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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.

In this episode, Rory speaks with Will Hill, founder of Will Hill Consults, and John Fenton, CEO of John J. Fenton Executive Coaching, about their contributions to The Holistic Guide to Wealth Management and how firms can strengthen culture, manage change, and support their people. Will shares why firms need a repeatable process for change management, how to avoid shiny object syndrome, and the importance of aligning initiatives with purpose and client strategy. John highlights why culture starts with why, the role of psychological safety and trust in retaining talent, and how managers can be better supported through delegation, time management, and leadership development. Together, they explore how firms can cut through the noise, improve communication by eliminating hidden assumptions, and create environments where people feel valued and connected to something bigger than themselves. They also emphasize why investing in people at every level from staff to partners is the foundation for long-term growth and firm resilience. Want to know how to balance people, process, and purpose to build stronger and more resilient firms? Find out in this insightful conversation with Will Hill and John Fenton.

In this episode, Rory sits down with Christine Simone, founder of Caribou Wealth (now part of Move Health), to explore why healthcare planning is the missing piece in holistic advice for CPAs and advisors. Christine shares her journey of building a platform that helps firms support clients with Medicare, marketplace coverage, and employer plans—areas that are often overlooked despite being one of the top expenses in retirement. Discover how to identify client red flags, keep track of key enrollment deadlines, and use strategies like premium tax credits to reduce costs. Learn why healthcare can act as a barrier to big life transitions, such as starting a business or retiring before 65, and how addressing it empowers clients to move forward with clarity and confidence. Christine also unpacks how firms can implement healthcare planning without becoming insurance experts by partnering with the right resources and leveraging technology. Want to know how healthcare planning can save clients thousands and strengthen trust? Want to know the key dates and life events when healthcare needs to be addressed? Find out the answers to these questions and more in this insightful conversation with Christine Simone.

In this episode, Rory speaks with Loren Fogelman, founder of Business Success Solutions, and Mike Maksymiw, Executive Director of Aprio Firm Alliance, about how firms can adapt and thrive in a fast-moving profession. Loren explains why so many accountants undervalue their services and how shifting from hourly billing to value pricing can align firms more closely with client outcomes while boosting profitability. Mike shares ways practitioners can embrace vulnerability as a leadership strength and how to inspire teams to drive change. Want to know how to strengthen your value beyond compliance? Curious how to lead with empathy while preparing your firm for the future? Find out the answers to these questions and more in this conversation with Loren Fogelman and Mike Maksymiw.

In this episode, Rory speaks with BatSheva Goldstein, investment advisor, financial planner, and creator of Financial Date Discussion Cards, about how couples can have easier and more meaningful conversations around money. BatSheva shares how the cards help partners uncover their unique money stories, align values, and build common ground—even when they approach finances differently. She explains why money conflicts are rarely about math and more about what dollars represent in our lives. Through simple yet powerful questions like “What’s a financial decision you’re proud of?” and “What makes you feel rich?” couples can start with positive momentum, explore deeper values, and strengthen their financial teamwork. They also discuss how advisors can use tools like these to foster trust, improve client retention, and engage both partners before a meeting even begins. Want to learn how to turn money talks from stressful to collaborative? Curious how values-based conversations can improve relationships and financial outcomes? Find out the answers to these questions and more in this insightful discussion with BatSheva Goldstein.

In this episode, Rory sits down with Ben Taylor, CPA and CEO of SoftLedger, to explore how real-time accounting, automation, and an API-driven platform are transforming the finance function. Ben shares his journey from public accounting to co-founding a software company designed to solve the pain points he experienced firsthand. Discover how real-time data access and seamless integrations are eliminating the need for month-end closes and helping firms deliver strategic insights faster. Learn why modern finance teams must embrace a mindset shift—one that combines technical skill, data storytelling, and human judgment. Ben also unpacks how AI is reshaping customer support, accelerating product development, and allowing leaner teams to scale with speed. Want to know how low-code tools and real-time reporting are changing the game for practitioners? Curious how to tell a compelling story around the numbers? Find out the answers to these questions and more in this API-to-AI conversation with Ben Taylor. Contact Ben: [email protected]

In this episode, Rory speaks with Kris Lenz, founder of Kailos Marketing Lab and former creative leader at firms like Grant Thornton and MGO, to explore how AI is reshaping marketing for professional services. Kris shares how firms can use generative tools to brainstorm more efficiently, scale content creation, and streamline proposal and outreach workflows. He explains how voice and tone remain central even when using AI, and why being strategic with prompts and post-editing can make the difference between generic and standout content. The conversation also covers the importance of brand cohesion, the risks of relying too heavily on automation, and how smaller firms can elevate their presence without bloated teams or big budgets. Want to learn how to use AI to amplify your message while keeping it personal? Curious how to integrate creativity and consistency across your firm’s content? Find out the answers to these questions and more in this AI and marketing conversation with Kris Lenz. Website: https://www.kailos.ai/ Kris LinkedIn: https://www.linkedin.com/in/kristofer-lenz