When Real Estate Gets Real

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: Email: Jared@gladpathinvestments.com [Jared@gladpathinvestments.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.

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.com Email: 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 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: john@cardinaloak.com Webiste: https://cardinaloak.com/ [https://cardinaloak.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 Keeps Commercial Real Estate Deals Alive in a Down Market?

What actually keeps a commercial real estate deal alive when the market turns against you? In this episode of When Real Estate Gets Real, Stephen Lee Thomas sits down with Will Curtis, a commercial real estate broker out of San Antonio who has been involved in more than $1 billion in transactions and is known as the “Property Operations Whisperer.” This conversation goes beyond surface-level real estate advice and gets into the real drivers of long-term success: disciplined underwriting, smart leverage, operational awareness, and the kind of leadership that only comes from experience. Will also shares how his military background shaped his perspective, what he learned from watching seasoned investors survive past crashes, and why he hopes to eventually create a real estate fund for veterans. What You'll Learn * Why debt and leverage management matter in every market cycle * What operators can and cannot fix through property operations * How the office market changed after COVID * Why San Antonio has performed differently than Austin * Leadership lessons from commercial real estate and the military * The importance of humility, team building, and learning from mistakes Key Highlights: * Why managing leverage is the #1 factor in surviving real estate downturns * Lessons from investors who survived the 2008 financial crisis * The real impact of COVID on the office real estate market * Why San Antonio outperformed other major Texas markets like Austin * The importance of buying right—before operations even begin * How experienced operators stay competitive during market declines * Emerging trends like flexible office and third-space environments * The concept of the “labor leverage ratio” and what it reveals about office demand * Leadership lessons from both military and commercial real estate experience * Why humility and team-building are critical for long-term success Ways to connect with Will Curtis Website: https://www.vetsinrealestate.com/ LinkedIn: https://www.linkedin.com/in/willcurtisccim/ Facebook: https://www.facebook.com/willcurtisccim/ Instagram: https://www.instagram.com/willcurtisccim/ Youtube: www.youtube.com/@vetsinre   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.