PayIt gains $25M follow-on investment from early backer Weatherford Capital
May 31, 2019 | Tommy Felts
A Tampa-based venture capital firm run by three brothers sees investing in Kansas City’s PayIt as part of its long-term strategy.
Weatherford Capital first backed PayIt in 2016, through a $4.5 million Series A round led by New York-based Advantage Capital Partners, and followed by Weatherford, Royal Street Ventures, the Missouri Technology Corporation and Five Elms Capital.
The firm confirmed to Startland this week a follow-on investment of $25 million for the Kansas City GovTech innovator, which is led by co-founders John Thomson and Michael Plunkett.
Specializing in GovTech applications that better connect government to its constituents, PayIt made news in 2018 thanks to major partnerships with the State of Kansas and the Unified Government of Kansas City, Kansas. Its iKan app notably allows Kansas to skip the line at the Department of Motor Vehicles.
PayIt was named one of Startland’s 10 Kansas City Startups to Watch in 2017 and 2018.
“As investors, we seek out quality teams, leaders, and healthy cultures, not just assets and good ideas,” reads the investment firm’s website. “We believe that through long-term partnerships with purposeful capital and high-quality companies we will produce outcomes that promote human flourishing.”
Driven by Will, Sam, and Drew Weatherford, the firm has a nationwide focus on middle market firms with enterprise value of $50 million or more.
In March, PayIt made headlines with a more than $100 million investment by New York-based Insight Partners, which provided an exit for investors within the KCRise Fund.
Click here to read about the game-changing investment for PayIt and Kansas City.
“The company [PayIt] happens to be in Kansas City — Investors expect a return. They’re looking for big, scalable, durable businesses,” PayIt’s Thomson said at Startland’s May Innovation Exchange event. “You’ll hear the phrase ‘escape velocity’ — those that can turn into the next Fortune 500 company in a market or a category. It’s all about the execution of the business, the growth trajectory and how investable is that team and business.”
Meeting with more than 85 firms in its most recent funding push, however, PayIt saw rising interest not only in its GovTech offering, but in its hometown backing, he acknowledged.
“There’s a broad awareness of Kansas City, this ecosystem and this environment — and that it’s been on the rise,” Thomson said.
Featured Business

2019 Startups to Watch
stats here
Related Posts on Startland News
Here’s how a new data dashboard could help KCMO redirect funds to small businesses
A new data dashboard built to better understand Kansas City’s business needs — and guide the city’s response — is not only revolutionary for the metro, said Nia Richardson, it could be the first of its kind, period. Small business advocates already are calling it a win. “I don’t know of any other city or playbook…
Modern world requires entrepreneurs to think like creatives, says KU’s Innovator in Residence
Editor’s note: The University of Kansas’ School of Business is a partner of Startland News. LAWRENCE, Kansas — Building a skill set around creativity is critical to entrepreneurship — especially at a time when careers can be short-lived, said Josh Wexler. “Jobs are no longer for life,” explained the Innovator in Residence at the University…
Grantmaking reboot ‘just one piece of the larger puzzle’ in Kauffman Foundation reset, CEO says
Overhauling the Kauffman Foundation’s grantmaking strategy aligns with a broader, holistic reset for the influential Kansas City organization, said Dr. DeAngela Burns Wallace, emphasizing org-wide moves to deepen the impact and dialogue sparked by its giving. “We’re still engaged in the work happening locally, regionally, and nationally,” said Burns-Wallace, president and CEO of the Ewing…

