Jason Cutitta, CFP®

Hawaii Retirement Show

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. Disclaimer: The opinions and statements presented on this show are for general information only and are not intended t...

Author

Jason Cutitta, CFP®

Category

Education

Latest episode

Jun 30, 2026

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Episodes

Employer Retirement Account Rollovers & Pro-Rata Rule | Hawaii Retirement Show 20.02.2025

In this Episode of the HI Retirement Show, Jason discusses some things to consider regarding employer retirement account rollovers and the pro-rata rule.   Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

Will My Social Security Benefits Be Reduced? | Hawaii Retirement Show 16.02.2025

In this Episode of the HI Retirement Show, Jason the various ways in which your Social Security benefits may be reduced.   Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

Is My Rental Property Tax Deductible? | Hawaii Retirement Show 02.02.2025

In this Episode of the HI Retirement Show, Jason discusses things to consider as you determine whether or not your rental property expenses are tax deductible.   Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

Health & Fitness in Retirement with Chris Naffziger | Hawaii Retirement Show 26.01.2025

In this Episode of the HI Retirement Show, Jason is joined by Certified Personal Trainer, Chris Naffziger to discuss health and fitness in retirement.   Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

Can I Make A Backdoor Roth IRA Contribution? | Hawaii Retirement Show 20.01.2025

In this Episode of the HI Retirement Show, Jason discusses the Backdoor Roth IRA. Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

Bonus Ep: Temporary Hazard Pay, State of Hawaii Employee Retirement System | Hawaii Retirement Show 15.01.2025

In this Episode of the HI Retirement Show, Jason briefly talks through some things to consider regarding the State of Hawaii - Employees Retirement System recent Temporary Hazard Pay.   Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

What Issues Should I Consider When Reviewing My Beneficiaries? | Hawaii Retirement Show 11.01.2025

In this Episode of the HI Retirement Show, Jason breaks down the Backdoor Roth IRA.   Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

Should I Contribute To My Roth IRA vs. My Traditional IRA? | Hawaii Retirement Show 05.01.2025

In this Episode of the HI Retirement Show, Jason breaks down some considerations when deciding between Roth and Traditional contributions. Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

Will A Distribution From My Roth IRA Be Tax & Penalty Free? 31.12.2024

In this Episode of the HI Retirement Show, Jason briefly breaks down how to determine if a distribution from a retirement account will be tax and penalty free.   Website: https://www.hiretirementshow.com LinkedIn: https://www.linkedin.com/company/hiretirementshow Email Us: aloha@hiretirementshow.com

Will A Distribution From My Traditional IRA Be Penalty-Free? 10.12.2024

In this Episode of the HI Retirement Show, Jason discusses the 10% penalty on Traditional IRA distributions and some of the exceptions to the penalty.   Website: https://www.hiretirementshow.com LinkedIn: https://www.linkedin.com/company/hiretirementshow Email Us: aloha@hiretirementshow.com

What Issues Should I Consider For My Aging Parents? | Hawaii Retirement Show 05.12.2024

In this Episode of the HI Retirement Show, Jason various issues to consider as it relates to aging parents.  This includes issues related to cash flow & living arrangements, estate planning, insurance, tax planning, assets & debts, and more.  Website: https://www.hiretirementshow.com LinkedIn: https://www.linkedin.com/company/hiretirementshow Email Us: aloha@hiretirementshow.com

Can I Contribute To A Roth IRA? 01.12.2024

In this Episode of the HI Retirement Show, Jason discusses how to determine whether or not someone can contribute to a Roth IRA.    Website: https://www.hiretirementshow.com LinkedIn: https://www.linkedin.com/company/hiretirementshow Email Us: aloha@hiretirementshow.com

Inflation Adjustment to E.R.S & FERS Pensions 27.11.2024

In this Episode of the HI Retirement Show, Jason breaks down the inflation adjustments to the State of Hawaii Employees Retirement System Pension as well as the Federal Employees Retirement System Pension.   Website: https://www.hiretirementshow.com LinkedIn: https://www.linkedin.com/company/hiretirementshow Email Us: aloha@hiretirementshow.com

SEP-IRA vs Solo401(k) 22.11.2024

In this Episode of the HI Retirement Show, Jason breaks down the similiarities and differences between the SEP-IRA and the Solo401(k).   Website: https://www.hiretirementshow.com LinkedIn: https://www.linkedin.com/company/hiretirementshow Email Us: aloha@hiretirementshow.com

Can I Make A Deductible IRA Contribution? 21.11.2024

In this Episode of the HI Retirement Show, Jason discusses the questions you need to ask to determine whether or not you can make a deductible IRA contribution or not.   Website: https://www.hiretirementshow.com LinkedIn: https://www.linkedin.com/company/hiretirementshow Email Us: aloha@hiretirementshow.com

Focusing on the Burn vs the Earn 14.11.2024

In this Episode of the HI Retirement Show, Jason discusses the importance of not always focusing or chasing down more earnings and instead periodically checking back in on your burn (spending) to effectively better your overall financial position.  Website: https://www.hiretirementshow.com LinkedIn: https://www.linkedin.com/company/hiretirementshow Email Us: aloha@hiretirementshow.com

Vegas Baby! The taxation of gambling winnings. 06.11.2024

In this Episode of the HI Retirement Show, Jason discusses the taxation of gambling winnings.  This includes the reporting requirements of gambling winnings as income, regular gambling withholdings, and deductions for gambling losses.  Website: https://www.hiretirementshow.com LinkedIn: https://www.linkedin.com/company/hiretirementshow Email Us: aloha@hiretirementshow.com

FERS Unused Sick Leave 25.10.2024

In this Episode of the HI Retirement Show, Jason discusses how unused sick leave is calculated and factored in to your years of service.   Website: https://www.hiretirementshow.com LinkedIn: https://www.linkedin.com/company/hiretirementshow Email Us: aloha@hiretirementshow.com

Common Financial Professional Licenses and Certifications 23.10.2024

In this Episode of the HI Retirement Show, Jason discusses the most common financial professional licenses and certifications.   Website: https://www.hiretirementshow.com LinkedIn: https://www.linkedin.com/company/hiretirementshow Email Us: aloha@hiretirementshow.com

The Four Factors Impacting Your Credit Score 19.10.2024

In this Episode of the HI Retirement Show, Jason discusses the four main factors that impact your credit score.   Website: https://www.hiretirementshow.com LinkedIn: https://www.linkedin.com/company/hiretirementshow Email Us: aloha@hiretirementshow.com

Qualified Charitable Distributions 11.10.2024

In this Episode of the HI Retirement Show, Jason breaks down the basics of Qualified Charitable Distributions.    Website: https://www.hiretirementshow.com LinkedIn: https://www.linkedin.com/company/hiretirementshow Email Us: aloha@hiretirementshow.com

All About RMDs - Required Minimum Distributions | Hawaii Retirement Show 04.10.2024

In this Episode of the HI Retirement Show, Jason breaks down Required Minimum Distributions.  He discusses what they are, when they need to be taken, how they are calculated, and more.  Website: https://www.hiretirementshow.com LinkedIn: https://www.linkedin.com/company/hiretirementshow Email Us: aloha@hiretirementshow.com

The Emergency Fund 28.09.2024

In this Episode of the HI Retirement Show, Jason shares his perspective on having an emergency fund.    Website: https://www.hiretirementshow.com LinkedIn: https://www.linkedin.com/company/hiretirementshow Email Us: aloha@hiretirementshow.com

First Principles Perspective on Life Insurance and Annuities 21.09.2024

In this Episode of the HI Retirement Show, Jason briefly breaks down Life Insurance and Annuities to their most basic and fundamental purpose.   Website: https://www.hiretirementshow.com LinkedIn: https://www.linkedin.com/company/hiretirementshow Email Us: aloha@hiretirementshow.com

FERS Survivor Annuity Elections | Hawaii Retirement Show 09.02.2024

In this Episode of the HI Retirement Show, Jason and Paul breakdown the different Survivor Annuity Elections for the FERS pension benefit.   This includes the Maximum Survivor Annuity, the Partial Survivor Annuity, the No Survivor Annuity, and a few others.   Website:  www.hiretirementshow.com LinkedIn:  https://www.linkedin.com/company/hiretirementshow Email Us: aloha@hiretirementshow.com

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