The Show

Brian Wiley is joined by business coach and author Allison Dunn for a conversation about why critical thinking is one of the most valuable financial skills an investor, business owner, or retiree can develop. They discuss how better decision-making applies to retirement planning, leadership, investing, and navigating life's biggest financial choices.

The show also answers listener questions on retirement planning, including how to coordinate 401(k)s, Traditional IRAs, HSAs, and Roth conversion strategies to improve tax efficiency. Brian explains why retirement accounts should be viewed both individually and as part of one comprehensive financial plan, while also discussing health insurance planning before Medicare eligibility.

Later, the conversation turns to long-term care planning, estate planning, trusts, and the pros and cons of self-funding versus insurance-based solutions. They also explore fiduciary advice, family communication around money, Micron stock and concentrated positions, investor psychology, and why having a thoughtful process often leads to better financial outcomes than simply reacting to markets or emotions.


Listen, Watch, Subscribe, Ask!
https://www.therealmoneypros.com

Guest:
Allison Dunn, Author and Business Coach
https://deliberatedirections.com/think-first-allison-dunn/
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Ataraxis PEO
https://ataraxispeo.com
 
Tree City Advisors of Apollon:
https://www.treecityadvisors.com
 
Apollon Wealth Management:
https://apollonwealthmanagement.com/
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00:00 Introduction & Think First with Allison Dunn
12:42 Smarter Financial Decisions: Roth Strategies, HSAs & Retirement Planning
34:55 Long-Term Care, Estate Planning & Family Conversations
59:58 Hour 2 Begins
01:01:15 Building Better Businesses & Stronger Leaders
01:28:40 Creating a Thinking Culture (Instead of Being the Bottleneck)
01:51:40 Investing Lessons from Micron's Massive Run
01:57:55 Closing Thoughts

Brian Wiley and Jeremiah Bates open the show with a discussion on concentrated stock positions, portfolio rebalancing, and the challenges investors face after large gains. Using examples ranging from Micron stock to broader market opportunities, they explore diversification, risk management, investor psychology, and the ongoing battle between fear and greed. The conversation also examines what it really means to be wealthy, how to think about financial independence, and why having a plan matters more than chasing the next investment opportunity.

The second hour focuses on retirement income planning and highly appreciated assets, particularly rental properties. They discuss capital gains concerns, 1031 exchanges, Delaware Statutory Trusts (DSTs), step-up in basis rules, and strategies for investors who want to simplify their lives without creating unnecessary tax consequences. They also cover Treasury bills, retirement withdrawal planning, income-focused investing, and how to evaluate whether your assets are positioned to support your long-term goals.


Listen, Watch, Subscribe, Ask!
https://www.therealmoneypros.com

Hosts:
Jeremiah Bates & Brian Wiley
—————
Ataraxis PEO
https://ataraxispeo.com
 
Tree City Advisors of Apollon:
https://www.treecityadvisors.com
 
Apollon Wealth Management:
https://apollonwealthmanagement.com/
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00:00 Introduction & Market Headlines
03:44 Concentrated Stock Positions & Rebalancing
16:52 Defining Wealth & Retirement Readiness
28:00 Fiduciary Advice & Financial Planning
35:44 Investor Psychology & Market Opportunities
01:03:05 Rental Property Strategies
01:15:18 Retirement Income Planning
01:33:55 1031 Exchanges & Tax Planning
01:49:30 Closing Thoughts

This material is for informational purposes only and should not be construed as tax, legal, or investment advice. Any examples presented are hypothetical and provided for illustrative purposes only. Qualified Opportunity Zone investments involve risks, including loss of principal, illiquidity, and legislative or regulatory changes that could affect anticipated tax benefits. Tax outcomes depend on individual circumstances, and there is no guarantee that any strategy will achieve its intended result. Investors should consult their tax, legal, and financial advisor before implementing any strategy.

SpaceX officially went public, raising a record $75 billion and becoming the largest IPO in history—and Jeremiah Bates and Nick Daniels spend the first hour breaking down what that means for investors, how IPOs work, whether buying newly public companies makes sense, and how many investors may gain exposure through index funds and retirement accounts.

The conversation then shifts to a major tax planning issue approaching at the end of 2026: Qualified Opportunity Zone (QOZ) investments. The guys explain why deferred gains from these investments are becoming taxable, the planning opportunities available before the deadline, and what investors should be doing now to prepare.

The show also covers donor-advised funds, highly appreciated stock strategies, the differences between flat-fee planning and traditional asset management, and practical retirement tax planning topics including required minimum distributions (RMDs), qualified charitable distributions (QCDs), Roth conversions, and Medicare-related planning opportunities.


Listen, Watch, Subscribe, Ask!
https://www.therealmoneypros.com

Hosts:
Jeremiah Bates & Nic Daniels
—————
Ataraxis PEO
https://ataraxispeo.com
 
Tree City Advisors of Apollon:
https://www.treecityadvisors.com
 
Apollon Wealth Management:
https://apollonwealthmanagement.com/
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