Hawaii Retirement Show

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

In this episode of The Hawaii Retirement Show, Jason unpacks a major SECURE 2.0 change taking effect in 2026, the requirement that high-income earners make their catch-up contributions as Roth. He explains how the IRS’s final regulations define the wage threshold and what the update means for different plan sponsors. Jason breaks down how the mandate applies across various employer plans, the implications for employees whose plans don’t offer Roth contributions, and why its impact may vary from one participant to another. He also explores Roth in-plan conversions, detailing how they work, which funds are eligible, the tax considerations, and the strategic reasons many savers use conversions to build tax-free assets or reduce future RMD exposure. Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

In this episode of The Hawaii Retirement Show, Jason sits down with legendary big wave surfer Clark Abbey for an inspiring and wide-ranging conversation about life, legacy, and the ocean. Clark shares stories from growing up in a multi-generational surfing family in Hawai‘i, offering a window into the mindset and discipline it takes to ride some of the world’s most powerful waves. Clark talks about unforgettable sessions at Waimea Bay, the physical and mental preparation behind big wave surfing, and how Clark continues to stay in peak condition as he gets older. They also explore how canoe paddling brings people together, fostering both community and connection to the ocean. It’s a thoughtful and uplifting episode that celebrates passion, purpose, and the power of staying active and engaged—no matter your age or the size of the wave. Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

In this episode of the HI Retirement Show, Jason is joined by Seth Colby, PhD, Hawaii’s Chief Economist, for a wide-ranging conversation about the state’s economic landscape. They explore key data and trends shaping Hawaii’s future, from an aging population and high cost of living to questions of growth and long-term resilience. A thoughtful discussion for anyone interested in understanding the economic forces that impact life and retirement in Hawaii. Hawaii Economic Association: https://hawaiieconomicassociation.com Seth Colby Substack: https://substack.com/@sethcolby Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

In this episode of the HI Retirement Show, Jason tackles a critical issue for federal employees, miscalculating your FERS pension. With the recent federal shutdown top of mind, Jason opens with a quick check-in and a reminder that financial stress can be a great prompt to reassess your emergency savings. Then, he dives deep into how small errors in your FERS pension, like misunderstanding your High-3 salary, incorrect service time, or applying the wrong multiplier, can lead to big surprises in retirement. He also breaks down the often-misunderstood FERS Retirement Supplement, a temporary but valuable bridge to Social Security. Jason shares practical steps to verify your records and avoid costly mistakes, because you only retire once, and the details matter. Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com

In this episode of the HI Retirement Show, Jason explores the overlooked problem of saving too much for retirement. Jason breaks down why rigid savings rules and fear-based habits can lead to stress and difficulty spending later in life, and highlights the importance of balance, flexibility, and defining your own sense of “enough.” Website: https://www.hiretirementshow.com Email Us: aloha@hiretirementshow.com