Tag: Roth Conversions
Roth Conversions for High Earners: Timing, Taxes, and Long-Term Control (Ep. 23)

Roth Conversions for High Earners: Timing, Taxes, and Long-Term Control (Ep. 23)

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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.

Key takeaways:

  • How Roth conversions can affect heirs, estate plans, and long-term family tax outcomes over multiple generations
  • Why higher income does not automatically rule out conversions, and how added income can trigger hidden taxes
  • How market downturns may lower the taxable cost of converting retirement assets
  • Why early retirement gap years can create valuable planning windows before Social Security begins
  • How moving between low-tax and high-tax states can change the timing and value of conversions
  • And more!

Resources:

Connect with Dan Reese CFP®:

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The Risk of Following TikTok Finance (Ep. 21)

The Risk of Following TikTok Finance (Ep. 21)

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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.

What to expect:

  • How social algorithms can pull you into financial advice content
  • Possible motivations behind influencer content
  • What fiduciary standards require (and what they do not)
  • How personalized planning can help you assess decisions and potential tradeoffs
  • And more!

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

Resources:

Connect with Dan Reese CFP®:

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The $150,000 Gift That Derailed Their Retirement with Brent Oliver (Ep. 19)

The $150,000 Gift That Derailed Their Retirement with Brent Oliver (Ep. 19)

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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.

Here’s what to expect:

  • Why starting strong doesn’t always mean finishing strong in retirement
  • How a single decision can derail your entire income plan
  • The hidden dangers of IRMAA and tax bracket creep
  • How to rebuild confidence with structure, buckets, and stress testing
  • And more!

Resources:

Connect with Dan Reese CFP®:

Connect with Brent Oliver: 

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:

  • Develop and implement a comprehensive wealth management plan to help them reach their financial dreams.
  • Make smarter decision in today’s uncertain political, economic and social environment.
  • Obtain an independent second opinion from a top financial advisor in their community.

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.

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