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The Alternative Mason | Season 2 | Episode 7 | How Elite School Districts Became a Billion-Dollar Investment Strategy with Sean O’Dowd

What do elite school districts have to do with resilient real estate investing?


In this episode, Sean O’Dowd, Managing Partner of Scholastic Capital, shares how his “Scholastic Thesis” turns high-demand education zones into a powerful, defensive investment strategy. With multi-year leases, strict buy-box criteria, and a data-driven mindset, his approach offers stability in uncertain markets. He also unpacks the growing insurance crisis in states like Florida and why it may reshape U.S. real estate for years to come.


Key takeaways:

  • Multi-year leases in elite school districts create predictable income and economic stability.

  • A disciplined 17-point property selection process limits risk and maximizes tenant satisfaction.

  • Skyrocketing insurance costs may spark major demographic shifts in the U.S. real estate market.


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