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This week, Anne and Chris welcome back Jude Chiy, founder and CEO of Flamingo, for one of their most candid and wide-ranging conversations yet. Jude opens up about the early struggles that shaped his leadership style, including hiring mistakes that pushed him to completely rethink how he builds and manages a team, and how those hard lessons led him to build a company where every role, every feature, and every decision ties back to one metric: resident retention.

Jude breaks down the performance management framework that runs Flamingo, including how he writes job descriptions around outcomes instead of tasks, why he doesn't care how long something takes as long as the result is achieved, and how giving employees a clear north star actually empowers them to push back and prioritize better.

The conversation also gets into the evolution of Flamingo itself, from a wellness and fitness platform called Hello Healthy to a full resident retention suite, and what Jude learned from walking the streets of Chicago for four months talking to property managers and residents. Plus, why he believes consistent resident communication is one of the fastest ways to improve retention, what authentic resident-driven engagement looks like, and why brand may be the most important long-term advantage any multifamily operator can build.

If you've ever struggled to get your team aligned and moving in the same direction, this episode is worth your time.

Flamingo - Resident Retention App
400K+ units use Flamingo’s Resident Retention Platform to stop Retention Leak & hit 63%+ retention.