Hawaii Retirement Show
by Jason Cutitta, CFP®
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 Jason Cutitta, CFP® - Financial Advisor– Toba Financial LLC https://www.tobawealth.com Investment Advisory Services are offered through Toba Financial LLC, a Registered Investment Adviser offering advisory services in the State of Hawaii and in other jurisdictions where exempt from registration. Disclaimer: The opinions and statements presented on this show are for general information only and are not intended to provide specific advice or recommendations. Never make any investment or financial decisions based on information offered on this show without first consulting your financial, legal, or tax advisor. All economic and performance information mentioned on the show is historical in nature and is not indicative of any future results. All indices mentioned on
Episodes
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Ep.#127: How the Experts Invest Their Own Money with Brian Portnoy, CFA
In this episode of The Hawaii Retirement Show, Jason sits down with Brian Portnoy, CFA, founder of Shaping Wealth and co-author of How I Invest My Money, Volume Two, to explore how financial experts invest their own money. They discuss the personal stories behind investment decisions, why there's...
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Ep.#126: The Art of Traveling Well with Lanai Tabura
In this episode of The Hawaii Retirement Show, Jason sits down with Lanai Tabura to talk about the art of traveling well and the story behind Lanai’s Travel Club. They discuss how travel changes as we get older, choosing the right destinations and tours, balancing adventure with comfort, and…
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Ep.#125: Smarter Tax Planning in Retirement with James Mahaney
In this episode of The Hawaii Retirement Show, Jason is joined by James Mahaney CFP®,Principal at Mavericus Retirement Services and author of How to Lower Your Taxes in Retirement, to discuss Social Security taxation, Roth conversions, RMDs, asset location, and why tax planning should evolve...
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Ep.#124: Understanding Medicare & Avoiding Costly Mistakes with Danielle Roberts
In this episode of the Hawaii Retirement Show, Jason is joined by Danielle Roberts, co-founder of Boomer Benefits and author of 10 Costly Medicare Mistakes You Can’t Afford to Make. They discuss Medicare enrollment, common and costly mistakes, Medicare Advantage versus Medigap, prescription drug...
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Ep.#123: America's 250-Year Bull Market with Meb Faber
In this episode of The Hawaii Retirement Show, Jason is joined by Meb Faber, co-founder and Chief Investment Officer of Cambria Investment Management and author of Investing in America: The Rise of a 250-Year Bull Market. They explore the history of investing in the United States, the remarkable...
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Ep.#122: Understanding Long-Term Care Insurance with Taylor West of LLIS
In this episode of The Hawaii Retirement Show, Jason is joined by Taylor West of Low Load Insurance Solutions (LLIS) to explain the fundamentals of long-term care insurance. They discuss who should consider coverage, when to apply, how benefits are triggered, important policy features,...
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Ep.#121: Retirement as a Series of Transitions with Dana Anspach, CFP®, Author of Living Off Your Acorns
In this episode of The Hawaiʻi Retirement Show, Jason is joined by Dana Anspach, CFP®, RMA®, author of Living Off Your Acorns, to discuss retirement as a series of transitions rather than a single event. They explore the Pre-Go, Go-Go, Slow-Go, and No-Go phases of retirement, including how…
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Ep.#120: Retirement Planning in an Uncertain World with Roger Whitney
In this episode of The Hawaiʻi Retirement Show, host Jason Cutitta, CFP® is joined by Roger Whitney, CFP®, founder of the Rock Retirement Club and host of the Retirement Answer Man Podcast, to discuss retirement planning in an uncertain world. They explore the transition into retirement, the...
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Ep.#119: Annuities - The Good, The Bad, and Where They Fit with Tracy Lownsberry
In this episode of The Hawaii Retirement Show, host Jason Cutitta, CFP® is joined by Tracy Lownsberry, founder of Annuity Giants and owner of Up North Retirement, to discuss the good, the bad, and where annuities may fit in a retirement plan. The conversation covers different types of annuities,...
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Ep.#118: Planning Ahead for Senior Living in Hawaii with Tricia Medeiros of The Plaza Assisted Living
In this episode of The Hawaiʻi Retirement Show, host Jason Cutitta, CFP®, EA is joined by Tricia Medeiros, Chief Operating Officer of The Plaza Assisted Living, to discuss senior living options in Hawaiʻi and how families can plan ahead for future care needs. Tricia explains the differences…
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Ep.#117: Hawaii Real Estate in 2026 & Downsizing Tips with Maila Gibson-Bandmann
In this episode of The Hawaii Retirement Show, host Jason Cutitta, CFP® is joined by Maila Gibson-Bandmann, a Realtor with Coldwell Banker Realty, to discuss the Hawaiʻi real estate market in 2026 and what homeowners should consider when downsizing. Maila shares her perspective on home prices,...
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Ep.#116: Real Estate Tax Planning: Exclude up to $250k or $500k of Home Sale Gain with Andy Panko, CFP®
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…
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Ep.#115: Risk & Reward with Ben Carlson, Timeless Investing Lessons
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...
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Ep.#114: Staying Fit and Doing What You Love with Shane Dorian
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…
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Ep.#113: Estate Planning Without Children with Maddy Roche
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…
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Ep.#112: Rebalancing Life and Money in Retirement with Benjamin Brandt, CFP®
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...
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Ep.#111: Retirement Taxes in Hawaii: Pension, 401(k), and Social Security Explained
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)...
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Ep.#110: Hawaii Economics: Inequality, Jobs, and Future of Education | Rachel Inafuku, PhD
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…
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Ep.#109: Understanding Market & Economic Cycles with Darcy Smoot, CFA
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…
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Ep.#108: A Retirement Planning Framework with Jim Saulnier, CFP®
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...
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Ep.#107: Dirty Dozen Tax Scams for 2026
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…
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Ep.#106: Understanding Probate with Stacy Takekawa
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...
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Ep.#105: Cutting Through The Hype with Andy Panko, CFP®
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...
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Ep.#104: Making Sense of Gold; History & Market Behavior
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…
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Ep.#103: Taxation of Collectibles; Wine & When a Hobby becomes a Business.
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...
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Ep.#102: Net Investment Income Tax (NIIT)
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,...
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Ep.#101 Wealth Progression Framework & Financial Lifecycle
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...
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Ep.#100: Medicare Basics with SHIP Hawaii (State Health Insurance Assistance Program)
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....
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Ep.#99: Mandatory Roth Catch-Up Contributions & In-Plan Roth Conversions
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...
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Ep.#98: Understanding the SEP-IRA (Simplified Employee Pension)
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…
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Ep.#97: Beyond the Numbers with Big Wave Surfing Legend Clark Abbey
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…
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Ep.#96: Three-Legged Stool & Retirement Income Levers
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...
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Ep.#95: Understanding Hawaii's Economy with Chief Economist Seth Colby
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...
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Ep.#94: When Claiming Social Security Early Makes Sense
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…
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Ep.#93: Miscalculating Your FERS Pension & Understanding the FERS Retirement Supplement
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...
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Ep.#92: Talking Tax Planning with Sean Mullaney, CPA
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...
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Ep.#91: Are You Saving Too Much For Retirement?
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...
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Ep.#90: Should You Rollover Your Employer Sponsored Retirement Plan (401k, TSP, etc..) to an IRA?
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…
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Ep.#89: Estimated Taxes & Withholdings from Retirement Account Distributions.
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...
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Ep.#88: Exploring Investor Biases (Cognitive & Emotional)
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...
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Ep.#87: Taxes in Retirement with Andy Panko, CFP® (Part II)
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…
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Ep.#86: A Dynamic Withdrawal Strategy in Retirement
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,...
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Ep.#85: The Bucket Strategy in Retirement. (Pros, Cons, and Caveats)
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...
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Ep.#84: Beyond The Numbers with Kaipo Crowell
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…
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Ep.#83: The 4% Rule in Retirement. (Pros, Cons, and Caveats)
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...
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Ep.#82: Talking Private Equity with Professor Tray Spilker, PhD, CFA
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...
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Ep.#81: Hawaii Real Estate Update with James Chan
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...
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Ep.#80: Initial Observations & Key Points from the "Big Beautiful Bill".
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…
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Ep.#79: Rates of Return & Benchmarking | Hawaii Retirement Show
In this episode of the HI Retirement Show, Jason dives into the fundamentals of rates of return—what they are, how they're calculated, and why they matter for your retirement planning. He also explores the concept of benchmarking, helping you understand how to measure your portfolio’s performance...
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Ep.#78: What Hawaii Public Employees Need to Know About EUTF Medical Costs in Retirement | Hawaii Retirement Show
In this episode of the HI Retirement Show, Jason breaks down what Hawaii State and City & County employees need to know about EUTF medical costs in retirement, highlighting the employer contributions and financial considerations to help you prepare with confidence. Website:...
About this show
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
Jason Cutitta, CFP® - Financial Advisor– Toba Financial LLC https://www.tobawealth.com Investment Advisory Services are offered through Toba Financial LLC, a Registered Investment Adviser offering advisory services in the State of Hawaii and in other jurisdictions where exempt from registration.
Disclaimer: The opinions and statements presented on this show are for general information only and are not intended to provide specific advice or recommendations. Never make any investment or financial decisions based on information offered on this show without first consulting your financial, legal, or tax advisor. All economic and performance information mentioned on the show is historical in nature and is not indicative of any future results. All indices mentioned on
Hosted by
Jason Cutitta, CFP®