George O’Brien: Real Estate Operations, Asset Growth, and Multifamily Investing | #64

George O’Brien, CEO of the YMCA of Greensburg, shares how he and his wife Angela built a real estate portfolio from the ground up—scaling to 158 units across Western Pennsylvania while maintaining full-time leadership roles and raising four children. Through Progressive Property Investments, the O’Briens manage both their own assets and those of other investors, employing a disciplined, operationally focused approach. This conversation explores their strategic entry into multifamily, portfolio management at scale, and the realities of running a vertically integrated firm outside of a major metro. Listeners gain perspective on how long-term vision, responsible leverage, and disciplined execution can drive durable wealth creation.

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