Uncontested Investing - The Insurance Strategy Every Rental Property Investor Needs with Scott Brown (Part 1 of 2)

Uncontested Investing Podcast - May 19, 2026

In this episode of Uncontested Investing, we sit down with Scott Brown from Steadily to talk about one of the most overlooked but mission-critical parts of real estate investing: landlord insurance. A lot of investors think about insurance only when a lender requires it or when a policy is up for renewal, but that mindset can create expensive blind spots. Scott breaks down why insurance should be treated like a strategic asset inside your portfolio, not just another closing-line item, and why investors who understand liability, deductibles, lender requirements, and risk transfer are usually much better positioned to protect long-term cash flow and growth.

We also get into how Scott got into the real estate space, why Steadily chose to focus specifically on landlord insurance, how investors can avoid closing delays caused by the wrong policy structure, and what newer investors should think about as they scale from one property to multiple units.

If you own rental property, are financing your next deal, or want to make smarter decisions around risk management, this conversation is a strong reminder that the cheapest policy is not always the best strategy, and the right coverage can keep one bad event from derailing your entire portfolio.