Ramp Up to Retirement

Ramp Up to Retirement


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

November 12, 2025

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.