From Pitch Session to Partnership

How a Californian connected with Iowa cofounder

On a cross-country road trip, Paul H. Richardson Jr. stopped in Iowa to memorialize his grandparents and had a life-changing realization. After visiting their hometowns, he then searched for ways to memorialize them online, but ran into roadblocks. This experience inspired him to eventually create Tumbleweed, an end-of-life planning resource.

He discovered that most of those digital resources are hosted by family-owned funeral homes, and many can’t afford to invest in great technology. That realization set Paul on a path to create DeathTech software that could help families better memorialize loved ones online.

“People actually die twice: They die once here on earth and a second time, digitally,” Paul said.

The Californian had an idea for a startup but struggled to get a foot in the door in southern California. As a non-technical founder, he knew he needed access to both mentorship and capital to build his business. Despite being based down the coast from the epicenter of tech entrepreneurship, Paul couldn’t secure a pitch to potential investors in his home state.

Frustrated but undaunted, Paul began researching startup accelerators further afield. That’s when he stumbled upon an immediate opportunity: Startup Weekend Iowa City, which was taking place a few days later.

“I literally booked my flight and jumped on a plane the next morning,” Paul said.

Iowa felt like the right place for Paul to bring his idea – his grandparents were born and memorialized here and it’s where his vision for a startup first began to take root.

Connecting with a Co-Founder

Tumbleweed founders sitting on a bench under the trees.
Tumbleweed founders L to R: Keisha Chandler, Paul H. Richardson Jr., Colleen Kinsey

Paul was excited to pitch his software solution at Startup Weekend Iowa City. As a latecomer, he was slated to present last—after Des Moines-based developer Colleen Kinsey. Collen got on stage and told the crowd about watching her grieving mother struggle to serve as executor of her grandparents’ estates. Then, she pitched a platform that could help create opportunities to celebrate their legacy digitally.

“I had to pinch myself,” Paul said. “Did I really just jump on a plane to Iowa to have the person in front of me steal my idea?”

After Paul and Colleen recovered from the shock of pitching strikingly similar ideas, they realized they might make excellent collaborators. Colleen could contribute the technological and project management skills that Paul lacked. The Iowa State University alumna had experience designing and building healthcare application software. Paul’s background in organizational development contributed to their competitive edge. They teamed up for the Startup Weekend competition—and won.

Together, they formed a team and evolved Tumbleweed with their third founder, Keisha Chandler. The platform was originally designed to help families cope after the passing of a loved one. But, with input from Des Moines tech leaders, it now goes beyond funeral planning guidance and offers proactive tools that create a one-stop-shop for legacy planning paperwork.

“It was a whirlwind,” Colleen said of their professional courtship. She was initially worried she might not have the bandwidth to pursue this idea because she was already running a different consulting business. “Having someone equally as passionate and who has the energy and skill sets that complement where I’m coming from was a beautiful match. I would never have been able to take this idea to the next level on my own.”

Meeting in the Middle

Colleen was already operating out of Gravitate Des Moines’ downtown location, a coworking space popular with innovators and entrepreneurs, and Paul began visiting often. It didn’t take long for the co-founders to realize that making Tumbleweed an Iowa-based company would create advantages. They completed extensive customer interviews and prototyping as part of Venture School at the University of Iowa’s John Pappajohn Entrepreneurial Center. Tumbleweed also received grant funding from the Iowa Economic Development Authority and was accepted into the Des Moines-based Global Insurance Accelerator.

Related: Read about how insuretech conveners launched the Global Insurance Accelerator to create a network of entrepreneurial support.

“[These opportunities] helped us evolve our thinking to see Tumbleweed as a value-add product to life insurance policies,” Paul said. “People are working so hard to build generational wealth that they can pass down. How do you make sure that that is going to the right places and the right people?”

Customers who were already making plans to protect their family’s financial futures could also be interested in a tech tool like Tumbleweed to help support other aspects of the process. Tumbleweed’s early traction within insuretech inspired Paul to relocate. Within a few months of finding Startup Weekend success, he committed to a one-way ticket to Iowa.

“I officially moved in October, and it was honestly the best decision,” Paul said. “The startup ecosystem really started to open up. For me, what has been uniquely Iowan is that people are warm, generous with their time, and willing to talk to you and make an introduction to people who can help.”

Published April 22, 2024

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