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
Frustrated by the fit, this traveler-turned-swimwear founder crafted 10 pairs himself; now his trunk show is going global
Opening a popup swimwear store in one of Atlanta’s most upscale malls represented a surge of momentum for Tristan Davis’ high-end brand that began not on a beach or a runway, but in Kansas City’s tight-knit startup community. “We’ve gone from an idea in a handmade bathing suit to a high fashion mall in less…
Harvesting opportunity: How a KC chicken chain turned a strip of parking lot into its latest ingredient
Months before snow blanketed Kansas City this week, Todd Johnson transformed a weed-filled, unusable portion of parking lot at his Lenexa restaurant into a flourishing garden that serves up fresh produce used in kitchens at all three of his Strips Chicken and Brewing locations in Johnson County. In its first season, Moonglow Gardens — as…
AI evolved faster than rules to protect people; this founder wants to code ethics back into the tech
Amber Stewart sees what many overlook in artificial intelligence, she said: the human cost of unregulated technology that can manifest as anything from sexist and racist outcomes to outright theft from willing and unwilling members of the public. “I’m not afraid of the tech,” said Stewart, founder and CEO of GuardianSync. “I’m afraid of unfettered…
A romantic hideaway (for you and a book): Entrepreneur’s heart for reading opens store on Independence Square
America Fontenot didn’t plan to launch her new Independence bookstore on national Small Business Saturday — the busiest shopping weekend of the year — but renovation delays just kept pushing back the opening, she said. So while many small shops were offering Black Friday-adjacent deals to get customers in the front door, Fontenot’s The Littlest…

