Building a Service Driven Moving Company with Jerry Siegel of Midway Moving & Storage 2-19-26

Summary

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Podcast Summary: Becker Business – Building a Service Driven Moving Company with Jerry Siegel of Midway Moving & Storage

Date: February 19, 2026
Host: Scott Becker
Guest: Jerry Siegel, Founder & CEO of Midway Moving & Storage
Episode Focus: Strategies behind building a high-quality, service-driven moving company, lessons from nearly 40 years in business, and the culture and technology that set Midway apart in a competitive industry.

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Episode Overview

Scott Becker interviews Jerry Siegel about the founding, growth, and philosophy of Midway Moving & Storage, a Chicago-based moving company known for its service-driven approach, exceptional employee retention, and commitment to quality. Key themes include the professionalization of moving labor, creating a strong internal culture, leveraging technology, and lessons learned from large-scale growth and marquee clients like the Chicago Cubs.

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Key Discussion Points & Insights

1. The Birth of Midway Moving & Storage

• Background: Jerry Siegel founded Midway at around age 20, aiming to raise the professionalism and service standards in an industry dominated by day laborers and contractors.
  • "Since day one, our mission has been to provide the highest quality of service in the industry." – Jerry Siegel [01:06]
• Unique Approach: Different from competitors, Midway employs and trains all movers instead of using casual or independent labor.
  • "Midway is the only moving company in the industry that has built and trains its own people." – Jerry Siegel [02:21]
• Professional Staff: Emphasis on certified, career movers ensures consistent, quality service rather than the uncertainty of ad-hoc staffing.

2. Differentiating Through Service

• Personalized Experience: Midway offers comprehensive, custom-tailored service, guiding clients through every phase of the move—packing, storage, setup, debris/junk removal.
  • "We take time to walk our clients through every phase of the project... that extra personal touch where we walk you through every phase of the project." – Jerry Siegel [04:53]
• Empathy and Care: Recognizing moving's stressful nature, Midway’s staff aims to reduce client anxiety, not just relocate goods.

3. Operational Discipline in a Challenging Industry

• Consistency & Training: The company's quality comes from investing in people and rigorous training, not just seeking profit through volume or price competition.
• Long-Term Employees: Many employees have remained for decades (average tenure: 20 years), contributing to strong institutional knowledge and culture.
  • "I have employees that have been with me for over 35 years... The average employee has been with us for 20 years." – Jerry Siegel [08:24]

4. Key Inflection Points and Growth Lessons

• Winning Major Clients: The Chicago Cubs and government contracts underscore that reputation for quality precedes winning high-stakes business.
  • "You only get accounts like the Chicago Cubs by providing excellent quality service." – Jerry Siegel [07:25]
• Gratitude Toward Staff: Success is attributed to loyal, skilled team members.
  • "Our success is really a testament to the staff that we have." – Jerry Siegel [08:03]
• Diversification: Expansion beyond standard moving into storage, government contracts, elections, and more.

5. Building and Maintaining Company Culture

• High Standards: Rigorous hiring and a strong middle management team help maintain standards in an industry notorious for high turnover.
• Reputation: A brand synonymous with high-quality relocation, regardless of move type or distance.
  • "You try to get a reputation of equality... providing quality service day in and day out." – Jerry Siegel [10:23]

6. Technology, Adaptation, and Customization

• AI-Powered Planning: Investments in AI help gather detailed information on each project, allowing for more accurate, customized service.
  • "The AI platform that we use gives us a really good hands on approach to understanding exactly what the needs are for each particular client." – Jerry Siegel [12:13]
• Evolving Customer Expectations: Clients now expect tailored solutions and quick adaptation to changing circumstances.

7. The Underrated Lever for Success

• Team & Culture as Core Assets:
  • "The most important thing is surrounding yourself with good people... providing the highest quality service in the industry at a price that's affordable." – Jerry Siegel [13:58]
• Flexibility & Trust: Adapting to last-minute changes (e.g., delayed closings) and maintaining reliability breeds customer loyalty and referrals.

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Notable Quotes & Memorable Moments

• On Professionalizing the Industry:

  • "My goal and vision was to really professionalize and provide the highest quality of service the industry has to offer." – Jerry Siegel [01:56]

• On Employee Retention & Culture:

  • "I have employees that have been with me for over 35 years... At Midway, we're very well diversified." – Jerry Siegel [08:24]

• On Technology in Moving:

  • "We have an AI platform that helps us gather information on the project scope... It really helps us understand what the customer needs are." – Jerry Siegel [11:57]

• On Reputation and Quality:

  • "You try to get a reputation of equality...providing quality service day in and day out." – Jerry Siegel [10:23]

• Light-Hearted Moment:

  • Scott: "Yes. You moved us to Florida and the only difference between our home and the one that Mark Zuckerberg is buying…is about $149 million. That's the big difference." [17:38]
  • Jerry: "That's a small difference." [17:48]

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Important Timestamps

• 01:00: Jerry Siegel introduces himself and Midway Moving & Storage
• 01:49: Motivation for starting the business and differentiating through professional staff
• 04:46: Importance of service disciplines and personal touch in moving
• 07:23: Discussion on landing major clients and growing through quality
• 08:24: Employee retention, company culture, and diversification
• 10:20: Building and sustaining internal culture and reputation
• 11:54: Technology adoption—AI for customized moving projects
• 13:53: The value of people and quality in long-term business success

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Tone and Language

The episode is conversational, positive, and pragmatic, mixing humble gratitude with clear-eyed business insights. Both Scott Becker and Jerry Siegel maintain a tone of mutual respect and a bit of humor.

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Summary

This episode offers a masterclass in building a service-driven company in a crowded, operationally intense industry. Jerry Siegel’s focus on hiring, training, and retaining staff—combined with a commitment to personalized service and embracing technology—has made Midway Moving & Storage a leader in its field and a trusted partner for major institutions and long-time clients alike. The lessons are universally applicable: success hinges on people, consistent quality, adaptability, and leadership that genuinely cares.

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Transcript

[A]

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[B]

This is Scott Becker with the Becker business in the Becker Private Equity podcast. We're thrilled today to be joined by a brilliant, sort of adept, flexible, smart business leader and founder. We're joined today by Jerry Siegel. Jerry's the founder of Midway Movers and Storage. Done an incredible job of building a great business. And Jerry, can you take a moment and introduce yourself and tell us a little bit about Midway Moving?

[C]

Absolutely. First of all, thank you, Scott. It's a true honor to be with you today. And it's all my pleasure. My name is Jerry Siegel and I'm the president and CEO of Midway Moving In Storage. We're based in Chicago, been in business for almost 40 years now. And since day one, our mission has been to provide the highest quality of service in the industry. And we've done ever since our inception almost 40 years ago, that's been the mission.

[B]

I mean, it's simply amazing. You started this and you're literally about 20 years old or so. And what drove you to start Midway Movers? Midway Moving? What. What drove you to get it going and how did you get it going?

[C]

Well, you know, I knew some people in the industry and when I was, you know, in my 20s, like you said, and I noticed that quickly noticed that the industry is made up of many day laborers, independent contractors. And my goal and vision was to really professionalize and provide the highest quality of service the industry has to offer. So what I did was just like any leader, you try to surround yourself with intelligent business leaders and business advisors and try to grow the organization in a way where we train and employ our people so very much. You know, the way Midway differentiates itself from our competitors, that's a highly competitive industry, is we train and employ all of our own people. In fact, Midway is the only moving company in the industry that has built and trains its own people. So when people call Midway, they get certified professional movers, people, individuals that this is what they do for a living. It's not, you know, like an independent contractor who picks up day laborers and, you know, they drive, you know, some. Most of these van lines. What they do is they have these drivers that drive from city to city all over the country, and they pick up casual labor. You know, many of these folks, they walk into million dollar homes and never touch the piece of furniture before. And that's the difference between Midway and others out there, right? So other companies, what they do, you know, they oftentimes pick up this casual labor. But when clients call us, they get people who really understand what it takes to successfully complete a project.

[B]

And what I'll tell the audience is we have actually used Midway moving for a moving job and had a crystal clean, fantastic experience. So not only am I interviewing Jerry on the Becker business podcast, Becker private equity podcast, we've also been a customer. And our experience was exactly as you note and completely truthfully, fantastic. Talk for a second about moving is a brutally competitive business, operationally intense, lots of different labor flying around with different moving companies. What are a couple disciplines that you had to be very good at to be able to master this at scale and do it at the scale that you do it?

[C]

Yeah, that's a good question, Scott. Excellent question. First of all, moving can be very stressful, right? People move for all different sorts of reasons. It could be a new job, divorce, death in the family, whatnot. So I think the difference that Midway brings to the table is that we take time to walk our clients through every phase of the project from whether it be packing, moving, storage, setup, debris removal, junk removal, whatever is needed in the entire process, we can handle. And most companies don't really. I mean, they don't really take the time to really understand what the client's going through, what the challenges are, what the obstacles are at origin, destination, and where we come in and we provide value to our clients is that extra touch, that extra personal touch where we walk you through every phase of the project. And I think that's where the major difference is between, you know, when people call Midway up. We built this brand. We wanted to people to understand, hey, when you call Midway, you're going to get the best quality of service in the industry. And they're going to walk you through every phase of the project. They're going to hold your hand. You know, moving, like I said, moving is very stressful. So for some, for most people. So it really, it really takes time. We have a. We have a large staff of people that are committed to providing that added touch. It's not just moving from a. To you know, moving from here to here, we provide every. We provide the personal touch, which is far above what the industry provides.

[B]

And take a second, Jira, you've been at this business for some time. I've watched you grow tremendously. I think you're the official moving company for the Chicago Cubs and just have done this incredible job of growing the business. Give me, in your journey as a founder, a couple of the big inflection points, either lessons learned the easy way, the hard way. What are a couple inflection points in the business over the years that you've seen as you've grown and as we had to get better at? Talk a bit about that journey.

[C]

Well, you know, you only get counts like the Chicago Cubs by providing excellent quality service. Obviously, we didn't provide the, we didn't have the quality behind the service level that we do. The Cubs wouldn't use us. Right. So, you know, I think that the most important thing is that, like I said, the training center, training our people, really providing emphasis on quality has really brought it all together. And you know, any business leader will tell you that surrounding yourself with quality people is important. Right? You can't. You know, I could be the best business leader in the industry, but without the right staff and the right, the right middle management team and staff and people that are committed really doesn't. I wouldn't be too successful if I didn't have the right team behind me. And I think that providing the end result, at the end of the day, it really, our success is really a testament to the staff that we have. So I couldn't be grateful. I couldn't be thankful. And I'm so totally grateful for, for the staff that I have. And many of our employees have been with us for years and years. You know, I mean, I have employees that have been with me for over 35 years, and the average employee has been with us for 20 years. So at Midway, we're very well diversified. Okay. We do storage, we do moving locally long distance. We do government work. In fact, we were hired by. For this upcoming election, we're gearing up to provide polling stations set up and distribution for the upcoming primary election. And the only way you get counts like that, Scott, is to really have an excellent quality service. And that's what we built. We built a brand where people know when they call Midway they're going to get the best quality of service in the industry at a very fair price.

[B]

And take a moment, Don. Building that culture internally, you're in a business that's traditionally very High turnover. Yet you've recruited trained, retained people over a long, long period of time. How do you build that culture? And I know you personally to know to be just a really good person. How much is that culture? Come leadership. Just wanting to take care of people well and take care of customers well. Talk a little bit about building that culture and retaining people well.

[C]

You try to get a reputation of equality and you know, once you get into family and networks and business networks and all of that, your name gets out there, right? And your name gets out there in terms of the quality of service you provide. And, and you know, it's providing quality service day in and day out. Our middle management team, like I said, is very tough and we expect a lot from our employees when they go out there. Actually we don't just hire like most of our competitors, like I said, they hire independent contractors, day laborers and this sort of thing. We put our guys through a regular curriculum before we'll put them on the street. You know, we work with our people. We, we train our people. We, we expect a lot because our customers expect a lot. So and, and I think over the years, like I said, our brand has. People equate our brand with high quality relocation service, whether it's local, across the street, across the country, where we're prepared to handle any type of project in any city or state.

[B]

Thank you very, very much. Talk about the for a second, how has the business and technology changed and customer expectations changed over the last 10 years or so?

[C]

Okay, so that's a good question, Scott. You know, we updated our technology. We an AI platform that helps us gather information on the project scope. You know, every move is different, right. People have different furniture, people have different, there's different obstacles moving in and out. Sometimes there's a lot of artwork or televisions and all, you know, specialized pieces that have been installed in the house that people want to take with them. So the AI platform that we use gives us a really good hands on approach to understanding exactly what the needs are for each particular client. So we get that information through this AI platform and it really helps us understand what the customer needs are. And we use that to help develop a plan, a relocation plan that works and is customized for each individual project.

[B]

Thank you. And the customers really expect that individual customized service. Know what you're doing, what you're getting. And again, I feel like, you know, a broken record, but we've used the service and had just fantastic help from, with midway moving and just fantastic customer experience. So. Right on, on that. When you Think about working in a blue collar business, lots of hard working people, and I know it's a mix day of technology, white collar and blue collar. But what's the most underrated lever for long term success in building the business that you've built that people might not talk enough about?

[C]

Well, like I said before, Scott, the most important thing is surrounding yourself with good people. And you really need a good team of people that are really dedicated to the overall mission, right? And that is providing the highest quality of service that the industry has to offer. And that's really what it comes down to, providing the highest quality service in the industry at a price that's affordable. Our prices are right in the middle of the market, but where we stand out is in the quality of the service that we provide. You cannot find a better quality service in our industry. And I am so thrilled and proud of my staff and from the middle management team, from the executive team to the middle management team, to the actual movers that are, that are doing the actual moving every day, it's truly very labor intensive, as you know. And again, I have committed people that are totally loyal to the company and that have been with me for years and years. So I couldn't be more thankful to my staff and everyone who's helped us get to almost 40 year benchmark. And we are the largest, most recommended moving company in the state of Illinois because of them, because of my staff. Like I said, I could be the greatest leader in the industry, but without the great people that I have around me, I would be nothing. Right? So I'm grateful to have such a great staff. I have great friends, colleagues and, and business associates who've used this year many years and you're, you're one of them. Scott, we moved you to, I think if I remember correctly, we moved you to Florida like you said. And you know, it's just a pleasure to work with so many great friends and colleagues and, and families who really put their trust in us. And it's, you know, they open the doors, you know, we understand there's many relocations that are difficult, that are highly stressful, like I said. And just having their trust and the way we work with people and they totally trust the quality of the service. They know when they call Midway, they're going to get an excellent team of professionals coming through the door. Uniformed professionals know what they're doing and really understand the scope of the project based on all the information that we're able to gather at the beginning of the project and things from the start of the project to the end. Things change all the time and we're able to adapt to any obstacles that may change. Sometimes when people get ready to move, a closing falls through and they're not able to move into their new place right away. We have storage available. We're able to accommodate any last minute request. People feel comfortable dealing with a company that can adapt to quick changes and can handle any type of situation that can arise during the project.

[B]

No. Fantastic. And we've watched it and I think your thoughts on building a culture and building a team are so completely right on. I've watched you do it for 35 years plus now. It's really remarkable.

[C]

Yes.

[B]

You moved us to Florida and the only difference between our home and the one that Mark Zuckerberg is buying, $150 million is about 100 is about $149 million. That's the big difference.

[C]

That's, that's, that's a small difference.

[B]

That's not, that's not, that's all it is in any event. Jerry, what a pleasure to visit with you. Jerry Siegel, Founder CEO, Midway Moving in storage. Remarkable what you've accomplished over a long period of time and keep on doing incredible. Thank you so much.

[C]

Thank you, Scott. It's been a pleasure. And thank you again for inviting me to your podcast. It's truly an honor to be here and you've set the bar very high. Scott, I'm just trying to keep up with all your success. That's all I'm trying to do.

[B]

You're doing just great. Just fantastic. Fantastic. It's just fantastic. Jerry, thank you so much for joining us. Please give the family our best and it's great to talk to you.

[C]

Same to you, Scott. Take care and we'll talk soon.

[B]

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