We were lucky to catch up with Troy Reaves recently and have shared our conversation below.
Hi Troy, thanks for joining us today. Risk taking is something we’re really interested in and we’d love to hear the story of a risk you’ve taken.
I really appreciate the grind and effort I’ve been able to put into this. I took a huge risk this year and it showed me that this lifestyle of entrepreneur is worth the risk. At first, I only had two businesses just last year (DJPrettyBoyTroy Entertainment Services), and a Organic juice brand titled “Juice by DJPrettyBoyTroy”. The good thing about me is that I never stop thinking, so when I experienced a short layoff, I quickly unveiled three new businesses that hit the scene. Now I had started up a lawn care business, shoe cleaning business and finally opening a vintage sporting good store all throughout the summer of 2023. I had realized that I was taking this risk, I was actually at a Casino gambling (betting on myself) to achieve that financial freedom we all search for living the American Dream. These multiple businesses kept me busy over the summer due to the fact that I was going to fall behind on bills for the time being. Due to my undivided commitment with this, everyday I worked and worked until I started see doors open my way. I was fortunate to work nonstop to have my bills and rent paid. Taking this risk helped me see and visualize my dream and also to never stop and always keep going. Now with five businesses, I know its a season for everything if you are a entrepreneur and like to see your money flow up stream!

Awesome – so before we get into the rest of our questions, can you briefly introduce yourself to our readers.
Well my name is Troy Reaves and I am from Cleveland, Ohio. I am the youngest out of two. I attended Wilberforce University, graduating class of 2016 with a Bachelors Degree in Communications. From the start, my mother had instilled in me the mindset of an entrepreneur. I was around Ten or Evelen years old by myself selling candy on the public transportation bus. I knew I was good at running a business but without the experience, I knew I would be lost without a clue. I am most proud of my journey because during the worst times, I kept fighting through. One thing I am most proud of is my detail to providing exceptional customer service, I always go above and beyond to make sure my customers are satisfied with delight. I am a jack of all trades, I love learning about ways on making money each and everyday.

Can you tell us about what’s worked well for you in terms of growing your clientele?
I know this might sound repetitive, however, its important to post content each and every day. Use those hashtags in every post that you create. Don’t be ashamed if you don’t see progress right away, just remember your core audience is just a click away.

What else should we know about how you took your side hustle and scaled it up into what it is today?
I would say yes, my company “DJPrettyBoyTroy Entertainment Services” has become my full time business career. I can say I’ve been at this for 13 years. I have built a brand from the ground up, learning and implementing the tools that make me stand to those who are in the same industry as me.

Contact Info:
- Instagram: @DJPrettyBoyTroy
- Youtube: djprettyboytroy
Image Credits
Troy Reaves

