How I Handle Messy Property Titles (Podcast Ep#170)

Carl James is a 63-year-old retired petroleum company executive who has been investing in land since 2014 as a supplemental income source. After retiring in March 2023, he has transitioned land investing from a side activity to his primary focus, though he deliberately keeps it manageable to prioritize family, faith, and volunteer work. His why for investing differs from typical land investors—he doesn't need to replace a W-2 income or build to seven-figure net worth, instead using land deals to fund his children's education, vehicle purchases, and maintain his comfortable retirement lifestyle.

Carl's investment strategy has evolved significantly. Early in his career (2014-2018), he pursued high-volume mailing campaigns that generated abundant deals. However, he now focuses exclusively on distressed properties with messy titles, primarily by targeting tax court dockets rather than sending direct mail. His process involves monitoring tax court filings, conducting chain-of-title research, and cold-calling property owners facing tax liens or title issues. He intentionally waits until owners have received official notice of tax problems before contacting them, as this signals genuine urgency.

His target properties are typically those with heir situations, title defects, or delinquent taxes—properties most investors avoid. Carl demonstrates exceptional patience, noting that deals often take 3-6 months to complete, and occasionally 15 months to fully resolve all title issues. His underwriting assumptions target a minimum 100% annualized return, but he prefers 100% absolute return (meaning 200-300% annualized). He demonstrates this with a concrete example: purchasing a property for $5,000, not paying delinquent taxes initially, recording ownership, listing at $45,000, selling for $45,000, paying $10,000 in back taxes at closing, and netting $25,000 profit—a 500% cash-on-cash return in three months.

Carl emphasizes ethical business practices throughout the conversation. He compares his position to buying underpriced items at garage sales—the sellers have chosen not to address problems themselves, and he offers a legitimate service by solving those problems for a profit. He is forthright with property owners about their options: they can solve problems themselves (often at significant cost), hire a realtor to handle complications, or sell to him at a discount. He frequently directs owners to resources or real estate agents rather than pushing every potential deal, which he views as genuinely helpful despite not resulting in a transaction.

Regarding family involvement, Carl has structured different arrangements with his two adult children. His son worked extensively in the land business during college (2010s-2018) but has since pursued a career in finance and accounting, reducing his involvement. His daughter recently joined the business after leaving her teaching career to become a stay-at-home mother. Carl has documented processes, created training videos, and initially compensated her hourly while gradually transitioning her to handling more complex tasks like comparative market analysis (comping). He emphasizes the importance of clear expectations and exit strategies when involving family, cautioning that business relationships can damage family bonds if not carefully structured.

Carl advocates for a different approach than the high-volume, guru-course model dominating modern land investing. He believes serious operators are now returning to fundamental mailing because it genuinely works when properly targeted and formatted, contrary to recent claims that direct mail is dead. He spends 5-30 hours per week on his land business, depending on deal activity and personal commitments, with the flexibility to shift focus toward church volunteer work and family obligations. He views the modern land market as significantly more challenging than when he started—smaller investors need more capital now because response rates have declined, making the supplemental income model harder to execute.