The Importance of Being a Lifelong Learner with Paul Wakim

28 Mar 2023 · 39 min
38:45

In this Uncontested Investing episode, host Tim Herridge interviews Paul Wakim, a nomadic real‑estate investor and tech founder. Paul recounts his journey from a post‑college real‑estate photography startup (sparked by a graduation‑gift drone) to self‑teaching Python, building a predictive algorithm for sellers, and eventually creating Townsquare, an off‑market property marketplace for wholesalers and investors. He explains the company’s multiple pivots, the current MVP (1,200 users, 450‑650 properties listed per month), its data‑privacy controls, free posting, paid tools for buyers, and a roadmap of monthly feature releases. Paul shares market insights – institutional buyers are on the sidelines while local flippers need better access – and discusses challenges such as buyer‑list access and platform adoption. Throughout, he emphasizes a lifelong‑learning mindset, humility, and the importance of stepping outside for mental health. The conversation also touches on the team composition (co‑founder Mitch, sales director Kevin, salesman Taylor, and offshore developers), fundraising goals, and an eventual exit strategy aimed at acquisition by a large industry incumbent. The episode ends with a rapid‑fire advice segment urging investors to take daily outdoor breaks.

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