Episode 18 - Death and Money Make People Funny™ with Rose Zealand

Episode 18 - Death and Money Make People Funny™ with Rose Zealand

Today we welcome Rose Zealand, founder of Golden Thread Collaborative [https://deathandmoney.com/], who brings a uniquely integrated approach to one of life's most challenging transitions. With credentials as a CERTIFIED FINANCIAL PLANNER™, Certified Financial Transitionist, and End of Life Doula—a combination she believes she alone currently holds—Rose serves people in their 40s and 50s (and beyond) who have received a terminal or life-threatening diagnosis and want support navigating both the practical and existential dimensions of dying too soon. Rose's path to this work is deeply personal. Her background spans pre-med biology, sustainability consulting, nonprofit work in community food systems, and an unexpected career in financial services. But the catalyzing moment came with her father's death four years ago. While present for his final six weeks, Rose experienced firsthand the gap between optimal planning windows and emotional readiness—and discovered an unexpected kind of magic in being present for death, much like being present for birth. Key Topics Covered: The Gap Between Urgency and Readiness - Why advisors' well-intentioned push to update beneficiaries, fund trusts, and complete documents often meets client resistance rooted in denial and emotional unreadiness The Role of Presence Over Platitudes - What to actually say (and not say) when clients receive a diagnosis—avoiding "I'm sorry," silver-lining statements, and premature problem-solving Death Doula as Planning Partner - How end-of-life doulas complement financial planners by providing deep discovery work, emotional regulation, and space to explore identity, meaning, and unfinished business Hidden Assets and Undisclosed Information - How neutral, non-judgmental presence creates safety for clients to reveal financial details, family dynamics, and conflicts that formal planning conversations might miss This episode offers profound insights for financial planners, financial coaches, and anyone navigating the intersection of money and mortality—one of life's most tender and transformative spaces. "The more that you can just be the calmest, quietest person in the room, that can create kind of a refuge feeling with the individual, which again, can open up more productive conversations and the potential for planning."

Episode 17 - Stock Ownership and Wealth Independence with Dale Hershman

Today we welcome Dale Hershman, founder of Florida-based Advice-Only firm Sick Advisory Services [https://www.sickadvisoryservices.com/]. Dale's path to advice-only planning is anything but conventional. While selling medical products by day, Dale built his own healthcare stock portfolio by night, eventually channeling that expertise into a blog (sickeconomics.com) and a series of books under his pen name. To his surprise, readers began purchasing his work and then calling him directly for advice. That unexpected demand led him to earn his Series 65 license—not to gather assets or sell commission products, but to serve the independent-minded entrepreneurs who naturally gravitated toward his philosophy. Key Topics Covered: * An Organic Evolution - How Dale moved from pharmaceutical sales to night-time author to licensed advisor, driven by a desire to own rather than just earn, and why he never wanted to build a traditional AUM practice * The Independent-Thinker Niche - Why Dale attracts self-made business owners—the pool service operator with 200 employees, the entrepreneur with 10 dry cleaners—who want a "money buddy" rather than someone managing their money * Three Flexible Service Models - His hourly option ($300/hour), starter package (four hours plus text follow-up for $918), and yearly subscription (~$2,900) designed to meet clients wherever they are * Stock as Ownership - Dale's "deprogramming" approach to investing, reframing stocks not as widgets to be traded but as ownership stakes in companies with management already working on your behalf * The Asset-Neutral Advantage - Why being a neutral player with no commissions or kickbacks resonates so strongly, allowing Dale to recommend real estate, annuities, or stocks without bias Dale emphasizes that sound investing principles apply regardless of net worth—he serves clients ranging from $250,000 to over $25 million with similar advice—and pushes back against the myth that wealthy people need exotic, expensive investments. His core message centers on financial literacy, automated saving, and understanding that once you've accumulated assets, those assets work for you. This episode offers a fresh perspective for advisors considering individual stock recommendations and consumers looking to overcome the activation energy of getting started with investing. "If you want to earn, you gotta learn. Hit the books. Knowledge is power."

Episode 16 - Strategic Hiring for Growing Advice-Only Practices with McKenzie Kleinhenz

Today we welcome McKenzie Kleinhenz, a hiring specialist at Simply Paraplanner who brings a unique perspective to the talent challenges facing Advice-Only firms. McKenzie's own career journey as a financial planner gives her deep insight into both sides of the hiring equation. Key Topics Covered: * The Remote Revolution - How COVID accelerated demand for flexible, remote positions and why this model particularly benefits advice-only firms that value efficiency and intentional growth * First Hire Strategy - Why Advice-Only firms tend to be more thoughtful about capacity and planning-focused roles, and how to identify whether your bottleneck is planning work versus administrative tasks * Hiring Intentionally vs. Reactively - The critical difference between hiring when you're overwhelmed ("I need them to start tomorrow") versus planning ahead and finding the right cultural and skill fit * Job Description Excellence - Specific tactics for creating compelling job postings that reflect your personality and firm culture while clearly articulating both current responsibilities and long-term growth opportunities * The Personality Factor - Strategies for assessing cultural fit in remote hiring, including involving trusted mentors in interviews and asking candidates to describe their professional personality in three words * Part-Time to Full-Time Growth - How flexible arrangements can start small (5-10 hours/week) and scale with both firm growth and individual capacity, creating win-win scenarios This episode provides essential insights for any Advice-Only advisor contemplating their first hire or looking to scale their practice thoughtfully. "There's not one right way to build a financial planning firm or career. The most successful firms are the ones that build something that aligns with how they want to work with the clients they want to serve."

Episode 15 - Systematic One-Time Planning with Jon Luskin

Today we're joined by Jon Luskin [https://jonluskin.com/], a San Diego-based financial planner who has built his entire practice around one simple philosophy: give clients everything they need to know in one comprehensive plan, then let them implement it themselves. Jon serves on the board of the John C. Bogle Center for Financial Literacy and co-hosts the Bogleheads on Investing podcast, bringing his passion for low-cost index fund investing to everything he does. Jon's journey to Advice-Only planning began in traditional high-fee AUM shops before taking an unconventional detour—a sabbatical with his wife that involved converting a cargo van and traveling to America's best barbecue spots. When Rick Ferri, his investing hero, reached out and suggested he start his own Advice-Only practice, Jon couldn't say no. Nearly five years later, he's completed almost 500 one-time financial plans using a systematic approach that's become a model for other advisors. Key Topics Covered: * The One-Time Model - How Jon's one-time comprehensive planning works, from 15-minute screener calls to 50-page deliverable write-ups that clients implement independently * Template-Driven Excellence - The evolution of Jon's 200-page planning template, refined through hundreds of client engagements and now available to other advisors looking to systematize their processes * The Bogleheads Connection - His role in the Bogleheads community, co-hosting their investing podcast, and how that platform has shaped his marketing * Business Model Trade-offs: The realities of always needing new clients with a one-time model versus the freedom from ongoing handholding and follow-up accountability Jon emphasizes that complexity doesn't guarantee better results, whether you're a DIY investor or an advisor. His systematic approach allows him to serve clients efficiently while maintaining the detailed, comprehensive planning that empowers people to take control of their financial lives. He's also working on a consumer book based on his template and building more community around his planning methodology. This episode offers valuable insights for advisors considering one-time planning models and anyone interested in how systematic processes can create both efficiency and excellent client outcomes. "Complexity rarely guarantees better results, especially for do-it-yourselfers because they're going to have a much harder time managing it themselves. Keep it simple, and that's going to increase your odds of success."

Episode 14 - Equity Compensation and International Gotchas with Anthony Lombard

Today we welcome Anthony Lombard, founder of Noteworthy Financial [https://www.noteworthy-financial.com/] based in Northern Virginia. Anthony brings 20+ years of experience across financial services and technology, having worked at Morgan Stanley, BBVA, and DocuSign before launching his own Advice-Only practice. His unique background also includes living internationally and experiencing firsthand the equity compensation tax surprises he now helps clients navigate. Key Topics Covered: * RSU Tax Surprises - How Restricted Stock Units create ordinary income when vesting, even without receiving cash, and why your W2 can be much higher than expected when your company goes public or has a liquidity event * International Tax Landmines - Why moving abroad as a US citizen creates complex filing requirements, including the dreaded PFIC (Passive Foreign Investment Company) rules that can turn simple foreign investing into a paperwork nightmare * The Roth IRA Reality Check - Why "tax-free is a local term" and your Roth IRA may not provide tax-free withdrawals when living in countries like France, Germany, or Australia * Planning and Prevention - Practical strategies for organizing equity compensation schedules, working with qualified international tax professionals, and avoiding common pitfalls Anthony emphasizes the power of knowledge and preparation when dealing with these complex scenarios. His experience living internationally and working in tech companies during high-growth periods gives him unique insight into challenges that many advisors rarely encounter but can have massive financial impacts on clients. This episode is essential listening for any advisor with clients in tech companies, anyone considering international moves, or professionals dealing with equity compensation packages. Make sure to stick around for Anthony's sage words of advice at the end: "I think it is wonderful to always be curious. Be curious about how the world works. Be curious about how people make decisions and the psychology around human interaction."