How to Spot Million-Dollar Deals: Avi Greenbaum’s Real Estate Blueprint - CEO of Triple Double RE

In this episode, I sit down with Avi Greenbaum to discuss his entrepreneurial journey and the decisions that defined his career. Avi shares his early ventures, including trading baseball cards as a child and running a travel business in college, which laid the groundwork for his approach to business. We explore how his ability to spot opportunities and his drive led him from Wall Street trading desks to ventures in software, real estate, and more.

Our conversation dives into Avi’s entry into real estate, where he recounts his first deal in condo conversions and how he handled financing, zoning, and market trends. Avi explains how he built teams, used creative financing structures, and launched a mortgage bank to support his projects. His insights into market cycles and strategic pivots offer lessons in risk management and adaptability.

We also explore Avi’s ventures in urban redevelopment, including his work in Delray Beach, Florida. From assembling parcels of land to transforming properties, Avi’s stories are full of lessons on perseverance, negotiation, and vision. This episode provides practical wisdom and a behind-the-scenes look at how Avi turned entrepreneurial efforts into success.

Connect & Invest with Jake:

Follow Jake on X: https://x.com/JWurzak

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Links:

Triple Double RE - https://www.tripledoublere.com/

Avi on LinkedIn - https://www.linkedin.com/in/andrewgreenbaum/

Topics:

(00:00:00) - Intro

(00:01:36) - Avi’s background and career

(00:25:46) - Getting deals done in South FL in the GFC

(00:52:34) - How to negotiate well

(01:11:02) Avi on Workforce housing 

(01:24:26) - Hotel conversions

(01:33:22) - What deals won’t you do?

(01:39:14) - The state of Office

(01:52:54) - What’s your favorite hotel?