You Are the Underdog in Your Own Transaction
Here is a number that should give every founder pause.
A typical strategic or financial buyer reviews somewhere between 2,000 and 3,000 potential acquisition targets to complete five or six purchases in a given year. They have entire teams dedicated to sourcing, evaluating, and closing deals. They know exactly what questions to ask, what red flags to look for, and how to structure a deal in their favor.
You are going to sell your business exactly once.
Buyers have done this hundreds of times. You’ve done it zero. That asymmetry defines everything about the transaction.
I lived this firsthand. In 2015, after 14 years of building Enjoy Life Foods, we sold the company to Mondelez International. I went into that process more prepared than most founders — I had a banking background, a formal board of directors, audited financials, and a strong network of advisors. And I will tell you honestly: it was still the most exhausting, humbling, and complex professional experience of my life.
If I had gone in without that preparation, the outcome would have been very different.
The Asymmetry Is the Problem
When you sell your business, you are sitting across the table from professionals who negotiate transactions for a living. They know current market multiples cold. They know which provisions in a purchase agreement tend to favor the buyer. They know how to structure earnouts, reps and warranties, and indemnification clauses in ways that shift risk onto the seller — often without the seller fully realizing it until months later.
This is not a criticism of buyers. It is simply the reality of how transactions work. Buyers are specialists. Most sellers are not.
The data backs this up. A national study of more than 750 business owners found that 37% of those who tried to sell their business were not successful. More striking: 49% said they didn’t know who to trust or where to start, and 43% had never received a formal market valuation. They were going into one of the most significant financial events of their lives without a roadmap.
What I Did Differently — and Why It Mattered
At Enjoy Life Foods, I started preparing for an eventual exit years before we ever hired an investment bank.
Some of what I did was structural. I built an advisory board on day one — not because I had a clear exit timeline, but because I knew I needed credibility, accountability, and expertise I didn’t yet have. That advisory board eventually became a formal board of directors. I upgraded our financials progressively — from a compilation to a review to a full audit — so that we would have the kind of clean, credible numbers that buyers and their due diligence teams expect. I addressed legal matters as they arose rather than letting them accumulate. I kept the cap table organized and communicated regularly with shareholders.
None of this was urgent. All of it was intentional.
Some of what I did was relational. Over the years, I developed strong working relationships with investment bankers, private equity firms, and venture capital groups — not because I needed them in the moment, but because I knew I would eventually. When we were ready to run a process, I already had a network and a reputation. That made the banker selection process faster and the process itself more competitive.
And some of what I did was operational. I focused on building a business that could run without me in the room. I built a leadership team that was capable and credible. I invested in systems and processes that created predictability. I focused obsessively on brand strength and customer loyalty. All of these made the business more attractive to a strategic buyer — not just because they improved the numbers, but because they reduced risk in the eyes of the acquirer.
Exit readiness isn’t something you create in the six months before you sell. It’s something you build over years.
The Three Mistakes I See Most Often
After working with and observing dozens of founder-led businesses, I see three patterns repeat consistently among founders who end up disappointed with their exit outcomes.
1. They wait too long to start preparing
The most common mistake is conflating exit readiness with exit intent. Founders assume that because they’re not planning to sell yet, they don’t need to think about it yet. But the value drivers that buyers reward — reduced owner dependency, recurring revenue, documented processes, strong leadership bench — take years to build. You cannot manufacture them in a six-month sale process.
2. They go it alone
Some founders attempt to manage a sale process themselves, or with only a CPA and an attorney. This is the equivalent of representing yourself in a complex legal matter against a team of experienced specialists. The investment bank fee feels significant until you understand what a well-run process actually produces in terms of competitive tension, deal structure, and final valuation. In my experience, the right investment bank earns their fee many times over.
3. They take their eye off the business during the process
A dip in performance during a sale process is one of the most common reasons deals fall apart or valuations get cut. Buyers are watching. If the numbers soften while you’re negotiating, they will use it. At Enjoy Life Foods, I made a deliberate decision to run the business during normal hours and handle sale-related work after hours — sometimes well into the early morning. It was hard. But the business kept performing, and that performance gave Mondelez the confidence to close.
You Don’t Have to Be the Underdog
The asymmetry between buyers and sellers is real. But it is entirely closeable — with the right preparation, the right advisors, and the right framework.
The founders who exit well are not the ones who got lucky with timing or happened to be in a hot sector. They are the ones who built their businesses with an eventual exit in mind, surrounded themselves with the right people, and treated the sale process with the seriousness it deserved.
Selling a business is usually the crowning achievement of a founder’s career. Give it the time, the resources, and the respect it deserves.
Scott Mandell is a certified Scaling Up coach and the founder of Mandell Strategic Growth. He founded and scaled Enjoy Life Foods from startup to acquisition by Mondelez International in 2015. He works with founder-led and privately held middle market companies in the $10M–$150M range to help them scale smarter and exit stronger. He is hosting a free virtual Scaling Up To Finish Strong Workshop on June 24, 2026 — Click here to register