180. The 5 Pillars of Smart Private Real Estate Investing with Spencer Hilligoss

180. The 5 Pillars of Smart Private Real Estate Investing with Spencer Hilligoss

From Westside Investors Network (WIN) by AJ and Chris Shepard

February 25, 2026 · 1h 6m

About this episode

Spencer Hilligoss discusses the five pillars of smart private real estate investing and shares insights from his extensive experience in the field.

Check the episode transcript here ABOUT SPENCER HILLIGOSS Spencer Hilligoss is a passive investor who runs Madison Investing - a club where LPs gain access to the same types of niche investment opportunities where Spencer deploys his own money - including cash-flowing assets like self-storage, mobile home parks, multifamily and private credit. Spencer Hilligoss brings over 13 years of leadership experience as a former technology executive, building and scaling high-performing teams at five companies—three of which became billion-dollar "unicorns." Before co-founding Madison Investing, he led business development and professional development at LendingHome, one of the nation’s largest private lenders. As CEO, Spencer drives Madison Investing’s strategic vision, investor relations, and business development efforts. He is also an active investor and sought-after speaker, sharing his expertise on real estate and financial growth strategies. THIS TOPIC IN A NUTSHELL: · Spencer’s background in real estate investing · From Fintech to Full-Time Investing · Growing Up in Real Estate (And Coming Full Circle) · First Rental Lessons in the Bay Area · Scaling Through Long-Distance &amp…

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