Probabilistic Investing and Fixed Debt Wins ft. Andrew Cushman

On this week’s episode, Kent is joined by Andrew Cushman. Andrew shares his journey from chemical engineer to full-time multifamily investor, with more than 3,000 units syndicated and repositioned. He explains why chasing “rough C” properties created more risk and headaches than reward, why class B assets offer the best risk-adjusted returns, and how probabilistic thinking guides his underwriting and debt strategy. Andrew also dives into the importance of fixed-rate financing, downside protection, and why he takes pride in never losing investor money even through volatile cycles.

Where to find Andrew:

LinkedIn: https://www.linkedin.com/in/andrewcushmanvpa/
Website: https://vpacq.com/

Key Takeaways

• Don’t get stuck doing everything yourself—hire earlier to scale smarter.
• Class B assets often provide stronger long-term returns with fewer operational headaches than older class C properties.
• Think probabilistically: account for non-zero risks (like rapid rate hikes) and eliminate them where possible.
• Fixed-rate debt and properties that cash flow from day one provide critical downside protection.
• Always underwrite conservatively with cap rate expansion and realistic rent growth to create “lots of ways to win.”

Books mentioned

• How to Win Friends and Influence People — Dale Carnegie: https://www.amazon.com/How-Win-Friends-Influence-People/dp/0671027034

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https://hudsoninvesting.com/

Production by Outlier Audio