HI 114 - Creating a Sustainable Business on Active Duty with Rollors CEO and USAF Officer Matt Butler
7 Dec 2025 · 17 min
Interview with USAF officer and entrepreneur Matt Butler about creating Rollors, an outdoor lawn game he conceived during a deployment. Butler started with a garage prototype, validated demand at a church craft fair (sold 50 units that day), and grew the business to roughly 50,000 games sold through retailers including Dick's Sporting Goods, Amazon, Wayfair, REI, Camping World and his site rollers.com. He describes outsourcing marketing and other functions, learning PR by doing press releases himself, later working with veteran-owned marketing firms and other vendors, and the long lead times for magazine placements (example: Costco magazine distribution ~6.5 million; took ~1.5 years). Butler is a 20-year Air Force member (about to retire), has moved 10 times and done 10 deployments, holds patents on the game, and engages veteran entrepreneurship networks (IVMF EBV program/other veteran entrepreneurship bootcamps). He emphasizes testing, learning roles before hiring, hiring veterans preferentially (guaranteed interview), and offers mentorship and contact via rollers.com.
Questions this episode answers
Close to 50,000 games.
He sold 50 units on the first day.
Dick's Sporting Goods, Amazon, Wayfair, REI, Camping World, and rollers.com.
About 20 years (has moved 10 times and completed 10 deployments).
He graduated from the IVMF EBV program at FSU last summer.
Chapters
Welcome to the Heroic Investing Show. As first responders, we risk our lives every day. Our financial security is under attack, our pensions are in a state of emergency. A single on duty incident can alter or erase our earning potential instantly and forever. We are the heroes of society. We are self reliant and we need to take care of our own financial future. The Heroic Investing show is our toolkit of business and investing tactics on our mission to financial freedom.
Hello and welcome to the Heroic Investing show where we focus on the challenges unique to first responders, members of the armed services and veterans. But we also focus on some of those challenges that all of us as investors and business startups, entrepreneurs face as we get those new companies, those new businesses going. I have Matt Butler here with me. Matt's an Air Force officer, still active duty officer. He's also running a successful entrepreneur business, full fledged company providing an actual product. We talk a lot with individuals who are doing what I do, which is more of a passive investment in real estate or in other types of businesses ran by other people. But really the theme of our discussion here and the reason I think that Matt and I got together and is that we want to inspire entrepreneurs out there, whether you're first responders, service providers, active duty military or even veterans working another job already to start your own business to explore your unique genius and share it with the world. And you do that by working in the evenings and on the weekends building that business that you just know in your gut is the right one. So everyone, thanks for joining us on this one. And Matt, thank you so much for joining me.
Thank you, Gary. I appreciate being on here. I hope that I'll be able to educate and help some of listeners in regards to some of my successes and failures along the way.
This is two days in a row that I've interviewed awesome Air Force pilots in uniform ready to go out. And actually Lane, if you haven't caught the interview with Lane Bean, go back and listen to that one. Another awesome individual and he was actually near the flight line and there were 16s going over top of us. So it was a little bit challenging on the audio quality. What I think Matt would be really helpful. When you started this company, successful company with distribution and a lot of intricate things that most of us don't think about in the military. You're a pilot or you're on an aircraft and this isn't what you normally do. You don't do production lines. So how did you come up with rollers and a little bit maybe about what your company's like, sure.
So a little background on me, military wise. So I've been in for 20 years. I've moved 10 times PCs and I've been on 10 deployment.
Wow.
Probably about seven years ago on one of my deployments, I started to conceptualize an outdoor game. And that was started because I was really a little homesick. I was in the Middle east, imagining being back, having a beer, hanging out with friends, family, and just enjoying community and socializing with people through just outdoor games and being outside and growing up in 70s and 80s, we played a lot of bocce ball. I grew up in Minnesota. And so I was thinking there's got to be another game out there, something new, something that's more. More fun or just a different way to play an outdoor game. And so that's how I started conceptualizing a game which today I call rollers, which is similar to. It's got kind of a fusion. I guess I consider myself like a scientist of lawn games. I can bind up.
Horseshoes and lawn bowling and bocce into one game. It started in my garage as a prototype and I showed it to some friends at a barbecue for entertainment and they really enjoyed it. And I knew that I would get a lot of either just buddies just busting my butt about creating a game in my garage. And I would also probably get some good feedback from them just saying what they thought of the game. But then I had a friend that was independent from me, that didn't know me, and he really enjoyed the game, actually wanted to buy it from me. So with that I thought, no problem. And I sold him the game and I created another one. And through word of mouth I sold a few more games and I thought I should really test this out. And I went to our church's art and craft fair. So to kind of set the stage where we've got a lot of like grandmas and older people and they have doilies and, you know, we have candles and all these different things that are there at the church and cupcakes. And then you have me and I have a new handcrafted lawn game that was there. It was the first time that really anyone's ever seen it. People looked at it and I explained it, I did my pitch. And you can imagine the box that it was in looked like something from maybe Hasbro from like the 60s or 50s. It was, you know, just a brown box with a big sticker on it. And somebody wanted to try it outside. And I said, sure, take a set and give it a try. And Let me know what you think. Well, what happened is that was right in front of the church and everyone saw the game being played. So prior to people going into the church fair, as they saw the game being played and other people played it and then they enjoyed it. And then I had people coming in saying, hey, I played that game outside. Do you have one? And then I started selling them. And in the first day of the church fair, I sold out of them And I sold 50 of them. And you think that, you know, 50 is not a lot of units to sell, but it was proof of concept. Sure. It showed that there's interest in the game. So if I fast forward to today, I've sold close to 50,000 games through different retailers, through Dick's Sporting Goods, Amazon, wayfair, our website, rollers.com, rEI, Camping World. And so from that period of selling in the church fair to today, there's a lot of stories that I. Hopefully we can talk about whatever you want that the listeners would be able to learn. Because I've had some failures, no question. It wasn't easy. A lot of weekends have gone away and I've had to just reprioritize. And this company has just grown quite a bit on its own, but I've had to strategize and kind of vector it in the direction.
So this is fascinating to me because I'm an entrepreneur, a closet entrepreneur. This goes back to this memory that I've had many times. When my sister and I were kids, there was a craft fair thing at a nursing home that we used to. My mom worked at. And so I decided that everyone going to the craft fair needed a puzzle of their name, their initials. So we made all the letters in the Alphabet, I think, or most of them, and wooden puzzles, and we cut them up and we put them back together and put them in the. You know, we packaged everything. We were like 12 and 13 or something like this, and it took forever. In my dad's workshop, we didn't sell one. It turns out that people didn't need what we thought. I thought everyone would want one. I don't know why. I still don't know why people don't need a puzzle with their initials, but it is important. So the reason I tell that silly story is because as you listen to Matt in this, I think the biggest takeaway is going to be it doesn't matter that it's the game rollers, which, by the way, looks like a lot of fun. It could be a widget, it could be really anything. Any business that you've got rattling around in the back of your head that you think that's really, you know, I want to do this. But they're all going to have like proof of concept. They're going to have test cases or beta versions. Right. They're going to have marketing. He's got a great story about marketing we're going to talk about in a moment. And then who do you employ? He's made some good and bad decisions about employment. And then also, I don't know if we'll get to all this, but a great discussion, not specifically about marketing. It was more about understanding each aspect of your business so that you know who to hire. Right. And so we don't forget that aspect. Could you talk kind of about the marketing that we talked about before recording and what you mentioned about understanding the job of somebody you're going to hire before you do it?
I do a lot of outsourcing and before I do any outsourcing, like you said, I want to understand what I'm outsourcing to and how they can do it. And it's also, you also have to, I think, evaluate on what you like to do and what you have a lot of interest in and what you don't like. For example, I don't like to do financing. I don't think I'll ever be a cpa. The nice thing is as I married somebody that really enjoys that, my wife. So that part works out very well.
Yeah.
Feel like I'm more of an operations officer and I like to do that and strategize and so that's what I'm holding on to while I outsource other things like the one we talked about. Marketing.
Yeah, that's great. But you also mentioned that maybe not every time, but specifically with marketing, when before you hired somebody to like write, copy or contact a magazine for advertising, you first did that job yourself or at least learned what it was so you knew how to hire the right person and you had a story about how you hired the wrong person.
I did. So we've had some excellent success in our marketing. We've been in Inc. Magazine, Entrepreneur, New York Times, Today Show, 3Times, Fox and Friends, Good Morning America. So we've been in a bunch of different locations and I can't take credit for all of that because I outsource it to a wonderful veteran owned marketing company. But when I first started off, I did it on my own where I read an article about how you the process behind it of creating a press release. So you can gain interest from an editor or somebody on a news station. And I started sending out large quantities of these press releases, and what I really needed to narrow down on was the quality of them. Then I looked at different marketing companies, and I outsourced it to one once. I felt that I had a decent understanding, but I didn't understand the cost. And so that company actually was the most expensive company I've worked with, and they did the least amount of, or acquired the least amount of marketing out of all the other companies I worked with. And so really getting into the weeds of having an understanding of. Of the full spectrum is very important. And that's. I don't call it a failure because now I hopefully can share that story with other people. And hopefully I now have an understanding of the cost and the benefit and what to expect, too. That was another thing that I learned about marketing is expectation. I'm very persistent and want things done now and tomorrow and things like that. Well, with marketing, they don't print magazines overnight. It takes time. So you need to wait six months, seven months for things to come out. I had an article in Costco magazine, which their distribution is very high. It's somewhere around 6.5 million people. It went out to all of their members, and that took about a year and a half in the making. So that wasn't something that it just happened overnight. They had to find the right spot. We had to have the right story, the right pictures, because that goes out to so many people. That magazine has to be perfect to them before it goes out. So I had to hold back on wanting for those things to happen overnight. And that was another learning point for me.
That's awesome. How many employees do you have in the company?
Just myself and my wife. We outsourced social media strategists, manufacturers. We have warehousing and so everything. So I would. If I said all of the outsourced people, I would say a dozen different people.
And most of the people that you outsource to, especially in the warehouse area and distribution, are military. Right. Or veterans.
Yep. I've stormed through military networks, or a lot of them have just reached out to me. A lot of my social media advertising is towards veterans, and so they reach out to me and we'll say, hey, Matt, I'm starting up a business. Do you have a need for this? And we talk. Maybe I don't have it at the time, but I might be growing into that area.
That's awesome. What path do you use specifically to reach out to the veterans?
Through podcast, there's been a couple phenomenal organizations that help veteran entrepreneurs. One of them is at Syracuse University called ivmf. So I graduated from their EBV program at FSU last summer. And so that's one of my networks. So I reach into them to find out what other companies are out there that are either in the concept phase or building phase or maybe, you know, they, they have a large company and I will say I'm in need of this type of, you know, this is my requirement. They'll say, oh, this is, we've got X, Y and Z people here. And so then I'll get an email introduction to these people. And that's a main, main source. Another one very similar to IVMs is called Veterans Entrepreneurship Program and taught at different locations. I went to the OSU1 in Oklahoma, but they have it University of Florida, they have it at Tennessee, they have it at Grand Forks. And so, and it's a free program. You don't pay for the food, the travel, the hotel and the free education.
So great option. Yeah, yeah. So please do go check out all those. Just Google veteran entrepreneurs. And there's great things. And then there's a bootcamp too, I saw, which was pretty cool, like a three day weekend boot camp thing. So, yeah, some incredible stuff. But that Syracuse program, I'm glad you mentioned you had gone through that. That seems really amazing. So I have two why do you do it? Questions. The first one was tied to what we just talked about. Why do you hire veterans?
For one, I want to. Because I'm a veteran myself. That's probably the number one thing.
So you can act. Sure, yeah.
Just because they're a veteran doesn't mean you're going to get hired. It basically means you have a guaranteed interview and a guaranteed chance with me. And then there has to be a little bit more. You have to be able to show yourself. I also like working with boutique and smaller companies. I think it's great to grow together. There's a few companies I've worked with for several years and it's been fun to see them grow. We've. And then I've also given them contacts and sources of other things. And it's been kind of a quid pro quo process and it's been fun. It keeps me. And I think it'll keep me in tune with the military. I love the military.
Yeah.
Even though I'm going to retire this summer, I know that I want to stay in touch with the military somehow. And I think this will be my way is being in that community, that brotherhood in the air force, the wingman program, you know, the battle buddy, you know, I mean all those terms that's I want to keep in that and so I will stay somehow attached to it. So that's awesome.
Exactly why I'm blessed to do this show. Exactly. Well said. My other question was why did you start your company? Like why rollers? Why did you do that?
To be honest, it was all by chance. Like I said, I started in the garage and I wish I had a large grand strategy that I thought I'm going to name and sell it and get all of these sales. But a lot of it was by chance and it was just recognizing the next opportunity along the way. Very small opportunity. You know, for example, when I had a small mom and pop store that asked would you wholesale me some of your games? I had no idea what that even meant and what point even meant. What did I need margin wise on my end and their end. They instructed me and taught me through that and it's just like. It's almost like a lily pad. I went from one step to the next step and I just really enjoyed it every time. It gave me a lot of energy and that's why I keep going down this path of entrepreneurship because it's been fun.
That's awesome. We're coming near the end of our time, Matt and I gotta have you back on for a ton more questions I have. So everyone should go to rollers.com and check out this amazing game. There's videos on there of people playing it, which is good. Even I could learn that game.
How else though can they help or get involved?
Take a look at the website rollers.com and if there is, I love to share and I would love to share my experiences with anyone and help anyone along the way. If anyone's stuck in a rut and they need some direction. I've got patents on the game. So you know it's an intellectual property question. If it's distribution, maybe it's price point in anything. I'd love to connect with anyone out there. Military, firefighters, policemen, anyone. Reach out to me and if you ever have any ideas, I love your ideas. So please send them.
That's awesome. I was hoping you'd say that. That is amazing because everyone has a Rollers inside them. And again regardless of what it is, it's the process. Right? So now that you've done Rollers you can do the next Tesla because you understand the process. So that's awesome. That's awesome. Matt, thank you so much man.
No problem. Thanks so much for having me on.
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