When most people think of tax advisors, they picture corporate boardrooms and billion-dollar companies. But that idea is not only outdated—it’s costly. This common tax advisor myth leads many small business owners to miss out on savings, strategies, and long-term wealth.

A cost segregation study is a tax-saving strategy that allows commercial property owners to reclassify parts of their building into shorter depreciation schedules. Instead of depreciating everything over 27.5 or 39 years, a study identifies components—like lighting, flooring, and landscaping—that can be depreciated over 5, 7, or 15 years.

Before hiring a tax advisor, ask questions that reveal their experience with small business tax strategy, not just basic preparation. Look for someone who offers year-round planning, not just annual filing. Your advisor should help you save money, reduce risk, and make smarter business decisions—not just fill out forms.

If your business is generating consistent net income over $40,000–$60,000 and you’re paying self-employment tax as a sole proprietor or LLC, then yes, it’s likely time to consider filing an S Corp election. But timing matters, and you must meet IRS deadlines to get the full benefit this tax year.

Choosing the right business entity structure is one of the most important tax decisions you’ll make. Your entity structure doesn’t just affect legal liability — it also determines how your business income is taxed, what deductions you’re eligible for, how you pay yourself, and how much you’ll owe in taxes. Make the wrong choice, and you could end up paying thousands more than necessary.

No business owner wants to get audited. While most audits are resolved without penalty, the process can be expensive, time-consuming, and stressful. Worse, audits often uncover unrelated issues that can lead to fines or back taxes. The good news? Most audits are triggered by preventable mistakes or red flags. With the right strategy, you can significantly reduce your risk of being audited.

If you're a real estate investor, tax strategy isn't optional—it’s a critical part of maximizing your returns. From depreciation to 1031 exchanges, real estate tax planning offers powerful tools to legally reduce your tax burden and improve cash flow. Without a smart plan, investors often miss out on deductions worth thousands of dollars annually.

If you're a self-employed business owner or sole proprietor, choosing the right retirement plan can double as a powerful tax shelter. Two of the most popular options are the SEP IRA and the Solo 401(k). Both offer significant tax-deferred savings opportunities, but they have very different rules, benefits, and administrative requirements.

If you own multiple businesses or assets—or plan to—the way you structure ownership can dramatically impact your tax liability, legal exposure, and growth flexibility. One of the smartest (but least understood) tools is a holding company structure. A holding company owns other companies (subsidiaries) but doesn’t typically run operations itself. Instead, it serves as a parent entity that offers legal separation between businesses and can unlock powerful tax advantages.

Running a small business is rewarding, but it also comes with costs. The good news? Many of those expenses can be deducted to reduce your taxable income. Understanding these small business write offs not only saves money but also helps you reinvest in growth. Here are 10 of the most valuable tax deductions every small business owner should know.

The R&D Tax Credit (Research and Development Tax Credit) is a federal tax incentive designed to reward businesses for investing in innovation, process improvement, and new product development. Despite the name, you don’t have to be a high-tech lab or research facility to qualify. If your company is solving technical problems or improving how things are made or delivered, you may be eligible.

Many business owners believe: “If a buyer needs financing or asks for a seller note, it means they can’t afford my business—or worse, that the deal isn’t safe.”

Your business exit won’t happen by accident. Without a clear exit timeline, you risk leaving money on the table, rushing decisions, or missing personal goals like retirement or family succession. According to Inc., most owners underestimate how long it takes to prepare for a successful exit—often three to five years or more.

Exiting a business isn’t just about finding a buyer—it’s about knowing when to sell. Exit timing can significantly influence valuation, deal terms, and your personal financial security. If you wait too long, you risk declining market interest. Exit too early, and you may leave growth potential—and cash—on the table. Strategic timing means aligning your exit with business cycles and market readiness so you can walk away with maximum value.

Discover how to time your exit for maximum value. Learn when the market is ready, and your business is at peak value.

Most small business owners don’t think about leaving their business—until they’re forced to. Whether due to health issues, burnout, or a surprise opportunity, lack of planning often leads to regret, lost value, and rushed decisions. An exit timeline isn’t just about picking a retirement date. It’s about designing your exit around when you want to leave and how you want to feel when you do.

Explore the Mental Readiness Index to gauge your emotional preparedness for a business exit. Discover how mental readiness ensures a smooth transition.

Discover what happens after a business sale. Learn how to navigate life post-business sale with our expert insights and planning strategies.

Many small business owners believe exit planning is something only corporations or large firms need to worry about. This is one of the most damaging myths in small business ownership.

Most small business owners put off exit planning for one simple reason: they’re too busy running the business. But here’s the hard truth: if you don’t make time for exit planning now, you may not have the luxury of choosing when—or how—you leave later.