Where value meets values: Advising on the sale of mid-market family businesses

As the “silver tsunami” reshapes the US business landscape, succession planning is becoming a key consideration for business owners. More than half of US small-business owners are now over the age of 55, and many must decide who will carry their legacy forward. 

Tony Petretti is a co-founder of Olivewood Advisors, an M&A advisory firm that advises owners of mid-market businesses, many of them family-run, through the sale of their companies. 

Tony shared what makes family succession different from a standard sale process, the factors owners underestimate, and what defines a successful exit beyond the price tag. 

Q. What led you to found Olivewood Advisors? 

My background is in investment banking and I’m a CFA charterholder. However, my understanding of how companies operate started earlier. My first job was on the floor of a family-owned glass manufacturer, where I saw what it meant to run a company and the importance these businesses hold for the families behind them. 

Today, a generation of business owners is approaching retirement, creating a succession challenge many have never faced before. This is their first experience navigating a transition of this kind, and the decision is deeply personal. 

My partners, Phil Daniels and David Clark, and I founded Olivewood Advisors to serve these owners. We describe our approach as working at the intersection of value and values. We bring the transaction experience of larger banks, while providing the dedicated attention and personal guidance each owner deserves. 

Value is the number on the page. Values are what matter beyond that number: their staff, their legacy, and the life they want next. 

Q. Why is a family business succession different from a traditional sale? 

The decision is rarely just about finding a buyer. Owners are weighing questions about legacy, continuity, and what happens to the business they built. Some have children in the business who may not want to take over, while others have no family involved at all. 

Either way, what comes next is rarely just a financial decision. 

Some owners are looking for a partner to help accelerate the next phase of growth. Others want to preserve autonomy and remain involved in a leadership capacity, while some are ready for a complete transition away from the business. 

The right path depends on what the owner wants the next chapter to look like and how their role fits into the company’s future. 

Q. What should owners do before they consider selling their business? 

We encourage owners to begin preparing 12–24 months in advance, because most of the value is created before a process begins, not during it. 

Think about what a buyer is actually paying for: clean and consistent financials, limited customer concentration, a management team that can operate without the owner, and documented systems and processes. Those are not things you can build in 90 days after an offer lands.

Understanding how buyers evaluate a business is another important step. Two companies with similar revenue and EBITDA can command very different outcomes depending on factors like industry dynamics, management depth, customer diversification, financial quality, and growth potential. 

The earlier owners gauge what drives value, the more time they have to strengthen the business.

Q. How do you help owners find the right buyer for their business? 

This is where the “who” starts to matter more than the “how much.” The first question is whether the buyer is capable of delivering on the transaction: can they actually fund the deal, and have they successfully completed similar transactions before? 

From there, it’s about understanding what sits behind the headline number. How much is cash at close versus rollover equity? Are there earnouts, escrows, or holdbacks? Two offers with the same headline valuation can represent very different outcomes for the seller. 

Equally important is understanding how the buyer operates after closing. What happened to the last three companies they acquired? Are those leadership teams still in place? Did they invest in growth or consolidate operations? That history often tells you more than any pitch deck. 

Finally, buyer behavior during diligence can be revealing. The way a buyer approaches the process provides a preview of how they will operate as a partner after closing. The highest bid and the best fit are not always the same thing.

Q. What do owners often underestimate during and after the sale process? 

They can underestimate the intensity of due diligence. Owners are managing hundreds of requests, negotiating deal terms, and running the business at the same time. It’s one of the most demanding parts of the process because the company still needs to perform while the transaction progresses.

The other major challenge is the change in identity. Someone who has spent decades building a company often has that business tied closely to their purpose, routine, relationships, and reputation. None of that transfers at closing. You sell a company, but you do not hand off who you have been. 

One factor some owners don’t anticipate is the impact a competitive process can have on the outcome. In today’s market, it’s common for a strong company to receive an unexpected call from a buyer. That interest is flattering, and it tends to move quickly, but negotiating with a single party is very different from running a process where qualified buyers compete. 

Creating that competition, and managing it while the business continues to operate, is often where an advisor makes the biggest difference. 

Q. What makes an owner look back on a transaction and feel they made the right decision? 

The owners who feel confident afterward are the ones who entered the process with a clear understanding of how they would measure success. When difficult decisions arise, that gives them a framework for evaluating options and staying focused on what matters.

They also understand that the right outcome is about more than the transaction itself. It’s about choosing a path that aligns with their goals, their people, and the future they want for the company. 

Owners who take the time to think through those trade-offs are better positioned to feel confident in their decision down the road.