Most investors don’t lose money at closing. They lose it months earlier, in a spreadsheet, when they accept an assumption nobody questioned.
Dr. Jason L. Williams is an active real estate sponsor and underwriter and the founder of Ironclad Underwriting. He has more than 20 years of investing experience and over $500M in transactions underwritten. After two decades of watching investors underwrite on gut feel, broker pro formas and fragile spreadsheets, he turned his own method into software any serious investor can use. His philosophy is simple: better decisions come from disciplined analysis, not optimism.
In this episode of Carson’s Corner: Entrepreneurship & Investing, Carson and Jason cover:
- Why most investors only find the broken assumption after they’ve committed capital
- The first things to check in a broker’s pro forma
- Why default assumptions like 5% vacancy and a 40% expense ratio can mislead you, and what to use instead
- Doing rent comps and rent projections the right way
- Why cap rates don’t tell the whole story
- Stress-testing debt and modeling the downside before the upside
- Building underwriting you can defend to a lender, an investment committee or your LPs
- Turning 20 years of deal discipline into a software platform
Whether you’re a sponsor, a passive investor vetting a syndication, or an entrepreneur buying your first commercial property, this conversation will change how you read a deal.
Connect with Jason at ironcladunderwriting.com, take his free masterclass, listen to the Ironclad Underwriting Podcast, or find him on LinkedIn.
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Passive Investments works with owners, investors, and family offices as broker and principal — commercial real estate, business acquisitions, and tax-advantaged structures.
Carson Jones
Carson Jones is the host of Carson's Corner, author of The Red Flag Playbook, a licensed commercial real estate advisor and business broker, and the founder of Passive Investments. He works with high-net-worth individuals, family offices, business owners, and sophisticated investors as a broker and principal.