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Hawaii Retirement Show

Hawaii Retirement Show

Written by: Jason Cutitta CFP®
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About this listen

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 |Copyright 2023 All rights reserved. Economics Personal Finance
Episodes
  • Ep.#105: Cutting Through The Hype with Andy Panko, CFP®
    Jan 23 2026

    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.

    Website: https://www.hiretirementshow.com

    Email Us: aloha@hiretirementshow.com

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    59 mins
  • Ep.#104: Making Sense of Gold; History & Market Behavior
    Jan 11 2026

    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.

    Website: https://www.hiretirementshow.com

    Email Us: aloha@hiretirementshow.com

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    24 mins
  • Ep.#103: Taxation of Collectibles; Wine & When a Hobby becomes a Business.
    Jan 1 2026

    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.

    Website: https://www.hiretirementshow.com

    Email Us: aloha@hiretirementshow.com

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    19 mins
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