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 to provide specific advice or recommendations. Never make any investment or financial decisions based on information offered on this show without first consulting your financial, legal, or tax advisor. All economic and performance information mentioned on the show is historical in nature and is not indicative of any future results. All indices mentioned on

Hawaii Retirement Show is a education podcast hosted by Jason Cutitta, CFP®, with 100 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Jason Cutitta, CFP® hosts Hawaii Retirement Show, a education show with 100 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

• 

  Episode #119

  Ep.#119: Annuities - The Good, The Bad, and Where They Fit with Tracy Lownsberry

  Aug 12, 202659 min

  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: aloha@hiretirementshow.com

  ListenShow Notes
• 

  Episode #118

  Ep.#118: Planning Ahead for Senior Living in Hawaii with Tricia Medeiros of The Plaza Assisted Living

  Jul 22, 202640 min

  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 Email Us: aloha@hiretirementshow.com

  ListenShow Notes
• 

  Episode #117

  Ep.#117: Hawaii Real Estate in 2026 & Downsizing Tips with Maila Gibson-Bandmann

  Jul 15, 202622 min

  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 Email Us: aloha@hiretirementshow.com

  ListenShow Notes
• 

  Episode #116

  Ep.#116: Real Estate Tax Planning: Exclude up to $250k or $500k of Home Sale Gain with Andy Panko, CFP®

  Jun 30, 202648 min

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

  ListenShow Notes
• 

  Episode #115

  Ep.#115: Risk & Reward with Ben Carlson, Timeless Investing Lessons

  Jun 23, 202639 min

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

  ListenShow Notes

Based on semantic analysis of episode topics and host coverage, this show is a strong guest fit for executives in:

Industry fit is computed by PitchCentric using vector embeddings of the show's episode catalog.