Matthew Berry

WORK HISTORY

EDUCATION

SKILLS

ABOUT MATTHEW BERRY

I have spent the past 17 years advising, investing in, and practicing law within the real estate industry. Today, I am the Founder and Principal of Wayland Real Estate Capital, a boutique investment firm that sponsors and manages real estate investments for high-net-worth individuals and family offices, with a primary focus on durable income and disciplined risk management. Wayland targets core+ and select opportunistic investments, primarily in Chicago and a limited number of national submarkets where local knowledge creates an informational edge. We focus on situations where pricing dislocation, capital constraints, or operational complexity create opportunities to generate strong risk-adjusted returns without relying on outsized residual assumptions. Our approach is shaped by two core principles: • Risk-adjusted return matters more than absolute return. In a higher risk-free rate environment, the efficient frontier flattens, and the most compelling opportunities are often found lower on the risk spectrum. • Refinancing risk is real risk. We pair each investment with a capital structure that can withstand a range of future market conditions, avoiding business plans that require exceptional exit environments to succeed. Since launching Wayland in 2024, we have focused on assembling a portfolio of stabilized and near-stabilized assets with strong in-place cash flow, while selectively pursuing more opportunistic investments where our local knowledge and strong operating partners minimize execution risk. Our investor base consists primarily of high-net-worth individuals and family offices. We co-invest alongside our partners in every deal and prioritize capital preservation, transparency, and alignment. Prior to founding Wayland, I worked in real estate law and institutional real estate investment, including roles at Shefsky & Froelich (now Taft Law), Skadden Arps, and The John Buck Company.I earned a JD from Northwestern University School of Law and a bachelor\'s degree in Political Science from Northwestern University. I have also completed post-graduate coursework in valuation, investment, and real estate development through The University of Michigan’s Ross School of Business, The Wharton School, and MIT’s School of Architecture and Planning.