High-Risk Auto, Underinsured Homes & Legacy: Insurance Wisdom with Jacob Carroll | Whiskey Wisdom Podcast On the Whiskey Wisdom Podcast, co-hosts Tyler and Chris welcome Jacob Carroll, owner and agent of Superior Insurance, while they sip a 115-proof Yellowstone barrel pick and discuss flavor, seasons, and living near the coast. Jacob shares his move from Florida to North Carolina after a seven-day water fast that brought clarity and led to a youth pastor role, then into sales and ultimately insurance, where a mentor encouraged him to start his own agency. He explains helping “harder to insure” drivers (DUIs, points, suspended licenses, credit impacts), rising underwriting scrutiny like unlisted household drivers, and why insurance is required with plates or mortgages. The conversation also covers widespread home underinsurance amid rising values and premiums, replacement cost estimating, ethics, claim realities, and Jacob’s view of success as family legacy, mentorship, and being present for his kids.