Your first profitable year in business is worth celebrating. But it can also bring expensive tax surprises, especially if you're still managing the business like you did when revenue was lower. Here are the most common mistakes new business owners make and what to do instead.

As home values rise, the federal home sale exclusion may no longer be enough to eliminate capital gains tax when a property is sold or inherited. The difference between a large tax bill and a smaller one can come down to how well a homeowner documented capital improvements over the years. Keeping a permanent record of qualifying expenses is one of the simplest steps homeowners can take to protect themselves.

The IRS just made it easier for families to fund Trump accounts without triggering an unexpected gift tax filing requirement. In Revenue Procedure 2026-25, the IRS established a safe harbor that allows qualifying donors to contribute cash to a child's Trump account and skip Form 709 entirely, as long as key conditions are met. Here's what you need to know before making contributions.

Most business owners rely on backward-looking financials that tell them where they have been, not where they are going. A cash flow forecast fills that gap by projecting future inflows and outflows, helping leaders spot problems early and make smarter decisions about hiring, investing, and financing. Updated consistently and tied to real business decisions, it shifts leadership from reactive to proactive.

Business owners who move money, goods, or services between commonly controlled entities are subject to IRS transfer pricing rules, which require that intercompany transactions be priced as if they were conducted between unrelated parties. When those prices are not set correctly, the IRS has authority under IRC Section 482 to reallocate income and assess back taxes, interest, and penalties that can reach 20% to 40% of the resulting underpayment. With the right documentation and a deliberate approach to pricing, most small and mid-size business owners can manage this exposure without complex or costly studies.

Most business owners carry a rough estimate of what their company is worth, but that mental number is not a valuation, and the gap between the two can be costly. A formal, methodology-based business valuation is required in a wide range of situations, including selling or transferring a business, estate planning, lending, divorce, equity compensation, and shareholder disputes. Working with a credentialed valuator and involving your CPA early ensures the resulting number is defensible when it matters most.

Selling a business, rental property, or other large asset triggers a range of tax consequences, including capital gains tax, depreciation recapture, and the net investment income tax, that can result in a significantly larger bill than most sellers anticipate. Tools like installment sale elections, deal structure adjustments, and strategic closing timing can reduce that exposure, but most of them require action before the transaction is finalized. A conversation with your CPA before you enter active negotiations is the most reliable way to protect your after-tax proceeds.

Nonprofits are disproportionately vulnerable to occupational fraud due to small administrative teams, part-time board oversight, and heavy reliance on cash-based transactions. Asset misappropriation schemes such as skimming, billing fraud, and expense reimbursement abuse are among the most common threats, and the typical scheme goes undetected for over a year. By implementing practical internal controls, strengthening board oversight, and engaging a CPA proactively, nonprofits can significantly reduce their exposure before a loss occurs.