Today we’d like to introduce you to Sherita Roberts.
Hi sherita, so excited to have you with us today. What can you tell us about your story?
Meet Sherita Roberts, a Washington, DC native whose journey is a powerful testament to resilience, financial acumen, and the unwavering pursuit of freedom, both financial and personal. A proud graduate of Howard University, Sherita’s story inspires those who want to build multiple streams of income and live life on their own terms, not tied to the traditional 9-to-5 until retirement.
From an early age, Sherita was passionate about building wealth and finding smarter ways to earn. The idea of working until 65 never aligned with her vision. At just 24, she took a bold step and purchased her first home. Then went on to purchase three more properties that same year, diving headfirst into the world of real estate.
For over a decade, Sherita served as a landlord, navigating the ups and downs of the industry. The 2008 market crash hit hard, leaving her upside down on all her properties. She ultimately made the difficult decision to short sell them; an experience that felt like failure at the time, but gave her the knowledge and grit that would serve her later success.
In 2018, she re-entered the real estate game with a new mindset. She purchased a home in DC with the intention of generating income, and turned the basement into a thriving Airbnb, earning Super Host status. She added a rental property in Baltimore and, in 2023, expanded again by purchasing a 4-unit multi-family property, solidifying her place as a strategic and focused investor.
Along the way, she paid off over $100,000 in debt, dramatically increased her net worth, and proved what’s possible with discipline and intention.
And the biggest milestone yet? On March 14, 2025, Sherita officially quit her full-time job and became a full-time investor. A dream she turned into reality through years of planning, sacrifice, and smart money moves.
Now, she’s on a mission to help others do the same. She created a financial workbook called, Claim Your Freedom, which is designed to help people get out of debt, build wealth, and take control of their financial futures.
Sherita Roberts isn’t just a success story, she’s a real-life example of what’s possible when you commit to the journey. She’s here to show others that with the right mindset, strategy, and action, financial freedom is within reach.
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?
Absolutely not… things did not go as planned. My original goal was to buy 10 houses, refinance them all, and pull $100K from each one to hit millionaire status. That was the dream. But what no one told me was that some tenants will sign a lease with zero intention of ever paying rent. And don’t get me started on the 2008 market crash, there was no preparing for that. I ended up upside down in every single property and had no choice but to pivot. On top of that, being a landlord came with a whole set of challenges I hadn’t fully anticipated, constant repairs, unexpected expenses, evictions… it was a lot.
Appreciate you sharing that. What should we know about Homestead365 property management group?
For 19 years, I worked for the federal government in various roles; everything from budget execution to auditing and contract acquisition. While I gained invaluable experience, I knew I wanted more freedom and purpose. So in March 2025, I took a leap of faith and walked away from my 9–5 to become a full-time entrepreneur.
Today, I provide affordable housing to low-income residents, helping families secure safe, stable homes. I also launched a financial education platform called Debt Free Destiny, where I teach people how to become financially literate, break free from debt, and build the life they deserve. It’s all about helping others claim their freedom….just like I did.
Any advice for finding a mentor or networking in general?
Absolutely! Finding the right mentor and building a strong network can be game-changing—especially in real estate, entrepreneurship, and personal finance.
Tapping into existing communities: I got serious about showing up in spaces where like-minded people were—local real estate meetups, online courses, social media masterminds.
Being honest about where I was: I didn’t pretend to have it all together. I was transparent about my goals, challenges, and desire to learn and that’s what drew people in.
Creating my own platform: Sometimes your network grows when you step up and become the one sharing knowledge. Debt Free Destiny has connected me with people I now consider mentors, peers, and lifelong friends.
Contact Info:
- Instagram: https://www.instagram.com/debt_freedestiny
- Facebook: Debt free destiny
- Youtube: https://youtube.com/@sheritaville
