This one has an interesting wrinkle. The listing advertises a 10.67% cap rate, but the same property also appears to be marketed as available for lease. Before doing any serious underwriting, what are the first three questions you would ask the broker? Drop yours in the comments. Then we'll work through the deal together: The Questions → The Underwriting → The Offer → The Decision

For nearly two months, the buyer and seller kept returning to the same disagreement. The buyer believed the asking price was simply too high. The seller believed the company's performance justified every dollar of it. Each conversation ended in roughly the same place, with neither side willing to move enough to close the gap. Eventually, the buyer stepped away from the negotiation and rebuilt the transaction from the ground up. Instead of asking what price he was willing to pay, he modeled exactly what would happen at closing and during the first several years of ownership. That's when he discovered something unexpected. The purchase price wasn't actually the problem. The business could support the valuation, debt service remained reasonable, and the projected returns still worked. What made the transaction uncomfortable was the amount of equity required on day one. Between the down payment, transaction costs, working capital, and reserves, too much cash was leaving the buyer before he had operated the business for a single day. For weeks, he had been negotiating the wrong number. When he returned to the seller, he didn't ask for another price reduction. Instead, he explained the constraint and proposed changing the capital structure. They discussed a larger seller note, a smaller amount of senior debt, and enough working capital remaining in the business to give the new owner room to operate after closing. The seller was receptive because the conversation no longer required him to defend the value of the company. He could still receive the price he believed the business deserved, while the buyer could reduce the amount of equity exposed at closing. The economics finally worked, not because either side surrendered on valuation, but because they stopped treating price as the only variable available to negotiate. That experience changed how the buyer approached future acquisitions. A deal can be fairly priced and still be poorly structured. Purchase price tells you what you're paying for the business, but capital structure determines how much risk you're assuming to own it.

The buyer and seller had spent weeks trying to close a valuation gap. The seller believed the company's recent growth justified a higher price, while the buyer wasn't comfortable paying today for earnings that had yet to materialize. Neither wanted to lose the transaction over a disagreement about the future, so their advisors proposed what seemed like an elegant solution. They would use an earnout. The seller would receive additional consideration if the business reached certain performance targets after closing. The buyer would pay the higher valuation only if the results actually appeared. On paper, it seemed to give both sides exactly what they wanted. The problem was that everyone focused on the amount of the earnout and not enough on how it would be measured. The agreement referenced revenue and profitability targets, but left important questions unresolved. How would unusual expenses be treated? Could the buyer increase staffing or marketing after closing? What happened if an investment reduced short-term profit but strengthened the company long term? Who controlled pricing, and how would revenue from new products be allocated? Those questions seemed manageable while everyone was trying to close. A year later, they weren't. The business had grown, but the buyer had also invested heavily in people, systems, and equipment. The seller believed the earnout had been achieved based on the company's underlying performance. The buyer's calculations showed otherwise. Neither side believed they were being unreasonable. They were simply interpreting an ambiguous agreement in the way that supported their own position. The earnout hadn't resolved their valuation disagreement. It had postponed it. Eventually, attorneys became involved, and a provision designed to save the transaction became one of its most expensive sources of friction. Looking back, both sides realized they had spent more time negotiating the potential payout than defining the rules that would determine whether it was earned.

The buyer and seller were days away from closing. Due diligence was complete, financing was approved, and the purchase agreement had been negotiated down to a handful of final items. After months of work, both sides believed the difficult decisions were behind them. Then the closing statement arrived. The buyer expected the business to be delivered with enough working capital to support normal operations after the transition. The seller expected to collect most of the cash and receivables before closing while leaving the buyer responsible for funding the business going forward. Both pointed to the same phrase in their agreement: "normal working capital." The problem was that they had never agreed on what normal actually meant. What initially looked like an accounting adjustment quickly became a significant economic disagreement. The buyer argued that paying the agreed purchase price and then immediately injecting additional cash effectively increased his acquisition cost. The seller believed leaving more capital behind meant receiving less of the value he had negotiated. Neither believed they were changing the deal. Each believed the other side was. With closing approaching, emotions escalated because both parties had already invested months in the transaction. Attorneys became involved, spreadsheets moved back and forth, and a deal worth millions nearly collapsed over a term everyone had assumed was settled weeks earlier. Eventually, they stopped debating the phrase and started defining it. They reviewed historical balance sheets, examined the company's normal operating cycle, and calculated what the business actually required to pay employees, vendors, and other obligations without needing an immediate cash injection. From there, they agreed on a specific working capital target and a mechanism for adjusting the purchase price if the amount delivered at closing was above or below it. The deal closed, but the experience changed how the buyer approached future transactions.

The seller's message arrived on a Tuesday afternoon. Another buyer was interested, he explained, and if the current buyer wanted the business, he needed a decision by Friday. There would be no extensions, and the seller made it clear that improving the offer would probably make the decision easier. The buyer had already spent weeks analyzing the company. He liked the business, understood the opportunity, and could see himself owning it. Losing the deal over a relatively small increase in price would be frustrating, particularly after the time and money already invested. For the next two days, he reconsidered his assumptions. He reran the numbers, challenged his downside case, and asked whether he was being overly conservative. But every version of the analysis brought him back to roughly the same conclusion. His offer reflected what he believed the business was worth and the risk he was prepared to accept. So on Friday, he did something uncomfortable. He let the deadline expire. The seller moved forward with the other buyer, and the opportunity disappeared. For several weeks, the buyer wondered whether discipline had cost him a good acquisition. It is easy to talk about walking away when another opportunity is theoretical. It feels very different when a business you genuinely want is suddenly gone. Six weeks later, his phone rang. It was the seller. The other transaction had stalled during diligence. The competing buyer had changed several terms, financing was taking longer than expected, and the certainty the seller thought he had chosen was beginning to disappear. He wanted to know whether the original buyer was still interested. This time, the conversation felt different. The buyer wasn't negotiating against a deadline or an unseen competitor. They could discuss the business on its merits and determine whether a transaction still made sense. The experience taught him that urgency and leverage are not the same thing. A seller may genuinely have another buyer, and the deadline may be completely real. But neither changes what the business is worth to you or how much risk you should be willing to accept.