Blue Collar Wealth
Presented by Stone House®
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148. Preparing for Retirement After the 2025 Tax Bill — What the New Rules Mean for Your Next Chapter
In this episode of Blue Collar Wealth, hosts Bob Brown, Britt Doman, and Ben DeNault, CPA, discuss the significant tax changes that took effect in 2025 and how they may affect individuals preparing for retirement. The conversation focuses on how these changes may influence income planning, deductions, and timing decisions for retirees and near-retirees.
They walk through how the 2025 tax bill affects working individuals, retirees, and those transitioning out of full-time work, including changes to deductions, Social Security taxation, overtime income, and filing considerations for the year ahead.
➕ If you’re a business owner planning to exit your business within the next five years, pay special attention starting around minute 23, where the conversation shifts to tax considerations for business owners as they approach retirement — including structure, timing, and areas that may influence after-tax results depending on your situation.
This episode is designed to help you understand key concepts, think ahead, and prepare for decisions related to taxes and retirement.
Questions We Answer In This Episode (among many others!):
- What changed in the 2025 tax bill—and how could it affect your retirement planning?
- What are the most common tax filing mistakes people will make if they don’t plan ahead?
- What is the biggest misconception business owners have about selling or exiting their business?
- What tax and financial decisions should business owners make 3–5 years before exiting?
- Why do so many business owners regret selling—and how can you avoid that mistake?
Episode timestamps:
01:01 Understanding the 2025 Tax Bill
02:25 Impact on Business Owners
04:52 Tax Provisions for Working Individuals
06:36 Retirement Planning Insights
10:27 Common Tax Filing Mistakes
18:14 Business Exit Strategies
23:40 Tax Decisions for Business Owners Nearing Retirement
24:25 Structuring Your Business for a Sale
28:35 Financial Clean-Up and Value Drivers
37:51 Preparing for Life After the Sale
45:58 First Steps in Exit Planning
48:18 Key Takeaways and Final Thoughts
Disclosures: Stone House Investment Management, LLC is an SEC-registered investment adviser. Registration does not imply a certain level of skill or training. TBMA is an affiliated, separate tax firm— does not provide advisory services on behalf of SHIM. Informational only; not investment, tax, or legal advice. All investments involve risk, including possible loss. Scheduling a meeting does not create an advisory relationship.
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