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Denver Partner Jay Montgomery holding a chair in the air with his hand

From Division I player to Business Power Player: How Denver Partner Jay Montgomery's Sports Experience Propelled him for Entrepreneurial Success

Gabriela Esquivel
You Move Me Denver Partner Jay Montgomery shares how his sports background helped him develop his business skills, his passion to support and uplift his team, and his number one advice for entrepreneurs.

YMM: How did you get started in the moving industry?

Jay Montgomery: I got started in the moving industry back in 1990 when I was in college. I grew up in Kansas City and attended Drake University in Des Moines, Iowa (where I played Division I soccer). While there, My friend and teammate Pat asked me one day what I was doing for work during the summer. I said I didn't know - at the time I had my own business mowing lawns. He said, “I am moving furniture - it's good work, good money, keeps you fit.” So I did that during my summer and winter breaks in college. I was moving furniture for a company in Kansas City. I even did a couple of long distance jobs.

After graduation, I moved to the Colorado mountains with some friends up in the ski town of Breckenridge. I lived there for 4 years, worked at the town's rec center, and met my wife there. Some time later, she and I decided to leave the town - move out of the mountains to Denver. I didn't know what I would do [for a job] at first, so I picked up moving again and worked as a moving crew lead and warehouse manager. The company I worked for offered me a dispatcher position but I would've had to move and I didn't want to do that.

So then I got a sales job as a trade show marketing consultant, which is a fancy way to say I helped companies with their trade show programs by selling them displays or graphics. I did that for 4 years and had a lot of success, becoming one of top salesmen for the whole company world wide. That gave me the ability to buy my first franchise in 2003 - I became the first owner of a junk removal franchise in Colorado.  

Franchise Partner Jay Montgomery

YMM: How did you become a You Move Me Franchise Partner?

Jay Montgomery: That first franchise I bought was doing good and I decided to go for another challenge. In the summer of 2012, I was presented with the opportunity to see if I would be interested in this new brand. I went to a meeting in Chicago to find out more about it, and at that meeting nobody in that room had worked on the trucks moving furniture for a living like I had - I knew what it took to do the work. So, I was interested and realized there was a real opportunity, especially in my market there was a need for a good quality, professional moving company, and jumped in on the opportunity almost right away. I was the first person to put the money down. Some would say I was You Move Me franchisee #1! I believed in it that much.

YMM: What is the most challenging thing about owning your own moving business?

Jay Montgomery: As I said, I was looking for another challenge and - in the beginning - it certainly was that. I always tell my team - so they know I have been in their shoes before - how I've done over 1,000 moves. I went on a lot of moves when I was General Manager. I also did all the hiring, managing, etc. It was a tough job, doing it all. On top of that, the moving business has peaks and valleys throughout the year, but also does that each and every month, which is more difficult to deal with than I had anticipated. [General Manager] Ricky Haley now has us fully staffed, but in years past we were never prepared for it - we were never staffed right and never fully staffed for the busy season. It's a challenge and, until you get that brand saturation when people are calling you on a consistent basis, it's hard to staff appropriately because it cycles within a month and within the year. 

YMM: Do you feel your sports background gives you an advantage as a business owner?

Jay Montgomery: Absolutely! I played with and against guys that went on to play professionally, so I've always had that drive, in sports and in business, which you need in this industry. We get thrown a lot of curveballs and you need to deal with them - see the challenge and meet the challenge. My degree was in advertising with a minor in sociology/psychology, which gave me the soft skills and experience needed in the moving business, because of the human aspect of it. Moving day is very hard for a lot of people. It's hard on the crew and it's hard on customers. From a crew perspective, it takes a special person to work til midnight and then come back the next morning and do it all over again. It requires a very strong work ethic to do this job. I knew what it took and I knew how to do it, so it wasn't a surprise to me how hard the work can be. Which is to say, this business is  not for the faint of heart!

You Move Me Denver team

YMM: How do you find the time to manage You Move Me, along with your other business ventures?

Jay Montgomery: For me, it was a transition that took place 5-7 years ago when I was doing too much. I'm fit, I played sports at a high level and feel like I'm in better shape now than ever before. However 5-7 years ago I was working too hard, stressed out and it was affecting my health and wellbeing. So I had to lean into the fact that I had good leaders on my team, and I had to change the structure. Now I make marketing decisions, manage the managers, etc. I've always been a ‘lead by example' kind of guy, but make sure everything is clearly outlined: find the people, get them on those seats and let them go. We have good leaders here that get things going. Now, I don't have to be in the kitchen day-to-day making the sausage so to speak. This is something that everyone should learn earlier in their entrepreneurial journey: lead the leaders, learn from your mistakes, and share the lessons learned with your leaders and empower them. Trust them and don't get in their way. Put good people in the right position and give them the freedom to grow and develop their skills and help them achieve that growth.

YMM: To what do you attribute the big success you’ve had over the last month?

Jay Montgomery: First of all, we are doing well, but when you look at year-to-year results, if you have a crappy year and the following year is great it makes that gap look good and amazing. It's Ricky and the team, I give him the credit - I found a good leader, and I believe our success lies in empowering our leaders. Ricky was on the practice squad of the Toronto Argonauts in the Canadian Football league. He could've played professionally but when Covid hit, American-born players had to return home. He played professional rugby here in Denver once he moved back to the U.S. - that's how we met because I have a rugby team connection. I took the chance to make him a manager of my business, because I know the athlete mindset and he has what it takes to do this job day in and day out. I identified he was going to be able to make it work - he has the stuff you can't teach. Ricky took that element from me of empowering the team. One of our guys, Dirk, was closing business at a higher rate than Ricky, so Ricky is smart enough to recognize that and empower him. You can't have any ego in order to empower your team and grow your leaders. The hoop looks large from where Dirk is shooting, so to speak, and I want him to do well - I want that for him. 

YMM: What motivates you?

Jay Montgomery: My family - I'm fighting for them, providing opportunities for my children. My kids are growing up in a different environment than I did. My parents were always concerned about money. They worked super hard and always provided for us and we never went hungry but looking back it was a fight every month. I'm enjoying providing an environment where we are not worried every day. My family is my reason. Close behind that, is providing leadership and opportunities for growth, sharing and helping others grow and develop as team members and leaders. I do like that a lot. And of course providing a good service to the community. We want to be the best moving company in this space, in my town, and in the system.

Franchise Partner Jay Montgomery, top right, with his You Move Me team

YMM: Where do you see yourself in 5 years?

Jay Montgomery: My daughter is in 5th grade, and my son is in 8th grade. I do see myself staying involved with things, still leading the businesses, maybe at a different level. Until the birds are out of the nest so to speak I'm not giving up, not ready or willing to leave the business. I anticipate all businesses to have grown significantly at that point. Same involvement, different level. I don't know how it'll look, but I'm definitely thinking about how it will look. Growing and evolving the leaders. Maybe expand within the state. Just continue to provide opportunities for our young leaders to grow. I can see things just getting better.

YMM: What advice would you give to your younger self?

Jay Montgomery: Kind of an interesting, several-layers kind of question. If I told you about personal things that have happened in my life, would I go back and change that? Because those things that happened made me the person I am today. I became who I am today from those experiences, and I wouldn't be here today if it wasn't for them. I am in a good place now, but I had to go through the trials that I went through. I wouldn't change what happened. But I would tell myself to keep showing up, keep being kind to yourself and others. I've always been loving and loyal to my friends and family, so I would say, keep showing up and good things will happen. I was not given anything, it was earned. When I first moved to Colorado I didn't have a car or a job. I don't begrudge anyone who's grown up with opportunities, but in my case there was no one who was going to financially provide me opportunities. I had to work hard and that is what I've always done. And I've had fun too. I love my family and I love my friends. I love my life and I wouldn't change it. What else would I say to my younger self? Enjoy your 20/20 vision while you still have it and your full head of hair! Just kidding!

Jay Montgomery (left) with family and friends  

YMM: What would you say to a young person looking to get on the entrepreneurial path?

Jay Montgomery: Be honest with yourself. Ask yourself: who are you, what do you do well, what do you like to do, what matters to you? Also, are you willing to put in the work?  Sometimes we try to square peg ourselves into a round hole. I was always a leader in the teams and jobs I've had, and when I look back and reflect back on my life it is clear to me that leaders lead. You can't take a leader and shove him in the cellar. Know who you are, and when the doors of opportunity open for you you gotta walk through, but you still have to show up and do the work. Opportunities will appear in front of you and you have to answer and do the work when they do. If you don't enjoy at some level what you're doing it's only a matter of time for that opportunity to fade and you'll find yourself having to do something else.

YMM: How do you keep growing and enjoying what you do? 

Jay Montgomery: There's alway an opportunity to get better. Just keep asking yourself: how do I continue to grow and develop? How can we top last year? I try to get better and try to find out how I can improve and how I can be a better father, owner, leader, husband.

Look for opportunities that complement who you are, and make your own path forward. I encourage all of our teammates to look at the opportunity that You Move Me offers. No one offered me an opportunity for business ownership when I was in my early 20s; now the opportunity is there you just gotta work for it. Make your own luck by being prepared for that and when it does arise, are you willing to take the chance and meet that opportunity? Are you willing to do the work? I've always believed in You Move Me - this is my 10th year and we are still here. I want to get it to where it's a strong successful business that will provide opportunities for my team, and that sense of pride that we made it through all those hardships and made it out the other end. That's a cool feeling.

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