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 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

• 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/

Listen now and book your spot to be our next guest: https://whenrealestategetsreal.com/podcast-booking

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

Listen now and book your spot to be our next guest: https://whenrealestategetsreal.com/podcast-booking

Multifamily investing isn’t what most people think.

In this episode, Stephen Lee Thomas sits down with William Liu, a multifamily syndicator and former CMO, to break down what really happens when you step into the role of an operator.

From raising capital to managing investor expectations and navigating real-world challenges, this conversation uncovers the realities behind the business of multifamily investing.

What You'll Learn

• Why multifamily is more like running a business than investing
• The truth about capital raising timelines
• How to build investor relationships the right way
• What happens when occupancy drops unexpectedly
• The importance of cash flow and financial management
• Lessons from transitioning out of a W2 career

Key Highlights:

• Capital raising is marketing + sales
• Relationships must be built before deals
• Cash flow pressures are real for operators
• Property management requires leadership, not just oversight
• Investor communication is critical to long-term success

Ways to connect with William Liu

LinkedIn : linkedin.com/in/willliuh Website: https://www.giverisecapital.com

Listen now and book your spot to be our next guest: https://whenrealestategetsreal.com/podcast-booking