LumberJack and Christian Osgood talk Million Dollar Apartment Disasters

7 May 2026 · 39 min
39:10

In this YouTube interview, host Christian Osgood sits with seasoned multifamily investor Matt Hawkins ("Lumberjack Landlord") to dissect the Robin Hood jail‑to‑apartment conversion—a project that ballooned from an estimated 12‑18 months to over 30 months and cost far more than anticipated. They walk through the root causes of delays, including reliance on unfamiliar contractors, supply‑chain issues with fire‑suppression and plumbing products, loss of a project manager, and municipal permitting bottlenecks. The conversation then shifts to operational tactics such as the "sprint" approach to crew scheduling, the importance of strong relationships with lenders (highlighting a Texas‑based bank that offers high‑LTV financing), and creative equity structures that enable rapid portfolio growth while maintaining cash‑flow discipline. Both speakers share hard‑earned lessons: the perils of over‑leveraging, the need for transparent communication with banks, the value of targeting cash‑flow‑positive deals, and the strategic decision to sometimes walk away from high‑risk value‑add projects. The episode ends with a plug for an upcoming webinar on creative financing and a reminder of their regular weekly live shows.

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