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From Stuntman to Service Empire: Building with Grit and Purpose - Josh Zolin - CEO of Windy City Equipment
Manage episode 482872407 series 3599637
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In this episode of Diners and Deals, I sit down with Josh Zolin, CEO of Windy City Equipment, to talk about what it takes to build a service business that scales—without losing your soul. Josh started his career as a Hollywood stuntman before joining his father’s one-man repair operation. Over time, he helped transform the company into a multi-state commercial kitchen equipment service provider, while staying deeply connected to the skilled trades.
We dig into Josh’s journey of self-discovery, from identity struggles and career pivots to a defining personal tragedy that reshaped how he leads. He shares how he built a values-driven company culture, why presence matters more than growth at any cost, and how writing his book Blue Is the New White helped him advocate for the next generation of skilled workers.
We also cover:
The challenges of scaling high-trust service operations
What it takes to expand into new markets—and when to pull back
Lessons in leadership, hiring, and letting go of ego
How to structure a business that prioritizes people and reputation
The evolving conversation around private equity in the trades
The emotional and personal growth required to lead with authenticity
This episode is a powerful reminder that building a great business starts with understanding who you are—and having the courage to grow alongside it.
Links:
Josh on LinkedIn - https://www.linkedin.com/in/joshzolin/
Windy City Equipment - https://www.windycityequip.com/
Seth on LinkedIn - https://www.linkedin.com/in/sethdeutsch/
CSuite Financial Partners - https://csuitefinancialpartners.com/
Topics:
(00:00:00) - Intro (00:02:29) - Introducing Josh Zolin (00:05:57) - The Origins of Windy City Equipment (00:07:22) - From Technician to Business Leader (00:21:50) - A Family Tragedy and Transformation (00:31:51) - Expanding the Business and Writing a Book (00:35:00) - Starting a Career in Skilled Trades (00:37:52) - Lessons Learned from Expansion (00:42:33) - Building and Restructuring the Organization (00:51:23) - Navigating Financial Leadership Challenges (00:54:50) - Vision for the Future and Private Equity (01:00:43) - The Importance of Presence and Overcoming Fear (01:06:48) - Closing Remarks and Reflections
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