Debbie DeBerry – How The Flipstress Found Her Calling in Real Estate
By Space Coast Daily // April 8, 2024

Debbie DeBerry is a well-known real estate coach, who is also known as “The Flipstress.”. While the nickname might seem unusual initially, it describes precisely what she does: using proven methods to successfully flip houses in markets across the United States.
Though DeBerry’s journey to becoming The Flipstress and building her real estate investing business into a multi-million dollar company was challenging, she succeeded by focusing on serving others and emphasizing quality and safety in the homes she recreates.
Now, as a leader in the real estate industry, DeBerry encourages women worldwide to take the same risks she did, challenging traditional norms and achieving success. Her story goes beyond being an entrepreneur; it shows the fundamental importance of women in the market and serves as a hopeful example for future equality.
The Early Years
DeBerry experienced some challenges at a young age. Her family moved often during her early school years, which made her feel distant from many of her classmates, always being “the new kid.”. Even though she tried her best to blend in, DeBerry faced severe emotional and physical bullying when she started middle school. Eventually, it became so bad that she had to leave the school.
The Flipstress says she was a perfectionist and was tough on herself early on. This eventually led to her developing an eating disorder in her early twenties. She explains that this experience made her deeply reflect on the harmful messages society sends to women. She realized that women are often expected to be perfect, handle everything independently, never show weakness, and prioritize everyone else’s needs over their own.
DeBerry understood how harmful these societal expectations were for herself and many other women.
DeBerry’s Journey in Real Estate
DeBerry’s journey into entrepreneurship began soon after she graduated from the University of Texas with a Master’s degree. She took on the management of three yogurt franchises, describing the experience as a crash course in business and management. It demanded long hours and offered little time, freedom, or control.
DeBerry found comfort in her mother, her biggest supporter and cheerleader. DeBerry recalls, “She always told me I could achieve whatever I could dream. She pushed me to do challenging things and was there for me when I made mistakes or things didn’t go as planned. She let me be upset for a while, but then she encouraged me to return and try again.”
DeBerry’s mother inspired her to explore real estate, prompting DeBerry to get her license in 2003. In the initial years, she followed the traditional path in real estate, building a respected business by working with home buyers and sellers as a real estate investor.
DeBerry grew weary of the hustle culture in the real estate industry. She felt drained by the challenges of the housing market, constantly chasing buyers, dealing with no-shows, and being on call seemingly all the time. These aspects took away from her enjoyment of her career. DeBerry realized she could achieve a lot more by taking a new direction.
How House Flipping Changed DeBerry’s Prowess
In 2008, DeBerry followed her intuition and ignored the doubters as she flipped her first house. This bold move may have earned her the nickname “The Flipstress.” It was during this venture that she first recognized her creative abilities.
DeBerry also discovered the financial potential of this business. A significant profit from her first flip was enough to get her hooked, especially with the positive reactions and support from her associates, friends, and family. In her first year of flipping homes, she tripled her income.
Following that success, she launched her career as a professional house flipper, climbing the ranks and earning respect among fellow agents and investors. She specialized in using data-driven methods and techniques to make informed decisions rather than relying solely on intuition. DeBerry emphasized prioritizing facts over gut feelings when assessing the housing market. In addition, she was one of the first house flippers in her local market to place an emphasis on creating a high quality and design-forward home, versus the usual flipper mentality of putting in whatever material is cheapest.
DeBerry Embraces the Idea of Empowering Women
The Flipstress faced a significant setback in her career when her mother passed away in 2014. DeBerry struggled with the loss, affecting both her personal and professional life. This led her to look deeply at herself and her goals, resulting in a period of soul-searching to find renewed purpose and direction as she coped with the pain.
This period of self-reflection led DeBerry to a significant realization. Despite her success in helping buyers and sellers, she felt she wasn’t making enough of an impact on the lives around her. DeBerry found that her true passion lay in empowering women like herself. This realization marked the first step toward her journey as a coach.
DeBerry understood that many women faced similar challenges and lacked the necessary tools and support to break out of their comfort zones in their professional lives. Drawing from her own experiences, including her childhood, early years in real estate, and the loss of her mother, who was her source of inspiration, she resolved to develop a structured program that addressed everything other real estate investing programs lack: affordability, community, and a focus on truly serving others. This program aimed to teach women how to flip houses and their lives.
The Flipstress Coaching Program Gives Women the Resources to Excel
Debbie DeBerry is paying forward to others what her mother gave her—a cheerleader, a fan, a safety net, and empowerment Through her professional real estate coaching business, the Flipstress goes beyond simply guiding first-time house flippers through transactions; she encourages women to see investing as a pathway to time and financial freedom.. DeBerry’s goal is to assist women in building a lasting legacy that they can be proud of passing on to their kids and grandkids
DeBerry brings her people-first approach to the real estate industry, recognizing the challenges that often prevent women from getting started in this business.. Her understanding of overcoming these obstacles has made her a significant influence in the field. DeBerry believes that anyone can achieve what she has accomplished by ignoring anyone who isn’t doing the thing you want to be doing in the way you want to be doing it.
The Flipstress’ FlipSisters Coaching Program & Community has become the #1 program for empowering women to flip houses confidently. In DeBerry’s view, as well as that of many other women who have achieved remarkable success through her guidance, it represents the most effective method for achieving your real estate investing goals and dreams.











