Matthew Berry, Founder of Wayland Real Estate, shares the story of how he left law, entered capital markets, and eventually launched his own firm focused on middle-market multifamily and mixed-use opportunities in North Side Chicago and beyond.

In this episode, we cover:

• The moment John Buck took a chance on him—and what it meant

• How to reposition your professional identity and tell a better story

• The personal vs. professional dynamics of risk-taking

• What most sponsors get wrong about follow-through and reputation

• Why Wayland focuses on neighborhood-scale deals and how they underwrite risk

• The opportunity and capital gap in $5–$20M mixed-use and multifamily projects

This was a powerful discussion about professional reinvention, market discipline, and building a company around trust, local insight, and long-term investor relationships.

About: Eytan works at Greystone, specializing in Fannie, Freddie, HUD, CMBS, and bridge loans. This podcast is not affiliated with Greystone or any other institution, nor does it represent their opinions.

Intro voice-over by: Yitzy Rohatiner – ⁠⁠⁠⁠⁠yitzyrohatiner.com