Real Estate Investing Lessons: How Matt Faircloth Turned Early Failures into Lasting Success

Every investor has a story about the deal that changed everything. For Matt Faircloth, co-founder of DeRosa Group, those deals came early in his career. One property became a costly mistake. The next became a turning point that set the foundation for a successful investing career.

Both experiences hold powerful lessons for anyone looking to build wealth through real estate.

Lesson One: The Fix-and-Flip That Went Wrong

Matt’s very first real estate investment was a small single-family house that he passed every day. It looked like a great opportunity. The numbers seemed simple: buy low, fix it up, and sell high.

But once renovations began, the problems appeared.

• Termite damage on the second floor

• Structural issues that made parts of the property unsafe

• Ceilings that were too low for modern code requirements

• Portions of the home not even built on a proper foundation

  
  

Instead of reassessing the project, Matt pressed forward. A new roof went on. Contractors gutted the house. Eventually, it was torn down and rebuilt. When the property finally sold, it sold at a loss.

The mistake? Going in without a clear, step-by-step plan for profitability. Matt let the property’s problems dictate his decisions, instead of starting with a business plan that ensured a return.

This first lesson became clear: never enter a deal without a mapped-out path to profit.

Lesson Two: The Estate Sale That Changed Everything

Not long after that painful first deal, Matt purchased an estate sale property in Trenton, New Jersey. It was a four-bedroom, two-bath home bought for $40,000, with $40,000 budgeted for renovations.

This time, Matt took a different approach. He went in with multiple exit strategies:

• Rent the property for $1,200 per month

• Sell for roughly a $20,000 profit

  
  

The numbers worked either way. The investment was safe from the start.

Matt chose to rent the property, which generated stable cash flow. Later, when another investor wanted to expand in the neighborhood, he sold. Because he had more than one way out, he protected his downside and locked in upside potential.

The Lasting Takeaways for New Investors

These two early experiences shaped Matt’s entire investing career — and ultimately the approach of the DeRosa Group. The key lessons apply to every real estate deal:

1. Always start with a clear plan from A to Z.Know exactly how the property will generate income or create value before you buy.

2. Always have multiple exit strategies.The market changes, financing changes, and tenants’ needs change. Deals built on one narrow strategy are high-risk. Deals structured with flexibility are resilient.

   
   

These rules are simple, but they are often overlooked by new investors. Following them can mean the difference between losing money and building long-term wealth.

Avoiding the Same Mistakes Today

Matt’s first fix-and-flip failure was painful, but it created the discipline that helped him build a portfolio of successful multifamily and commercial deals across the country.

New investors can avoid the same mistakes by educating themselves and adopting proven frameworks from experienced operators. That’s why the DeRosa Group created a free course: How to Buy Your First Apartment Building.

This resource walks new investors step-by-step through identifying, analyzing, and closing their first multifamily deal — so they can skip the costly trial-and-error phase.