Solving IRS Challenges and Building Smarter Tax Strategies

Taxes are unavoidable, but how you plan for them, and how you handle challenges with the IRS, can make or break a business.

In this episode, I sat down with Mike Dunlap, a Texas CPA with 40+ years of experience in taxation, IRS resolution, and small business consulting. From helping clients negotiate with the IRS to guiding business owners on structure and strategy, Mike has seen it all.

If you want the full conversation, including stories we couldn’t fit here, you can watch the video below.

Why Tax Resolution Work Changes Lives

Every tax problem has a story. It’s often a mix of business setbacks, family struggles, or sudden hardships. Mike’s work is about helping people recover from those moments.

From penalties to fresh starts

Tax resolution isn’t about fighting the IRS. Instead, it’s about ensuring what the agency is trying to collect is correct and fair. Sometimes that means negotiating an installment plan so a business can pay over time. Other times, it’s securing a penalty abatement to reduce the financial hit. In the most extreme cases, it might mean an “offer in compromise,” where the IRS accepts far less than the full balance owed.

A real-world example

One example Mike shared: A client owed $300,000 after losing his business and going through a divorce. Mike was able to settle the case for $30,000 and give the client a second chance (instead of a lifetime of debt).

How did he do it? Well in the case, the client was in "dire straits" and to qualify for the offer, Mike had to go through an "exhaustive mini page schedule" to prove the client's financial situation (including his assets, liabilities, and cash flow). By demonstrating the client's inability to pay the full amount, Mike was able to negotiate the settlement down to just $30,000.

Programs You Might Not Know About

The IRS can feel intimidating, but there are relief options that most business owners don’t even realize exist. Mike shared a few that are worth knowing.

• First-Time Abatement: If it’s your first penalty, the IRS may take it off your record. Mike notes that you can usually get this abatement once, but after that, you must stay on track.
• Installment Agreements: A way to spread payments out over time instead of facing one giant bill.
• Offers in Compromise: Harder to qualify for, but for people in real hardship, this can cut the total owed down significantly.

Trends To Keep On Your Radar

Even if you’re up to date on taxes, tomorrow’s landscape is always shifting. There are a few big-picture changes business leaders should keep on their radar.

Upcoming tax law changes

Potential legislation in 2025 or 2026 could affect deductions, depreciation, and overall tax planning. Preparing early matters.

AI in business

Technology adoption in general is key. Businesses that avoid modern systems often end up struggling later. The opportunity is huge with tools like ChatGPT, but using AI responsibly and checking your information is crucial.

Common Mistakes That Cost Owners

Mike has worked with businesses of all sizes, and the same mistakes show up again and again.

Picking the wrong structure

While an LLC is a great legal structure, the mistake is not choosing the right way to be taxed. An LLC can be taxed in four different ways: A sole proprietor, partnership, C-corp, or an S-corp. Choosing the wrong one can add unnecessary costs.

Cutting back at the wrong time

Owners often cut marketing or delay hiring when things feel tight. In reality, those are the moments you need to keep momentum going.

Relying on spreadsheets

Some businesses currently rely on spreadsheets or the back of a napkin to manage their finances. They truly need a program, such as QuickBooks or Gusto, to help them track expenses, reconcile bank accounts, and maintain accurate records.

Not saving for taxes

One of the biggest traps. Spending cash as it comes in feels fine until the tax bill arrives.

Why a Strong Advisor Team Matters

Mike believes no one should run a business alone. The most successful owners surround themselves with a CPA, an attorney, a fractional CFO, a wealth advisor, and an insurance professional. Each advisor brings a unique perspective, and together they help leaders make confident decisions about hiring, expansion, and investment.

When those advisors collaborate, strategy stays aligned — and owners don’t get pulled in conflicting directions.

Key Takeaways for Business Leaders

The conversation offered clear lessons for any business leader:

• Proactive tax planning is a financial necessity. It helps you avoid penalties and save money in the long run.
• The right business structure and accounting system are foundational. They provide the clarity and stability needed for strategic growth.
• Embrace technology like AI, but be smart about it. It can be a powerful tool for marketing and research, but always verify information and use it to solve a specific business problem.
• Build a team of trusted advisors. Your CPA, attorney, and fractional CFO are not just service providers. They are a network of specialists who can help you solve complex problems and accelerate your business growth.

If you want a strategic financial partner who brings connections to vetted specialists like Mike, Bender CFO Services is here to help.

Book your consultation today and see how the right financial leadership, backed by a network of experts, can accelerate your business growth!