On this episode of Zen and the Art of Real Estate Investing, Jonathan Greene welcomes Ari Rastegar, founder and CEO of Rastegar Capital and author of The Gift of Failure. Ari shares his journey from delivering pizzas and attending law school to building a vertically integrated real estate platform with institutional-scale developments across the country. The conversation centers on discipline, philosophy, and how setbacks became the foundation for both his personal growth and business success.

Jonathan and Ari explore the mindset behind enduring market "winters," the cyclical nature of real estate, and why failure is an essential teacher. Ari discusses his approach to entitlements and master-planned communities, his prediction for one of the largest real estate booms in decades, and how technology—from robotics to 3D printing—could reshape the cost and speed of new construction. He also opens up about health, daily habits, and the quiet discipline that sustains high performance in volatile times.

Listeners will take away a deeper understanding of how to balance ambition with patience, why zoning and long-term planning are undervalued edges, and what it means to invest in projects—and people—with lasting value. Ari's story is a reminder that compounding growth begins not in markets, but in the consistency of who you are when no one's watching.

In this episode, you will hear:

• How a $3,500 land purchase in law school launched Ari's development career during the run-up to the Great Financial Crisis

• Why he views market "winter seasons" and failures as essential to building a resilient, multi-billion-dollar real estate platform

• The demographic, technological, and housing-supply forces that he believes will drive an unprecedented real estate boom over the next decade

• How personal development, tiny daily improvements, and emotional awareness compound into better business decisions

• Why zoning, entitlements, and construction innovation (including 3D-printed and robot-built housing) are critical to solving the housing shortage

• How Rastegar Capital structures large projects so accredited investors can co-invest alongside major institutions

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Supporting Resources

Connect with Ari:

Website: www.rastegarcapital.com

Youtube: https://www.youtube.com/@rastegarcapital

Facebook: https://www.facebook.com/rastegarcapital

Instagram: https://www.instagram.com/rastegar/

LinkedIn: https://www.linkedin.com/company/rastegarcapital/

Twitter: https://x.com/arirastegar

Connect with Jonathan:

Website - www.streamlined.properties

YouTube - www.youtube.com/c/JonathanGreeneRE/videos

Instagram - www.instagram.com/trustgreene

Instagram - www.instagram.com/streamlinedproperties

Zillow - www.zillow.com/profile/streamlinen​j

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

Facebook - www.facebook.com/streamlinedproperties

Email - [email protected]

This episode was produced by Outlier Audio.