Hawaii Retirement Show

In this episode of The Hawaii Retirement Show, host Jason Cutitta, CFP® is joined by Andy Panko, CFP®, host of the Retirement Planning Education Podcast, to discuss real estate tax planning and the Section 121 home sale exclusion. Andy joins the show to explain how homeowners may be able to exclude up to $250,000 or $500,000 of gain when selling a primary residence, and why the rules are often mor...

In this episode of The Hawaii Retirement Show, host Jason Cutitta, CFP® is joined by Ben Carlson, CFA, Director of Institutional Asset Management at Ritholtz Wealth Management, co-host of the Animal Spirits podcast, and author of Risk & Reward. Ben joins the show to discuss timeless investing lessons around risk, diversification, market history, investor behavior, and long-term decision-making...

In this episode of The Hawaii Retirement Show, host Jason Cutitta, CFP® is joined by surfing legend Shane Dorian to discuss fitness, aging well, and how to stay strong, lean, mobile, and capable after 40.  The conversation explores why physical health is one of the most important retirement assets, especially for those who want to keep surfing, hiking, paddling, diving, and enjoying an active life...

In this episode of The Hawaii Retirement Show, host Jason Cutitta, CFP® is joined by Maddy Roche, Chief Growth Officer at Childfree Trust, to discuss estate planning, care planning, and legacy planning for people who do not have children. They explore why traditional estate planning assumptions may not always fit childfree adults, especially when there are no obvious heirs or family members expect...

In this episode of The Hawaii Retirement Show, host Jason Cutitta, CFP® is joined by Benjamin Brandt, CFP® to discuss how retirees and pre-retirees can think about balancing both life and money throughout retirement. They explore the role diversification and portfolio rebalancing can play in managing market volatility, along with the challenges of dealing with concentrated stock positions and high...

In this episode of The Hawaii Retirement Show, Jason breaks down how pensions, 401(k)s, and Social Security are taxed in retirement at both the federal and Hawaii state levels. He explains some of the biggest retirement tax misconceptions in Hawaii, including why pension income and 401(k) withdrawals are often treated differently for state tax purposes. He closes by highlighting how the mix of ret...

In this episode of The Hawaii Retirement Show, host Jason Cutitta, CFP® is joined by Rachel Inafuku, PhD of UHERO to break down key insights on Hawaii’s economy, including inequality, job opportunities, and the evolving role of education. They discuss why Hawaii appears more equal than other states despite its high cost of living, and how the state’s unique economic structure shapes wages and care...

In this episode of The Hawaii Retirement Show, host Jason Cutitta, CFP® is joined by Darcy Smoot, CFA to break down how market and economic cycles work and why they matter for investors. They discuss the key differences between markets and the economy, what drives each, and why markets tend to move ahead of economic data. The conversation highlights why timing cycles is so difficult and how invest...

In this episode of The Hawaii Retirement Show, host Jason Cutitta, CFP® is joined by Jim Saulnier, CFP® to focus on the core building blocks of a sound retirement plan. They discuss the importance of secure income to cover basic needs, maintaining a buffer for unexpected health and long-term care expenses, and the idea of a “fun number.” The conversation also highlights how spending can evolve thr...

In this episode of The Hawaii Retirement Show, Jason breaks down the IRS “Dirty Dozen” tax scams and the common tactics scammers use to create urgency, fear, and confusion. From phishing emails and AI-driven phone calls to fake charities and misleading social media tax advice, he explains how these schemes can lead to costly mistakes, audits, and penalties. He closes with simple, practical steps t...

In this episode of The Hawaii Retirement Show, host Jason Cutitta, CFP® is joined by estate planning attorney Stacy Takekawa to explain how probate works and how assets transfer after death. They discuss what probate is, when it’s required, and the key steps involved in the process, including the roles of personal representative, creditors, and the court. They also cover how probate works specific...

In this episode of The Hawaii Retirement Show, host Jason Cutitta, CFP® is joined by Andy Panko, CFP® to break down permanent life insurance, advisor credentials, and the flood of DIY retirement planning content online. They kick things off by explaining how Indexed Universal Life (IUL) works and why it’s so often misunderstood and oversold. They also touch on Infinite Banking, the overload of adv...

In this episode of The Hawaii Retirement Show, Jason steps back from the headlines to make sense of gold, what it is, why people care about it, and how it has actually behaved across different economic environments. Using history as the guide, he explains how gold has performed during inflationary periods and financial crises, and why it can underperform for long stretches when confidence in marke...

In this episode of The Hawaii Retirement Show, Jason breaks down the taxation of collectibles, using wine to explain how the IRS treats tangible assets that appreciate in value. He clarifies what the IRS considers a collectible, why these assets can face higher tax rates than stocks, and how long-term gains on collectibles are capped at 28%, with additional taxes potentially applying for higher-in...

In this episode of The Hawaii Retirement Show, Jason breaks down the Net Investment Income Tax, a 3.8 percent tax that applies to passive investment income for higher-income taxpayers. He explains when and why it was created, what types of income it covers, and how the income thresholds work, including why more people may be affected over time as incomes rise but the thresholds stay the same. Jaso...

In this episode of The Hawaii Retirement Show, Jason breaks down the Wealth Progression Framework, a simple roadmap that unifies several popular wealth level models into one clear structure. He explains why so many versions exist, the common themes they share, and how understanding your current “wealth level” can guide more confident financial decisions. Jason walks through the major stages, from...

In this episode of The Hawaii Retirement Show, host Jason Cutitta, CFP®, is joined by Candace Nakamoto of SHIP Hawaii to discuss Medicare and how SHIP Hawaii can help retirees navigate it. They cover the basics of Medicare Parts A, B, C, and D, along with Medigap and Prescription Drug Plans. Candace explains key enrollment periods, such as the Initial Enrollment Period and Open Enrollment, and dis...

In this episode of The Hawaii Retirement Show, Jason unpacks a major SECURE 2.0 change taking effect in 2026, the requirement that high-income earners make their catch-up contributions as Roth. He explains how the IRS’s final regulations define the wage threshold and what the update means for different plan sponsors. Jason breaks down how the mandate applies across various employer plans, the impl...

In this episode of The Hawaii Retirement Show, Jason explores the Simplified Employee Pension (SEP-IRA), a flexible, tax-advantaged retirement plan ideal for small business owners and the self-employed. He explains the key benefits, including high contribution limits, ease of setup, and the ability to make discretionary employer-only contributions. Jason also covers eligibility, tax advantages, an...

In this episode of The Hawaii Retirement Show, Jason sits down with legendary big wave surfer Clark Abbey for an inspiring and wide-ranging conversation about life, legacy, and the ocean. Clark shares stories from growing up in a multi-generational surfing family in Hawai‘i, offering a window into the mindset and discipline it takes to ride some of the world’s most powerful waves. Clark talks abou...

In this episode of The Hawaii Retirement Show, Jason explores the "three-legged stool" metaphor for retirement planning, with each leg representing Social Security, pensions, and personal retirement savings. He goes on to explain the concept of "income levers," where each retirement account and income source can be strategically turned on or off to fit your needs. By understanding how and when to...

In this episode of the HI Retirement Show, Jason is joined by Seth Colby, PhD, Hawaii’s Chief Economist, for a wide-ranging conversation about the state’s economic landscape. They explore key data and trends shaping Hawaii’s future, from an aging population and high cost of living to questions of growth and long-term resilience. A thoughtful discussion for anyone interested in understanding the ec...

In this episode of The Hawaii Retirement Show, Jason explains why filing for Social Security at 62 might actually be the smarter move. He breaks down when claiming early can reduce financial stress, protect your savings, and better fit your health or family situation, showing that the best time to file isn’t always about waiting the longest, but about what works best for your life. Website: https:...

In this episode of the HI Retirement Show, Jason tackles a critical issue for federal employees, miscalculating your FERS pension. With the recent federal shutdown top of mind, Jason opens with a quick check-in and a reminder that financial stress can be a great prompt to reassess your emergency savings. Then, he dives deep into how small errors in your FERS pension, like misunderstanding your Hig...

In this episode of the HI Retirement Show, Jason is joined by Sean Mullaney, an advice-only financial planner and co-author of Tax Planning To and Through Early Retirement. They dive into what effective tax planning looks like over a lifetime, covering key strategies for different phases of life—like Roth conversions, asset location, and tax-loss vs. tax-gain harvesting. A must-listen for anyone l...