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Scout InsurTech Interview with Tumbleweed

Writer's picture: Andrew DanielsAndrew Daniels

Tumbleweed manages the complexities of caregiving by organizing critical documents and streamlining end-of-life and legacy planning. They seek to reduce stress and ensure families' wishes are respected. Andrew Daniels sat with Founder and CEO, Paul Richardson, to learn more about how Tumbleweed is transforming the industry.





Who are your clients?


Our target customers are insurance companies and employers. We’re a B2B organization with a primary focus on the sandwich generation—adults aged 35 to 55 who often juggle responsibilities of caring for aging relatives while supporting their own families. These individuals may provide financial support, assist with daily tasks or manage healthcare and finances for aging family members, friends and often neighbors.


What does your product do?


Our platform provides comprehensive legacy-planning tools. It helps users organize essential documents like wills, trusts, powers of attorney and insurance policies in a secure digital vault. It also empowers families to capture life stories and wishes, making the process more personal. Our goal is to reduce the burden on families, giving them clarity and peace of mind during difficult times.


How much capital have you raised?


We’ve raised over $250,000 so far, enabling us to develop and refine our platform and establish strategic partnerships.


Was the company born from within or outside the industry?


The company was born outside the industry, driven by personal experience. After losing six family and friends in less than six years, the gaps in navigating aging and end-of-life processes became painfully evident to Paul. This led to extensive research and ideation during a cross-country road trip, culminating in the creation of Tumbleweed. While our roots are personal, our solution is designed to address systemic gaps in the industry with a scalable, technology-driven approach.


What growth metrics have you accomplished over the last 12 months?


  • We achieved $68,000 in revenue for 2024.

  • Secured our first paying employer partner to offer the platform as an employee benefit.

  • Secured first insurance carrier partnership, launching this January 2025

  • Named Iowa Venture Startup of the Year for 2024

  • Gained recognition as a finalist for Startup Technology Company of the Year at the 2024 Prometheus Awards.


Within your domain, what is the current challenge the industry is facing?


One major challenge is the widespread avoidance of planning for aging and death—78 percent of Americans have not completed essential documents like wills or advance directives. For the insurance industry, customer-driven engagement is a growing expectation. Historically, there has been minimal interaction beyond policy sales, but modern customers demand meaningful, ongoing touchpoints.


How does Tumbleweed take a unique approach to providing value?


We’re unique in our holistic, inclusive approach. Unlike competitors focused on high-net-worth families, Tumbleweed serves individuals from all walks of life, emphasizing accessibility and equity. By addressing underserved demographics and incorporating seamless integrations for wills, advance directives and Powers of Attorney, we’ve created a platform that supports users from pre-planning to post-loss navigation. Our mission is to transform end-of-life planning into an empowering, approachable process, combining human touch with technology.


What inspired the team to start this company?


Tumbleweed’s story begins with a moment of reflection during a cross-country roadtrip. This sparked an idea: to create a solution for families overwhelmed by end-of-life responsibilities. Paul’s experience navigating his grandparents’ aging and passing revealed the lack of comprehensive support. Similarly, COO Keisha Chandler’s focus on representation and inclusivity in estate planning and CPO Colleen Kinsey’s expertise in digital solutions for legacy planning were inspired by their personal experiences. Together, the team shares a unified vision to transform a traditionally overwhelming process into something meaningful.


Can you share any goals for the next 12 months for the company?


  • Launched Product 2.0 in October 2024 after additional user testing.

  • Successfully piloted the platform with our first insurance carrier partner and onboard three additional partners by mid-2025.

  • Expand our team, onboarding roles to support product development, marketing and sales.

  • Build thought leadership through social media, creating resources like conversation guides and micro-videos to facilitate discussions about aging and death.

  • Enhance user resources with diverse learning modalities to make challenging conversations and decisions more accessible.




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