Hawaii Retirement Show

By Jason Cutitta, CFP®Business Education Investing

Hawaii Retirement Show episodes

September 29 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 throughout retirement. Jim also shares how he used AI in the research and writing process and why professional judgment remains essential as retirement planning tools become more powerful and accessible.
How To Lower Your Taxes in Retirement, Advanced Strategies for Social Security, Roth Conversions, RMDs, and Medicare by James Mahaney: Book on Amazon
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33 min
September 15 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 coverage, changing plans, traveling with Medicare, and important considerations for Hawaii residents, couples, veterans, and federal employees.
Boomer Benefits: https://boomerbenefits.com
Website: https://www.hiretirementshow.com
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45 min
September 08 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 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
Website: https://www.hiretirementshow.com
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43 min
September 02 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, underwriting, premium increases, and the differences between traditional and hybrid policies.
LLIS: https://llis.com/
Website: https://www.hiretirementshow.com
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36 min
August 25 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 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
Website: https://www.hiretirementshow.com
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48 min
August 20 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 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/
Website: https://www.hiretirementshow.com
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52 min
August 13 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, 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/
Website: https://www.hiretirementshow.com
Email Us: [email protected]
59 min
July 23 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 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/
Website: https://www.hiretirementshow.com
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41 min
July 16 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, 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
Website: https://www.hiretirementshow.com
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23 min
June 30 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 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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49 min

About Hawaii Retirement Show

From the publisher's feed

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.