Are you truly protecting yourself when you take over someone’s mortgage? Are your disclosures clear? Is your paperwork defensible? And if a lender enforced the due-on-sale clause tomorrow, would your deal survive?

In this fan-favorite replay of the REI Freedom Podcast, host Jeremy Beland sits down with creative finance expert Caleb Christopher to break down what most investors misunderstand about subject-to transactions.

Sub-to deals can be powerful wealth-building tools. But when structured improperly, they can expose investors to legal risk, damaged reputations, and long-term financial consequences. Caleb pulls back the curtain on the most common mistakes investors make and explains how to structure creative financing deals the right way safely, legally, and ethically.

Caleb Christopher is the founder of Creative TC, DOS Guard, and Creative Title. After becoming an accidental landlord and discovering creative finance through Rich Dad Poor Dad, Caleb recognized a dangerous gap in the industry: plenty of education on getting deals, but very little guidance on closing them correctly.

In this episode, he shares practical strategies for evaluating sub-to opportunities, protecting sellers, mitigating due-on-sale risk, and building a professional team that ensures your deals hold up long-term.

Key Topics Covered

• How Caleb transitioned from accidental landlord to creative finance specialist
• What makes a strong sub-to candidate, including equity position and seller flexibility
• Red flags investors should avoid, especially negative equity and future mortgage plans
• The dangers of “naked sub-to” deals without proper documentation
• Why full transparency and early disclosures protect both parties
• How balloon payments can severely restrict exit strategies
• Understanding the due-on-sale clause and how lenders enforce it
• Why maintaining a positive seller relationship is critical post-closing
• Building a team that understands complex creative transactions

The Reality of the Due-On-Sale Clause

The due-on-sale clause is not theoretical. It can be enforced. Certain lenders are more aggressive than others, and when it happens, investors without a plan can find themselves in serious trouble.

Caleb explains how proper structuring, seller communication, and services like DOS Guard can provide peace of mind and reduce exposure. The goal is not to avoid risk entirely, but to manage it responsibly.

Common Investor Mistakes

• Taking over payments without proper legal documentation
• Failing to understand the seller’s long-term housing goals
• Disclosing risks too late in the process
• Structuring deals that limit resale options
• Operating without experienced transaction and legal support

Creative finance requires uncommon competence. Without it, you risk becoming the case study no one wants to be.

Connect with Caleb Christopher

Instagram: @fcalebchristopher
Creative TC: creative-tc.io

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This replay episode is packed with real-world lessons for investors, operators, and entrepreneurs who want to combine freedom, impact, and profitability.

Subscribe, rate, and review the REI Freedom Podcast to stay connected with stories and strategies that help you build a life of freedom through real estate.

Fan-Favorite Replay

What if your next real estate move did not require relocating, quitting everything, or waiting for “perfect timing”? What if building an international business was less about luck and more about systems, leadership, and personal growth? And what if your biggest breakthrough came from thinking bigger than your comfort zone?

In this fan-favorite replay of the REI Freedom Podcast, host Jeremy Beland sits down with Ian Lobas, a real estate investor, coach, and international short-term rental operator who built a thriving hospitality business in St. Martin, all while managing it remotely from Baltimore.

Ian shares how he turned a bold vision into a fully integrated short-term rental operation with over 60 units in less than a year. From marketing and interior design to concierge services and construction, he reveals how building strong systems and the right team made international scaling possible.

Ian Lobas went from running a high-performing real estate business in the U.S. to launching a full-service Airbnb and hospitality company in the Caribbean. Rather than relying on hype or shortcuts, he focused on operational excellence, personal development, and uncompromising standards.

In this episode, Ian breaks down how he navigated market failures, cultural differences, and infrastructure challenges to build a predictable, high-performing operation in one of the most competitive tourism markets in the region.

About Ian Lobas
Ian Lobas is a real estate investor, coach, and fractional CEO and COO. After experiencing burnout as a top-producing agent, he shifted his focus toward building sustainable businesses rooted in systems, leadership, and personal growth. Today, he leads both a coaching company and a growing international short-term rental operation in St. Martin.

Key Takeaways from This Episode

-How Ian’s background in international shipping and sales shaped his business mindset.

-Why personal development became the foundation of his success.

-The turning point that led him from traditional real estate into coaching.

-Why St. Martin became the ideal market for his hospitality vision.

-How he built a trusted local team and scalable leadership structure.

-The importance of process-driven operations in hospitality.

-How multiple service verticals strengthened his business model.

-Why reputation matters more in small international markets.

-How Ian scaled to 60-plus units in under a year.

Connect with Ian Lobas
Interested in collaborating, investing, or learning more about international short-term rentals?
Email: ian@covecasa.co


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This replay episode is packed with real-world lessons for investors, operators, and entrepreneurs who want to combine freedom, impact, and profitability.

Subscribe, rate, and review the REI Freedom Podcast to stay connected with stories and strategies that help you build a life of freedom through real estate.

Fan-Favorite Replay

Is it really possible to build long-term wealth in real estate without being stuck on the transactional hamster wheel? Can you create consistent income without managing tenants, toilets, and endless repairs? And what does it take to walk away from corporate life and design a business around freedom instead of stress?

In this fan-favorite replay of the REI Freedom Podcast, host Jeremy Beland sits down with Alex Pardo to revisit his journey from corporate finance to self-storage investing. Alex shares how one early deal changed his trajectory, why he pivoted away from wholesaling, and how self-storage became the foundation of his semi-passive real estate portfolio.

From navigating early losses to building systems that support long-term growth, Alex offers a transparent look at what it really takes to succeed in commercial real estate.

Meet Alex Pardo

Alex Pardo is a self-storage investor, entrepreneur, and coach with nearly two decades of experience in real estate. After leaving his position at General Electric, he built a successful investing business through wholesaling, fix-and-flips, and eventually self-storage acquisitions. Today, Alex owns and operates multiple storage facilities and helps investors transition into commercial real estate through his coaching programs.

What You’ll Learn in This Episode

• Why Alex chose to leave corporate America and pursue real estate full-time
• How one early short sale helped build confidence and momentum
• The role of coaching and mentorship in avoiding costly mistakes
• Why Alex shifted from wholesaling to self-storage in 2019
• The advantages of storage facilities over traditional rentals
• How to find off-market self-storage deals in secondary and rural markets
• Strategies for working with retiring mom-and-pop owners
• How Alex structures deals using seller financing, private money, and partnerships
• Why you do not need large amounts of personal capital to get started
• How mindset and consistency drive long-term success

Alex’s Coaching and Resources

Alex offers a hands-on coaching program designed to help investors acquire their first storage facility within six to twelve months. His approach focuses on education, execution, and sustainable growth.

Apply here: storagewins.com/apply
YouTube: youtube.com/alexpardo

If Alex’s story inspired you and you’re ready to create more time and financial freedom through real estate, book a discovery call with Jeremy and the REI Freedom team at:

reifreedom.com/apply

If you enjoyed this replay episode, please subscribe, rate, and review the REI Freedom Podcast, and share it with someone ready to build wealth the right way.