How Real Estate Wholesaling Transformed Derek's Life

How Real Estate Wholesaling Transformed Derek's Life

3 min max read

Wholesale real estate, a niche yet highly lucrative area of the industry, offers unique opportunities for growth and significant income. Among those who have successfully navigated this field, Derek serves as a prime example.

Over the past eight years, he has completed an impressive 500 deals, generating substantial income, such as a staggering $72,000 from just a single transaction. His journey in wholesaling is not just a story of financial gain but of persistent adaptability and innovative strategies, driven by his lifestyle as the spouse of an active-duty military member.

The Path to Wholesaling Mastery

Derek’s entry into real estate wholesaling began out of necessity and curiosity. In 2016, he transitioned from owning and operating an MMA gym to dabbling in real estate, propelled by frequent relocations due to his wife's military career. His initiation into wholesaling was somewhat serendipitous but marked by a steep learning curve. Derek recalls, “I used to make offers on FSBOs (For Sale By Owner) with no intent to buy anything because reps and talk to people.”

His unconventional start via platforms like Craigslist and his trial-and-error approach gradually morphed into a more refined, systematic operation. Derek leveraged his circumstances—constantly moving due to military relocations—to shape a business model that was virtually resistant to geographical constraints. He focused his efforts on Louisville, Kentucky, his hometown, fully utilizing his in-depth knowledge of the area to score deals consistently.

"Got a deal from Craigslist. Fumbled through it pretty brutally as far as not knowing what I was doing. Made like eight grand, and I was like, I can't believe this works." - Derek

Profiting from Persistence and Systems

The success of a wholesaler hinges on reliable systems and persistence, principles that Derek underscores through his practice. As he gained familiarity with the real estate terrain, he began incorporating advanced tools such as driving for dollars, pulling lists, and skip tracing. These techniques allowed him to transform his initial haphazard attempts into a repeatable, scalable business.

Throughout his journey, Derek maintained a focus on Louisville regardless of his physical location, a strategy that has paid dividends. Despite the constant upheavals in his personal life, his business thrived as he perfected the art of remote deal-making. Derek’s approach underscores an essential wholesaling truth: understanding your market can significantly tilt the scales in your favor, even if you are not physically present.

Adapting to Market Changes and Leveraging Technology

In an industry as dynamic as real estate, adaptability is crucial. Over the years, Derek witnessed shifts in market dynamics and consumer behavior, necessitating adjustments in his strategy. Initially reliant on platforms like Craigslist and Facebook Marketplace for leads, his focus shifted towards more robust and scalable marketing methods.

Today, Derek employs a mix of outbound marketing, including ringless voicemails, cold calling, and texting—tactics that enable immediate communication with potential sellers. His marketing arsenal is designed to generate quick responses, allowing him to gauge seller motivation and act swiftly.

Additionally, technological advancements have streamlined processes significantly. Derek mentions how innovations in skip tracing technology have reduced his operational costs while maintaining lead quality, a critical factor in sustaining profitability.

The Real Impact of Wholesaling

Beyond the impressive numbers and entrepreneurial success, Derek’s story is fundamentally about leveraging real estate wholesaling to achieve personal freedom and support his family's unique needs. His ability to operate a thriving business amidst frequent relocations and family commitments stands as a testament to the flexible, empowering nature of real estate wholesaling.


Derek’s wholesale journey illuminates the potential within the real estate sector to create not just wealth but an adaptable, resilient lifestyle. His strategies and insights offer a valuable guide for anyone looking to enter the wholesaling space or refine their approach. With the right mindset, understanding of market nuances, and effective use of technology, success is not just possible but probable.

For real estate professionals, Derek’s narrative offers more than just strategies—it inspires a vision of what can be achieved with determination, adaptability, and a keen understanding of one’s market. Whether you are a seasoned investor or a newcomer, the principles of dedication, systematization, and market knowledge stand as universal pillars for success in the ever-evolving realm of real estate wholesaling.

Samantha Ankney

About Samantha Ankney

Samantha has been a media specialist for DealMachine for 2.5 years. She produces, edits, writes, and publishes all media that is distributed to the DealMachine and Real Estate Investing community.