legacy

Selling a business is rarely as simple as agreeing on a number, signing a contract and depositing a check.

The number at the top of the offer is not necessarily the amount you will keep. Taxes, debt, transaction structure, seller financing and other obligations can significantly change the outcome. By the time an offer arrives, many of the strategies that could have improved that outcome may no longer be available.

That was the focus of a recent Ask the CFO conversation with Chris Clepp, found…

One of the patterns I see most often in growing businesses is not a lack of effort or intelligence. Most owners are working hard and carrying a tremendous amount of responsibility well.

Where businesses tend to lose momentum is in the accumulation of unresolved decisions.

A pricing adjustment gets delayed because leadership is concerned about customer reaction. A key hire stays open too long because nobody feels fully confident in the timing. Operational inefficiencies become accepted because …

When preparing for a business transition—whether passing it to a family member, selling to an external buyer, or stepping back from daily operations—certain risks can significantly impact the process. Two of the biggest challenges business owners face are customer concentration and management team readiness. These factors can affect business valuation, buyer interest, and long-term stability after the transition. Addressing these early can make the difference between a smooth transition and one …

Passing your business to the next generation is a major milestone—one that requires careful planning, strategy, and open communication. While the idea of keeping a business in the family is appealing, the reality is that many family-owned businesses don’t survive the transition. In fact, only 1 in 3 make it from the first to the second generation, and just 1 in 8make it to the third.

As a CFO with over 30 years of experience, I specialize in helping business owners navigate these transitions—av…

Every owner eventually asks the same question: What happens when I’m not here?

It doesn’t always come from wanting to retire. Sometimes it comes after a long week, a health scare, or just the realization that time moves faster than you thought.

The truth is, most small and family business owners wait too long to figure it out. Then, when the time comes, they have limited options and a lot of pressure.

Let’s talk about what those options actually look like — and how to start planning earl…

If you own a small or family-run business, there’s a good chance your fingerprints are on just about everything.
You know every customer, every supplier, every number in QuickBooks. You’ve spent years building this thing — and let’s be honest, it works because you work.

That’s exactly why thinking about stepping back, selling, or even taking a long vacation feels impossible.
It’s not that you don’t want to step away. It’s that you can’t quite imagine what would happen if you did.

But here’s what…

Reflections from the October Ask the CFO Session

In our October Ask the CFO session, I decided to take a break from the usual financial headlines — tariffs, cost-cutting, and global uncertainty — and focus on something closer to home: the human side of being a CFO in a family-owned or privately held business.

After all, numbers are the easy part. It’s people, relationships, and trust that make the work meaningful — and often, challenging.

The Six Cornerstones of a Great CFO (Fractional or Ful…