The CFO'S Perspective

Capital gains planning is more than a conversation about taxes. It’s about identity, family, legacy, tradeoffs and non-negotiables. It’s about guarding your pocketbook, but also protecting your heart.

The state of Washington’s decision to increase the capital gains tax in 2025 could force many business owners contemplating a sale to confront the deeply emotional, human questions tied up with their financial decisions. With a 9.9% state capital gains tax layered on top of federal taxes, a business owner’s total tax burden can exceed 30%. That’s often when owners realize navigating this alone could be a costly mistake. Your best bet at making the right decision is to surround yourself with the right experts. The ones who know it’s not just about the numbers, but what matters most to you.

We talked with four seasoned advisors, three tax attorneys and a CPA, who understand that behind every transaction is a person making a critical, once-in-a-lifetime, decision. They see their role as not simply technical but relational. They are guides, leading clients through the thickets, around the quicksand, and on to safer ground.

We recently covered the cost of tax compliance in this recent article.  The costs are a direct result of how companies face a myriad of tax compliance issues, even in the wake of tax reform that is supposed to boost bottom line results. The top ten federal tax compliance issues for businesses haven't changed much in the wake of this reform. These are:

We are continuing on the topic of tax compliance from the previous article.

If there is one thing most of us can agree on, it is that this nation's tax code is complicated! In 1955, the Internal Revenue Code was just 409,000 words, which already sounds daunting. By 2017, it had ballooned to nearly six times that size, clocking in at over 2.4 million words. According to the Tax Foundation, there are also roughly 60,000 pages of tax-related case law that are vital to understanding this nation's tax code.

The hardest thing in the world to understand is the income tax."
- Albert Einstein

Every business is required to file tax returns and make payments on income at the state and federal level. While each organization has its own requirements, ignorance of the rules is not an excuse for non-compliance.

Not only is it vital that a company dedicate resources to federal tax compliance, it is also costly. Since tax rules tend to change frequently, there is a high risk of mistakes as well as the potential to miss opportunities, both situations that could hurt your company's bottom line.

Make sure you pay your taxes; otherwise you can get in a lot of trouble."
- Richard Nixon