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Writer's pictureJohn Lim

MF 114 : From Flying Jets to Scaling a Multi-Million Dollar Vending Business, with Matt Miller

Updated: Jun 17, 2022




Moving Forward is also available on Apple Podcasts, Stitcher Radio, Google Podcasts, Spotify, and Amazon Music.


Matt Miller is a former Air Force pilot turned entrepreneur. Today, you will hear Matt’s extraordinary story of how he founded School Spirit Vending and scaled it into a multi-million dollar business.


Successes at a glance:

  1. Graduate of the U.S. Air Force Academy.

  2. Former Air Force Pilot.

  3. Founder, School Spirit Vending, a company dedicated to providing vending machines to schools to help bolster fundraising efforts.

    1. Scaled it to a multi-million dollar franchise.

Setback failure or time when things fell apart:

In 2008-09, the economy crashed which greatly impacted Matt’s then sidepreneur venture, selling vending machines. Since vending machine revenue is largely driven by foot traffic to local businesses, a downturn in the economy meant that people weren’t going out; directly impacting his revenue stream. As detailed in the “aha” section below, Matt had spent time, money and lots of sweat equity building up a business w/ machines at 120 locations. At that time, this side venture was bringing in double what his day job was paying him but the downturn in the economy put all of that in jeopardy. At one point, Matt was delivering pizzas to raise seed capital bc as he put it his credit “stunk” and he couldn’t get a business loan. Matt was working at a demanding day job and struggling during nights and weekends to make his side business work; all the while caring for a family that includes three kids. So what kept Matt going? How did Matt end up a success story rather than a cautionary tale? To understand this, it’s important to understand that Matt’s pivot wasn’t simply a one and done. It was a long process, filled w/ many hard decisions, strategic planning and a lot of hard work. As Matt reveals, he didn’t just have one “aha” moment but many that grew and evolved.


The “aha” moment that sparked a pivot:

Although Matt served in the military for nearly a decade, flying planes, he never liked being told what to do! Around the midway point of his commitment to the military, Matt started thinking about a post-service career and life. Initially, Matt decided to pursue a job in the corporate space; transitioning to medical sales and then advertising, where he spent nearly a decade. While Matt found tremendous success and joy in advertising, as he notes in our conversation, “the rules were always changing” and at the end of the day, the stockholders were the number one priority over the employees. Moreover, Matt’s plans for his family’s wellbeing were continually disrupted by changes in the company’s comp plan and increasingly, Matt found himself on “the losing end of the stick.” This continued to spiral until one day, a decision by his then boss put Matt and his team in a “really deep hole, financially.” Knowing that the comp plan was constantly changing, Matt realized that it just wouldn’t work out in his favor, long term. It was at that point that the entrepreneurial spark “kicked in.”


Once the entrepreneurial bug bit, the next step was to figure out “how to make ends meet.” A characteristic you will notice about Matt is that he extremely scrappy and tenacious; he’s not afraid to get his hands dirty. Matt did everything from collecting aluminum cans to selling used books online. There was nothing glamorous about this: it was finding roots in entrepreneurship by trying different things and sheer hard work. One of the tenents that Matt had adopted was the idea of creating passive income streams, a notion he learned from Robert Kiyosaki.


Matt pondered a question: if he could do well enough as a sidepreneur to pay the bills and keep a roof over his family’s head, could he create something that could afford a lifestyle, free from the hustle and bustle of working a day job. Fortuitously, a friend of Matt’s at church happened to mention that he and his daughters had started working w/ local businesses, providing gumball machines. At that moment, Matt had an epiphany. The gumball machines were putting into practice Kiyosaki’s philosophy of building passive income streams.


Warren Buffett had a similar revelation when he started his first pinball machine business as a teenager.


From there, Matt started w/ his first used candy machine that he bought off eBay. Over the next year and a half, Matt grew his business to 120 machine placements in and around Houston. Matt also started branching out from candy to toys, stickers, and temporary tattoos. Matt describes this as quite the “accident” and not an intended career path, certainly not for someone who used to fly jets!


Increasingly, this side venture starting taking up all of Matt’s nights and weekends. Meanwhile, Matt was keeping his day job. Although he was bringing in double his day job income from this side venture, he made sure to continue having a stable income to provide for his family, taking a strategic approach. You might wonder why Matt took a more conservative path towards full-time entrepreneurship. Although the business grew considerably, as noted above, the downturn in the 2008-09 economy put that side venture in serious jeopardy. Matt had seen friends who had found initial success in ventures such as multi-level marketing make bad decisions that put them in serious financial jeopardy. So, while Matt was very much an entrepreneur at heart, he was also sensible in how he made decisions: putting his family’s short and long-term well-being first and foremost.


As Matt was contemplating how he was going to weather the storm of a downturn in the economy w/ fewer patrons to local businesses (which also housed his machines), another fortuitous event occurred that changed everything. With the kind of timing you might only see in a movie, there was a knock on the door. Several neighborhood kids were going door to door selling goods to raise funds for their school. And that’s when Matt had the biggest aha moment that changed everything. Matt being a parent, had kids that were of similar age and the one thought that kept running thru his mind is that he would never let his kids go door to door, selling things to strangers, unaccompanied by an adult. This led to a crossroads of opportunity that met several market needs:

  1. Matt needed to stabilize his vending machine business which was suffering from decreased foot traffic at local businesses.

  2. Schools needed to fund raise.

  3. Parents have an interest in keeping their kids safe.


The convergence of these three factors led to the next phase of Matt’s vending machine business, which was the formation of School Spirit Vending. Matt could redirect the vending machine business towards schools which would simultaneously provide Matt w/ a large, untapped market while creating a scalable fundraising solution. Matt could also utilize his background in print advertising to create custom stickers for the schools to sell in the machines.


This new direction opened up tremendous opportunities for Matt, ones he couldn’t foresee at the time. While Matt was initially driven by a need to salvage his vending machine business, he never imagined that School Spirit Vending would lead to a franchise. Before long Matt had friends and family interested in learning and becoming involved as well. As Matt shares, this was a big reveal for him: he was not only validated by the schools (his market) but now by people around him who he respected and looked up to. This led to the next phase of his business, a licensing and distributorship model: teaching others the business model that was proving so successful. Soon this spread from Texas to other parts of the country. And that’s when Matt had his breakaway “aha” moment. Once scale had been introduced into his venture, the gains had increased so significantly and the risk had become so spread out that it no longer made sense for him to continue working in his day job and that’s when Matt made the full leap. Equally incredible, Matt left his job at a time when they things were starting to look up and his team was doing really well. Matt’s boss was so floored by his announcement that he first offered him a 3-month sabbatical to “clear his head” and when he couldn’t convince him to stay, allowed him to move to Ft. Worth and work remotely to help the transition in exchange for staying one month longer.


Matt shares this invaluable insight. Not once did he let his work ethic or devotion to his day job slip. He put in 100% up until the last day which is why he was so respected by his boss. Matt’s integrity is what allowed him to start a side venture in the first place and leave on his own terms bc there was never any doubt as to his commitment. As long as Matt put in 100% during the day, the company didn’t own him during his nights and weekends.


Moreover, Matt knew his job was never 100% secure. He could lose it at any time from a layoff so it was in his best interest in continue building his side venture and put as much effort into that as his day job. Not easy but as Matt shows, it can pay off in huge dividends!


So what kept Matt going? As Matt shares, there were several years when he was stretched really thin but what kept him going and moving forward wasn’t where he was but the vision of where he wanted to be. Matt knew that his biggest aspiration was a lifestyle that wouldn’t be dictated by a company only interested in shareholder profits or a comp plan that was out of his control. Matt’s entrepreneurial journey was more about freedom than money and at the heart of it, that’s what kept Matt going.


The beauty of Matt’s story is that it builds slowly and logically, from lessons learned, experiences and from witnessing the mistakes others have made. The biggest takeaway from Matt’s story is that you can start something entrepreneurial. You can explore a side venture and there are incredible opportunities to grow something that can take you into a whole other stratosphere. But, there are risks involved and to mitigate those, you can take a calculated and strategic approach that won’t put your livelihood and the well-being of your family in jeopardy. It’s not easy and as Matt shares, it took a lot of nights, weekends and many frustrating moments and setbacks along the way. But not only did Matt create a successful business that created a lifestyle of freedom, he did so w/o having to risk his livelihood and his family’s well being. As w/ flying jets, you can be dangerous and risky or sensible and strategic. As Matt proves, being the later doesn’t prevent you from reaching great heights and moving forward.


Knowledge bursts:

  1. Resource or cultural experience that inspired Matt to move forward:

    1. ‘How to Win Friends and Influence People’ by Dale Carnegie (Paperbook | Kindle): Matt cites this as having the “worst’ title but the best insights towards understanding people, relationships and the power of listening.

    2. ‘The 12 Week Year’ by Brian P. Moran (Hardcover | Kindle): talks about the importance of focus and using “short sprints” to make real progress in your projects and endeavors.

    3. Robert Kiyosaki.

    4. Matt also loves conferences. As his team grew, Matt realized that the speed of the team’s growth and development is all determined by the growth of it leader. Thus, Matt puts significant investment into his own personal development by attending conferences and events held by masterminds like Seth Godin and Dave Ramsey. Notably, at a Dave Ramsey event, Matt met Aron Walker, a highly successful entrepreneur who has built and sold 12 businesses. Shortly after, Matt hired him as a coach.

  2. Favorite app / website / resource or productivity hack:

    1. Rev.com: a transcription app. Matt loves to talk but finds writing a challenge. With Rev, Matt can create multiple blog posts by speaking the content and editing it later.

    2. YNAB (youneedabudget.com): great app for personal and business budgeting that syncs across all platforms (computer, tablet, smartphone).

  3. How Matt recharges when facing a roadblock or challenge:

    1. Shut things off for a while. The beauty of being an entrepreneur is being able to take the time to do so. Recently, Matt visited his son in college and shut off all of his devices for three straight days. Matt finds those moments when he can give 100% to his family to be the best way to recharge and reboot. Matt also shares that he can do this bc he has surrounded himself w/ people he can trust to run the business during those days when he needs to step away.

Support the Podcast:

  1. The Corporate Cliches Adult Coloring Book: makes the perfect stocking stuffer or white elephant gift.

  2. Try out Audible (affiliate link).

  3. Try out Amazon Prime (affiliate link).

Advice to past self while going thru a difficult time:

At a low point, Matt was deeply in debt and had to go to consumer credit counseling to see if he could get a bunch of credit card interest rates dropped bc he couldn’t get a payday loan. Thinking through it all now and reflecting on his own journey, Matt’s mantra is to “think bigger” and “dream bigger” than you can ever imagine. Even w/ all of his success today, Matt continues to work at this. When he hired Aron as his coach, Matt had achieved huge success and was … bored. Working w/ Aron, Matt is now pushing on to the next level, thinking and dreaming bigger than even he could imagine w/ all of his success. Moving Forward listeners, it never stops. Whatever you imagine your goal is, your “walk-away number,” your success line, it’s simply a place in your journey. Today, Matt has reached success. Now, he is focusing on significance. As Matt shares thru his extraordinary story, reaching your goals does not have to be (nor should it be), the end to you moving forward.


Parting wisdom (in a few words):

“Get Started Now!”


Connect with Matt:


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