Grateful Dead, AI in Mortgages, and Surviving the Market Shift

Lending Leadership

Welcome back to Lending Leadership: The Mortgage Pros—your front-row seat to candid conversations about the ever-evolving mortgage industry.

On today’s episode, we decided to kick back, relax, and embrace a looser format. With Tom out and just the two of us, Robert Fillyaw and Dave Holland, at the helm, we traded structure for a little “chewing the fat.” From Vegas trips and Grateful Dead concerts to AI’s impact on mortgages and the existential debate over one gorilla versus a hundred men, no topic was off-limits.

We took a deep dive into how AI is changing the way we work (and parent), the industry’s consolidation, and even made bold predictions for the next football season. If you're looking for a heavily scripted mortgage masterclass, you might want to skip ahead—today is all about real talk and laughs between two industry veterans.

Key takeaways:

1. No Topic Is Too Off the Wall When You’re Among Friends: Sometimes, the best insights come when you loosen up the format. From Las Vegas trip stories to viral internet debates, unstructured conversations can spark fresh perspectives and authentic laughs—essential for creating meaningful connections in any business.
2. AI Is Reshaping Both Our Industry and Daily Life: We explored how AI is influencing loan origination processes, underwriting, and even our email communications. While it won’t replace the human touch, embracing AI is becoming non-negotiable for mortgage professionals who want to stay relevant and efficient.
3. Critical Thinking Still Matters—Especially for the Next Generation: Our banter about using AI in schoolwork led us to reflect on the value of developing independent problem-solving skills. AI is a powerful tool, but it shouldn’t become a crutch that stunts intellectual growth, especially for the next generation of leaders.
4. Consolidation Is Accelerating, and Adaptability Reigns Supreme: The mortgage industry’s long restructuring period is forcing weaker players and less-adaptive LOs out. Those who focus on relationships, technology, and advisory roles will thrive, while others will get left behind as fewer originators handle more business.
5. Diversification, Fun, and Connection Matter Too: Whether you’re debating football schedules, planning Napa wine tours, or joking about flat-earthers at a Dead show, making room for camaraderie and personal connection can help sustain morale and creativity in a tough market.

Thanks for joining us for this no-holds-barred episode of Lending Leadership: The Mortgage Pros. If you’re feeling lost in the mortgage maze or just want to chat business, leadership, and strategy—drop us a line. No pressure, no expectations, just good conversation.

Don’t forget to hit subscribe and leave us that five-star review—we appreciate every single one.

Until next time, this is Robert and Dave, reminding you: the only constant in mortgages—and life—is change. Stay curious, stay connected, and keep leading.

Robert, Tom, & Dave