Media
Podcast
The Long Game in Retirement
The Long Game in Retirement is hosted by financial advisor Jaime Cowper, who brings clarity, calm, and straight-talk to the topics that matter most: income planning, tax strategy, Social Security, market risk, and building a retirement that actually supports your life.
Listen on Apple Podcasts, Spotify, or YouTube.
Jaime Cowper is an investment advisor representative of Advisory Alpha, LLC, a SEC registered investment advisor. All opinions expressed by Jaime Cowper or any podcast guests are solely their own opinions and do not reflect the opinions of Advisory Alpha. This recording is for informational purposes only and should not be relied upon for investment decisions. Clients of Advisory Alpha may maintain positions in securities discussed in the program.
You might already be taking a GLP-1 medication, or it could be part of your future. What many people heading into retirement do not realize is that without the right Medicare coverage, a prescription like this can add $10,000 to $15,000 a year to healthcare costs, often for years at a time rather than as a one-time expense.
If you're in your 50s or early 60s and you've been putting off long term care insurance because of the cost, there's a new provision you should understand. Starting in 2026, a rule from the Secure 2.0 Act allows certain retirement plan holders to withdraw funds specifically for long term care premiums without the 10% early withdrawal penalty, even if you're under 59.5.
When RMD age arrives, most retirees assume they just have to pull money out and pay the tax. But without a strategy for which account to withdraw from, you could end up selling investments during a down market and locking in losses you didn't need to take.
The 2026 Social Security cost of living adjustment and the Medicare Part B premium increase do not move in the same direction, and for many retirees that gap shows up every January. Over a 20 or 30 year retirement, the structural mismatch between Social Security Cola and healthcare inflation can quietly erode buying power in ways most plans do not account for.
For many homeowners approaching retirement, an unexpected question starts to surface: do you stay, downsize, or tap into your equity? For many people approaching retirement, their house is worth more than every investment account they own combined. That makes this one of the most consequential financial decisions of the next chapter.
If you have been wondering what the Social Security trust fund headlines actually mean for your retirement, or whether the benefit you have been counting on will really be there, you are not alone. With full retirement age now officially reaching 67 for everyone born in 1960 or later, the questions around timing, claiming, and long-term planning are more relevant than ever.
In this episode, Jaime Cowper walks through a hypothetical side-by-side comparison showing how someone who saved $300 a month for just ten years starting at 22 ended up with more than someone who saved the same amount for 33 years starting at 32.
In this episode, Jaime Cowper breaks down how Medicare's income-related monthly adjustment amount is calculated, why its cliff structure can be triggered by just $1 over a threshold, and what the SSA-44 form can do for retirees whose income has changed.
You saved well, planned well, and now you're sitting on more than you're likely to spend in your own lifetime. But if you haven't thought carefully about how to share that wealth while you're still here to enjoy it, you could be missing one of the most rewarding opportunities in retirement planning.
You have spent decades building your retirement savings, but have you considered what happens to your IRA or 401K when your kids inherit it? Since the SECURE Act of 2019, non-spouse beneficiaries must withdraw the full balance within ten years, often during their peak earning years. That could push them into a higher tax bracket and send a significant portion of your legacy straight to the IRS. Jaime Cowper, a financial advisor with over 20 years of experience helping retirees plan with confidence, walks through exactly how the inherited IRA rules work now and explores a life insurance strategy that could help families pass wealth in a more tax efficient way. She shares a real client example where a couple used a survivorship policy to create $1 million in income tax free benefits for their four children. If you are thinking about retirement income planning, estate strategy, or how to protect your family's inheritance from unnecessary taxes, this episode was made for you.
Retirement planning is personal, yet so many people work with advisors who talk over their heads, rush through meetings, or never ask what matters most to them. If you've ever left a financial conversation feeling more confused than when you walked in, this episode will resonate. Jaime Cowper, a financial advisor, shares why the advisor-client relationship is just as important as the retirement strategy itself. She explains what draws people to advisors who prioritize listening and patience, shares real stories from clients who found clarity after feeling overlooked, and discusses her work mentoring more women into the financial planning space. This episode is for anyone approaching retirement who wants to feel truly understood by the person helping guide their financial future.
Cognitive decline in aging parents often shows up in their finances long before it shows up anywhere else, an unopened stack of mail, a bill paid twice, or new donations to organizations they have never supported. These are early warning signs financial advisors and families both need to recognize.