Introduction

For many business owners, selling their company represents the culmination of decades of hard work. Yet too often, owners approach an exit without a clear strategy, clean financials, or an understanding of how buyers actually evaluate businesses. The result? Missed value, delayed deals, or exits that fall apart entirely.

In this episode of There’s a Solution for That, Brad White sits down with Jackson Payne, Managing Partner at Viking M&A, to unpack what business owners need to know about growing enterprise value, preparing for a sale, and avoiding the costly mistakes that can derail a transaction. Drawing from decades of experience—and hard-earned lessons as a former seller himself—Jackson shares what truly drives successful exits.

Understanding the Business Sale Landscape

Jackson explains that most business sales fall into two broad categories:

• SBA-backed transactions (typically $1–$5 million in enterprise value)
• Middle-market M&A deals (above $5 million, often involving private equity or strategic buyers)

While larger deals attract more headlines, the majority of transactions still happen in the SBA space. These “Main Street” businesses make up the backbone of the economy—and they require just as much preparation and expertise to sell successfully.

The key difference isn’t just size—it’s how buyers finance, evaluate, and structure deals.

Why Tax Returns Matter More Than You Think

One of the most overlooked—and most damaging—mistakes sellers make is aggressively minimizing taxable income year after year without considering the impact on valuation.

For SBA-backed buyers, tax returns are the primary driver of value. While reducing taxes may save a business owner 30 cents on the dollar today, it can cost them three to four dollars in valuation later.

Jackson emphasizes:

• Clean, accurate tax returns matter more than internal financial statements
• Excessive personal expenses, cash-basis distortions, and aggressive write-offs suppress value
• Buyers and lenders trust tax returns because owners rarely overstate income to the IRS

For owners considering a sale in the next few years, proactive tax and accounting strategy is critical.

The Cost of Going It Alone

Jackson shares his own experience selling a family business without representation—an education he describes as “the most expensive lesson” he ever learned.

Many owners believe they can handle a sale themselves, especially when approached by an unsolicited buyer. But Jackson warns: one buyer is no buyer at all.

Without a competitive process:

• Sellers lose leverage
• Buyers dictate terms
• Deal structures favor the buyer, not the seller

Professional advisors bring multiple buyers to the table, creating competition that improves price, terms, and certainty of close.

Why Deals Fall Apart After the Letter of Intent

A signed Letter of Intent (LOI) is not the finish line—it’s the beginning of the most fragile stage of the deal.

Jackson explains that many buyers issue LOIs with no intention of closing, using exclusivity to “tie up” sellers while they explore other opportunities. Without proper vetting, sellers can lose months of time, momentum, and business performance.

Experienced M&A advisors prevent this by:

• Qualifying buyers before they see sensitive information
• Understanding buyer behavior, funding sources, and deal history
• Managing a structured, multi-stage process that filters out weak or disingenuous buyers

Time kills deals, and protecting momentum is essential.

Finding the Right Buyer Fit—Not Just the Highest Price

For most sellers, maximizing value isn’t just about money—it’s about legacy.

Jackson notes that many owners care deeply about their employees, customers, and reputation. Viking M&A prioritizes fit by evaluating:

• Buyer holding period and exit strategy
• Treatment of employees post-acquisition
• Cultural alignment and leadership style
• Willingness to preserve what made the business successful

Private equity firms, family offices, individual buyers, and strategic acquirers all bring different intentions. Understanding those intentions helps sellers make informed decisions beyond headline price.

Asset Sale vs. Stock Sale: What Sellers Should Expect

In roughly 95% of transactions, businesses sell via asset sales, not stock sales. This structure protects buyers from legacy liabilities and allows favorable tax treatment for depreciation.

While asset sales can increase taxes for sellers—especially those with heavy equipment or depreciated assets—most markets dictate this structure. Advisors and CPAs play a critical role in:

• Purchase price allocation
• Minimizing tax exposure
• Setting realistic expectations early in the process

Understanding this upfront prevents surprises later.

The Role of Advisors, Lenders, and Legal Teams

Selling a business requires a coordinated team. Jackson highlights the importance of experienced professionals who specialize in transactions—not generalists.

Key players include:

• Lenders who understand deal size, industry, and SBA nuances
• M&A attorneys familiar with market-standard terms and timelines
• Insurance providers who can meet strict SBA life insurance requirements
• CPAs who can support valuation and tax planning

Using the wrong professional can delay—or derail—a deal entirely.

Preparing Early Creates Options

One of the most powerful takeaways from the episode is the importance of early preparation.

Jackson recommends that owners begin thinking about an exit three to five years in advance, allowing time to:

• Clean up financials
• Improve cash flow
• Reduce owner dependency
• Build a leadership team
• Invest in growth opportunities that buyers will value

Businesses that can operate without the owner for extended periods are far more attractive—and valuable—to buyers.

The Biggest Mistakes Sellers Make

According to Jackson, the most common seller mistakes include:

• Ignoring professional advice
• Using inexperienced attorneys or lenders
• Poor bookkeeping and inconsistent financial records
• Waiting too long to plan
• Focusing solely on price instead of structure and certainty

Cash flow drives valuation. Clean books, strong systems, and disciplined planning make the difference between a smooth exit and a failed one.

Conclusion

Selling a business is not a single transaction—it’s a process that rewards preparation, discipline, and expert guidance.

This episode makes one thing clear: owners who treat their exit with the same seriousness as they treated building their business consistently achieve better outcomes. With clean financials, the right advisors, and a competitive process, sellers can protect their legacy, maximize value, and exit on their own terms.

For business owners thinking about the future, the best time to start preparing for a sale is long before the phone rings.