315: Thinking Outside the Short-Term Rental Box with Nick Korwin

In this episode, Jonathan sits down with Nick Korwin to explore the realities of scaling from long-term rentals into short-term hospitality and ground-up development. Nick shares how an engineering mindset, disciplined underwriting, and patience shaped his investment decisions.

The conversation digs into zoning and entitlement risk, why optimistic projections can derail development projects, and how data should be used as a guide—not a guarantee—when evaluating short-term rental opportunities.

Nick also offers a candid perspective on real estate “gurus,” explaining why assembling mentors across different skill sets and doing the work yourself leads to better long-term outcomes than following advice that sounds too good to be true.

In this episode, you will hear:

• Why zoning and entitlements are one of the biggest hidden risks in development
• How to underwrite conservatively by testing deals against worst-case scenarios
• Why judgment matters as much as data in short-term rental investing
• How to evaluate advice and avoid being misled by real estate gurus