435 | John Berkowitz | Harness the Fear: Building Empires in Real Estate and Beyond

In this episode of The Greatest Machine, host Darius Mirshahzadeh interviews John Berkowitz, a serial entrepreneur who built multiple successful companies in the real estate and technology sectors. John shares his journey from failed pharmaceutical sales interviews to co-founding Yodle (a company that grew to 1,000 employees and hundreds of millions in revenue), creating OJO Labs, and eventually merging with Lower. The conversation explores the evolution of entrepreneurship, lessons learned from building and selling companies, and the future of AI in real estate and mortgage industries.

In this episode, Darius and John will discuss:

(00:00) Introduction and Background

(02:04) John Berkowitz's Entrepreneurial Journey

(08:37) Lessons from Yodel's Success and Challenges

(16:58) Starting OJO and Its Evolution

(23:22) OJO's Impact on Real Estate and Technology

(24:25) The Journey to Acquiring Movoto

(27:36) Integrating Real Estate and Mortgage

(30:48) The Merger with Lower

(35:29) Understanding the Real Estate Market

(39:59) The Impact of AI on Real Estate

(48:00) Overcoming Barriers to Greatness

John Berkowitz is the President of Real Estate at Lower and General Manager of Movoto, where he leads efforts to integrate real estate search, agent support, and financing into a seamless homeownership experience. A seasoned entrepreneur and real estate technology leader, Berkowitz founded OJO Labs to help consumers make smarter homebuying decisions through personalized technology. He is also an EY Entrepreneur Of The Year Central Texas Award winner, recognized for his impact and innovation in the real estate industry.

Connect with John:

LinkedIn: https://www.linkedin.com/in/johnberkowitz 

OJO Labs: https://ojo.com/

Lower: https://www.lower.com/ 

Connect with Darius:

Website: https://therealdarius.com/

Linkedin: https://www.linkedin.com/in/dariusmirshahzadeh/

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

YouTube: https://www.youtube.com/@Thegreatnessmachine 

Book: The Core Value Equation https://www.amazon.com/Core-Value-Equation-Framework-Limitless/dp/1544506708

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