Navigating the Transaction: What Multi-Unit Owners Should Expect When Selling Their Business
January 29, 2026
By Bo Wilkins
There’s a psychological shift that happens during every business sale—a moment when owners stop thinking of the business as theirs and start thinking of it as belonging to someone else. This creates a challenging period where they’re supposed to keep running the business at peak performance while emotionally they’ve already begun to move on.
According to Bo Wilkins, Managing Director at Oxford Financial Group, understanding what to expect during the transaction process can make the difference between a smooth exit and a painful ordeal. The reality is that selling a multi-unit operation is more complex, takes longer, and tests owners in more ways than most anticipate.
The Timeline Reality
Many owners expect selling a business to be like selling a house: list it, get offers, pick one, close in 60 days. The actual process looks nothing like this.
The typical timeline for selling a multi-unit operation runs between eight and eighteen months from serious buyer engagement to receiving the final wire transfer. Bo also regularly reminds his clients that the process isn’t linear—there are periods of intense activity followed by weeks of waiting, then more activity, then more waiting.
The transaction typically breaks down into several distinct phases. First comes preparing the business for market, which involves getting financials pristine, operations documented, and the growth story ready to present. Then comes the marketing phase, either working with an investment banker to create deal materials and reach out to potential buyers, or responding to an unsolicited approach.
Once there are interested buyers, Letters of Intent (LOIs) or Indication of Interest (IOIs) arrive. These are non-binding expressions of interest that outline proposed terms from a potential buyer. This is a critical juncture where many owners make costly mistakes. A number that looks attractive on the surface may have problematic structure underneath.
Consider two hypothetical offers: one for $18 million and one for $16 million. The higher offer might include $5 million in earnouts contingent on hitting aggressive targets after the sale, when the owner no longer controls operations. The lower offer might be $14 million cash at closing with only $2 million in earnouts based on much more reasonable targets. The “lower” offer could actually be worth more with significantly less risk.
Bo works with his clients to understand that purchase price is only one factor. The structure matters enormously—how much is cash at closing versus earnouts or seller financing. He counsels clients that the conditions and representations being made matter – what happens ifsomething goes wrong post-close matters. Understanding all these elements requires careful analysis, not just a quick reaction to the headline number.
Due Diligence: Where Deals Are Made or Broken
After accepting an LOI, the due diligence phase begins. This is when the buyer’s team—accountants, lawyers, operations specialists, sometimes IT consultants—thoroughly examines the business to verify everything that’s been represented.
This is typically the most stressful part of the process for owners. It feels invasive. Every aspect of the business gets questioned, documentation on historical events gets requested, and key employees get interviewed. It can feel like a fundamental lack of trust.
But the buyer’s perspective is straightforward: they’re spending millions of dollars and need to know what they’re buying. If preparation has been thorough and everything is as represented, due diligence is simply a process to work through. If preparation was inadequate, this is where deals fall apart.
Bo has seen that deals can fail during due diligence for numerous reasons: it could be due to undisclosed lawsuits or regulatory issues, financial numbers that don’t reconcile, revenue that was overstated, key employees who indicate they’ll leave, lease terms that are worse than expected, or even equipment requiring more capital investment than anticipated.
The transactions that survive due diligence with original deal terms intact are invariably those where owners did their homework ahead of time. Numbers are accurate because proper accounting systems have been in place, processes are documented, and records are well-maintained. Nothing was unknown or misrepresented.
This is where, according to Bo, having a coordinated advisory team becomes essential. The accountant needs to be responsive to information requests and able to explain financials clearly. IT infrastructure needs to be documented and defensible. Legal counsel needs to review every document and flag potential issues before they become deal-killers.
This is a point where data accessibility can become a surprising obstacle. If a business switched systems years ago and old data wasn’t properly archived, reconstructing historical information during due diligence creates delays and erodes buyer confidence. Thinking about data management and accessibility as part of exit preparation prevents these problems.
Managing Operations During the Sale
One of the most challenging aspects of the transaction period, according to Bo’s clients, is maintaining business performance while managing the sale process itself. Most owners still need to run their businesses during all of this transaction activity.
Performance slippage during the transaction is dangerous. Buyers typically have contractual outs. If EBITDA drops by more than a certain percentage between LOI and closing, they can renegotiate or walk away entirely. Staying focused on operations while spending significant time dealing with the sale is brutally difficult.
This is where having a strong management team pays enormous dividends. If the business can run without the owner being involved in every detail, operations can be delegated while the owner focuses on the transaction, not to mention that this is usually a key element buyers want to see in a company they are purchasing. Without that in place, the owner will get stretched impossibly thin.
Another critical factor for owners to consider during the due diligence process is managing information flow. Key employees need to know about the sale, especially if they’re being interviewed as part of due diligence, but having the entire company on edge for months wondering about job security isn’t productive. Additionally, competitors definitely shouldn’t know until after closing, so managing the information flow to various groups is vital.
The Emotional Journey
The transaction process, according to Bo, is as much an emotional journey as a financial one. There’s often excitement initially—this is finally happening, there’s a significant payday coming. But as due diligence grinds on, doubt can set in about whether the deal will actually close and frustration can build with all the questions and requirements.
There can also be unexpected grief. Owners who’ve built something from nothing sometimes feel like they’re betraying what they created by handing it to someone else who might change everything. That sense of loss is real, even when the transaction is financially successful.
Bo tells clients that acknowledging these emotions rather than suppressing them is the healthiest thing they could do. Talking with spouses or partners, connecting with other people who’ve been through exits, working with advisors who understand transitions—all of these help process what is fundamentally a major life change.
When Deals Don’t Close
Not every deal that reaches the LOI stage makes it to closing. An estimated 30 – 40% of transactions fall apart somewhere in the process.
Sometimes due diligence uncovers genuine problems. Sometimes buyers get cold feet or their financing falls through. Sometimes owners realize they’re not actually ready to sell. And sometimes external factors—economic downturns, market disruptions, industry-specific challenges—change the landscape.
The key, Bo says, is not being devastated when a deal falls apart, especially early in the process. Until the wire transfer is complete and the money is actually in the account, nothing is certain.
He tells clients that each attempt teaches lessons that make subsequent efforts more likely to succeed.
The Advisory Team’s Critical Role
After ‘taking sufficient time to prepare’ for the sale, Bo tells clients that the difference between smooth transactions and nightmares often comes down to having the right advisory team in place.
An experienced M&A attorney who handles these transactions regularly is essential. An accountant who understands transaction structures and can model tax implications of different deal terms is crucial. A financial advisor who can help think through post-transaction life is important. Depending on the business, specialized consultants for areas like IT systems, real estate, or regulatory compliance may also be needed.
But having these advisors isn’t enough—they need to work together. The best transactions involve coordinated advisory teams where the attorney flags tax issues for the accountant, the financial advisor raises questions about deal structure for the attorney to address, and everyone looks out for the client from different angles.
When advisors work in silos, problems emerge. The attorney does their work, the accountant does theirs, nobody communicates. Then at closing, conflicts appear between legal documents and tax structure. This can result in deals getting delayed or terms getting renegotiated at the last minute.
The cost of a strong advisory team is real—often several hundred thousand dollars for a mid-sized transaction. But the difference in deal quality and terms, not to mention the smoother experience, typically pays for those fees many times over.
PE Partnerships: A Different Structure
Private equity partnerships are increasingly common in the restaurant and retail sectors and deserve special consideration. These differ from traditional sales because the owner typically rolls over a portion of equity and stays involved.
The advantage is immediate liquidity to reduce risk and diversify, plus the potential for a larger payday later when the PE firm eventually exits. The tradeoff, Bo points out, is giving up control. The owner becomes accountable to a board, has financial reporting requirements, and needs to hit growth targets in the plan.
For some owners, this path is ideal. It provides capital while allowing continued involvement in a business they love. For others, they find it to be frustrating. Twenty years of being the sole decision-maker makes reporting to a PE board feel constraining.
One thing that Bo also points out to clients is that due diligence for PE deals is often more intensive than for strategic sales because PE firms are betting on future growth, not just current performance. They want to understand everything about the business model, competitive position, growth potential, and team capabilities before making the investment.
Reaching the Finish Line
Despite all the challenges, most well-prepared deals that are appropriately priced do eventually close. The wire transfer usually hits the account within hours of signing final documents. That’s when the transaction becomes tangibly real.
But the transaction itself is just the end of one chapter. What comes next—life after the business—presents its own set of challenges that, Bo says, many owners find even more difficult to navigate than the sale process itself.
Understanding what to expect during the transaction helps owners prepare mentally and practically for the journey. Bo prepares his clients that the process will test patience, organization, and emotional resilience. But with proper preparation, the right team, and realistic expectations, he tells them, the path from decision to closing can be navigated successfully.
The key is approaching the transaction not as a single event but as a complex process requiring sustained focus, professional support, and the willingness to work through challenges as they arise. Owners who understand this from the outset position themselves for the best possible outcome.
The third article in the series will be published in February 2026.
This article is provided for informational and educational purposes only and should not be construed as personalized investment, legal, or tax advice. The views expressed reflect those of the author based on their experience and professional judgment. Past performance and experience do not guarantee future results. All examples are hypothetical and for illustrative purposes only.Please consult your financial advisor regarding your specific situation.
Oxford Financial Group, Ltd. (“Oxford”) is a Registered Investment Advisor (“RIA”) with the U.S. Securities and Exchange Commission (“SEC”) and is headquartered in Carmel, Indiana. Registration with the SEC does not imply a certain level of skill or training. Additional information about Oxford, including our Form ADV and Privacy Policy, is available upon request by calling 800.722.2289 or emailing [email protected]. OFG-2511-43
Written in collaboration with
Bo Wilkins
Bo Wilkins is Managing Director at Oxford Financial Group, Ltd™., where he works closely with colleagues and clients’ advisors to design innovative wealth transfer strategies for business owners and family offices. With over 30 years of experience in estate, legacy, and business succession planning, Bo is recognized as a published thought leader, frequent speaker and active board member in both professional and philanthropic organizations.
