On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene breaks down why most of his recent personal real estate deals have failed, despite decades of experience and a long track record of successful transactions. In this solo episode, he walks through several real deals that fell apart and explains the mindset behind why he chose to walk away from each one.

Jonathan shares how his perspective on investing has shifted as he has become more selective, emphasizing the difference between wanting a deal and actually needing one. He explains how inspections, unexpected costs, and changing assumptions often reveal risks that weren't visible at the outset, and why he is always willing to cancel a deal when the numbers or circumstances no longer make sense.

The episode also explores how negotiation style, ego, and pricing influence outcomes. Jonathan reflects on moments where he may have pushed too hard, as well as deals where walking away was clearly the right decision. Through examples ranging from mixed-use commercial properties to a short-term rental impacted by a natural disaster, he highlights how external factors and new information can quickly change an investment thesis.

For investors, this episode reinforces that failed deals are not mistakes but part of the process. By staying disciplined, unemotional, and willing to walk away, investors can avoid bad outcomes and focus on better opportunities.

In this episode, you will hear:

Why most of Jonathan's recent personal real estate deals have failed
The difference between wanting a deal and actually needing one
How inspections and unexpected costs can derail a transaction
Why being willing to walk away is a critical investing skill
How negotiation style and pricing influence deal outcomes
The impact of external events on an investment thesis

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Connect with Jonathan:

Website: www.streamlined.properties

Website: https://www.trustgreene.com/

YouTube: https://www.youtube.com/jonathangreenere

Instagram: www.instagram.com/trustgreene

Instagram: www.instagram.com/streamlinedproperties

Zillow: www.zillow.com/profile/streamlinenj

Bigger Pockets: www.biggerpockets.com/users/jonathangreene

Facebook: www.facebook.com/streamlinedproperties

Email: info@streamlined.properties

This episode was produced by Outlier Audio.