Managing Your Business

Dividend recapitalizations or “dividend recaps” are an increasingly common option for middle-market owners to take some chips off the table while maintaining a controlling position of the business.  But dividend recaps are not without risks. Whether you're considering one now or simply wanting to be prepared for the future, understanding how a dividend recap works can give you a serious advantage when the opportunity arises.

Imagine this: After years – maybe decades – of building your business, a buyer offers to take it off your hands. You feel relief, excitement … and maybe even a little pressure. The buyer sends you a document called a Letter of Intent (LOI). It looks straightforward. A few pages. A rough outline of the deal. You're tempted to skim, sign, and move on to the next phase.

As a CEO, you constantly balance the demands of growth, profitability and long-term strategy. Your business is not just an asset – it’s likely your life’s work, the result of years of dedication, risk-taking and strategic decision-making. Yet, even the most successful business leaders can benefit from a team of advisors who bring financial expertise, operational insight and strategic foresight to help maximize the company’s value and ensure a successful long-term outcome.

The Key Family Wealth BAS team is dedicated to providing guidance and support to privately held business owners like you. Specifically, the BAS team helps owners prepare for an eventual business transition with strategies and advice on how to maximize the after-tax value of a business transition.

Selling your business may not be on your immediate radar.  But in today’s volatile business landscape, it’s essential to understand the true value of your business. 

As the owner of a privately held business, you pour years of hard work, vision, and passion into growing your company. But what happens when an offer to buy arrives unexpectedly? Whether you’ve considered selling or not, the reality is that many business owners will face this moment at some point. The real question is: Will you be ready?

As the 250th anniversary of the American republic begins to loom less than two years away, citizens ask themselves again: What can I do this year to be “just as proud for half the money?” This article may not enable you to cut your tax bill in half, but it should provide you with key insights to discuss with your tax advisory team to help you keep more of what you make – in three different areas. 

This year business owners have had to contend with overall economic resiliency, cooling inflation, the Federal Reserve’s (Fed) pause in interest-rate hikes and the Fed’s decision in September to lower the rate by half a point . Geopolitical challenges remain as well. US politics is also an unknown.  As of this writing, we have upcoming presidential and congressional elections that could affect the expiration of the Donald Trump-era tax cuts that are set to expire at the end of 2025. But don’t let uncertainty paralyze your planning. Proactive planning is essential now.

As the end of 2025 approaches, owners of closely held businesses face a critical juncture in planning — not only for their own futures, but also for those of their families. The federal income tax and estate and gift tax cuts introduced in the 2017 Tax Cuts and Jobs Act (TCJA) are set to expire and revert to pre-2017 levels.

In the prior issue of this newsletter, we attempted to take the air out of the most common argument owners make for ignoring the planning necessary to successfully transition their companies: They believe that their businesses aren’t worth enough to meet their financial needs. “When it is,” they claim, “that’s when I’ll think about leaving.”

Like every owner, you will one day transition your business—voluntarily or involuntarily. On that day you will want to attain certain business and personal objectives: the first (and usually prerequisite to all others) is financial security. Believe it or not, most owners do absolutely nothing to consciously plan and systematically move toward that all-important goal.

The most significant factor that impacts a business owner’s ability to leave their company - successfully or not - is creating a company with transferable business value.