Episode 485: Investing & Managing In Lake County With Bill and Shannon Powers

Straight Up Chicago Investor · Oct 15, 2026 · 52m

Bill Powers, who first joined us back in Episode 6, returns with his daughter Shannon Powers to share how their real estate business has evolved since 2021!

Bill and Shannon discuss how they've scaled their portfolio over the last several years, jumping into ground-up development in Florida, and lessons learned from investing in a declining market! They dive deep into short-term and mid-term rentals including identifying markets, underwriting deals, and best management practices. The duo explains how they've been able to have their STR/MTR business work in synergy with their traditional…