Zen and the Art of Real Estate Investing with Jonathan Greene

100: The Mindful Approach to Real Estate Investing with Jonathan Greene


Mindfulness is a valuable trait no matter where you apply it. In real estate, having awareness and empathy can make all the difference between getting a great deal or not getting it at all.

This is the 100th episode of Zen and the Art of Real Estate Investing, and Jonathan’s friend and previous podcast guest, Alyssa Holbrook, takes over the microphone to interview Jonathan. Mindfulness has been deliberate in his investing career, but it took center stage in his 40s.

Alyssa and Jonathan’s conversation covers how hustle and work ethic relates to mindset, his ability to self-regulate when others feel dysregulated, and how therapy played a big role in Jonathan’s personal growth. He explains his approach to using his network mindfully, remaining confident when others would like to tear you down, and what leaving a legacy means to Jonathan. You’ll also hear the value of mediation in his daily life, how the podcast has changed him, and putting negotiations in real estate in perspective. Finally, Jonathan shares how this podcast has changed him and how he plans to implement what he’s learned from his guests in 2024.

Mindfulness is a choice, and Jonathan’s interview with Alyssa reveals how it contributes to his success in real estate and beyond.

In this episode, you will hear:

  • Jonathan’s unique take on mindset, which led him to start the podcast

  • How real estate could be better with a mindset shift and more focus on relationships

  • Mindful use of your network and what that looks like

  • Financial desperation’s impact on a business and what you can do to “mindset” your way out of it

  • Why rushing around crushes the ability to be mindful

  • What Jonathan’s dad taught him about being a good landlord and mindset

  • The lessons he’s learned about self-regulation and what to do when things feel dysregulated

  • Therapy’s benefits and how it helped Jonathan become a better person

  • Avoiding FOMO, it’s relationship to his intrinsic motivation, and meditation

  • The one thing he hopes his kids learn from him

  • How work ethic and not rushing can be intertwined

  • Hustle as a state of mind

  • Jonathan’s high standards and how he uses those to adjust the trajectory of his business

  • Why each investor’s journey is their own

  • Releasing regret, embracing feeling good about yourself, and finding others who want to do what you want to do

  • Money’s impact on the group of people you’re surrounded by

  • Shifting your perspective to create a better real estate deal for everyone

  • The art of negotiation and being transparent

  • The podcast’s role in Jonathan’s life and how it’s changed him

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If you enjoyed this episode, we’ve created a PDF that has all of the key information for you from the episode. Just go to the episode page at to download it.

Supporting Resources:

Jonathan’s website –

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Find Alyssa Holbrook on Instagram –

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