Hawaii Retirement Show

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 may be time to consider a senior living community. The conversation also covers the emotional and financial challenges families face, common misconceptions about Medicare and long-term care, the role of long-term-care insurance, and how The Plaza helps residents transition as their needs change. With Hawaiʻi’s senior population continuing to grow, this episode offers practical guidance for retirees and adult children navigating important decisions about care, independence, and quality of life.
The Plaza Assisted Living:  https://www.theplazaassistedliving.com/
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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 the financial, practical, and emotional aspects of moving from a single-family home to a condominium or smaller property, including maintenance and insurance costs, association fees, decluttering, and preparing a home for sale.
Maila Gibson-Bandmann:  https://www.mailagibson.com
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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 more complicated than people expect.
The conversation covers how capital gain is calculated, the importance of basis and home improvement records, the ownership and use tests, and common planning issues when a primary residence is converted to a rental property. Jason and Andy also discuss depreciation recapture, nonqualified use, inherited property, gifting real estate to children, 1031 exchanges, selling a home in retirement, and how a large real estate sale can affect taxes, Medicare IRMAA, and overall retirement cash flow.
Example 1: Section 121 Partial Exclusion
Example 2: Section 121 Non-Qualified Use
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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.
The conversation covers why simple investing is not always easy, the difference between investing and gambling, the role of rebalancing and diversification, and why the stock market and the economy do not always move together. Jason and Ben also discuss how these lessons apply to retirees and pre-retirees who need to invest through retirement while balancing growth, income, and risk.
Ben's Book:  Risk & Reward
Ben's Blog, A Wealth of Common Sense:  https://www.awealthofcommonsense.com
 
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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 lifestyle. Shane discusses the philosophy behind Dorian Core Performance, his PRIME Method of training, and how strength, power, recovery, mobility, endurance, nutrition, and accountability all play a role in aging well. He also shares practical advice for surfers and active adults who want to continue doing what they love into their 40s, 50s, and beyond.
Dorian Core Performance:  https://doriancoreperformance.com
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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 expected to step in during an emergency.
The conversation also covers the key documents everyone should consider having in place, including trusts, powers of attorney, and medical decision-making documents. Maddy also explains how Childfree Trust helps members think through who will handle their affairs, how fiduciary support can work, what happens during cognitive decline or medical emergencies, and how childfree individuals can create a meaningful legacy beyond leaving assets to children.
Childfree Trust: https://www.childfreetrust.com
 
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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 highly appreciated investments.
The conversation also covers key retirement planning decisions such as when to begin mapping out a retirement plan, strategies around claiming Social Security versus drawing from investments first, and how pensions and Social Security can shape the role of a retirement nest egg. Ben also shares thoughts on transitioning into retirement with part-time work, the emotional and lifestyle considerations that come with it, and how AI may impact the future of DIY retirement and tax planning.
Benjamin Brandt, CFP®:  https://retirementstartstoday.com
 
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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 retirement income sources can have a major impact on your after-tax cash flow and overall retirement strategy.
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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 career outcomes.
The conversation explores the impact of job training programs like Good Jobs Hawaii, which industries are seeing the strongest wage growth, and how AI is reshaping the value of education by emphasizing critical thinking, adaptability, and non-routine skills. They close with a discussion on Hawaii’s housing market and insights from the UHERO Housing Factbook.
Rachel Inafuku, PhD:  https://uhero.hawaii.edu/people/rachel-inafuku/
UHERO: https://uhero.hawaii.edu
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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 investor behavior often leads to costly mistakes. They close with practical takeaways around staying diversified, rebalancing, and maintaining a disciplined, long-term mindset.
Nelson Capital Management:  https://www.nelsoncap.com
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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 throughout retirement and why it often makes sense to prioritize enjoyment earlier on, when health and flexibility are at their peak. They also touch on the future of the financial planning profession and the growing impact of AI.
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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 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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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.
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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.
 
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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.
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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
 
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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.
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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.
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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.
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*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.”
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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.
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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. 
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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.
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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!
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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.
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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.
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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/
 
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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.
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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
 
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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
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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.
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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 against appropriate standards. Plus, Jason breaks down common misconceptions and mistakes investors make when evaluating returns, giving you the tools to make smarter, more informed decisions for your financial future.
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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.
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In this episode of the HI Retirement Show, Jason explores Hawaii's 529 college savings plan and an exciting new benefit for State and City & County employees, automatic payroll deductions directly into the plan. He explains how 529 plans work, the potential tax advantages, and how this new feature makes saving for education easier and more accessible than ever. Whether you're a parent, grandparent, or just planning ahead, you'll learn how to make the most of this powerful tool.
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In this episode of the Hawaii Retirement Show, Jason is joined by Estate Planning attorney Stacy Takekawa for an insightful conversation on how estate planning fits into a well-rounded retirement plan. They review the basics of estate planning, discuss how to avoid common pitfalls, and explore how to ensure your wishes are carried out. This a must-listen for anyone preparing for the future.
Stacy Takekawa: stacy@takekawalaw.com | www.takekawalaw.com
 
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In this episode of the HI Retirement Show, Jason takes a closer look at annuities—what they are, how they work, and whether they belong in your financial plan. He also highlights common mistakes to avoid when considering annuities, helping you make more informed decisions about your retirement strategy.
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In this Episode of the HI Retirement Show, Jason briefly breaks down some things to consider when deciding whether or not to take a pension as a lump sum.  
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In this Episode of the HI Retirement Show, in light of the recent events, Jason discusses what issues to consider during a recession or market correction.  
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In this Episode of the HI Retirement Show, Jason breaks down the eligibility and other considerations pertaining to social security benefits for divorced individuals. 
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In this Episode of the HI Retirement Show, Jason is joined once again by Chris Naffziger to discuss what retirement means in the modern age. Chris also shares his experience in taking a mini-retirement several years ago.
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In this Episode of the HI Retirement Show, Jason breaks down the Social Security benefits available to surviving spouses.  "Survivor Benefit"
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In this Episode of the HI Retirement Show, Jason discusses how most of us will suffer from cognitive decline as we age, and how this can impact financial decisions.   Jason also touches on how our confidence in decision making remains high as we age and the potential role a Single-Premium Immediate Annuity can play in someones financial plan later in life. 
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In this Bonus Episode of the HI Retirement Show, Jason discusses some things to consider for any Federal Workers who have recently resigned or were laid off due to cuts.  
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In this Episode of the HI Retirement Show, Jason briefly breaks down the Social Security Spousal benefits and who is eligible to collect them.  
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In this Episode of the HI Retirement Show, Jason discusses some things to consider regarding employer retirement account rollovers and the pro-rata rule.  
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In this Episode of the HI Retirement Show, Jason the various ways in which your Social Security benefits may be reduced.  
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In this Episode of the HI Retirement Show, Jason discusses things to consider as you determine whether or not your rental property expenses are tax deductible.  
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In this Episode of the HI Retirement Show, Jason is joined by Certified Personal Trainer, Chris Naffziger to discuss health and fitness in retirement.  
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In this Episode of the HI Retirement Show, Jason discusses the Backdoor Roth IRA.
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In this Episode of the HI Retirement Show, Jason briefly talks through some things to consider regarding the State of Hawaii - Employees Retirement System recent Temporary Hazard Pay.  
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In this Episode of the HI Retirement Show, Jason breaks down the Backdoor Roth IRA.  
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In this Episode of the HI Retirement Show, Jason breaks down some considerations when deciding between Roth and Traditional contributions.
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In this Episode of the HI Retirement Show, Jason briefly breaks down how to determine if a distribution from a retirement account will be tax and penalty free.  
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In this Episode of the HI Retirement Show, Jason discusses the 10% penalty on Traditional IRA distributions and some of the exceptions to the penalty.  
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In this Episode of the HI Retirement Show, Jason various issues to consider as it relates to aging parents.  This includes issues related to cash flow & living arrangements, estate planning, insurance, tax planning, assets & debts, and more. 
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In this Episode of the HI Retirement Show, Jason discusses how to determine whether or not someone can contribute to a Roth IRA.   
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In this Episode of the HI Retirement Show, Jason breaks down the inflation adjustments to the State of Hawaii Employees Retirement System Pension as well as the Federal Employees Retirement System Pension.  
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In this Episode of the HI Retirement Show, Jason breaks down the similiarities and differences between the SEP-IRA and the Solo401(k).  
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In this Episode of the HI Retirement Show, Jason discusses the questions you need to ask to determine whether or not you can make a deductible IRA contribution or not.  
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In this Episode of the HI Retirement Show, Jason discusses the importance of not always focusing or chasing down more earnings and instead periodically checking back in on your burn (spending) to effectively better your overall financial position. 
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In this Episode of the HI Retirement Show, Jason discusses the taxation of gambling winnings.  This includes the reporting requirements of gambling winnings as income, regular gambling withholdings, and deductions for gambling losses. 
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In this Episode of the HI Retirement Show, Jason discusses how unused sick leave is calculated and factored in to your years of service.  
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In this Episode of the HI Retirement Show, Jason discusses the most common financial professional licenses and certifications.  
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In this Episode of the HI Retirement Show, Jason discusses the four main factors that impact your credit score.  
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In this Episode of the HI Retirement Show, Jason breaks down the basics of Qualified Charitable Distributions.   
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In this Episode of the HI Retirement Show, Jason breaks down Required Minimum Distributions.  He discusses what they are, when they need to be taken, how they are calculated, and more. 
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In this Episode of the HI Retirement Show, Jason shares his perspective on having an emergency fund.   
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In this Episode of the HI Retirement Show, Jason briefly breaks down Life Insurance and Annuities to their most basic and fundamental purpose.  
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In this Episode of the HI Retirement Show, Jason and Paul breakdown the different Survivor Annuity Elections for the FERS pension benefit.   This includes the Maximum Survivor Annuity, the Partial Survivor Annuity, the No Survivor Annuity, and a few others.  
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In this Episode of the HI Retirement Show, Jason and Paul discuss the “20 Most Common Investment Mistakes”. per the CFA Institute. In Part-2 of this two part series, they provide valuable insights into common mistakes 11 through 20 on the list.
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In this Episode of the HI Retirement Show, Jason and Paul discuss the “20 Most Common Investment Mistakes” per the CFA Institute. In Part-1 of this two part series, they provide valuable insights into common mistakes 1 through 10 on the list.
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Q&A Episode #5: What is a Sweep account?  What are some plans to look into to set up my child’s college fund?
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In this Episode of the HI Retirement Show, Jason and Paul discuss one way of figuring out how much you need to retire.  They talk through the assumptions that need to be made, how to figure out your projected expenses in retirement, analyzing your inflation adjusted lifetime income such as Social Security or a Pension, and then talking through how your retirement accounts fit into the retirement equation.
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In this Bonus Episode of the HI Retirement Show, Jason and Paul breakdown the recent ROTH update to the State of Hawaii’s 457, Island Savings Plan.  
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In this Holiday Episode of the HI Retirement Show, Jason and Paul discuss ways to not overspend, charitable giving, and find the best deals during the holiday season.  They also touch on using this time of year to reflect and appreciate those closest to us.
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In this Episode of the HI Retirement Show, Jason and Paul provide our listeners with an introduction to Social Security.  Their conversation covers a few historical and current facts, who qualifies for Social Security, when you can collect your benefit, how much your benefit will be reduced or increased depending on when you claim, the importance of setting up your ssa.gov account, and how Social Security fits into a retirement plan.
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In this Retirement Insights Episode of the HI Retirement Show, Jason and Paul are joined by Andy Panko, CFP® to talk about Taxes in Retirement.  The conversation covers a few different ways tax planning fits into retirement planning.  They discuss state taxes, the potential taxation of social security, IRMAA (Medicare Surcharges),  the use and taxation of brokerage accounts, and having tax diversification in your retirement.
Featuring:  Andy Panko - https://www.linkedin.com/in/andypanko/
 
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In this Episode of the HI Retirement Show, Jason and Paul discuss the current state of interest rates as it relates to debt/liabilities.  Their conversation covers historical interest rates, how long interest rates may last, and things to consider regarding various interest rate environments.
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In this Episode of the HI Retirement Show, Jason and Paul discuss the current state of interest rates as it relates to assets.  Their conversation covers historical interest rates, how long interest rates may last, and things to consider regarding various interest rate environments.
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In this Episode of the HI Retirement Show, Jason and Paul breakdown the different components of the computation used to determine the Federal Employee Retirement System benefit.   They discuss the “High-3 Average Salary”, Years of Service, and the Multiplier used in the benefit formula.  Lastly, they walk the listeners through an example computation.
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In this Episode of the HI Retirement Show, Jason and Paul breakdown the different components of the computation used to determine the State of Hawaii ERS benefits.   They discuss the “Average Final Compensation” (AFC), Years of Service, and the Multiplier used in the benefit formula.  Lastly, they walk the listeners through an example of the Hybrid Plan computation.
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In this Episode of the HI Retirement Show, Jason and Paul are joined by Reverse Mortgage Specialist, Wendy Oshiro.  The conversation includes an overview of what a Reverse Mortgage is, how they work, and things to consider in deciding if a Reverse Mortgage is right for you.
Featuring:  Wendy Oshiro - https://mutualreverse.com/lo/wendy-oshiro/
 
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In this Episode of the HI Retirement Show, Jason and Paul discuss “Diversification”.  Their conversation covers what Diversification is, why it is typically an integral part of investments for retirement planning, and how to look at Diversification as it relates to taxes. 
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In this Retirement Insights Episode of the HI Retirement Show, Jason and Paul are joined by Cody Garrett, CFP® to talk about F.I.R.E. (Financial Independence Retire Early).  The conversation includes an overview of what F.I.R.E. is and the various forms it comes in.  They also discuss the importance of being intentional with your spending, investing, and retirement planning while at the same time not neglecting all the non-financial aspects of your life.
Featuring:  Cody Garrett, CFP® 
25 Areas of Comprehensive Financial Planning:  https://www.kitces.com/wp-content/uploads/2021/12/02-Advice-Only-Planning-Topic-Areas.png
 
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Q&A Episode #4:  How much will my estimated benefit be for my ERS Pension?  How will WEP impact me as a Federal Employee?
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In this Episode of the HI Retirement Show, Jason and Paul breakdown the different age and years of service combinations to be eligible for the State of Hawaii ERS benefits. They discuss the normal and early retirement requirements for the various ERS plans including the Hybrid #1 (prior to July1, 2012), Hybrid #2 (after June 30, 2012), Non-Contributory, and the Contributory plans. 
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In this Episode of the HI Retirement Show, Jason and Paul breakdown the different age and years of service combinations to be eligible for the FERS benefits   This includes the four FERS benefit categories of Immediate, Early, Deferred, and Disability.  
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In this Retirement Insights Episode of the HI Retirement Show, Jason and Paul are joined by Donne Soga of Premier Benefits Consultants to discuss all things Medicare.  The conversation includes an overview of the various parts of Medicare (Part A, B, C, & D),  how to apply for Medicare, things to consider when choosing a Medicare Advantage (Part C) plan,  and reviewing or changing your Medicare Part C coverage.
Featuring:  Donne Soga - https://www.pbchawaii.com/donne
 
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In this Episode of the HI Retirement Show, Jason and Paul provide an introduction to Medicare.  They discuss the history of Medicare, how you pay into and receive Medicare, the four main parts to Medicare (Parts A, B, C, & D), how Medicare works in conjunction with other insurance, and what Medicare does not cover. 
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In this Episode of the HI Retirement Show, Jason and Paul talk all about life insurance.  They provide general overview of what life insurance is and discuss the similarities, differences, and general characteristics of the 4 main types of life insurance; Term, Whole Life, Universal Life, and Variable Life.  The episode concludes with a discussion on who needs life insurance and ways to determine how much life insurance someone might need.
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Q&A Episode #3: I worked for the state for 3 years, what do I do now that I left?  Should I put more into my TSP or pay down my mortgage?
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All about the 403b.  In this Episode of the HI Retirement Show, Jason and Paul breakdown the 403b available to the University of Hawaii and Department of Education employees.  The topics covered in this episode include explaining what the 403b plan is, who has access to it, why and how you should contribute, contribution limits, distribution rules at retirement, the importance of naming beneficiaries, and more.
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