S2 E41 | Hard Money, Hard Lessons with Caleb Delgado

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What happens when life knocks you down not once, but twice—and you find the strength to build something even better than before?
Caleb's journey from Queens-born soccer player to mortgage mogul to nearly bankrupt and back again is a masterclass in resilience and entrepreneurial spirit. Growing up in Long Island with immigrant parents, he learned early lessons contrasting wealth and struggle that would prove invaluable later in life.
His soccer skills earned him a D1 college spot playing center midfield, but family financial troubles forced him to leave school and enter the mortgage industry at just 20. The timing couldn't have been more dramatic—the early 2000s "Boiler Room" era of mortgage lending. Within months, Caleb was making hundreds of thousands, driving luxury cars, dropping $10,000 on dinner tabs, and living what seemed like the dream. Until 2008 hit.
"That crash was my saving grace," Caleb reveals, explaining how losing everything forced him to rebuild with better values. With savings his mother had secretly set aside from his earnings, he relocated to Florida. Starting over meant taking jobs beneath his experience level while strategically networking and positioning himself for his next chapter.
The founding of DKC Lending with his partner David marks the culmination of these hard-learned lessons. Their approach to hard money lending focuses on transparency, reliability, and truly serving clients rather than simply collecting interest. Even in today's challenging market, they're finding creative solutions for investors while maintaining their core values.
What makes this conversation so compelling is Caleb's candor about both success and failure. His counterintuitive belief that "business is personal" challenges conventional wisdom, while his insights on entrepreneurship—"stick to what you know and be the best at it"—offer practical guidance for anyone building a career or company.
Want to build something that survives market crashes and personal setbacks? Listen now to learn how your biggest failures might become your greatest teachers.

Chapters

1. Introduction to Caleb and DKC Lending (00:00:00)

2. Growing Up in New York (00:02:30)

3. Soccer Career to Early Business Life (00:10:42)

4. From Making Millions to Losing Everything (00:18:37)

5. Moving to Florida and Starting Over (00:31:32)

6. Building DKC Lending with David (00:44:32)

7. Investment Philosophy in Today's Market (00:54:30)

8. Handling Deals and Foreclosures (01:02:45)

9. Final Thoughts and Finding Success (01:07:18)