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When Real Estate Gets Real
When Real Estate Gets Real episodes
- Private Money vs. Hard Money: A Better Way to Fund Real Estate Deals with Jay Conner
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.
What You'll Learn• 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 conversationCHAPTERS[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 JayJay 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.
Connect With Jay ConnerLearn 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
Want to Share Your Side of the Story?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
35 min - From IT to Multifamily Real Estate: How Hugo Macau Is Scaling His Portfolio!
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.
What You’ll Learn• 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 moveChapters[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 MacauFor 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
22 min - How Investors Use HELOCs to Buy More Real Estate with Benjamin Stef
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 You'll Learn- 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
Key Highlights- 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
Connect with Benjamin StefWebsite: https://www.fundingfreedom.net/
Youtube: https://www.youtube.com/@UCYZIjA6JcV0DqLD-1q2iZbQ
Connect with Us:
- Skool Community
- Website
- Facebook
- Instagram
- LinkedIn
- YouTube
Support the Show: Enjoy our content? Share with your family and friends and anyone who will benefit with the insight we shared today. Leave us a review on your preferred platform to help us grow or any suggestion.
Join Our Community: Become a part of our exclusive Skool community, Capital Raising Mastery Hub. Get valuable resources, engage in discussions, and receive support for real estate entrepreneurs. Join Now! We are live!
Contact Us: For inquiries, guest appearances, or sponsorship opportunities, contact us at [email protected].
29 min - Real Estate Syndication, Capital Raising, and the Truth About Multifamily Investing
Real estate investing looks simple online but what happens when you actually start raising capital, managing investor expectations, and underwriting multifamily deals?
In this episode of When Real Estate Gets Real, Stephen Lee Thomas sits down with Ray Woods, a real estate investor, engineer, cybersecurity professional, and entrepreneur building across wholesaling, Airbnb, multifamily, and real estate technology.
Ray shares how his first wholesale deal changed the way he looked at money, why reinvesting into the business mattered, and what investors often misunderstand about scaling into multifamily syndication.
This conversation also gets into the responsibility of managing investor capital, why communication matters when deals go wrong, and how Ray is building a syndication app to help investors underwrite deals more clearly.
What You’ll Learn:
- How Ray moved from engineering into real estate investing
- What he learned from his first wholesale checks
- Why managing money is different from earning money
- What changes when you start raising investor capital
- Why communication protects credibility in tough deals
- How better underwriting can help syndicators avoid bad deals
- Why patience matters in multifamily investing
Connect with Ray:
Website: https://tinyurl.com/rewithray
Instagram: https://www.instagram.com/realestatewithrayy/
YouTube: https://www.youtube.com/@RealEstateWithRay?sub_confirmation=1
TikTok: https://www.tiktok.com/@realestatewithray
Connect with Us:
- Skool Community
- Website
- Facebook
- Instagram
- LinkedIn
- YouTube
Support the Show: Enjoy our content? Share with your family and friends and anyone who will benefit with the insight we shared today. Leave us a review on your preferred platform to help us grow or any suggestion.
Join Our Community: Become a part of our exclusive Skool community, Capital Raising Mastery Hub. Get valuable resources, engage in discussions, and receive support for real estate entrepreneurs. Join Now! We are live!
Contact Us: For inquiries, guest appearances, or sponsorship opportunities, contact us at [email protected].
30 min - From Millionaire to Starting Over: Real Estate Lessons That Actually Matter
What happens when you make millions early… then lose almost everything?
In this episode of When Real Estate Gets Real, Stephen Lee Thomas sits down with Lawrence Dunning former MMA fighter turned real estate broker, investor, and developer who shares his raw, unfiltered journey through success, failure, and rebuilding.
From trading floors in Chicago to losing money in the 2009 crash… to navigating bad partnerships and lawsuits… Lawrence breaks down the real lessons most people never talk about.
This episode goes beyond tactics it’s about resilience, identity, and finding your place in real estate.
What You’ll Learn:
- Why early success can actually set you up for failure
- How to find your niche in real estate (and why it takes time)
- The biggest mistakes new investors make
- How to evaluate partnerships the right way
- Why hardship makes you better in business and life
Key Highlights:
- Transitioning from trading to real estate
- Losing money and rebuilding from scratch
- Lessons from a failed development partnership
- The importance of intuition in business decisions
- How real estate development transforms communities
Guest: Lawrence Dunning
Broker | Investor | Developer | Former MMA FighterWays to connect with Lawrence Dunning
LinkedIn: https://www.linkedin.com/in/lawrence-dunning-mba-2b97a120
Instagram: https://www.instagram.com/lawrencedunning
Webiste: https://enterthelionheart.com
Connect with Us:
- Skool Community
- Website
- Facebook
- Instagram
- LinkedIn
- YouTube
Support the Show: Enjoy our content? Share with your family and friends and anyone who will benefit with the insight we shared today. Leave us a review on your preferred platform to help us grow or any suggestion.
Join Our Community: Become a part of our exclusive Skool community, Capital Raising Mastery Hub. Get valuable resources, engage in discussions, and receive support for real estate entrepreneurs. Join Now! We are live!
Contact Us: For inquiries, guest appearances, or sponsorship opportunities, contact us at [email protected].
28 min - What Multifamily Investors Need to Know About Debt and Capital Raising
Commercial real estate has changed dramatically over the last few years but is today’s market really like 2008?
In this episode of When Real Estate Gets Real, Stephen Lee Thomas sits down with Jacob Clopton, founder and president of Clopton Capital, to unpack what’s happening in commercial real estate financing, debt markets, insurance, solar, capital raising, and multifamily syndication.
Jacob shares why today’s challenges are less about a lack of liquidity and more about leverage, interest rates, and cost of capital. He also explains what early-stage syndicators should understand about raising capital, building a team, and avoiding the trap of trying to do everything alone.
What You’ll Learn:
- How today’s market compares to 2008
- Why many multifamily deals are struggling despite strong occupancy
- What commercial real estate debt looks like right now
- How Clopton Capital supports investors across financing, insurance, sourcing, solar, and 1031 services
- Why first-time syndicators should focus on direct investor relationships
- The importance of delegation when scaling a real estate business
Connect with Jacob:
Website: https://cloptoncapital.com/
LinkedIn: https://www.linkedin.com/in/jakeclopton1
Youtube: www.youtube.com/@cloptoncapital3417
Connect with Us:
- Skool Community
- Website
- Facebook
- Instagram
- LinkedIn
- YouTube
Support the Show: Enjoy our content? Share with your family and friends and anyone who will benefit with the insight we shared today. Leave us a review on your preferred platform to help us grow or any suggestion.
Join Our Community: Become a part of our exclusive Skool community, Capital Raising Mastery Hub. Get valuable resources, engage in discussions, and receive support for real estate entrepreneurs. Join Now! We are live!
Contact Us: For inquiries, guest appearances, or sponsorship opportunities, contact us at [email protected].
24 min - From House Hack to Multifamily: Why Scaling Alone Doesn’t Work
Most real estate investors start the same way solo, figuring it out, and trying to scale on their own.
But what happens when that model stops working?
In this episode, Stephen sits down with Jared Mickley, a Marine Corps helicopter pilot and multifamily asset manager, to break down his journey from house hacking and short-term rentals to stepping into multifamily investing.
This conversation goes beyond tactics it dives into the real shift that happens when you stop treating real estate like a side hustle and start running it like a business.
What You’ll Learn:- Why single-family investing hits a scaling ceiling
- The real reason multifamily is a team sport
- The 4 key roles in a multifamily deal
- What makes capital raising actually work
- The difference between investor interest and commitment
- Why consistency beats speed in real estate
Key Highlights:- Transitioning from VA loan house hack to STR and midterm rentals
- Lessons learned managing rentals remotely during deployment
- How military teamwork translates into real estate success
- Inside a real multifamily team structure
- The mindset shift that changes everything
Connect with Jared:
Website: https://www.glidepathinvestments.com/team/jared-mickley
LinkedIn: linkedin.com/in/jared-mickley-b4008114a
Email: [email protected]
Connect with Us:
- Skool Community
- Website
- Facebook
- Instagram
- LinkedIn
- YouTube
Support the Show: Enjoy our content? Share with your family and friends and anyone who will benefit with the insight we shared today. Leave us a review on your preferred platform to help us grow or any suggestion.
Join Our Community: Become a part of our exclusive Skool community, Capital Raising Mastery Hub. Get valuable resources, engage in discussions, and receive support for real estate entrepreneurs. Join Now! We are live!
Contact Us: For inquiries, guest appearances, or sponsorship opportunities, contact us at [email protected].
16 min - The Truth About Real Estate Partnerships, Failure, and Finding Your Lane
What happens when corporate “security” disappears overnight?
In this episode, Stephen Lee Thomas sits down with Mike Deaton, co-founder of Flipping Dirt, to break down his journey from being laid off at Microsoft to building a land flipping business with over 700 deals completed.
Mike shares how he and his wife pivoted into entrepreneurship, why land investing became their focus, and the lessons they learned the hard way through partnerships.
What You’ll Learn:
- How land flipping works as a business model
- Why your first deal is about confidence—not income
- The hidden risks of real estate partnerships
- How to think about failure as an entrepreneur
- Why deal flow matters more than perfection
Key Highlights:
- From dual layoffs to full-time entrepreneurship
- First land deal: $3K → $10K flip
- Why land offers more control than multifamily
- Lessons from deals that went underwater during COVID
- Building a business that fits your lifestyle
Connect with Mike: Website: https://flippingdirt.us/freedom
Facebook: https://www.facebook.com/mikeandligia
LinkedIn: https://www.linkedin.com/company/flipping-dirt
Connect with Us:
- Skool Community
- Website
- Facebook
- Instagram
- LinkedIn
- YouTube
Support the Show: Enjoy our content? Share with your family and friends and anyone who will benefit with the insight we shared today. Leave us a review on your preferred platform to help us grow or any suggestion.
Join Our Community: Become a part of our exclusive Skool community, Capital Raising Mastery Hub. Get valuable resources, engage in discussions, and receive support for real estate entrepreneurs. Join Now! We are live!
Contact Us: For inquiries, guest appearances, or sponsorship opportunities, contact us at [email protected].
26 min - How to Find Your Real Estate Superpower with Will Harvey
What happens when you realize you like real estate — but not the part everyone assumes you should be doing?
In this episode of When Real Estate Gets Real, Stephen Lee Thomas talks with Will Harvey of Harvey Capital about his path from mortgage lending to flipping houses, passive investing, and eventually building a hard money lending business.
Will shares how he discovered that operations were not his strength — and that the finance side of real estate was where he truly belonged. The conversation digs into what changes when you begin managing investor capital, how to separate decision quality from outcomes, and why protecting capital matters more than chasing growth.
This is a valuable episode for operators who are still figuring out where they fit, as well as investors trying to better understand what makes a disciplined capital partner.
What You’ll Learn:
- How Will Harvey transitioned from house flips to hard money lending
- Why not every real estate investor should be an operator
- What changes when you start managing other people’s money
- How to think about good decisions vs bad outcomes
- Why protecting capital matters before scaling
- What most people misunderstand about raising capital
- How to identify your real estate superpower
Key Highlights:
- From mortgage business to real estate investing
- Why Will exited landlording and leaned into finance
- Lessons from a wedding venue deal that did not go to plan
- Building discipline as a fiduciary
- Scaling a lending business through a fund structure
- Why raising capital takes long-term relationship building
- The importance of staying in your lane and adding value
Connect with Will Harvey:
Website: harvey-capital.comEmail: Skool Community- Website
- Facebook
- Instagram
- LinkedIn
- YouTube
Support the Show: Enjoy our content? Share with your family and friends and anyone who will benefit with the insight we shared today. Leave us a review on your preferred platform to help us grow or any suggestion.
Join Our Community: Become a part of our exclusive Skool community, Capital Raising Mastery Hub. Get valuable resources, engage in discussions, and receive support for real estate entrepreneurs. Join Now! We are live!
Contact Us: For inquiries, guest appearances, or sponsorship opportunities, contact us at [email protected].
35 min - What Really Happens After Your First Real Estate Deal
In this episode of When Real Estate Gets Real, Stephen Lee Thomas sits down with John Todderud of Cardinal Oak Investments to unpack the reality behind multifamily investing once the deal is done.
From managing tenants and operations to navigating investor expectations and market headwinds, this conversation reveals what most new operators aren’t prepared for.
John shares lessons from completing 9 deals, including the shift in responsibility when handling investor capital, the challenges of raising trust (not just money), and how today’s market is creating new opportunities for those paying attention.
What You’ll Learn:- What changes after closing your first deal
- The biggest operational surprises in multifamily
- How investor responsibility shifts decision-making
- Why trust is the hardest part of raising capital
- How interest rates and lending impact deals
- Why today’s market may offer strong buying opportunities
Key Highlights:- The difference between solo deals vs syndications
- Real challenges with bridge loans and cash flow
- Why investors shouldn’t make every decision
- The role of education in capital raising
- Leveraging your network when things get difficult
Connect with John:
Email: [email protected]Webiste: https://cardinaloak.com/Connect with Us:
- Skool Community
- Website
- Facebook
- Instagram
- LinkedIn
- YouTube
Support the Show: Enjoy our content? Share with your family and friends and anyone who will benefit with the insight we shared today. Leave us a review on your preferred platform to help us grow or any suggestion.
Join Our Community: Become a part of our exclusive Skool community, Capital Raising Mastery Hub. Get valuable resources, engage in discussions, and receive support for real estate entrepreneurs. Join Now! We are live!
Contact Us: For inquiries, guest appearances, or sponsorship opportunities, contact us at [email protected].
29 min
About When Real Estate Gets Real
From the publisher's feed
When Real Estate Gets Real is a behind-the-scenes podcast for real estate operators who’ve already closed a deal and discovered that the spreadsheets weren’t the hard part.
Hosted by Stephen Lee-Thomas, the show explores what actually changes after the first close when real money, real investors, and real pressure enter the picture.
Each episode goes beyond tactics to unpack the decisions, mistakes, leadership challenges, and personal growth that define the shift from “I did a deal” to “I’m a real operator now.”
This podcast is for operators past their first close who want truth over hype, clarity over noise, and systems that support long-term scale.