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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

The biggest lesson? If you want to level up your real estate investing, look beyond the bank. By proactively educating your network and building a system that benefits everyone, you can transform your funding woes into lasting wealth—on your terms.

If Jay’s story has you rethinking how you fund your next deal, check out his book Where to Get the Money Now. Who knows? The creative, empowering world of private money might be the game-changer your business needs.

10 Discussion Questions from this Episode:

  1. Brandon Richards mentioned that he initially stumbled into easier funding options by chance. How important do you think luck is versus preparation and networking in finding funding for real estate deals?
  2. The conversation highlights the value of private money over institutional funding. What do you believe are the main advantages and potential drawbacks of using private lenders for real estate investments?
  3. Both Jay and Brandon stress the idea of ‘attracting’ money rather than ‘chasing’ it. What are some strategies you’ve seen work (or think might work) to attract private funding in today’s real estate market?
  4. Brandon talks about demystifying the process for private lenders by comparing them to big banks like Chase. How can real estate investors build trust and confidence with potential lenders, especially if those lenders are unfamiliar with the process?
  5. Social media played a significant role in attracting private lenders for Brandon. What kind of social media content do you think is most effective in generating genuine interest from potential investors?
  6. Jay and Brandon both mention the importance of proper documentation (like deeds of trust/mortgages). How much legal and technical knowledge do investors need before approaching private lenders, and where can they learn it?
  7. Brandon transitioned from house flips to land deals and owner-financed notes. What might be some reasons an investor would make a similar shift in their business model?
  8. They discussed scaling from a handful of deals to managing millions of dollars in private money. What are the key challenges investors face in scaling their operations, and how can they overcome them?
  9. Brandon’s CRM, Deal Manager Pro, automates much of the follow-up and deal management process. How important are automation and technology tools for modern real estate investors, and are there risks of relying too heavily on them?
  10. Brandon wishes he’d started with land and note investing sooner. What lessons from his experience do you think could help investors avoid common pitfalls or seize opportunities earlier in their careers?

Fun facts that were revealed in the episode:

  1. Jay Conner Has Never Missed a Deal Due to a Lack of Funds
    Since discovering private money after the 2008 market crash, Jay Conner hasn’t missed out on a single real estate deal because of funding issues—he’s mastered raising private capital.
  2. The “Great News Phone Call” Approach
    Jay Conner raises money without ever directly asking for it; instead, he “teaches” people about the benefits of private lending and then calls them with a “great news” script when an opportunity to invest comes up. This keeps the process friendly and pressure-free.
  3. BYO Bank and “Can’t Decide” CDs
    Andrew Chesnutt’s license plate “BYO BANK” is a nod to the idea that you can be your banker through private lending. He also jokingly calls CDs (Certificates of Deposit) “Can’t Decides”—the place people park their money when they’re unsure what to do with it!

Timestamps:

00:01 Valley Growth and Private Money

04:17 Big Fish, Small Pond Strategy

08:32 Discovering Private Money for Real Estate

11:16 Teaching Secure Private Lending Strategies

15:05 Financial Awareness: B.Y.O. Bank Insight

17:30 Setting Attractive Interest Rates

22:14 Real Estate Finance Strategy

26:30 Lender Positioning Strategy Explained

27:43 Combining Lenders for Loans

31:19 Take 100% Responsibility

33:48 Hustle and Grind Podcast Recap






Private Money Academy Conference:

https://www.JaysLiveEvent.com

Free Report:

https://www.jayconner.com/MoneyReport

Join the Private Money Academy: 

https://www.JayConner.com/trial/

Have you read Jay’s new book, Where to Get the Money Now?

It is available FREE (all you pay is the shipping and handling) at

https://www.JayConner.com/Book 

What is Private Money? Real Estate Investing with Jay Conner

https://www.JayConner.com/MoneyPodcast

Jay Conner is a proven real estate investment leader. He maximizes creative methods to buy and sell properties with profits averaging $67,000 per deal without using his money or credit.

What is Real Estate Investing? Live Private Money Academy Conference

https://youtu.be/QyeBbDOF4wo

YouTube Channel

https://www.youtube.com/c/RealEstateInvestingWithJayConner

Apple Podcasts:

https://podcasts.apple.com/us/podcast/private-money-academy-real-estate-investing-with-jay/id1377723034

Facebook:

https://www.facebook.com/jay.conner.marketing

Listen to our Podcast:

https://www.buzzsprout.com/2025961/episodes/17650820-lessons-from-the-2008-crisis-reshaping-real-estate-financing-with-jay-conner

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