The Story of Park Thrive: From a Simple Idea to a New Way of Parking

How two founders turned a real-world problem into a smarter, more human approach to parking.

When you meet Matt and Drew, the co-founders of Park Thrive, you quickly realize they didn’t set out to build just another parking company. They wanted to solve a real problem: parking lots sitting empty or underused while business owners struggled to make the most of their property. Their mission has always been about empowering small and medium-sized property owners and organizations with simple, effective tools to unlock the value of their parking assets.

The idea started to take shape after years of experience in other industries.  Drew had spent more than seven years at a software company, helping small and medium-sized businesses improve operations and increase revenue. He had seen firsthand how technology could transform a business’s bottom line.  Matt came from the travel industry, where good software revolutionized how people booked tours, planned trips, and navigated cities. He had also worked on the sales and marketing operations team for Google Glass, gaining insights into what makes innovation succeed or fail.

When they teamed up, Matt and Drew began exploring industries that were behind in technology adoption. Parking stood out. Drivers were often frustrated with complicated apps and outdated kiosks. Property owners were frustrated that their parking lots generated little or no revenue, or that they were locked into contracts with traditional parking management companies that focused more on issuing violations than supporting owners.

Their original plan was to build best-in-class paid parking software and partner with established parking management firms. But they soon discovered that many of these firms had business operations entrenched in traditional approaches and were slow to adapt to new technologies. They realized that the real opportunity was to go direct to property owners with their own system and approach.

From Alleyway to Nationwide Impact

Their first real-world test came from a woman in Somerville, Massachusetts. She owned two parking spaces in an alleyway that were often occupied by unauthorized parkers. She hoped to earn an extra hundred dollars a month to help with maintenance costs.

Matt and Drew implemented their proof-of-concept system. Almost immediately, someone paid to park. That moment was the spark that led them to believe there was a vast, untapped need for easy-to-use parking revenue management solutions.

What they learned was that thousands of small and medium-sized business owners, nonprofits, and  individual landowners had valuable but underutilized parking spaces. With the right tools, they could transform a cost center into a reliable source of income.

Building a Better Parking Experience

From the beginning, Matt and Drew designed Park Thrive around two goals: help property owners increase their revenue and make parking as seamless as possible for drivers. The company’s revenue share model ensures that they only succeed when their partners succeed, which keeps them focused on real results.

Over time, they expanded their solution into a complete system that combines:

• Parking lot signage that clearly communicates rules and rates to drivers.

• Flexible paid parking software that allows owners to set rates, schedules, and even support complex mixed-use lots.

• Parking validation tools that make it simple for businesses, like restaurants or event venues, to offer free or discounted parking to their customers.

• Support for parking enforcement tools that encourage compliance in a way that recovers revenue without alienating customers.

This approach allows property owners to maintain control of their lots, improve compliance, and maximize their income. By making it easy for drivers to pay quickly—without downloading yet another app—Park Thrive improves the overall parking experience and drives repeat use.

Real Stories, Real Impact

One of Drew’s ’s favorite stories involves a property owner who had reached a breaking point over people using their lot for free. They called in a rush, asking if the system could be live within days. The team designed temporary signage, the owner picked it up at a local print shop, and the lot started generating revenue within 48 hours. The full installation followed soon after.

Another story Matt often tells is about a large, multi-tenant property in Florida. The owner struggled to manage a complicated lot that served a nightclub and other businesses. With clear signage, a streamlined validation process, and effective parking yield management, they brought order to the lot. While most visitors were validated and didn’t pay to park, the remaining 10–15 percent did, creating a meaningful new revenue stream for the owner.

Matt and Drew are especially proud of their work with churches and nonprofits. By helping these organizations implement parking revenue optimization strategies, they have enabled them to retain the majority of their parking income—funds that can be redirected toward their community programs and missions.

People First: The Cofounders Behind the Company

A key reason the company’s culture resonates with partners and employees alike is the character of its founders. Matt and Drew are known for being approachable leaders who encourage curiosity, growth, and problem-solving. Their humor and perspective keep the team focused without losing sight of the bigger picture: building something that genuinely helps people.

Drew lives in Maine with his wife and two young kids. Depending on the season, you can find him running, hiking, skiing, or snowshoeing—always making the most of New England’s outdoors. Matt shares a similar love for the outdoors, often canoeing or sailing in the summer and skiing in the backcountry during winter in Maine and New Hampshire.

Their respect for nature has influenced how they think about parking. By making better use of existing parking lots, they help reduce the need to build new garages or pave over green spaces, contributing to more efficient and sustainable communities.

Redefining What Parking Can Be

Matt and Drew often describe their company as “the Shopify of parking”—a turnkey platform for parking revenue that allows property owners to run their own parking operation with as much or as little support as they need.

What sets them apart is their willingness to take on complex situations, from mixed-use lots to properties with unique community needs. This flexibility has allowed them to become a trusted partner to clients in nearly every state.

In building Park Thrive, Matt and Drew set out to serve the lots most others ignored—the underused, the hard-to-monetize, the overlooked corners of communities. But in designing a system for the undervalued, they ended up creating one that elevated every kind of lot, even those already monetized. What began as a way to make small spaces profitable became a model of efficiency that’s now helping major operations run smarter and earn more. That evolution reflects the heart of their vision: when you build for the people who have the least access to opportunity, you often create something that works better for everyone. It’s a philosophy that continues to guide Park Thrive as they expand into new markets and reimagine what parking can mean for property owners everywhere.

Most importantly, they remain committed to their original mission: make it easy for people to do the right thing, pay to park, and help property owners get the value they deserve from their parking assets.

The Future of Parking Revenue

For Matt and Drew, this journey has never been just about parking. It’s about creating opportunities where others see obstacles. It’s about providing property owners with practical, transparent tools for parking revenue optimization. It’s about making parking less of a headache and more of an asset—for businesses, organizations, and communities.

By blending innovative software, practical signage, responsive support, and a customer-first mindset, they have built a company that continues to change how parking lots operate—and how property owners think about them.