Ritter on Real Estate 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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Production by Outlier Audio