Zen and the Art of Real Estate Investing with Jonathan Greene

051: Transforming Lives Through Real Estate with Matt Faircloth


What if you could journey from your first house hack to owning a real estate empire? Brace yourselves for an eye-opening conversation as Jonathan interviews Matt Faircloth, the founder and CEO of DeRosa Group and the author of the Amazon bestseller Raising Private Capital. 

In this episode of Zen and the Art of Real Estate Investing, Matt unravels his audacious journey to real estate investing, which he embarked on with his wife in 2005, inspired by the book Rich Dad Poor Dad. He talks about their humble start with a house hack outside of Philadelphia to their eventual foray into commercial real estate despite challenging circumstances.

Do you want to know what it takes to turn adversity into opportunity in the world of real estate? Listen in as Matt shares how he and his wife battled multiple challenges, from roommate issues to a collapsing economy, and turned a potential disaster into a success. He shares the story of their investment in an office building and how they turned it around when the plan to rent it to the state of New Jersey fell through. Hear how they transformed this setback into a win by converting the building into profitable micro office leases modeled after Regis.

Lastly, Matt offers invaluable advice on the importance of building trust, maintaining integrity, and developing a solid track record when seeking outside investors. He warns against relying on “gurus” and urges new investors to emphasize doing right by people. He also discusses the Roster Group’s strategy for diversifying investments, the benefit of investing in multifamily units, and the importance of having the right mentor and business systems in place.

In this episode, you will hear:

  • Matt Faircloth’s journey from house hacking in Philadelphia to becoming a seasoned real estate investor and CEO of DeRosa Group

  • The challenges and lessons he’s learned in real estate investing, including a failed plan to rent an office building to the state of New Jersey

  • Matt’s views on the importance of building trust, maintaining integrity, and educating potential investors in the real estate industry

  • The value of diversifying investments and avoiding reliance on “gurus” in the real estate space

  • What the benefits of investing in multifamily housing are, and how to identify genuine and fake gurus in the real estate industry

  • Matt’s first experience of raising capital from investors outside his immediate family, marking a significant step in scaling up his real estate investment business

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Supporting Resources:

DeRosa Group –

DeRosa Group on YouTube –

Matt Faircloth on Instagram –

Connect with Matt on LinkedIn –

Raising Private Capital by Matt Faircloth –

BiggerPockets –

Website –

YouTube –

Instagram –

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TikTok –

Zillow –

Bigger Pockets –

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