What really happens when you owe the IRS—and how much of it is actually fixable?

In this episode of Sterling Insights, Tracy McCary sits down with Michael Raanan, Enrolled Agent and President of Landmark Tax Group. Together, they explore IRS back taxes and tax resolution, sharing valuable insights and practical tips for listeners. Michael draws from his experience as a former IRS revenue officer to discuss how tax debt is calculated, resolved, and sometimes reduced, offering actionable advice for individuals and business owners dealing with IRS issues. This episode is a must-listen for taxpayers, advisors, and anyone concerned about IRS debt, providing both knowledge and tools to navigate this important subject.

Key Takeaways:

● Not All Tax Debt Is Accurate: Many IRS balances are overstated due to substitute returns—fixing filings can significantly reduce what’s owed.

● Cause, Cure, Compliance Framework: Understanding why the debt happened, how to resolve it, and how to stay compliant is key to long-term success.

● Multiple Resolution Options Exist: Payment plans, hardship status, and offers in compromise depend on financial analysis—not negotiation.

● IRS Mistakes Happen: Even large payments can be misapplied, leading to major penalties and long disputes.

● Beware of Tax Relief Scams: Many firms overpromise “pennies on the dollar” but fail to deliver real results.

Quotes from Michael Raanan:

● “It’s not that big of a deal when you owe back taxes—you just have to address it.”

● “The IRS is very black and white. It’s about what you qualify for, not negotiation.”

● “We hear it all the time—‘they didn’t do anything for me’—that’s the reality with a lot of these tax relief firms.”

Understanding how the IRS actually works—and what options truly exist—can turn a stressful tax problem into a manageable plan forward.

Connect with Michael:

Website: https://landmarktaxgroup.com/

What if your CPA could do far more than file taxes—and actually help you build wealth, avoid costly mistakes, and align your finances with your life goals?

In this episode of Sterling Insights, Mike Agol sits down with Jon Czerwinski, CPA and Managing Partner, a strategic tax advisor specializing in entrepreneurs, investors, and high-growth businesses. Together, they explore the evolving role of CPAs as strategic partners in business growth, sharing valuable insights and practical tips for listeners. Jon draws from his extensive experience to discuss common misconceptions about CPAs, the importance of proactive tax planning, and how business owners can better align their financial strategies with long-term goals, offering actionable advice for entrepreneurs, business owners, and high-income professionals. This episode is a must-listen for anyone looking to move beyond basic tax preparation and leverage financial strategy for growth, providing both knowledge and tools to navigate this important subject.

Key Takeaways:

● CPAs Are Strategic Advisors—Not Just Tax Preparers:

Many people misunderstand the role of a CPA. The real value lies in strategic planning, not just filling out forms.

● Annual Tax Planning Is the Minimum Standard:

Business owners should meet with their CPA at least once a year—ideally before year-end—to proactively reduce tax liability and adjust strategy.

● Your Tax Plan Must Align With Your Life Goals:

Whether your goal is lifestyle, monetization, or legacy, your financial strategy should reflect and support that vision.

● Ideal Clients Are Growth-Oriented and Engaged:

Entrepreneurs, strategic investors, side hustlers, and startups benefit most when they actively engage in the planning process.

● AI Is an Opportunity—Not a Replacement:

While AI can enhance efficiency, it cannot replace the strategic insight and personalized guidance of a skilled CPA.

Quotes from Jon Czerwinski:

● “If the only thing your CPA does is fill out a form, you don’t have a CPA.”

● “You hire a CPA for what’s between their ears—not the tax return they produce.”

● “Your life goals and your tax plan have to be in sync—otherwise, you’re working against yourself.”

The most successful business owners don’t treat their CPA as a once-a-year necessity—they treat them as a year-round strategic partner who helps guide smarter decisions, minimize risk, and maximize long-term success.

Connect with Jon:

Website - https://www.jccpas.com/

Instagram - https://instagram.com/jccpas/

LinkedIn - https://linkedin.com/company/jccpas/about/

Facebook - https://www.facebook.com/profile.php?id=61561069991961

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.