Military Spouse Builds Thriving Real Estate Empire While Moving Every Year

Military Spouse Builds Thriving Real Estate Empire While Moving Every Year

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Building a real estate empire is often viewed as a process that requires stability, financial resources, and years of experience in a single market. But Derek, a former MMA gym owner and military spouse, has proven otherwise.

Over the past eight years, while supporting his wife through eight relocations in ten years, Derek has built a virtual wholesaling business that has completed nearly 500 wholesale real estate deals. His success shows that even in a transient lifestyle, real estate wholesaling can create both financial freedom and flexibility.

His story is not just about profit. It’s about building a sustainable real estate empire that can grow regardless of where life takes you.

From Humble Beginnings to Real Estate Success

Derek’s first exposure to wholesaling came in 2016 when he stumbled upon a property on Craigslist. With no real estate experience, he put it under contract and made $8,000 on his very first deal.

He admits he “fumbled through it pretty brutally,” but that experience changed his life. If a beginner could earn five figures from one deal, he realized the potential of scaling it into a business.

At the time, Derek had sold his MMA gym on seller financing and needed a new source of income that could survive frequent military relocations. While he initially wanted to flip houses, he quickly discovered that wholesaling was a better fit for a mobile lifestyle.

"We’ve moved eight times in the last 10 years. I move again in another 12 months." – Derek

The Power of Focusing on One Market

What sets Derek apart is his decision to focus exclusively on his hometown market of Louisville, Kentucky. Rather than starting over each time he relocated, he built deep expertise in one market and operated virtually from anywhere in the country.

His knowledge of Louisville became so strong that he once agreed to purchase a property knowing only the zip code and price. That level of confidence stemmed from years of experience and established relationships within the same market.

This focus gave him a competitive edge. While other investors spread themselves thin trying to learn multiple markets, Derek doubled down on one. That’s how he built the foundation of his real estate empire.

Building a Virtual Wholesaling Machine

Derek’s business model evolved over time. Initially, he browsed through free listing sites, including Craigslist and Facebook Marketplace. But those strategies only produced a handful of deals each year.

To build something scalable, he shifted into systematic marketing. His team now relies on:

  • Ringless voicemails sent to targeted lists
  • Text messaging campaigns to reach motivated sellers
  • Cold calling absentee owners and vacant property lists
  • Partnerships with local boots on the ground to handle property visits and buyer relations

This structure enables Derek to focus on acquisitions and marketing remotely, while his local partner handles in-person tasks. Together, they’ve created a machine that runs smoothly, regardless of where Derek and his family are stationed.

The Financial Reality of Wholesaling

Derek’s results showcase both the highs and lows of wholesaling:

  • Average assignment fee: $11,000–$13,000
  • Lowest assignment fee: $20 (from a deal that fell apart at the closing table)
  • Highest fee: $72,000 (from a multi-family property)
  • Total deals completed: Nearly 500 in eight years

With millions in assignment revenue generated, Derek’s business has supported his family while providing him with the freedom to relocate as needed.

Importantly, Derek emphasizes that wholesaling isn’t always about giant paydays. The real strength comes from consistent income through volume. Even when a deal falls through, persistence ensures that the next one could be life-changing.

Lessons from Derek’s Real Estate Empire

For investors dreaming of building their own real estate empire, Derek offers key insights:

1. Focus on One Market You Know Well

Instead of constantly starting fresh, stick with a market where you have a solid understanding of property values, neighborhoods, and buyer behavior. Derek’s loyalty to Louisville gave him the consistency to scale.

2. Partner with Locals if You’re Remote

Having reliable boots on the ground is critical. Derek relied on local partners to check properties, meet sellers, and handle buyer dispositions while he worked virtually.

3. Build Scalable Marketing Systems

Free lead sources like Craigslist may work for beginners, but they won’t sustain a business. Derek’s transition to ringless voicemails, texts, and cold calling created predictable deal flow.

4. Don’t Dismiss Small Deals

Even with 500 deals under his belt, Derek has had transactions that netted almost nothing. Instead of getting discouraged, he stayed focused on the bigger picture. Every deal, big or small, was a step toward building his empire.

From Wholesaling to Teaching Others

Today, Derek shares his experience with aspiring investors, especially military spouses and stay-at-home parents who need flexible income. Through his YouTube channel, The Real Real Estate Dad, he teaches how wholesaling can be a part-time business that changes lives.

He believes even modest success is worth pursuing:

“Even doing one deal a month will change someone’s life.” – Derek

His message is simple: you don’t need perfect circumstances to build a real estate empire. You just need persistence, systems, and the right mindset.

Why Derek’s Story Matters

Derek’s journey proves that building a real estate empire isn’t about being in the perfect city, having endless money, or working 80 hours a week. It’s about creating systems that work for your lifestyle.

For military families, stay-at-home parents, or anyone with an unpredictable schedule, real estate wholesaling provides both income and flexibility.

With nearly 500 deals, Derek has demonstrated that you can relocate every year and still build a thriving business. His story is proof that a real estate empire can be built even in the most challenging circumstances.

Frequently Asked Questions

1. How can someone wholesale real estate while moving frequently?

Instead of starting in each new location, focus on one market you are familiar with. Derek stayed focused on Louisville and partnered with locals to handle in-person tasks while he worked virtually.

2. What marketing methods work best for virtual wholesaling?

Derek relies on ringless voicemails, text campaigns, and cold calling absentee owners. These proactive strategies outperform free listing sites, which typically yield only a few deals per year.

3. Is wholesaling real estate still viable for beginners?

Yes. Derek started with no real estate experience and made $8,000 on his first deal. The key is building systems, staying consistent, and focusing on activity rather than luck.

4. How many deals do you need to change your financial future?

Even one deal a month can make a major difference. For many beginners, that level of consistency can replace a job or create freedom to pursue other opportunities.

Samantha Ankney

About Samantha Ankney

Samantha is the Social Media Manager at DealMachine, where she oversees all social media strategies and content creation. With 4 years of experience at the company, she originally joined as a Media Specialist, leveraging her skills to enhance DealMachine's digital presence. Passionate about connecting with the community and driving engagement, Samantha is dedicated to sharing valuable insights and updates across all platforms.