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Executives Legend
The color legend to the right illustrates the various backgrounds for the top executives in the residential real estate industry.

David Osborn & Smokey Garrett

Founder & Chair, 
Waterloo Associates
2025 Rank: 86
Osborn and Garrett run Waterloo Associates, which is a major investor in five Keller Williams Realty regions and multiple market centers. Osborn founded Waterloo Associates in 2017 and is co-author of “Wealth Can’t Wait.” Garrett is operating principal of a Waterloo Associates’ portfolio company, Keller Williams GO Network Offices, which he co-founded with Osborn. KW Go has more than 3,900 agents who do nearly $9 billion in annual sales, which makes the franchisee the third largest in the U.S.

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