Episode 062: A Candid Conversation with Our Private Money Lenders - Insider Secrets Revealed with Diana and John

Send us a text

Is your deal worth funding in the eyes of private lenders? What makes them say yes or no to funding your deal?

In this episode, Tiffany sits down with two of her biggest private money partners and good friends, Diana and John. Both came from Wall Street backgrounds as stock and bond traders before transitioning into real estate lending. They open up about why they shifted from stocks to real estate, what they look for in borrowers, and the key factors that determine whether they say yes or no when funding deals. From trust and transparency to systems and security, you will hear the insider perspective most investors never get direct access to.

Listen and enjoy the show!

You’ll Learn How To:

• Understand what private lenders value most in a borrower
• Build trust and long-term relationships with lenders
• Raise money without sounding desperate
• Use social media wisely to secure funding by being authentic, disciplined, and transparent
• Use simple money management systems to build confidence with lenders

What You’ll Learn in This Episode:

• (2:13) Diana and John’s career backgrounds before private lending
• (3:27) Falling interest rates pushed them toward real estate investing
• (5:15) How they went from buying rentals to private lending
• (7:44) Competence and character matter most when choosing who to fund
• (9:52) Diversification, consistent returns, and compounding in real estate
• (11:03) How trust, security, and transparency protect both sides
• (12:03) Sharpe Ratio: Measurement of risk versus return in an investment
• (14:12) Breakdown of how private lending works
• (16:04) Tiffany’s simple, not sounding desperate, pitch for raising money
• (18:15) Private lending as an opportunity and not asking for the money
• (22:00) The role of social media in attracting private lenders
• (24:18) Be authentic. Don't memorize a script, not in your own voice
• (30:37) What happens after lenders get their money back, and why they want to reinvest
• (33:24) Systems, team, and infrastructure matter for lender confidence
• (37:08) Using HELOCs and lines of credit to fund deals and earn spreads
• (38:49) Real estate offers more stable leverage compared to stocks
• (41:31) Keep private money in a separate bank account
• (43:22) Diana and John’s plans in real estate and passive investing

Who This Episode is For:

• Real estate investors who want to understand how lenders think
• Entrepreneurs raising capital for deals
• Anyone curious about private money lending as an alternative to stocks
• Business owners looking to build trust with financial partners

Why You Should Listen:

If you’ve ever wondered what private lenders are looking for, or how to attract the right ones, this episode gives you the unfiltered truth straight from lenders themselves. Diana and John share their journey, lessons learned, and practical advice so you can raise money confidently, build stronger relationships, and unlock the funding you need to grow.

Follow Tiffany and Josh here:

• Tiffany Instagram: @tiffanyhighfficial
• Josh Instagram: @joshhighofficial
• Website: https://resultsdrivenrei.com/home/ 
• Get Tiffany’s free resource: www.rdebook.com