Wicked Pissah Podcast

The Wicked Pissah Podcast, brought to you by the Financial Planning Association of New England (FPA of New England), features discussions for financial professionals including topics of financial planning, recent or future events in the financial services industry, and interactions with influential speakers from across the industry. Additionally, the educational program will review the latest updates and announcements surrounding the New England chapter of FPA. Join us and listen in for engaging discussions and insightful content!

#300 - 300 Episodes Later: What Financial Advisors Have Learned Along the Way 09/15/2026

#300 - 300 Episodes Later: What Financial Advisors Have Learned Along the Way What can 300 conversations teach you about becoming a better financial advisor? For the 300th episode of the Wicked Pissah Podcast, past and present hosts come together for a conversation about the ideas, people and experiences that have shaped the show and, in many cases, their own careers and practices. Michael Connaughton and Corey Christiana are joined by former hosts Chris Boyd, Brad Wright and Kathleen Keneally to look back at how a podcast that began as a way to extend the reach of FPA New England programming grew into 300 episodes of conversations with advisors, authors, industry leaders, technology companies and subject-matter experts. But this isn't simply a trip down memory lane. The group talks about something every advisor can relate to: How do you keep learning while you're busy actually running a practice and serving clients? Over the years, hosts have used questions coming directly from their own practices to find guests and topics. Those conversations have introduced them to new technology, planning strategies, marketing ideas and resources they could bring back to their firms and, sometimes, directly to their clients. You'll also hear how participating in the financial planning community can create opportunities you don't necessarily anticipate. Kathleen shares how stepping outside her comfort zone as an introvert led to four years of conversations with people she might never otherwise have had the opportunity to sit down with. The hosts reflect on career decisions, launching firms, learning from other practitioners and the value of seeing other advisors openly share how they approach the profession. And then there's the question of what happens next. The group looks ahead at AI, technology, video and the increasingly human side of financial advice, including a prediction that Wicked Pissah could eventually reach 1,000 episodes. Whether you've listened since the beginning or have never heard an episode, Episode 300 is a reminder that some of the best professional development doesn't come from having all the answers. It comes from knowing who to ask, staying curious and being willing to learn from other people in the profession. 300 episodes down. Only 700 to go. /episode/index/show/wickedpissahpodcast/id/42889790

#299 - When Student Loans Get Complicated: What Advisors Need to Know with Emma Crawford, CFP®, CSLP® 08/25/2026

#299 - When Student Loans Get Complicated: What Advisors Need to Know with Emma Crawford, CFP®, CSLP® Federal student loan planning has become increasingly complex, and for financial advisors, keeping up with changing repayment plans, forgiveness programs, eligibility rules, and deadlines can feel like a specialty all its own. In this episode of the Wicked Pissah Podcast, Jackie Walsh, CPA, CFP®, sits down with Emma Crawford, CFP®, CSLP®, founder of October Loan Strategies, a firm dedicated exclusively to helping borrowers navigate federal student loan repayment and forgiveness. Emma has consulted on more than $200 million in student loan debt and helped clients secure more than $10 million in forgiveness. Much of her work is done in collaboration with financial advisors who bring her in as a student loan specialist for their clients. Emma and Jackie discuss when an advisor may be able to handle student loan planning internally and when it makes sense to bring in specialized expertise. Six-figure loan balances, Public Service Loan Forgiveness, changing income-driven repayment options, uncertain forgiveness credit, and clients transitioning from the SAVE forbearance can all create planning questions that extend well beyond simply determining a monthly payment. They also challenge one of the most common assumptions about debt: that paying it off as quickly as possible is always the best financial decision. Emma explains why some borrowers may be better served pursuing forgiveness and directing available cash toward other financial priorities. For advisors, that means evaluating student loans within the context of the client's entire financial plan rather than treating the debt as an isolated problem. The conversation also explores the Certified Student Loan Professional designation, resources advisors can use to stay current, and how student loan specialists and financial planners can collaborate to provide more comprehensive advice. In this episode: When advisors should consider bringing in a student loan specialist How student loan planning fits into comprehensive financial planning Navigating income-driven repayment and forgiveness strategies Why paying student loans off faster isn't always the best answer Public Service Loan Forgiveness and forgiveness credit How repayment changes can affect a client's cash flow Evaluating student loans alongside other financial goals Resources advisors can use to stay current What the CSLP® designation involves How advisors can outsource student loan planning while remaining involved in the client relationship For advisors working with clients carrying federal student loan debt, this episode is a reminder that the right strategy isn't necessarily about eliminating debt as quickly as possible. It's about understanding the rules, evaluating the tradeoffs, and finding the strategy that best supports the client's bigger financial picture. /episode/index/show/wickedpissahpodcast/id/42508545

#298 - Inside CFP Board: CEO K. Dane Snowden Talks Awareness, Inclusion, and What's Next 08/18/2026

#297 - Long-Term Care Planning: Helping Clients Navigate Risk, Cost, and Coverage 08/11/2026

#296 - Starting a Career in Financial Planning: Paul Gaudio, CFP® on FPA NexGen and Professional Growth 08/04/2026

#295 - Modern Portfolio Optimization, Direct Indexing & ETF Investing with Robert Michaud 07/28/2026

#294 - The New Growth Engine: How AI Is Reshaping Advisor Marketing with Ian Karnell 07/16/2026

#293 - The Social Security timeline may be shorter than expected so what does that mean for your retirement? 06/23/2026

#292 - Research and Reporting with YCharts’ Jeff Juracka 05/05/2026

#291 - Before It Breaks: Spotting Financial Red Flags in Aging Parents 04/28/2026

#290 - Longevity Planning with Eliot Weissberg 04/21/2026

#289 - Treating Your Health Like a Financial Asset - with Stevyn Guinnip 04/14/2026

#288 - Andrea Schlapia: Founder and CEO of Ironstone Business Coaching 04/07/2026

#287 - The AI-Powered Growth Playbook for Advisors with Michael Barrasso 03/31/2026

#286 - Save Time, Add Value: How Advisors Are Using AI-Powered Tax Research with Blue J 03/24/2026

#285 - Hidden Assets, Red Flags, and the Truth in the Numbers – with Sara Nanchanatt, CPA/CFF 03/10/2026

#284- Solving the Financial Planning Gaps for Child-Free Clients with Dr. Jay Zigmont, PhD, MBA, CFP® 02/24/2026

#284- Solving the Financial Planning Gaps for Child-Free Clients with Dr. Jay Zigmont, PhD, MBA, CFP® Kathleen and Amy speak with Dr. Jay Zigmont, PhD, CFP®, founder of Child Free Wealth and Child Free Trust, a fiduciary solution built specifically for the growing population of adults without children. Dr. Zigmont is on a mission to address what he calls the “fiduciary void” for the roughly 25% of U.S. adults who are child-free yet are still served by an industry that typically assumes every client has (or will have) kids. Jay shares his personal path from healthcare leadership and academia to financial planning, and what he discovered while earning his CFP®: the standard planning “life script” is baked into the education, tools, and assumptions of our profession. That insight led him to research child-free households, write books on the topic, and ultimately build a planning model aligned with child-free client goals—including a flat annual fee structure designed to eliminate conflicts that can arise when clients want to intentionally spend down assets. We discuss: Why traditional AUM pricing can clash with “Die With Zero” goals How Jay uses a “Die With Zero Safety Net” approach, including long-term care planning, delayed Social Security, and a lower Monte Carlo target paired with ongoing adjustments The estate planning reality for child-free adults—why many don’t have documents in place, and how the system assumes a next-of-kin safety net How Child Free Trust works as a nationwide backstop for medical and financial decision-making (POA, executor, trustee), coordinated with care teams and 24/7 support Why long-term care planning is a fiduciary responsibility for every advisor—especially for solo agers—and how clients weigh self-insuring vs. standalone coverage This episode is a practical, thought-provoking look at how our planning process, tools, and business models may need to evolve to better serve a large (and growing) segment of clients—particularly those navigating retirement and aging without children. /episode/index/show/wickedpissahpodcast/id/40227800