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.

In this episode, Rory speaks with Erika Wasserman, Certified Financial Therapist, keynote speaker, and author of Conversations With Your Financial Therapist, about how our earliest money experiences shape financial decisions throughout life. Discover what financial therapy really is and why money challenges are rarely about the numbers alone. Erika shares her MONEY framework for improving money conversations, explains how childhood “money moments” influence adult behavior, and outlines practical ways CPAs and advisors can help clients navigate emotionally charged topics like parenting, caregiving, divorce, and retirement transitions. They explore how better questions, storytelling, and compassion can deepen trust, reduce shame, and improve follow-through. Erika also discusses how professionals can identify when mindset work is needed and how financial therapists complement traditional advisory services. Want to know how improving money conversations can strengthen client relationships and outcomes? Find out in this insightful conversation with Erika Wasserman.

In this episode, Rory speaks with Phil Whitman, President and CEO of Whitman Advisory, one of the leading advisory organizations serving CPA firms nationwide. Phil shares how his firm evolved from succession and M&A consulting into a multi-service advisory platform helping firms improve profitability, recruit talent, and prepare for the what comes next in the world of accounting. He explains how private equity has reshaped the accounting profession, what firms can learn from early deals like EisnerAmper, Citrin Cooperman, and Cherry Bekaert, and why 2026 could be “the year of the tuck-in.” Phil also outlines the four keys to building a world-class firm—communication, trust, partner alignment, and accountability—and why culture and capital structure matter as much as multiples. Want to know how CPAs can position their firms to attract investment, grow through acquisition, and thrive in the age of private equity? Find out in this conversation with Phil Whitman.

In this episode, Rory speaks with Dr. Sean Stein Smith, CPA, professor at Lehman College, Forbes contributor, and advisory board member of the Wall Street Blockchain Alliance, to explore how artificial intelligence and blockchain are transforming the accounting and advisory profession. Discover how blockchain delivers trust and transparency while AI drives speed, pattern recognition, and efficiency across payments, banking, finance and wealth management. Sean discusses how firms like BlackRock and SoFi are leveraging AI to automate decision-making and enhance client experience, and he shares his perspective on Sam Altman’s $1.4 trillion AI bet and whether we are in a bubble or a sustainable transformation. Find out why the real opportunity lies in combining technology with human insight and why communication, soft skills, or what he prefers to call business skills, will define the next generation of advisory professionals. Sean also shares how automation is shifting firms from transactions to transformation and why the CPA license remains a powerful mark of trust in a digital-first world. Want to know how CPAs and advisors can harness AI to elevate their services and strengthen client relationships? Find out in this AI & Blockchain podcast with Dr. Sean Stein Smith.

In this episode, Rory speaks with Dan Haylett, author of The Retirement You Didn’t See Coming and host of the Humans vs. Retirement podcast, about the psychological and emotional side of life after work. Dan explains why retirement is less of a math problem and more of a human transition, one that requires redefining purpose, identity, and structure. They discuss how couples can plan for “yours, mine, and ours” retirements, why clarity follows action, and how to overcome the productivity trap that often replaces purpose with busyness. Dan also shares the three stages of the Retirement Reinvention Curve, which are Release, Rebuild, and Reignite, along with the five pillars of a thriving retirement: purpose, identity, relationships, structure, and wellbeing. Want to know how advisors can guide clients through the messy middle and help them build a life of meaning beyond the spreadsheets? Find out in this insightful conversation with Dan Haylett.

In this episode, Rory speaks with Alex Bottom, CEO of Finology Sofware, and Ryan Galiotto, CFP®, CSLP®, founder of the Student Loan Help Network, about how advisors and CPAs can prepare for the sweeping changes coming to student loan planning. They discuss the One Big Beautiful Bill (OBBB) and how it will reshape repayment plans, extend terms, and impose new borrowing caps beginning in 2026. Alex explains how tax filing status and forgiveness rules can significantly impact repayment and why understanding these nuances is critical for CPAs. Ryan highlights the growing number of retirees carrying Parent PLUS loans and how this generational shift is redefining financial priorities for families. Together, they outline why student loan planning is moving from niche to mainstream and how practitioners can integrate it as a value-added service. Are you ready to help clients navigate the new repayment landscape? Want to know how to turn student loan guidance into an opportunity for deeper client relationships? Find out the answers to these questions and more in this important conversation with Alex Bottom and Ryan Galiotto.

In this episode, Rory speaks with Keith Friedman, CEO and founder of FBO Strategies and creator of the Carbyne Allocation®, about why life insurance deserves a fresh look as part of holistic planning. Keith addresses common concerns that permanent insurance is too costly, rigid, or underperforming, and explains how policy design and communication can change those perceptions. He notes that when structured appropriately, life insurance can provide flexibility, liquidity, and even options to help cover long-term care costs. The conversation explores how modern policies go beyond the death benefit to offer access to cash value and serve as a stabilizing element during market volatility. Keith also shares his perspective on the importance of transparency in compensation and why education is key to shifting industry perceptions. Want to know how CPAs and advisors can use life insurance to strengthen holistic financial plans? Find out in this insightful conversation with Keith Friedman.