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EPISODE 33 -Scaling to $66M: Larry O’Toole’s Blueprint for Building a Moving Empire (Part 2)

Picture of G. Jason Bergenske G. Jason Bergenske Mar 4, 2026 4:37:00 PM

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EPISODE 33 -Scaling to $66M: Larry O’Toole’s Blueprint for Building a Moving Empire (Part 2)

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

 

What does it really take to turn a moving company into a $66 million powerhouse?

In Part 2 of this high-impact conversation, we go deeper with Larry O'Toole, Founder & CEO of Gentle Giant Moving Company, as he pulls back the curtain on the mindset, leadership, and systems that built one of the most respected brands in the moving industry.

No fluff. No theory. Just real strategies from a leader who scaled it.

🚛💡 What You’ll Learn in This Episode:

 In this episode, we sit down with Larry O’Toole, Founder & CEO of Gentle Giant Moving Company, to explore the leadership principles, culture-building strategies, and operational systems that propelled his company into becoming one of the most respected names 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
 
🎧 Tune in and learn how to build a company that moves more than boxes it moves people and businesses forward.
 
If you missed the first conversation with Larry O’Toole, catch it here:
 

🎧 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.