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Madison Startup Carepool Helps People With Disabilities and Older Adults With Transportation


98-year-old senior male getting into a car.
Credit: Maki Nakamura/Getty Images

Madison-based Carepool has received $150,000 in seed investment capital from Jumpstart Foundryan accelerator-turned-healthcare innovation fund in Nashville.

Carepool is a software platform that connects riders with disabilities and older adults to specialized transportation services. The company works with Managed Care Organizations; the Department of Workforce Development; Include, Respect, I Self-Direct (IRIS); and private payers to automate and facilitate transportation booking.

The company compares its software to flight and hotel booking company Expedia, combined with real-time text notifications similar to Uber.

With the investment from Jumpstart, the specialized transit company joins 16 other early-stage startups to round out the fund’s 2019 portfolio, with each of the companies receiving a $150,000 backing. Out of nearly 300 applicants, Carepool is the only Wisconsin company in this year's cohort.

Jumpstart Managing Director Eller Mallchok said Jumpstart was intrigued by Carepool’s business concept because it regularly pairs experienced drivers — including those with CNA, caretaker or health certifications — with riders, and operates in rural areas where transportation access is often lacking.

“That’s what makes it stand out,” Mallchok adds. “That and its technology.”

CEO and Founder Josh Massey launched Carepool in 2017. An experienced entrepreneur, Massey previously owned two other companies: BlueLine Consulting LLC, a technology staffing company, and RideAlfred, a black-car rideshare service staffed by professional drivers.

When the state of Wisconsin shifted its regulations on Medicaid fund disbursements tied to specialized transit services, Dane County agencies began reaching out to the area’s entrepreneurial networks to help them improve efficiencies within the program.

Massey, newly returned from Chicago, responded to the call.

“There was a big change in how Dane County had to adjust funding and how they found their providers, and it created the perfect opportunity to turn to innovation,” explains Massey. “I realized there was a bigger problem to solve,” than luxury rideshare, he says.

Massey took to Facebook to announce that RideAlfred was on hold, and turned his focus to creating independence for people with disabilities and the aging community. For the next year, Massey and his small team worked with government agencies to understand the specialized transit environment, and — leveraging his experience in staffing and SaaS — they set out to develop a software platform to help generate access to mobility.

“I got involved in this world, and it made me realize this was something that I wanted to pursue—leading things that had not been done,” Massey said.

Still, there was a learning curve. Beyond booking services, the software had to authorize rides, automatically bill Medicaid, schedule drivers, and track spending. He enrolled in gBeta’s 7-week accelerator program, fine tuned his business concept, and eventually built a prototype.

“I leaned on every software expert I knew,” he said.

Carepool caters to people who use the rides for employment, errands, meetings and social gatherings. Unlike other similar services, Carepool operates day and night, and is available for round trips across county lines.

Most riders are on Medicaid and use care managers to book rides on their behalf. Depending on their program status, a budget is determined and allocated for transportation throughout the month. Care managers then use Carepool to connect riders with consistent drivers, enabling family members and riders to build trusting relationships with the drivers over time.

“We’re not a dispatch model,” Massey said. “We only put [drivers] out there when there is work.”

So far, Carepool is available in greater LaCrosee, Dane and Waukesha counties, and will soon expand into Eau Claire, Janesville, Beloit and Fox Cities.

In an industry projected to generate more than $138 million in specialized transit services in Wisconsin alone, Massey says Jumpstart is just the first investor to take interest in the company. Following Jumpstart’s $150,000 investment, he says the company has received several verbal commitments and is rapidly closing in on a $500,000 seed round.

“We’re more efficient than a traditional taxi, have higher ratings, and are more cost-efficient,” Massey says. “We’re bridging a gap.”


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