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In the heart of Southwest Florida, Matthew Rainey is redefining what it means to hustle in the vending industry. As the founder of Surpass Refreshments, Rainey now operates over 550 vending machines and 15 micro markets across Lee, Collier, and Charlotte Counties, with revenue approaching $4 million annually. But his journey didn’t start in a boardroom or a business class. It began in the grease-stained trenches of an auto mechanic’s shop — and with an unwavering determination to rewrite his future.
Trading Tools for Snack Shelves
After graduating high school, Rainey entered trade school and built a career as a skilled auto mechanic. Yet, the physically demanding nature of the job eventually had him questioning its long-term sustainability. “I knew I couldn’t do this kind of labor forever,” he shared. The vending industry, with its blend of physical and logistical work, caught his eye as a more sustainable path.
His first vending machine was placed in the corner of a near-empty used car dealership lobby. “There was basically no foot traffic, maybe five people a week,” he said. “But every time someone bought something, it felt like a win.”
An Apartment Turned Warehouse
From that humble start, Rainey went all-in. He drove to Miami to buy three used snack machines, then began promoting his business on social media. Operating out of a Ford Focus wagon, Tuesdays became vending days. He unloaded his tools, loaded his vending machine snacks and beverages, and transformed his living room into a warehouse.
He and his wife, Paige — his high school classmate and now his biggest supporter — became regulars at Publix and Walmart, clearing shelves during BOGO sales and hoarding pallets of drinks in their living space. “We didn’t have a storage unit. Our apartment was the storage unit,” Rainey laughed. “We were hauling Gatorade by hand at 4 a.m. It was chaotic, but it was ours.”
At first, he even refused to use a dolly. “I’d carry everything by hand. Multiple trips. Everyone said, ‘Get a hand truck,’ but I was too stubborn.”
How He Scaled Surpass Refreshments
Rainey never made cold calls or knocked on doors. “It was all word-of-mouth and social media. I just kept showing up and doing the work,” he said. That reputation built momentum.
He acquired several smaller routes, each with 20 or so machines, and hired his first helper. Without route management software, Rainey would assess inventory at the client site, then call his assistant to pull the right products from the truck. It was messy, but it worked.
Over time, he scaled his operation from a Focus to an Econoline van to box trucks. Today, Surpass runs four route trucks and a delivery truck. His mechanical background allowed him to maintain and repair much of his growing fleet.
Throughout all of it, Paige remained by his side. Whether attending NAMA with him, sitting through Cantaloupe classes, or riding along to late-night machine repairs, she’s played a pivotal role in building the company brick by brick.
Making Tech Indispensable for Growth
The business hit a new stride after Rainey attended a Cantaloupe conference in Las Vegas. There, he adopted ZippyAssist for customer service, Cantaloupe readers for cashless payments, and Seed Pro VMS to manage inventory and logistics.
With ZippyAssist, Rainey aimed to give his customers a vastly improved experience over the old-school “call an 800 number and hope someone picks up” approach. The easy, text message–based communication platform allowed instant refunds and fast feedback, setting Surpass Refreshments apart from competitors and solidifying Rainey’s commitment to superior customer service.
On the hardware and operations side, Cantaloupe became an integral part of the business. Rainey equipped all his machines with Cantaloupe card readers, allowing for seamless cashless payments — a must in today’s marketplace. He embraced Cantaloupe’s Seed Pro VMS, which enabled precise prepicking and route optimization. Gone were the days of guessing what to load into a truck. With real-time data, Rainey’s team could plan their day with surgical precision, reducing waste and increasing efficiency.
He also invested in Pick Easy, another tool from Cantaloupe, which streamlined the packing process even further, ensuring every product was accounted for before hitting the road. The complete integration of these systems has transformed Surpass Refreshments into a tech-forward operation that’s efficient, responsive, and scalable.
“Before VMS, we were a rolling warehouse,” he said. “Now, we prepick and plan. It changed everything.”
Markets, Mergers, and Motivation
After two eye-opening trips to the NAMA show, Rainey doubled down on micro markets and smart coolers. Surpass has installed 15 markets in just eight months, acquired a local vendor with 75 machines, and has three smart stores on the way.
“No one in my area has smart stores yet,” he said. “We’re going to be first.”
But not every venture ends in victory. A recent micro market installation was removed within 24 hours — despite being fully branded — because upper management feared it would “tempt employees to steal.”
“That was tough,” Rainey admitted. “If I didn’t trust my team, they wouldn’t be my team.”
Five Principles for Future Founders
Having bootstrapped every inch of his success, Rainey offers the following advice to aspiring vending entrepreneurs:
- Over-deliver: Always exceed expectations.
- Put in the hours: This isn’t passive income — it’s full-contact entrepreneurship.
- Fix it now: If something breaks, be the one who shows up.
- Standardize machines: Stick to one or two brands to simplify repairs and stocking.
- Plan for failure: Have backups for trucks, machines, and staff.
Vending: The Industry of Opportunity
Matthew Rainey’s journey — from vending out of a Ford Focus to managing a high-tech, multimillion-dollar enterprise — is the kind of story that defines modern entrepreneurship. It’s raw, real, and relentlessly driven by heart.
Matthew and Paige, who first met in high school 27 years ago, reconnected in 2013 and have built more than a business together. They married in January 2025, and their shared devotion to each other and to Surpass Refreshments is woven into every success and every late-night repair call.
“This industry gave me an opportunity,” he said. “And I’m running with it.”
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Neil Swindale is the CEO of Vending Connection, a GoGo Refresh brand. With 30 years in the refreshment industry, he has built (and sold) companies that elevate the customer experience through smarter technology, better service, and authentic storytelling. Originally from New Zealand, he recently sold a leading marketing company in the space. He’s now focused on growing the industry by uncovering and sharing more stories like this.
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