Advisors and AI: What’s Changed, What Hasn’t, and What’s Next with Mat Matthews, Advisor360

Advisors and AI: What’s Changed, What Hasn’t, and What’s Next with Mat Matthews, Advisor360

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 [https://www.linkedin.com/in/alex-kirby-tf/] (founder of Total Family [https://www.linkedin.com/company/totalfamily/posts/?feedView=all]) sits down with Mat Matthews [https://www.linkedin.com/in/matmathews/], Chief Product and Engineering Officer at Advisor360 [https://www.advisor360.com/], for a candid conversation about the 2026 Connected Wealth Report [https://www.advisor360.com/connected-wealth-report-2026] 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 [https://www.advisor360.com/connected-wealth-report-2026] * Advisor360 [https://www.advisor360.com/] * There’s An AI For That (daily newsletter) [https://theresanaiforthat.com/s/newsletter/] * Total Family [https://totalfamily.io/] * AI Tools * Claude [https://claude.ai/] * Google Gemini [https://gemini.google.com/] * ChatGPT [https://chatgpt.com/] * Perplexity [https://www.perplexity.ai/] * Lovable [https://lovable.dev/] * Harvard Business Review - The Future Is Shrouded in an AI Fog [https://hbr.org/2026/04/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 [https://totalfamily.io/visionary-advisor/visionary-advisory-hub] for practical tools and ideas to serve families across generations. Explore more at totalfamily.io [https://www.totalfamily.io/wealth-firms-] | Follow us on LinkedIn [https://www.linkedin.com/company/totalfamily/posts/?feedView=all] | Watch episode clips on YouTube [https://youtube.com/@visionaryadvisor?feature=shared] Send us feedback [https://www.buzzsprout.com/2449330/fan_mail/new] Stay Connected with Visionary Advisor We believe wealth is well-being. Subscribe to the Visionary Advisor Newsletter [https://www.totalfamily.io/visionaryadvisor] for practical tools and ideas to serve families across generations. Explore more at totalfamily.io [https://www.totalfamily.io/wealth-firms-] | Follow us on LinkedIn [https://www.linkedin.com/company/totalfamily/posts/?feedView=all] |  Watch episode clips on YouTube [https://youtube.com/@visionaryadvisor?feature=shared]

Lessons From Multi-Billion Dollar Families on Connection and Collaboration with Mark Tepsich, UBS

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 [https://www.linkedin.com/in/alex-kirby-tf/] (founder of Total Family [https://www.linkedin.com/company/totalfamily/posts/?feedView=all]) is joined by Mark Tepsich, [https://www.linkedin.com/in/mark-tepsich-88826b33] co-author of the UBS Family Enterprise Governance Report. [https://www.ubs.com/us/en/wealth-management/our-solutions/private-wealth-management/family-office-solutions/articles/agreus-family-enterprise-government-report.html] 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 [https://www.ubs.com/us/en/wealth-management/our-solutions/private-wealth-management/family-office-solutions/articles/agreus-family-enterprise-government-report.html]• UBS Family Advisory and Philanthropy Toolkits [https://www.ubs.com/us/en/wealth-management/our-solutions/private-wealth-management/family-advisory-philanthropy.html]• Send us feedback [https://www.buzzsprout.com/2449330/fan_mail/new] Stay Connected with Visionary Advisor We believe wealth is well-being. Subscribe to the Visionary Advisor Newsletter [https://www.totalfamily.io/visionaryadvisor] for practical tools and ideas to serve families across generations. Explore more at totalfamily.io [https://www.totalfamily.io/wealth-firms-] | Follow us on LinkedIn [https://www.linkedin.com/company/totalfamily/posts/?feedView=all] |  Watch episode clips on YouTube [https://youtube.com/@visionaryadvisor?feature=shared]

Legacy Letters Every Client Needs, with Blake Brewer

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 [https://www.linkedin.com/in/alex-kirby-tf/] (founder of Total Family [https://www.linkedin.com/company/totalfamily/posts/?feedView=all]) welcomes Blake Brewer [https://www.linkedin.com/in/blakecbrewer], founder of the Legacy Letter Challenge [https://www.legacyletter.com/], 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/ [https://www.legacyletter.com/]) • Total Family (https://totalfamily.io [https://totalfamily.io/]) Send us feedback [https://www.buzzsprout.com/twilio/text_messages/2449330/open_sms] Stay Connected with Visionary Advisor We believe wealth is well-being. Subscribe to the Visionary Advisor Newsletter [https://www.totalfamily.io/visionaryadvisor] for practical tools and ideas to serve families across generations. Explore more at totalfamily.io [https://www.totalfamily.io/wealth-firms-] | Follow us on LinkedIn [https://www.linkedin.com/company/totalfamily/posts/?feedView=all] | Watch episode clips on YouTube [https://youtube.com/@visionaryadvisor?feature=shared] Send us feedback [https://www.buzzsprout.com/2449330/fan_mail/new] Stay Connected with Visionary Advisor We believe wealth is well-being. Subscribe to the Visionary Advisor Newsletter [https://www.totalfamily.io/visionaryadvisor] for practical tools and ideas to serve families across generations. Explore more at totalfamily.io [https://www.totalfamily.io/wealth-firms-] | Follow us on LinkedIn [https://www.linkedin.com/company/totalfamily/posts/?feedView=all] |  Watch episode clips on YouTube [https://youtube.com/@visionaryadvisor?feature=shared]

Complete Family Wealth: The 5 Capitals, with Jay Hughes

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 [https://www.linkedin.com/in/alex-kirby-tf/] (founder, Total Family [https://www.linkedin.com/company/totalfamily/posts/?feedView=all]) is joined by James E. Hughes [https://jamesehughes.com/], 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 [https://www.amazon.com/Complete-Family-Wealth-Bloomberg-Hughes/dp/1119453216] * Where Are All the Customers' Yachts? [https://www.amazon.com/Customers-Yachts-Street-Investment-Classics/dp/0471770892]  * Total Family [https://totalfamily.io]  Send us feedback [https://www.buzzsprout.com/twilio/text_messages/2449330/open_sms] Stay Connected with Visionary Advisor We believe wealth is well-being. Subscribe to the Visionary Advisor Newsletter [https://www.totalfamily.io/visionaryadvisor] for practical tools and ideas to serve families across generations. Explore more at totalfamily.io [https://www.totalfamily.io/wealth-firms-] | Follow us on LinkedIn [https://www.linkedin.com/company/totalfamily/posts/?feedView=all] | Watch episode clips on YouTube [https://youtube.com/@visionaryadvisor?feature=shared] Send us feedback [https://www.buzzsprout.com/2449330/fan_mail/new] Stay Connected with Visionary Advisor We believe wealth is well-being. Subscribe to the Visionary Advisor Newsletter [https://www.totalfamily.io/visionaryadvisor] for practical tools and ideas to serve families across generations. Explore more at totalfamily.io [https://www.totalfamily.io/wealth-firms-] | Follow us on LinkedIn [https://www.linkedin.com/company/totalfamily/posts/?feedView=all] |  Watch episode clips on YouTube [https://youtube.com/@visionaryadvisor?feature=shared]

The Grief Tax: Showing Up for Families After Loss, with Ron Gura

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 [https://www.linkedin.com/in/alex-kirby-tf/], founder of Total Family, sits down with Ron Gura [https://www.linkedin.com/in/rongura/], co-founder of Empathy [ https://www.empathy.com/], to explore what happens when grief, finance, and responsibility collide. Ron shares insights from Empathy’s research report, The Grief Tax, [https://www.empathy.com/thegrieftax] 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 [https://www.empathy.com/thegrieftax?utm_source=chatgpt.com]  • Empathy  https://www.empathy.com/ [https://www.empathy.com/] Send us feedback [https://www.buzzsprout.com/2449330/fan_mail/new] Stay Connected with Visionary Advisor We believe wealth is well-being. Subscribe to the Visionary Advisor Newsletter [https://www.totalfamily.io/visionaryadvisor] for practical tools and ideas to serve families across generations. Explore more at totalfamily.io [https://www.totalfamily.io/wealth-firms-] | Follow us on LinkedIn [https://www.linkedin.com/company/totalfamily/posts/?feedView=all] |  Watch episode clips on YouTube [https://youtube.com/@visionaryadvisor?feature=shared]