Hawaii Retirement Show

Jason Cutitta, CFP®

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 Hawaii | Financial Advisor | Certified Financial Planner® | Honolulu | Toba Financial | Retirement Planning | Investment Management | Tax Planning | Estate Planning | Life Insurance | Long Term Care | FERS Federal Employee Retirement System | ERS State of Hawaii Employee Retirement System |

  1. 22h ago

    Ep.#114: Staying Fit and Doing What You Love with Shane Dorian

    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 Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

    53 min

  2. Jun 3

    Ep.#113: Estate Planning Without Children with Maddy Roche

    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   Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

    32 min

  3. May 19

    Ep.#112: Rebalancing Life and Money in Retirement with Benjamin Brandt, CFP®

    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   Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

    44 min

  4. May 12

    Ep.#111: Retirement Taxes in Hawaii: Pension, 401(k), and Social Security Explained

    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. Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

    20 min

  5. Apr 18

    Ep.#110: Hawaii Economics: Inequality, Jobs, and Future of Education | Rachel Inafuku, PhD

    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 Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

    38 min

  6. Apr 1

    Ep.#109: Understanding Market & Economic Cycles with Darcy Smoot, CFA

    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 Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

    48 min

  7. Mar 25

    Ep.#108: A Retirement Planning Framework with Jim Saulnier, CFP®

    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. Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

    1h 5m

  8. Mar 21

    Ep.#107: Dirty Dozen Tax Scams for 2026

    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   Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

    23 min
See All (100)

Ratings & Reviews

4.9
out of 5
11 Ratings

About

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 Hawaii | Financial Advisor | Certified Financial Planner® | Honolulu | Toba Financial | Retirement Planning | Investment Management | Tax Planning | Estate Planning | Life Insurance | Long Term Care | FERS Federal Employee Retirement System | ERS State of Hawaii Employee Retirement System |

Information

  • Creator
    Jason Cutitta, CFP®
  • Years Active
    2023 - 2026
  • Episodes
    100
  • Rating
    Clean
  • Copyright
    © Copyright 2023 All rights reserved.
  • Show Website
    Hawaii Retirement Show

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