Hawaii Retirement Show

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 no one right way to invest, and how our experiences, personalities, and values shape our relationship...

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 making the most of the time you have to explore. Lanai also shares his thoughts on food, common travel mist...

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 throughout retirement. Jim also shares how he used AI in the research and writing process and why professio...

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 coverage, changing plans, traveling with Medicare, and important considerations for Hawaii residents, c...

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 power of compounding, and what more than two centuries of financial booms, crashes, wars, inflation, i...

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, underwriting, premium increases, and the differences between traditional and hybrid policies. LLIS: https://llis....

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 planning priorities, spending, investing, identity, purpose, healthcare, and family conversations can change...

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 importance of flexibility over optimization, common challenges retirees face, and when it may make sense to...

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, longevity protection, income guarantees, liquidity and surrender charges, commissions, taxes, common sa...

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 between independent living, assisted living, memory care, and extended care, along with the signs that it ma...

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, inventory, buyer demand, interest rates, and current market conditions. The conversation also explores th...

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...