Stories Behind the Door

Why Will Skillman Went All-In on Midwest Small Bay Flex (And Won)

June 17, 2026·31 min
Episode Description from the Publisher

I sit down with Will Skillman, Founder and CEO of Trowbridge Development, for an unfiltered masterclass in small-bay industrial flex operations and raw entrepreneurial discipline . Will has flipped 100 homes, managed dozens of apartment buildings, and rolled up massive mobile home portfolios across the Midwest before targeting the highly fragmented small-bay asset class . We unpack the exact economic indicators driving the small-bay boom in 2026, where sub-5% vacancies meet a massive gap between acquisition costs and soaring replacement costs . Will explains why he chose to pull back the reins on 15 months of development planning to protect his investors' capital, how he structures deals using seller notes to bridge valuation gaps, and why maintaining total equity control trumps chasing institutional fee-play models every single time . Key Takeaways from this Episode: The Intelligence of Capital Discipline: Why walking away from unfeasible projects is the ultimate sign of investment maturity .</s

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