In this episode of The Journey, Leo talks with Caleb Christopher, founder of Creative TC and DOSGuard. Caleb is a former corrections officer and cybersecurity specialist who now handles more than 50 creative finance transactions a month. He applies engineering-level thinking and risk management to real estate, operations, and systems that scale.
Most people think creative finance is shady or guru-driven. Caleb treats it as a risk problem that needs structure, incentives, and ethics. He built a remote first operations company using talent in South Africa, created an insurance product for due on sale risk, and developed TABLE, a values-based operating system for his team.
This episode is packed with insights on entrepreneurship, stress, partnerships, culture, hiring, risk, and building companies that last.
What You Will Learn
How Caleb went from corrections officer to IT to cybersecurity to creative finance
The accidental landlord story that started everything
Why creative finance is a risk management discipline
How he built a remote first team in South Africa
The near bankruptcy moment that changed his leadership
How TABLE values guide every decision
How to hire for judgment
Why founders need to say no
How he launched a title company built for scale
Why AI amplifies both good and bad decisions
Timestamps
00:00 Intro01:00 Real estate marketing hot takes02:00 Toxic positivity and guru culture03:20 Career path to risk management04:30 Discovering real estate and creative finance08:30 Building Creative TC10:30 Why he avoids hiring from mentorship groups11:20 Reputation and protecting your name12:00 The stress of payroll and uncertainty13:30 High judgment employees16:20 Strong opinions and attracting the right people17:10 Learning to say no18:00 Founder brain vs team stability20:40 Compensation, structure, culture22:00 The TABLE values24:50 Adopting AI responsibly26:10 Raising capital27:20 Why title companies are underrated31:20 Partnership experiences38:00 Key man insurance40:00 Ethical dealmaking42:50 Connect with Caleb45:00 The question he wants every founder to ask
One Smart Move Before You Dive Into Creative Finance
If you are exploring creative finance, raising capital, or building a business with real risk involved, do not guess. Visit my site to learn practical frameworks for evaluating deals, managing risk, and protecting your investors.
Connect with Caleb
Learn more at calebchristopher.io and follow @fcalebchristopher on Instagram and Facebook.
Website: calebchristopher.ioInstagram: instagram.com/fcalebchristopherFacebook: facebook.com/FCalebChristopher
Connect with Leo
LinkedIn: linkedin.com/in/leo-youngInstagram: instagram.com/leoyoungrealestateInvest with us: tidycal.com/leoyoungrealestate/investor-alignment-call
Disclaimer
This podcast is for educational purposes only. It is not financial, legal, or tax advice. Consult licensed professionals before making decisions.
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