Dakota Rainmaker Podcast

Stephen Tiller on Leadership, AI, and Picking Up the Phone

April 28, 2026·22 min
Episode Description from the Publisher

In this episode of The Rainmaker Podcast, Gui Costin sits down with Stephen Tiller, who joined Sterling Global Financial roughly 13 years ago after a 35-year career across some of the most respected names in real estate finance and investment banking. Sterling, founded by David Kosoy more than 50 years ago, manages roughly $7–8 billion in assets across six countries and runs a platform that includes private credit lending funds, development and construction businesses, trust companies, and ba...

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