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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