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 |
103 Episodes
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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.
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
In this episode of the HI Retirement Show, Jason explores dynamic withdrawal strategies and flexible approaches to retirement income that adjust based on market performance, spending needs, and longevity considerations. He explains how these strategies differ from fixed withdrawal methods, highlighting the potential benefits of greater adaptability in uncertain markets. Jason gives a high-level breakdown of the guardrails method while weighing the pros and cons of these strategies. Whether you're nearing retirement or already in it, this episode offers valuable insights on how to create a more resilient income plan.
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
In this episode of the HI Retirement Show, Jason takes a deep dive into the bucket strategy, a popular retirement income planning approach designed to help retirees manage risk and maintain steady cash flow. He breaks down how the strategy works, including how to structure different “buckets” for short-, medium-, and long-term needs. Jason also explores the advantages and limitations of the bucket approach, as well as how it compares to other withdrawal strategies.
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
In this episode of The Hawaii Retirement Show, Jason is joined by Kaipo Crowell, a former senior civilian leader at Pearl Harbor Naval Shipyard, for a deep and thoughtful conversation that goes beyond the numbers. From reframing wealth, to investing in relationships, health, and time, Kaipo offers lessons rooted in real-life challenges and reflections.
He and Jason explore themes like influence, accountability, goal setting, ego vs. humility, and finding hope during difficult times. It’s a rich, reflective discussion that reminds us all that retirement isn’t just a financial milestone—it’s a mindset, a journey, and an opportunity to live with purpose.
Kaipo Crowell: https://www.linkedin.com/in/kaipo-crowell-217a44211/
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
In this episode of the HI Retirement Show, Jason takes a deep dive into the 4% rule, a widely used retirement strategy that helps determine how much you can safely withdraw from your portfolio each year. He unpacks the origins of the rule, explains how it works, and explores how it holds up in today’s market conditions. Jason also highlights key concerns and important considerations to keep in mind when applying the 4% rule to your own retirement plan.
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
In this episode of The Hawaii Retirement Show, Jason is joined by Dr. Tray Spilker, Finance Professor at the University of Hawaiʻi’s Shidler College of Business, for a deep dive into the world of private equity. They explore what private equity really is, how it works, and where it fits into the broader investment landscape.
Tray Spilker, PhD, CFA - Latest Research Paper: "Private Equity Fund Performance: A Time-Series Approach".
Official publication (behind paywall): https://www.sciencedirect.com/science/article/abs/pii/S0378426625000901
SSRN version (older version, publicly available): https://papers.ssrn.com/sol3/papers.cfm?abstract_id=3367079
Links to Tray's other research can also be found on my SSRN author page: https://papers.ssrn.com/sol3/cf_dev/AbsByAuth.cfm?per_id=959552
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
In this episode of the Hawaii Retirement Show, Real Estate Broker James Chan joins us to break down the latest trends in Hawaii’s housing market. We dive into how interest rates are impacting buying and selling decisions, explore the current state of single-family homes, condos, and the luxury market, and discuss whether investing in renovations and repairs is really worth it before selling your home. Plus, we touch on how online platforms like Zillow are shaping buyer expectations and influencing the market. Whether you're thinking of buying, selling, or just staying informed, this is a valuable conversation you won’t want to miss.
James Chan: https://www.instagram.com/jimmyboychan
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
In this episode of the Hawaii Retirement Show, Jason unpacks the recently passed "Big Beautiful Bill". He highlights several key provisions including the temporary raising of the SALT deduction cap, the new “Senior Bonus” deduction, the targeted tax breaks for tip income and overtime pay, and much more.
Website: https://www.hiretirementshow.com
Email Us: aloha@hiretirementshow.com
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