About this episode

The episode discusses the financial decisions business owners must consider regarding structure, exit planning, and investment strategies.

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…

People in this episode

Hosts: Brian Wiley, Jeremiah Bates

Topics covered

• business structure
• tax planning
• investment strategies
• exit planning
• portfolio risk
• listener questions

Keywords

• LLC
• S Corporation
• cost basis
• inherited assets
• concentrated stock
• Qualified Opportunity Zones
• fiduciary advice

Sponsors

Ataraxis PEO, Tree City Advisors of Apollon, Apollon Wealth Management

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