320: Merging Realty, Development, and Management with Ryan Cadwell

Description

On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene sits down with Ryan Cadwell, partner at Resolute RDM, to unpack how "dumb money" and undisciplined underwriting have distorted real estate markets over the last cycle. Ryan shares how cheap capital, short-term thinking, and inexperienced investors created inflated valuations that are now forcing hard lessons as loans reset and assumptions break.

The conversation dives deep into why advisory services matter more than ever, especially for out-of-state investors and newer buyers navigating markets they don't fully understand. Ryan explains why spreadsheets alone don't make good investments, how lenders' incentives can misalign with investors', and why slowing down often leads to better long-term outcomes.

Jonathan and Ryan also explore the human side of real estate, from landlord-tenant dynamics to the emotional toll of DIY management. They discuss why many investors unknowingly trade time freedom for stress, how ego and vanity metrics like "door count" lead to poor decisions, and why knowing what you actually want from real estate is more important than chasing trends.

In this episode, you will hear:

Why "dumb money" helps on the sale but hurts on the next buy
How cheap debt masked bad underwriting during the last cycle
Why lenders are not always the safety net investors assume
The difference between buying property and actually investing
How property management fees often save money long-term
Why asset management matters more than owning more doors

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