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Fannie Mae to Half a Billion: Jon Siegel on Surviving and Thriving in Multifamily

Aug 10, 2025
Jon Siegel, Partner and CIO at RailField, shares his journey from Fannie Mae to navigating tough market cycles in multifamily real estate. He discusses the importance of strategic partnerships and why staying active in real estate is crucial. The conversation turns to the rise of private credit, the myth of distress deals, and current investment opportunities. Siegel also emphasizes the significance of vintage deals and maintaining strong investor relations amid market complexities while expressing a long-term bullish outlook on multifamily housing.
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ANECDOTE

Founding During The Financial Crisis

  • Jon Siegel left big firms and started RailField during the financial crisis with two partners. They survived early years by doing advisory work and opportunistic deals to keep the lights on.
ANECDOTE

Starting On Third Base With Institutional Capital

  • RailField got a $50M emerging manager check that jump-started credibility and dealflow. The capital came with a playbook and forced them to scale from small deals to institutional-sized investments.
INSIGHT

Data Beats Herding On Market Selection

  • RailField built a market-scoring model to pick attractive metros rather than following herd opinions. That data-driven approach helped them target places like San Antonio and Richmond rather than obvious but weaker markets.
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