Built Between Bedtimes – Episode 15: The $500K Windshield, the Psychology of Debt, and Why People Buy Houses With Their Emotions

Built Between Bedtimes · Jun 19, 2026 · 45m

In this episode, Dylan recaps the wildest golf story of the year — slicing a drive into a moving truck, tracking down the driver, and footing the bill on a Silverado windshield repair that ballooned past $500K in damage (and then broke again days later). From there the guys dig into debt — the psychological weight of payroll anxiety versus the strategic case for taking on debt to grow faster, and how each of them actually manages it personally and in business. Then Chris breaks down why his team just had its best month ever in a down market, why "the off-season" is really just a chance to do…