Shift Happens: Beyond the Boxes

Hosted by Jason Bergenske

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Mar 2026

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About the show

Hi, I'm Jason Bergenske, the founder of MoveitPro Software, Lion's Den Booking Service, Host of Shift Happens: Beyond The Boxes Podcast and a Inc. 5000 List Winner CEO! My mission is to help as many company owners as I can from the experience I have of running my own multi-million dollar moving company, multi-million dollar moving software company, and a multi-million dollar call center that specifically books moves for moving companies like yours.

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39 recent

March 18, 2026Episode 3335 min

Ep 33 - How Chris Scaled a Moving Business from One Truck to an Empire

From a single beat up truck to building a thriving moving and storage business. Chris's journey is the definition of starting small and scaling big. In this episode, Jason sits down with Chris, Founder & President of True Friends Moving Company, to break down how he built his company from the ground up since around 2012. With limited resources but a clear vision, Chris turned hard work, consistency, and smart decision making into a growing moving empire. Chris dives into: ✅ How he started with just one truck and a dream ✅ Early challenges and lessons that shaped the business ✅ The key moments that helped him scale ✅ Building a strong reputation in the moving & storage industry ✅ Advice for entrepreneurs starting from zero If you're a moving company owner, entrepreneur, or someone looking for real-world business inspiration, this episode is packed with insights you can apply right away. 🚛 From humble beginnings to long term success. This is the story of how Chris built a moving empire from scratch #TrueFriendsMoving #ChrisJourney #MovingEmpire #FromOneTruck #StartupToSuccess #EntrepreneurStory #MovingIndustry #BusinessGrowth #ScalingUp #SmallBusinessSuccess #PodcastEpisode #hustleandgrow #movingbusiness

March 17, 2026Episode 3242 min

Ep 32 - 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: https://youtu.be/rI6JaiyPaEo?si=D0W-qD-yqoWGrvN-

March 3, 2026Episode 3236 min

Ep 32 - Scaling to $66M: Larry O'Toole's Blueprint for Building a Moving Empire (Part 1)

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.

October 22, 2025Episode 3136 min

Ep 31 - Streamlining the Move: Call Centers, Community and Legends Retreat

In this episode of Shift Happens: Beyond the Boxes, host Jason Bergenske — founder and owner of MoveitPro — sits down with Michael, Manager at Lion's Den, and Jeannie, Director of Business Development, for an insightful conversation about how innovation, teamwork, and community are redefining the moving industry. If you're a moving company owner looking to scale smarter, simplify operations, and connect with like-minded professionals, this episode is your roadmap to success. Transforming the Moving Industry with MoveitPro and Lion's Den The moving industry is evolving faster than ever — and those who embrace technology and collaboration are leading the way. MoveitPro, the software built for movers, by movers, has become the foundation for operational excellence. It allows moving companies to manage dispatch, scheduling, lead tracking, and customer relationships — all within one intuitive platform. Meanwhile, Lion's Den elevates the customer experience through expertly trained call center professionals who bring empathy, emotional intelligence, and genuine care to every conversation. They understand that moving is more than logistics — it's a deeply personal life event. Each interaction is an opportunity to build trust, reassure customers, and deliver peace of mind. This human-centered approach leads to consistent 5-star reviews, lasting customer loyalty, and powerful word-of-mouth growth. Together, MoveitPro and Lion's Den are proving that technology and heart can work hand-in-hand to transform the moving experience.

May 7, 2025Episode 2941 min

Ep29 - How Direct Mail Built a Moving Empire | Greg Sheppard (USA Home Listings)

In Episode 29 of Shift Happens: Beyond the Boxes, Jason Bergenske sits down with direct mail legend Greg Sheppard, founder of USA Home Listings. From quitting a job he hated to building a multi-million dollar lead generation business, Greg shares the raw, real, and ridiculously effective strategies that helped him—and many movers across the country—book high-ticket moves consistently. Recorded live at Legends Retreat, this conversation dives into how Greg went from cold-calling to closing luxury moves, and how smart, targeted mail (not spam!) can deliver massive ROI when done right. What You'll Learn in This Episode: The moment Greg risked everything to chase a new pathWhy most direct mail fails—and how to make yours stand out The system that helped moving companies scale to $10M+ How to target high-value homes and avoid tire-kickers Simple tips to increase conversions and get your phone ringing Whether you're trying to fill your pipeline or close bigger jobs, this is the no-BS breakdown of what works in moving industry marketing today. 👇 Resources & Links🌐 Learn more about USA Home Listings: https://usahomelistings.com🚀 Don't forget to LIKE, SUBSCRIBE, and COMMENT your favorite takeaway from Greg!

April 30, 2025Episode 2851 min

Ep28 - From 0 to Millions: Lessons from Legends of the Moving Industry (PART 2 OF 2)

In Part 2 of this no-holds-barred conversation from the 2025 Legends Retreat, we dive even deeper with two of the most respected movers in the game—Eric Wirks of Wirks Moving & Storage and Steven Reed of Big League Movers and Ready Roles. This is the real story behind scaling to $10M… and then having to fight your way back. 🎯 In this episode: ✅Going from profit to nearly $500K in the red ✅What happens when your sales team collapses ✅Selling off locations and rebuilding from the ashes ✅Staying profitable while downsizing ✅The emotional toll of being a business owner ✅How masterminds and friendships saved their companies ✅New strategies for long-distance, commercial, and military moves ✅Lessons you can't learn unless you live them 👉 Watch Part 1 first: https://youtu.be/76C6hNzprUA 🎙️ Subscribe now to never miss an episode of Shift Happens: Beyond the Boxes #MovingIndustry #ShiftHappensPodcast #BusinessGrowth #Entrepreneurship #EricWirks #StevenReed #LegendsRetreat

April 22, 2025Episode 2729 min

Ep27 - How Handwritten Mail Is Winning Big Jobs in the Moving Industry

What if one small shift in your marketing could land you bigger jobs, better customers, and deeper brand trust? In this episode of Shift Happens: Beyond the Boxes, recorded live at the 2025 Legends Retreat, host Jason Bergenske sits down with Matty Mailers—the creative mind behind Moving Letters and long-time owner of I Haul I Move. What starts as a conversation about mailers quickly unfolds into a deep-dive on: Reinventing postcard marketing with AI-driven handwritten letters The ROI of personalization in an industry where trust matters most How adding just one golden ticket or family photo can double your impact The shift from just "selling moves" to "selling trust" Running multiple businesses and learning to scale while staying personal Whether you're mailing 50 homes or 5,000, this episode offers a playbook for standing out in a sea of sameness.

April 15, 2025Episode 2651 min

Ep26 - From 0 to Millions: Lessons from Legends of the Moving Industry (PART 1 OF 2)

What does it really take to build a multimillion-dollar moving company from the ground up? In this episode of Shift Happens: Beyond the Boxes, recorded live at the 2025 Legends Retreat, host Jason Bergenske sits down with two industry powerhouses: 👉 Eric Wirks – Founder of Wirks Moving & Storage 👉 Steven Reed – Founder of Big League Movers and Ready Roles Together, they reveal the unfiltered truth behind their success—sharing the early days of hustling moves with MapQuest printouts, hiring their first teams, and pushing through massive setbacks like financial wipeouts, bad partnerships, and family emergencies. You'll hear: ✅ The real stories behind their first million in revenue ✅ What almost broke their businesses—and how they bounced back ✅ Why firing yourself from the truck is the key to scaling ✅ How to lead through chaos and build a culture that wins ✅ And yes… how drinking the Kool-Aid helped Steven transform Big League's entire culture Whether you're just getting started or scaling past 7 figures, this episode is packed with hard-earned insights, laughs, and leadership gold. 📍 Filmed at the 2025 Legends Retreat—a private mastermind for elite moving company owners. 👀 Stay tuned for Part 2, where they dive deeper into scaling teams, virtual assistants, and the next frontier of the moving industry.

February 4, 2025Episode 251 hr 9 min

Ep25 - From $1,000 to Millions: Steven Reed's Blueprint for Dominating the Moving Industry

💡 What does it take to dominate an industry from the ground up? In this episode of Shift Happens: Beyond the Boxes, we sit down with Steven Reed, founder of Big League Movers and Ready Roles, to uncover how he turned a $1,000 loan into a multimillion-dollar moving empire. 🚛💰 From scaling too fast to redefining company culture, Steven shares hard-earned lessons, leadership insights, and the strategies that fueled his success. Whether you're an entrepreneur, a business owner, or just love a good comeback story, this episode is packed with invaluable gems. Tune in now! 🎙️🔥 In this episode, host Jason Bergenske chats with Steven Reed, the founder of Big League Movers and Ready Roles, about his entrepreneurial journey in the moving industry. Steven shares how he got started in 2008 with a $1,000 loan from his grandmother, the hustle and sacrifices that led to his first million, and the challenges of scaling too fast when expanding into multiple locations. Key topics discussed include: The hometown dominator mindset—focusing on dominating a single market before expanding. The dangers of premature expansion, lessons from opening a second location in Atlanta, and why he ultimately sold it. The power of company culture and how he transformed Big League Movers with an innovative training and incentive program. How COVID-19 became an opportunity rather than a setback, allowing him to position his company as an essential service. The importance of customer experience, Google reviews, and relationship-building in scaling a moving business. His newest venture, Ready Roles, which provides virtual assistants for moving companies to optimize operations. Steven also discusses the Legends Retreat, a premier industry event where top moving company leaders gather to share knowledge and strategies. This episode is a must-listen for anyone in the moving industry or looking to scale a service-based business successfully. 🚀

January 19, 2025Episode 241 hr 29 min

Ep24 - Legends Webinar Special - Secrets to Moving Industry Success

Join us for a special webinar edition of Shift Happens: Beyond The Boxes, Episode 24! 🎥🎙️ This episode brings you exclusive highlights and expert insights from the Moving Legends LIVE Webinar featuring top industry leaders like Jason Bergenske, Jeannie Buondelmonte, JC Caldwell, and more. 🚛💼 Get ready to discover proven strategies, answer live audience questions, and gain the tools you need to grow your moving business in 2025. Plus, learn about the Moving Legends Retreat happening this March in sunny Orlando, Florida! ☀️ 📌 Highlights in this episode: Expert advice from webinar speakers Tips for scaling your moving business Exclusive sneak peeks into the Moving Legends Retreat Special offers for attendees 👉 Don't forget to like, comment, and subscribe to never miss an episode of Shift Happens: Beyond The Boxes! 🔗 Learn more about the Legends Retreat: www.LegendRetreats.com 🔔 Follow us on social media for updates and insights!