Can AI Really Replace a Financial Advisor?

AI can generate a retirement strategy in seconds, but can it understand the emotions, relationships, and life decisions behind it? In this episode of The Modern Retirement Playbook, Jason Matthews explores the growing role of artificial intelligence in retirement planning and where its limitations …

Are You Making a Costly Social Security Mistake Without Knowing It?

Could the wrong Social Security strategy cost you more than you realize, even if your benefits never get cut? In this episode of The Modern Retirement Playbook, Jason Matthews breaks down some of the biggest misconceptions surrounding Social Security and retirement income. He explains how different…

Could Future Tax Changes Disrupt Your Retirement Plan?

What happens to your retirement plan when lawmakers decide to change the tax rules? In this episode of The Modern Retirement Playbook, Jason Matthews discusses California's proposed billionaire tax and uses it as a springboard for a bigger conversation: the uncertainty of future tax policy. Jason e…

Are You More Afraid of Running Out of Money or Living Too Long?

What's the bigger retirement risk: running out of money, or worrying that you might? In this episode of The Modern Retirement Playbook, Jason Matthews explores the concerns that keep many retirees up at night, from longevity risk and market volatility to the challenge of turning savings into reliab…

Can Billionaire Habits Reveal Smarter Retirement Strategies?

What do rented swans, air-conditioned lawns, and a dog with its own inheritance have to teach the rest of us about retirement? In this episode of The Modern Retirement Playbook, Jason Matthews explores the surprising financial lessons hidden behind some of the extravagant habits of the ultra-wealth…

Could One 401(k) Decision Impact Your Entire Retirement?

What should you actually do with your 401(k) when you retire and could the wrong move cost you more than you think? In this episode, Jason Matthews breaks down the key choices retirees face: leaving money in a 401(k), rolling it into an IRA, or cashing out. He explores the potential tax implication…

Are You Doing the Right Financial Moves at Every Stage of Life?

What should your finances look like at every decade of your life? In this episode, Jason Matthews walks through a decade-by-decade approach to building financial health, from your twenties to your seventies and beyond. The conversation highlights how early habits like saving and automation can shap…

Can You Still Afford the American Dream in Today’s Economy?

Is the American Dream still within reach or just getting more expensive? In this episode, Jason Matthews explores how rising costs, longer lifespans, and shifting financial responsibilities are reshaping what retirement looks like today. From the realities of multi-generational households to the gr…

A 2032 Countdown: What Happens If Social Security Falls Short?

Could a future cut to Social Security reshape your retirement income? With projections pointing to a 2032 shortfall and potential benefit reductions, this episode breaks down what it could mean for retirees and those planning ahead. Jason Matthews discusses how to prepare for uncertainty, including…

Is Your Money Working—or Just Sitting There?

Is your money quietly losing value even while it feels safe in the bank? In this episode of The Modern Retirement Playbook, Jason Matthews unpacks the concept of “dead money”—cash that isn’t working hard enough to keep up with inflation or taxes. Jason explores how too much idle savings can create …