Visionary Advisor

Legacy letters give families the words that outlast any estate plan. Blake Brewer, founder of the Legacy Letter Challenge, joins Alex Kirby to show how wealth advisors can make this practice standard for every HNW client without it feeling heavy or hard to start. If legacy conversations are missing from your client relationships, this is the episode that changes that.

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 software 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)

Send us feedback

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

Send us feedback

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

Intergenerational wealth is about far more than money. Legendary family wealth author James E. Hughes returns to Visionary Advisor to walk through the full capital stack: human, intellectual, social, and financial. Advisors who understand complete family wealth are the ones multigenerational families trust and keep for decades.

Wealth that isn’t lived as wellbeing is a tragedy—one advisors help write unless they change the story.

On this episode of Visionary Advisor, host Alex Kirby (founder, Total Family) is joined by James E. Hughes, who has shaped how the profession thinks about multigenerational wealth. Jay challenges advisors to look past balance sheets, exploring why “wealth” must mean family flourishing, not just the sum of assets.

Together, they tackle the problem of sterile planning versus the lived, dynamic “play” of family life. They examine why words matter, the hidden cost of secrecy around money, and how family meetings can either foster connection or leave heirs disengaged. Hughes’s framework—anchored in the Five Forms of Capital—offers a blueprint for helping families grow in ways that numbers alone can’t capture.

Advisors will come away with a practical lens for running better family meetings, engaging rising generations, and building trust that endures beyond a liquidity event or loss.

What You’ll Learn in This Episode

• Why redefining “wealth” as wellbeing transforms your client relationships
• The power of language in legacy work - especially with the rising generation
• What families lose when money is a secret
• How to use stories (even failures) to foster resilience and belonging
• Why most family plans fall short, and how to shift toward “plays”
• Steps for structuring family meetings that actually support human capital

Notable Quotes from James E. Hughes

“The word wealth…meant well-being. It has never meant anything but that.”

“Humans don't live in plans, they live in plays. The problem of plans is they're sterile.”

“The purpose of a meeting, any meeting of a family, is to grow its spiritual, social, intellectual, and human self…”

Resources

• Complete Family Wealth, by James E. Hughes
• Where Are All the Customers' Yachts? 
• Total Family 

Send us feedback

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

Send us feedback

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

When a family loses someone, the grief tax is real, and most wealth advisors are not equipped to help carry it. Ron Gura, CEO of Empathy, joins Alex Kirby to discuss what HNW clients actually need from their advisors during loss and how showing up in those moments builds the kind of trust that survives generations. This conversation will change how you think about client care and legacy planning.

Death is not an if — it’s a when. And yet most advisors are never taught how to show up when a client experiences loss.

In this episode of Visionary Advisor, Alex Kirby, founder of Total Family, sits down with Ron Gura, co-founder of Empathy, to explore what happens when grief, finance, and responsibility collide. Ron shares insights from Empathy’s research report, The Grief Tax, which examines the emotional, administrative, and financial burden families face after the death of a loved one — and why these challenges are often inseparable.

The conversation explores why advisors are uniquely positioned to support families during loss, how well-meaning sympathy can fall short, and what it really means to move from condolences to meaningful action. Alex and Ron also unpack the realities facing the “sandwich generation,” the shortcomings of bereavement leave in the U.S., and why proactive legacy planning — letters, values, conversations, and systems — can ease future hardship even when grief can’t be avoided.

This episode challenges advisors to rethink how they show up before and after loss — and how doing so can strengthen trust, continuity, and family relationships across generations.

What You’ll Learn in This Episode

• Why grief and financial logistics cannot be separated during moments of loss
• How the advisor’s role shifts from transaction to relationship after a death
• Why heirs may disengage when advisors only show up after a loss occurs
• What the “sandwich generation” is facing as they care for children and aging parents simultaneously
• Why legacy planning must include emotional preparation, not just legal documents
• How proactive systems and conversations can reduce overwhelm when the inevitable happens

Notable Quotes from Ron Gura

“Grief is made harder by logistics, and logistics are made harder by grief.”

“You have to shift from sympathy and condolences to empathy and action.”

“This isn’t a one-and-done moment. This is human, messy, and complicated.”

“If you want your kids to take care of each other and the surviving spouse when you’re gone, you probably need a week, a month, and a bottle of wine to really talk about it.”

“Don’t ask me if I need anything. Tell me what you’re doing to help — and do it.”

Resources

• The Grief Tax: Empathy’s Annual Research Report
 https://www.empathy.com/thegrieftax

 • Empathy
 https://www.empathy.com/

Send us feedback

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

Harris Poll data shows what HNW families expect from the great wealth transfer, and most advisors are missing the mark on what those families care about most. The research makes clear that values, relationships, and legacy conversations rank higher in client priorities than the financial mechanics of wealth transfer. Advisors who understand this shift are far better positioned to retain rising gen clients.

Most wealth advisors think they understand how different generations view legacy and the great wealth transfer. New research from The Harris Poll shows how wrong some of those assumptions can be.

In this episode of Visionary Advisor, Alex Kirby, founder of Total Family, sits down with Jennifer Musil, Global President of Custom Research, and Melissa Schweizer, SVP of Financial and Professional Services at The Harris Poll, to unpack findings from America’s Great Wealth Transfer report and a custom legacy study conducted through the lens of the five forms of family capital.

The conversation reveals a powerful shift: while money still matters, the rising generation defines legacy in far more human terms. Well-being, personal development, values alignment, and emotional trust now sit at the center of how heirs think about wealth — and whether they stay with their parents’ advisors or leave.

This episode challenges advisors to rethink how they approach legacy, communication, and relationship-building ahead of the largest intergenerational wealth transfer in history.

What You’ll Learn in This Episode

• Why legacy goes beyond financial, with human capital ranking highest in perceived importance
• How younger generations define the purpose of wealth differently than prior generations
• Why values misalignment and weak personal relationships drive advisor switching risk
• What heirs actually want from advisors during and after the wealth transfer
• How communication and collaboration shape trust before money ever changes hands

Notable Quotes

“Legacy goes beyond financial. Human capital rose to the top with 83% saying well-being and development of each family member is a significant contributor to their legacy.”

“This is a story about humans wanting to work with other humans and have a relationship.”

“Even when people have to pick just one, three quarters say something else other than money matters most.”

“Technology can explain the mechanics, but it can’t carry the emotional weight of inheritance.”

Resources

America’s Great Wealth Transfer Report — The Harris Poll
https://theharrispoll.com/insights-news/reports/americas-great-wealth-transfer/

Full Report PDF https://drive.google.com/file/d/1VV152oN7hStk0YItdZ6f6QCjAJdKlM72/view?usp=sharing 

Custom Legacy Study: Perceptions of Legacy Go Beyond Financial — The Harris Poll

https://drive.google.com/file/d/1TGhbwsUg-eiHfeU574BeO7f8uCqsKocg/view?usp=sharing

Send us feedback

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

HNW clients talk about their wealth advisors to each other, and most advisors have no idea what those conversations sound like. Matt Shechtman of Long Angle, a private community for high net worth investors, joins Alex Kirby to share candid data on how these clients evaluate and compare advisors in private. If you want to understand what drives HNW client loyalty and referrals, this episode gives you that honest view.

Most firms say they serve high net worth clients. Very few actually understand them. As more firms push upmarket toward $50M-plus relationships, a real opportunity is opening for advisors who take the high net worth segment seriously and listen closely to what these clients actually value.

In this episode of Visionary Advisor, Alex Kirby talks with Matt Shechtman, CEO of Long Angle, one of the most trusted communities and investment platforms for high net worth families. Long Angle recently released their 2025 High Net Worth Professional Services Report, and the results sparked a wave of conversation for a simple reason: the findings are both measurable and uncomfortable.

From why personal trainers and pool service can outscore wealth management in satisfaction, to why only a minority of respondents use a wealth manager at all, this conversation explores the shifting expectations of younger HNW families and what advisors can do to close the value gap with clearer pricing, better integration, and more human, relationship-driven service.

What You’ll Learn in This Episode

• What the report reveals about satisfaction across professional services, and why the “pool guy vs. wealth manager” takeaway resonated
 • Why younger HNW clients increasingly optimize for health, family, and time, not just financial returns
• What the $10K-per-year fee conversation is really about, and why transparency and itemization build trust
• Why CPA dissatisfaction is often about proactivity and strategic value, not just responsiveness
• Why many HNW clients self-manage investments, and what advisors must offer beyond investment management to stay relevant

Notable Quotes from Matt Shechtman

“Value is probably the number one takeaway from all of this.”

“When you have something that you can actually see progress on, that really helps in terms of satisfaction.”

“Wealth can be isolating.”

“People are desperate for unbiased advice. There’s a disconnect and a lack of trust.”

Resources

• 2025 High Net Worth Professional Services Report (https://www.longangle.com/research/high-net-worth-professional-services)
 • Long Angle (https://www.longangle.com/)
 • Matt Shechtman (https://www.linkedin.com/in/msheck/)

Send us feedback

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

Legacy is the defining work of a great wealth advisor. Robert Balentine, CEO of Balentine, has spent decades building a firm rooted in values-based advising and multigenerational planning. He joins Alex Kirby to discuss what separates advisors who become trusted family institutions from those who get replaced when the next generation inherits.

Some names in wealth management are respected. A few are legendary. Robert Balentine is one of them. If you’ve spent time in the ultra-high-net-worth world, you know the Balentine name and the influence the firm has had on how families think about wealth, values, and legacy. 

In this episode of Visionary Advisor, Alex Kirby sits down with Robert to explore the lessons inside First Generation Wealth and Balentine’s Family & Legacy Guide — including why legacy is a continuum, why empathy is essential, and why rising-generation perspective matters more than ever. 

With more than 35 years of experience, Robert shares how families can communicate better, avoid “weaponizing money,” and build alignment across the household. He also explains why advisors must lead by example and why failing to engage both spouses puts the entire relationship at risk. 

What You’ll Learn in This Episode

• Why legacy is a continuum, modeled through small, intentional actions over time
• Why wealth does not equal legacy — and what actually endures across generations
• Why early, ongoing communication far outperforms end-of-life planning alone
• How empathy, vulnerability, and perspective shape healthier family conversations
• Why alignment between spouses is the cornerstone of lasting multigenerational success

Notable Quotes from Robert Balentine

“Most ultra-high-net-worth investors are worried about things much deeper than money. They’re worried about their legacy.”

“Our happiest clients think about legacy early and communicate it often.”

“Family advising is sacred work.”

“You keep your children closer by giving them space.”

Resources

• Book: First Generation Wealth (https://www.firstgenerationwealth.com)
• Guide: Family & Legacy Guide (https://www.balentine.com/legacy)
• Firm: Balentine (https://www.balentine.com/)
• LinkedIn: Robert Balentine (https://www.linkedin.com/in/robert-balentine-8695521a/)

Send us feedback

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

HNW clients know they need an estate plan, but most still delay taking action. David York of Entrusted joins Alex Kirby to explain why the barrier is almost never information, it is inspiration. He shares a practical framework for advisors to open legacy conversations in a way that motivates clients to follow through on the planning that protects their family wealth.

What if the problem with estate planning isn’t that clients are uninformed, but that they’re uninspired?

In this episode of Visionary Advisor, David York, attorney, CPA, and Managing Partner at York Howell, joins Alex Kirby to reframe how advisors think about legacy, family leadership, and the true purpose of wealth.

Drawing from his book Entrusted: Building a Legacy That Lasts, David explains why traditional estate planning often fails—not because of poor execution, but because it focuses on assets and taxes rather than values and purpose. He shares how advisors can help clients move from fear-based planning to inspired conversations about meaning, responsibility, and family connection.

From his “flint and kindling” analogy to the lessons of Mayer Rothschild, David shows how families can pass on wisdom, not just wealth—and how advisors can guide that evolution.

Whether you serve $10M families or multi-generational enterprises, this episode challenges you to elevate your role from technician to teacher, from planner to purpose-builder.

What You’ll Learn in This Episode:

• Why so many clients delay estate planning—not from ignorance, but from lack of inspiration
 • How to move from documents and distributions to dialogue and discovery
 • The “flint and kindling” approach to transferring wisdom and opportunity, not just money
 • How to structure plans that balance rights and responsibilities across generations
 • Three powerful questions every family should answer before they plan
 • Why true legacy requires aligning assets with values—not just minimizing taxes

Notable Quotes from David York:

“Clients aren’t uninformed. They’re uninspired.”
 “Transferring financial resources is transferring the result of your work—the fire is the real asset.”
 “You can’t transfer the cost that comes with wealth. And when you can’t transfer cost, you can’t transfer value.”
 “The best families prepare the next generation for wealth. They don’t just prepare wealth for the next generation.”
 “Does your plan reflect who you are—or just how much tax you saved?”

Resources:

Book: Entrusted: Building a Legacy That Lasts

Website: www.davidryork.com

LinkedIn: David R. York

York Howell: https://www.yorkhowell.com/

Send us feedback

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

Family mission statements are going mainstream, and the Wall Street Journal is covering it. Whitney Webb of Cresset joins Alex Kirby to explain why this matters for wealth advisors working with multigenerational families and how documented family values make both family governance more durable and advisors more indispensable to the process.

Since the Wall Street Journal is writing about Family Mission Statements, it’s only a matter of time before your clients start asking about them. For advisors, that means now is the time to get out ahead of the trend—and find your footing on what these conversations are really about.

In this episode, Whitney Webb, Managing Director at Cresset and a leading expert in legacy planning, joins Alex Kirby to unpack what’s driving this growing interest in purpose and alignment among ultra-high-net-worth families. 

Drawing on more than a decade of experience helping families prepare for the responsibilities and challenges of wealth transfer, Whitney shares why lasting harmony doesn’t begin with a mission statement—it begins with honest, intentional conversations about what matters most, where families thrive, where they struggle, and how every voice can be heard.

Whether you advise $30M or $3B families, this episode helps you stay ahead of the curve as wealth planning evolves from managing money to fostering meaning.

What You’ll Learn in This Episode:

 • Why values—not mission statements—are the true foundation of family legacy
 • How advisors can help families slow down, listen deeply, and include every generation
 • The four priorities UHNW families must force-rank to avoid conflict and sustain harmony
 • Why “the process is the point” in family planning and communication
 • How authenticity, vulnerability, and curiosity build trust across generations
 • Why today’s advisors are evolving into educators, facilitators, and mentors

Notable Quotes from Whitney Webb: 

“As wealth grows so rapidly, families are asking deeper questions: What does it all mean? How much is enough? What truly brings fulfillment?”

“You can write a charter or mission statement in a day—but if people don’t see their voices in it, it won’t last.”

“Authenticity and vulnerability are in. Overconfidence is out.”

Article Referenced in This Episode:

Wall Street Journal: Wealthy Families Are Writing Mission Statements to Avoid Fights, Lost Fortunes
https://www.wsj.com/finance/investing/wealthy-family-mission-statements-e08faabd?st=vG2NiP&reflink=desktopwebshare_permalink

Connect with Whitney Webb:

Email: [email protected]

Profile: https://cressetcapital.com/about/team/whitney-webb/

Send us feedback

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

How do HNW families decide between a multifamily office and a wealth advisor? Rachel Hyman of Family Wealth Alliance brings clear, research-backed perspective on where the line is, what services families actually value, and how independent wealth advisors can compete for and retain the most complex multigenerational client relationships.

The term “multifamily office” gets used by nearly every wealth firm today, but few can define it clearly—and even fewer deliver what ultra-high-net-worth families truly need.

In this episode, Rachel Hyman, President of Family Wealth Alliance, joins Alex Kirby to bring structure and insight to an increasingly crowded and confusing space. Drawing on FWA’s Voice of the Client Survey, developed with Bain & Company, Rachel shares how elite firms deliver not just functional value, but emotional connection, reduced anxiety, and generational stickiness.

You’ll learn how the best MFOs think about complexity, family dynamics, client expectations, and how to benchmark your own firm using both the Elements of Value and FWA’s 10 multifamily office service areas. Whether you serve $30M or $300M families, this conversation will help you clarify your positioning—and elevate your client experience.

This is a must-listen for advisors looking to deepen relationships, differentiate in the UHNW space, and build a multigenerational practice rooted in purpose and trust.

What You’ll Learn in This Episode:

• The four-part framework that defines a true multifamily office
 • What over 3,000 UHNW clients say they really value in an advisor
 • Why emotional connection and anxiety reduction matter more than performance
 • How “heirloom,” “hope,” and “self-transcendence” show up in wealth advising
 • The 10 service areas that define MFO integration and complexity
 • Why fees ranked near the bottom in importance for ultra-wealthy clients
 • How firms are using this data to improve retention, loyalty, and relevance

 Notable Quotes from Rachel Hyman: 

 “The best firms today are not just managing money. They’re managing complexity.”

 “Reducing client anxiety is the single biggest differentiator in this space.”

 “Emotional value is where you create stickiness. That’s how you build a 50-year relationship.” 

Explore More from Family Wealth Alliance:

 Voice of the Client Survey Toolkit → https://www.familywealthalliance.com/cpages/clientsurveytoolkit

 MFO Standards PDF → https://mcusercontent.com/c242860553fd2c0fef2abbca3/files/357fb0c3-1295-9fc2-4aae-1896ab1f6516/MFO_Standards_Dec_2024_1.pdf

Send us feedback

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

Capgemini's global wealth data shows the great wealth transfer is accelerating faster than most advisors realize. P.V. Narayan joins Alex Kirby to share what the numbers reveal about rising gen expectations, advisor retention risk, and the window of opportunity that exists right now for advisors who lead with family wealth strategy rather than portfolio management alone.

Over the next two decades, $83.5 trillion in wealth will shift to a new generation—yet 81% of next-gen high-net-worth individuals plan to switch advisors shortly after inheriting. That should be a wake-up call.

In this episode, P.V. Narayan, Head of Banking for the Americas at Capgemini, joins Alex Kirby to discuss the firm’s latest World Wealth Report and what it means for the future of advisory relationships.

P.V. outlines why this moment is different from past warnings about wealth transfer—and how firms can position themselves to retain assets, remain relevant, and recruit top talent. Together, they explore the mindsets of rising-gen investors, the digital fluency gap in advisory firms, and the skillset shift advisors must make to thrive in an AI-first era.

This conversation is a must-listen for advisors who want to stay ahead of the curve, meet the expectations of younger clients, and build a multigenerational practice that lasts.

What You’ll Learn in This Episode:

• Why the $83.5 trillion wealth transfer is finally triggering real change
• What next-gen clients want—and why they’re ready to walk
• The hidden cost of failing to build relationships with heirs and spouses
• Why digital fluency is now a baseline expectation
• How to compete nationally and internationally in a post-geographic advisory world
• What firms must do to attract and retain rising advisor talent
• Why the human element still matters more than ever

Notable Quotes from P.V. Narayan:

“It’s not a matter of if the transfer happens. It’s when. The firms who prepare now will be the ones who thrive.”

“This generation of clients is AI-first. They expect tools, access, and insights—not just advice.”

“Advisors don’t just need new products. They need a new posture—one that says: I understand who you are and what you want.”

Explore the Capgemini 2025 World Wealth Report: https://www.capgemini.com/wp-content/uploads/2025/06/WWR_2025.pdf

More from Capgemini: https://www.capgemini.com/us-en/insights/

Send us feedback

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