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, innovation, and economic change can teach today’s investors. Meb also discusses diversification, investor behavior, and why maintaining perspective and a long-term mindset may be among an investor’s greatest advantages.

Meb Faber:  https://mebfaber.com

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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.com/

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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 along the way.

Dana Anspach, CFP®, RMA®: https://www.linkedin.com/in/danaanspach/

Living Off Your Acorns:  Book

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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 work with a financial advisor.

Roger Whitney:  https://www.rogerwhitney.com/

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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 sales practices, and how to evaluate whether an annuity is appropriate for a particular retirement strategy. Jason and Tracy also discuss the importance of understanding the guarantees, costs, tradeoffs, and alternatives before committing to an annuity contract.

Tracy Lownsberry: https://www.linkedin.com/in/tracy-lownsberry/

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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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