About Rick Chess
Rick Chess is a real estate dealmaker who gets results. Over three decades, he’s bought, managed, and sold tens of thousands of apartments and commercial properties, often working with institutional and private capital to create portfolios that outperform the market.
Rick specializes in the full lifecycle of investment real estate: finding value-add opportunities, structuring complex equity deals, scaling operations, and executing exits that maximize returns. He’s not about theory—he’s about what actually works in the real world, navigating tough markets, tax hurdles, and high-stakes negotiations.
Rick shares these insights with investors and industry groups navigating complex markets.
From acquisitions to exits, Rick’s guidance helps investors grow faster, avoid costly mistakes, and unlock maximum value. Realty Reality™ is where he shares the strategies, frameworks, and lessons that only come from being in the arena.
Join the Investor Community
A weekly email for investors who want to think beyond the next deal and build real estate businesses designed for long-term growth and exit.
Start With the Articles
Realty Reality focuses on the strategic side of real estate — the decisions that shape portfolios, partnerships, and long-term outcomes.
Why Realty Reality
Most real estate content focuses on finding deals.
Realty Reality focuses on what happens after the deals begin to scale.