Diners and Deals
Diners and Deals
Podcast Description
Welcome to Diners and Deals, the podcast where we dive deep into the journeys of entrepreneurs, business leaders, and investors making big moves in the business world. I’m your host, Seth, and in each episode, we bring you candid conversations with incredible guests who share their insights, successes, and the challenges they’ve faced along the way.
Whether it’s scaling a business, navigating private equity, or reinventing an industry, our guests bring a wealth of experience and a fresh perspective to the table. We go beyond the boardroom, discussing the personal stories and pivotal moments that have shaped their careers and the companies they’ve built.
Grab a coffee, pull up a chair, and join us as we talk shop in a casual, down-to-earth setting that feels more like catching up with old friends than a traditional business podcast. If you’re passionate about business, growth, and learning from those in the trenches, you’re in the right place. Welcome to Diners and Deals—let’s get into it!
Podcast Insights
Content Themes
The podcast covers themes such as entrepreneurship, scaling businesses, private equity, and industry innovation, with episodes discussing personal journeys like building a billion-dollar business, navigating equity investments, and transforming underperforming real estate.
Welcome to Diners and Deals, the podcast where we dive deep into the journeys of entrepreneurs, business leaders, and investors making big moves in the business world. I’m your host, Seth, and in each episode, we bring you candid conversations with incredible guests who share their insights, successes, and the challenges they’ve faced along the way.
Whether it’s scaling a business, navigating private equity, or reinventing an industry, our guests bring a wealth of experience and a fresh perspective to the table. We go beyond the boardroom, discussing the personal stories and pivotal moments that have shaped their careers and the companies they’ve built.
Grab a coffee, pull up a chair, and join us as we talk shop in a casual, down-to-earth setting that feels more like catching up with old friends than a traditional business podcast. If you’re passionate about business, growth, and learning from those in the trenches, you’re in the right place. Welcome to Diners and Deals—let’s get into it!
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
Disclaimer
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