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In this episode, Rory speaks with Alexandre Lin, co-founder and CEO of Summit, a general ledger technology built for family offices, about the growing complexity of managing family wealth and how technology is changing the way accounting and advisory firms serve clients. Alexandre shares the personal story behind Summit, which began when he was unexpectedly tasked with managing his family’s businesses and entities across multiple countries and discovered how difficult traditional accounting software was for complex, multi-entity families. He explains why AI can become the connective layer between fragmented accounting, investment, CRM, and wealth management systems, while the general ledger remains the trusted source of financial truth. They also explore why relationships and trust may become an even greater competitive advantage as technology becomes commoditized, the impact of private equity consolidation on professional services, and why Alexandre chose profitability and patient capital over growth at all costs. Want to know how AI could reshape the technology stack for family offices and wealth management firms? Curious why trust and relationships may become the ultimate moat in an AI-driven world? Find out the answers to these questions and more in this forward-looking conversation with Alexandre Lin.

In this episode, Rory speaks with Marissa Messana, founder of Marigold Elite Partners, executive performance coach, former professional golfer, and former Sports Illustrated host, about helping high performers reach the next level without sacrificing what matters most. Marissa shares her journey from professional golf to entrepreneurship and explains how the same principles that drive elite athletes can help executives, entrepreneurs, and advisors perform at their best. She introduces her three-pillar framework of energy, mindset, and relationships, and explains why building a "daily mental gym" is just as important as maintaining physical fitness. They explore how golf becomes a mirror for leadership, decision making, and self-awareness, why many successful people unknowingly operate from limiting beliefs, and how intentional habits can create more fulfilling careers and stronger relationships. Want to know how to build a personal operating system that supports both performance and wellbeing? Curious how mastering yourself can become your greatest competitive advantage? Find out the answers to these questions and more in this insightful conversation with Marissa Messana.

In this episode, Rory speaks with Arthur Bonner, producer, writer, and showrunner of The Union Development Company, about the making of Playbook Finance, an unscripted television series and the deeper mission behind the project. Arthur shares his journey from growing up in Watts to building a career in Hollywood, producing content that tells authentic, character-driven stories. Together, they explore the difference between reality television, docuseries, and unscripted storytelling, and why the most compelling stories emerge when real people are given the space to share their hopes, fears, and aspirations. The conversation also pulls back the curtain on the production process, from long shoot days and story development to editing, archival footage, and finding the emotional moments that resonate with audiences. Most importantly, they discuss why Playbook Finance is about more than money or sports. It is about family, relationships, purpose, and understanding how our beliefs about money are shaped by the people and experiences around us. Want to know what goes into creating an unscripted television series? Curious how conversations about money can open the door to deeper discussions about meaning, wellbeing, and legacy? Find out the answers to these questions and more in this behind-the-scenes conversation with Arthur Bonner.

In this episode, Rory speaks with Bill Walton, founder of Bill Walton Sales Training, about how professionals can grow their businesses by embracing a more human-centered approach to sales in the age of AI. Drawing on more than 25 years of experience working with Fortune 500 companies and professional service firms, Bill explains why emotional intelligence, curiosity, and authentic conversations are becoming more important than ever. He shares practical strategies for building a repeatable sales process, leveraging subject matter experts effectively, telling compelling client stories, and generating referrals without feeling salesy. Bill also discusses the challenges facing today’s seller-doers, why energy management may be more important than time management, and how professionals can create stronger client relationships by leading with empathy and value. Want to know how to sell without sounding like a salesperson? Curious why EQ may be a bigger competitive advantage than AI? Find out the answers to these questions and more in this practical conversation with Bill Walton.

In this episode, Rory speaks with Blake Christian, tax partner at HCVT, about Opportunity Zones 2.0 and why renewed legislation is creating fresh momentum around tax-advantaged investing, rural development, operating businesses, and infrastructure projects. Blake breaks down how the Opportunity Zone program works, including tax deferral, basis step-ups, and the potential for tax-free appreciation after a 10-year hold. They discuss why OZ 2.0 is attracting increasing interest from private equity, venture capital, family offices, and entrepreneurs, particularly around operating businesses and AI infrastructure projects. Blake also explains the growing emphasis on rural communities, how Opportunity Zones are being used to support housing and manufacturing, and why proper structuring and CPA guidance are critical before triggering a capital gain. Want to understand how Opportunity Zones may shape the future of economic development, infrastructure, and tax planning? Curious why AI data centers and operating businesses could become the next major OZ opportunity? Find out in this episode.

In this episode, Rory speaks with Ohan Kayikchyan, PhD in Economics, CFP®, Registered Life Planner®, Enrolled Agent, and founder of Alohana Financial, about the deeper relationship between money, meaning, and purposeful living. Ohan shares his journey from immigrating to the United States from Armenia with limited English to building a life planning focused advisory practice centered on helping clients uncover what truly matters to them. Drawing from George Kinder’s EVOKE® Life Planning process, he explains why traditional financial planning often misses the emotional and behavioral side of money and how meaningful conversations can help clients align their finances with their values, relationships, and aspirations. They discuss the difference between meaning and purpose, why so many successful people still feel something is missing, and how practices like improv, reflection, and mindful spending can help individuals reconnect with themselves. Ohan also explores why “pay yourself first” is more behavioral than financial and how budgeting can become a mirror of our values rather than just a spreadsheet exercise. Want to know how better conversations can lead to a more fulfilling financial life? Curious how life planning can help clients move beyond achievement and toward alignment and purpose? Find out the answers to these questions and more in this thoughtful conversation with Ohan Kayikchyan. Alohana Movements Blog: https://alohanafinancial.com/what-is-an-alohana-moment/ *Rory Henry is a registered investment adviser representative of Arrowroot Family Office. This podcast is published independently through Advis-ROR®, an outside business activity, and does not represent the views of Arrowroot Family Office.  It is intended for informational and educational purposes only and does not constitute investment advice. Ohan Kayikchyan is not a client of Arrowroot nor was there any compensation for his inclusion in this podcast.

In this episode, Rory speaks with Mark Martukovich, Executive Director and Managing Partner of Business Advisory and Accounting Partners powered by Harness, about how CPA firms can shift from compliance-driven practices to high-value advisory services. Mark shares how he evolved his own firm over 12 years using the Practice Forward model, moving from a highly transactional tax practice to an advisory-centric operation with over 200 advisory engagements. He explains why the first conversation with any business owner should be about their exit, how to build a structured and scalable execution model from prospect screening to delivery, and why value-based pricing matters in an AI-driven world. They explore how Mark uses AI to run prospect tax strategy screeners against a curated database of strategies, why advisory is not additional work but a repackaging of knowledge firms already have, and how building structure around advisory conversations can strengthen both client outcomes and firm positioning. Want to know how to build a duplicatable advisory model that deepens client relationships and elevates your practice? Curious how AI and structured execution can move your firm from reactive to proactive? Find out the answers to these questions and more in this practical conversation with Mark Martukovich. "Rory Henry is a registered investment adviser representative of Arrowroot Family Office. This podcast is published independently through Advis-ROR®, an outside business activity, and does not represent the views of Arrowroot Family Office.  It is intended for informational and educational purposes only and does not constitute investment advice. Mark Martukovich is not a client of Arrowroot nor was there any compensation for his inclusion in this podcast."

In this episode, Rory speaks with Michael Kay, former CPA, CFP®, certified life planner, and author of How to Craft Your Chapter X, about why the most important retirement planning has nothing to do with money and everything to do with identity, purpose, and joy. Michael shares how decades of advising high-performing professionals revealed a consistent pattern: most people have no plan for who they'll be once the title is gone. He explains why curiosity is the antidote to identity loss, how embracing discomfort in retirement is a zero-risk proposition, and why grieving the end of a career is a necessary step most people skip. They explore the Wheel of Life as a diagnostic tool, why George Kinder's famous "third question" helps connect values to action, and how retirement reshapes relationships, not just individuals. Michael also shares how his monthly Zoom community gives men a safe space for vulnerability and why he replaced achievement-driven purpose with the Three G's: groundedness, growth, and generativity. Want to know how advisors can help clients, and themselves, craft a meaningful next chapter? Find out the answers to these questions and more in this deeply personal conversation with Michael Kay. "Rory Henry is a registered investment adviser representative of Arrowroot Family Office. This podcast is published independently through Advis-ROR®, an outside business activity, and does not represent the views of Arrowroot Family Office.  It is intended for informational and educational purposes only and does not constitute investment advice. Michael Kay is not a client of Arrowroot nor was there any compensation for his inclusion in this podcast."

In this episode, Rory sits down with Denise LeDuc Froemming, President and CEO of CalCPA, to explore how the accounting profession can modernize without losing the core foundation that makes it trusted. Discover why trust remains the non-negotiable center of the CPA profession even as private equity, AI, and evolving business models reshape the landscape. Denise shares a powerful call to action around storytelling, urging professionals to expand the narrative beyond tax and audit to showcase the diverse opportunities the CPA path unlocks—from entrepreneurship to wealth management and beyond. Learn why community is becoming strategic infrastructure in a hybrid world, how firms should think about private equity as “different, not binary,” and why the profession must ensure standards keep pace with innovation. Denise also challenges leaders to “lean into being bold and uncomfortable” as the industry evolves in real time. Are you telling a big enough story about what it means to be a CPA? And are you ready to modernize your practice without compromising the trust that defines it? Find out the answers to these questions and more in this timely and forward-looking conversation with Denise Froemming. "Rory Henry is a registered investment adviser representative of Arrowroot Family Office. This podcast is published independently through Advis-ROR®, an outside business activity, and does not represent the views of Arrowroot Family Office.  It is intended for informational and educational purposes only and does not constitute investment advice. Denise Froemming is not a client of Arrowroot nor was there any compensation for her inclusion in this podcast"

In this episode, Rory speaks with Sameer Munshi, America’s Behavioral Science and Simulation Leader at EY, about how behavioral science and AI-powered simulation are transforming the way financial firms test ideas, understand client behavior, and make strategic decisions. Sameer shares his journey from product development at Merrill Lynch to building applied behavioral science teams at EY, where he helps organizations design experiments that improve adoption, engagement, and real-world outcomes. He explains how AI simulation can recreate synthetic populations to test messaging, pricing strategies, and client interactions before they are deployed, shifting firms from guessing what clients might do to predicting how they will actually behave. They also explore the growing gap between what people say and what they do, why traditional research methods often fall short, and how behavioral insights can help advisors communicate more effectively in a rapidly changing world. Want to know how AI simulation could help advisors test strategies before implementing them with real clients? Curious how behavioral science can help financial professionals design better conversations and decisions? Find out the answers to these questions and more in this fascinating conversation with Sameer Munshi.

In this episode, Rory speaks with Nick Pasquarosa, Founder and CEO of Bookkeeper360, about building a modern accounting firm from the ground up and why innovation starts with listening to small business owners. Nick shares how a door-to-door side hustle in high school evolved into a nationwide cloud accounting firm serving nearly 1,000 clients with a fully remote team across 26 states. He explains how his role shifted from boots-on-the-ground bookkeeper to strategic CEO, and why leadership communities like EO, YPO, and Hampton helped accelerate that growth. The conversation dives into the firm’s technology roadmap, including the development of its proprietary AI tool BOLT, designed to deliver CFO-level insights at scale while preserving the human relationship. Nick also unpacks how AI is being used internally to surface advisory insights, streamline month-end analysis, and reduce burnout without sacrificing value. Want to know how firms can leverage technology without losing their human edge? Curious how AI can enhance advisory conversations rather than replace them? Find out the answers to these questions and more in this forward-looking conversation with Bookkeeper360's CEO Nick Pasquarosa.

In this episode, Rory speaks with Joe Pine, co-author of The Experience Economy and author of the new book The Transformation Economy, about the progression of economic value and why financial professionals are uniquely positioned to guide lasting change. Joe explains how we’ve moved from commodities to goods, services, and experiences and now into the Transformation Economy, where the true value lies in helping clients achieve their aspirations across health, wealth, wisdom, and purpose. He introduces the concept of the “aspirant,” explores why all transformation is identity change, and shares how preparation, reflection, and integration can turn ordinary client interactions into meaningful breakthroughs. They discuss why charging for outcomes aligns incentives, how AI can augment coaching, and why the future of advice is about guiding human flourishing, not just delivering a product or service. Want to know how to design client journeys that move beyond experiences and into true transformation? Curious how to become the guide to a clients’ hero’s journeys? Find out the answers to these questions and more in this forward-looking conversation with Joe Pine.

In this episode, Rory speaks with Carl Richards, creator of the Sketch Guy column and author of Your Money: Reimagining Wealth in 101 Simple Sketches, about why the real work of financial planning starts with better conversations, not better spreadsheets. Carl shares how his simple sketches became tools for clarity, helping clients rethink money through the lenses of attention, time, energy, and values, not just dollars. They explore why “enough” is not a number but a state of being, how spending awareness can replace shame with intention, and why small behavioral shifts often matter more than sophisticated strategies. Carl also explains why planning is not about predicting the future but about becoming less wrong over time, especially in a world where uncertainty is the norm. Want to know how advisors can help clients align their money with what truly matters? Curious how better questions lead to better outcomes than better answers? Find out the answers to these questions and more in this thoughtful and practical conversation with Carl Richards. • The link to order Carl's book on Amazon, or folks can head to their favorite local bookstore • The link to place a bulk order of Carl's book. Listeners can save an additional 5% by using the code YourMoney5 at checkout. • Social media links if you'd like to tag Carl: LinkedIn, X, Instagram.

In this episode, Rory speaks with Alan Whitman, former CEO and Chairman of Baker Tilly, new CEO of Nichols Cauley, and author of Break the Mold: How to Achieve Transformational Change, Scale, and Growth Simultaneously. Discover how Alan led Baker Tilly through 3x revenue growth and over 20 acquisitions—not by chasing numbers, but by changing mindsets. Learn why strategy isn’t about activity, but about clarity of direction, and how firms can grow by building “communication, sales, and talent engines” that scale through systems, not individual effort. Alan outlines why “bigger isn’t better—better is better,” how language creates alignment, and why discipline equals freedom in partner-led firms. He also reveals insights from his new role leading a private equity–backed multidisciplinary platform focused on serving SMBs in the Southeast. Want to know what Alan means by “fist to five,” “sugar highs,” and freedom within a framework? Find out the answers to these questions and more in this Break the Mold conversation with Alan Whitman.

In this Best of 2025 episode, Rory brings together standout moments from conversations across accounting, wealth management, behavioral finance, and technology that all point to one theme: real progress happens when advisors focus on people, not just numbers. From reframing retirement as a question of identity and purpose, to understanding why money decisions are deeply emotional, guests explore how human behavior shapes financial outcomes. The episode also highlights how AI and blockchain are moving from buzzwords to real tools, why holistic advice requires collaboration across disciplines, and how better questions can lead to stronger relationships and better client follow-through. Whether the topic is student loans showing up later in life, navigating firm leadership and deal structures, or helping clients align values with decisions, this episode reflects the evolving role of the advisor as guide, partner, and trusted voice. Want to hear the moments that shaped the conversation this year and the insights that will carry into what’s next? Find out in this Best of 2025 episode.