. Then on March 17th of 2018, daddy died, one week after my sister’s wedding (which he couldn’t make it to, though he wanted to, and I walked her down the Isle as he lay in a hospital bed.) and one week before his 69th birthday. I was distraught, and the 3 days allowed for bereavement wasn’t enough. My employer basically told me to suck it up, and get back to work (in not so many words). Eventually I snapped. I completely lost it. I was broken, and inconsolable. I realized the system didn’t give a damn about me, despite how much of myself I poured into building these organizations. I walked away from Corporate America, and vowed to NEVER work for anyone again for the rest of my life. Cashed out my 401K, and with no plan, I said I would survive off of my side hustles & my Urban Rastaman brand (which I still hadn’t figured out yet). This was April of 2019. I took my family to Jamaica, and I reconnected with my roots. Literally. I didn’t wear shoes for about a month. I let all my hair grow out. I denounced everything I thought I knew. Especially religion & politics. With the exception of my immediate family, I trusted no one and nothing. I stopped eating meat, and I got closer to my dad (who had recently passed). I started mediating, and studying my roots. The Urban Rastaman was born.
Eventually, my wife and daughters wanted to go “home”. It wasn’t fair to them that I was now on this journey to find myself, after they had been living so comfortably for so long. So we came back to Orlando, and moved into my family’s home with my mother, and spent the next few years rebuilding my new life as an independent entrepreneur. I used my insurance license, and everything I had learned through my years in Corporate America, and appointed myself directly with the insurance companies as an independent consultant. I started doing independent insurance work, along with my many side hustles, to pay the bills. I spent A LOT of time in the garden that my father had spent years developing, and found a new love for gardening, as it was a way for me to continue my father’s life works. Plus, I was growing & eating my own food, since I no longer consumed flesh. I soon realized that I truly had become an Urban Rastaman. Not realizing that the brand I had created, somewhat in Jest, with my cousin, was actually for myself all along.
Throughout this time I was still formulating what exactly the Urban Rastaman Brand was, and how it could actually generate revenue. I created a website, www.UrbanRastaman.com. I trademarked the brand, and the Pandemic hit!! Possibly the best thing ever, because I had already shut out the world. It was almost as if the entire pandemic occurred JUST FOR ME. I loved it. I used the time to create. I produced more t-shirts, and more designs, and I added to the products. The brand was whatever I wanted it to be. I sold Caribbean Flags, and T-shirts with the brand logo, and positive sayings. They sold on the website, and I used social media to build relationships, and build awareness of Urban Rastaman, the Brand, The Movement, The Lifestyle. Once the world began opening up, I would go out work events, selling my products, and building a name for myself in the community. Eventually I began hosting my own events in the community. Urban Rastaman became known for it’s independence, and unique style, with a strong emphasis on Rastafarian Culture, Love, Positivity, Authenticity, Natural Living & Lifestyle. Ultimately, I felt like Urban Rastaman saved my life. because in the midst of my darkest moments, it was resting in my culture & Rastafarian roots that kept me alive.
I turned Urban Rastaman into an LLC, and to this day, along with my independent insurance sales, Urban Rastaman has been growing into an entity that I could only have been placed in my heart by the Creator. Currently Urban Rastaman’s primary product is apparel, but we have a pop-up shop, and brand ambassadors, and we sell an array of products that I choose to sell. I’m finally earning more than I have ever made in Corporate America, independently, and I will NEVER work for anyone again, for the rest of my life. FUCK the system!!! I AM THE URBAN RASTAMAN!!!! I understand how to play the game, and I can play it well, but I choose not to. I spend time in my garden, I take my daughters to school & pick them up every day. Nothing is more important than my family. I do what I want, when I want. I pay my taxes, and I do whatever I need to do to maintain my freedom & independence. I give more than I take. and life is good.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
In the beginning, printing T-shirts was a challenge. Printing companies used screen-printing, which required me to spend large amounts of money ordering my printed shirts, and they all had minimums of 24 shirts, per design. This meant that I had to order large amounts, and just sit on the inventory, even though I hadn’t figured out how to fully market my products, or find customers yet. It was extremely frustrating. But the more I was faced with obstacles, the more I learned to do things myself, and not rely on other people, or other companies. I learned how to print the shirts myself, in my garage, during the pandemic. I started getting t-shirts directly from the manufacturers, and cut out the middle man. Eventually, I was able to print on demand, thanks to some of the relationships I built in the community, and learning the right things from the right people. My resilience pushed me through every obstacle I faced, and I’m and excellent student of Google & YouTube university. Then once Artificial intelligence became so advanced, and I had access to tools like ChatGPT, there really wasn’t anything I couldn’t figure out.
Thanks – so what else should our readers know about your work and what you’re currently focused on?
I run a small business, which is similar to being an entrepreneur. My business, Urban Rastaman, is a brand, not just a store. It sells a variety of things, like apparel, flags, jewelry, books, dominoes, and small accessories. We also host events that promote Caribbean culture, positive vibes, and reggae music. Our brand slogan is “Spread Culture.” Urban Rastaman is a movement, not just a business.
We have an online store and a strong social media presence, and we enjoy sponsoring events such as night markets, drum circles, open mics, pop-up shops, and pretty much anything that makes sense and fits in with the brand.
I am also an independent insurance agent, and my office is in Altamonte Springs. We have two business partners and mostly sell health insurance but we also offer Medicare. The Medicare education we provide helps us bring in business. I also own a small pest control company that started as a side hustle but now has a business partner who manages it.
Have you learned any interesting or important lessons due to the Covid-19 Crisis?
It is paramount to trust your instincts and recognize that the structure of the establishment was designed to benefit itself. Thus, it is best to fully understand how the system works because at the core, all systems are identical. This insight will help you determine if you want to participate in the established order, or if you want to abstain from playing the game. I choose to play the system, but only as necessary for the purpose of feeding my family, and maintaining my independence. I have learned to make my peace of mind and my mental health my highest priorities, and I have developed a firm faith in my abilities, my culture, and my connection with my higher self and God. I have also realized that all the rules are, at the end of the day, just suggestions. And everything has consequences, either positive or negative. My biggest takeaway is the balance of life, and how I must give more than I take. I have learned that every event that takes place in this life has a specific purpose and is happening for my benefit, not against me. The experiences I’ve been through have taught me that I am the Urban Rastaman. This may seem obvious now, but I didn’t know this for a long time. I have also learned to trust the process, and I have learned that, when it comes to overcoming pain, I can’t run from it, I have to sit with it. And last but not least, I’ve learned that, contrary to popular belief, I am human. And that’s okay.
Contact Info:
- Website: https://www.urbanrastaman.com/
- Instagram: https://www.instagram.com/urbanrastaman/
- Facebook: https://www.facebook.com/TheUrbanRastaman
- Youtube: https://www.youtube.com/@urbanrastaman.frequency
