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When Creative Finance Actually Makes Sense and When It Doesn’t ft. Caleb Christopher

Hey, it’s Jordan Samuel Fleming — welcome back to That Real Estate Tech Guy! In this episode, I’m joined by Caleb Christopher, founder of Creative TC, a consulting company built to make creative finance deals safe, legal, ethical, and clearly understood by everyone involved.

This is one of the most grounded and practical conversations I’ve had about creative finance. Caleb breaks down exactly when strategies like subject-to actually make sense, when they absolutely don’t, and why most investors misunderstand what these deals really are. We walk through real stories, real numbers, and real…

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