Lessons from the 2008 Crisis: Reshaping Real Estate Financing with Jay Conner

***Guest Appearance

Credits to:

https://www.youtube.com/@thehustleandgrind 

"From Crisis to Opportunity with Jay Conner"

https://www.youtube.com/watch?v=NNMrBDzu4Tk 

For many real estate investors, securing funds is the biggest hurdle between a great deal and realizing their financial dreams. Most head to the bank, grovel over loan terms, expose every aspect of their financial lives, and play by the bank’s ever-changing rules. But what if there were another way—one where you set the terms and build a truly resilient business? 

On a recent episode of Raising Private Money, Andrew Chesnutt sat down with Jay Conner, a private money maven who transformed a funding crisis into a multi-million-dollar real estate machine.

The Crash That Changed Everything

Jay’s story is a timely reminder that business growth rarely happens when everything is easy. In 2009, after six years of steady real estate deals funded the traditional way, Jay’s banking lifeline was suddenly severed. The 2008 financial crash had prompted his banker to pull the plug on his line of credit overnight—leaving Jay with two properties under contract that represented over $100,000 in potential profit, but with no funds to support them.

That moment of crisis posed a question every entrepreneur can relate to: Who do you know that can help fix your problem? For Jay, a call to a friend turned him on to the world of private money—individuals willing to invest directly in real estate deals for secure, healthy returns.

Building a System Without Begging for Cash

Jay’s biggest breakthrough came when he realized he didn’t have to beg for money or pitch risky one-off deals. Instead, he created a private lending program with clear rules: an 8% interest rate, no origination fees, and loans never exceeding 75% of a property’s after-repair value. 

He started teaching those in his network—church members, Rotary Club friends, local professionals—about how they could earn high, safe returns by becoming private lenders. Importantly, he focused on education, not desperation. “Desperation has a smell,” Jay points out. Building trust before you need the money puts you in the driver’s seat.

Once a relationship and understanding exist, funding deals become a matter of making what Jay calls the “great news phone call.” Instead of a hard sell, Jay simply calls to let his lender know there’s an opportunity to put their money to work in a secured deal. This calm, methodical approach has allowed Jay to raise millions in private funding—with 47 private lenders at last count—all without pitching or pleading.

Why Private Lenders Love It

Why are private lenders so eager to work with Jay? He cites three main reasons:

1. Higher Returns: Compared to certificates of deposit (CDs) or most traditional options, that 8% fixed rate is unbeatable and often more stable than the stock market roller coaster.
2. Security: Notes are collateralized against real estate, private lenders are named on insurance policies, and safeguards are in place in case of emergencies.
3. Predictability: Unlike the volatility of 401(k)s or mutual funds—where most investors can’t even quote their exact returns—private lenders know precisely what they’ll earn, with no hidden fees or commissions eroding their gains.

Creative Financing Adds More Flexibility

Private money is just one tool. Jay and Andrew discuss layering creative financing: combining private loans with strategies like “subject-to” purchases, seller financing, and even structuring first-position loans across multiple investors. These methods increase deal-making flexibility, help investors pivot if challenges arise, and offer lenders more options and comfort.

Final Takeaways