A single tumbleweed roamed a stretch of highway between California and Arizona, forcing Paul Richardson to stop his car. As he gazed at the barren landscape, one of the many business ideas in his head began to crystallize. Were the stars aligned? Was this a sign sent from the grave?

“I ideate when I’m on the road,” said Richardson, CEO of Tumbleweed, a digitally accessible legacy planning platform. 

That’s the origin behind Richardson’s company name. Tumbleweed the venture has been through a few twists and pivots as it prepares to launch a second version, something made possible after winning a $9,000 second prize at the University of Iowa’s Venture School Launch Day on June 13 in Cedar Rapids, Iowa. 

“That will allow us to continue to showcase all that we are doing: Pitching, meeting investors, meeting partners,” Richardson said. “That takes money. This allows us to start building Product 2.0.”

Tumbleweed has been named University of Iowa John Pappajohn Entrepreneurial Center (Iowa JPEC) Venture School Business of the Year. Richardson will be recognized at the Innovation and Entrepreneurship Honors event Oct. 11.

In 2022, while living in California and working for a small consulting firm, Richardson embarked on a four-month, 22-state trek that included Iowa, home state to two of his grandparents. 

“I realized early on I was holding onto some grief with my grandparents who had passed,” Richardson said. 

This was during a difficult period in his life when he lost six family members over six years. Throughout this time, Richardson witnessed the full spectrum of end-of-life experiences—the good, the bad, and the ugly. It's not uncommon for such times to become contentious and challenging.

“I saw an opportunity and wondered if there was a better process out there,” Richardson said. 

Soon after Richardson came up with the idea for Tumbleweed, he hopped on a plane and flew to the 54-hour Techstars Weekend in Iowa City in June of 2023. He had one day to decide to fly from California to Iowa and that decision paid off. Once he was in Iowa City, he met co-founder and CPO Colleen Kinsey. Kinsey joined Richardson and Keisha Chandler, co-founder and COO, rounding out the co-founding team. Richardson moved to Des Moines, and that fall, he and Kinsey entered Tumbleweed in the Des Moines cohort of Venture School, a seven-week program sponsored by the University of Iowa John Pappajohn Entrepreneurial Center (Iowa JPEC). They placed third in the final pitch competition, won $500, and gained many valuable ideas.

He pitched his memorialization idea to those in the funeral industry, but they saw Tumbleweed more as a competitor than an ally. After talking with customers, it was time to morph significantly. The new target audience became people interested in doing digitized preplanning for aging family members. 

“Let’s become an employee benefit built into an insurance product,” Richardson said. “With your life insurance policy, you get access to Tumbleweed automatically, it is embedded in there.”

The plan would include quarterly check-ins with an annual review every tax season. 

“Our mentors challenged us to think about new pathways and who to talk to,” Richardson said. “They made a lot of introductions and interactions and helped us with our customer discovery and the refinement of our go-to-market strategy. I always knew there was an insurance angle, but I didn’t know how to figure out the pathway to get there. Through Venture School, we looked at the market and the expertise of our co-founding team.”

Tumbleweed has also completed the Global Insurance Accelerator in Des Moines and started the Fall 2024 NMotion Accelerator powered by gener8tor based in Nebraska. As Tumbleweed looks to the future, its progress has laid a strong foundation for what is to come, thanks in part to invaluable assistance from Iowa JPEC.

“We have a minimum viable product that has been completed, we have gone through user testing and identified what is working well and what are the additional features we need to prioritize,” Richardson said. “We are building that roadmap and fundraising is on the horizon.”

To learn more about and register for Venture School this fall, click HERE.

To learn more about out 2024 Innovation and Entrepreneurship Honors recipients, click HERE.