The Exit Planning Paradox: Why Restaurant and Retail Owners Need to Start Before They’re Ready
January 15, 2026
By Bo Wilkins
The biggest mistake multi-unit restaurant and retail owners make isn’t usually about operations, marketing, or even hiring. It’s often about timing—specifically, waiting until they’re ready to exit before they start planning for it.
“People wait until they’re ready to exit before they start planning,” says Bo Wilkins, Managing Director at Oxford Financial Group. “By then, it’s often too late to maximize value or even execute the exit they want.”
It’s a paradox that defines the industry. Business owners spend decades building their operations—multiple locations, loyal teams, efficient systems—but when it comes to the most important financial transaction of their lives, many approach it reactively rather than strategically.
The “Someday” Mentality
Most business owners say they’ll think about exit planning “someday.” Then someday arrives in the form of burnout, a health scare, or an unsolicited offer, and suddenly they’re making a decades-defining decision in a matter of weeks.
The problem isn’t that owners don’t care about their exit. The day-to-day demands of running multiple locations leave little mental space for planning something that feels distant and abstract. Labor costs, supply chain issues, technology problems, and personnel management dominate the daily agenda. Exit planning feels like something for ‘Future You’ to worry about.
But ‘Future You’ will wish ‘Present You’ had started sooner.
The Three-to-Five-Year Window
According to Bo, the ideal timeline for exit planning is three to five years minimum, with five being preferable to three. This isn’t arbitrary—this timeline is based on Bo’s decades of experience with business owners, knowing what it actually takes to prepare a business for maximum value, and to prepare the owner for life after the business.
In years four and five before an exit, Bo tells his clients the focus should be on understanding current position. What’s the business actually worth? Not hoped-for value or conference-floor comparisons, but actual market multiples for similar businesses. For restaurant groups, that might be four to six times EBITDA depending on the concept and growth trajectory. For retail, it varies widely based on e-commerce integration and market position.
This is also when personal balance sheet diversification becomes critical. In the conversations with his clients about this, Bo walks them through the concept of the “liquidity pyramid.” At thebase sit illiquid assets—primarily business equity. In the middle are somewhat liquid assets like real estate. At the top are truly liquid assets like diversified investment portfolios.
Too many operators have an inverted pyramid with everything concentrated in the business. While they might own their buildings, if they need cash for something personal, they have almost no options. That’s a precarious position, even before considering exit planning.
In years three and four before an exit, Bo has clients focus on operational optimization and documentation. Buyers are looking for businesses that can run without the owner. They want to see systems, processes, and data that prove the business is a well-oiled machine, not just a manifestation of the owner’s personal hustle.
This means financial reporting needs to be bulletproof—not just “good enough for tax purposes” but actually precise, timely, and detailed. Deals can slow down or fall apart entirely during due diligence when financials are disorganized. Buyers can lose confidence and start assuming problems exist that they just haven’t found yet. Once that happens, they either walk away or dramatically reduce their offer.
Proper systems matter: uniform chart of accounts across all locations, monthly closes that actually happen like clockwork, clear reporting on unit-level profitability. When financial data is clean and well-organized, it makes the entire transaction process smoother and almost certainly improves valuation.
Technology infrastructure also matters more than most owners realize. If systems are held together with workarounds and the institutional knowledge of one long-tenured IT person, that’s a red flag. Buyers want to see modern, scalable systems and support infrastructure that won’t require a complete overhaul post-acquisition.
Lastly, Bo says, the final year or two should be about maximizing EBITDA and creating the growth story. Buyers pay for trajectory as much as current performance. Systematically improving margins, opening new units successfully, or capturing market share builds a narrative that justifies a premium multiple.
The Value of Clean Data
Financial housekeeping impacts valuation more than many owners realize. Not because EBITDA changes, but because buyer confidence changes. Two businesses with identical financial performance can receive different offers based purely on trust and confidence in the numbers.
Consider two hypothetical retail groups going to market simultaneously with similar revenue and profitability. One has invested in proper financial systems and regular audits. The other has numbers that are “probably right” but hard to verify. The first typically receives multiple offers at the high end of the expected range. The second typically gets lowball offers and numerous requests for price reductions after due diligence reveals inconsistencies.
The difference in final sale price can be substantial—potentially millions of dollars—because of insufficient investment in proper accounting infrastructure.
Beyond the Numbers
One key truth that Bo shares with his clients preparing for an exit, is that financial preparation is only half the equation. Psychological preparation matters just as much, if not more.
The business often becomes the owner’s identity. It’s how they introduce themselves. It’s what gives their life structure and meaning. Selling something that’s been central to identity for 20 or 30 years creates an emotional challenge that pure financial planning can’t address.
This is where the five-year timeline proves its value. Bo finds it gives owners the time they need to start thinking about who they are beyond the business. They are able to develop interests and relationships that aren’t connected to their restaurants or stores. It’s vitally important time for them to get comfortable with the idea that their legacy is secure and that there’s a full life waiting on the other side.
Bo notes that some clients complete all the financial preparation perfectly but then can’t pull the trigger when the time comes. They reach the finish line and realize they’re not ready to stop being who they’ve always been. Starting the psychological preparation conversation earlier allows for gradual adjustment instead of a crisis at the worst possible moment.
The Preparation Payoff
When exit planning is done right—starting early, doing the work, and approaching the exit strategically—everything becomes easier. Valuation is higher because buyers have confidence. The transaction is smoother because there are fewer surprises. And the owner transitions into their next chapter feeling proud of what they built and excited about what’s next, instead of relieved it’s over or full of regret about money left on the table.
In Bo’s experience, proper preparation creates a fundamentally different experience. It can lead to things like multiple offers above asking price, due diligence that finds nothing concerning, or closing in four months instead of eight to twelve. And most importantly, it leads to an owner who feels ready for the transition—not scared, not sad, not simply relieved, but genuinely ready.
That’s the power of starting before it feels necessary. Five years seems like forever when you’re in the middle of running a business. But it passes faster than most people expect, and when the exit moment arrives, having a plan instead of hoping for the best makes all the difference.
In every case, the question isn’t whether there will eventually be an exit. One way or another, Bo tells his clients, everyone exits their business. The question is whether it happens on the owner’s terms or on circumstance’s terms. Starting planning now—even if “now” feels absurdly early—sets up the possibility of the former rather than the inevitability of the latter.
This is the first of a three-article series written in collaboration with Bo Wilkins, Managing Director at Oxford Financial Group, about the process of preparing for, navigating through, and finding life on the other side of an exit transaction. The remaining articles in the series will be published in 29th January 2026 and 12th 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.
