Visionary Advisor

Purpose is no longer a niche topic — it’s the question families expect their advisors to help answer. If you’re not guiding that conversation, someone else will.

In this episode of Visionary Advisor, Alex Kirby (founder of Total Family) , sits down with Jill Shipley, Managing Director and Head of Governance & Education at AlTi Global. Jill brings nearly 25 years of experience on the front lines of multi-generational family work. Together, Alex and Jill review the findings of AlTi’s Wealth with Intention report, exploring why “purpose” has become essential in wealth management—and what’s driving the shift from conversation to action.

They discuss why financial performance alone is no longer enough to differentiate advice, the changing expectations of rising generations, and the risks of skipping the deeper questions about legacy and intent. The conversation examines how advisors can structure their process around what families actually want their wealth to accomplish, as well as strategies to foster collaboration and autonomy in the next generation. Jill and Alex look honestly at where the industry still gets governance wrong, when outside facilitation is needed, and why a purpose statement is just the start—not the end—of impactful planning.

For any advisor aiming to retain clients across transitions, create real family impact, and stay relevant as technology commoditizes financial planning, this is essential listening.

What You’ll Learn in This Episode

• 00:00 Why starting with “What do you want the money to do?” changes everything
• 00:03:08 The hard shift from investments as the core value to purpose as the differentiator
• 00:06:05 What’s behind the sharp rise in families defining a purpose of wealth—and why “preserving and building” isn’t enough
• 00:09:38 How generational differences (Millennials, Gen Z) are redefining what matters in legacy planning
• 00:11:26 The right sequence: Defining purpose before writing the investment policy statement
• 00:16:05 The hidden risks when purpose work is skipped—and how fear (and failure) motivate change
• 00:22:04 Balancing individual autonomy with family togetherness in governance structures
• 00:28:43 What works—and what backfires—when engaging the rising generation
• 00:36:36 Why the magic of purpose is in the conversations, not the statement on the wall
• 00:40:08 How outside facilitation creates safer, stronger, and more actionable family meetings

Notable Quotes from Jill Shipley

“What do you want the money to do for you, for your family, for future generations, for the community and the world? Let's start there.”

“The process of creating a purpose statement is magic, but how you live it, what you do to implement it—that's really what matters.”

“If you don't have this conversation and you don't get really clear and grounded in why, unfortunately, the outcome that I tend to see... destroys relationships, it creates resentment. The next generation is not prepared.”

“I think we have to start with individual wellness before we go to force togetherness.”

“Somebody that's mired in your financials might not be the best person to help you think about your dreams.”

Resources

• Total Family (https://www.totalfamily.io/)
• Wealth with Intention: Purpose at the Center of the Modern Family Office — AlTi Global (https://www.alti-global.com/_files/ugd/9d4466_6e5e1f88bc084f7bb7221a6fb7c2f59d.pdf)
• AlTi Global (https://www.alti-global.com/)

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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

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We believe wealth is well-being. Subscribe to the Visionary Advisor Newsletter for practical tools and ideas to serve families across generations.
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Who goes first when it’s time for “the conversation”? 

Inheritance, legacy, and values transfer are on everyone’s minds, but families keep waiting for the perfect moment, and it rarely comes.

In this episode of Visionary Advisor, Alex Kirby (founder of Total Family) chats with Emily Harper and Jessica Gibbs of Monument Wealth. Together, they tackle the universal anxiety around initiating wealth conversations, the myth of the “right time", and what really holds families (and advisors) back.

The podcast explores why these conversations are so emotionally loaded, what parents and rising gen actually want from each other, and how advisors can move beyond legal documents to foster trust and clarity. They dig into sibling dynamics, the realities of wealth and "spoiling", and the practical ways to lead with curiosity instead of statements. Emily and Jessica share their perspectives from the front lines, including why doing nothing is usually the worst plan and why the advisor’s role is so much bigger than portfolio management.

If you advise families facing a generational transition or are one yourself, this episode will change how you think about timing, trust, and what really builds legacy.

What You’ll Hear in This Episode

• 00:00 Why families hesitate to start money conversations, and the stakes of waiting too long
• 02:28 How visibility of wealth shapes unspoken questions and assumptions in rising gen
• 04:41 The difference between transferring dollars and transferring values
• 06:03 The internal roadblocks parents face: loss of control, mortality, and fear of spoiling
• 08:16 Why intentions and expectations matter more than legal documents for heirs
• 14:44 How money talk overlaps with other “taboo” family topics — and what makes it uniquely hard
• 17:49 Why “doing nothing” rarely helps, and how storytelling can lower the stakes
• 22:31 Practical strategies for advisors when clients resist: making the case, starting small
• 23:41 Navigating sibling dynamics and maintaining family continuity across branches
• 30:50 Why advisor-facilitated continuity matters for multi-generational legacy
• 34:58 Tips for advisors: Start small, leverage values, and use existing tools to deepen family conversations
• 39:02 How families can lead with strengths—not just fix deficiencies—when starting communication journeys

Notable Quotes

“Because this is such an emotional conversation and people put so much weight behind it, they delay having conversations because they want the perfect moment... Those moments might not present themselves.” Emily Harper

“So even if it’s not perfect, you should absolutely be having conversations. They don’t have to be a big major conversation. It can be as simple as you’re all on a beach trip together and you ask mom and dad, hey, I remember X, Y, and Z about growing up when you were running your business.” Emily Harper

“There’s a lot of really important things that need to be talked about along the way that people just don’t know how to have that conversation sometimes. They don’t know how to start.” Emily Harper

“A family is not just just your nuclear family that you started with. There’s a lot of people who start to come on board along the way who have different communication styles, different experiences with money.” Emily Harper

“I think the rising generation is really craving to understand what are your expectations and your intentions when it comes to your estate plan, because... those are the intangible things that are really hard to glean from a legal document.” Jessica Gibbs

“If you are not having these conversations with your kids, they don’t know where they’re going. They’re guessing, they’re coming up with things on the fly based on their own experience or what they’ve seen... and that’s not necessarily a perfect alignment with what you would want.” Jessica Gibbs

“You can’t read someone else’s mind, you know, right? That’s one of the basics of, you know, couples therapy, right? That you can’t guess what someone else is thinking.” Jessica Gibbs

“Bringing in your siblings to the conversation is going to be a challenge, but it’s such an important one to do while everyone is healthy.” Jessica Gibbs

Resources

• Total Family (https://www.totalfamily.io/)
• Monument Wealth (https://monumentwealthmanagement.com/)
• Between Sips Podcast (by Emily Harper & Jessica Gibbs) (https://monumentwealthmanagement.com/resources/podcasts/)

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

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We believe wealth is well-being. Subscribe to the Visionary Advisor Newsletter for practical tools and ideas to serve families across generations.
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You can hire the best investment manager in the world, but if a family’s stories are lost or never spoken aloud, resilience and wealth may not last. Most advisors overlook the power of storytelling, even though research shows it shapes legacy and fosters well-being across generations.

On this episode of Visionary Advisor, Alex Kirby (founder of Total Family) features Dr Robyn Fivush, psychologist at Emory University and co-creator of the influential Do You Know Scale. Dr Fivush’s decades of research reveal that family stories, shared at the dinner table or on the way to hockey, are a stronger predictor of a child’s resilience than income or education.

Alex and Dr Fivush explore what actually happens around family dinner tables, untangling myths about “storytelling families", the real power of intergenerational narratives, and why it’s rarely about a perfectly curated book or completing a questionnaire. Instead, it’s about how stories are shared, who tells them, and when the messy and the meaningful surface. The conversation also dives into oscillating family narratives (not just rags-to-riches), the evolving role of vulnerability, and what today’s advisors must know to support families beyond balance sheets.

Advisors will leave this episode with a new lens for legacy—and practical steps to help families connect, cope, and thrive.

What You’ll Learn in This Episode

• 00:00 Why sharing both failures and successes is essential for multi-generational resilience
• 00:39 The origins of the Do You Know Scale and what family dinner conversations predict about well-being
• 05:28 How intergenerational stories shape a child's ability to cope—with data from major life events like 9/11 and Covid-19
• 12:13 Why timing and authenticity matter more than “perfect” storytelling (and how to match stories to developmental stages)
• 21:46 How family stories are actually transmitted—not in epic retellings, but in everyday, unscripted exchanges
• 28:42 The three core types of family narratives—ascending, descending, oscillating—and why oscillating stories build the most resilience
• 40:10 Why women often play the role of family historian, and what this means for continuity, connection, and advisor relationships
• 42:49 Practical advice for advisors: how to help families share meaningful stories, foster vulnerability, and deepen legacy

Notable Quotes from Robyn Fivush

"Being vulnerable and talking about your failures as well as your successes is going to be really critical for the next generations to understand what goes into maintaining wealth."

"Intergenerational narratives provide models—I get it, I know where you are, I've been in a situation like that."

"It's not knowing facts. The more of these stories you know, the more you come from a family that tells stories on a regular basis."

"The oscillating story is a story of resilience. We face challenges, but we overcame... There’s always challenges, there’s always resources to help you build the resilience to overcome."

"Stories are not always told in their entirety at a sitting. They come up in bits and pieces, as it makes conversational sense."

Resources

• Do You Know Scale and Research by Dr. Robyn Fivush and Marshall Duke (https://www.psychologytoday.com/us/blog/the-stories-of-our-lives/201611/the-do-you-know-20-questions-about-family-stories)
• Psychology Today - Dr Robyn Fivush’s blog (https://www.psychologytoday.com/us/contributors/robyn-fivush-phd)
• Storyworthy by Matthew Dicks (https://www.storyworthybook.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.
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We believe wealth is well-being. Subscribe to the Visionary Advisor Newsletter for practical tools and ideas to serve families across generations.
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Most advisors gather clients for dinners and updates. But when it comes to building genuine connection – and trust that endures beyond markets or products – most conversations play it too safe.

On this episode of Visionary Advisor, Alex Kirby (founder of Total Family) sits down with Tim Brown, co-founder of Somos22, to unpack the 225-year-old Jeffersonian dinner format and why its architecture for trust-building is more relevant than ever for advisors hoping to matter across generations. Tim shares lessons from hosting over a hundred such gatherings for family offices, revealing how thoughtful curation, powerful questions, and a commitment to true connection can quietly determine financial and relational outcomes among wealthy families.

The conversation invites wealth advisors to reimagine the purpose of client gatherings, moving beyond transactional events to experiences where trust can compound. They explore the mechanics of running an unforgettable dinner: how to structure conversation, manage vulnerability, handle silence, and frame questions that move people past pleasantries and into meaning. Tim and Alex also discuss tension points — including what happens when conversations get “too real", why family dynamics require careful navigation, and how the right question can spark reflection that lasts long after dessert.

Expect practical insights for creating spaces where families (and their advisors) show up as people first — and where “connection capital" is measured by who returns your call when it matters.

What You’ll Learn in This Episode

• 04:27 The concept of “connection capital” and why high-trust relationships drive family outcomes
• 08:33 Essential elements and rules of a Jeffersonian dinner for advisors — from structure to group norms
• 11:01 Icebreaker questions that foster vulnerability and depth
• 14:26 How to match questions and topics to the makeup of your room (professionals vs. principals, spouses, multi-gen)
• 17:00 Practical logistics: food, venue, timing, seating, and creating the right ambiance
• 19:23 Navigating moments of silence or vulnerability as a moderator
• 23:29 Ideal group sizes — and why too few or too many can backfire
• 32:03 The topics that matter most to ultra-wealthy families (hint: it’s not portfolios or investments)
• 33:09 Special considerations for dinners involving spouses or multiple generations

Notable Quotes from Tim Brown

“The way we define connection capital is the measurable value of high trust relationships. Who trusts your judgment, who will return your call, who shows up when something actually matters.”

“Silence is welcome. There’s no pressure to perform here... We do not learn from experience. We learn from reflecting on experience.”

“You can overwhelm people with too many questions and not give them enough time to kind of catch their breath.”

“If you’re not getting nervous, then you’re not doing it right, I guess. These dinners matter so much to me — you matter so much to me.”

“The output of a Jeffersonian dinner is that people leave trusting each other a lot more, because you’re able to bring in the human element of their lives.”

Resources

• Somos 22 (https://somos22network.com/)
• Total Family (https://totalfamily.io/) 
• YPO Investing Network (https://www.ypo.org)
• Tiger 21 (https://tiger21.com)
• Swexan Hotel, Dallas (https://hotelswexan.com)

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.
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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.
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Advisors have heard it for decades: robots and technology are coming for your job, so what actually keeps you indispensable in a world awash with AI, automation, and fee compression?

In this episode of Visionary Advisor, host Alex Kirby (founder of Total Family) welcomes Rich Ryffel, Professor of Finance Practice and Executive Director of Business Leadership at Purdue University, Mitch Daniels School of Business, whose 35-year career offers a rare, long-lens perspective on the financial advice profession. Together, they unpack the anxieties and realities facing advisors as each new wave of technology promises to “replace” them, asking what, if anything, is truly different about the AI era.

This conversation explores the enduring value of quality human relationships, the shifting meaning of “excellence” in advising, and why complexity and trust, not access or product, are now the real differentiators. Rich and Alex also examine lessons from unreasonable hospitality in the restaurant world, the challenge of scaling high-touch service, and what new talent, and especially women, need from the profession as 100,000+ advisors retire in the coming decade.

The stakes are clear: advisors who cling to the old model risk obsolescence, but those willing to focus on authentic relationships, adaptive learning, and well-being can offer families something technology alone cannot.

What You’ll Learn in This Episode

• 00:00 Why great relationships, not products or platforms, remain the advisor’s defining edge
• 03:08 How past tech disruptions (dot-com, Internet, robos) compare to the current wave of AI
• 07:31 What “excellence” means for advisors in 1995 versus 2026, and what hasn’t changed
• 09:57 Why technical acumen matters more than ever, but empathy and context are irreplaceable
• 13:07 How complexity, not just wealth, has moved center stage for advisor value
• 24:34 What wealth advisors can learn from “unreasonable hospitality” in dining, and pitfalls to avoid when scaling it
• 35:17 The SUSUFU principle: set up, show up, and follow up, why urgency and reliability set you apart
• 42:22 What the looming wave of advisor retirements means for the next generation of talent, and especially for female advisors

Notable Quotes from Rich Ryffel

“The excellent advisors have great relationships, always have, always will have.”

“The IQ piece of the business is a race to the bottom. Empathy and trust are where advisors make a difference.”

“If you just follow up and act with urgency, you’re ahead of so many people.”

“Think about what problem an advisor is actually solving—not what they used to solve.”

“You help clients sleep better and dream bigger. Most people want a good night’s sleep—not just another account review.”

“It’s not just about being a jack of all trades. Know when to integrate, when to outsource, and where you uniquely add value.”

Resources

• Setting the Table by Danny Meyer (https://www.dannymeyer.com/book)
• Unreasonable Hospitality by Will Guidara (https://unreasonablehospitality.com/)
• Investopedia (https://www.investopedia.com/)
• The Modern (NYC, Danny Meyer restaurant) (https://www.themodernnyc.com/)
• Catbird Seat (Nashville restaurant) (https://thecatbirdseat.com/)

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.
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When a spouse dies or a marriage ends, most women leave their advisor. 

The real risk isn’t lost assets — it’s lost trust and connection that should never have been a single point of failure.

In this episode of Visionary Advisor, hosted by Alex Kirby (founder of Total Family), guests Katie Randall and Lisa Jones of Prime Capital Financial bring decades of experience working with women, couples, and families through life’s hardest transitions. Together, they reveal how most advisory practices are designed for men, ignoring the very clients who will soon control nearly all the money.

This conversation dives into why heirs, especially women, so often walk away and what it takes to build resilience into your practice. You’ll hear candid stories about shifting from jargon to plain language, embracing the “messy middle” of client emotions, and creating an environment where both partners and rising generations truly feel seen.

The discussion covers the communication gap between spouses, the risk of neglecting the unengaged partner, how to facilitate trust even mid-divorce, and actionable ways to elevate family conversations around values and legacy. The message is clear: the future belongs to the advisor who listens deeply, fosters safety, and serves the whole family — not just the one in the room.

What You’ll Learn in This Episode

• 00:00:18 Why the “widow exodus” is a design problem, not just a retention issue
• 00:01:47 The urgency of adapting your practice as women inherit the majority of wealth
• 00:03:40 How communication patterns differ between men and women — and why it matters
• 00:05:24 Practical ways to foster trust and make space for vulnerability in client meetings
• 00:11:12 Building genuine relationships with both spouses, not just the engaged partner
• 00:13:02 Techniques to defuse money tension between couples and promote active listening
• 00:32:01 Supporting grieving clients — why emotional presence matters more than products
• 00:40:26 The gap between perceived and actual listening among advisors (and how to close it)
• 00:43:14 Why using jargon and “advisor-speak” can alienate clients — and what to do instead
• 00:44:07 How women and men may approach legacy conversations differently

Notable Quotes from Katie Randall and Lisa Jones

“We have to stop putting things in terms of how advisors think and the way that we speak and just really, answer questions and ask questions in a way that clients ask them in, like, a very human way.” — Katie Randall

“Advisors are missing the mark. When there’s a death or a divorce, many times the female spouse will change advisors because she hasn’t felt seen or heard in the relationship.” — Lisa Jones

“We’re professional problem solvers, but first we really have to be professional problem finders.” — Katie Randall

“If you’re not creating space where somebody can cry in your office — and it happens at least once a week — you’re probably not going deep enough.” — Lisa Jones

“They don’t want to know what you know; they want to know that you care.” — Lisa Jones

“If the efficiency frontier and all this stuff is what you’re focused on, you’re missing what matters to clients.” — Katie Randall

Resources

• Total Family (https://www.totalfamily.io)
• Prime Capital (https://primefinanciallisa.com)
• JMP AI (https://jump.ai/)
• YouTube Channel: Katie Randall, CAIA® | Certified Advisor for Women (https://www.youtube.com/@moneymotherlode)
  
  
  

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.
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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.
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AI isn’t coming for advisors’ jobs. It is quietly reshaping what clients expect, how firms differentiate, and where true value lies. The challenge is simple: will you be transparent about the technology supporting your work or let clients fill in the blanks themselves?

In this episode of Visionary Advisor, Alex Kirby (founder of Total Family) sits down with Mat Matthews, Chief Product and Engineering Officer at Advisor360, for a candid conversation about the 2026 Connected Wealth Report and the realities of AI in wealth management. Mat brings a product leader’s clarity to what’s actually changing, what’s just noise, and what matters most for client relationships.

The discussion explores why most advisors use AI daily but rarely talk about it with clients and how this silence can create mistrust instead of confidence. Mat and Alex get practical about where AI is delivering value now, why trust still builds slowly, and how firms are scrambling to keep policies current as technology evolves. They also consider how clients’ own use of AI is raising the stakes for transparency and what it means for advisors to move from data wrangling to truly holistic guidance.

For advisors wrestling with rapid change, compliance pressures, and rising client expectations, this episode offers a grounded look at what it means to serve families well in a new era.

What You’ll Learn in This Episode

• 04:20 How advisor attitudes about AI have shifted from fear to guarded optimism within a year
• 05:30 Leading AI use cases today, including meeting summaries, CRM, and administrative workflows
• 05:57 Current boundaries around what advisors trust AI to handle, versus what stays human
• 09:13 Why developing clear policies around AI is now essential for your firm
• 20:28 The consequences of not proactively discussing AI with clients, and why avoidance is not neutral
• 25:08 How clients’ growing familiarity with AI affects their advisor relationships
• 29:48 What makes human judgment, empathy, and relationship-building irreplaceable
• 30:22 The expanding role of advisors as generalists managing the full picture of a client’s life, not just investments

Notable Quotes from Mat Matthews

“You’ve got this weird scenario where three quarters of the industry is benefiting from this new technology, but they’re barely mentioning it to the people it’s supposed to serve.”

“When advisors avoid the topic (AI), they’re not creating neutrality. They’re creating a vacuum. And the vacuum is going to get filled by the client.”

“Trust is the product in this industry. It’s not a feature. It is the actual service that’s being provided.”

“I think the firms play a big role in being on the forefront in saying, 'Here's how we’re using AI responsibly to provide you with better outcomes, with the guardrails and the safety controls that we know are important.'"

“If your role is just in data aggregation, to me that’s pretty small… The really good advisors are just going to be helping people with advice.”

Resources

• 2026 Connected Wealth Report, Advisor360
• Advisor360
• There’s An AI For That (daily newsletter)
• Total Family
• AI Tools
  • Claude
  • Google Gemini
  • ChatGPT
  • Perplexity
  • Lovable
• Harvard Business Review - The Future Is Shrouded in an AI Fog

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.
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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.
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Even the wealthiest families can be unprepared for their own complexity. Most advisors aren’t trained to handle what matters most: communication, culture, and preparing the next generation for leadership.

In this episode of Visionary Advisor, Alex Kirby (founder of Total Family) is joined by Mark Tepsich, co-author of the UBS Family Enterprise Governance Report. Mark and Alex dive into what governance really looks like for families averaging $2.4 billion in net worth and why many of the biggest lessons apply to families at any asset level. Their conversation goes far beyond documents, highlighting how culture—shared norms and values—shapes both continuity and risk.

They unpack the realities behind family constitutions, non-financial meetings, and family retreats, examining practical ways advisors can help clients strengthen alignment and connection. Mark shares why the highest payoff comes from face-to-face connection, how advisors can get over hesitation to lead these conversations, and why integrating the rising generation early is essential for legacy and trust.

This episode is a guide for advisors ready to see legacy as a lived, evolving process, not just a set of documents. It urges a move from portfolio talk to family engagement and challenges advisors to expand their comfort zone for deeper, longer-lasting relationships.

What You’ll Learn in This Episode

• Why the process of creating a family constitution is more valuable than the final document
• How highly intentional families keep governance relevant as family structures shift
• What non-financial family meetings look like—and why most families don’t have them
• Practical approaches for running meetings and retreats that build family connection
• How advisors can facilitate (or encourage) non-financial conversations, even without outside specialists
• The central role of culture, communication, and ongoing review in successful governance
• Why integrating the rising generation early leads to stronger stewardship and trust
• Ways to move beyond “financial capital” to include values, rituals, and family well-being

Notable Quotes from Mark Tepsich

“It all comes down to how are you preparing the next generation to navigate that enterprise. Which is really people-centric.”

“The value add is that process of talking about that stuff, of spending the time and actually memorializing it.”

“You don’t have to have a 400-page family constitution. In fact, I would say you shouldn’t, because you’re not going to know what’s in there.”

“Culture is our shared norms, which is how we do things, and our shared values.”

“If you freeze it, that means you can’t adapt as a family. And there’s one thing about a family since the beginning of time — you need to adapt to the evolving circumstance of your enterprise or the environment of the world around you.”

“There’s a risk in not having that conversation too. The bigger harm is not doing it.”

Resources

• UBS Family Enterprise Governance Report
• UBS Family Advisory and Philanthropy Toolkits
•

Send us feedback

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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

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We believe wealth is well-being. Subscribe to the Visionary Advisor Newsletter for practical tools and ideas to serve families across generations.
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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 

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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