Masters of Moments

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

Jan 8, 2025

Avi Greenbaum, CEO of Triple Double RE, shares his entrepreneurial journey from trading baseball cards to tackling real estate. He discusses his first successful condo conversion, revealing the intricacies of financing and market trends. Avi highlights his innovative deal-making tactics, including transforming urban spaces in Delray Beach. He emphasizes the importance of adaptability in fluctuating markets and shares insights on negotiating effectively, including the art of silence. His stories are packed with lessons on resilience, opportunity, and bold strategy.

01:56:39

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Episode guests

Avi Greenbaum

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Episode notes

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Quick takeaways

Avi Greenbaum emphasizes the importance of having a clear ask in business to seize valuable opportunities and connections.

His early entrepreneurial experiences, from trading baseball cards to running a travel business, shaped his business acumen and negotiation skills.

Adaptability in real estate investing, especially during fluctuating market conditions, is crucial for identifying distressed properties and creative financing options.

A strong commitment to sustainability and community development informs Avi's projects, aiming to transform underperforming properties into affordable housing and mixed-use developments.

Deep dives

The Importance of Having an Ask

Having a clear ask in life and business is essential for success. The speaker emphasizes that being prepared with an ask allows individuals to take advantage of opportunities when they arise. For example, a chance encounter with Warren Buffett in an elevator highlighted the significance of knowing what to ask for, even if the ask is small or seemingly insignificant. Without an ask, one risks missing out on valuable interactions and potential opportunities in both personal and professional contexts.

Intro

2min

From Cards to Commerce: An Entrepreneurial Journey

24min

Navigating Condo Conversions and Market Dynamics

17min

Navigating Real Estate Challenges

10min

The Art of the Ask

12min

Innovative Strategies in Real Estate Investment

6min

Navigating Workforce Housing Challenges

17min

Navigating Financial Challenges in Real Estate Deals

2min

Navigating Real Estate Financing and Zoning Challenges

3min

10.

Navigating Distressed Real Estate Investments

18min

11.

Real Estate Dynamics: Multifamily vs. Office Markets

6min

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

1 on 1 coaching with Jake: https://www.jakewurzak.com/coaching

Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo

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