Sunday, September 28, 2025

The Crucial Question to Ask Before Selling: Is It Worth a Million Dollars?

Challenges and Considerations in Selling a Business: Insights from Richard Hamlin

Knowing when to sell a business can be a daunting decision for many owners, as highlighted by Richard Hamlin, executive vice president of The Reserve Group. Speaking at the Cleveland Smart Business Dealmakers Conference, Hamlin emphasized the challenges of determining the optimal time to sell, considering both market conditions and the state of the company.

Hamlin pointed out the dilemma faced by many owners – whether to sell at the peak and risk leaving potential returns on the table, or hold on too long and miss the window of opportunity. He stressed the importance of considering personal circumstances, such as the ability to weather economic downturns and the patience to wait for the right moment.

Drawing from his own experience with a company in the oil and gas industry during the 2007 financial crisis, Hamlin highlighted the consequences of missing the selling window. Despite receiving promising offers at the time, the market softened, and the business never reached the valuation suggested back then.

Emotions can also play a significant role in deal-making, with excitement, anxiety, and frustration potentially clouding judgment. Hamlin advised against letting emotions drive decisions, suggesting the involvement of a board of advisers to provide a dispassionate perspective.

Furthermore, Hamlin stressed the importance of including key stakeholders in the planning process early on, incentivizing them to be part of the deal and painting a clear vision of the benefits for them. By involving the CEO and management team in the decision-making process, owners can ensure a smoother transition and maximize the chances of a successful deal.

In conclusion, Hamlin emphasized the need for thorough research, understanding market conditions, and making decisions based on what is best for the individual owner. While timing the market can be challenging, seeking advice from trusted advisers and involving key stakeholders early on can help navigate the complexities of selling a business effectively.

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