LEGENDS RETREAT 2025

PRICES GO UP THE 15TH OF EACH MONTH UNTIL THE TICKETS ARE SOLD OUT!

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All-inclusive, invite-only mastermind retreat in Orlando, Florida.

Brainstorm with other like-minded moving and storage company executives in one of Florida’s largest mansions with tons of activities to keep you entertained while being indulged with knowledge, bartenders, masseuses, and more.

About the Event

This exclusive event brings together top movers and storage executives in a stunning 28,000 sq. ft. mansion. Attendees will enjoy engaging speakers, valuable networking opportunities, and access to luxury amenities, all designed to inspire collaboration and business growth in a relaxed, high-end setting.

SPEAKERS AT LEGENDS 2025

Jason Bergenske

CEO of MoveitPro Software
CEO of Lion’s Den Booking Service
Host of Shift Happens: Beyond The Boxes Podcast
Multi-Million Dollar Real Estate Investor

Gary Bergenske

35 Year Moving CEO Veteran
Former CEO of Shriners International and Shriners Hospitals for Children

JC Caldwell

Former CEO of Black Tie Moving
Owner & CEO of Live Tactically

Eric Wirks

Owner of Wirks Moving & Storage
CEO of USA Home Listings

Steven Reed

Founder of Big League Movers
Founder of Ready Roles

Greg SHEPPARD

Founder of USA Home Listings

Travis Weathers

Founder & CEO of Rotate Digital

Jeannie Buondelmonte

Senior Software Consultant
MoveitPro Software

Matthew Young

Founder & CEO of MovingLetters.ai
Founder & CEO of iHaul iMove Moving Company

Bruce Woodburn

Mortgage Lending Specialist
CrossCountry Mortgage, LLC
Multi-Million Dollar Real Estate Investor

ANNOUNCING SOON

ANNOUNCING SOON

WHERE WILL YOU STAY?

Enjoy the luxury of a 28,000 sq. ft. mansion with unparalleled amenities, including a bowling alley, golf simulator, sauna, and more. Each room offers a private bathroom, wet bar, and stunning views. For those who prefer alternative accommodations, nearby options are available. Click below to explore nearby stays that offer comfort and convenience during your time at the event.

WHAT IS INCLUDED?

Sponsorship Opportunities

Take advantage of exclusive sponsorship opportunities at this premier event. Connect with top industry professionals, showcase your brand, and increase your visibility through tailored packages that offer maximum exposure throughout the event.

Sponsorship provides a unique chance to align your business with innovation and growth in the moving and storage industry.

FREQUESTLY ASKED QUESTIONS

March 27, 2025 at 6:00pm EST

March 30, 2025 at 8:30am EST

Orlando International Airport (MCO)

Children under 18 aren’t allowed to attend as we are going to have Happy Hour.

You can add an additional attendee to your room if you like. If you would like more than 1 additional please contact MoveitPro.

If you require a refund, you must contact us no later than December 31, 2024. Unfortunately, if after that date no refund is able to be given.

The mansion is located in Orlando about 15 minutes from Disney World.

We will have a planned itinerary from 8 a.m. to 3 p.m. for the 28th and the 29th. Any time outside of that is free time where you can network, play games, swim, bowl, play basketball, watch movies, virtual golf, get a massage, etc. Our goal is to have some structure as well as fun.

You can see the speaker details here

Currently, anyone can come even if you are not a customer of MoveitPro.

Jason Bergenske

Chief Executive Officer
MoveitPro Software

Kayla Bergenske

Chief Operations Officer
MoveitPro Software

Nick Taylor

Director of Operations
MoveitPro Software

Jeannie Buondelmonte

Senior Software Consultant
MoveitPro Software

Steven Reed

Founder of Big League Movers
Founder of Ready Roles

As a founder of multiple ventures, including Big League Movers, Ready Roles, and On Deck Deliveries, my mission is to build scalable solutions that empower businesses to grow, thrive, and positively impact their communities. With over 16 years of experience, I’ve dedicated myself to creating and leading companies that redefine industry standards through innovation, integrity, and a relentless commitment to customer success.

Ready Roles: A New Venture in Strategic Support
Ready Roles is my latest initiative focused on providing tailored business support solutions for small business owners. We specialize in connecting entrepreneurs with executive assistants and support roles that align with their goals. By rigorously vetting candidates and matching them based on personality and strengths, Ready Roles is designed to help businesses scale affordably and effectively, even in today’s challenging economic climate.

Big League Movers: A Foundation of Integrity & Service
Since founding Big League Movers in 2008, we have prioritized creating a company built on values and community engagement. Our motivated movers are trained to deliver professional and hassle-free services, setting a new standard in the moving industry. We’ve grown into a regional leader, recognized by Inc. 5000 as one of the fastest-growing companies in the USA.

On Deck Deliveries: Precision & White-Glove Service
On Deck Deliveries was created to focus exclusively on the intricate logistics required for final mile delivery and white-glove furniture services. After performing deliveries in both the Atlanta and Memphis markets since 2014, we recognized the importance of building a company dedicated to excellence in warehousing, final mile logistics, and specialized handling. Our aim is to deliver precision and professionalism in every step of the process.

Building a Legacy of Impact
My vision is to scale Ready Roles, continue expanding Big League Movers, and solidify On Deck Deliveries as a trusted leader in final mile logistics. I am passionate about helping small business owners achieve their goals, create scalable solutions, and overcome today’s economic challenges. My approach combines strategic thinking, industry experience, and a relentless commitment to client success.

Travis Weathers

Founder & CEO of Rotate Digital
Travis Weathers is a devoted husband and father of three, as well as an accomplished entrepreneur. He is the CEO of Rotate Digital and a commercial pilot and flight instructor. Since 2019, he has helped over 200 moving companies increase their revenue through strategic SEO. Under his guidance, Rotate Digital has grown to over $3 million in revenue and secured a spot on the Inc5000 list of the Fastest Growing Private Companies, ranking among the Top 100 Fastest Growing Digital Agencies. Travis also helps other agencies do the same by helping them focus on creating value to drive business success.

Eric Wirks

Owner of Wirks Moving & Storage
CEO of USA Home Listings

If you wrote out Eric Wirks’s life on paper, statistically, his success, and where he is at in life today should not be possible. He has overcome unimaginable odds, and some of the hardest trials, tribulations, and low spots life could throw at someone. From poverty, childhood trauma, drug addiction, homelessness, prison, and PTSD. Today he is a loving husband, father, and son. A respected pillar in his community, and the industries he owns companies in. He is an active contributor to his favorite charities. An annual donor of tens of thousands of dollars in college scholarships at his former high school and is very generous with his time. Especially when it comes to helping entrepreneurs. If you ask Eric, he summarizes the success of his life and all that his life touches by living by three core values and principles: extreme ownership, integrity, and altruism.

Eric Wirks is the founder of Wirks Moving and Storage, a high seven to low eight figure moving and storage company, and one of the largest in the state of Georgia where he has achieved every entrepreneur’s dream as a 100% hands off owner, serving as Chairman of the board, working directly with his CEO and leadership team. Eric is also a serial entrepreneur where he owns, invests, or has partnered in other companies in the transportation, real estate, financial, and SaaS industries. In the summer of 2023 Eric received an amazing opportunity from longtime friend, former co-worker, and founder of USA Home Listings, Greg Sheppard, to become a hands-on partner and co-owner of USA Home Listings. As of December 2023 Eric was offered, and encouraged by Greg to take over the role as CEO of USA Home Listings which he accepted with great enthusiasm, appreciation, and honor. USA Home Listing is arguably the best data, direct mail, digital marketing, and direct outreach platform available in the moving and storage industry. It has been a huge contribution to changing the financial lives of many moving companies, and their owners by providing one of the best marketing tools and marketing services in the moving industry.

Eric is also very widely known for being one of two co-founding members of Moving Company Owners Unite. A moving industry owners networking Facebook group founded in 2017 when there was nothing like it in existence at the time, but there was a dire need for a platform for moving industry owners from across the country to come together, share best practices, and just help each other. Almost eight years later it turned into the largest, most respected, and valuable moving industry owners’ group with thousands of heavily vetted moving company owners online today. Some of the best friendships, business relationships, company success stories, and mastermind groups have been created because of this group. You could even say this group is the catalyst to the roots of many moving industry events in the present day

Bruce Woodburn

Mortgage Lending Specialist CrossCountry Mortgage, LLC

Bruce Woodburn is a mortgage expert with over 35 years of experience, helping more than 10,000 families and closing over 50,000 mortgage transactions. Specializing in loans for self-employed individuals and business owners with creative accountants, Bruce is known for crafting tailored solutions to fit unique financial situations. Featured on Fox News and the host of three radio shows across six Florida markets, Bruce also shares insights on iHeart Radio, Spotify, and YouTube. With 4.9-star ratings on Google and Zillow, he is committed to delivering exceptional service. Since 2017, Bruce and his team have been with CrossCountry Mortgage in Winter Park, FL.

MATTHEW YOUNG

Founder & CEO of MovingLetters.ai
Founder & CEO of iHaul iMove Moving Company

Matthew Young aka Matty Mailers is a visionary entrepreneur transforming the moving and marketing industries with a focus on authenticity and connection. As the founder of MovingLetters.ai, he’s revitalizing direct mail by delivering thoughtful, handwritten letters and thank-you cards that help businesses create lasting relationships with their clients. He also leads iHaul iMove, a moving company he founded in 2008 in Colorado Springs, where his roots inspire his commitment to helping movers nationwide.

Known for his forward-thinking approach, Matthew blends technology with personal touches, setting his businesses apart in crowded markets. A sought-after speaker and thought leader, he’s passionate about continual learning and empowering others to succeed. Whether inspiring industry peers or innovating customer experiences, Matthew’s unique vision and dedication make a lasting impact.

Jeannie Buondelmonte

Senior Software Consultant
For MoveitPro Software

Consultant with expertise in visual communication and technology. Starting her career during the personal computer revolution, she combined her design skills with a deep understanding of digital technology. Over the years, she evolved into a Senior Software Consultant at MoveitPro, where she helps moving company owners across the U.S. and internationally optimize their operations. With her unique blend of design and technical expertise, Jeannie continues to drive innovation and improve software solutions in the moving industry.

Greg SHEPPARD

Founder of USA Home Listings

Greg Sheppard, the visionary founder of USA Home Listings, is transforming the moving industry by empowering movers to connect with high-value clients. With over three decades of unmatched sales expertise in the field, Greg has established himself as a respected thought leader and mentor to countless moving companies across the nation. His unwavering dedication to raising industry standards and driving success has cemented his reputation as an indispensable force in the world of moving and relocation services.

JC Caldwell

Former CEO of Black Tie Moving
Owner/CEO of Live Tactically

Jonathan Caldwell is the former CEO of Black Tie Moving, a Inc. 500 Company, with 8 locations across the US, and over 300 employees. His strong focus on culture and a “Customer first” mentality has helped him and his team take Black Tie to the next level. He is also the founder and Co-owner of the “Liv Tactically” Brand, a tactical training, firearms and ammunition company.

He has not always been in the moving industry. He was an accomplished motivational speaker, police officer, and executive protection specialist in the US as well as overseas. In his lengthy Law Enforcement career, he has served as a K9 officer, a sniper, and other roles on multiple tactical units. He also served in an undercover capacity on a violent felony fugitive task force and the Child Exploitation and Human Trafficking Unit at his Department.

Jonathan or “JC” as he is known by friends and family, has spoken in 40 of the 50 states and a dozen counties around the world. He has been featured on Fox and Friends morning show, Good Morning America, Americas Got Talent, and countless other regional programs and nationally syndicated radio broadcasts. His excellent ability to communicate has held the attention of audiences everywhere from Elementary school students to Heads of State, Military Commanders, and CEO’s.

He has an exhaustive list of certifications and 1000’s of hours of Training and Operational experience. His extensive experiential knowledge of what it takes to operate under extreme conditions both in the business world and on the street is what makes him who he is today. This has made him a sought-after speaker and coach. He brings a very applicable and real word approach in his message of how to “Live Life Tactically…” by having balance in all areas of your life.

However, if you ask him his greatest accomplishment, he will say that it is not found in the list of
influencers he calls friends, or the multiple awards and commendations he has received as an officer
and business executive. Rather, it would be in his Role as a Husband, father, leader in his industry, and
constant learner in his faith. It is in all these areas that he practices every day the principals that he
teaches others.

Gary Bergenske

35 Year Moving CEO Veteran
Former CEO of Shriners International and Shriners Hospitals for Children

Gary J. Bergenske is a distinguished leader with over three decades of experience in the moving and storage industry, having successfully led J&J Metro Moving and Storage Company since 1985. His career has been marked by a relentless commitment to excellence, both as a business owner and as a mentor to countless entrepreneurs and industry professionals.

As a motivational speaker and author, Gary is renowned for delivering powerful messages on leadership, teamwork, and strategic growth, making him a sought-after presenter for industry conferences and corporate events. His unique ability to inspire and connect with audiences has made him a favorite at global forums, where he shares his insights on driving operational efficiency, navigating industry challenges, and creating a culture of success within organizations.

Gary’s leadership experience extends far beyond his business ventures. He served for 12 years on the boards of Shriners International and Shriners Hospitals for Children, including his role as Imperial Potentate in 2017–2018. In a memorable moment of his philanthropic journey, Gary had the honor of presenting a Humanitarian Award to President Jimmy Carter, recognizing his immense contributions to global humanitarian efforts. This recognition reflected Gary’s deep belief in the power of giving back and making a lasting impact on the lives of others.

At Legends Retreat, Gary will share transformative strategies for growing your moving and storage business, empowering your team, and leveraging leadership principles to build a thriving, sustainable company. With his extensive background in managing and scaling operations, Gary’s insights will help you tackle challenges head-on and set your business on a path to long-term success.

Jason Bergenske

CEO of MoveitPro Software
CEO of Lion's Den Booking Service
Host of Shift Happens: Beyond The Boxes Podcast
Multi-Million Dollar Real Estate Investor

Jason Bergenske is a visionary entrepreneur who has redefined the moving and storage industry with a series of innovative businesses. As the founder and CEO of MoveitPro, a leading CRM software for moving companies, Jason has helped countless businesses optimize operations, improve customer service, and achieve sustainable growth. His efforts have earned MoveitPro a spot on the Inc. 5000 list of fastest-growing private companies in the U.S.

In addition to MoveitPro, Jason founded Lion’s Den, a call center service that acts as an extension of moving companies. Lion’s Den provides full-service customer support, sales, and booking, with agents managing all aspects of client interaction to close deals, make sales, and ensure a high level of customer service.

Beyond his entrepreneurial success in these fields, Jason has a broader mission: creating generational wealth. At this point in his life, his primary focus is not only building his own legacy through strategic investments—such as his multi-million-dollar real estate portfolio—but also helping others build wealth and secure their financial futures. He believes in empowering individuals and businesses to create lasting, multi-generational success.

Jason’s entrepreneurial journey has been featured in Forbes and Young Entrepreneur’s Magazine. His podcast, Shift Happens, continues to inspire entrepreneurs, offering insights on business growth, leadership, and wealth-building strategies. Through his ventures and mentorship, Jason remains committed to leaving a positive, lasting impact on the industries and people he touches.