My Journey as a Homeless Entrepreneur

A story about perseverance.

I’ve battled homelessness several times throughout my life, but the most recent time happened soon after I was readmitted to the University of Virginia. When I first transferred to UVa in 2012, I was working part-time on weekends as a waitress. It was about an hour drive for me to get to work. Despite the long drive, the tips were good-especially on weekends and it was just enough for me to afford my one-bedroom apartment in Charlottesville.

By the time classes came around, I was hopeful that I'd be able to continue working my shifts at the restaurant and keep up with my studies. What no one tells you about transferring from community college to a four-year school? That shit is hard, man! My grades quickly began to drop as financial pressures increased. I faced academic probation and started giving away my shifts at work to make up coursework. Eventually, I got fired from my waitressing job. You can only give away so many shifts before managers start to notice. I was broke, hungry and failing multiple classes. As money became tighter, I found myself behind on rent, not eating, and I was...depressed. Like depressed-depressed. I suppose this could count as one of many rock-bottoms. I've experienced several throughout my life. Unfortunately, it got much worse before it got better.

It was at this time that I started a blog, and generated some revenue from various online gigs. More on that another time. I was still broke, but at least now I had a creative outlet and some relatively consistent cash flow. Rent was still late on occasion, but I had food in my fridge and the flexible hours from my online gig allowed me to finish the school year in better standing.

After my disastrous semester at UVa, I decided to take a break to sort my life out.

Fast forward to Spring 2012. I was working as a barista/bartender and had just started advertising for what would eventually become my small business, Luxie Hair Services. I decided to put school on hold as I grew my business. Cash flow began to pick up and I was excited to see the fruits of my labor paying off. However, as a young entrepreneur in a cash-based business, you know what I didn't have? Financial literacy. I was spending money just as fast as I could make it. Ya girl was still broke-broke.

After a strange turn of events, I found myself in southern Virginia. My plan was to grow my hair braiding business in the North Carolina tristate area. Long story short–that shit didn't work. I had a hard time finding clients and my shitty 2000 Jetta couldn't keep up with the long drive. I used to make the 2.5 hr trip to Charlottesville almost every weekend to take appointments with clients. I was still pretty broke, but all of my hustling was starting to pay off as word started to travel about my mobile hair braiding services. I began to see a steady stream of clients in Charlottesville and decided to move where the demand was. When I moved back to Charlottesville, I didn't really have a place to stay lined up. I put my belongings in a storage unit and slept on friends' couches, made palettes on the floor with blankets, and sometimes slept in my car as I saved up for a place to stay. It was at this time that I decided to reapply to UVa.

When I found out I was readmitted, my excitement was met with uncertainty. I was worried about how I was going to pay for classes. I worried about whether or not I'd be able to work on my business while finishing school. I worried about being an older, unconventional student. I didn't want to make the same mistakes I made the first time. Despite all of the uncertainty, I felt this push to finish what I had started. I just kind of leaped and trusted that things would work out. I had a hard time getting loans to cover tuition, so I made the decision to sleep out of my car and use the money that I had to pay my tuition out-of-pocket. What most people don't realize is that the bill for school just kind of shows up on your account–almost like magic. It's like, "Hey, I see you added classes...Surprise! Here's your bill!" It's then up to you to figure that shit out before it's due. I had no idea how I was going to do it.

I slept out of my car for months as a full-time student while working part-time with my business. I would study and do homework late in the 24 hr library during the week, sometimes sleeping there, and when they closed on the weekends, I’d post up at coffee shops to get the rest of my work done. I worked Friday nights and 8-10 hour days on Saturday and Sunday. I sometimes had to write papers in my car after finishing clients if the libraries and coffee shops were closed.

As much as I tried to hide my situation, people started to notice that something was wrong and one of my clients who happened to work at UVa connected me to Dr. Mason. I’m so grateful to the staff at UVa who stepped in to help. I still get emotional thinking about it. When I reached out to Dr. Mason, I just wanted someone to talk to. I wasn't expecting actual, real-life help! After I told him about my living situation, Dr. Mason quickly reached out to financial aid and housing to get me the assistance I needed. I couldn't believe it. It’s crazy to think that this was only 3 years ago. So much has happened between now and then! I’ve started multiple businesses (Luxie Hair Services and Destinee Marketing, LLC). I've also had the privilege of hosting various local shows, I've spoken at talks, had an art exhibit for my Solidarity Cards Project and shared my story in different classrooms at Uva. Life is funny! 😅

Being vulnerable is hard, but I’m so grateful to the people around me who were supportive and continue to encourage me to continue to share my story. I was nervous when this story aired. I’m a Scorpio, I like to be mysterious 😆, but I hope that this story helps someone in a similar situation. I hope that it shows that you’re never defined by your circumstances.

If you or someone you know is battling homelessness in the Charlottesville area, contact:

The Haven Day Shelter: 434-973-1234
PACEM: 434-9731234
Shelter for Help in Emergency: 434·293·8509 or
Salvation Army Emergency Shelter: (434) 295-4058

Sending love,
Destinee

#CvilleBlackBiz post featured in Charlottesville Tomorrow!

Credit: Ézé Amos/Charlotesville Tomorrow

Credit: Ézé Amos/Charlotesville Tomorrow

I started this the #CvilleBlackBiz post on Small Business Saturday after a Facebook friend made a comment about the lack of support for local Black-owned businesses. I realized that there was no place for folks to reference the dynamic and growing number of Black-owned small businesses in the area, so I created a Facebook post inviting my Facebook friends to tag local Black-owned businesses in the comments. I was shocked to see how many people began to tag, share, like and comment! I realized that we were amassing quite the number of businesses, and decided to create a space online for folks to reference these businesses! I created a blog post that lists over 60 Black-owned local businesses! Recently, Charlottesville tomorrow interviewed me about the directory!

After a conversation with a friend about supporting small black-owned businesses in the area, Wright began to post about the ones she knew of and then researched more. Her post circulated on social media, garnering more than 1,000 views. 

To learn more about the #CvilleBlackBiz directory check out this article from Charlottesville Tomorrow!

It’s exciting to see this post garner more attention! I hope to continue to grow this list and create a space for Black entrepreneurs to grow and be supported. Click here to see the original post.

If you’d like to add an existing #CvilleBlackBiz to the directory, please email me directly at admin@hellodestineewright.com