When Real Estate Gets Real

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 [https://tinyurl.com/rewithray] Instagram: https://www.instagram.com/realestatewithrayy/ [https://www.instagram.com/realestatewithrayy/] YouTube: https://www.youtube.com/@RealEstateWithRay?sub_confirmation=1 [https://www.youtube.com/@RealEstateWithRay?sub_confirmation=1] TikTok: https://www.tiktok.com/@realestatewithray [https://www.tiktok.com/@realestatewithray]   Connect with Us: * Skool Community [https://www.skool.com/multifamilymasteryhub/about] * Website [https://raisegenius.ai/] * Facebook [https://www.facebook.com/raisegeniusAi] * Instagram [https://www.instagram.com/stephenleethomas/] * LinkedIn [https://www.linkedin.com/in/raisegeniusai/] * YouTube [https://www.youtube.com/@CapitalRaisersPlaybook] 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 [https://www.skool.com/multifamilymasteryhub]! We are live! Contact Us: For inquiries, guest appearances, or sponsorship opportunities, contact us at info@raisegenius.ai.

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 Fighter   Ways to connect with Lawrence Dunning LinkedIn: https://www.linkedin.com/in/lawrence-dunning-mba-2b97a120 [https://www.linkedin.com/in/lawrence-dunning-mba-2b97a120] Instagram: https://www.instagram.com/lawrencedunning [https://www.instagram.com/lawrencedunning] Webiste: https://enterthelionheart.com [https://enterthelionheart.com]   Connect with Us: * Skool Community [https://www.skool.com/multifamilymasteryhub/about] * Website [https://raisegenius.ai/] * Facebook [https://www.facebook.com/raisegeniusAi] * Instagram [https://www.instagram.com/stephenleethomas/] * LinkedIn [https://www.linkedin.com/in/raisegeniusai/] * YouTube [https://www.youtube.com/@CapitalRaisersPlaybook] 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 [https://www.skool.com/multifamilymasteryhub]! We are live! Contact Us: For inquiries, guest appearances, or sponsorship opportunities, contact us at info@raisegenius.ai.

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/ [https://cloptoncapital.com/] LinkedIn: https://www.linkedin.com/in/jakeclopton1 [https://www.linkedin.com/in/jakeclopton1] Youtube: www.youtube.com/@cloptoncapital3417 [http://www.youtube.com/@cloptoncapital3417]   Connect with Us: * Skool Community [https://www.skool.com/multifamilymasteryhub/about] * Website [https://raisegenius.ai/] * Facebook [https://www.facebook.com/raisegeniusAi] * Instagram [https://www.instagram.com/stephenleethomas/] * LinkedIn [https://www.linkedin.com/in/raisegeniusai/] * YouTube [https://www.youtube.com/@CapitalRaisersPlaybook] 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 [https://www.skool.com/multifamilymasteryhub]! We are live! Contact Us: For inquiries, guest appearances, or sponsorship opportunities, contact us at info@raisegenius.ai.

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 [https://www.glidepathinvestments.com/team/jared-mickley] LinkedIn: linkedin.com/in/jared-mickley-b4008114a [linkedin.com/in/jared-mickley-b4008114a] Email: jared@glidepathinvestments.com [jared@glidepathinvestments.com]   Connect with Us: * Skool Community [https://www.skool.com/multifamilymasteryhub/about] * Website [https://raisegenius.ai/] * Facebook [https://www.facebook.com/raisegeniusAi] * Instagram [https://www.instagram.com/stephenleethomas/] * LinkedIn [https://www.linkedin.com/in/raisegeniusai/] * YouTube [https://www.youtube.com/@CapitalRaisersPlaybook] 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 [https://www.skool.com/multifamilymasteryhub]! We are live! Contact Us: For inquiries, guest appearances, or sponsorship opportunities, contact us at info@raisegenius.ai [info@raisegenius.ai].

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 [https://flippingdirt.us/freedom] Facebook: https://www.facebook.com/mikeandligia [https://www.facebook.com/mikeandligia] LinkedIn: https://www.linkedin.com/company/flipping-dirt [https://www.linkedin.com/company/flipping-dirt]   Connect with Us: * Skool Community [https://www.skool.com/multifamilymasteryhub/about] * Website [https://raisegenius.ai/] * Facebook [https://www.facebook.com/raisegeniusAi] * Instagram [https://www.instagram.com/stephenleethomas/] * LinkedIn [https://www.linkedin.com/in/raisegeniusai/] * YouTube [https://www.youtube.com/@CapitalRaisersPlaybook] 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 [https://www.skool.com/multifamilymasteryhub]! We are live! Contact Us: For inquiries, guest appearances, or sponsorship opportunities, contact us at info@raisegenius.ai.