The Step Most Investors Miss That Costs Them EVERYTHING with Jeremy Roll

Masters of Real Estate

Most investors think they’re doing enough due diligence, until they lose money.

In this episode, Matt Owens sits down with seasoned passive investor Jeremy Roll to break down where most investors go wrong, how to properly vet a deal, and what risk really looks like in today’s market. Jeremy has invested in over 100 opportunities across multiple asset classes and brings a brutally honest lens to what it takes to preserve capital and create reliable cash flow.

If you’re looking to invest smarter and avoid costly mistakes, this one’s for you.

💡 What You’ll Learn:

• Why you should never go all-in on your first deal, even if it looks solid

• The right way to vet operators (hint: it’s more than a background check)

• How to dissect a financial model and test assumptions around rent growth, debt, and expenses

• What hidden landmines to look for in legal docs that most investors miss

• When it’s smart to raise more capital upfront instead of relying on risky refinancing

• Why cap rate and interest rate math can quietly destroy your cash flow

• How to prepare your portfolio for a potential recession, without sitting in cash

Want more resources from Mathew? Grab his free due diligence checklist and other tools at www.mathewowens.com!