On this week’s episode, Kent is joined by Jonathan Greene, longtime investor and host of Zen and the Art of Real Estate Investing. Jonathan shares how growing up learning real estate “old school” from his attorney-investor father shaped his bias toward action, diversification, and treating each property like a business. He explains why many busy, high-income earners should start with passive syndications, what he vets first (the operator and the debt), and how fixed-rate, longer-term loans align risk with the hold period. The conversation closes with mindset, legacy, and teaching the next generation about money and real estate. 

Where to Find Jonathan:

• Sites - www.zenandtheartofrealestateinvesting.com, www.trustgreene.com, www.streamlined.properties
• Instagram - @trustgreene, @zenrealestateinvesting, @streamlinedproperties
• LinkedIn - https://www.linkedin.com/in/jonathan-greene-re
• The Zen and the Art of Real Estate Investing Substack - https://trustgreene.substack.com

Key Takeaways

• Start with passive if you’re time-constrained: it buys back your time while letting domain experts operate. 
• Underwrite the operator first, then the debt (favor fixed, 5–7-year terms that match the business plan). 
• Don’t over-optimize for door count or social-media optics; stay opportunistic and walk away freely when a deal doesn’t fit. 
• Diversify by asset class and geography through syndications to smooth portfolio “trajectory.” 
• Treat every property like a standalone business (revenue, OpEx, CapEx) and routinely prune underperformers. 
• Learning angle: passive LP deals double as education—study reporting, assumptions, and how seasoned teams execute. 
• Mindset matters: steady temperament, long-term thinking, and humility beat hype and ego. 

Books Mentioned

• The Wealthy Gardener by John Soforic (book): https://www.amazon.com/Wealthy-Gardener-Lessons-Prosperity-Between/dp/0593189744
   
  
  

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Production by Outlier Audio