The Show

Retirement taxes are rarely as simple as people expect, and making the wrong withdrawal at the wrong time can have consequences far beyond your tax bill.

In our first hour, Jeremiah Bates and Alex Lundgren explain how IRA withdrawals, pensions, Social Security, brokerage accounts, Medicare IRMAA surcharges, and capital gains work together to shape your lifetime tax picture. They discuss why major purchases, home remodels, and other large withdrawals deserve careful planning to avoid unnecessary taxes and higher Medicare costs.

The conversation later shifts to Social Security planning. The hosts cover when to claim benefits, how working before full retirement age can affect payments, filing strategies for married couples, survivor benefits, and why Social Security should be coordinated with the rest of your retirement income plan instead of viewed in isolation.


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

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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 Welcome Back to The Real Money Pros
01:00 The Retirement Mindset Most People Miss
05:35 The Questions Every Retiree Eventually Asks
10:50 Why Investments Alone Aren't a Financial Plan
17:00 Should You Use Your IRA to Remodel Your Home?
23:45 The Hidden Cost of Large IRA Withdrawals
31:00 Is Social Security Really Going Bankrupt?
42:40 Can Working Reduce Your Social Security?
47:30 When Should You Actually Claim Social Security?
1:05:05 Spousal vs. Survivor Benefits (Big Difference)
1:10:40 How to Build a Retirement Plan That Actually Works

Whether you're starting a business, growing one, or preparing to exit, the financial decisions you make today can have long-term tax and estate planning consequences.

In Hour 1, Brian Wiley and Jeremiah Bates explain the differences between LLCs and S Corporations, when an S Corp election may make sense, how business structure affects taxes and liability, and why business owners should coordinate their entity planning with their estate plan. They also discuss cost basis, inherited assets, and avoiding costly mistakes before they happen.

Hour 2 shifts to investing, covering concentrated stock positions, strategies for managing highly appreciated investments like Micron, investor psychology, and ways to think through market volatility, geopolitical events, and portfolio risk without letting headlines dictate your decisions.

The final hour answers listener questions on business succession planning, selling a closely held business when family members don't want to take over, Qualified Opportunity Zones and the upcoming 2026 tax deadline, evaluating annuities within a comprehensive financial plan, and why fiduciary advice should focus on your entire financial picture—not just one investment account.


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

—————————————————————
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 Hour 1 – LLCs, S Corps & Smarter Business Planning

09:58 Cost Basis, Estate Planning & Inherited Assets

31:06 Concentrated Stock Positions & Risk Management

40:20 Iran, Oil Prices & Market Headlines

59:59 Hour 2 – Business Succession & Exit Planning

01:10:21 Qualified Opportunity Zones, Annuities & Retirement Planning

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/
—————
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