Raising Private Money with Jay Conner

Guest AppearanceCredits to:https://www.youtube.com/@yieldcoach                               “S02 E37 - Jay Conner - The Big Fish in a Little Pond”https://www.youtube.com/watch?v=c8SRgpoCfXU&t=46s  When most people imagine real estate investing at scale, they picture bustling cities and high-profile investors closing multi-million-dollar deals in large urban centers. Jay Conner’s story, as revealed in his guest appearance on Ian Brown’s Yield Coach Show, flips this conventional wisdom on its head. Based in a market of just 40,000 people, Jay has built a thriving operation, completing over 475 rehabs and maintaining an impressive average profit of $78,000 per flip—all by leveraging the power of private money.Building a Real Estate Machine in a Small MarketJay’s journey began in the housing industry alongside his father, who once owned the country’s largest mobile home retail operation. Witnessing an abrupt end to consumer financing for manufactured homes, Jay transitioned into single-family investing in 2003. Rather than chase larger markets, he decided to master his small local area, demonstrating that significant profits can be earned even far from the big city spotlight.Initially, Jay started solo. By his own admission, the first year’s three house flips were ambitious for a team of one. Over the years, he scaled up, and today his local operation handles two to three properties monthly—all without the intense competition or wholesale activity common in larger markets. In fact, Jay notes that wholesaling isn’t even present in his area; he’s the go-to buyer.The Power of Positioning Private Money FirstOne of the most important shifts in Jay’s approach came during the financial crisis of 2008. When traditional bank financing suddenly collapsed, as it did for so many investors, Jay had to rethink his approach. Instead of relying on banks that could shut down credit lines with a single phone call, he began raising private capital. Within three months, he’d secured more than $2 million by educating local contacts about the returns and security of lending on real estate deals, often via self-directed IRAs.Rather than approaching private lenders with a sense of desperation or pitching specific deals, Jay positions himself as a teacher. He explains the safety features and returns of private lending, building trust and credibility. Prospective lenders learn about the process, and when they’re ready, they’re excited to lend—often reaching out proactively to fund deals. This mindset shift—from asking for money to offering an investment opportunity—has been foundational to his success.Jay now works with 47 private lenders, who collectively provide about $8.5 million in funding for his deals. Private loans typically come in at 8% interest for first-position liens and 10% for subordinate liens. Regular people—retirees, acquaintances, friends from church, and family—make up this lender base. Many had never even heard of private lending or self-directed IRAs before Jay introduced these concepts.Automation and Smart Deal FlowJay’s streamlined operation is built on proactive, automated marketing and systematic deal flow. His company deploys multiple Google and Facebook pay-per-click campaigns using third-party vendors. By running three separate campaigns under different names, he maximizes lead generation and dominates the search results for motivated sellers in his local market. Despite paying $150 per Google lead, he needs only seven prospects to secure a purchase, given his acquisition strategy.Direct mail to pre-probate and foreclosure lists, high-conversion sequences, and direct outreach to new wholesal

Many investors are told the only path to financial security is to trust Wall Street with their savings, accumulate as much wealth as possible, and hope it all works out decades later. But in a recent episode of Raising Private Money, host Jay Conner sat down with Chris Miles—the Cash Flow Expert—who has taken a dramatically different route. Rather than focusing on traditional stock-driven strategies, Chris has built true financial freedom around creating multiple streams of passive income, helping clients unlock over $300 million in increased cash flow along the way.Why the Traditional Financial Playbook Falls ShortChris’s journey began in the traditional world of financial advising. He was taught, and taught his clients, the standard advice: save diligently, fund your 401(k), pay off debt, and wait for compounding returns to deliver financial freedom in retirement. But after analyzing his own dad’s finances, Chris saw firsthand how this advice doesn’t always deliver. Even debt-free savers with healthy retirement accounts can fall short, sometimes outliving their money or missing out on years of opportunity.This realization fueled Chris’s break from traditional financial advice. He found most advisors couldn’t achieve financial freedom themselves through Wall Street-centric methods—they relied on commissions, not returns from the same products they recommended. Chris sought alternative paths: real estate, hard money lending, mineral rights, and other assets that actually produce cash flow.The Power of Diversified, Passive IncomeWhat makes Chris’s approach so compelling is its focus on income streams that show up whether you work or not. Instead of chasing net worth for the sake of status, Chris encourages focusing on cash flow—the real scoreboard for financial independence. If your investments generate income that exceeds your expenses, you’re free from the rat race—regardless of how much you have “on paper”.His investment strategies include turnkey rental properties for hands-off cash flow, hard money lending to earn steady returns from financing others’ deals, and mineral rights investments that benefit from rising commodity prices. Chris also takes advantage of syndications and various forms of business partnerships. The keys are diversity, control, and the ability to pivot as markets shift.Biggest Mistakes Investors MakeWhen new clients come to Chris, they almost always have untapped opportunities and a few common financial mistakes holding them back. Taxes are a major issue: many business owners and investors don’t have proactive accountants who help minimize their tax burden. Others still believe maxing out IRAs and 401(k)s is a winning tax strategy, when it may just be deferring higher taxes to later years. Another frequent blind spot is simply not tracking cash flow closely—money leaks from unmonitored expenses can quickly eat away at freedom.Chris’s process starts by examining clients’ cash flow microscopically, finding places to restructure debt, reduce taxes, or reallocate underperforming assets. Often, it’s possible to build or accelerate passive income just by “freeing up” money already sitting idle in stocks, low-yield accounts, or poorly leveraged properties. For example, by selling a non-cash-flowing rental or repositioning assets, some clients unlock thousands in new monthly income without even taking on new investments.Cash Flow Versus Net Worth MindsetChris is adamant that cash flow, not net worth, is the measure of real progress. Net worth looks impressive, but unless it generates reliable income, it won’t buy time or freedom. Like a business chasing revenue but ignoring profit, an investor can have a high net worth but little spending power or security. Financial freedom is achieved by generating enough passive income to comfortably meet (and exceed) living expenses—no matter what the market does.

Ari Page, founder and CEO of Fund&Grow, helps entrepreneurs secure large 0% introductory business credit. He explains how business credit cards can replace hard money for rehabs, using third-party processors to pay vendors and escrow. Ari also covers qualification basics, typical funding timelines and rounds, and why professional negotiation boosts approvals.

Guest AppearanceCredits to:https://www.youtube.com/@JohnCasmonMultifamily                              “5 Steps to Raise Private Money with Jay Conner, Ep. 419”https://www.youtube.com/watch?v=wkFic8doqB4 Securing funding is one of the greatest challenges real estate investors encounter, especially when traditional sources suddenly dry up. This was the reality for Jay Conner, who experienced a dramatic turning point in 2009. For years, he relied on conventional bank loans to fund his deals, but with the onset of the global financial crisis, his dependable stream of capital was abruptly shut off. Faced with the sudden closure of his line of credit, Jay Conner was forced to seek alternative ways to fund his investments—and what started as a setback soon became a catalyst for unprecedented growth.The pivotal moment came with a simple phone call. Jay Conner reached out to fellow investor Jeff, who introduced him to private money—a different way to fund deals that doesn’t rely on institutional lenders or hard money brokers. This revelation inspired Jay Conner to quickly educate himself about private lending, particularly how individuals, rather than companies or funds, could serve as lenders using both personal and retirement capital.The crucial difference between hard money and private money was a game-changer. Hard money typically comes from companies that raise funds from individuals, then lend at double-digit interest rates, often with origination fees and rigid terms. In contrast, private money involves direct relationships with individuals—people in your network who may have funds in savings or retirement accounts yielding low returns. With private lenders, the real estate investor has much more flexibility and often gets better terms, such as lower interest rates, no points or fees, and even the potential to borrow the entire purchase price and rehab costs with minimal upfront payments.Recognizing these advantages, Jay Conner shifted his approach. Instead of desperately chasing down money, he adopted a teaching mindset, educating people in his network about the benefits of private lending. He never positioned himself as a salesman or beggar. Instead, he focused on value—demystifying the process for others and showing them how they could earn strong, safe returns secured by real estate.His process began with identifying connections within his existing network, particularly focusing on retirees or people likely to have investible capital. He’d reach out to them casually, establishing rapport, and asking one powerful question to prequalify interest: whether they had investment capital or retirement funds that weren’t achieving attractive, secure returns. If the contact expressed interest, Jay Conner would share educational material—a concise audio overview explaining private lending’s key concepts and advantages, deliberately crafted to inform rather than persuade. The goal was to make people curious, not pressured, allowing them to self-select into learning more.When a potential lender expressed further interest, Jay Conner would walk them through the exact program, explaining rates, terms, safety protocols, and how their funds would be secured by real estate with documentation like promissory notes, mortgages, or deeds of trust, and proper insurance and title protection. Only after all questions were answered and the lender verbally pledged funds would Jay Conner match those funds with a specific deal. He’d call with the key facts: location, after-repair value, required funding amount, and closing timeline—never asking if they wanted to participate, but instead simply informing them how and when their money would go to work.This education-ce

If you’re a real estate investor, the endless hustle of cold calling, chasing sellers, and competing with lowball offers probably sounds familiar. Many entrepreneurs get into real estate for the promise of financial freedom, but often find themselves overwhelmed, stuck on the outbound hamster wheel, and struggling to build a business that supports the life they want. In a candid conversation on the Raising Private Money podcast, host Jay Conner and real estate innovator Keith Gillispie offer a roadmap for breaking out of this cycle—and achieving a new level of consistency, confidence, and freedom.The Power of Choosing a Different PathKeith Gillispie never set out to build an “outbound marketing” empire. His real journey began while serving overseas with the Marine Corps, repeatedly missing precious years with his young family. After realizing he was unintentionally repeating a pattern from his own childhood—his dad died when Keith was eight—he made a conscious decision to architect a business that would allow him to be present for his kids.This key moment illustrates something every investor needs to hear: you have the power to choose how you build your business and your life. Keith walked away from the traditional grind, even after years of outbound efforts, and consciously engineered a different route.Why Inbound Systems Beat Outbound HustleFrom 2016 to 2020, Keith relied heavily on outbound marketing. After years of cold calling, door knocking, direct mail, and other traditional methods, he realized these tactics weren’t sustainable—or enjoyable. From 2020 onward, he shifted to inbound strategies. This meant building systems, so leads came to him, rather than him chasing deals.The difference? When sellers come to you, the dynamic is completely transformed. Instead of competing on price alone or convincing someone to sell, you become a problem solver. Sellers with urgent needs—divorce, inheritance complications, pre-foreclosure threats, or health issues—reach out because they see you as a trusted solution provider.This paradigm shift also changes who has the “gold” in the sales conversation. Instead of the seller holding all the cards, Keith establishes himself as the one who can genuinely help, often providing something that goes beyond just a higher offer—a proven ability to close, personalized attention, or creative deal structures that truly solve the seller’s problem.Systemization: The Secret to Scaling with ConsistencyHow did Keith go from missing family dinners to building a business that operates in 34 states? The answer lies in systems. He draws inspiration from companies like McDonald’s, where every process—down to the amount of mayonnaise or the placement of pickles—is standardized for repeatable results. In Keith’s business, every step follows a system: marketing generates the same quality and quantity of leads, scripts for triage calls are dynamic and adjust as conversations evolve, and deal analysis follows a clear, step-by-step protocol for consistency.These systems aren’t just for show—they allow for high-quality delegation, with affordable virtual assistants following standard operating procedures (SOPs) documented with visual tools and short video walkthroughs. This meticulous approach ensures every deal follows the same “conveyor belt,” from initial lead to triage, analysis, structuring, and funding.Solving Real Problems, Not Just Making OffersOne of the most important takeaways: success in real estate isn’t just about offering more money. It’s about uncovering and addressing the true needs of sellers. Keith’s process involves genuinely understanding a seller’s situation before presenting a solution—akin to a doctor diagnosing before prescribing. Sometimes sellers accept his offer even if it isn’t the highest, simply because they trust him to deliver or because he’s addressed chall

Jay Conner, private money authority and real estate investor who teaches investors to raise capital, shares how direct individual lending unlocks deals fast. He explains what private money is, why it matters now, how to find and educate lenders, loan security and structures, and creative combos like seller financing. Practical tips for closing quickly and lining up funds before making offers.

Jay Conner, a real estate investor who built a private money program after 2009, shares his journey from mobile homes to rehabbing hundreds of houses. He explains how losing bank credit pushed him to private money and self-directed IRAs. He lays out how he structured lender terms, the outreach script that converts investors, and why lining up funds before contracts wins deals.

Jay Conner, real estate investor who has flipped 300+ homes and built a seven-figure, largely automated investing business. He discusses small-town investing advantages and creative buying and selling strategies. He explains how private money transformed his model and how automation and a lean team scale deal flow.

***Guest AppearanceCredits to:https://www.youtube.com/@RafaelCortezCEO                          “EP 71 | JAY CONNER - This is the right way to find private money for your deals! | Investor strategies.”https://www.youtube.com/watch?v=TuS1QNcmiCw   In the dynamic world of real estate investing, access to capital often determines how quickly you can seize opportunities and scale your business. Many investors focus on traditional bank loans or hard money lenders, but there’s a powerful funding alternative that can transform a real estate business: private money. This topic was expertly explored when Jay Conner joined Rafael Cortez on the CEO Pulse Podcast, sharing his journey, strategies, and mindset that have made him a standout in the industry.Jay Conner’s path into real estate began in the early 2000s, after years in the manufactured and mobile homes sector. In a small town in Eastern North Carolina, with a population of just 8,000 and a target market of 40,000, he found success not by volume, but through creating consistent high-value deals. His average profit per deal stands at an impressive $71,000, a testament to the effectiveness of his approach in a niche market.One pivotal moment in Jay’s business occurred during the financial crisis of 2009. Prior to this, his deals were funded through local banks, relying heavily on lines of credit. Suddenly, with two lucrative properties under contract and over $100,000 in potential profit at stake, Jay discovered that his bank had closed his lines of credit. The market downturn had dried up traditional funding without warning. Rather than quit, he sought new answers—and that search led him to private money.Private money, as Jay describes, is sourced from individuals—ordinary people with investment capital or retirement funds who are looking for secure, high returns. Unlike hard money lenders, who act as intermediaries and often charge higher rates and fees, private money comes directly from the source. For investors, this means lower interest rates, fewer fees, and greater flexibility. Jay’s system allows him to fund deals with up to 150% of the after-repair value, often resulting in a large check at closing with no out-of-pocket contributions.Building a network of private money lenders hinges on education and relationship-building. Jay’s strategy doesn’t involve begging or desperately pitching deals. Instead, he focuses on teaching potential lenders about the value and security of real estate investing, particularly through self-directed IRAs. The education-first approach helps people understand how their funds can work harder, often yielding much higher returns than traditional financial products. Once the concept and program are explained, lenders are enthusiastic to participate—often finding Jay before he finds them.Jay emphasizes the importance of having a clear, attractive private money program in place. This includes specifying interest rates, protective measures (like securing the loans with a mortgage or deed of trust), insurance, and a clear process for accessing funds or calling the note. Establishing relationships with self-directed IRA companies is also a key step, enabling lenders to invest with tax advantages.For those new to raising private money, Jay outlines a five-step process: start by making a list of potential lenders within your warm market, initiate casual conversations (either one-on-one or in group settings like luncheons or Zoom calls), provide educational materials, teach the lending program in detail, and finally, secure a verbal pledge. Only after a lender is informed and committed do you match them with a deal, which projects confidence and proper preparation.Jay’s approa

***Guest AppearanceCredits to:https://www.youtube.com/@WayneVeldsman                         “He Raised $8 Million Without Banks..! Jay Conner’s Faith‑Driven Path to Financial Freedom | JTL 131.”https://www.youtube.com/watch?v=5jjG6ylaubY&t=13s  The journey to legacy in entrepreneurship often begins not with a blank slate, but in the midst of adversity. The story shared by Jay Conner in his conversation with Wayne Veldsman is a testament to how true breakthroughs often arise from the very problems that threaten to shut us down.Jay Conner, known widely as the Private Money Authority, didn’t step into the real estate world on a winning streak—his early years were spent navigating the traditional, often painstaking path of bank-funded deals. Like many investors, he played by the rules of the banks: filling out applications, sharing personal financials, and hoping for approval. It wasn’t until a pivotal moment in 2009, when his line of credit was revoked without warning despite a spotless repayment record, that everything changed.Rather than succumbing to defeat, Jay Conner chose to see his challenge as a problem to be solved, not an end to his ambitions. His solution? He reached out to his network, discovered the world of private money and self-directed IRAs, and quickly realized he could bypass traditional lenders altogether. The approach was transformative: within 90 days, he raised over $2 million in private funding by educating individuals in his circle about alternative investments, sometimes gathering nearly a million at a single luncheon.This experience shaped a guiding principle for Jay Conner: the money should come first in real estate investing, not just the deals. Contrary to common advice that securing property comes before securing funds, Jay Conner advocates for building your financial firepower first. Doing so unlocks confidence and agility in a competitive marketplace, letting investors make offers knowing funding is already in place.What truly sets Jay Conner’s story apart is the mindset at the heart of his success. He makes it clear that the biggest stumbling block for aspiring entrepreneurs isn’t the lack of opportunity or resources, but fear—specifically, fear of the unknown. Many are daunted by the prospect of trying something new, or are too focused on themselves in networking situations. But the traits that define successful people, Jay Conner argues, include relentless curiosity and the willingness to move beyond their comfort zones. This “childlike curiosity”—always asking “why” and seeking to learn—turns what could be stumbling blocks into stepping stones.Jay Conner also highlights the critical role of community and mentorship. He admits his early mistake was trying to figure everything out on his own, relying on past experiences from a different industry. The value of surrounding oneself with like-minded individuals in mastermind groups or professional circles cannot be overstated. These connections foster growth, provide support during challenging transitions, and allow for the rapid acquisition of new knowledge.Integral to Jay Conner’s philosophy is the idea of leading with service. Instead of chasing, persuading, or pitching deals to lenders, he approaches potential investors as an educator, focused on offering value and exposing them to new opportunities. He explains that many of his private lenders had never considered alternative investments until he introduced the idea, and he helps them benefit from higher returns either through investment capital or leveraging assets like home equity or insurance.At the core, Jay Conner’s approach is rooted in faith and the desire to help others—a “servant’s heart.” This a