ZippyZen: Filling Hearts, Souls, and Stomachs With ZippyMeals

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More than 10 years ago in January of 2008, the first lines of code were written for what would eventually become ZippyMeals.

“One winter, I got really sick for a week and had to stay home from work, and I just decided to create the software prototype that morphed into what ZippyMeals is today,” recalls John Cleveland, founder of ZippyZen.

ZippyZen provides ZippyMeals, a cloud-based software logistics solution for Meals On Wheels, a category of nonprofit organizations that deliver meals to the homebound elderly. The average nursing home in the US costs $253 a day, coming to an annual bill of over $92,000 per year for a one person room. In comparison, the average annual cost to provide 250 days’ worth of meals through a Meals On Wheels program averages $2,765 per person. Meals On Wheels services reduce the cost of housing and caring for seniors who can still live at home by delivering meals directly to them.

The original idea for ZippyMeals came from John’s experiences as a volunteer with Meals On Wheels beginning 11 years ago. “I started as a volunteer driving for Meals on Wheels and had some difficulties driving routes because I was given outdated maps and directions that were hard to read and understand,” John says. “I feel like not just Meals On Wheels, but a lot of nonprofits in general that have some sort of social mission are often stuck out there in no man’s land without good systems that can support their processes.”

John, a software engineer by trade, took the prototype to several local Meals On Wheels offices, where it immediately gained traction within their infrastructure on a day to day basis. “A couple years later, we realized that the prototype was still working, and it was critical to their success and operations as an organization,” says Dawn Cleveland, John’s wife and business partner for ZippyZen. “That’s when we saw that this idea could really make a difference in the world, so we decided together to make it happen.”



Dawn had some unique insight on her and John’s ability to work together as both life partners and business partners. “It’s interesting working together as a married couple, dealing not only with the business struggles but running a family at the same time. Figuring out how to juggle that in a way so that both can be successful has been a great journey,” she reflects.

For John and Dawn, though, this is worth the effort. It has also given them a way to connect on a deeper level. “I’ve learned when to push and when not to push,” Dawn says. “You have to realize each other’s limitations, but know that sometimes, you can push someone past their limits -- in a good way.”


On their entrepreneurial journey, John and Dawn have accumulated quite a bit of expertise in the area. When asked what they would tell a potential entrepreneur, they both had answers ready. “The joy of entrepreneurship is creating something from nothing that’s your own vision, and building that thing to see it through into the world,” John says. “But I don’t see how you can do that without just working really, really hard. You can’t be the kind of person who says, ‘Oh, I didn’t get this done today, I guess I’ll just put it off to tomorrow.’ You can’t do that. You have to be moving mountains all day, every day.”

Dawn decided to give advice on advice. “Be open to listening to everybody, but do not let everybody tell you what to do,” she says. “That’s the thing I think entrepreneurs struggle with the most. To me, your job as an entrepreneur is to make sure that the vision in your head actually happens. Sometimes, that means being open to other people’s ideas, but they have to resonate with you. If it really doesn’t resonate, it’s not going to work. You can’t let the tail wag the dog… but you also can’t do it by yourself.”


The most rewarding experience for the ZippyZen team? Dawn and John both instantly agreed on their favorite experience: demoing their software to Cindy, their “Gold Star customer,” as John puts it. “As soon as Cindy sat down with it for about 30 seconds, she started jumping up and down saying, ‘Oh my gosh, this is awesome!’ She saw the vision,” Dawn says. “I wasn’t even there to witness it, and even I’m energized by it because John is so energized by it.”

“It was validation for years and years of work, you know?” John says, shaking his head and smiling.  “I’m very, very proud of what we’ve done with ZippyZen. Growing up, I was not that kind of person; I left a lot of things incomplete. But even though we still have a long road ahead of us, I think I can look back at this and say that I did finish it. We have paying customers: it’s working in the real world and real people are benefiting from it. I made it happen, and I saw it through to completion.”

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John and Dawn had a bit more to add about the difficult but wonderful world of working with nonprofits. “20 years from now if I look back and say, ‘Well, I made a lot of money, but I didn’t really do anything that helped the world,’ I think I’d be pretty dissatisfied,” John says. “Instead, what I want to say is, ‘I really made a positive difference on the world, and I guess I made an okay amount of money.' Then I’d be satisfied.”

Dawn concurs, adding, "There are a lot of smart, well-educated people working at nonprofits for half of what they would make elsewhere because they believe in the mission. You probably won’t become incredibly financially rich serving a nonprofit, but your spirit and your heart will become rich and full because you know you’re making a difference every day.” 

“Those values have always been the driving force for us as a family, and for ZippyZen as well,” John concludes.


About The Team

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John Cleveland grew up in Central Virginia and received a B.S. in Physics from the College of William and Mary. Since then, he has worked as a software engineer for over 20 years in many different capacities. John volunteered as a driver for Meals on Wheels starting in 2007, and served 6 years on the Board of Directors for his local Meals on Wheels office.

Dawn Cleveland grew up in Northern Virginia and received a B.S. in Biology from the College of William and Mary. She has a background in tax and financial services, and has also worked in training, developing courseware for scientific equipment. Dawn has volunteered with Meals on Wheels since 2011 and Boy Scouts with her sons since 2013, serving as a den leader and Cubmaster.

John and Dawn have “three awesome boys who play soccer and occasionally go to school.” Their boys each have helped deliver meals since they were age 2, and actively helped test the software, mapsand directions. The Cleveland family moved to Charlottesville in 2005, where they still live.

If you want to learn more about ZippyZen, their ZippyMeals software, and their social mission, you can find them at or request a demonstration at


About the Author

Christopher Nelson is a rising second year at New York University in Shanghai, China. He has experience in business operations as well as legal research and contract work. Christopher is currently interning at the UVA Darden School of Business Innovation Lab this summer as an interviewer and journalist.