Category: Crewe Capital

Selling a privately held business is one of the most consequential financial decisions an owner can make. The process involved in preparing a business exit is a complex, multidimensional event that simultaneously affects valuation, tax strategy, legal structure, continuity, personal wealth, operational continuity, and interfamily dynamics. Yet many owners enter the process with insufficient advisory, potentially sacrificing significant value, taking on avoidable risks, and increasing the likelihood of not reaching a successful close.

In preparing for a business sale, owners almost always focus on one determining metric: the valuation multiple. This instinct is natural, as it is the figure that dictates the outcome of years or decades of work, but the multiple is ultimately an output that results from a key decision.

When business owners prepare to sell their company or bring on a new equity partner, the conversation naturally gravitates toward multiples, deal structure, and purchase price adjustments. While these are important, one factor that can be underexamined until it creates problems is organizational culture.

When owners begin to contemplate a sale, the instinct can be to only focus on getting the highest price. That instinct is understandable, but it misses how value is actually created in a transaction.

Artificial intelligence is one of the most talked-about topics in business today, and also one of the most misunderstood. Many small- to medium-sized business owners assume the applications belong to Silicon Valley, large corporations, or companies with deep technology budgets.

The reality is that AI tools are more accessible, more affordable, and more immediately useful than most middle-market owners realize. The businesses adopting them now aren’t necessarily the biggest or the most sophisticated. They’re the ones willing to experiment and apply the tools sensibly. The goal isn’t to replace your team or overhaul your business model. It’s to do what you already do, better.

Business owners who are considering selling their company and have charitable intentions can implement a few strategies to make the transaction tax efficient. One strategy often overlooked is donating shares of the company to charity before the sale.

Selling a business can move quickly once buyers lean in. Momentum is easiest to keep when information is easy to find and easy to trust. A well-organized data room, which is a secure online folder where sellers share key documents with potential buyers, does more than respond to diligence requests, which are detailed follow up questions buyers ask as they evaluate the business.

Most business owners only encounter Hart-Scott-Rodino (HSR) after a transaction is already underway—when timing pressure is highest and surprises are most costly. In this article, we discuss the process and implications of the HSR Act on business transactions.