Stories Behind the Door

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


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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 .

  • The NNN Myth: Why treating small trades, HVAC companies, and logistics entrepreneurs with a Modified Gross structure creates a better customer experience .

  • Municipal Partnerships: How to actively work with local cities to secure TIF benefits that bridge your 10-year P&L gaps .

  • Workflow Automation Over Autonomy: How to integrate AI layers into your underwriting and deal discovery without losing the mandatory human touch .

  • Building the Balance Sheet: Why Will prefers retaining the lion's share of equity and risk rather than living and dying by transaction syndication fees .

Whether you are a seasoned operator seeking local joint-venture opportunities or an entrepreneur ready to break out of the corporate 9-to-5 loop, Will's blunt, data-backed insights provide the ultimate roadmap for navigating real estate cycles . Connect with Thaddeus Campbell (S3 Partners): Email: [email protected] LinkedIn: https://www.linkedin.com/in/itsthadcampbell/ Connect with Will Skillman (Trowbridge Development) Email: [email protected] LinkedIn: https://www.linkedin.com/in/willskillman/ This Episode was brought to you by: https://www.kiwisteel.com/

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Stories Behind the DoorBy Thaddeus Campbell

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