Reimagining Legacy: How AI and Storytelling Are Transforming Estate Planning

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CMOs Without Borders

Joel Crampton

6 episodes

10 hours ago

Welcome to CMOs Without Borders — the podcast where two seasoned marketing leaders with decades of experience from opposite sides of the border cut through the noise and get real about what actually drives growth in financial services. Hosted by fractional CMOs Joel Crampton, founder of CMO/Alpha (U.S.), and Mandy MacPhee, founder of illumination (Canada), this show explores the strategic marketing moves that help RIAs, fintechs, credit unions, and financial brands thrive — regardless of size, structure, or postal code. We bring different lenses to the mic: U.S. vs. Canada, Fintech vs. Institutional, Independent firms vs. Enterprise marketing But we’re united by one mission: helping you build a smarter, more strategic marketing function that actually drives results — not just more activity. Each episode delivers candid conversations, real-world examples, and field-tested insights to help you: - Align your marketing with business goals - Outperform the competition without wasting time or budget - Gain the clarity and confidence to lead — or delegate — marketing that works If you’re a financial advisor, fintech founder, credit union exec, or marketing leader in the financial space, this is your “no-fluff, behind-the-scenes look” at what works — and what doesn’t.

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Reimagining Legacy: How AI and Storytelling Are Transforming Estate Planning

CMOs Without Borders

57 minutes 28 seconds

3 weeks ago

Reimagining Legacy: How AI and Storytelling Are Transforming Estate Planning

EPISODE OVERVIEW
In this episode, hosts Joel Crampton and Mandy MacPhee sit down with Randy Frisch, founder of Trusty, an AI-powered estate planning platform redefining how families manage, document, and pass down their legacies. With $84 trillion set to change hands in the coming decades, Randy shares how technology, emotion, and storytelling can transform estate planning from a cold, legal process into a deeply personal, human experience.

This conversation explores how advisors and families alike can move beyond wills and trusts to create meaningful legacy plans — ones that connect generations, reduce conflict, and capture the stories behind the assets.

ABOUT OUR GUEST

Randy Frisch is the founder and CEO of Trusty, an AI-driven estate planning platform helping families document and communicate their wishes with clarity and connection. Before Trusty, Randy co-founded Uberflip, one of Canada’s most successful SaaS companies, which scaled globally and was later acquired.

KEY TOPICS COVERED

● Why traditional estate planning is broken and how Trusty is making it more human.

● The “letter of wishes” revolution: How families can leave behind video messages and stories that give deeper meaning to their gifts.

● AI’s role in legacy planning: Real-world ways Trusty uses “quiet AI” to simplify, summarize, and guide complex estate decisions without overwhelming users.
● Why storytelling matters: How focusing on narratives — not just features — builds trust and emotional resonance.

● Advisor opportunities: How financial advisors, estate attorneys, and planners can use legacy tech to differentiate, retain heirs, and deepen client relationships.

● Privacy & legal clarity: What’s binding, what’s not, and how to keep sensitive information secure while still making it accessible.

NOTABLE INSIGHTS

$84 trillion is projected to transfer between generations — but 80% of heirs change advisors when they inherit.
Trusty’s mobile-first platform lets families easily photograph, catalog, and assign meaningful items — from heirlooms to handwritten letters — while capturing stories and intentions.
“The stories are often more valuable than the stuff.” Video messages and backstories give assets emotional weight and reduce family conflict.
Privacy is foundational: users control access, data is encrypted at rest, and even Trusty’s team can’t view client information.

WHO SHOULD LISTEN

Financial advisors, RIAs, and wealth managers looking to differentiate their services and retain next-gen clients Estate attorneys and planners interested in modernizing legacy planning Families navigating estate planning who want to go beyond the will and leave meaningful stories behind.

RESOURCES & LINKS

Explore Trusty: https://mytrusty.ai

Connect with hosts:

Joel Crampton — Fractional CMO for RIAs and wealth managers

LinkedIn: https://www.linkedin.com/in/joelcrampton/

CMO Alpha: https://cmoalpha.com

Mandy MacPhee — Fractional CMO for founder-led companies

LinkedIn: https://www.linkedin.com/in/mandymacphee/

Illumination CMO: https://www.illuminationcmo.com/