About this episode

This episode discusses proactive tax planning strategies for business owners and retirees with CPA Dana Lashbaugh.

Are you leaving money on the table because of poor tax planning — or worse, setting yourself up for an unexpected Medicare or IRS surprise? In this episode of  Sterling Insights , Tracy McCary sits down with  Dana Lashbaugh, CPA and Owner of The CPA Group , a tax strategist specializing in business owners earning between $2M–$20M in revenue. Together, they explore proactive tax planning for business owners and retirees, sharing valuable insights and practical strategies that go far beyond basic tax preparation. Dana draws from his extensive experience in public accounting and as a former controller to discuss Roth conversions, IRMAA planning, 1099 estimated tax mistakes, succession planning, and smart exit strategies—offering actionable advice for business owners, independent contractors, and retirees. This episode is a must-listen for entrepreneurs, construction and restaurant owners, and high-income professionals who want to reduce taxes, avoid costly surprises, and build a smarter long-term financial strategy. Key Takeaways: ●  Proactive Tax Planning Beats Reactive Tax Filing:  Tax preparation is compliance — tax planning is strategy. Business owners who…

People in this episode

Host: Tracy McCary

Guest: Dana Lashbaugh

Topics covered

• tax planning
• business strategy
• financial advice
• retirement planning
• tax liability reduction
• Roth conversions

Keywords

• tax planning
• business owners
• Roth conversions
• Medicare
• IRS
• financial strategy
• tax liability
• retirement

Mentioned in this episode

Organizations: The CPA Group, Medicare, IRS

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