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 to protect yourself, emphasizing the importance of slowing down, verifying information through IRS.gov, and working with a trusted professional when something doesn’t feel right.

IRS News Release:  https://www.irs.gov/newsroom/dirty-dozen-tax-scams-for-2026-irs-reminds-taxpayers-to-watch-out-for-dangerous-threats

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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 specifically in Hawaiʻi, common misconceptions about the process, and how proper estate planning, such as coordinating wills, trusts, and beneficiary designations, can help simplify things for families.

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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 advisor designations and licenses, and how listeners can filter signal from noise in today’s finfluencer-driven world.

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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 markets is strong.

Jason closes by framing gold realistically within a portfolio, emphasizing that it is best understood as insurance or a diversifier, not a growth asset. He explains why gold often disappoints in calm markets and why portfolio construction and risk management matter far more than chasing any single asset.

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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-income taxpayers.

Jason also walks through the critical distinctions between being a hobbyist, an investor, or a business, and why that line matters far more than most people realize. He explains how intent, frequency of sales, and recordkeeping drive tax treatment, when losses are deductible, and how activities like consignment sales or frequent trading can unintentionally trigger business taxation. He closes with practical planning takeaways, emphasizing documentation, holding periods, and awareness of higher tax exposure, reminding listeners that while collectibles can be enjoyable and profitable, the tax rules require careful attention.

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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.

Jason also walks through how the tax is calculated using the “lesser of” rule and gives simple examples to show how it works in practice. He closes with practical planning tips, noting that while the NIIT is not a major burden, it is important for investors and retirees to understand and factor into their tax planning, especially when dealing with capital gains, rental income, wage increases, or Roth conversions.

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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.

Jason also walks through how the tax is calculated using the “lesser of” rule and gives simple examples to show how it works in practice. He closes with practical planning tips, noting that while the NIIT is not a major burden, it is important for investors and retirees to understand and factor into their tax planning, especially when dealing with capital gains, rental income, wage increases, or Roth conversions.

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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 financial survival and stability to security, growth, independence, abundance, and legacy, highlighting the key challenges at each level and the strategies that help you keep moving forward.

He also connects the framework to the broader financial lifecycle, including accumulation, the transition into pre-retirement, and the Go Go, Slow Go, and No Go phases of retirement. Jason closes with a reminder to choose the model that resonates with you, act according to where you are today, and remember that money is ultimately a tool, not the goal.

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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 discusses considerations for federal, state, and county employees. Listeners will also learn how to access SHIP Hawaii’s services and how to get involved as a volunteer. This episode is packed with valuable information for those approaching Medicare eligibility!

SHIP Hawaii Website: https://www.hawaiiship.org

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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 implications for employees whose plans don’t offer Roth contributions, and why its impact may vary from one participant to another. He also explores Roth in-plan conversions, detailing how they work, which funds are eligible, the tax considerations, and the strategic reasons many savers use conversions to build tax-free assets or reduce future RMD exposure.

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