Closing Remarks Q&A with Ben Wagner: When Should You Start Preparing to Sell Your Business?

Most business owners don’t wake up one day and decide to sell their company. The decision is usually years in the making.

In this episode of Closing Remarks, host Dara Shareef talks to Ben Wagner, Senior Director at Benchmark International, for a special Q&A focused on the questions business owners ask most often before going to market.

• Why waiting to sell may not always lead to a better outcome and how preparation can create more options
• Common misconceptions about private equity and the different paths available to business owners considering a future exit
• How buyers evaluate leadership teams, founder dependency, and the long-term durability of a business
• Why the best transaction is not always the highest offer and how business owners can balance value, legacy, and future opportunities

Based on daily discussions with business owners, Ben brings forward topics that frequently shape exit decisions:

• Should I sell now, or wait?
• What if my EBITDA improves in two or three years?
• How do I know if private equity is the right fit?
• What will happen to employees after the deal?
• And how can I prepare before I am ready to sell?

Together, Dara and Ben highlight the significance of preparation over timing, the need to build competitive interest among buyers, and the importance of building a business that can grow beyond its founder.

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Why Waiting Isn’t Always the Best Strategy

Many business owners believe their business will be worth more in two or three years. That idea is easy to grasp: grow EBITDA, improve performance, and enter the market from a stronger position.

But as Dara explains, this assumption can be risky, as no business operates in a vacuum. Economic shifts, industry changes, and unexpected challenges can alter even the strongest growth trajectory. Even a strong business can face outside forces that alter its trajectory.

This does not mean every owner should sell immediately. It means owners should not base their decision only on the idea that their business will be worth more later.

A Sale Does Not Have to Mean Walking Away

Another widespread misconception about selling a business is that it always means selling 100% and exiting completely. In reality, there are many different structures. A business owner can sell a majority stake, keep some equity, and stay involved in management or on the board. They can also partner with a buyer to speed up growth.

The key is understanding what options are available before assuming there is only one path 

Private Equity is Not One-Size-Fits-All

A significant takeaway from this episode is that private equity is not a one-size-fits-all approach. Some business owners feel unsure when they hear the words “private equity.” They may worry about losing control, harming the culture, or seeing changes they do not support. Dara acknowledges these concerns yet also explains that private equity is often misunderstood.

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The right private equity partner can bring capital, support, industry expertise, and access to expanded growth opportunities. Many are looking to support leadership teams and help accelerate their growth. 

Some owners may choose a complete exit. Others may retain equity, remain involved in the company, or partner with investors to accelerate growth.

That is why going to market with an open mind matters. Being aware of the different possible scenarios can help you make better-informed decisions about where to go next.  

Building a Business That Can Survive Without You

One of the most valuable lessons learned during this episode is the idea of durability. Buyers are not simply evaluating performance. They are looking at leadership, customer relationships, team strength, and the company’s ability to succeed long after the founder steps away.

Businesses with empowered leadership teams, distributed responsibilities, and a strong internal infrastructure are often better positioned for growth and more attractive to potential buyers.

The Best Opportunity Isn’t Always the Highest Offer

Business owners often care deeply about their employees, customers, culture, and legacy. As Dara explains, the highest outcome is not always the highest offer. For some owners, cultural fit, employee continuity, future growth opportunities, or alignment with a buyer’s vision can be just as important as valuation. 

This is why Benchmark international evaluates opportunities through a balanced lens.

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Whether a sale is months away or years down the road, this conversation gives valuable insight into what it means to truly be market-ready and why the best outcomes are built long before a business goes to market. With the right guidance and a willingness to explore options, business owners may make more well-informed decisions about their future, their team, and their legacy.

Tune in to this episode of Closing Remarks. Dara Shareef and Ben Wagner discuss market readiness and buyer expectations. They also cover private equity and steps owners can take today. These steps can help create more options for tomorrow.

You can now watch the full episode of Closing Remarks featuring Ben Wagner, now streaming on Spotify,  Amazon Music,  Apple Podcasts, and YouTube.

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