Join host Will Jarvis for a special impromptu episode recorded at a conference in Charlottesville, Virginia, where Jay — a Norfolk-based assessor and host of the Conversations in the Mirror podcast — flips the script and interviews Will. Together they explore how property taxes fund local communities, the regressive nature of current assessment models, tax abatements for large commercial properties like stadiums, practical AI tools for entrepreneurs and assessors, and what drove Will to build Valuebase from rural North Carolina into an $8 million-funded company serving assessment offices nationwide.

• 00:00 - Introduction and how Jay's impromptu interview came together at a Charlottesville conference
• 02:00 - Will's background: growing up in rural eastern North Carolina and attending UNC Chapel Hill
• 03:30 - The founder mindset: balancing arrogance with humility and outworking the competition
• 05:00 - What kept Will going through the hardest startup moments: mission over money
• 06:45 - What Valuebase does: building automated valuation models and tackling regressive property taxes
• 08:30 - How property owners should think about property taxes as community investment
• 10:30 - Property taxes as the foundation of local government revenue (65-75% of city budgets)
• 12:00 - Tax abatements for stadiums and large corporations: who really bears the burden
• 14:00 - Favorite AI tools: Claude, Grok, Gemini, Perplexity, and why specificity matters over AI hype
• 16:00 - Practical AI advice: setting up Claude CoWork for daily workflows
• 17:00 - How Will raised $8 million: podcasting, relationship-building, and asking for advice instead of money
• 19:00 - Rapid-fire reflections: Will's definitions of success, service, and identity as a founder
• 21:30 - The 10-year vision: Valuebase in 80% of U.S. assessment jurisdictions and the Jack Dangermond inspiration