From Classroom to Closing Table: The Journey of Chris Cheff in Creative Real Estate Financing

May 15, 2025•4 min read

From Classroom to Closing Table: The Journey of Chris Cheff in Creative Real Estate Financing

Have you ever wondered what it takes to make real estate deals happen behind the scenes? In this transformative story of resilience and innovation, meet Chris Cheff, founder of Prima Fund LLC, who left his 20-year teaching and coaching career to dive headfirst into the world of real estate funding. Chris has redefined the game with his expertise in bridge loans, EMDs, and transaction capital, setting new standards for minimizing risks while maximizing returns. Let’s unpack his unique strategies and learn how this industry expert is reshaping the real estate investing landscape.

Trading the Classroom for Real Estate Success

Chris Cheff’s journey is nothing short of inspiring. After dedicating two decades to teaching and coaching, Chris decided to pivot his career and explore the opportunities in real estate investing. Today, he is at the helm of Prima Fund LLC and Las Vegas Elite Investments, focusing on creative funding solutions that fuel property deals. His work spans secondary financing, bridge loans, and even innovative ventures such as exotic car rentals. Chris’s ability to adapt to changing markets and seize niche opportunities, such as land plays in the Rockies, proves that reinvention is the key to long-term success.

Why Flipping Isn’t Always the Answer

While many real estate investors start with flipping houses, Chris realized that the stress and organizational challenges weren’t for him. Instead, he found his niche in financing, offering solutions like gap funding for experienced borrowers. By focusing on shorter-term investments, typically lasting 4 to 8 months, he ensures fast transaction cycles and solid returns. Chris’s mantra? “There are other ways to make money in this space without the stress of flipping.”

Innovative Strategies in Secondary Financing

Chris’s approach to secondary financing sets him apart from others in the field. Unlike typical gap financing, which often involves risky second lien positions, Chris employs creative security structures to minimize risks for all parties involved. He integrates meticulous due diligence into his process, vetting not only the deals but also the borrowers, contractors, and even permitting offices. His unique method ensures that every transaction is built on a foundation of trust and accountability.

Lessons from Challenges and Setbacks

Real estate investing is not without its hurdles, and Chris has faced his fair share. From navigating permit delays in cities like Philadelphia and Atlanta to dealing with unforeseen borrower issues, such as health crises, Chris has learned that thorough preparation is vital. He warns against working with inexperienced borrowers and emphasizes the importance of clear documentation and robust security measures. As he puts it, “Every deal is unique, and you just have to vet it and balance it the best you can.”

Building Trust Through Transparency

One of Chris’s standout strategies is his commitment to transparency. Before investors commit to deals, he encourages them to do their own underwriting and even offers recorded interviews with borrowers to build confidence. “We want everyone to be 100% comfortable with the opportunity,” he explains. His collaborative approach extends to post-closing Zoom meetings with borrowers and capital partners to align expectations and ensure a smooth project start.

Networking and Raising Capital

For Chris, networking is a cornerstone of success. Whether through events or platforms like LinkedIn and Instagram, he consistently connects with potential investors and borrowers. His focus is on working with experienced investors looking to scale their businesses. He also leverages educational opportunities, offering office hours and participating in investment groups to guide newer investors and help them avoid common pitfalls.

Key Takeaways for Investors and Borrowers

Vet Everything: From borrowers to contractors to market conditions, thorough due diligence is non-negotiable.
Focus on Security: Chris’s innovative security structures offer peace of mind for investors and borrowers alike.
Embrace Transparency: Open communication builds trust and ensures smoother transactions.
Learn from Challenges: Every setback is an opportunity to refine your approach and improve future outcomes.
Network to Grow: Building relationships is essential for raising capital and scaling your business.

Conclusion

Chris Cheff’s journey from classroom to closing table is a testament to the power of adaptability, innovation, and determination. His unique strategies in creative financing, combined with a commitment to transparency and education, have redefined success in real estate investing. Whether you’re an experienced investor or a borrower seeking to scale, Chris’s insights are invaluable. Ready to take your investing to the next level?

Reflective Question: How can you apply Chris’s principles of due diligence and transparency to your own investment strategies?