The worst time to start raising money for a real estate deal is when you already need the money.

In Episode 13 of When Real Estate Gets Real, I sit down with Jay Conner, known as the Private Money Authority, to break down an alternative approach to funding real estate deals.

Jay started investing in single-family homes in 2003 and initially relied on a bank line of credit. Then, during the 2009 financial crisis, his bank shut down that credit line. With properties already under contract and no traditional funding available, Jay had to find another solution.

That led him into private money.

Jay shares how he went from knowing virtually nothing about private lending to building relationships with private lenders and raising more than $2 million in funding. More importantly, he explains why his approach isn't centered on pitching individual deals.

It's centered on education.

• How Jay discovered private money after losing access to bank financing • Why you should build funding relationships before you have a deal • The difference between private money and hard money • How Jay uses the “indirect method” to start conversations with potential lenders • Why “I need your help” can open a conversation without creating a high-pressure pitch • How private lender relationships can change the way investors approach acquisitions • Why confidence and education matter when talking about capital • How Jay approaches private money as asset-backed debt • How self-directed retirement accounts can enter the private-lending conversation

[00:00] — Meet Jay Conner: The Private Money Authority [01:30] — How Jay Funded His First Real Estate Deals [03:00] — When the Bank Shut Down His Credit Line [05:00] — Discovering Private Money [07:00] — Raising $2.15M Through Education [09:30] — Private Money, Syndication & Asset-Backed Debt [12:00] — The Indirect Method for Finding Private Lenders [16:00] — Why You Shouldn't Raise Money When You Need It [19:00] — Why “The Money Will Show Up” Is Bad Advice [22:00] — Raising Private Money Through Educational Events [25:00] — Private Money vs. Hard Money [28:00] — Jay's Private Money Conference [31:00] — The Mindset New Investors Need [34:00] — How to Connect With Jay

Jay also shares the story behind his first private lender conversation, how a private lender luncheon generated significant funding commitments, and why he believes investors need to stop thinking in terms of asking, begging, selling, or chasing money.

If you've ever found a real estate opportunity but hesitated because you weren't sure where the funding would come from, this conversation will give you another perspective on how to approach the capital side of the business.

Learn more about Jay and his private money resources at jayconner.com.

Jay also discusses his Private Money Conference taking place October 7–9, 2026, in Eastern North Carolina.

Conference details: jayconner.com/event

Get a chance to share your side of the story on When Real Estate Gets Real.

Apply to be a guest: https://whenrealestategetsreal.com/podcast-booking

How do you scale a real estate portfolio while maintaining a full-time career, raising a family, and preparing to take on bigger multifamily deals?

In Episode 12 of When Real Estate Gets Real, I sat down with Hugo Macau, Managing Partner of Forest Estate LLC Commercial Real Estate, to talk about Hugo’s journey from the IT world into hands-on real estate ownership and commercial multifamily investing.

Hugo currently owns nine units across three properties and is preparing to close on a 25-unit portfolio spread across four properties in Providence, Rhode Island. He shares how skills from his IT career including analysis, project management, contract negotiation, and organization have helped him evaluate opportunities and build his real estate business.

But scaling from a handful of units into larger multifamily deals changes the game.

Hugo discusses learning to delegate, building a team of property management, legal, and accounting professionals, working with like-minded investors, and maintaining the standards that matter to him as his portfolio grows.

• How Hugo transitioned from IT into real estate investing • Why the first property can be the hardest one to buy • How corporate skills can transfer into commercial real estate • What Hugo looks for when analyzing real estate opportunities • Why scaling requires learning to trust and delegate • How investor relationships fit into Hugo’s growth strategy • Why tenant experience matters beyond the numbers • Hugo’s goal of reaching 100–200 units in the next year • How generational wealth influences his long-term vision • His advice for people afraid to make their first real estate move

[00:00] — Meet Hugo Macau [01:00] — The 25-Unit Providence Portfolio [02:35] — From Portugal to Canada to the United States [04:20] — Overcoming Fear on the First Real Estate Deal [05:30] — Why Real Estate Became Hugo’s Passion [07:00] — Using IT and Negotiation Skills in Real Estate [09:00] — Balancing Career, Family, and Property Ownership [11:25] — Building Relationships With Real Estate Investors [13:25] — Becoming a Steward of Investor Capital [14:30] — Building a Team to Scale Multifamily [16:30] — Hugo’s Goals for 100–200 Units [18:25] — Generational Wealth and Hugo’s “Why” [20:00] — Advice for New Real Estate Investors [22:15] — How to Connect With Hugo Macau

For Hugo, real estate isn't simply about reaching a certain number of units. It's about building something meaningful, creating homes people value, and establishing a legacy for the next generation.

Want a chance to share your side of the story?

Apply to be a guest: https://whenrealestategetsreal.com/podcast-booking

Most homeowners are sitting on untapped equity without realizing it.

In this episode of When Real Estate Gets Real, Stephen Lee Thomas sits down with mortgage advisor and investor-focused lender Benjamin Stef to discuss how investors are using Home Equity Lines of Credit (HELOCs) to fund deals, scale portfolios, and create opportunities without refinancing low-rate mortgages.

Ben breaks down how HELOCs work, why they've become significantly easier to access, and how investors are leveraging home equity to fund everything from rental properties to private lending opportunities.

The conversation also shifts into entrepreneurship, focus, and the identity changes required to build a successful business without constantly chasing the next shiny object.

• What a HELOC is and how it works
• Why investors are increasingly using HELOCs
• How to evaluate financing opportunities based on ROI
• The difference between active and passive investing
• Why focus is one of the most important entrepreneurial skills
• How successful investors avoid analysis paralysis
• Decision-making frameworks for growing businesses

• Faster HELOC approvals and funding timelines
• Real-world HELOC investing strategies
• Using home equity without refinancing
• Focus vs. distraction in entrepreneurship
• Scaling a business while investing wisely

Website: https://www.fundingfreedom.net/

Youtube: https://www.youtube.com/@UCYZIjA6JcV0DqLD-1q2iZbQ

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