How To Think About Risk – EP. 16


Risk is an often misunderstood and poorly communicated concept. This episode covers how we think about and evaluate risk factors in real estate and private equity investments.

Risk is going to be a part of every single investment decision that is ever made and there’s no such thing as a risk-free investment. So hopefully, in this episode, we can provide some tools and a framework to help you think about risk and overcome any hesitance you may have. Brad and I discuss risk from the academics’ perspective, real estate, and private equity side; as well as risk deal killers, and general risks that factor into any investment.

Key Takeaways:

[:10] About our topic of discussion today.

[1:51] How the academics think about and talk about risk.

[9:43] How we think about risk (in real estate and private equity.)

[12:26] How Brad looks at to evaluate real estate risk.

[14:42] More factors that go into risk analysis in real estate.

[17:28] Are there any risk deal killers? What risks would kill the deal?

[20:51] How I think about risk in private equity.

Mentioned in this Episode:

The University of Chicago

Modern Portfolio Theory (by Harry Markowitz)

University of California San Diego

Standard Deviation 


Due Diligence

Base Case

Downside Risk

Market Risk