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EPISODE 32 - Scaling to $66M: Larry O’Toole’s Blueprint for Building a Moving Empire

Picture of G. Jason Bergenske G. Jason Bergenske Mar 2, 2026 2:57:59 PM

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EPISODE 32 - Scaling to $66M: Larry O’Toole’s Blueprint for Building a Moving Empire

The Unconventional Blueprint to a Moving Empire: Lessons from Gentle Giant's Larry O'Toole

 

Ever wondered what it really takes to build a multi-million dollar company from the ground up? In a world often obsessed with ruthless efficiency and cutting costs, Larry O’Toole, founder of Gentle Giant Moving Company, offers a refreshingly human-centric approach. His journey, which began unexpectedly with a borrowed van and a roommate's initiative, reveals that the secret to scaling to over $66 million might just be as simple—and as challenging—as putting people first.

Join us as we unpack Larry's unique blueprint for success, diving into the core values, leadership philosophy, and unconventional strategies that turned a small moving operation into an industry powerhouse.

🚛💡 What You’ll Learn in This Episode:

What does it take to build a moving company generating over $66 million a year? In this episode, we sit down with Larry O'Toole, Founder & CEO of Gentle Giant Moving Company, to uncover the leadership principles, culture strategies, and operational systems that helped transform his company into one of the most respected brands in the moving industry.
 
Larry shares:
 
✅ How he built a people-driven company culture
 
✅ The systems behind scaling past $66M in revenue
 
✅ Leadership lessons from decades in business
 
✅ Advice for moving company owners ready to grow If you’re a moving company owner, entrepreneur, or leader looking to scale smarter and build a powerhouse brand, this episode is packed with actionable insights you won’t want to miss.
 
🎧 Tune in and learn how to build a company that moves more than boxes it moves people and businesses forward.
 

🎧 About the Podcast: Shift Happens: Beyond the Boxes

Hosted by entrepreneur Jason Bergenske, Shift Happens pulls back the curtain on the moving and home service industry—featuring real stories, hard lessons, and the strategies that drive long-term success.

🔔 Subscribe on YouTube, Apple Podcasts, or Spotify to catch new episodes.

Shift Happens: Beyond The Boxes Podcast
Hosted by MoveitPro Founder & CEO Jason Bergenske. With 3 Generations of moving company ownership, Jason decided to "Moveit" from his Families Moving Business, J&J Metro Moving and Storage to building a successful and essential piece of customer relationship management software with MoveitPro. Soaring to the Inc. 5000 List of fastest growing privately owned businesses in the United States, MoveitPro is the only moving software created by movers for movers. Now he's brought his knowledge of the Moving Industry to this amazing Podcast that covers Business Growth, Industry Challenges and guiding other moving companies to success with creative storytelling.