#270.1: Navigating the Complex World of Real Estate Investing with Jay Kathol & Ashley Wells

This is Part 1 of our deep dive with Jay Kathol and Ashley Wells, and it’s a masterclass in what really happens behind the scenes of bigger real estate deals. Jay and Ashley walk through the highs and gut-punch lows of taking on a 40-unit multifamily, why their due diligence grade was a hard “C-minus,” and what they’d do differently before ever touching another boiler building again.

They talk legacy properties, inheriting a deal from family, and why sometimes singles and doubles beat swinging for home runs. You’ll hear how they started navigating bad tenants, contractor issues, surprise capital expenses, and a property with a rough reputation—plus how creative financing and buying the LLC instead of just the asset set the stage for what comes next in Part 2.

If you’re thinking about scaling into bigger multifamily or commercial, start with this episode so you don’t learn these early lessons the hard (and expensive) way.

👉 Listen in, subscribe, and share this with a partner or spouse you’re investing with so you’re on the same page before your next big deal.

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