Paul Richardson, Founder of Tumbleweed, shares how his own family experiences—and a 20-year career in healthcare—sparked the idea for a digital platform that helps families plan for aging and end-of-life. After losing six loved ones in six years and seeing first-hand how disorganized the process can be, Paul built Tumbleweed to simplify everything from storing key documents to closing gaps in planning and even supporting families after a death.
We explore:
✅ How a four-month cross-country road trip helped Paul process grief and inspired the earliest version of Tumbleweed
✅ Why early customer interviews shifted the product from post-death support to proactive pre-planning
✅ How Tumbleweed partners with insurance carriers to help policyholders get organized and protect their families
✅ Lessons from building an MVP in just a few months and iterating quickly
✅ Why a founder-led brand and authentic storytelling are critical in a space as personal as aging and end-of-life planning
Paul shares candid insights on navigating the “sandwich generation,” building a startup in a highly emotional category, and why empathy and lived experience can be a powerful competitive advantage.
👉 Learn more about Tumbleweed: https://tumbleweedplan.com/
👉 Connect with Paul on LinkedIn: https://www.linkedin.com/in/paulhrichardsonjr/
👉 Listen to the Sandwhiched podcast: https://open.spotify.com/show/19UOaQ0j9jITHkCvrfKlHR
Connect with me (Dan Ritzke):
I’m a Fractional CMO who helps FamTech companies position their brand, sharpen their messaging, create marketing strategies that drive growth, and oversee execution to make sure those plans turn into results.
👉 Visit my website: https://danritzke.com/
👉 Connect with me on LinkedIn: https://linkedin.com/in/ritzke/
Apply to be on the podcast or nominate a founder:
👉 Founders in Full: https://danritzke.com/podcast/
