Retirement tax decisions often feel simple on the surface, but the ripple effects can last decades. The real question is not whether taxes will be paid, but when, how, and by whom.

In this episode, Dan Reese, CFP®, walks through how Roth conversions, a taxable event, can fit into a broader retirement and estate plan for high-income earners. He explains when conversions may help manage future tax exposure, Medicare premiums, and inherited IRA issues. The conversation also covers market downturns, early retirement gap years, state tax differences, and why scenario planning is essential before acting.

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Most business owners say they feel prepared to step away, but available data suggests gaps in readiness.

In this episode, Dan Reese breaks down insights from the National State of Owner Readiness Report and explains common areas where small and mid-sized business owners may lack preparation for a significant financial transition. With a large portion of many owners’ net worth tied up in their business, exit planning often involves business, personal, and financial considerations.

Dan walks through common elements often associated with readiness, including understanding business value, identifying wealth gaps, and planning considerations for life after the business following a transaction.

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Online platforms surface a steady stream of financial content, often from influencers whose guidance is not tailored to individual situations.

In this episode of Ramp Up to Retirement, Dan Reese discusses the difference between broad online commentary and fiduciary planning, and how that gap can affect real retirement decisions. He walks through examples involving Roth conversions, Social Security timing, and investment choices that are sometimes framed too broadly in short-form content.

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Converting from a traditional IRA to a Roth IRA is a taxable event.

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Gold is in the headlines again. 

Prices are higher this year, we see gold ads on TV, and fear-based marketing may be convincing more retirees to convert their savings into precious metals. But is gold truly as safe as it’s perceived to be, or are investors falling for glitter over substance?

Dan Reese delivers a calm, factual look at the emotional and financial realities of gold investing. From physical bars to ETFs, Dan explains the pros, cons, and costly surprises many people overlook, especially when they’re acting out of fear.

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Mark and Susan thought they did everything right: no debt, over a million saved, markets trending up. But one well-intentioned gift to their kids set off a chain of financial consequences they didn’t anticipate.

In this episode, Dan Reese is joined by Brent Oliver for a hypothetical case study exploring how using the concept of a financial “postmortem”, an exercise in looking back to uncover what went wrong and why. You’ll hear how early retirement optimism, overconfidence, and lack of a coordinated plan may result in unexpected taxes, reduced income, and potential long-term challenges.

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About our Guest: 

Brent Oliver is a Wealth Manager at Avery Wealth, Inc. He focuses on providing wealth management solutions to retirees and pre-retirees in the Mid-Michigan Area. Brent helps affluent clients address their five biggest concerns: preserving their wealth, mitigating taxes, taking care of their heirs, ensuring their assets are not unjustly taken and charitable giving.

Brent has been with Avery Wealth, Inc. since 2013 where he uses a consultative process to gain a detailed understanding of his clients’ deepest values and goals. He then employs customized recommendations designed to address each client’s unique needs and goals beyond simply investments.

Successful individuals and families work with Brent to:

Previously, Brent owned and operated Midwest Wireless Communications, LLC, a successful business, in the Jackson Area. He hosts a weekly radio show/podcast, The Retirement Café, which focuses on educating listeners on a wide variety of financial planning and investing topics. He is currently a Trustee on the Western School Districts Board of Education.

Disclosure:

The scenarios discussed are hypothetical and for educational purposes only. They do not represent actual clients or guarantee future results. Investment involves risk, including possible loss of principal.

Did you know that even one extra dollar of income in retirement may trigger higher taxes, Medicare premiums, or health insurance costs?

This week, Dan Reese explains common retirement planning situations where a single extra dollar in income can unexpectedly spike your taxes, Medicare premiums, and insurance costs. From IRMAA surcharges to Social Security taxation rules to ACA subsidy limits, Dan explains how understanding these often overlooked thresholds can help retirees make more informed financial decisions.

He also walks through smart strategies to avoid them, like Roth conversions, withdrawal sequencing, and charitable giving tactics that can help protect your nest egg and optimize your income.

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Disclosure: Converting from a traditional IRA to a Roth IRA is a taxable event.

One of the biggest risks to your retirement may not be the market. It could be overconfidence.

Dan Reese examines the genuine risks of DIY financial planning, particularly in a world inundated with AI tools and financial influencers who oversimplify complex decisions. From emotional investing to overlooked tax landmines and Medicare surprises, Dan breaks down why retirement planning involves more than simply choosing investments.

You’ll learn how behavioral biases, sequence-of-return risk, and misunderstood withdrawal strategies may impact your financial future if overlooked.

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Most people think the hard part is saving for retirement, but the real challenge begins when the paychecks stop.

Dan Reese walks through the crucial mental and financial shift from accumulation to decumulation and why so many retirees get it wrong. From tax surprises and market volatility to emotional roadblocks and overlooked estate planning, Dan breaks down the common pitfalls and shares what it takes to create a truly sustainable income plan.

You’ll learn how to map out long-term tax liabilities, balance guaranteed vs. variable income, and build financial confidence in retirement.

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Retirement planning doesn’t exist in a vacuum, especially when tax laws are shifting. 

Dan Reese and guest Brent Oliver, Senior Wealth Advisor at Avery Wealth, break down the latest tax legislation and what it means for your future income, charitable giving, and estate plans.

From the extension of lower tax brackets to the expanded standard deduction and SALT cap increase, Dan and Brent cut through the noise to highlight some impactful changes for retirees and pre-retirees. They also explain how to leverage tax-smart strategies, like qualified charitable distributions, to help make the most of your retirement income.

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About our Guest: 

Brent Oliver is a Senior Wealth Advisor based in Jackson, Michigan, with 11 years of experience in the field. As a CERTIFIED FINANCIAL PLANNER professional and Senior Wealth Advisor, Brent helps families identify and work towards achieving their financial goals. His comprehensive approach to wealth management helps families identify where they are today, where they want to be, and what gaps might prevent them from achieving all that is important to them. He has the heart of a teacher and works with clients to ensure they understand why strategies are being employed and how they can help families reach their goals.

Many people feel confident about Social Security until it’s time to file. That’s when the conflicting advice from neighbors, social media, and self-proclaimed experts can make a complex decision even harder. 

In this episode, Dan Reese, CFP®, breaks down the most common Social Security myths and explains how decisions around claiming, spousal benefits, and timing can affect your broader retirement strategy.

Whether you’re married, divorced, or filing solo, Dan shares key considerations that may help you make a more informed decision and avoid unintended tax and income surprises later on.

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