Today we’d like to introduce you to Michael Callahan.
Hi Michael, thanks for joining us today. We’d love for you to start by introducing yourself.
I came from a white-collar engineering background. When COVID hit and I was sent home, my work became almost entirely remote, and I didn’t handle that very well. My days felt rushed and impersonal — back-to-back meetings, spreadsheets, constant pressure — and I realized I really missed being out in the world and around other people.
I started looking for something more tangible and local, something that would get me out from behind a screen. Vending appealed to me because it was practical and accessible — I could start small while still supporting my family. The transition to vending also meant stepping into a completely new industry and figuring things out through trial and error; this was a little scary to think about, but the idea of applying my critical thinking and problem solving in an entirely new arena was pretty exciting, too.
The learning curve was steep, especially early on. I lost a couple of customers in that first year, which was humbling, but it forced me to build resilience and focus on what I can control: showing up, solving problems, and doing the work well.
Today, the business is built around being reliable and taking care of people — both our customers and the small team I work with. It’s not flashy, but it’s real, and it fits the kind of life and work I wanted to build.
Alright, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Not at all. The early days were pretty bumpy. I was coming into an industry I didn’t know, learning everything on the fly, and trying to do it while still supporting my family. There was a lot of trial and error.
One of the bigger adjustments was learning how to spend my time. In a W-2 job, even at a high level, there’s usually some structure — goals are set, priorities are defined. Owning a business is the opposite. It’s a blank canvas, and that was uncomfortable at first. I had to learn to constantly ask myself, “What’s the most valuable thing I can be doing right now?” and live with the fact that there isn’t always a clear or consistent answer.
Losing a couple of customers early on was also tough. I take a lot of pride in my work, so even when I didn’t feel like I’d done anything wrong, it forced me to accept that not every loss is a failure. That was a humbling but important lesson.
Another ongoing challenge has been that vending is often treated as a commodity, especially within larger organizations. Decisions are sometimes made far from the people actually using the machines, which makes it harder to build relationships or show the care that goes into the work. I’ve learned to focus on partnerships where consistency, responsiveness, and trust still matter.
It hasn’t been smooth, but those challenges shaped how I run the business now — steady, thoughtful about how I spend my time, and focused on doing right by people.
Thanks – so what else should our readers know about Jacksonville Vending Company?
We’re a local vending company serving mostly blue-collar workplaces — shops, plants, warehouses — places where people work hard and appreciate things that are done well and done consistently. On the surface, what we do is simple: we place machines, keep them stocked, keep them clean, and make sure they work.
Where we’ve found our footing is in how much attention we pay to the details. Vending is often treated like a set-it-and-forget-it service, but we’re pretty hands-on. I care a lot about what goes into the machines. I enjoy curating the product mix and rotating items so things don’t feel stale. If a location wants the same item every week, we’ll absolutely do that — but otherwise I like keeping things fresh so people actually want to check the machine and see what’s new.
Another part of our approach is pricing. I don’t like selling on price, but I do care deeply about it. I work hard to keep prices as low as possible because I know the value of a dollar, especially in the kinds of workplaces we serve. If someone is going to trust me with their business, I want them to feel confident that I’m being a good steward and charging an honest price.
Brand-wise, what I’m most proud of is that the business reflects how I think about work: show up consistently, pay attention to the details, and take care of people. We’re not trying to be flashy or the biggest player in the space. We want to be known as the vending company that’s dependable, fair, and easy to work with — the one you don’t have to worry about because they just get things handled.
What do you like and dislike about the city?
What I love about the city is the density and variety of its local economy. Driving between customers and looking for new ones, I’m constantly struck by how many small, often unseen businesses are quietly supporting the whole place. On just about every street there are shops, warehouses, and service businesses doing real work without much flash, and it’s honestly an honor to play even a small role in keeping that moving.
What I like least is the pace. It can feel like there’s always pressure to move faster — to grow quickly, to say yes to everything, to chase momentum for its own sake. As a business owner, that creates a constant tension between expanding and being intentional.
What I’ve learned is that the city feels at its best when it slows down enough to be relational. Spending time with customers, you can tell who’s in it for the long haul — who values their people, who treats others with kindness, who’s building something durable rather than flashy. Those moments make the city feel smaller, and more human, and that’s the version of it I appreciate most.
Contact Info:
- Website: https://www.jacksonvillevending.com
