How to Do More Creative Deals with Caleb Christopher, Ep. 765

Caleb Christopher is a real estate investor, entrepreneur, and one of the foremost minds in creative financing for residential properties. He’s the founder of Creative TC, a consulting firm helping investors structure safe, legal, and ethical creative finance deals—including subject-to, seller finance, and wrap mortgages. He’s also the creator of tools like the underwriting calculator and the partnership evaluator, and he’s raising capital for ventures like his title company via innovative vehicles such as investment clubs. Caleb is passionate about building tools where none exist, solving complex problems, and creating upward mobility for the people around him.

Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.

Key Takeaways

• Always start creative deal conversations with the end in mind—even if the path is uncertain

• Get the seller’s full story before pitching terms; relationship-building is critical

• Flexibility and an outcomes-oriented mindset are essential for creative structures

• Investment clubs can be a powerful capital-raising alternative to traditional syndications

• Solving the seller’s future needs is often more important than hitting your own price targets

Topics

From Builder to Problem-Solver

• Caleb builds systems and solutions when existing tools don’t meet his standards

• Created Creative TC to become an authority in ethical creative deal structures

Creative Finance 101

• Most deals start with a pricing mismatch—terms become the bridge

• Key is understanding the seller’s backstory and aligning on a shared outcome

Being Outcomes-Oriented

• Investors must learn to zoom out and focus on results, not just checklist tasks

• Knowing multiple exit strategies allows for creative flexibility

Common Seller Profiles

• Single-family deals often involve financial distress

• High-price sellers may not be distressed but hold strong pricing expectations

Structuring for Mutual Success

• Price vs. terms: the seller gets one, you get the other

• Options like cash-out timelines, exit plans, and shared management responsibilities help mitigate seller risk

Challenges with Brokers

• Brokers often limit creative structures—direct seller conversations are more fruitful

• Investors must proactively communicate how brokers still get paid on creative deals

Raising Capital Legally

• Differentiates between syndication types (506b, 506c) and investment clubs

• Advocates for active participation structures and tools like Fractional to stay compliant

Investor Mindset and Scaling

• Many investors forget to consider the seller’s needs—this kills deals

• Demonstrating good faith and offering safeguards builds trust and credibility

Lead Flow and Brand Positioning

• Caleb’s unique positioning in creative finance draws complex deals his way

• Word-of-mouth and online presence help others know “this is the guy for creative”

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Round of Insights

Failure that set Caleb up for success: Company nearly went bankrupt due to cash mismanagement and market shifts. Came out stronger and more selective about partnerships—only works with people who’ve been through tough situations and grown from them.

Digital or mobile resource: His own Partnership Evaluator worksheet that helps partners assess each other before starting a business or investment deal.

Book recommendation: Made to Stick by Chip and Dan Heath

Daily habit: Reads the Bible every morning, writes down intrusive thoughts on a checklist to stay focused, and sends a daily briefing to his team.

#1 insight for structuring creative deals: Start with a cash offer. Then get the seller’s full story—only then can you structure something that works.

Favorite restaurant in Kansas: Joe’s KC.

Next Steps

• Connect with Caleb at calebchristopher.io

• Sign up for his newsletter to access his real numbers, case studies, and behind-the-scenes operations

• Explore his creative finance consulting and capital-raising strategies

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