Blog Posts
Mergers and Acquisitions
AI Can Prepare You to Sell a Business, but It Can’t Replace Experienced Deal Counsel
Artificial intelligence (AI) is rapidly becoming a larger part of mergers and acquisitions (M&A). For a business owner preparing to sell, AI tools can organize information, accelerate document review, and reduce some of the burden of a demanding diligence process. While those capabilities are certainly meaningful, they should not be confused with deal strategy. AI can help prepare a seller for a transaction, but it lacks the ability to determine how to position the business, preserve the negotiated economics, or control liability after closing. Selling a business is much more involved than just collecting documents and answering questions. It is a negotiated allocation of value and risk. The seller may begin with an attractive headline price, but the amount ultimately retained can depend on dozens of provisions that require context, judgment, and a clear understanding of the seller's priorities. These are all things AI cannot understand. When used thoughtfully, AI can be helpful early in the transaction process. It may assist in generating a diligence checklist, classifying documents for a virtual data room, reviewing contracts for recurring provisions, and preparing summaries for the deal team. For a seller looking at years of agreements, corporate records, employment materials, and financial information, that organizational support can be invaluable, saving time and helping identify areas that deserve closer attention. But a well-organized data room is not the same as a well-positioned business. The critical question is not merely, “What information do we have?” It is, “How do we present this company in a way that supports its value while addressing risk before the buyer uses it as leverage?” Experienced deal counsel can strategically determine which issues should be resolved before going to market, how diligence should be sequenced, and how disclosures should be framed accurately without creating unnecessary exposure. The headline price is only the beginning Every seller wants the highest possible purchase price. But the stated price in a letter of intent or purchase agreement does not always equal what the seller receives at closing or what will remain after the deal is complete. Diligence findings can trigger price reductions, working capital adjustments can move significant dollars after closing, earnouts can make a portion of the sale dependent on future performance and buyer-controlled decisions, and escrows and holdbacks can delay access to proceeds. While AI may be able to flag these provisions or compare them with language found in other agreements, it is critical to have an understanding as to how the provisions interact and how they affect this seller's actual economics. A working capital definition that appears ordinary may exclude an item that is central to the business. An earnout metric may sound objective but become difficult to achieve after the buyer integrates the company. A seemingly modest indemnity can become costly if it is paired with broad representations, a long survival period, and an inadequate liability cap. Experienced counsel is trained to look beyond whether a term is simply present. They evaluate how it operates, where it shifts leverage, and whether it is consistent with the commercial bargain the seller believes it made. AI cannot negotiate post-closing liability For many sellers, the provisions governing post-closing exposure are among the most consequential parts of the transaction. The sale price loses some of its meaning if too much remains subject to claims, repayment obligations, or disputes long after closing. Controlling that exposure requires negotiation, not just identifying standard clauses. Deal counsel works to narrow representations and warranties, limit indemnification obligations, reduce escrow or holdback amounts, establish appropriate liability caps and baskets, define exclusions carefully, and shorten survival periods where the circumstances support it. Counsel also considers how those protections fit together. Winning a lower cap may offer little comfort if a broad exception effectively swallows it. A shorter survival period may not solve the problem if the most significant representations remain outside that limit. This is where experience directly impacts the economics of a deal. A lawyer who has seen claims arise under similar language can anticipate how a provision may be used when the parties no longer share the optimism of signing day. AI analyzes text. It does not advocate for the seller, read the negotiating dynamics, or make the tradeoffs required to bring the parties to agreement. A technically correct answer may still be the wrong deal decision M&A negotiations are filled with decisions that do not have a single correct answer. Should the seller resist a buyer's request or conserve leverage for a more important issue? Should a potential concern be disclosed now, investigated further, or addressed through a specific contractual solution? Is a provision worth extending the negotiation, or is accepting it the better choice given the buyer, the timing, and the seller's objectives? Coming to the right answer requires understanding context. It may turn on the strength of the buyer's alternatives, the seller's tolerance for delay, the likelihood that the issue will create real exposure, and the relative value of other concessions under discussion. It also requires an understanding of the personalities at the table and how aggressively a point can be pressed without jeopardizing the deal. That judgment is built through experience and cannot be generated from contract language alone. Overreliance on AI can create new risks The efficiency of AI can create a false sense of completeness. A seller may assume that an AI-generated contract summary captured every material obligation or that an automated diligence review identified every inconsistency. But incomplete context, ambiguous drafting, poor source documents, or a seemingly minor error can lead to inaccurate disclosures, missed consent requirements, incomplete diligence responses, and post-closing disputes. Confidentiality, data security and the handling of privileged information also require careful attention when AI tools are used in a transaction. The responsibility for the deal lies with the parties and their advisors, not the technology. They remain accountable for the accuracy of disclosures, the completeness of responses, and the meaning of the documents they sign. AI output should therefore be treated as a work product to validate, never something to accept without review. Use AI to support the deal team, not substitute for it Sellers should take advantage of AI tools that make transactions more efficient and allow for better organization, faster review, and earlier identification of potential issues. But the strongest approach is to use those tools under the direction of experienced advisors who understand what matters, can test the output, and know how to convert information into strategy.
October 5, 2026
Mergers and Acquisitions
Can AI Buy a Company? What Buyers Need to Know About AI’s Role and Limitations in M&A Transactions
Artificial intelligence is changing just about everything in our lives, including the merger and acquisition (M&A) process. AI-powered tools can add tremendous efficiency to the acquisition process by reviewing large volumes of documents, summarizing contracts, organizing diligence materials, and identifying provisions that might otherwise take hours to find. While these efficiencies can accelerate the M&A process, speed should not be mistaken for judgment. An acquisition is not just about collecting and summarizing information. Buyers must determine what that information means for the value of the business, the structure of the transaction, and their willingness to proceed. AI can be a very helpful tool, but it cannot replace the wisdom and judgment that comes with experienced M&A counsel. The better question is not whether AI can buy a company. It is how buyers and their advisors can effectively use AI tools without losing sight of the human judgment that ultimately protects the deal. AI Can Review Documents, But It Cannot Assess the Buyer’s Risk During due diligence, AI tools can be very useful in taking over time consuming tasks such as: Summarizing contracts Locating change-of-control or assignment provisions Comparing similar agreements Flagging unusual or inconsistent terms Organizing documents by subject matter Identifying potentially missing information AI’s speed here is particularly helpful in transactions involving hundreds or thousands of contracts. That said, identifying a provision is only the beginning of the analysis. Suppose an AI tool finds change-of-control language in several agreements. The real questions are: Which agreements are critical to the business? Will consent be required before closing? Could the counterparty terminate or renegotiate? How would the loss of that relationship affect revenue, operations, or valuation? The same language can create very different levels of risk depending on whether it appears in a minor vendor agreement or a contract with the target’s largest customer. AI may locate the provision, but it cannot reliably determine how much risk it creates for this particular buyer in this particular transaction. That requires a human’s understanding of the buyer’s objectives, the target’s business, the industry, and the broader structure of the deal. AI Finds Issues, But Lawyers Determine Materiality Due diligence often produces a long list of potential concerns, including incomplete employment agreements, gaps in intellectual property ownership, inconsistent customer contracts, regulatory deficiencies, or unresolved disputes. AI can help identify these issues, but it can also identify so many potential concerns that the buyer ends up with more information than clarity. This is where experienced deal counsel can help the buyer separate meaningful risks from background noise. Not every issue warrants the same response, and many times, matters can be corrected before closing. Others may justify a purchase-price adjustment, escrow, or holdback. Certain risks may require a special indemnity, a closing condition or a change to the transaction structure. A sufficiently serious issue may cause the buyer to reconsider the deal altogether. But that kind of analysis depends on context, and determining how the pieces fit together remains a judgment-intensive exercise. AI Does Not Negotiate the Deal Every acquisition involves compromise. Even when the parties agree on price, they must negotiate representations and warranties, indemnification obligations, liability caps, escrows, closing conditions, earnouts, and numerous other provisions that allocate risk between the buyer and seller. AI can propose language based on prior agreements or common market formulations. It may also help compare drafts and identify changes. But it is critical to note that it cannot be entrusted to manage the negotiation itself. That requires an understanding of what the other side wants, where the buyer has leverage, and which issues are worth pressing. It also requires the ability to recognize when a proposed solution creates a new problem elsewhere in the agreement. Sometimes the strongest response is to hold firm. Other times, the better strategy is to address the concern through a price adjustment, special indemnity, post-closing covenant or alternative structure. A good deal lawyer does more than argue over language. They help the parties find a workable path to closing while protecting the client’s most important interests. There is also a strong relationship component to every transaction. Many buyers need the seller, management team, or key employees to remain involved after closing, but an unnecessarily aggressive negotiation can damage the working relationship before the buyer takes control of the company. AI cannot read the room, understand personalities, or know when winning a drafting point could hurt the larger transaction. AI Cannot Identify Every Question the Buyer Should Be Asking AI is generally most effective when it has the right documents and receives the right inputs and instructions. The difficulty is that buyers do not always know what is missing, or even what they should be asking in the first place. Experienced M&A counsel can recognize patterns from prior transactions. They know which diligence requests are likely to uncover problems, which industries present specialized risks, and which seemingly routine answers require follow-up. A contract summary will not help if a significant agreement was never uploaded to the data room. A review of the target’s intellectual property schedule may not reveal that a former contractor created critical software without signing an assignment. Employment records may look complete until someone asks how workers are classified, compensated, or managed in practice. AI analyzes only the information it receives; whereas deal counsel knows when the available information does not tell the entire story. This ability to identify the unknown is particularly important for buyers entering a new industry or making their first acquisition. An experienced attorney can anticipate where issues tend to arise and tailor the diligence process to the buyer, the target, and the transaction. AI Outputs Still Need to Be Verified AI-generated summaries can sound authoritative even when they are incomplete or incorrect. A tool may overlook an exception, misinterpret a defined term, miss the interaction between multiple provisions, or reach a legal conclusion that the underlying language does not support. In an M&A transaction, even a small error can have significant consequences. A missed consent requirement could delay closing. An incomplete summary of a customer agreement could distort the buyer’s view of recurring revenue. A mistaken interpretation of an indemnification provision could leave the buyer with less protection than expected. AI should be treated as an analytical tool, not as the final reviewer or decision-maker. Its work must be checked against the underlying documents and evaluated by professionals who understand the legal and business consequences. Buyers and their counsel must also consider how sensitive deal information is handled. Confidential financial records, customer data, employee information, and trade secrets should not be entered into an AI platform without understanding the tool’s security, retention, and privacy practices. Using AI the Right Way in an Acquisition The strongest acquisition teams will not ignore AI, but importantly, they will not treat it as a substitute for experienced advisors. AI is most valuable when it handles repetitive, time-intensive tasks and allows deal counsel to spend more time on higher-value work. Buyers should have a firm understanding of: Which AI tools their advisors are using How confidential information is protected Whether AI-generated findings are independently verified How identified issues are prioritized and escalated Which decisions remain subject to human legal and business judgment The goal in using these tools to help deal teams ask better questions, find issues sooner, and make better-informed decisions. AI may help a buyer move through diligence more efficiently, but it cannot decide whether a risk is acceptable, negotiate the right protection, or determine whether the deal still makes strategic sense. Those decisions will always require the experience, context, and judgment legal counsel and advisors bring to the table.
September 8, 2026
Mergers and Acquisitions
The Earnout Trap: Hidden Post-Closing Risks in M&A Transactions
Earnouts are often presented as a solution that can help get a deal across the finish line. If a buyer and seller disagree on valuation, an earnout can help bridge that gap by tying a portion of the purchase price to the future performance of the company post-closing. It’s a simple concept in theory. If the company performs as expected, the seller will receive additional payments. If the company does not meet the established metrics, the buyer pays less. However, in practice, earnouts can introduce a significant layer of complexity, and they are one of the most heavily litigated provisions in M&A transactions. Why does this happen? Because after closing, the seller is no longer in control of the business – something that is often seriously underestimated during negotiations. Founders generally have a belief that the company they created and built is poised for substantial growth. And while that might have been true pre-sale, once there is an ownership transfer, things can change significantly. The seller no longer has the ability to make decisions to achieve growth targets. Hiring decisions, sales strategy, marketing budgets, staffing levels, pricing models, operational priorities, and integration efforts are all solely in the hands of the buyer once the deal is done. To further complicate matters, the acquired company may be integrated into a larger platform business or combined with another portfolio company. Revenue streams may be reallocated, expenses may be shifted, and key employees may choose to leave. Long-term integration might also be a higher priority for the buyer as opposed to short-term profitability. Each of these decisions can directly impact whether earnout metrics are achieved. And this is where disputes arise. Sellers must carefully negotiate earnout provisions to avoid losses or even the courtroom down the road. Establishing Clear Standards One of the biggest mistakes sellers make when negotiating earnouts is agreeing to vague or subjective standards. The more discretion the buyer has post-closing, the greater risk to the seller that they will never receive their full earnout payment. This is why sellers should work with legal counsel to establish objective, clearly measurable performance metrics. For example, revenue-based earnouts are typically easier to evaluate than EBITDA or profitability metrics because profit calculations can be heavily influenced by post-closing decisions. And even the most straightforward revenue metrics need to be carefully drafted. Sellers must understand exactly what counts toward the target, how revenue is recognized, whether certain contracts are excluded, and how deferred or recurring revenue will be treated. Properly Structuring Earnouts The structure of earnouts also matters, because when these are not structured properly, a seller could forfeit millions in earnout consideration if targets are barely missed. Therefore, the following provisions must be heavily negotiated or there can be a dramatic sway in the ultimate economics of the transaction: Is the earnout all or nothing? Will missing the target by a small margin result in no payment at all? Is there a sliding scale that allows for partial payments if performance reaches certain thresholds? If the company exceeds projections, does the seller benefit from that upside? Post-Closing Information and Enforcement Rights Another critical factor to consider are the seller’s post-closing information and enforcement rights. Sellers should negotiate their access to financial information, reporting obligations, audit rights, and dispute resolution procedures before signing any deal documents. Without having these kinds of protections in place, it becomes increasingly difficult to determine whether a buyer appropriately calculated the earnout or if operational decisions unfairly impacted performance. The Broader Financial Risk It is common for sellers to underestimate the broader financial risk that is tied to variable consideration structures such as earnouts and rollover equity. These can be extremely valuable tools in the right transaction, but they also shift risk back to the seller. The more price is tied to future performance, the less certainty the seller has regarding their proceeds from the sale. This is why legal counsel and deal advisors encourage sellers to limit the percentage of total deal value that is tied to earnouts whenever possible. Cash at closing equals certainty. While earnouts can provide an upside, they can also establish a continued dependency on a business that the seller no longer controls. These risks do not mean earnouts should be avoided in every situation. They do have value in their ability to bridge valuation gaps, align incentives, and move deals forward that otherwise would have stalled out. But sellers must approach earnouts with caution and a clear understanding of these risks. In M&A transactions, much of the important negotiations center on the purchase price. But remember, the most important disputes occur post-closing, with earnouts being at the center of them. Negotiate earnouts wisely.
August 3, 2026
Mergers and Acquisitions
Breaking Down Rollover Equity: Why Buyers Love It and What Sellers Need to Know
For many business owners, the goal of selling their company is turning their years, and often decades, of hard work into liquidity. But in some cases, retaining a stake in the company could prove to be fruitful for both the buyer and the seller. That is where rollover equity comes into play. Below is a breakdown of the benefits and risks of rollover equity, and what sellers need to know. Rollover Equity Explained The concept of rollover equity is simple. Instead of paying a seller entirely in cash, a buyer acquires 100% of the target company while allowing founders and key shareholders to retain a stake in the new ownership structure. The seller still receives some immediate liquidity at closing, exchanging the remaining portion for equity in the post-transaction business. This is certainly not a new concept and has been common in private equity transactions for some time. However, it is becoming an increasingly important tool today as buyers and sellers work to bridge valuation gaps and align their incentives in today’s more cautious deal environment. The Benefits of Rollover Equity One of the most obvious benefits of this deal structure is that it reduces the amount of cash required to close a transaction. This is a significant benefit for buyers who are motivated to preserve capital whenever possible, particularly in today’s market when financing costs are elevated, and lenders are scrutinizing leverage more carefully. Buyers do not have to fully fund a transaction with cash, but they still obtain full control of the entire company. Additionally, when founders remain involved, there is an increased confidence that the management team and employees will remain motivated and stay onboard. Continued seller participation can also help to preserve relationships, maintain operational continuity, and retain institutional knowledge after the deal closes. These non-economic factors can be critical to the company’s future success. Rollover equity can also be a tool to bridge valuation disagreements between a buyer and seller. A frequent issue that arises is a seller’s belief their business deserves a higher valuation based on its growth potential vs. the buyer’s hesitation to fully underwrite those projections in cash. A rollover structure provides a bridge for both sides to move forward despite the disconnect on valuation. The seller gets to walk away with immediate liquidity while still retaining the opportunity to benefit from the upside if the company continues to grow. That second bite at the apple can prove to be extremely valuable for a seller if the company later sells at a higher valuation. They can see returns that far exceed anything they would have generated from an all-cash transaction up front. This makes rollover equity particularly attractive for sophisticated sellers who see the opportunity to continue participating in value creation alongside the buyer. The Risks of Rollover Equity While there are many upsides to rollover equity, it is not without risk. Most importantly, sellers must fully understand what they are receiving in exchange for the portion of the sale they are not receiving in cash. The rolled equity is typically a minority stake in a buyer-controlled entity. The seller will have minimal control over future decisions, including exit timing. Therefore, the rights associated with the rollover are incredibly important and should be carefully negotiated. Rollover equity can also include some restrictions for the seller. For example, there can be mandatory hold periods, drag-along provisions, or other limitations that can affect how and when the seller can monetize their investment. The capital structure of the post-closing entity also matters. If the new entity is highly leveraged, the seller may face a very different set of risks than they did as the original owner. As with any transaction structure, a rollover transaction comes with its own set of tax considerations as well. When structured properly, rollover equity can come with the added benefit of tax deferral in certain instances for sellers, but the rules here are complex and highly dependent on deal structure. It is essential to bring in legal and tax counsel early on to ensure everything is structured appropriately and aligns with the seller’s financial goals. Rollover equity can be a highly beneficial tool for both buyers and sellers, and it will no doubt continue to be increasingly used in today’s M&A environment. But there are many considerations, especially on the sell side, that must be addressed from the start. Working with effective legal counsel throughout the process can help to reduce the risk, increase the benefits, and set up sellers for even greater success in the future.
July 6, 2026
Mergers and Acquisitions
When the Deal Gets Personal: The Emotional Inflection Points of Selling a Business
Selling a business is largely viewed as a financial transaction shaped by valuation, structure, diligence, and closing. However, for founders and owners, selling a business is also an emotional journey that can be a highly stressful event. That stress can be compounded when a corporate attorney is brought in late in the process when many sellers have already experienced the early and most precarious stages of the deal. Many sellers work with an investment banker to take the company to market, vet buyers, and there may even be a letter of intent (LOI) on the table before an attorney is brought on board. While the seller feels they are making progress, from a legal and strategic standpoint, this early stage is where complexity and stress begin to escalate and legal counsel is critical. We have discussed the importance of bringing in legal counsel early in the process in multiple posts, and that cannot be emphasized enough. Below, we examine the most stressful components for sellers in any deal and how bringing in legal counsel early can help to ease the burden. Letter of Intent The LOI is one of the earliest inflection points in the deal process. Sellers often underestimate its significance because they see it as non-binding on economic terms. But this is a false sense of flexibility because exclusivity and time restrictions are binding. Once that LOI is signed, the seller is essentially off the market for a determined period and cannot engage in discussions with other interested buyers. This is where leverage begins to shift from the seller to the buyer. The buyer now has two things that are very valuable: time and access. On the other side, the seller is now increasingly invested, both financially and emotionally, in making the deal happen. It is now harder for the seller to walk away from the deal, even if circumstances change. Diligence The leverage shift becomes more pronounced when the deal enters the diligence stage. Buyers are highly disciplined as they approach this phase of the transaction, particularly when they are sophisticated financial sponsors. Diligence is not about buyers just confirming what they have been told, but rather testing assumptions, looking for weaknesses, and then recalibrating valuation based on their findings. It is common for buyers to reassess price or deal structure because of what is uncovered during diligence, and for sellers who entered the process with a clear expectation of value, that can be jarring. The business they have spent years or even decades building is now being evaluated through a different lens. Consistent Performance Another layer that multiplies the pressure on the seller is the expectation that the business continues to perform at the same level throughout the entire process. Entering negotiations to sell does not equate to a pause in operations. It is simply a process that runs parallel to day-to-day operations. Sellers must manage diligence requests, respond to buyer questions, and engage with all their advisors, all while effectively running the company. They cannot afford for performance to dip, even for reasons that have nothing to do with the transaction. That can lead to a reason for renegotiation, with buyers adjusting terms, implementing additional protections, or even revisiting the valuation entirely. This creates constant tension for the seller who is trying to execute the deal and simultaneously maintain the underlying business. Delayed Engagement of Legal Counsel When a seller brings in legal counsel later in the transaction, it can feel disruptive at first. This is because the job of an attorney is to identify and address risks, clarify what has already been agreed to, and ensure that the documents accurately reflect the intended deal. If they are not involved from the jump, they may have to revisit assumptions or unwind understandings that developed earlier in the process. This can feel like friction or a change in direction for sellers, and that can be avoided when counsel is engaged from the start. The issues become even greater when the buyer is a private equity (PE) firm. These repeat players operate with well-established playbooks and experienced deal teams. This is in stark contrast to a first-time seller who sees this as a once in a lifetime event. For a PE firm, this is just a routine transaction. The imbalance this creates can heighten the emotional stakes, particularly when discussing complex deal components. The Personal Dimension The personal dimension of the deal overlays everything. For a seller, their business represents years of work, relationships, and their identity. Their company is not just an asset they are selling; it is often their life’s work. Layer in concerns about their employees, customers, and their legacy, and the personal connection to the business complicates everything. Sellers often carry the weight of the transaction on their own, while they must continue to lead their company, One other very important reality for sellers is that the deal is not done until it is closed. It is easy to get excited and assume that signing an LOI or moving through the diligence process means the outcome is assured. But the truth is that transactions can, and do, change late in the process. Terms evolve, issues emerge, and sometimes, deals fall apart. It is critical to maintain perspective and discipline and attempt to put emotions to the side. The bottom line for sellers is that every transaction must be approached with preparation and support from the start to minimize the significant stress that comes with every stage. Bringing in skilled legal counsel very early in the process can alleviate that stress and help sellers to not only maximize value, but also bring clarity to the many complexities of a sale, resulting in a deal that truly reflects the seller’s goals.
June 1, 2026
Mergers and Acquisitions
First Time Buyers: Avoiding Analysis Paralysis
For first time buyers, the diligence phase of an acquisition can be overwhelming. Every document review, identified risk, and unanswered question, can lead to hesitation, and hesitation can quickly turn into something known as “analysis paralysis.” This can be a dangerous place for a transaction as it leads to a loss of momentum or even loss of the deal entirely. It is important for first time buyers to understand that no deal is without risk. You cannot eliminate risk entirely, but you can understand it, quantify it, and allocate it appropriately. When first time buyers recognize this reality early in the process, they are far more likely to move through the diligence process with confidence and ultimately have a successful closing. Below we look at some of the ways first time buyers can help to avoid analysis paralysis and build in the kind of protections that will allow them to move forward with ease. Bring in Advisors Early One frequent error among first-time buyers is delaying the engagement of experienced advisors, especially legal counsel. Legal counsel should be involved before the Letter of Intent (LOI) is signed, as their early participation enables the deal team to identify key issues, recognize potential risks, and structure the transaction to align price with risk effectively. Early involvement of advisors ensures that, upon reaching the diligence stage, the team is prepared to execute a strategy that has been thoughtfully designed from the outset, rather than developing one mid-process. Shifting Risks To allocate certain risks from the purchaser to the seller, it is essential to include precise representations and warranties, along with unambiguous indemnification clauses. When concerns arise, such as outstanding liabilities or matters identified during due diligence, targeted indemnities can significantly strengthen the buyer's protection. These safeguards enable buyers to move forward with a transaction even when not every issue has been conclusively resolved. Financial Structuring The financial structure of a transaction is equally significant as the inclusion of contractual safeguards. Transactions may be designed to incorporate financial protections for the buyer, such as escrow arrangements, holdbacks, or promissory notes. Additionally, earnouts provide further protection, particularly in situations where future company performance remains uncertain. By linking a portion of the purchase price to post-closing results, buyers can mitigate the risk of overpayment while enabling sellers to realize their preferred valuation. Deal Momentum One of the most important considerations for first time buyers is maintaining deal momentum. Conditions can shift quickly as transactions progress from market conditions to financing terms to business performance. If the diligence process is stalled, it allows more time for these conditions to shift, often leading to increased risk or erosion in value. When sellers lose confidence in the transaction, they could begin to entertain a competitor’s bid. Shifting conditions could also lead to a need for price adjustments or renegotiation of other terms. This is exactly where advisors prove invaluable. They can help buyers to distinguish between those issues that need immediate attention and are true red flags, as opposed to those that can be addressed through deal structure. Advisors can instill the kind of confidence in first time buyers that allows deals to move forward, even if every variable is not perfectly resolved. For those buyers entering the M&A process for the first time, the key is not to avoid risk, but to manage it intelligently. With the right team and a disciplined approach to maintaining momentum, buyers can avoid analysis paralysis and position themselves for a successful closing.
May 4, 2026
Mergers and Acquisitions
Financial Readiness: Fixing the Problems Before Going to Market
When a business owner is considering a sale, financial statements are often the first point of contact with a potential buyer. Before any discussions commence regarding strategy, growth potential, or culture, buyers are going to ask the question, “Can we see your financials?” Your financials tell the story of your business. When they are clear, credible, and well-prepared, they create momentum and instill confidence in the buyer. But when they are inconsistent, unclear, or require significant explanation, the transaction may stall or halt before it ever really started. Or it could result in an offer that doesn’t meet the seller’s expectations. Carefully prepared financials are critical to any transaction, and this must be handled before entering the market. It is one of the most important steps a seller can take to protect valuation and keep the deal on track. The First Test for Buyers When reviewing a potential acquisition, buyers are going to first evaluate two fundamental issues: the historical earnings of the business and its future earning potential. The historical performance is the foundation for determining valuation. This means the financial statements must clearly demonstrate profitability and reliable cash flow. When there is uncertainty, it can translate into a discounted offer or a decision to walk away. Sometimes the issue is not that a business is underperforming, it is just that their financial statements are not clearly reflecting the true earning power of the business. Addressing “Add-Backs” It is common for many privately held businesses to run a variety of expenses through the company that are not directly tied to operations. When this happens, it can distort the financial picture if these are not identified and adjusted. This can include personal expenses that are run through the business, vehicles or travel not tied to operations, above-market owner salaries, compensation to family members that are not active in the business, and more. When preparing for a sale, these kinds of expenses will typically be “added back” to EBITDA to reflect the company’s normalized operating performance. When add-backs are properly documented, it can significantly improve the evaluation of the business. But they must be adjustments that are credible and clearly supported, or it can lead to additional concerns and a slower negotiation process. Quality of Earnings Reports Within the past few years, Quality of Earnings (QoE) reports have become increasingly common early in the process to review the company’s financial performance. Sellers are now commissioning these reports before entering a sale process as opposed to a buyer conducting this analysis during the due diligence process. Because an independent accounting firm is conducting the analysis, it lends a level of third-party legitimacy and validation to the company’s earnings profile. This serves to further reduce uncertainty and can help accelerate the process overall. It can also help to instill confidence for the buyer that can lead to stronger initial offers. Preparation is Key in Today’s Market We have noted in previous posts looking at the current M&A climate that today’s buyers are more disciplined than ever. They are focused on financial clarity and risk management, and they are spending more time evaluating every aspect of a target’s financials. When a seller enters the market with well-prepared financial statements, along with supporting analysis from a third-party, they are often able to move through the diligence process more efficiently and have even greater leverage in negotiations. It is more important than ever to engage legal and financial advisors very early in the process. This allows ample time to clean up financial statements, resolve inconsistencies, identify areas of adjustment, and prepare supporting documentation. Presenting these kinds of financials that clearly demonstrate historical performance, and future potential allows buyers to justify a higher valuation. Part of every transaction is storytelling, and your financials must tell a credible story for buyers to have confidence in where the business has been and where it is going. Addressing any issues early in the process, well before going to market, is going to help eliminate surprises and strengthen the position of the seller. This is key to positioning the company for a successful transaction.
April 6, 2026
Mergers and Acquisitions
Preparing to Sell: The Most Common Deal-Killing Mistakes Business Owners Make, and How to Avoid Them
For many middle-market business owners, 2026 could present an ideal window to explore a sale. With financing markets improved and private equity (PE) sitting on significant amounts of dry powder, strategic buyers are in a prime position to pursue acquisitions that offer them growth and efficiency. Smart sellers will be prepared to take advantage of these improved conditions and strike while the iron is hot. But even in healthy deal environments, deals can fall apart, and most of these failures are preventable. As a corporate M&A attorney, what I typically see are the same avoidable issues that derail transactions. Below, we look at the most common mistakes business owners make before going to market and most importantly, how to avoid them. Sloppy or Unvetted Financials An easy way to erode buyer confidence is to present unreliable financials. Buyers expect clean financial statements, normalized EBITDA with clearly supportable add-backs, transparent revenue recognition policies, and thorough documentation. This requires significant preparation and engagement of advisors early in the process (at least 12 to 24 months before a contemplated sale). Taking the time to get your financials in order can help reduce friction, prevent re-trades, and ultimately protect your company’s valuation. Failure to Clean Up Your House Failure to clean your corporate house before going to market is a very common mistake owners make. Before engaging in any sale process, sellers should take a critical look at everything in the business, making sure it is all in order. This includes ensuring customer contracts are in writing, properly assignable, and free of any change of control termination rights that can present problems. Vendor agreements should also be scrutinized, making sure they clearly document pricing terms and are commercially sustainable. Do your debt structures contain restrictive covenants? And are your equity records and governing documents accurate and up to date? Is your intellectual property ownership properly documented? A deep dive into all of this and more is critical. Buyers do not like surprises in the diligence process. Further, having to “clean-up” the business in front of the buyer can cost credibility as well as deal value. Conducting a thorough pre-sale legal audit can help eliminate surprises as well as the costly delays (or worse). Limiting the Potential Universe of Buyers Assuming you already know your ideal buyer can be a major mistake. Many owners assume they will sell to a competitor or a PE firm, but the universe of buyers in 2026 is much larger. Limiting yourself to only certain types of buyers can materially depress value. Today’s buyers span strategic acquirers seeking bolt-on growth, family offices in search of long-term cash flow, international buyers looking to enter the US market, and more. To ensure you are maximizing your valuation and considering all options, there must be a broad, well-run process to vet buyers. This will increase competitive tension, which in turn, drives up the price and lays the groundwork for better deal terms. Overlooking Tax Structuring Tax structuring is not an afterthought. It must be a part of the strategy. After all, taxes drive transactions. How your transaction is structured matters. Whether it is an asset sale, stock sale, rollover equity arrangement, or partial liquidity event, it can materially impact net proceeds. Therefore, it is important to coordinate early with both legal and tax advisors who can dramatically change the “after-tax” outcome of your transaction. That is the number that truly matters. The Owner is the Business There are some red flags that buyers look for in an acquisition in relation to the owner and their role within the organization: Is the owner the primary salesperson? Are they the sole keeper of customer relationships? Are they the only decision maker? Without the owner, does the organization run into an operational bottleneck? If the answer is yes to these questions, then you do not have a truly transferable business. This creates a real issue for buyers, as they discount businesses that rely entirely on a founder. They want systems and processes in place, depth of management, and a company that can exist without its owner. Start working early to develop a solid management team, formalized processes, and institutionalized customer relationships to decrease risk and increase value. Failure to Incentivize Key Employees When key employees start to feel uncertain or that they are unprotected, it can negatively impact a transaction. Employees want some clarity, and buyers are looking for continuity. That means you must plan and communicate regularly and effectively. Retention plans, bonuses tied to the transaction, or equity offers are all incentives that can help preserve stability during and after the close. Failure to Plan Ahead Selling a business is a major financial event, but it is also a significant life transition. Most owners have spent years, if not decades, building their business, and it has become a part of their identity. So, it is surprising that they don’t often consider the role they will play (if any) with the company moving forward. Nor do they consider what’s next. What lies beyond the day after the sale? These might seem like afterthoughts, but they are not. They must be considered upfront so that expectations with the buyer are clearly communicated and there is no tension or dissatisfaction on either end. Waiting Too Long to Involve Advisors If you wait too long to involve your legal and financial advisors, you may have already lost your leverage. You cannot wait until you have received an unsolicited offer. Involving advisors early in the process is the key to success and to avoiding the mistakes we have discussed. Reach out to your advisors 12-24 months before considering a sale so that you can address any issues and ensure preparedness. By engaging experts early on, you are shortening diligence timelines and strengthening your negotiating position. And remember, valuation can be significantly eroded by avoidable preparation failures. Prepare your business, and yourself, for the outcome you want.
March 2, 2026
Business
Rethinking the Early Exit: How Gen X and Millennial Owners Are Selling Smarter in 2026
While much of the exit-planning conversation has centered on Baby Boomers approaching retirement, Millennial and Gen X founders are also a growing segment of today’s middle-market sellers. These generations collectively own a large portion of small and middle-market businesses, and they often do not hold on to their businesses as long as previous generations, prioritizing exits at a stage when they can still pivot to new ventures. This means that earlier-in-career exits are becoming increasingly common, and they present a distinct set of considerations for these younger generations, particularly for those looking to make a move in 2026. Market Conditions in 2026 Starting in 2025, we began to see a much more active merger & acquisition (M&A) market than we have the past few years, and that is expected to continue as we move through 2026. Strategic buyers remain active, private equity firms continue to deploy record levels of dry powder, and financing conditions (particularly in private credit) have improved. At the same time, buyers remain disciplined, and valuations favor businesses with predictable cash flow, strong management teams, and scalable operations, even where growth remains the primary story. For younger founders, this kind of dynamic can cut both ways. Many younger companies are still scaling, reinvesting, or professionalizing operations, which can limit valuation if pursued too early. Therefore, one of the most critical drivers of outcome this year is timing the market, while also allowing the business to mature operationally. The Impact of Boomer Sales on Timing and Valuation It is important for Gen X and Millennial business owners to note that right now, there are many Boomer-owned businesses that are coming to market. While this wave of Boomer business sales is fueling buyer interest, it does present another layer of complexity for younger sellers. Unlike legacy businesses with decades of operating history, companies owned by Gen X or Millennials may lack the same kinds of long-term financial track records. While buyers in 2026 are still willing to underwrite growth, they are going to expect clean financials, recurring revenue, and evidence that performance is durable, not founder dependent. This is why strategic exit planning, often beginning 12 to 24 months before a sale, can materially improve valuation by allowing time to normalize earnings, strengthen leadership, and reduce execution risk. Market cycles and competitive sale dynamics also matter, particularly as so many Boomers will be selling over the next few years. Choosing the Right Deal Structure for Long-Term Wealth Younger sellers typically have decades of professional life ahead of them, making deal structure equally as important as price. Partial liquidity events, rollover equity, earn-outs, and minority recapitalizations remain common in 2026, particularly in private equity transactions. Remember that the structure you choose will have significant tax, risk, and governance implications and should be addressed early with experienced legal and financial advisors. This will all impact your long-term wealth, so choosing wisely here is critical. Gen X and Millennials are certainly taking a different approach to business ownership and exit timing than earlier generations, opting for exits earlier in life that afford them flexibility and opportunity. While there can be incredible benefits to these early exits, in today’s competitive and disciplined M&A environment, younger owners must think beyond valuation alone, considering timing, structure, and how each decision will impact their long-term wealth. Ultimately, a successful exit for today’s younger business owners is not defined by the sale itself, but by how deliberately it positions them for sustained financial security, future ventures, and the next chapter of their professional lives.
January 30, 2026
Mergers and Acquisitions
Preparing for a Sale in 2026: What Retiring Business Owners Need to Know
As we begin 2026, we find ourselves right in the middle of “Peak 65,” the period of time between 2024 and 2027 when approximately 4.1 million Americans will turn 65 each year. Also known as the “gray tsunami,” this powerful demographic shift has profound implications for closely held and family-owned businesses. For many of these business owners finding themselves at retirement age, 2026 will be a pivotal year, particularly for those who want to exit on their own terms through a sale. We previously examined this issue in 2025, but as the next round of business owners look at a potential sale in 2026, it’s time to revisit the issue and some of the specific considerations for sellers this year. Market Timing and Buyer Behavior In 2026, buyers are still disciplined. They will pay for quality, predictability, and growth, but they will penalize uncertainty. This means it is important to position the business as “recession-resilient,” showing recurring revenue, diversified customers, and stable margins. Sellers should also avoid sending a signal of urgency. Many buyers view a retirement-driven sale as a “must sell.” This can weaken the leverage on the seller’s side. In 2026, sellers should also anticipate longer diligence and tougher deal terms, especially if your house is not in order. Financial Readiness Having strong, clean financials is the single biggest value driver. 2026 buyers are going to heavily scrutinize everything from the last 24-36 months of financials to working capital trends to cash flow vs. EBITDA. This means it is important that your financials tell a clean story. Look carefully at issues such as owner compensation, what family is on the payroll, personal expenses, and one-time expenses. Remember that buyers will discount anything that is unclear or that you must overly explain. If it takes more than 30 seconds to explain an adjustment, you can likely expect pushback. Owner Dependence and Transition It is important to understand that buyers are not buying you. They want to buy a business that works without you. They will be looking for red flags such as too much control over key customer relationships or pricing, hiring or spending. If the owner is the only one who really “knows how things work,” it doesn’t instill confidence in the future of the business. Make sure you are delegating customer relationships, creating formal processes for pricing, approvals, and reporting, and identifying or elevating a second in charge or leadership team that can carry the torch moving forward. You should also document key processes and procedures so that there is a clear roadmap once you exit. Deal Terms In 2026, deal terms are going to be just as important as the headline price. Many sellers are focused just on the price, but they will regret the deal terms down the road. This year, buyers will be focused on terms such as earnouts tied to performance, seller notes, escrows and indemnity exposure, and post-closure employment or consulting obligations. Before you decide to sell, you must determine how long you are willing to stay involved, as well as what level of risk you’re willing to tolerate after the close. Are you looking for certainty or are you looking for upside? The more clarity you have on these issues going into negotiations, the less likely you are to make an emotional decision you will regret later. Family Dynamics One often overlooked issue that sellers do not consider is the dynamics of the family within the business. Emotional risk is viewed as financial risk, and this can be tricky when a family business comes up for sale. Do you intend for any children or relatives to stay on with the business? Is everyone aligned on value and timing? And what kind of family perks are embedded in the business? All of these are vital questions to answer well ahead of a sale. 2026 buyers will move away from uncertainty around family involvement or adjust the price accordingly. Looking Ahead For retiring business owners, selling a company is one of the most consequential transactions of their lives. In the context of the gray tsunami and an increasingly active middle-market M&A environment, 2026 is filled with opportunities as well as risks. With thoughtful preparation, it is possible not only to maximize value, but also to protect the legacy built over decades and transition into the next chapter on favorable terms.
January 6, 2026
Business
Middle-Market M&A at the Close of 2025: What Business Owners Should Expect in 2026
As 2025 ends, the merger and acquisition (M&A) market, especially in the $5–$100M deal range, is closing out the year on firmer footing than it began. After two years defined by higher borrowing costs, valuation gaps, and cautious buyers, the middle market spent 2025 recalibrating. Today, we’re seeing disciplined but real momentum. There is better alignment between buyers and sellers, renewed lender appetite, and a more predictable rate environment that is finally allowing exit windows to open. Heading into 2026, small and mid-sized business owners should feel cautiously optimistic. Deals are getting done, but strong fundamentals matter more than ever. Below is a year-end look at the data, the trends, and the opportunities for middle-market deals. Deal Volume For transactions involving PE firms, deal volume appears to be on the rise in late 2025. According to a report from EY, while deal value was down for PE deals in October, deal volume in this area was up, indicating a move to more mid-market and smaller transactions for PE firms as opposed to mega deals. In terms of the overall picture for the M&A market, Deloitte’s 2026 M&A Trends Survey signals that while total deal value rose 56% in Q3, total deal volume only jumped 1.6%. They say this could “present an opportunity for increased value realization, especially with midmarket and smaller deals.” Valuation Gaps EY’s Private Equity Pulse from Q3 of this year also points to a narrowing valuation gap between buyers and sellers. In their most recent global general partner (GP) survey, two-thirds of respondents cite a narrowing valuation gap that is allowing “buyers and sellers to find common ground and move forward with confidence.” So, what is driving this gap to close? More stable interest rates and improved credit access are two of the most significant factors, along with sellers adjusting their expectations and buyers who are willing to use structure (earnouts, seller notes, rollover equity) to bridge any gaps. Sellers entering the market prepared with reliable financials, clear forecasts, and realistic expectations are the ones securing the strongest multiples. Financing Conditions EY’s Private Equity Pulse from Q3 also indicates significantly improving financing conditions. They say direct lenders are staying highly active and offering competitive pricing and flexible structures, while the broadly syndicated loan market has reopened for larger buyouts. Their report cites PitchBook LCD data showing that in the U.S., syndicated loan activity reached a record $404 billion in Q3, reflecting renewed confidence from both borrowers and lenders and signaling stronger overall credit availability heading into 2026. The 25 basis point rate cuts by the Fed in September and October have been a much-needed bright spot in 2025, freeing up access to capital, and we could see one more before the end of the year. Deloitte’s 2026 M&A Trends Survey says that if that next rate cut materializes, it would be a “welcome tailwind for deal activity.” Strategic Buyers While private equity remains active, strategic buyers were the surprise strength of 2025. Solomon Partners M&A Outlook and Trends from October indicates that strategic M&A remains steady, with strategic deal volume up 21% in Q3 2025 vs 2024. They highlight elevated cash reserves and tariff-driven cost pressures as two factors that are encouraging consolidation. Strategics are also less rate-sensitive than financial buyers, giving them more room to compete on valuation. What Small & Mid-Market Sellers Should Expect in 2026 A Healthier, but Highly Selective, Universe of Buyers Expect a strong pipeline of buyers in 2026, but not necessarily for every business. Buyers are increasingly becoming more selective, prioritizing factors such as strong margins and stable cash flow, as well as recurring or contractual revenue. AI-enabled operations or meaningful data visibility, clean financials with audit-ready records, and a clear, demonstrable growth runway will continue to drive premium valuations. Businesses that lack these characteristics should anticipate more intensive diligence and a greater reliance on structured deal terms. Diligence Will Be Even Tighter Buyers will continue to push for deeper and more comprehensive diligence in 2026, making quality of earnings reports a baseline expectation and expanding operational reviews to cover technology infrastructure, cybersecurity, and AI adoption. They will scrutinize things such as inventory practices, working-capital trends, and customer concentration more closely, while also increasing their focus on data-privacy and overall regulatory compliance. Well-Prepared Sellers Will Have the Advantage Owners considering an exit in 2026 should begin preparing now. The most successful sellers in 2025 entered the process with 12–24 months of clean, normalized financials, a strong management team ready to support the transition, and early engagement with their legal, tax, and accounting advisors before going to market. This level of preparation consistently results in shorter diligence timelines and more secure, defensible purchase prices. While the market is improving, buyers remain disciplined, and seller-friendly terms are not guaranteed. Overall, the outlook for 2026 is cautious optimism with real opportunity. If 2025 was defined by recalibration, 2026 is poised to be a year of execution, particularly in the lower and middle markets. For business owners considering a sale, 2026 may present the best environment we have seen since 2021, but only for those who are preparing today to seize the opportunity of tomorrow.
December 2, 2025
Mergers and Acquisitions
Bridging the Gap: The Art of Communicating with First Time Sellers
It is estimated that 75 million baby boomers could retire by 2030. Many of these boomers have built successful businesses over decades, and they are now ready to sell as they move into the next phase of their lives. This is leading to a rise in M&A activity involving first-time sellers who are financially sophisticated and emotionally invested in their business, but they have not experienced the pace, process, or complexity of an acquisition. When this kind of first-time seller is involved, there can be some tension if buyers bring in large law firms who utilize their standard “big deal” approach. This specific client needs more clarity, connection, and practical guidance as opposed to layers of process. The Process Can Overwhelm the Person When a large law firm comes in on the buyer’s side, they bring an undeniable level of horsepower to transactions. But the same approach taken for billion-dollar deals isn’t necessarily a fit for the sale of a closely held business, and it can lead first-time sellers to feel sidelined and overwhelmed by complex jargon, unexpected costs, or rigid workflows. It can also lead the seller’s counsel, who they have likely worked with for years, to feel out of step with the tempo and expectations of the larger firm. The result is often an erosion in goodwill between the buyer and seller before the deal closes. The Advantage of the Middle-Market and the Art of Adapting This significant disconnect has created an opportunity for middle-market firms that understand both sides of the table. Middle-market firms offer sophisticated, deal-tested counsel who still prioritize communication and trust. They are better able to breakdown the jargon of big firms into advice business owners can understand and act on, helping these first-time sellers to feel informed and empowered, rather than frustrated and intimidated. But bridging this kind of a gap isn’t just about legal skill. It also requires a level of emotional intelligence and the ability to recognize when a seller needs context or reassurance. It also requires an understanding that every negotiation does not necessitate a 100-page response. There is an art to adapting the process to the client’s needs and experience level without compromising the quality of the transaction. The Importance of Nuance There is no one size fits all approach to transactions. They are all different, and they all require a nuanced approach. If a first-generation business owner is selling their life’s work to a PE firm, there is a very different set of concerns involved than if a serial entrepreneur is on their fifth exit. It is critical that counsel knows how to balance structure with flexibility and sophistication with accessibility, meeting clients where they are as opposed to forcing the client into a transactional template. Applying this kind of nuance to transactions can lead to a smoother process and a collaborative closing. There is significant value in the firms that can operate in the middle. They bring the kind of insight and technical strength expected from big firms, but they also have the responsiveness and reliability expected from small firms. As the market becomes further shaped by generational transitions and first-time sellers parting with their closely held businesses, the balance that middle-market firms bring to the table is more than just a competitive advantage. It is what gets this kind of deal done.
November 4, 2025
Mergers and Acquisitions
How Early Legal Counsel Shapes a Smooth Deal
Selling a business is never just about numbers on a page, it’s about preparation, people, and navigating the unexpected. Mike Mercurio presents a compelling series of conversations with client and former Fireline owner Anna Gavin, as she shares the real story behind her company’s sale. From the private moment she first decided to sell, to the surprise challenges of disclosure schedules, and the essential role of trusted advisors, Anna offers a rare, inside look at what the process truly feels like. Whether you’re years away from a sale or already planning one, her journey provides invaluable lessons on timing, team, and trust. In Part 6, the last of our Selling Your Business series, client and former Fireline owner Anna Gavin shares how early involvement from legal counsel Mike Mercurio and Offit Kurman set the tone for the entire transaction. Beyond just reviewing Letters of Intent (LOIs), the legal team played a crucial role in educating and mentally preparing her for complex steps ahead well before they became urgent tasks. This proactive approach helped avoid surprises and ensured the process moved smoothly, highlighting the value of strategic legal guidance from day one.
October 24, 2025
Business
Due Diligence: It's Not Just a Checklist
Selling a business is never just about numbers on a page, it’s about preparation, people, and navigating the unexpected. Mike Mercurio presents a compelling series of conversations with client and former Fireline owner Anna Gavin, as she shares the real story behind her company’s sale. From the private moment she first decided to sell, to the surprise challenges of disclosure schedules, and the essential role of trusted advisors, Anna offers a rare, inside look at what the process truly feels like. Whether you’re years away from a sale or already planning one, her journey provides invaluable lessons on timing, team, and trust. In Part 5 of our Selling Your Business series, client and former Fireline owner Anna Gavin reflects with her M&A attorney, Mike Mercurio, what it really felt like to go through due diligence and how even with a well-run, clean business, it was more intense than expected. Initially confident and prepared to tackle a long checklist, she quickly realized that diligence wasn’t just about ticking boxes it was a full-blown deep dive into every corner of the business. From finances and leases to operations and infrastructure, nothing was off limits. She compares it to an IRS audit but ten times. If you're heading into diligence, this is a must-watch for understanding what could be ahead.
October 16, 2025
Business
The Unsung Heroes of a Successful Exit: Your Advisors
Selling a business is never just about numbers on a page, it’s about preparation, people, and navigating the unexpected. Mike Mercurio presents a compelling series of conversations with client and former Fireline owner Anna Gavin, as she shares the real story behind her company’s sale. From the private moment she first decided to sell, to the surprise challenges of disclosure schedules, and the essential role of trusted advisors, Anna offers a rare, inside look at what the process truly feels like. Whether you’re years away from a sale or already planning one, her journey provides invaluable lessons on timing, team, and trust. In Part 4 of our Selling Your Business series, M&A attorney Mike Mercurio along with client and former Fireline owner, Anna Gavin touch on the critical role that advisors, including financial advisors and Offit Kurman as legal advisors, play throughout the deal process, especially in those intense final weeks leading up to closing. From reviewing contracts and translating legalese into plain English, to offering a safe space for honest questions, Anna reflects on how her legal team became both a guide and sounding board. If you’re thinking about selling, this is a reminder that having experts in your corner isn’t a luxury, it’s a necessity.
October 9, 2025
Business
Due Diligence in M&A Transactions: Why First-Time Buyers Should Avoid Analysis Paralysis
For many first-time buyers, the initial instinct in M&A transactions is to scrutinize every financial detail, prolonging the diligence process until they have an answer to every single question. This is certainly understandable, particularly for first-time buyers; however, this approach can often do more harm than good. The reason many deals fall apart is because they lose momentum, conditions shift over time, or sellers simply lose patience and walk away. All of these are considerable risks when the diligence process extends too long. Over-Diligence While thorough diligence is essential in any M&A transaction, when there is too much focus on financial minutiae, it can result in decision making paralysis. For first-time buyers, this can be difficult as they struggle to quantify risk and get caught in over-diligence, or a cycle of analysis and re-analysis. What can end up happening is analysis paralysis, meaning the fear of the unknown stops a deal from progressing. When buyers engage in over-diligence, it can lead to deal fatigue, where one or more parties lose interest or confidence as the process drags on for too long. When the diligence process stretches out, market conditions can also shift during the delay, or there could be internal changes such as an executive departing or a new business challenge arising. Timing is Essential In any transaction, momentum is key, and timing is everything. During the diligence process in M&A transactions, there are three ways in which timing can make a critical difference. First, timing is essential to the overall process. By keeping diligence tight, you can better ensure that the entire process will be compact and efficient. Then, there is timing of the market. When external factors such as regulatory shifts or new competitors pop up, they can start to impact deal value when a deal lingers. And finally, there is the internal timing of the target company itself. Over time, internal challenges could arise with leadership or operations that can lead to unnecessary hurdles. So, when diligence drags on too long, buyers run a significant risk of paying the same price for a business that could be fundamentally different, or even losing the deal all together. Buyers should also consider the period of exclusivity to complete diligence outlined in the LOI. That period of exclusivity can run out, and buyers could be forced to request extensions if they spend too much time focusing on incremental details. At a minimum, this can erode confidence, and at the worst, the seller could walk. Built In Protections It important for first-time buyers to understand one constant in M&A transactions: there is risk in every deal. But equally as important to understand is that you do not need to chase every risk. That is why there are built-in protections in transactions to help buyers move forward even when every minute detail is not fully uncovered during the diligence process. Buyers should work closely with legal counsel and advisors to structure agreements that include contractual provisions such as representations, warranties, indemnifications, and insurance solutions to protect parties from anything that was not uncovered. These kinds of tools are designed to balance the interests of buyers and sellers, and they allow buyers to focus their diligence efforts on those issues that affect valuation or viability of the deal, rather than wasting valuable time attempting to eliminate all risks. At the end of the day, diligence is designed to manage risk, not to eliminate it entirely. When you resist the tendency to over analyze financials, and stay focused instead, you can better maintain the necessary momentum and avoid paralysis. This leads to deals that close with confidence and are set up for long-term success.
October 6, 2025
Business
The Part of the Deal No One Warns You About: Disclosure Schedules
Selling a business is never just about numbers on a page, it’s about preparation, people, and navigating the unexpected. Mike Mercurio presents a compelling series of conversations with client and former Fireline owner Anna Gavin, as she shares the real story behind her company’s sale. From the private moment she first decided to sell, to the surprise challenges of disclosure schedules, and the essential role of trusted advisors, Anna offers a rare, inside look at what the process truly feels like. Whether you’re years away from a sale or already planning one, her journey provides invaluable lessons on timing, team, and trust. In Part 3 of our Selling Your Business series, client and former Fireline owner, Anna Gavin chats with her M&A attorney Mike Mercurio about a step that often catches sellers completely off guard — disclosure schedules. After what feels like the heavy lifting of diligence, you're suddenly asked to translate everything into a legal document that modifies your reps and warranties. It’s tedious, detailed, and critical to the final outcome. Anna shares her first-hand surprise at how complex this stage was and why having the right legal support made all the difference.
October 2, 2025
Mergers and Acquisitions
Finding the Right Deal Partners: Why Pace and Fit Matter
Selling a business is never just about numbers on a page, it’s about preparation, people, and navigating the unexpected. Mike Mercurio presents a compelling series of conversations with client and former Fireline owner Anna Gavin, as she shares the real story behind her company’s sale. From the private moment she first decided to sell, to the surprise challenges of disclosure schedules, and the essential role of trusted advisors, Anna offers a rare, inside look at what the process truly feels like. Whether you’re years away from a sale or already planning one, her journey provides invaluable lessons on timing, team, and trust. In Part 2 of our Selling Your Business series, Anna Gavin dives into one of the most overlooked but critical aspects of selling a business: choosing the right partners for the deal. She discusses with her deal counsel, M&A attorney Mike Mercurio, that from legal advisors to teammates, not everyone is the right fit for every situation. From the sell side perspective, she shares how important it was to align not just on expertise, but on pace, communication style, and approach. Keeping things simple, focused, and moving forward became the guiding principle and it made all the difference.
September 25, 2025
Mergers and Acquisitions
What Really Happens When You Decide to Sell Your Business?
Selling a business is never just about numbers on a page, it’s about preparation, people, and navigating the unexpected. Mike Mercurio presents a compelling series of conversations with client and former Fireline owner Anna Gavin, as she shares the real story behind her company’s sale. From the private moment she first decided to sell, to the surprise challenges of disclosure schedules, and the essential role of trusted advisors, Anna offers a rare, inside look at what the process truly feels like. Whether you’re years away from a sale or already planning one, her journey provides invaluable lessons on timing, team, and trust. In Part 1 of our Selling Your Business series, client and former Fireline owner Anna Gavin shares her personal and professional journey that followed her pivotal decision to sell her business. From quietly sitting with the decision for a year to finally voicing it to her spouse, she walks M&A attorney Mike Mercurio, who served as her counsel and deal attorney, through the early steps she took to get informed and prepared. By attending panels, listening to expert advice, and beginning the groundwork a year in advance, her story highlights the importance of planning and just how early that planning really needs to begin.
September 18, 2025
Business
Strategy and Deal Making: Understanding the Nuances of the Buy Side Approach
When it comes to today’s deal market, no two buyers approach acquisitions in the same way. For companies exploring a sale, or for boards weighing offers, understanding the distinct perspectives and motivations of private equity (PE) firms vs. strategic buyers is a key component in the decision-making process. Most data shows that strategic buyers are involved in a larger percentage of acquistions in the U.S. than PE firms, with some estimating they make up about 70% of transactions. While both categories of buyers are interested in achieving growth and value creation, their objectives, timelines, and deal-making strategies differ in ways that can shape everything from valuation to the post-closing integration process. What Drives Different Types of Buyers At the heart of every acquisition lies one simple question: What is driving the buyer? Understanding the why is essential as it determines factors such as how the deal will be structured, how risks will be allocated, and what life will look like post-closing. For most M&A transactions, buyers generally fall into three categories: Private Equity (Financial Sponsors) – These investment firms are highly focused on financial returns, have shorter investment horizons, and a defined exit strategy. They are looking to acquire a company with a goal to exit for a profit. Strategic Buyers (Operating Companies) – This category is made up of public companies, large private corporations, or industry leaders who concentrate more on finding synergies, long-term competitive positioning, and importantly, the integration of the target into their existing organization. Hybrid and Alternative Buyers – This group may include family offices, sovereign wealth funds, and consortiums, which may offer a blend of financial discipline and strategic motivations. Private Equity’s Playbook Private equity buyers typically operate within defined fund cycles, translating into a clear investment horizon, which is often five to seven years. Their acquisition strategy centers on unlocking value, whether that is through operational improvements, growth initiatives, or bolt-on acquisitions. There are several key hallmarks of the private equity approach, including discipline surrounding valuation. PE firms are very focused on returns, which can make them much more price sensitive than other buyers. They also utilize leveraged financing as a core component of their capital structure. This can magnify returns, but it also includes an additional risk factor. PE buyers also enter the transaction with the end in mind. They are concentrated on the exit event, whether that is a sale down the road, IPO, or recapitalization. For sellers, partnering with private equity can mean access to growth capital and operational expertise that can be invaluable, but it likely will not provide the kind of long-term “home” that a strategic acquirer would. The PE buyer is looking to exit as soon as the time is right. The Strategic Buyer’s Perspective As opposed to their PE counterparts, strategic buyers, pursue acquisitions to achieve synergies and create competitive advantages. They are motivated by expanding their market share, entering new regions, or acquiring complementary technologies. Strategic buyers often have longer investment horizons and could be willing to invest more heavily on the front end, knowing that they are looking to achieve returns over a longer time frame. This means that they might pay more of a premium when they can justify it through cost savings, revenue growth, or vertical integration over time. These buyers are going to be looking to integrate the target into their existing operations, which can impact culture, systems, as well as management continuity. Sellers may see strategic buyers as a more stable option as they are “in it for the long run.” The Rise of Hybrid Buyers There is an increasingly important category for sellers to consider, and that is the hybrid buyer. This category can include family offices, sovereign wealth funds, or corporate-backed investment arms which blend the return-driven discipline of a PE buyer with the more patient objectives of a strategic buyer. For certain sellers, for example founder-owned businesses, this option can be an attractive middle ground that presents a “best of both worlds” scenario. On the sell side, understanding the nuances of the buy side is essential to making the right decision. The “best” buyer isn’t always the one that comes in with the highest offer, and it is important to consider things such as long-term vision, cultural alignment, deal certainty, and growth support as well. There are some distinct differences between buyers, and to best negotiate terms and maximize value and long-term success, sellers must appreciate these differences and prepare accordingly.
September 10, 2025
Mergers and Acquisitions
Deal Flow Thawing: Is the M&A Market Finally Finding Its Footing?
After a rocky past six months, there is cautious optimism that merger and acquisition (M&A) activity is beginning to unfreeze. For much of the past year, there have been mismatched expectations around valuations and limited access to capital that have caused activity to stall. According to a recent report by PwC Global, “lending rates have long been one of the two key factors influencing M&A activity, the other being valuations.” So, while buyers were eager and sellers were hopeful, the numbers rarely lined up. But things could now start to change. The Valuation Tug-of-War One of the biggest barriers to getting deals across the finish line has been price. Many sellers have been holding onto lofty valuations based on pre-2022 market highs that simply aren’t realistic today. Meanwhile, buyers, who have been dealing with tighter credit markets and greater scrutiny from lenders, have been laser-focused on the fundamentals. All of this has resulted in a frustrating standoff where deals collapse not due to a lack of interest, but because no one can agree on what the business is truly worth. In fact, earlier this year, Arrowpoint Advisory noted a 26% decline in deal volume in North America, due in large part to “valuation mismatches between buyers and sellers.” We're now seeing a slow realignment. Valuation expectations are coming back to earth, with PwC noting that in today’s uncertain environment, it is important to not overreach on valuations. Deal structures are also evolving to bridge the remaining gaps, with earnouts, seller financing, and rollover equity becoming more common. It is this kind of flexibility that is helping to get deals done. A Shift in Diligence Dynamics Another notable change has been the quality of earnings (QoE) process. Two years ago, it was often a buyer-driven analysis, completed after signing a letter of intent (LOI). Now, many sellers are proactively conducting QoE studies before going to market. It’s a smart move to arm themselves with clean, vetted financials that can help to accelerate buyer confidence and reduce the risk of retrading. But there is a catch. Even with a proactive QoE, once a deal goes under LOI, buyers are digging deeper than ever. Diligence is intense, and the time from LOI to closing can stretch longer than expected. KPMG’s 2025 Deal Market Study points to heightened diligence and risk assessment as top challenges for 52% of corporates and 42% of private equity sponsors in the current economic landscape. And 47% of corporates also pointed to prolonged deal closing timelines as an issue, highlighting the link between deeper diligence and slower transactions. So, by the time due diligence wraps, earnings may have shifted, or market conditions may have changed, sometimes to the point where the lender’s original terms no longer match the reality of the deal. The Capital Crunch is Real, But Not Fatal Banks are still lending, but there is an increased level of caution and a decreased appetite for risk. We’ve seen situations where buyers get a term sheet for, say, $8 million in debt financing, only to find that after diligence or revised financials, the deal no longer pencils out, or the loan size is cut. That kind of late-stage shift can derail even the most promising transaction. That’s why it’s more important than ever to stress-test the deal early. Build in buffers, anticipate lender concerns, and don’t underestimate the importance of aligning everyone (seller, buyer, and lender) on realistic numbers from the start. The M&A market may not be booming, but the ice is cracking as valuations find firmer footing, buyers adapt to longer timelines, and sellers are more prepared. If you're contemplating a transaction on either side, now is the time to get your house in order. Quality of earnings, capital access, transparency, and flexibility will be the make-or-break factors in the deals that get done in the second half of 2025.
August 4, 2025
Business
Effectively Representing Entrepreneurs: Bridging the Gap Between Business and Law
Entrepreneurs represent a unique type of client for attorneys. They thrive on uncertainty, they move fast, and they see opportunities where many others see red flags. They often have a much higher risk tolerance, and they are visionaries who challenge the status quo, not only in the markets they disrupt, but also in the regulatory or legal frameworks that often cannot keep pace with innovation. For attorneys representing entrepreneurs, there can be a clear challenge as they struggle to bridge the gap between the law and the entrepreneur’s fast-moving world. Therefore, it is critical to remember that when working with entrepreneurs, the law is not the only seat at the table. Their legal counsel is just one of many voices in the room involved in making strategic decisions. Law, finance, insurance, product development, and growth marketing must all come together to make sound decisions and to create a path forward. Attorneys must understand this broader context and be able to operate within it. When advising entrepreneurs, it's not enough to say no or shut down ideas due to high risk levels. It is better to determine their tolerance for risk and develop a structure to make it work. Entrepreneurs don’t want a gatekeeper. They want legal counsel who can help them navigate the complexities of their world. Innovation Often Outpaces Regulation We have all seen that innovation frequently moves faster than the law. Just look at the incredible developments in AI over the past few years and the regulatory efforts that have significantly lagged the innovation in this space. We now see a patchwork of regulations across this country and on an international level. This highlights the point that an entrepreneur doesn’t always have the luxury of waiting for full regulatory clarity. They need legal counsel who can advise them on the current regulatory environment and help them anticipate and prepare for what the future might hold. Manage Risk, Don’t Eliminate It Entrepreneurial lawyering does not mean ignoring risk. It means identifying and managing risk, as well as helping the client embrace it in a calculated way. The idea isn’t to stifle innovation or kill ideas, but instead to make the big ideas viable within some parameters. There must be a mindset of managing risk smartly as opposed to avoiding risk at all costs. When attorneys can help entrepreneurs to see the legal implications of their decisions without shutting them down, they create the kind of trust that defines a successful attorney-client relationship. The Importance of Understanding Business Entrepreneurs want legal counsel who speaks their language and understands the many moving parts that make up their world. To have a seat at the entrepreneur’s table, it is essential to fully understand how legal decisions will impact their business objectives. This requires attorneys to evolve beyond just providing traditional legal advice and to move from the singular role of legal advisor to the multifaceted role of business advisor, risk strategist, and trusted partner throughout the entrepreneurial journey. There will always be a gap that exists between business and the law, as legal frameworks and regulations serve as roadblocks to the next big ideas coming out of startups. But great attorneys build bridges, not walls. They don’t ignore the law, but instead help entrepreneurs to navigate it with clarity, creativity, and awareness.
June 2, 2025
Mergers and Acquisitions
Younger Generations Looking to Sell: What Millennial and Gen X Business Owners Need to Know
I recently wrote about the “Gray Tsunami” and the mass numbers of Baby Boomers that will be retiring over the next few years. For Boomers, there are specific considerations that must be addressed if sale is their exit option. Similarly, there are age-oriented issues facing younger generations looking to sell their businesses. There are approximately 138 million Americans across the Millennial and Gen X generations as of the latest data. Millennials, born between 1981 and 1996, make up about 72.7 million Americans, and Gen X, born between 1965 and 1980, is not far behind at about 65.35 million. Data also shows that Millennials own 13% of small businesses, with Gen X owning 47%. As such, these two massive generations combined account for the majority of small business owners in the US. When looking at a transition at a much younger age, there are different issues to consider as opposed to those who sell later in life. Timing and Valuation A business owned by someone in their 30’s, 40’s, or 50’s will typically have a shorter life span than one owned by a Boomer. This means there might not be decades of financial performance to demonstrate stability to a buyer, and the business could be at a stage of high growth potential, but not maturity. While this is not always the case, buyers tend to prefer a strong history of stable cash flow and profitability. This is why timing is a critical factor. Younger generations should strategically plan their exit so that the timing works in their favor to maximize their valuation. Shifting market conditions and economic trends can impact valuations as well, so it is important to consider a variety of factors when determining the right timing that results in the greatest valuation. The retiring Boomer generation is also a major consideration in terms of timing. If a flood of Boomers are looking for buyers simultaneously, younger generations might look to delay their sales to reduce the competition for buyers. Conversely, this also presents a significant and unique opportunity to younger generations looking to buy. Planning for the Future Individuals in the Millennial or Gen X generations will likely have a great deal of life in front of them, so planning for the future is essential if they are going to sell their business. Consider the short and long-term goals of the sale. Do you want to be acquired to start a new business? Is your goal to retire early? Are you looking at other employment opportunities? Do you want to only sell a portion of the business to a strategic partner such as a PE firm, as opposed to a full exit? These are all important points to consider as they will help you to determine what kind of valuation will be required to meet your specific needs and how you need to structure the sale. These are different for everyone based on life goals, thus, looking at your future and what you need to make it happen is key. It is also important to work closely with your legal advisor to ensure the transaction is structured in a way to allow for the necessary financial and legal protections Selling to Start Again If your goal is to sell the company and start a new venture, then there are some very specific points that will need to be negotiated with the seller. For example, what kind of agreements does the buyer require? A non-compete agreement could prevent you from starting a similar business within a specific region or time frame, and a non-solicitation clause could restrict the hiring of former employees or soliciting clients. These are points that need to be front of mind if you are considering starting a similar business down the road, as they could seriously impact its success. Company Culture vs. Financial Gain Younger generations also tend to place a greater sense of value on company culture, employee retention, and customer loyalty. So, finding the buyer that will carry on the established company values and culture can play a larger role. Younger sellers must work to find the balance between carrying on the long-term vision for the company and maximizing the financial return from the sale. Selling your business at any age requires careful planning and preparation. But when selling earlier in life, there are complexities that exist due to the longer road that lies ahead. Having a clear long-term vision and understanding how the acquisition fits into your plan will help you to maximize the benefits and carry out your goals.
May 2, 2025
Mergers and Acquisitions
Every M&A Transaction Is a “Big Deal”
M&A over the last number of years has been “hot.” Despite slower-than-expected first quarter, we are anticipating another strong year for sell-side M&A. With stories of success, however, certain assumptions tend to follow. Business owners looking to buy or sell sometimes mistakenly believe Offit Kurman is too busy or expensive for their needs. A common objection typically sounds like: “My deal is probably too small for you.” I’ve been hearing from sellers with businesses worth $5 million or less lately. In any other context, it would be a bizarre thing to say. One million dollars is not “small.” For most of us, a check of that size would be a life-changing amount of money. However, the marketplace has a way of skewing perceptions. M&A advisors and investment bankers typically chase transactions in the eight and nine-figure range, and many refuse to go after anything worth less than $10 million. The same holds true for many law firms. As a result, owners of closely held businesses become jaded and self-select out of the market. Other business owners, meanwhile, believe the opposite: that our firm is exclusively focused on small or mid-market transactions, and we do not have the capability to handle large, multimillion-dollar deals. As someone who has seen hundreds of transactions through to completion, I can provide some perspective: every M&A transaction is a big deal. Especially if you’re a seller, we’re talking about what may be the single largest transaction in your lifetime. Moreover, at Offit Kurman, we are enterprise value agnostic. That means we are happy to provide representation and guidance to any business owner regardless of the potential size of a transaction. Here are a few more reasons why deal size should not limit your ability to work with a qualified M&A attorney: The size of the deal has no bearing on your legal fees. At Offit Kurman, we do deals at $1 million, $10 million, $100 million, and above (and below) because the purchase price has no financial impact on our billing structure. Our job is to zealously represent and protect every client. In contrast to investment bankers, who usually get paid a percentage of the deal, our attorneys bill at an hourly rate. That means time — not size — is what counts. Factors such as the condition of your business and the complexity of the deal determine how much work your attorneys must do. M&A demand is market-driven. Buyers and sellers control the M&A market. You could have a massive, multinational business — with advisors lining up to help you sell it — but if there’s no demand for the company, there’s no deal. Similarly, a small, well-positioned firm could be a hot commodity in its niche. A five-person government security contractor, for instance, might be able to leverage its relationships and intellectual property to create competition among multiple potential buyers. You don’t need to pay big money for expertise. Be wary of working with advisors who only take on enterprise M&A — there’s a good chance they’re overcharging and under-experienced. At Offit Kurman, we have successfully negotiated complex deals of various sizes, industries, and geographies. We bring this experience to every client matter. We can scale our representation to the size and character of the business, as well as the personality of the owner, at a price point and workflow that meets the client’s needs. Ultimately, M&A transaction size is relative to one’s frame of mind. As a seller, you may not be able to quickly change the value of your business, but you can control the value of the experience in shaping your future. Instead of worrying about how your purchase price compares to another business, focus on your own goals. Retiring wealthy? Now that’s a big deal.
April 17, 2025
Mergers and Acquisitions
Tariffs and DOGE: The Impact on Mergers and Acquisitions in 2025
While many felt that 2025 might finally be the year of the rebound for mergers and acquisitions (M&A), the M&A landscape has hit turbulence as we take off into the new year. In just the first few months, the new administration has imposed 25% tariffs on Mexican and Canadian imports, with a limit of 10% on Canadian energy, as well as a 20% tariff on products from China. These countries have already announced retaliatory efforts, including 15% tariffs from China on a variety of US farm exports and an announcement from Canada that they would “plaster tariffs” on more than $100 billion of American products over 21 days. There has also been a flurry of activity from the Department of Government Efficiency (DOGE), cutting funding and staffing across a variety of government agencies. According to a recent article in M&A Alerts, “The department’s influence could significantly impact industries reliant on government contracts, regulatory approvals, and cross-border investments, raising critical concerns for dealmakers in this evolving economic and political environment.” These efforts also raise regulatory concerns and are already running into legal challenges. Needless to say, the combination of tariffs and actions by DOGE has and will continue to have an impact on M&A activity this year. In fact, PitchBook is reporting that Morningstar DBRS stated they do not anticipate the substantial rise in M&A that was expected to arrive this year. So, why are these efforts poised to have such an impact on the M&A market? A lot of it has to do with uncertainty. Bloomberg points out that “the worst enemy of a booming market for mergers and acquisitions has always been uncertainty.” Their data shows that just over $470 billion in global transactions have been announced so far in 2025. That number is down 17% from the same period last year. If history proves to repeat itself, that is not a good sign for an M&A rebound in 2025, as Bloomberg also notes that “not once in the past two decades has dealmaking rebounded from a negative first quarter to beat the previous year’s tally.” In addition to uncertainty, tariffs have a real impact on businesses who import or export goods and can negatively impact profitability and valuations. Supply chains can also be subject to tariff-related risks, which makes the due diligence process in transactions more complicated. Additionally, tariffs have implications for deal structure and timing, and some deals that were in the works might have to be restructured to account for the impact of new tariffs. However, there could be some silver lining in all the doom and gloom. M&A Alerts also notes that DOGE’s efforts could have positive impacts on the business community, and “the push for efficiency and deregulation may accelerate approvals and boost deal flow.” So, while there is very real concern about the market volatility all of this is creating, there could be some pro-business efforts taking place that will have long-term benefits. No matter your opinion on the tariffs or the work DOGE is doing, these are very important areas to monitor for dealmakers as they will no doubt impact deal structure, target selection, valuations, supply chain issues, regulatory compliance, and a host of other factors at least for the foreseeable future. Legal advisors will be working to find ways to mitigate the impact and risks amid this period of uncertainty.
March 31, 2025
Mergers and Acquisitions
The Gray Tsunami: How Retiring Business Owners Can Prepare for a Successful Sale
There is a significant demographic shift headed our way known as the “gray tsunami,” as a very large portion of the American population will reach retirement age and eventually exit the workforce. In fact, we are at a peak time for retirement in America, known as Peak 65 where an average of 4.1 million Americans are projected to turn 65 each year between 2024 and 2027. To put it in perspective, that is about 11,000 people per day. This wave of older adults leaving the workplace stands to have a great impact across the business world as owners pivot to fill these roles left by retiring employees. But it will also have great implications for family-owned businesses as owners reach retirement age and must decide the best course for the future of their company when it is time to step down. A recent Wells Fargo Wealth & Investment Management survey indicates that 52% of business owners do not want their children to run and inherit their business. So, for many, this will mean considering the sale of the business as they look to exit on their own terms. By engaging in advanced planning, entrepreneurs can capitalize on this generational shift, creating a strategic opportunity to ensure their financial security and preserve their life’s work and legacy. Below, we look at some key considerations for baby boomer business owners as they plan for the next chapter in their lives and the potential sale of their family-owned enterprise. Finding the Right Buyer When you have spent your life building your business from the ground up, finding the right buyer when it is time to sell is critical. This means not only finding a buyer that will offer the right price to establish financial security in retirement, but also a buyer who will preserve the values and culture you have established. Finding this perfect buyer means having clearly defined goals for the future of the company. Outline the non-negotiable aspects of the company you want to preserve. This could be anything from retaining your employees to protecting customer relationships. Some owners wish to remain in an advisory capacity during the transition period to ensure continuity, others might want to make sure their business stays family owned. There are numerous types of buyers to consider, each with their own implications for the sale and future of the company. Again, the type of buyer you choose will correlate directly with the goals laid out from the beginning. For those focused more on maximizing value and less on legacy preservation, a strategic buyer such as a competitor could be the best fit. This could involve the integration of the business into a larger organization, so preservation of the company’s employees or culture could be at risk. A sale to a private equity (PE) firm is also an option, noting that the goal here is likely not to hold the business long-term but rather to sell again in 5-7 years. A sale to a family office would likely be a longer-term play. For those focused more on preserving the legacy of the company, selling to key employees or company leadership through a management buyout could be an option, or an Employee Stock Ownership Plan (ESOP) might be a consideration. As both would keep the business with current employees or leadership, maintaining the company culture and vision would be a priority. These are all important points to consider as they help to identify what you are really looking for in a buyer. Owners must work closely with trusted advisors to thoroughly vet potential buyers to ensure they align with those goals, and then carefully craft a deal structure that will best protect their legacy. Maximizing Business Value and Financial Security Maximizing the value of your business well before any exit event is key to establishing financial security for retiring business owners. This means engaging in careful planning, financial optimization, and strategic positioning very early in the process. It will be important to make sure every aspect of the business is streamlined and strengthened including financials, operations, employees, and suppliers. Conduct a comprehensive examination to determine if there are any areas that might need improvement to make the business the most attractive to potential buyers. Making necessary adjustments early on will help to create the best valuation and a smoother due diligence process. Setting the company up for future success by decreasing owner dependency and making sure there is strong leadership firmly in place is also important here. Determining what you will need for your own financial security post-sale must also be top of mind. This should involve working with advisors on significant tax planning to ensure the sale will be structured in the most beneficial way to minimize your tax liabilities as the seller. It will also be important to have a strategy for wealth management to ensure the proceeds of the sale will work for you. Legal Considerations As with any transaction, the sale of a family-owned business also comes with many legal considerations that can have a lasting impact and must be addressed alongside your legal counsel to minimize risk. These can include but are not limited to the following issues: Structuring the sale in the manner that best reduces tax implications and minimizes liabilities for the seller. Planning to avoid excessive capital gains and estate taxes. Conducting due diligence preparation to verify that all information Is accessible and in place and to resolve any outstanding issues. Ensuring liability protection and minimizing risks through avenues such as indemnification clauses and reps and warranties. Compliance with all regulatory and compliance requirements, which can become more complex based on some industries. Conclusion When a business owner makes the significant decision to sell, it will have long-lasting implications for the owner and the family overall. By working with advisors early on to carefully plan and prepare, baby boomers can enter retirement knowing they have not only maximized the value of their life’s work, but also preserved the legacy they have established.
February 28, 2025
Mergers and Acquisitions
Sell-Side M&A: Navigating Continuing Entanglements After the Deal Closes
Sell-side mergers and acquisitions (M&A) can be transformative events for companies, shareholders, and stakeholders alike. For the seller, this often means a significant payout and the culmination of years or even decades of hard work. However, post-closing sellers often remain connected to the business in various ways through what are known as "continuing entanglements." These post-transaction obligations can have legal, financial, and operational implications for the seller. Earnouts and Contingent Payments An earnout is a mechanism where the seller receives additional compensation based on the post-closing performance of the business. Earnouts are common in deals where the buyer and seller cannot agree on the valuation or where future business growth is uncertain. However, earnouts can be complex and can be areas of dispute post-closing. Sellers should negotiate clear terms that are tied to objective financial indicators, especially as Sellers may have little control over the business post-sale. Escrow and Holdback Provisions Buyers often require a portion of the sale price to be held in escrow or retained as a "holdback" for a period after closing as means to cover post-closing items such as undisclosed liabilities and indemnifications. Sellers need to negotiate protections and structure into these escrows including the terms of release and limitations against escrow claims. Representations, Warranties, and Indemnifications In M&A transactions, Sellers provide representations and warranties about the state of the business at the time of sale. If these representations turn out to be inaccurate or incomplete, the buyer may seek indemnification. Sellers should limit the duration and scope of their representations and warranties. At times, representation and warranty insurance may be an option to protect sellers from such claims. Non-Compete and Non-Solicitation Agreements Buyers often require sellers to sign non-compete and non-solicitation agreements as part of the M&A transaction. Sellers should also evaluate how these restrictions will affect their future business ventures and negotiate reasonable carve-outs when possible. Consulting or Employment Agreements In many cases, the buyer may require the seller to stay involved with a consulting or employment agreement, especially for transition and integration. Sellers should be careful about clarifying their role and expectations post-closing, including a seller’s ability to terminate the arrangement. Tax Implications Taxes drive transactions and M&A transactions can trigger significant tax liabilities for sellers. Sellers should work closely with tax advisors to structure the deal in the most tax-efficient way as well as be mindful of tax treatment for contingent payments like earnouts. Operational Matters Sellers should be careful to account for day-to-day potential entanglements with buyers post-closing. Such items include bank account transfers, leases, licenses, etc. Having a clear understanding with the buyer as to what will be the disposition of these items post-closing is important. Conclusion For sellers, it is important to be mindful of the continuing entanglements that can persist long after the deal is done. Legal, financial, and operational obligations may continue to bind the seller to the business for years to come. Sellers should work closely with experienced legal counsel to navigate these complexities and minimize their post-closing risk.
November 7, 2024
Mergers and Acquisitions
Risk Challenge: Bridging the Gap
Typical Professional Advisor Approach: Hates risk Paralyzed by risk Gap and Disconnection Between Typical Advisor and Typical Entrepreneur Typical Entrepreneur/Business Owner Approach: Embraces risk Views risk as gateway for opportunity My Approach to Bridge Marrying my 25+ years of practical understanding of business to specific clients’ risk tolerance profiles in order to educate and empower clients to make informed decisions. Entrepreneurs are a different than most people. Entrepreneurs embrace risk…every day. Business and personal risk to an entrepreneur are always present. Just ask an entrepreneur about their personal guarantee of the business’ debt (as an example). The smart management of risk by an entrepreneur is how he or she advances the business and sleeps at night. The problem is that most advisors working on behalf of business entrepreneurs approach risk from a position of fear and absolute avoidance. Thus, with the entrepreneur embracing and needing risk to advance business on one side of the spectrum, and the typical advisor on the other side of the spectrum, a large divide is created between the two parties and miscommunication and disconnect are often the end result. Like an entrepreneur being different, my approach is also different than most advisors. My job is to advise the entrepreneur of the potential risks associated with an action – and the job of my entrepreneurial client, once educated, is to let me know how little or much he or she “cares” about the risk. If my client does not “care” about the risk, I don’t waste valuable resources on it. However, if my client does “care” about the potential risk, I spend my time working to manage and mitigate the associated risk. Knowing that proper risk management is the key to helping entrepreneurs advance their business allows me and my clients to sleep well. Originally posted 7/18/2018, no content changes.
October 24, 2024
Business
Why Are the Fees to Sell a Business So High? It’s a Matter of Expectations
“How much will it cost to sell my business?” It seems like a reasonable enough question—and a business owner is wise to plan ahead and think about the financial impact of merger, acquisition, or other business transactions early on. However, focusing on what you’ll pay to sell a business is a classic example of “missing the forest for the trees.” Or, to put it another way, missing the sale for the fees. I get it. Legal costs are never pretty. Most business owners are fortunate enough to only pay attorney’s fees periodically, on an as-needed basis, for relatively small projects. We’re talking about document review, collections, intellectual property development, and so forth. If you’re really unlucky, you may need to bring on a lawyer for litigation. The associated bills aren’t pleasant, but they won’t bankrupt you (and if they do, you hired the wrong attorney). When you have the opportunity to consummate the sale of your company, on the other hand, you can expect to receive the largest legal bill of your lifetime. Depending on the size of the deal, your attorney may charge you upwards of six figures. In any other situation, the price would seem exorbitant—outrageously so. But a business transaction isn’t like other situations. It’s an extraordinary event with exponentially higher stakes than an owner is used to. No business milestone compares. Yes, you’ll receive the largest legal bill of your lifetime—because you’re earning the biggest payday of your lifetime. It’s a matter of scale and complexity. You will not get a good second “bite of the apple.” For sellers, some level of legal “sticker shock” is understandable. Few people on Earth can normalize earning several million dollars, or several hundred million, at once. The problem arises when a business owner handcuffs their advisors due to fee constraints. The handcuffs could have unintended implications for a seller. I recently represented a client who had grown accustomed to relying on legal assistance from a family friend. He was used to essentially paying his lawyer a couple of bucks and a case of beer. When it came time to sell his business, the client realized he needed a different caliber of attorney—but failed to adjust his expectations accordingly. When he learned he owed approximately $300,000 in legal fees, I watched the color drain from his face. Keep in mind my client’s business sold for $75 million. Our fees amounted to less than 1% of the total sale price. That’s in line with (admittedly loose) industry standards—if not below. My client knew how many hours were invested in the matter—and he had the budget in mind before the deal commenced. He knew a substantial bill was coming. But it wasn’t tangible for him until the end. The moral of the story? Don’t wait until after you’ve sold your business to think about the costs of selling your business. Develop a financial plan—and speak to your advisors to understand the moving parts and inputs to a transaction. Be prepared to spend substantial fees paying your attorney, investment banker, accountant, M&A advisor(s), and any other professionals involved in your team. After all, the sale of your business likely will be the largest financial transaction of your lifetime. Then, move all that to the back of your mind and prepare yourself for the biggest question ahead: what you’ll do with all that money after you close?
October 17, 2024
Business
What Message Are We Sending When We Say, “We Are Busy?”
Have you been busy lately? I’ve been busy. We’ve all been busy. Everyone, it seems, is really busy—super busy, incredibly busy—so, so busy. It’s become something of a greeting, in fact: “How are you?” “I’m all right—really busy.” “How’s work?” “Oh, you know, work’s been busy.” “How’s your family?” “Well, with school, and the kids, and the dog… things are busy!” Frequently, we’re not just busy but “swamped” or “crushed” by our daily activities and obligations. It’s almost as if we take pride in how out of control it all seems or how overwhelmed we feel. And yes, busyness is a feeling. So, why do we frequently tell others we’ve been “busy” or “swamped?” If I had to guess, I think we use these terms as a means of communicating success. No one wants to say they have no work or no clients—or no life, for that matter. Busyness also (conveniently) obfuscates the choice to prioritize one thing over another. Consider how often “I’ve been busy” follows “I’m sorry.” But just as “sorry” loses meaning with repetition, “busy” can’t insulate us from the consequences of our decisions. Nor can it affect how our words are received by others. If you’re not careful, a client may hear “I’m busy” as “I don’t have time for you” or “I can’t give you my best effort.” I’ll give an example. A few weeks ago, I approached a landscaping business. I knew the current season—late spring, early summer—would be a busy time for the company, but I figured they would be prepared for it and happy to take my business. The company was too busy to take my work. So, I went with a competitor. I wonder how the owner of the first business will feel when January comes around, and the business is not so busy. Missed opportunities are one of the many risks the always-busy face. I recently heard about a company that lost a multi-million dollar award because the would-be customer thought the organization lacked the time and capacity to handle the work. Employees had transmitted the company’s busy status to the prospect—a couple of offhand remarks was all it took. Of course, if you run a business, there will be times—many times—when your company is unable to meet a certain deadline or deliver results within a given timeframe. In these circumstances, the wise move is not to turn clients or customers away or stunt the conversation with a blanket “I’m busy” but to manage expectations. Take a moment to think past your current feelings of stress and consider the other party’s needs: Can the project wait a week? Would the client be willing to pay rush fees? Use that busy period as an opportunity to negotiate, consider your boundaries, learn, grow, and establish better lines of trust and communication. You should never promise what you can’t deliver, but that doesn’t mean you always have to say “no.” The old saying holds true: make hay when the sun is shining. When there is business, work harder and work longer. There is no guarantee a customer or client will come back if you turn them away now. Every relationship is important, and work arrives when it arrives—not always when it’s convenient. And remember: words have meaning. The next time someone asks how things are going, try something besides “I’ve been busy.” How about “business is good?” It is the truth, after all. Originally posted 6/13/2019, no content changes
October 10, 2024
