Advanced Real Estate Marketing and Private Funding Strategies with Jay Conner

***Guest Appearance

Credits to:

https://www.youtube.com/@RawandRelentlesswBoDePaoli-d2f                                              

“How Jay Conner Raises Millions Without Banks or Hard Money”

https://www.youtube.com/watch?v=8DvcXxvSQW8&t=11s    

When it comes to real estate investing, adapting to changing markets and leveraging innovative strategies can separate the average investor from a true powerhouse. In the recent Raising Private Money podcast, renowned private lending expert Jay Conner shared a revealing behind-the-scenes look at how he navigates today’s tough real estate landscape, uncovers valuable off-market deals, and consistently secures funding without relying on banks or hard money lenders.

The End of MLS Deals – And the Shift to Off-Market

After 22 years of investing in single-family homes in Eastern North Carolina, Jay Conner has seen the market evolve. He explained he hasn’t bought a single-family house listed on the MLS with a realtor in over five years, a change accelerated by the disruptions of COVID. Instead, he now focuses entirely on for-sale-by-owner properties that are off the market, which he describes as “potentially motivated sellers” that other investors simply aren’t reaching.

Why this focus? The competition for on-market properties has become fierce, with TV shows and increased awareness drawing more people into the flipping game. To stay ahead, Jay targets sellers who aren’t working with agents and may be facing distress or unique life circumstances.

Where Do Today’s Deals Come From?

To consistently find off-market deals, Jay Conner emphasizes three main strategies:

1. Direct Mail to Families Facing Foreclosure
   Since 2004, Jay has tracked families facing foreclosure and sends a series of eight direct mail letters spaced three days apart, offering solutions rather than taking advantage of their situation. Most of these properties, he notes, end up selling on terms “subject to the existing note,” a technique allowing acquisition without immediate large investments.
2. Inherited Properties
   Jay also targets property heirs through direct mail, running a campaign that stretches 90 days apart over two years. The messaging is tactful, never directly mentioning inheritance, and simply offers to buy the home should they be interested.
3. AI-Driven "Driving for Dollars"
   Technology is rapidly shifting the marketing game. Jay recently began using an AI-powered service that scours Google Maps and Earth for signs of property distress—everything from roof issues to unkept yards—assigning each property a score. Direct mail is then targeted specifically to properties most likely to need a quick sale.

Leveraging Private Money – No Banks, No Hard Money

One of the biggest hurdles in real estate is access to capital. Jay’s story illustrates how traditional funding sources can dry up overnight—he shared how his local bank cut off his line of credit without warning in 2009, despite years of successful business. This crisis forced him into new territory: private lending.

Instead of chasing, begging, or negotiating with banks and hard money lenders (who charge 12%-14% plus origination fees), Jay built a network of individual private lenders—people in his own community, at his church, or in his cell phone contacts—offering them predictable, attractive returns at 8%, with no points and no fees.

How does he attract these lenders? He positions himself as a “teacher,” educating would-be investors about the opportunity and how they can use vehicles like self-directed IRAs to fund his deals safely and often tax-deferred or even tax-free. Importantly, he separates the conversation about the opportunity from the specific deals, avoiding any whiff of desperation and letting the quality of the program speak for itself.

Embracing Automation and AI

Efficiency matters. Jay Conner has built his business so that he works less than 10 hours per week, thanks in part to powerful automations through CRMs like Go High Level, Zapier integrations, and even conversational AI that responds to and qualifies new seller leads within minutes. He’s currently testing AI services that can call, text, and follow up automatically—allowing him to scale outreach far beyond what a single team member could accomplish.

Lessons for Investors

Jay’s journey is a vivid example of why adaptability and an education-first approach matter. By targeting non-traditional sellers, building a local private lender network, and embracing tech innovation, he’s built a scalable, resilient business—not just surviving, but thriving as markets shift.

Whether you’re a new investor or a seasoned pro, the takeaway is clear: mastering the art of finding off-market deals and raising private money can change the trajectory of your career. And in an age of rapid automation and AI, keeping your marketing and funding strategies at the cutting edge is more important than ever.

10 Discussion Questions from this Episode

1. Jay Conner highlights that he hasn’t bought a property through the MLS in over five years, focusing instead on off-market, for-sale-by-owner deals. What are the advantages and disadvantages of this approach in today’s real estate market?
2. During the 2008–2009 financial crisis, Jay Conner switched from traditional bank financing to private money. How did this shift impact his business, and what lessons can be learned for investors facing financing challenges?
3. What are the key differences between private money and hard money lending, and why does Jay Conner prefer private lenders to institutional or hard money lenders?
4. The episode describes a teaching mentality when approaching potential private lenders. How does this strategy differ from traditional fundraising or sales pitches, and why does it work for Jay Conner?
5. Desperation is said to “have a smell,” and it’s recommended to separate conversations about lending programs from deal-specific asks. How can this mindset shift improve success rates in raising private capital?
6. With an average annual return of 8% for private lenders and no points or origination fees, what makes this deal attractive to everyday investors compared to more sophisticated or institutional opportunities?
7. The use of self-directed IRAs allows private lenders to invest using their retirement funds, potentially tax-deferred or tax-free. What are the risks and rewards of this strategy for both lenders and borrowers?
8. Jay Conner details multiple lead generation strategies, including direct mail to homeowners in foreclosure or inherited property situations, as well as leveraging AI and Google pay-per-lead services. Which method do you think is most effective in today's environment, and why?
9. The increasing role of AI in real estate marketing and lead qualification was discussed extensively, including the use of AI phone calls and messaging. How do you see AI transforming real estate investing and deal origination over the next five years?
10. Jay Conner suggests that technological advancements, like AI, will reshape roles in real estate investing rather than eliminate them. Do you agree with this outlook, or do you foresee significant disruptions to jobs and traditional roles in the industry? Why or why not?

Fun facts that were revealed in the episode: 

1. Zero MLS Purchases in Five Years
   Jay Conner revealed that he hasn’t bought a single-family home listed through a realtor or the MLS in over five years, instead sourcing all his deals off-market or directly from for-sale-by-owner opportunities.
2. AI Is Changing Real Estate Deal Hunting
   The episode highlighted a cutting-edge "AI Driving for Dollars" system that uses artificial intelligence, Google Maps, and Google Earth to identify distressed properties by analyzing images for 16 points of distress—completely revolutionizing how investors find off-market deals.
3. Creative Private Lending Education
   Jay Conner shared his unique "teacher hat" approach: rather than asking people for money, he educates them on private lending and self-directed IRAs. Notably, when he started, none of his 47 private lenders had ever heard of private money or self-directed IRAs, showcasing the power of education in building investment partnerships.

Timestamps:

00:00 Flipping houses in smaller markets

05:13 Facing a financial crisis

09:42 Separating opportunity from funding requests

10:42 Explaining self-directed IRAs

13:45 Pitching investment opportunities

19:14 Managing multiple renovation projects

21:12 Introducing private lending concepts

25:42 Using private money for real estate

28:11 Finding Off-Market Property Deals

30:38