E39 - Contrarian Thinking with Spencer Hilligoss

Spencer Hilligoss is a passive real estate investor, multifamily co-sponsor and former technology leader. His company, Madison Investing, has co-sponsored deals totaling more than 4000 units for more than $500M. Spencer invests in syndications as an LP and actively leads Madison Investing alongside his Co-founder/Wife - Jennifer Morimoto. As a technology leader, Spencer built a 13-year track record of growing high-performing teams across five companies. In November 2019, Spencer “retired” from his lucrative technology career - leaving behind the $4B loan origination teams he built at LendingHome, funding 600 fix/flip transactions per month. Now, he is focused on spending time with loved ones and growing Madison Investing by helping passive investors achieve their goals.

In this episode, Tyler and Spencer’s discussion focused on the value of contrarian thinking, and how it can lead to new opportunities. Spencer shared how his 20 years’ experience in punk rock bands, combined with his background in various corporate roles, allowed him to become a whole person. He identified contrarian thinking as the single biggest driving force that saved him from a lifetime of corporate servitude, and he discussed how it has benefitted decision-making in real estate.

Other topics included relationship-building struggles for real estate investors, the clean slate technique, earning third-party credibility through authenticity, the consequences of hiring too aggressively, the hardships of management, inquiry vs. advocacy and more. Spencer provided uncommon wisdom and unique perspectives in this episode!

Music: Energetic Run (hooksounds.com)