Ep 266 Ask, Don't Tell: What It Takes to Lead People Well with Josh Zolin
On this episode, host Tyler Dickerhoof, sits down with Josh Zolin, former Hollywood stuntman turned CEO of Windy City Equipment, an eight-figure HVAC company he inherited from his father and built into an Inc. 5000 business.
Josh unpacks the leadership shift that changed everything for him: moving from telling people what to do, to asking questions that help them conclude it themselves. He goes deep on authenticity (and why the word itself can breed inauthenticity), the difference between power and force, what it really means to lead with empathy, and how vulnerability in a boardroom — or a termination meeting — can be your greatest asset.
Josh is also the author of Blue Is the New White and host of the podcast Everything They Don't Tell You.
👉🏻 Save your seat in the next Lead Without Hiding Challenge HERE.
Meet Josh
CEO | Windy City Equipment | Founder and Creator of Blue is the New White Academy.
Before Josh became the CEO of Windy City Equipment, he was a stuntman. Literally. He grew up around risk, discipline, and consequences.
The stunt world taught him how to take a hit, stay calm under pressure, and get back up without complaining. Turns out, those lessons translate pretty well to business and leadership.
At 27, he became CEO of Windy City Equipment after spending years in the field. Not in conference rooms. In kitchens, on rooftops, and next to technicians fixing broken equipment.
No college degree.
No shortcuts.
Just sweat equity, curiosity, and learning how to listen before trying to lead.
Today, Windy City Equipment is a 3x Inc 5000 (Fastest Growing Companies in America), multi-state commercial service company supporting restaurants and foodservice operations. It is not glamorous. The work is hard. The industry is unforgiving. Building teams that actually care, communicate, and take ownership is the real challenge. It's also the work Josh is most proud of.
He is also the founder of BITNW Academy, built to develop the soft skills, mindset, and financial understanding that most blue-collar professionals were never taught but desperately need to grow. Leadership, communication, accountability, and ownership are not optional anymore.
Resources, books, and links mentioned in this episode:
Connect with Josh at:
https://www.youtube.com/@impactdrivenleader
https://www.instagram.com/thetylerdickerhoofshow/
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https://impactdrivenleader.beehiiv.com/
About the Tyler Dickerhoof Show Podcast
The Impact Driven Leader Podcast, hosted by Tyler Dickerhoof, is for Xillennial leaders who have felt alone and ill-equipped to lead in today's world. Through inspiring interviews with authors from around the world, Tyler uncovers how unique leadership strengths can empower others to achieve so much more, with real impact.
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