Claim OwnershipHawaii Retirement Show
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The HI Retirement Show is a podcast dedicated to retirement planning and financial education for all of those who call Hawaii home. Hosted by Certified Financial Planner® Jason Cutitta
Hawaii | Financial Advisor | Certified Financial Planner® | Honolulu | Toba Financial | Retirement Planning | Investment Management | Tax Planning | Estate Planning | Life Insurance | Long Term Care | FERS Federal Employee Retirement System | ERS State of Hawaii Employee Retirement System |
Hawaii | Financial Advisor | Certified Financial Planner® | Honolulu | Toba Financial | Retirement Planning | Investment Management | Tax Planning | Estate Planning | Life Insurance | Long Term Care | FERS Federal Employee Retirement System | ERS State of Hawaii Employee Retirement System |
116 Episodes
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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.
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
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.
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
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.
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
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.
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
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.
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
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.
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
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
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
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.
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
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, and common pitfalls like overfunding or missing eligible employees. Whether you're a sole proprietor or part of a small team, this episode offers valuable insights on how a SEP-IRA can simplify retirement planning while maximizing tax benefits.
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
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 about unforgettable sessions at Waimea Bay, the physical and mental preparation behind big wave surfing, and how Clark continues to stay in peak condition as he gets older. They also explore how canoe paddling brings people together, fostering both community and connection to the ocean. It’s a thoughtful and uplifting episode that celebrates passion, purpose, and the power of staying active and engaged—no matter your age or the size of the wave.
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
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 draw from each lever, you can better manage taxes, mitigate market risks, and optimize your overall financial health in retirement.
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
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 economic forces that impact life and retirement in Hawaii.
Hawaii Economic Association: https://hawaiieconomicassociation.com
Seth Colby Substack: https://substack.com/@sethcolby
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
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://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
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 High-3 salary, incorrect service time, or applying the wrong multiplier, can lead to big surprises in retirement. He also breaks down the often-misunderstood FERS Retirement Supplement, a temporary but valuable bridge to Social Security. Jason shares practical steps to verify your records and avoid costly mistakes, because you only retire once, and the details matter.
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
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 looking to better understand how tax planning supports a confident, well-rounded retirement.
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
*The discussion is intended to be for general educational purposes and is not tax, legal, or investment advice for any individual. Jason and the Hawaii Retirement Show do not endorse Sean Mullaney, Mullaney Financial & Tax, Inc. and their services.
In this episode of the HI Retirement Show, Jason explores the overlooked problem of saving too much for retirement. Jason breaks down why rigid savings rules and fear-based habits can lead to stress and difficulty spending later in life, and highlights the importance of balance, flexibility, and defining your own sense of “enough.”
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
In this episode of the HI Retirement Show, Jason explores whether it makes sense to roll over your 401(k), TSP, or other employer retirement plan into an IRA. He covers the key benefits—like simplified finances, more investment options, and greater control over taxes—as well as potential drawbacks, such as losing certain early withdrawal options and creditor protections. Tune in to learn what to consider before making the move.
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
In this episode of the HI Retirement Show, Jason dives into the essential topic of managing tax obligations in retirement. He breaks down how estimated taxes work, when you're required to pay them, and how the IRS’s Safe Harbor provisions can help you avoid underpayment penalties. Jason also explains how to fine-tune your withholdings from Social Security benefits, pensions, and retirement account distributions like TSPs, 401(k)s, and 403(b)s to better align with your total tax liability.
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
In this episode of the Hawaii Retirement Show, Jason breaks down the difference between cognitive errors—thinking mistakes rooted in flawed logic or poor information processing—and emotional biases, which stem from feelings, impulses, and intuition. He highlights common pitfalls like conservatism bias, confirmation bias, overconfidence, and loss aversion, explaining how they influence investment decisions and contribute to market anomalies. Jason also shares practical ways to recognize and reduce these biases, from education and systematic strategies to working with an advisor for objectivity. The key takeaway: investing success is not just about numbers, but about managing psychology, discipline, and emotional control for the long run.
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
In this episode of The Hawaii Retirement Show, host Jason Cutitta, CFP®, welcomes back Andy Panko, CFP®, RICP®, TPCP®, EA, for a second time to dive into taxes in retirement. They cover a range of important topics, including estate and inheritance taxes, how capital gains tax brackets work, the IRA Pro Rata Rule, the pros and cons of non-deductible IRA vs. taxable brokerage contributions, the deductibility of long-term care premiums, and more!
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
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