Visionary Advisor
Welcome to Visionary Advisor, the podcast for forward-thinking wealth advisors who recognize that wealth management is evolving rapidly. Join us as we invite some of the most influential minds in the industry to share the ideas they believe HNW & UHNW advisors should be exploring and putting into practice.
I'm your host, Alex Kirby, founder of Total Family, a software company doing legacy better for wealth advisors and their clients.
Welcome to Visionary Advisor, more at totalfamily.io
Visionary Advisor
Why Wealth Advisors Should Introduce Legacy Letters to Every Client with Blake Brewer
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Death can come shockingly fast — and with it, a flood of things left unsaid. All the planning in the world means little if families never hear the words that matter most.
In this episode of Visionary Advisor, host Alex Kirby (founder of Total Family) welcomes Blake Brewer, founder of the Legacy Letter Challenge, an organization striving to help 1 million people write at least one Legacy Letter. Blake’s story began with a life-changing letter from his father after a sudden loss at age 19. Today, he helps families and advisors shift from intention to action, sharing what makes a letter truly meaningful and how to move past the common barriers that keep most from ever writing one.
Drawing from personal experience and decades of coaching, Blake breaks down the emotional and practical sides of legacy work: the value of apology and vulnerability, why timing matters less than getting started, and how simple frameworks can help families connect and preserve wisdom across generations. At Total Family, we see Legacy Letters as essential to legacy—captured, stored, and shared in our FamilyOS so they remain accessible and meaningful for years to come.
This episode offers advisors concrete strategies to move legacy planning beyond documents, building deeper trust and lasting impact.
What You’ll Learn
- Why most people never write a legacy letter, and what moves them to act
- How apology and vulnerability can reshape family relationships
- A step-by-step framework for guiding clients through their first letter
- Why starting matters more than timing or format
- How letters build trust and retention across generations after a loss
- Why advisors are best placed to turn legacy into action
Notable Quotes from Blake Brewer
“I can’t imagine my life without this letter. In the coming days and weeks and months, I never experienced more pain and grief in my life. And my life could have gone a lot of different ways... It was the exact opposite.”
“I believe everyone has a legacy letter in their heart, but getting it from your heart to your mind and then to a piece of paper — easier said than done.”
“The stories didn’t match up. And so this legacy letter is about getting the story right, like leaving nothing out. No, this is how I feel about you.”
Resources
• Legacy Letter Challenge
(https://www.legacyletter.com/)
• Total Family
(https://totalfamily.io)
Stay Connected with Visionary Advisor
We believe wealth is well-being. Subscribe to the Visionary Advisor Newsletter for practical tools and ideas to serve families across generations.
Explore more at totalfa
Stay Connected with Visionary Advisor
We believe wealth is well-being. Subscribe to the Visionary Advisor Newsletter for practical tools and ideas to serve families across generations.
Explore more at totalfamily.io | Follow us on LinkedIn | Watch episode clips on YouTube
