Mergers and Acquisitions

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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
Business
Search Funds, Independent Sponsors, and CCVs: Choosing the Right ETA Model
Entrepreneurship through acquisition has moved well beyond the traditional search fund. Today, ETA buyers can pursue small business acquisitions through several different capital models, each with different implications for fundraising, governance, control, and post-close operations. For emerging searchers, search fund entrepreneurs, and acquisition-minded operators, that creates both opportunity and confusion. The same target company may attract interest from a traditional searcher, a self-funded buyer, an independent sponsor, a committed capital vehicle, a family office, or a holding company. Each buyer may describe itself as part of the ETA ecosystem. But each model raises acquisition capital differently, allocates economics differently, and creates different expectations around governance, speed, control, and post-close operations. That matters because the structure you choose does more than affect fundraising. It affects: how sellers view you how lenders underwrite you how investors control decisions how much equity you may own after closing, and whether your structure works for one acquisition or a multi-acquisition platform For most emerging searchers, the first structure does not need to solve every future problem. It needs to fit the buyer’s current stage, capital access, risk tolerance, and first acquisition strategy. That distinction matters. A buyer may eventually want to build a roll-up, raise committed capital, or create a long-duration holding company. Those goals can inform the strategy, but they should not automatically dictate the structure for acquisition number one. Overbuilding the structure too early can create unnecessary legal expense, investor complexity, governance friction, and fundraising burden before the buyer has proven the core thesis. It can also push the searcher into a model that requires capabilities the buyer has not yet developed. In many cases, the better approach is to choose the simplest structure that supports the first credible acquisition while preserving room to evolve. A searcher who has not yet operated one business usually benefits more from building the foundational operator skills than from designing a vehicle for acquisition number five. The question is not only, “Where do I want to be in five years?” It is also, “What structure gives me the best chance to close and operate the first deal well?” The ETA Market Is Becoming More Fragmented Traditional search funds remain the most recognized and studied model. They have a long track record, a familiar investor base, and a relatively standardized playbook. For many first-time searchers, they remain the cleanest path into ETA. But they are no longer the only serious option. Self-funded search has become increasingly common, particularly among buyers who want more control, more ownership, and the ability to pursue small business acquisitions using SBA financing or smaller investor syndicates. Independent sponsors have also become one of the most active buyer categories in the lower middle market M&A ecosystem, especially for experienced operators and executives with investor relationships. Family offices continue to deploy more direct capital into private companies, sometimes backing searchers and sometimes acquiring companies directly. At the same time, committed capital vehicles and long-duration holdcos have become more visible. These structures are not entirely new, but their use within the ETA ecosystem appears to be accelerating. They reflect a shift from the classic idea of buying one company toward a broader effort to build repeatable acquisition infrastructure. That is the key development. ETA is no longer a single path. It is a group of related acquisition models that sit along a spectrum between individual entrepreneurship, lower middle market M&A, family office direct investing, and institutional private equity. Traditional Search Funds The traditional search fund is still the baseline model for many emerging searchers and search fund entrepreneurs. In a traditional search fund, investors provide capital to fund the search phase. The searcher uses that capital to source, evaluate, and negotiate the acquisition of a single target company. Once a target is identified, the same investor group typically has the right to participate in the acquisition financing. After closing, the searcher usually becomes the CEO or operating leader of the acquired business. This model works particularly well for first-time buyers who want structure, mentorship, and investor support. Many traditional search investors have seen dozens of transactions and can help a searcher evaluate industries, negotiate LOIs, manage acquisition diligence, structure financing, and prepare for post-close operations. The benefit is credibility and support. The tradeoff is control. Traditional searchers usually have investors deeply involved from the beginning. Those investors may have approval rights over the acquisition, the financing, the governance structure, major post-close decisions, and the searcher’s ongoing role. That involvement can be valuable, especially for a first-time operator, but it also means the searcher is not operating independently. Economically, traditional search funds usually give the searcher meaningful upside if the acquisition closes and performs well. The searcher typically receives a salary during the search phase, then earns equity through a combination of closing, time-based vesting, and performance-based vesting. While structures vary, many traditional search economics are designed to give the searcher a meaningful minority ownership position over time rather than majority control. The model is best understood as an apprenticeship into ownership. It is often a strong fit for a searcher who wants to buy and operate one good company with investor backing, guidance, and a known playbook. It may become less efficient if the searcher’s goal is to pursue serial acquisitions, build a multi-company platform, or retain more control over long-term capital allocation. Self-Funded Search Self-funded search is different in both psychology and economics, and it has become one of the most discussed alternatives to the traditional search fund. In a self-funded search, the buyer does not raise a formal search fund at the outset. Instead, the buyer funds the search personally or with limited outside support. Once the buyer identifies a target, the buyer raises capital for that specific transaction. In many small business acquisition strategies, SBA financing plays a central role. This model appeals to buyers who want more autonomy. A self-funded searcher usually has more freedom to define the target profile, negotiate directly with the seller, select investors later, and structure the deal around the specific opportunity. The model can also allow the buyer to retain substantially more equity than a traditional searcher, particularly in smaller transactions where debt financing (usually in the form of a SBA loan) covers a large portion of the purchase price. That ownership upside is one of the main attractions. But the model also places more risk on the buyer. Self-funded searchers often pay search expenses themselves. They may sign personal guarantees, especially in SBA-financed transactions. They may have fewer institutional resources during diligence. They may also have a thinner advisory network unless they intentionally build one. The economics can be attractive, but they are less standardized. The buyer may retain a large common equity stake, raise preferred equity from a small group of investors, and personally guarantee a portion of the acquisition debt. In a successful transaction, that can create better ownership economics than a traditional search fund. In a difficult transaction, it can create greater personal exposure. Self-funded search is often well suited for smaller acquisitions, local service businesses, business services companies, light industrial businesses, trades, healthcare services, and other lower middle market companies where SBA financing and hands-on operation can support the acquisition. The model is strongest when the buyer wants to own and operate a business with meaningful personal control. It becomes harder when the buyer wants to pursue larger targets, institutional equity, multiple add-on acquisitions, or a more formal acquisition platform. Independent Sponsors The independent sponsor model sits closer to private equity than traditional search and has become an important part of the lower middle market acquisition landscape. An independent sponsor typically sources a deal first, signs or negotiates the LOI, conducts diligence, and then raises equity for that specific acquisition. Unlike a committed fund or committed capital vehicle, the independent sponsor usually does not have fully committed capital available before the transaction is identified. This model works best for people with prior operating, investing, industry, or transaction experience. The independent sponsor must persuade three groups at once: the seller, the lender, and the equity investors. The seller wants confidence the buyer can close. The lender wants confidence in the sponsor, the capital stack, and the operating plan. The investors want confidence that the sponsor found a good deal and can manage it after closing. The model provides flexibility. The sponsor can choose different investors for different deals, customize governance, structure economics around the specific acquisition, and pursue opportunities that do not fit a traditional search fund profile. But the main weakness is capital certainty. Because the sponsor often raises equity after signing the LOI, sellers and intermediaries may worry about whether the buyer can actually close. That concern becomes more significant in competitive processes or situations where the seller wants speed and certainty. Economically, independent sponsor structures often include a mix of transaction fees, direct equity, management fees, and carried interest or promote. A sponsor might receive a closing fee, a minority equity position, and a promote above a preferred return to investors. The precise terms vary widely because independent sponsor economics are negotiated deal by deal. That variability is both a strength and a weakness. It gives the sponsor flexibility, but it also means the sponsor must negotiate economics repeatedly. If the sponsor lacks a strong investor base, the economics can compress quickly. The independent sponsor model is often a strong fit for a more experienced buyer who has deal access, sector knowledge, and investor relationships, but does not yet have a committed capital vehicle or fund. Committed Capital Vehicles Committed capital vehicles, or CCVs, are becoming increasingly relevant in ETA, especially for searchers and operators who want to move from one-off acquisitions toward a repeatable acquisition platform. A CCV generally refers to a structure where investors commit acquisition capital before a specific acquisition is identified or before a series of acquisitions is completed. The vehicle may be designed to acquire one platform company, pursue multiple acquisitions, or build a long-duration holding company. The basic appeal is straightforward: capital certainty. A buyer with committed capital can often move faster than a buyer who must raise equity after signing an LOI. That matters to sellers, lenders, brokers, and investment bankers. It also matters in fragmented industries where add-on acquisitions may become part of the strategy. This is why CCVs are gaining attention among more sophisticated searchers, acquisition entrepreneurs, independent sponsors, and operators. They are not simply trying to buy one company. They are trying to create a structure that can support multiple acquisitions, longer hold periods, and more repeatable capital deployment. The economic terms of CCVs usually look more like a small private equity or holding company structure than a classic search fund. The buyer often becomes an operator-sponsor and may receive management company economics, carried interest, direct co-investment rights, transaction-related fees, or long-term incentive economics tied to the performance of the vehicle. Investors may receive a preferred return, priority distributions, approval rights over major decisions, and protections around leverage, concentration, conflicts, related-party transactions, and sponsor removal. In many CCVs, the sponsor’s upside comes primarily through carry or promote after investors receive agreed economic thresholds. The model can create meaningful upside for a sponsor who builds a durable platform. But it also increases complexity. The sponsor is no longer just a searcher or operating CEO. The sponsor becomes a capital allocator, investor relations manager, acquisition strategist, governance manager, and platform builder. That is a different job. For emerging searchers, this distinction matters. A CCV may sound attractive because it offers more capital certainty and a more scalable structure. But it also requires a more developed investment thesis, stronger investor relationships, better governance design, and a clearer plan for how capital will be deployed. A CCV is usually more appropriate when the buyer has a repeatable acquisition thesis, a credible capital partner, a reason to pursue more than one acquisition, and the experience or support needed to manage a more institutional structure. It is usually less appropriate for someone who simply wants to buy one small business and operate it directly. Long-Duration Holdcos Long-duration holdcos overlap with CCVs but are not always identical. A holdco is usually designed to own operating companies over a long period of time. Instead of buying one company with the expectation of selling it in five to seven years, the holdco may be built around long-term compounding, cash flow reinvestment, and permanent or semi-permanent ownership. This model has become increasingly attractive to investors and operators who dislike the forced exit pressure of traditional private equity. For sellers, the holdco model can also be attractive. Founder-owned businesses often care about what happens after closing. They may prefer a buyer who plans to hold the business, retain employees, preserve culture, and invest in long-term operations. Economically, holdco structures can vary substantially. Some resemble private equity funds with preferred returns and sponsor carry. Others give the sponsor direct equity in the holding company. Some include management fees or shared services fees. Others rely more heavily on long-term equity appreciation. The central economic question is how value gets allocated between the capital providers and the operator-sponsor building the platform. That question can become complicated because the sponsor may be doing several things at once: sourcing acquisitions, managing executives, building systems, allocating capital, and creating the broader platform value. Holdcos can be powerful structures when the sponsor has a long-term vision and a patient investor base. They can also become difficult if investors want liquidity sooner than expected, if governance is unclear, or if the sponsor lacks the operational infrastructure needed to manage multiple companies. Family Office Direct Acquisition Models Family offices play several roles in the ETA ecosystem and broader lower middle market M&A market. Some invest in traditional search funds. Some back self-funded searchers. Some provide equity to independent sponsors. Some anchor CCVs or holdcos. Others acquire privately held companies directly. This makes family office capital both important and hard to categorize. In direct acquisition models, a family office may use its own balance sheet or investment vehicle to acquire a privately held company. It may install an operator, partner with a searcher, back an industry executive, or manage the company through an internal team. The main advantage is patient capital. Many family offices do not face the same exit pressure as private equity funds. They may be willing to hold a business for a longer period, prioritize cash flow, and structure a transaction around seller concerns, employee continuity, and long-term stewardship. But family offices vary dramatically. Some are highly institutional, with formal investment committees, detailed diligence processes, and experienced deal teams. Others are relationship-driven, informal, and dependent on a small number of family decision-makers. That variation affects everything: speed, governance, reporting, decision-making, and post-close expectations. Economically, operators working with family offices may receive salary, bonus, direct equity, phantom equity, profit participation, or equity vesting tied to long-term performance. The terms depend heavily on whether the operator is functioning as an employee, partner, sponsor, or acquisition entrepreneur. For emerging searchers, family office backing can be valuable, but it requires clarity. The searcher should understand whether the family office expects control, what decisions require approval, how future acquisitions will be funded, how economics vest, and whether the searcher is building personal ownership or merely operating a family-owned asset. Comparing the Models The models differ less by label than by what they are built to accomplish. A traditional search fund is designed to help a searcher find, acquire, and operate one company with investor support. A self-funded search is designed to give the buyer more control and potentially more ownership, usually in a smaller transaction with more personal risk. An independent sponsor model is designed to let an experienced buyer pursue deals without a committed fund, but it requires the sponsor to raise capital transaction by transaction. A CCV is designed to provide more capital certainty and support a broader acquisition strategy. A holdco is designed for long-duration ownership and compounding across one or more operating businesses. A family office model depends on the family office itself, but often emphasizes patient capital, direct ownership, and flexibility. The right model depends on the buyer’s objective. If the goal is to buy one strong business and become CEO, a traditional search fund or self-funded search may be the better fit. If the goal is to pursue larger or more complex deals with customized capital, the independent sponsor model may fit. If the goal is to build a repeatable acquisition platform, a CCV or holdco may make more sense. If the goal is to partner with patient capital and operate over a longer horizon, family office backing may be attractive. Economic Terms Matter Because They Shape Behavior Emerging searchers often focus on headline ownership percentage. That is understandable, but incomplete. The more important question is how the economic structure shapes behavior after closing. A buyer with too little equity may lose motivation. Investors with too much control may slow decisions. A sponsor with carry but no real capital at risk may create alignment concerns. A structure with no liquidity path may create investor tension. A self-funded searcher with too much personal guarantee exposure may become overly conservative after closing. The economics are not just financial terms. They are governance terms. We've discussed the importance of negotiating a governance structure in prior editions of Search Fund Operate. These terms influence who makes decisions, who bears risk, who receives upside, and how the company responds when post-close reality differs from the acquisition model. This is why vehicle selection matters before the LOI. By the time a buyer is under LOI, the structure has already started shaping the deal. A Practical Way to Think About Model Selection For an emerging searcher, the best starting point is not the structure. It is the strategy. If you want mentorship, institutional backing, and a proven path into operating one business, traditional search remains highly relevant. If you want control, ownership concentration, and are comfortable with personal risk, self-funded search may fit. If you have deal experience and investor relationships but no committed fund, independent sponsor may be viable. If you want to pursue multiple acquisitions under a repeatable thesis, a CCV or holdco may be appropriate. If you have access to a family office that understands your operating thesis, family office backing may provide patient and flexible capital. The mistake is choosing the model because it sounds more sophisticated. The better approach is to choose the model that matches the buyer’s actual capabilities, capital relationships, risk tolerance, and acquisition plan. ETA has become more institutionalized, but the core issue remains simple. The buyer has to close the deal, operate the company, and live with the acquisition structure after closing. That is where the differences between these models become real.
July 21, 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
Business
Why Real Estate Issues Slow ETA Deals
Most buyers expect environmental issues to be the real estate risk. In many deals, the larger risk is operational disruption. Real Estate Is Involved in Most ETA Transactions Real estate shows up in the vast majority of lower middle market transactions in some form. According to the 2025 Small Business Credit Survey published by the Federal Reserve: approximately 59% of operating businesses with employees operate from leased facilities approximately 17% operate from owned facilities approximately 17% primarily operate from a residence or without a dedicated operating facility That means roughly 83% of entrepreneurship through acquisition transactions involve some form of real estate or occupancy issue. In many deals, the primary issue is not ownership of the property itself. It is whether occupancy, control rights, lease assignment provisions, lender requirements, zoning, or permits could interfere with the business continuing to operate after closing. Those risks often become the primary real estate issues affecting the transaction. Most Buyers Initially Focus on Environmental Risk Environmental exposure absolutely matters. Particularly in: manufacturing industrial logistics automotive fuel-related operations older commercial corridors Phase I and Phase II reports remain critical diligence tools. But many search funders, independent sponsors, and ETA buyers do not place enough weight on operational interruption risk. While the business may technically exist independent of the property, operationally, it often does not. Location Becomes Part of the Business Most of these businesses are highly dependent on their physical operating environment. Examples include: machine shops with specialized electrical infrastructure distributors dependent on loading access and trucking routes contractors relying on outdoor storage rights restaurants dependent on parking and liquor licensing healthcare operators dependent on permitted use manufacturers operating under grandfathered zoning protections The issue is not simply whether the business can move. The issue is: cost of relocation operational downtime customer disruption employee retention permitting risk lender reaction transition timing Many ETA buyers do not fully appreciate this until diligence deepens. Lease Problems Often Surface After LOI One issue that repeatedly appears in ETA deals is whether the business can continue occupying the property after closing under the existing lease arrangements. Many buyers initially assume that the lease will (and can) transfer automatically at the time of closing. That is often incorrect. Most commercial leases contain assignment restrictions, consent requirements, or change-of-control provisions that must be examined carefully during diligence. Buyers need to identify: anti-assignment clauses landlord consent requirements change-of-control provisions expired lease terms undocumented extensions side agreements reflected only in emails use restrictions relocation rights held by landlords personal guarantees tied to the seller While the business operated successfully under these arrangements for years, a transaction introduces scrutiny, diligence, lender review, and operational friction. Lenders Underwrite Real Estate Issues Aggressively Occupancy stability becomes especially important in financed transactions. Particularly: SBA-backed deals owner-occupied industrial acquisitions cash flow sensitive businesses location-dependent operations Lenders often focus heavily on: remaining lease term renewal rights assignability ownership structure related-party lease economics appraised value environmental exposure zoning compliance A business with strong EBITDA but only 18 months remaining on a lease can quickly become a financing issue. Especially if the landlord has leverage during the closing process. Owned Real Estate Creates a Separate Transaction (and Separate Issues) Buyers often assume owned real estate simplifies the acquisition. In reality, it frequently creates a separate parallel transaction with its own diligence process, timeline, costs, and risks. The buyer must now perform diligence on both the operating business and the real estate itself, including: title survey and boundary issues easements zoning environmental exposure permits deferred maintenance tax exposure utility access stormwater compliance shared access arrangements The ownership structure also becomes critical, with many ETA deals using separate entities for the business and real estate. For example: one LLC owns the operating business another entity owns the real estate the operating company leases the property from the real estate holding company That structure often creates cleaner liability separation, financing flexibility, estate planning opportunities, and long-term control over the property. The larger problems often appear when the business and property were never properly separated in the first place. Many older lower middle-market businesses operate under informal ownership structures where: the seller personally owns the property family members own portions of the real estate title ownership differs from operational control there is no formal lease occupancy economics were never documented properly related-party arrangements evolved informally over decades That creates a very different set of diligence and execution risks. Buyers now need to examine: who actually owns the property whether all owners are participating in the transaction whether any family members must consent whether the operating business has formal occupancy rights whether market rent materially changes EBITDA whether lender underwriting changes once rent is normalized whether personal use or mixed-use issues exist whether title, tax, or succession issues affect the property whether post-close disputes could arise around occupancy or control Real Estate Distorts EBITDA More Than Buyers Expect Normalized occupancy costs also frequently change the underwriting. This issue regularly shows up in entrepreneurship through acquisition transactions, causing the business to appear more profitable because the seller owns the building. The company may operate with: below-market rent no formal lease favorable related-party occupancy terms deferred maintenance underreported capital needs Once the buyer normalizes rent, maintenance, taxes, insurance, market occupancy economics, and other carrying costs, the cash flow can compress quickly. That affects: leverage availability DSCR calculations valuation purchase price expectations post-close cash needs This is particularly important in manufacturing, warehouse, automotive, and hospitality acquisitions. Zoning Problems May Remain Hidden Until Diligence It can be a misconception to assume: “The business already operates there, so zoning must be fine.” Not always. A lack of zoning compliance can significantly disrupt operations. Businesses sometimes operate under: grandfathered nonconforming uses historical variances undocumented expansions expired permits improper outdoor storage occupancy inconsistencies signage violations prior approvals tied to historical ownership A transaction can trigger: new permit review lender diligence insurance underwriting review municipal scrutiny updated inspections The business may have operated without issue for years, but that does not mean the use remains protected post-closing. Real Estate Risk Can Show Up Everywhere Real estate issues quickly spread into: financing operations integration employee retention transition planning insurance working capital timing of closing The issues then become larger than the property itself. Real estate issues are most prevalent in lower middle market acquisitions where: documentation evolved informally occupancy arrangements were relationship-driven operational processes were never built for institutional diligence In these ETA deals, the answer to the real estate question ultimately controls: “Can the business continue operating the same way immediately after closing?”
June 10, 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
Business
Post-Close Alignment in Lower Middle Market M&A: Where Deal Stress Begins to Fracture
Most sellers and buyers in lower-middle-market M&A, including search funds, entrepreneurship through acquisition (ETA), and independent-sponsor transactions, begin to suffer from deal fatigue and welcome the post-closing phase of a business acquisition or M&A transaction. No more due diligence, no more negotiations, no more redlines. However, in many cases, the post-close phase is fertile ground for additional disputes to emerge. Most post-closing friction in lower-middle-market M&A deals is not caused by something that was absent from the deal. To the contrary, it is actually related to the negotiated documents governing the relationship between seller and buyer in the post-close transition phase. Consulting agreements, employment agreements, and corporate governance documents in rollover equity transactions seek to govern the relationship, but the relationship is still new in this phase. The parties are experiencing, for the first time, what it is like to work together after the change in dynamics (seller-owner to exited owner; buyer with funding to operator managing debt service and performance expectations). In this example, the seller rolled equity in the transaction and was now an equity holder in the buyer's platform company. The post-closing issues did not stem from a missing provision, but from ambiguities that existed across multiple documents that were meant to align and work together: seller notes, management agreements, and governance documents were all in play and created more confusion than clarity. That pattern is more common than most buyers expect, particularly in search fund, entrepreneurship through acquisition (ETA), and independent sponsor deals where post-close roles and governance tend to be more fluid. The LOI to Close Gap in M&A Transactions Most of these issues are not created at closing. They are created in the window between LOI and signing. At LOI, the parties align on high-level economics and general expectations: The seller will stay involved The business will transition smoothly Equity will keep everyone aligned in the case of rolled equity, or amounts due pursuant to the seller note will incentivize cooperation But those concepts get translated into separate documents depending on the deal: Employment agreement Consulting agreement Operating agreement Purchase agreement Each document answers a different question. Very few processes force those answers to be reconciled into a single operating model. That is where the gap forms. By the time you reach closing, the documents are “complete” but not always aligned. Where Post-Closing Issues Show Up in Business Acquisitions Employment Terms in Post-Closing Transition Buyers often assume that key individuals, particularly a selling owner transitioning into an operating role, will continue “as expected.” The employment agreement is where that expectation either becomes a reality or breaks down. The most common issues include: Role definition is too broad or not tied to actual authority Termination provisions do not reflect how performance issues will be handled Compensation structures do not match the deal model Example: A seller stays on post-close in a senior operating role (e.g., general manager) under a two-year agreement while the buyer installs its own CEO or operating partner. The buyer expects to reshape reporting lines and decision-making authority over time. The agreement, however, includes strong severance protections and defines material changes to duties or authority as “good reason.” Six months in, the buyer begins shifting responsibilities to its operating partner. The seller asserts “good reason” and triggers severance or other protections, despite the buyer viewing the changes as part of the planned transition. Nothing is technically wrong in the document. It just does not reflect how the buyer intended to transition control of the business. Consulting Roles and Transition Services Agreements Consulting arrangements are often treated as secondary or low-risk. In practice, they can drive real execution outcomes. This is especially true in customer transition and institutional knowledge transfer. Where this tends to go wrong: Scope of services is loosely defined Time commitment is not specified Compensation is not tied to outputs Example: A seller agrees to a 12-month consulting arrangement to support transition. The agreement references “reasonable availability” but does not define hours, deliverables, or response expectations. Post-close, the buyer expects active involvement in customer introductions and onboarding. The seller views the role as limited advisory support that can be provided from a remote location and not on-site. The result is predictable. The buyer feels unsupported. The seller believes they are complying with the agreement. Again, nothing is broken in isolation. The expectations were never aligned. Rolled Equity and Post-Close Governance Rolled equity is typically framed as a tool to align the parties in furtherance of a more profitable enterprise. In practice, it can be alignment in concept only, not in execution. Where this tends to go wrong: Different expectations around liquidity timing Limited clarity on governance rights Misunderstanding of distribution mechanics Example: A seller rolls 20% of proceeds into the new structure. The buyer plans to reinvest cash flow into growth and limit near-term distributions. The seller expects periodic cash flow similar to how they operated pre-sale. The operating agreement permits discretion on distributions, but the practical application of that discretion was never aligned. This is not a legal defect. It is an operating mismatch that surfaces quickly once capital allocation decisions begin. Why Post-Closing Misalignment Occurs in M&A Deals During the deal process, these items are negotiated in parallel: Purchase agreement Employment agreements Consulting agreements Equity and governance documents Each document may be internally consistent, but the following question should be asked: Do these documents, taken together, reflect how this business will actually be operated on day one? More specifically: Do they clearly define what the seller is required to do, what authority they retain or lose, how they are compensated for that role, and what happens if those expectations change or break down? If the answer to those questions is unclear, the issue is already embedded in the deal. Practical Considerations Pre-Close in Lower Middle Market Transactions This is almost always easier to address before closing than after. In practice, a strong lower-middle-market post-close package tends to do six things: Define the role with objective deliverables. Move beyond titles. Specify outputs, metrics, and decision rights that tie to how the business will actually be operated. Clearly classify the relationship. State whether the seller is an employee, consultant, or board-level advisor. Blurred status tends to create both operational and legal ambiguity. Precisely frame “cause” and “good reason.” If the buyer retains flexibility to change duties, reporting lines, compensation, or authority, that flexibility should be clearly bounded. Well-defined “cause” and “good reason” concepts are what translate flexibility into enforceable expectations. Separate consulting economics from deal economics. Consulting fees should stand on their own unless the parties intentionally link them to purchase price or earnout mechanics. Unintended overlap often creates disputes about what is being paid for performance versus transition support. Build explicit consequences for disruption. If authority is stripped or termination occurs outside the expected framework, the documents should address the outcome. That can include tolling, acceleration, deemed achievement, or extension concepts tied to equity or earnouts. Preserve a practical enforcement path. Rights are only useful if they can be exercised. Escrow access, information rights, expert determination procedures, and specific performance provisions tend to make these arrangements function in practice. Closing Thought on Post-Closing Risk and Deal Execution These are not technical refinements. They determine whether the post-close relationship functions when conditions change. Most post-closing issues do not come from a single broken provision. They come from small inconsistencies across multiple documents that were never forced to align into a single operating framework. If you are under LOI or in diligence, this is typically the window to fix that alignment without disrupting the deal. After closing, you are no longer interpreting intent; you are operating within the structure you drafted. If you are working through this in a live deal, step back and ask: Do these documents, collectively, dictate how decisions get made, how the seller participates, and how economics actually flow? If not, then the risk is not theoretical. It is already built into the deal.
May 29, 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
M&A Nuggets: Take It Personally - It's Goodwill
A common quandary facing sellers taxed as C corporations is the double tax that will result from a sale structured as an asset purchase — one level of tax to the corporation on the sale of its assets and a second level of tax to the stockholders on distribution of the net proceeds from the sale. This double tax can equal close to 50% of the total purchase price. The best way to avoid the double tax is to convince the purchaser to engage in a stock sale. That, however, is not always possible. In that case, serious consideration should be given to whether a portion of the purchase price can be allocated to the personal goodwill of the seller’s owners, as opposed to company goodwill. Any part of the purchase price allocated to personal goodwill will be subject to one level of tax. An additional benefit to the seller is that amounts allocated to personal goodwill are subject to capital gains tax rates. From the purchaser’s viewpoint, it can deduct amounts attributed to personal goodwill over 15 years, which is the same result as with amounts allocated to company goodwill. Personal goodwill is the goodwill of the individual owner of the seller that results from the person’s unique expertise, reputation or relationship with vendors and/or customers. Personal goodwill does not exist in every business. Before agreeing to an allocation to personal goodwill, an analysis should be made to determine the likelihood that the allocation will withstand any challenge by the Internal Revenue Service. The most quoted personal goodwill legal case involved a distributor of ice cream products who sold part of his business to Häagen-Dazs. In that case, the court recognized that the most valuable asset of the business was the owner’s business relationships with the business’s customers; the success of the business depended entirely on the owner. Another important factor was that the owner did not have a non-compete agreement. The court held that the owner, not the company, sold his assets to Häagen-Dazs. If the factors identified by the court in the Häagen-Dazs case apply and personal goodwill exists, a seller can obtain a significant tax benefit. That would be a very nice dessert on top of the main event of the business sale.
April 16, 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
M&A Nuggets
M&A Nuggets: Stop Signs
Contrary to popular belief, most business purchases do not succeed. That is not necessarily a bad thing, because occasionally the best deal is the deal that does not happen. To avoid closing a bad deal, the acquiror should be on the lookout for big red stop signs. Some stop signs are obvious, like material litigation, declining revenues, downward profits or a seller that engages in a particularly risky business. Some stop signs are not so obvious. These more subtle stop signs can spell disaster for a business combination. Examples include: a lack of symmetry in business culture between the purchaser and the seller the seller’s lack of proper recordkeeping, such as poor financial books and records, corporate documents or human resources files a seller who is unable to express a rational reason for sale a seller who appears recalcitrant in its position and/or somewhat aloof in the negotiation process Special attention should be paid to these last two items. Starting early in the process, the acquiror should ask a seller about its motivation to sell and its plans for devoting resources to the sale, and then track whether the seller’s actions follow its words. Otherwise, an acquiror could be negotiating with a seller who is not “all in,” wasting months of time and resources on a fruitless endeavor.
February 23, 2026
M&A Nuggets
M&A Nuggets: How to Avoid Hairline Fractures in M&A Deals
In medical parlance, a hairline fracture of the bone is caused by stress that can result from trauma, is painful, and curtails activity. Hairline fractures can also arise during an M&A transaction and are important to avoid. Hairline fractures can be caused by 1) lack of communication between the purchaser and the seller, 2) a delay in contacting third parties whose consent is required, and 3) professional advisors who put their desire to win at any cost above their client’s interests. How can hairline fractures be avoided? First, it is crucial for the purchaser and seller to fully understand each other’s objectives and to then memorialize all major business terms in a letter of intent. Too often, letters of intent are devoid of key business terms on the theory of “let’s just get the letter of intent signed and move on.” This often results in surprises, misunderstandings, and disappointment, all of which delay or doom a deal. Second, third parties whose consent is required, such as landlords and lenders, must be contacted well before the planned closing date. These third parties, who have their own processes and procedures when faced with a client sale, often take an extended time to react. Last, a seller should clearly explain its objectives, time frame, and expectations to its counsel and other advisors. A seller must work with advisors who will prioritize making the deal happen over winning every point in the negotiation. The lesson here is that, with proper communication and planning, hairline fractures in an M&A transaction can be avoided.
February 4, 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
M&A Nuggets
M&A Nugget: Qualified Small Business Stock Update
In 1993, Congress passed a tax law intended to incentivize entrepreneurs to invest in early-stage companies. This tax law, often referred to as QSBS (Qualified Small Business Stock) allows stockholders to exclude from tax a substantial portion of the gain on certain business sales structured as stock sales. Last year, the law was amended to expand tax savings. Here is how the QSBS tax exemption works: If a stockholder holds shares of stock issued initially and currently held in a C corporation, and The shares of stock have been owned for at least three years, and The corporation has assets of less than $50M or $75M (depending on the year the stock was acquired), and At least 80% in value of the corporation’s assets are used in the active conduct of a “qualified trade or business”, then When stock is sold in a business sale, between 50% and 100% of the gain can be excluded from tax. A “qualified trade or business” means any trade or business, except certain service businesses (usually involving the rendering of professional services), banking and insurance businesses, and certain real estate-related businesses. The most significant change in 2025’s QSBS amendment was to increase the amount of gain that can be excluded from tax. For stock issued before July 4, 2025, the maximum exclusion is $10M. For stock issued on or after July 4, 2025, the maximum exclusion increases to $15M. The tax savings can be substantial. For example, on the sale of a business in a stock transaction for $20M, if the original ownership was acquired before July 4, 2025, $10M can be excluded from federal tax (as long as the stock was held for at least five years), resulting in tax savings in excess of $2M. Planning Opportunity A stockholder that is not a corporation is eligible for the QSBS. This includes individuals and trusts and presents an extraordinary planning opportunity for an individual to create a trust to hold a portion of the company’s ownership. If the trust is structured as a separate taxpayer, the individual and the trust can each take advantage of the QSBS tax exemption. Many strict requirements must be satisfied to qualify for the QSBS, and anyone considering use of this tax law should engage a professional advisor who has experience with those requirements.
January 22, 2026
M&A Nuggets
M&A Nugget: A Failed Transaction is Not the End — It is the Beginning of M&A Success
Many business owners have experienced a failed transaction. After devoting months, if not years, and extraordinary amounts of time, resources, and money to complete a business sale, the acquirer backs out. The reasons vary from external forces (general market or industry conditions) to seller’s internal issues (usually operational or financial challenges) to substantial due diligence items that raise the risk level for the acquirer (such as a large unanticipated liability, tax debt, or technology debt) to a change in the acquirer’s business direction. Although a termination of a transaction by an acquirer is disappointing, it can also present an opportunity to the business owner. The failure of a transaction should lead the business owner to examine the reasons for the acquirer backout and address them diligently and continuously. For example, one common internal factor leading to a buyer backout is an inadequate sales team, resulting in lower than expected revenues, or an insufficient EBITDA. Like a major league baseball team that makes a sizeable investment by signing a free agent, investing in an upgrade in the sales team can provide an ultimate payoff multiple times the investment. If an acquirer backout is a result of risky due diligence items that arose, steps should be taken to address them, for instance, by implementing more robust risk management policies and procedures. The fact is that many sellers left standing at the altar by their purchaser ultimately engage in a very successful transaction. Two specific experiences I have had in this regard are (1) a seller whose purchaser backed out in early 2020 because of lower than hoped for EBITDA projections, the seller then doubling down its efforts to increase sales and EBITDA with a resulting transaction three years later with the same purchaser for a purchase price 40% higher than the proposed 2020 purchase price; and (2) a seller’s potential acquirer backed out of a $100,000,000 purchase in 2022, leading to the seller redoubling its efforts to increase sales and EBITDA, with an ultimate sale only one year later for an enterprise value of $160,000,000. The lesson here is that in the M&A world, as in life, a failure can lead to great success.
January 6, 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
M&A Nuggets
M&A Nugget: Smart Moves During an M&A Slowdown - Strategic Preparation for Business Owners
Although there are always segments of the M&A market that are busy, most advisors will tell you that there is a current slowdown in overall M&A activity. This gives sellers an opportune time to conduct “spring cleaning.” Just like the stock market, the M&A market ebbs and flows, and it is important that owners be prepared for the next M&A market flow. Here are a few steps you can take to be ready: Update Corporate Records – Make sure that ownership certificates reflect the current ownership of your business and that all required corporate documents exist. Consider implementing incentive plans to retain your key employees, which will help to drive the growth, value, and ultimate purchase price for your business. Review the classification of your business’s personnel between W-2 employees and independent contractors - always a hot-button issue with acquirers. Conduct an audit to ensure that your immigration documentation for employees is current and in compliance with the law. Review or have your CPA review the company’s compliance with sales tax rules to make sure that the company is filing sales tax returns and paying sales tax, where and when required. All of the above items, and many more, will be thoroughly investigated by any acquirer. By conducting spring cleaning now and arranging your business house to be in order, you will be steps ahead when the tempo of the M&A market picks up.
June 30, 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

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Firm Highlights

MACFO's Inside Successful CEO & CFO Partnerships

Please join us on September 18 for an event that’s sure to be a home run! ***We will lead off by interviewing our Spotlight Speaker Series guest, Baltimore Orioles CFO, Darline Llamas Llopis.*** After, we will ask ourselves, what separates great companies from good ones? We believe that more often than not, it is the strength of the partnership between the CEO and CFO that matters, so we are bringing you three CEO/CFO leadership teams to learn from. The Associated: Jewish Federation of Baltimore – Andrew Cushnir and Sam Klein Canusa Paper & Packaging – Mike Walter and Vince Salamone EMR – Caroline Kauffman-Kirschnick and Lisa Loeffler Join us for an exclusive executive briefing – three tandem presentations followed by a panel discussion - featuring CEOs and CFOs from different but leading organizations as they share candid insights into building trust, navigating difficult decisions, driving strategic growth, and leading through today's business challenges. You'll hear firsthand how these executive teams navigate conflict, align on priorities, and build high-performing organizations. Whether you're a CFO, controller, finance executive, or an aspiring business leader, you'll leave with practical ideas and fresh perspectives you can apply immediately. Meet Our Speakers: Darline Llamas Llopis • Orioles Chief Financial Officer Darline Llamas Llopis is in her second season with the Orioles as Chief Financial Officer (CFO). Prior to joining the Orioles, Llamas Llopis spent four seasons with the Miami Dolphins, Hard Rock Stadium, and the F1 Miami Grand Prix as Vice President of Finance and Retail. In this capacity, she managed the finance, accounting, payroll, account payables, procurement and merchandise operations for the team and race. She also previously served for four years as the Director of Finance and Controller at the Los Angeles Rams. Llamas Llopis started her career in public accounting with Ernst & Young and PricewaterhouseCoopers as a member of the Commercial Real Estate practice. Llamas Llopis completed her MBA at UCLA Anderson School of Management and received her Master of Accountancy from the University of Southern California (USC) where she also graduated cum laude with an undergraduate degree in business. She is a member of the American Institute of Certified Public Accountants (CPA) and is an active CPA. She resides in Baltimore with her husband, Devin, and their son, Santiago. Andrew Cushnir • The Associated: Jewish Federation of Baltimore President & Chief Executive Officer Andrew Cushnir is the President and Chief Executive Officer of The Associated, having started in the role in May 2024. He is the eighth person to serve in this role since The Associated’s founding over 100 years ago. Andrew brings a wealth of experience and a profound dedication to strengthening and enriching the Jewish community. His journey within the Jewish Federation system began as a passionate lay leader and volunteer before he transitioned into serving as a professional. He worked for the Jewish Federation of Los Angeles for twenty years, including in the roles of Chief Planning and Program Officer and Chief Development Officer. During this time, Andrew played a crucial role in reshaping the allocation process and fostering a culture of collaboration and partnership and he also led all annual, project, and emergency fundraising, as well as planned giving efforts. As a member of the Federation’s executive team, he also addressed complex community and organizational issues. Andrew and his wife Sharon Spira-Cushnir, a seasoned nonprofit human services executive, are the proud parents of two children in their early 20s. Sam Klein • The Associated: Jewish Federation of Baltimore Chief Financial Officer Sam Klein is a seasoned nonprofit finance executive with nearly two decades of experience leading financial strategy, operations, budgeting, and organizational transformation for mission-driven institutions. As Chief Financial Officer of The Associated: Jewish Federation of Baltimore, he oversees the organization's financial operations, investment stewardship, budgeting processes, risk management, and long-term financial planning, helping advance the Federation's mission of strengthening and supporting Jewish life in Baltimore, Israel, and around the world. Throughout his career, Sam has been recognized for his ability to align financial stewardship with organizational mission, drive process improvements, implement technology solutions, and build high-performing teams. His expertise includes nonprofit finance, strategic planning, budgeting and forecasting, investment oversight, financial reporting, compliance, operational excellence, and organizational growth. Sam earned a Master of Business Administration in Finance from the Johns Hopkins Carey Business School and a Bachelor of Science in Finance and Marketing from Syracuse University. Mike Walter • Canusa's Paper & Packaging Chief Executive Officer As Chief Executive Officer of Canusa Paper & Packaging (CPP), Mike Walter leads one of the world's leading independent international brokerages of containerboard and packaging papers. Mike recently celebrated his 20th anniversary with Canusa and has overseen a doubling of the business in the past five years. Mike’s first role at Canusa was an intern before moving into a risk management role. Progressive promotions over the years led Mike to serve as Canusa's Chief Operating Officer and General Counsel, as well as General Counsel for its affiliate, Canusa Hershman before becoming the CPP CEO on January 1st, 2025. Mike graduated with a B.S. in Commerce & Engineering from Drexel University before earning his J.D. at the University of Baltimore’s School of Law. Vince Salamone • Canusa's Paper & Packaging Chief Financial Officer Vince Salamone serves as Chief Financial Officer of Canusa Paper & Packaging, overseeing the company's global financial strategy and overall operations, risk management, and other shared services. Since joining Canusa in 2018, Vince has advanced from Corporate Controller to CFO. Prior to Canusa, Vince held senior accounting and financial reporting roles at modular space leader Algeco Scotsman and supply chain real estate operator Realterm, bringing extensive expertise in finance and corporate accounting. He began his career with Deloitte, providing assurance services to clients in aerospace and defense, software, and manufacturing throughout the Mid-Atlantic. Vince attended the University of Maryland and Towson University, earning his B.S. in Accounting in 2012 and his CPA license in 2014. Caroline Kauffman-Kirschnick • The Electric Motor Repair Company President Caroline Kauffman is President of EMR, where she leads company strategy, operations, business development, and culture. Having grown up in the family business and worked in nearly every area of the organization—from accounts receivable and human resources to operations and branch leadership—she brings a unique, firsthand understanding of what drives business success. Since becoming President in 2018, Caroline has championed employee engagement, teamwork, and innovative problem-solving while helping guide EMR's continued growth. She holds a Bachelor of Science in Public Relations from York College of Pennsylvania and is active in several industry and family business organizations. Lisa Loeffler • The Electric Motor Repair Company Chief Financial Officer Lisa Loeffler is a strategic Chief Financial Officer with more than 25 years of executive leadership experience driving growth, financial transformation, and operational excellence across private equity-backed, privately held, and international organizations. She has led finance functions for companies with revenues from $40 million to $600 million, specializing in M&A, FP&A, ERP implementations, financial strategy, and organizational transformation. Known for building high-performing teams and partnering with CEOs and boards, Lisa delivers scalable solutions that strengthen financial performance, improve operational efficiency, and position organizations for sustainable growth and successful transactions. Thank You to Our Sponsors

Publications & News

Offit Kurman Atlanta Office Recognized as Legal Food Frenzy Rookie of the Year

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Maximizing Cash Flow and Collections

Attorneys Sarah Sawyer and Russell Burger of Offit Kurman discuss how businesses can improve cash flow by staying on top of accounts receivable and treating collections first as a business process. They stress proactive client selection, credit reviews, AR management, and strong contracts with clear payment terms, remedies, fee provisions, and jurisdiction clauses. Sarah and Russell recommend establishing a clear internal process to identify overdue accounts and decide when to send demand letters or pursue litigation. For industries with frequent slow-pay issues, they suggest creating a repeatable, scalable collections “blueprint” and exploring AI to increase efficiency.

Meet Tevia Hoalst, TeKoda Accounting

In this episode of Java with Jim, host Jim Ries interviews Tevia Hoalst, owner and CEO of TeKoda Accounting. Tevia explains that TeKoda operates as an outsourced accounting department focused on pre-tax work and partners with clients’ tax firms. They provide customizable accounting support with a fully US-based team. She highlights TeKoda’s people-first, relational approach and shares that she is most proud of the company’s strong culture. She believes the client outcomes are improved by the low turnover and higher-quality work of her employees. Tevia discusses excitement about growth opportunities in the next six months, potentially including acquisitions. She shares a couple personal surprises, including not coming from an accounting background and running a draft-horse rescue on her farm.

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Offit Kurman’s Martin Garbus Following Successful Run of The People v. Lenny Bruce

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Offit Kurman Attorney Recognized on 2027 North Carolina Super Lawyers® List

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Offit Kurman Announces Addition of Four Attorneys

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Can AI Buy a Company? What Buyers Need to Know About AI’s Role and Limitations in M&A Transactions

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OIG Advisory Opinion 26-12 Approves Concierge Program Warranty for Surgical Outcomes

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The NIL Educational Workshop

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