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 plan ahead can significantly reduce lifetime tax liability.

● Roth Conversions & IRMAA Awareness Matter in Retirement: Strategic Roth conversions can reduce required minimum distributions (RMDs) and prevent costly Medicare premium increases tied to income thresholds.

● 1099 Income Requires Quarterly Payments: Independent contractors must make estimated tax payments to avoid penalties and painful April surprises.

● Exit & Succession Planning Has Major Tax Implications: Selling, expanding, or transitioning a business requires careful asset allocation and coordination with advisors to minimize tax impact.

● Staffing Is the Biggest Challenge in Accounting Today: With hundreds of thousands of CPAs exiting the profession, access to responsive, relationship-driven advisory services is becoming increasingly valuable.

Quotes from Dana Lashbaugh:

● “We’re not just preparing tax returns — we’re helping clients plan where they’re going.”

● “There’s really no such thing as a quick tax question — because the right answer depends on the details.”

● “The pain is a lot easier quarterly than getting one big surprise bill on April 15th.”

Smart tax planning isn’t about being aggressive — it’s about being intentional. The earlier business owners and retirees plan, the more control they maintain over taxes, cash flow, and long-term wealth.