When a business owner decides to sell their company, most of the attention naturally focuses on the transaction itself. Questions about valuation, buyers, taxes, and deal terms often dominate the conversation. But according to research from the Exit Planning Institute, 75% of business owners regret selling their business within 12 months of the transaction.
Surprisingly, that regret is rarely about the money.
A successful exit requires much more than finding the right buyer. It involves preparing the owner and the business for what comes after the sale. That preparation is often best achieved with a coordinated team of exit professionals to navigate the financial, operational, legal, and personal considerations involved in the transition.
Here, Tara Unverzagt, Senior Financial Planner at South Bay Financial Partners; Michael Whelchel, Founder and CEO of Big Path Capital; and Jim Black, Co-Founder and Managing Partner at ImpactGC, share their perspectives on what business owners should know before selling a company and why preparation often begins years before the sale itself.
The Financial Planner: Preparing for Life After the Sale
One of the biggest challenges business owners face during a sale isn’t financial at all. It’s the realization that after decades of building a company, the business has become deeply intertwined with their identity.
“There is a piece that is a financial transaction, definitely,” says Tara Unverzagt, Senior Financial Planner at South Bay Financial Partners. “But there is also the transition from being a business owner to not being a business owner. A lot of business owners don’t consider that.”
The challenge, she says, is that many founders spend years focused on growing the business without realizing how much of their time, energy, and sense of purpose has become tied to it. Unverzagt believes this dynamic helps explain why so many owners struggle after an exit. “A lot of that is because they were exiting out of something, but they weren’t entering into anything,” she says. For that reason, one of the most important questions a business owner can ask has nothing to do with valuation or deal structure. “What is the next chapter going to look like?” Unverzagt asks. “What’s important to you? What skills do you have that you want to continue to hone and offer to the world?”
Financially, the shift can be just as significant. “A lot of business owners put all of their money into their business,” says Unverzagt. “So now, when that’s gone, and they have this gob of money, they don’t even know how to spend it because they haven’t had time to spend it before.”
That sudden wealth can bring challenges that owners rarely anticipate while they’re focused on growing a business. Tax obligations increase, financial decisions become larger and more complex, and relationships can change as friends and family adjust to a new reality.
The good news is that many of these challenges can be addressed long before a sale is on the horizon. In fact, Unverzagt believes the best exit planning begins years before an owner intends to leave the business. “You should always be prepared to exit, even if you have no intention of exiting in the next decade or two.”
A financial planner can help owners prepare for that transition by clarifying long-term goals, modeling different future scenarios, and coordinating the broader team of advisors involved in the process. Ultimately, a successful exit isn’t just about maximizing a business’s value. It’s about making sure the owner is prepared for the life that follows.
The Exit Advisor: Building a Business That’s Worth Buying
If financial planners help owners prepare for life after a sale, merger and acquisition (M&A) advisors help prepare the business itself.
According to Michael Whelchel, Founder and CEO of Big Path Capital, many owners underestimate how far in advance they should begin that process. Big Path primarily works with companies that have a positive impact aspect to their business. The firm has a long history of advising business owners on the whole or partial sale of businesses without compromising mission. “Many founders underestimate how much time a proper sale process takes,” says Whelchel. “Six months is on the shorter timeframe. It can take up to 12 months from preparation to close, and entering a process underprepared can actually depress value.”
That preparation extends far beyond financial performance alone. Buyers evaluate operational systems, documented processes, team depth, leadership succession, and the organization’s overall resilience. For many owners, maximizing value isn’t about making last-minute improvements before a sale. It’s about building a stronger business over time.
For owners who have built businesses around a social or environmental mission, the challenge often includes preserving that impact while creating a company that can thrive under new ownership.
“The most attractive businesses are those where strong financials and a clear mission reinforce each other, not despite one another,” says Whelchel. “Companies where there is positive environmental and social returns embedded in the business model, not bolted on as a marketing claim, are best positioned for impact buyers.”
While every buyer has unique priorities, certain qualities consistently signal that a business is healthy, scalable, and well-positioned to thrive under new ownership. Clean, auditable financials are essential. Recurring revenue provides predictability. A strong management team demonstrates that the company can continue operating without constant founder involvement. Buyers also look for a differentiated market position and a customer base that would be difficult to replicate from scratch.
“Founders sometimes assume that a strong purpose story will carry a deal even when the underlying financial performance is weak or inconsistent,” says Whelchel. Others focus on revenue without accounting for factors such as profitability, customer concentration risk, competitive advantages, or the extent to which the business depends on the founder’s personal relationships.
Mission-driven business owners can be particularly vulnerable to this misconception. While certifications, values statements, and impact commitments may strengthen a company’s story, buyers still expect evidence that those commitments translate into measurable results.
An experienced M&A advisor can help owners identify the factors that buyers care about most and prioritize the changes that will have the greatest impact on valuation, readiness, and long-term success after a transition.
The Legal Team: Addressing Problems Before a Buyer Finds Them
Even highly successful businesses can encounter obstacles during the sales process. In many cases, those obstacles aren’t related to revenue, profitability, or market position. Instead, they stem from unresolved legal, ownership, or governance issues that surface during buyer due diligence.
According to Jim Black, a highly experienced corporate lawyer and Co-Founder and Managing Partner at ImpactGC, one of the most important steps owners can take before pursuing a sale is to ensure complete clarity about who owns the company.
That means more than simply confirming current ownership percentages. Business owners should also identify anyone who may have a potential claim to equity, whether through stock options, warrants, convertible notes, SAFEs, inheritance, or even informal promises made years earlier.
“Nothing will kill a company sale faster than a dispute over who owns it,” says Black. “Sellers should always try to surface and address any potential disagreements over ownership rights long before engaging with potential buyers.”
Ownership questions are only one part of the picture. Buyers also conduct extensive due diligence to identify risks that could affect the company’s value after acquisition. The more organized and prepared a seller is, the smoother that process tends to be.
“I highly recommend that sellers conduct due diligence on their own company, including assembling all relevant documents in a well-organized virtual data room, so they can identify and potentially address any key risks or liabilities before launching a sale process.”
That proactive review often uncovers issues that may have been lingering in the background for years, including unresolved contractual disputes, employment-related claims, intellectual property concerns, threatened litigation, and other business-specific risks.
“It is far better to know in advance what a potential buyer will view as a material risk or liability so that the sellers can reduce or eliminate it,” says Black. “For example, by settling a long-simmering dispute before it becomes an issue in the sale process.”
Legal preparation may not be the most visible part of a business sale, but it can be one of the most consequential. By identifying ownership questions, organizing documentation, and addressing potential liabilities before going to market, legal advisors help reduce surprises that can delay negotiations, diminish value, or derail a transaction altogether.
Why These Advisors Can’t Work in Silos
By the time a business owner reaches the point of selling their company, they may be working with a wide range of professionals: financial planners, accountants, attorneys, business brokers, valuation specialists, and transaction advisors. Each brings a different area of expertise, but a successful exit depends on more than simply assembling the right team.
It depends on making sure the team works together.
According to Unverzagt, one of the most important roles in the exit process is to ensure that all these moving pieces stay aligned with the owner’s goals. “The financial planner can be the quarterback to help coordinate all these different people,” she says. “Somebody needs to be the coordinator, because the business owner really doesn’t have the time, the energy, or the skill set.”
That coordination becomes increasingly important as a transaction progresses. Decisions made in one area often create consequences in another. A legal provision can affect financial outcomes. A valuation assumption can influence deal negotiations. A tax strategy may impact estate planning. Without communication among advisors, important details can easily be missed.
Black sees this firsthand during transactions. “Stock or asset purchase agreements, while typically drafted and negotiated by lawyers, often include provisions that relate to financial metrics or commercial topics that other advisors are better suited to address,” he says.
“There are numerous other areas in which effective collaboration is important to a successful deal,” says Black. “Sellers should always try to ensure that advisors do not work in silos.”
The same principle applies long before a company reaches the negotiating table. As Whelchel points out, buyers evaluate businesses through multiple lenses at once. Financial performance, operational maturity, leadership depth, documented systems, and mission alignment all influence how a company is perceived and valued. Preparing for that scrutiny requires expertise that no single advisor can provide on their own.
Ultimately, selling a business is not a series of separate conversations. It is one interconnected process that touches nearly every aspect of an owner’s personal and professional life. Financial, legal, operational, and personal readiness all influence one another.
The strongest outcomes often occur when advisors are not simply solving problems within their own disciplines, but collaborating toward a shared objective: helping the owner transition successfully into whatever comes next.
South Bay Financial Partners offers financial planning for every stage of life, including the sale of a business. Book an intro call today to get started.