Company Overview
Paul H. Richardson, Jr. is Founder & CEO of Tumbleweed, an end-of-life planning company that offers a thoughtfully curated journey to honor and memorialize the one you have lost. For individuals engaging in proactive planning, ensure your preferences are securely documented and fulfilled seamlessly. Learn more at https://tumbleweedplan.com/.
Can you tell us a little about your background before starting your company?
Before founding Tumbleweed, I spent over two decades in healthcare, education, and innovation, including leadership roles at CVS Health, Hoag, and Banner Health. I’ve always been driven by a desire to make systems work better for people; whether that meant improving patient experiences or building more human-centered organizations. The real spark for Tumbleweed came after a six-year period where I lost six family and friends. As a caregiver and family member, I experienced firsthand how broken, confusing, and isolating the process of navigating aging, death, and legacy planning can be. I couldn’t stop thinking about how we could build something better.
How did you start your company? What were the first steps you took to get it off the ground and how did you identify the need for your product/service in the market?
Tumbleweed began as an idea during a cross-country road trip in 2022. After years in healthcare and as a caregiver, I saw the emotional and logistical weight families carry and the lack of supportive tools to help them plan ahead or manage a loved one’s passing. I started talking to other caregivers and industry professionals, mapping out the pain points and gaps. From there, I began validating the concept, prototyping early versions, and eventually brought on co-founders who shared the vision. What started as a personal reflection turned into a tech company built to support the Sandwich Generation and beyond.
What innovations or unique features set your company apart from others in the industry?
What sets Tumbleweed apart is our Agentic AI-powered platform that guides families through aging, caregiving, and legacy planning. Unlike static digital tools, we provide ongoing, adaptive support, meeting users where they are and helping them close planning gaps over time. It’s not a one-and-done checklist; it’s a journey we walk with them. We also focus on wraparound support and B2B partnerships with insurance carriers, helping institutions better engage and support their aging policyholders and their family caregivers.
What has been the most effective strategy for scaling your business?
Our most effective growth strategy has been partnering with organizations that already serve our target population as well as industry conferences. We’re focused on embedding Tumbleweed into the employee benefits ecosystem and insurance landscape; making it easy for families to access our tools without paying out of pocket. Accelerators like the Global Insurance Accelerator and NMotion, as well as partnerships like the one we recently launched with Wellabe, have helped us validate, refine, and scale.
Looking ahead, what are your goals for the future of your company?
Looking ahead, our goal is to become the go-to platform for families navigating aging and caregiving—not just by organizing paperwork, but by preserving stories, honoring wishes, and mitigating burden. We’re building a future where families feel supported during some of life’s hardest moments, and where caregivers aren’t left to figure it all out alone. Our next chapters will include expanding our partnerships, integrating more legal and financial tools via partnerships, and building community through initiatives like our upcoming podcast in September.
