Winning at M&A in 2025: The Insider’s Playbook | DarrowEverett LLP

As an avid Red Sox fan and former Los Angeles resident who often attended Dodgers games, I may still be basking in the Yankees’ loss in the World Series. Whatever the reason, I can’t help but draw parallels between the game of baseball and the world of M&A. Both are games of strategy, requiring a deep understanding of the market landscape, a keen eye for opportunity, and the ability to make quick decisions under pressure. And just like in baseball, the rules of M&A are constantly evolving, with new players, strategies, and technologies changing the game every year. As we look ahead to 2025, the M&A landscape is set to be more competitive than ever before, with new players entering the field and established industry giants continuing to dominate. To succeed in this landscape, those involved must have a clear understanding of the game and a well-defined playbook for success.

The Competition

In 2024’s deal landscape, value creation has transformed beyond simple cost-cutting. Acquirers now pay premium prices for companies with proven digital capabilities — think AI-powered customer analytics, automated operations, or breakthrough tech platforms. While traditional synergies like combining teams or consolidating facilities still matter, the real value drivers are technological advantages that can be scaled across the entire business. Smart buyers look for targets that don’t just occupy market space but actively shape it through innovation, customer experience, or unique business models. When industry giants like Microsoft paid $69 billion for Activision Blizzard or Amazon acquired One Medical for $3.9 billion, they weren’t just buying revenue streams — they were securing transformative capabilities that could reshape entire sectors. The game has evolved from simply growing bigger to growing smarter, with acquirers willing to pay top dollar for companies that can accelerate their digital evolution and market leadership.

So, how do you become a wild card in 2025 and compete with the industry giants? Keep reading to find out.

The Warm-Up

The Structure: If you ever plan on selling your entity or raising capital, the first decision to consider is your entity structure. The choice of entity structure significantly impacts transaction flexibility and operations. Each structure presents unique advantages and challenges: C-Corporations offer maximum flexibility for future capital raising and public offerings but come with more complex governance requirements. They also provide the most straightforward path for institutional investors and public markets. S-Corporations and LLCs offer operational flexibility but face ownership restrictions that may limit potential buyer pools. These structures work well for closely held businesses but may require reorganization before a significant transaction. Entity selection should align with long-term strategic objectives, considering factors such as future capital raising needs, potential acquirers, operational flexibility requirements, governance preferences, and more.

The Metrics: Before devising deal terms, the three most important components to consider are: target, timing, and valuation.

The first step in any successful M&A strategy is identifying the right targets. With the rise of new technologies and business models creating a crowded and competitive market for potential acquisitions, this is no simple feat. Successful acquirers know the key to winning lies in strategic alignment and cultural fit. They look for targets that complement their existing capabilities, expand their market reach, and align with their long-term vision. They also prioritize cultural fit, recognizing that a misaligned company culture can derail even the most promising deal. To identify the right targets, acquirers must have a clear understanding of their own strengths and weaknesses, as well as a deep understanding of the market landscape and potential synergies with potential targets.

Deal timing plays a crucial role in transaction success. Market conditions, industry cycles, and company-specific factors all influence transaction timing. Sophisticated buyers monitor these elements continuously, ready to move quickly when opportunities arise. This requires maintaining updated target lists, understanding industry dynamics, and having internal processes ready for rapid deployment.

Evaluating Players: Preliminary valuation frameworks help establish initial price ranges and deal structures. While detailed valuation work comes later, early-stage analysis typically examines comparable transactions, market multiples, and basic synergy potential.

The choice of valuation methodology can significantly impact negotiations and typically fall into one of two approaches: (1) market-based approach, or (2) income-based approach.

1. Market Approach: Market approach valuations involve assessing the value of a company by comparing it to comparable ones on the market. Similar to real estate, this approach typically favors sellers in hot markets, allowing them to leverage recent premium-priced transactions to justify higher multiples.
2. Income Approach: The income approach focuses on a company’s future income potential. The most common income-based valuation method is the Discounted Cash Flow (DCF) analysis. DCF estimates future cash flows and discounts them to present value. Buyers lean toward DCF analysis in volatile markets, using higher discount rates to justify lower valuations of early-stage companies. The discount rate is determined by a variety of factors, including cost of capital, recent market transactions, and risk.

Of course, there are other valuation methods that may come into play, depending on the deal. Asset-based valuations work best in industries with significant tangible assets, while revenue-based multiples often benefit high-growth companies with strong digital capabilities. Leveraged Buyout (LBO) analysis, favored by private equity firms, evaluates a company’s ability to generate sufficient cash flows to service debt while generally providing attractive investor returns. In LBOs, PE firms typically target companies with stable cash flows, limited capital expenditure needs, and strong market positions that can support significant leverage, usually seeking internal rates of return between 20-30%.

The Scouting Report

The Players: Due diligence in M&A has evolved beyond traditional financial analysis into a sophisticated process where different buyers approach target evaluation with distinct priorities, displaying their unique investment strategies.

1. Private Equity: PE firms prioritize predictable revenue metrics, focusing on customer cohort analysis and retention rates to assess stability and growth potential. They examine unit economics and customer concentration risks, seeking businesses that can scale efficiently while maintaining strong margins.
2. Strategic acquirers: Strategic acquirers take an industry-specific approach, evaluating synergistic potential and how target companies’ technologies or services can enhance their existing portfolio. Strategic acquirers are exactly that — strategic. They prioritize intellectual property, market position, and operational integration opportunities that drive cost savings or revenue growth.
3. Secured Lenders: Secured lenders provide debt financing backed by specific collateral — typically the target company’s assets, receivables, or inventory. As key participants in leveraged transactions, secured lenders evaluate both the quality of collateral and the borrower’s ability to service debt, often requiring first-priority security interests in the target’s assets to minimize their risk exposure. Secured lenders may desire to further limit their exposure using corporate or personal guarantees and a pledge of the ownership interest in the target.

The Ground Rules: Technology due diligence has become critical for all buyers, with deep assessments of infrastructure, scalability, and security protocols. Cybersecurity and data privacy compliance are now non-negotiable, especially in sectors handling sensitive data. Acquirers now evaluate digital transformation progress to ensure systems can support future growth.

Cultural assessment has become a crucial success factor, with buyers recognizing that misalignment can derail financially sound deals. They analyze leadership dynamics, organizational values, and employee engagement metrics to assess integration potential.

Both PE firms and strategic buyers now evaluate environmental, social, and governance (“ESG”) factors and technological capabilities as key value drivers. While PE firms focus on short-term operational improvements and market expansion, strategic buyers tend to prioritize long-term synergistic benefits.

If you are a seller, it is critical to have an idea of your ideal acquirer, so you can prepare your business to meet their specific due diligence requirements and maximize your company’s value in their eyes. Understanding these buyer perspectives can mean the difference between a successful exit and a missed opportunity.

The Starting Lineup

Smart deal structuring isn’t just about paperwork — it is about orchestrating the perfect symphony of terms and conditions, leaving both sides feeling strategically positioned and confidently aligned.

The Championship Roster: The best M&A teams are made up of experienced professionals who understand how to navigate the complexities of the M&A process. This includes legal counsel, tax advisors, and investment bankers who have a deep understanding of the industry and transaction structures. These professionals can help identify potential risks and opportunities, negotiate favorable terms, and guide the deal to a successful close. In addition, having a strong internal team of executives and advisors who have a deep understanding of the business and its value drivers is crucial. These individuals can provide valuable insights and help ensure the transaction aligns with the company’s overall strategic goals. Having the right team not only results in a smoother deal, it is one of the many components for success (read more of our entrepreneurial tips here).

The Bullpen: Before any substantive discussions begin, successful M&A transactions require a non-disclosure agreement (NDA). This first document sets the tone for negotiations and protects both parties’ interests. For sellers, NDAs safeguard sensitive business information, trade secrets, and the very fact that a sale is being contemplated. For buyers, signing an NDA signals serious intent and encourages seller cooperation in sharing critical business information. The most effective NDAs include clear definitions of confidential information, specific use restrictions, and survival obligations. This foundational document often includes standstill provisions preventing potential buyers from using the information for competitive purposes or attempting hostile takeover actions. Only after this protection is in place should parties proceed to preliminary deal discussions and term sheet negotiations.

Opening Moves: When choosing between asset and stock acquisitions, seasoned dealmakers know that success lies in the details. Asset deals offer surgical precision in selecting what you want, with buyers assuming only specifically identified liabilities while leaving historical and unknown liabilities with the seller. While stock purchases offer a streamlined acquisition path favored by many fast-moving acquirers, they require thorough risk assessment, as buyers automatically inherit all known and unknown liabilities of the target company. This distinction in liability exposure often drives deal structure decisions: asset purchases appeal to risk-averse buyers seeking to limit exposure, while stock deals attract those prioritizing speed and simplicity over liability concerns. Other factors are often considered when determining the structure of the transaction, such as transfers of permits and entitlements or minimization of federal, state, and local taxes. The choice between these structures often determines the transaction’s ultimate success and requires careful consideration of operational, financial, and strategic objectives.

The Game Plan: The letter of intent or term sheet (“LOI”) serves as the foundational road map for any M&A transaction, outlining key deal terms and establishing preliminary agreements between parties. While typically non-binding except for confidentiality and exclusivity provisions, LOIs serve as the strategic road map outlining fundamental deal terms and establishing the framework for negotiations. A well-crafted LOI addresses key elements including transaction structure, preliminary valuation, payment terms, and major closing conditions. The exclusivity period, typically 60-90 days, provides buyers necessary protection during due diligence, while sellers benefit from clear timelines and parameters. Sophisticated buyers use LOIs to address potential deal-breakers early, streamlining later negotiations and identifying obstacles before significant resources are committed. For sellers, carefully negotiated LOIs provide valuable deal protection through specific performance requirements. In today’s fast-paced M&A environment, mastering LOI negotiations often determines whether a transaction proceeds efficiently or becomes bogged down in misaligned expectations.

The Grand Slam Strategies

The Rules: Modern transaction documents must address emerging risks and opportunities. Purchase agreements now include detailed provisions for data privacy compliance, intellectual property ownership in AI-developed assets, and specific performance metrics for digital transformation initiatives. Representation and warranty insurance has become standard, typically covering 10% of enterprise value, with a floor of about $5 million. Similar to health insurance, your retention rate (better known as your deductible) will vary depending on the size of the transaction.

The Scoring System:

1. Working Capital Adjustments: Working capital adjustments ensure the business has adequate operational resources at closing. Key elements include, among others, target ranges based on historical averages; specific definitions of included assets and liabilities; pre-closing estimates and post-closing true-up mechanisms; independent accountant dispute resolution procedures; and clear timelines for calculations and challenges. Working capital adjustments should specify target ranges based on historical averages, with detailed mechanisms for resolving disputes through neutral accountants. Strategic escrow arrangements typically hold 10-15% of deal value for 12 to 24 months to address potential breaches of representations and warranties.
2. Escrow Arrangements: Escrow provisions protect buyers against potential breaches of representations and warranties. Generally, 10-15% of total deal value is held in escrow for 12 to 24 months, with specific conditions and timing for releases clearly defined in the agreement. These protection mechanisms require precise drafting and careful negotiation to ensure they serve their intended purpose without creating unnecessary friction in the transaction process. Success lies in balancing protection with practicality, ensuring mechanisms are both effective and executable.
3. Earnouts: The better-known “earnout” provision can be advantageous for both parties involved in an M&A transaction. For the seller, an earnout can maximize the total sale price by tying future payments to the performance of the business, allowing them to benefit from the growth they anticipate. For the buyer, it reduces the upfront capital outlay and aligns the interests of the seller with the continued success of the business post-acquisition. However, earnouts also come with challenges. They can create tension between buyers and sellers regarding the management and direction of the business, as both parties may have different strategies to achieve the performance metrics set forth in the earnout. Since earnouts are typically tied to the final purchase price, it is critical for sellers to negotiate clear operational control and decision-making rights during the earnout period to ensure they can achieve the established targets. This includes detailed provisions regarding management authority over key business decisions, protection against buyer actions that could negatively impact earnout achievement, access to financial information and reporting requirements, clear definitions of how acquisitions or divestitures during the earnout period will be treated, and dispute resolution mechanisms for calculation disagreements.

The World Championship

The Wild Card: Generally, everyone is so focused on the deal terms that they tend to overlook the importance of successful integration post-M&A. Successful integration requires a detailed plan, including specific milestones for IT systems integration, customer relationship management, and employee retention. Research shows deals that spend more than 6% of transaction value on integration efforts achieve significantly better outcomes. Cultural integration deserves particular focus — deals retaining over 90% of key employees show markedly higher success rates than those losing 10-30% of critical talent. In fact, PwC reported that “acquirers that prioritize value creation at the outset can outperform peers by as much as 14 percent.”

Postgame Strategy: The success of an M&A transaction extends well beyond closing, with operational governance documents serving as the critical framework for post-integration success. These documents establish clear protocols for day-to-day operations, decision-making authority, and conflict resolution. Shareholders’ Agreements define fundamental rights and obligations among equity holders, including voting rights, transfer restrictions, and exit mechanisms. Operating Agreements establish the management structure, outlining specific decision-making thresholds and procedures for both routine operations and major corporate actions. The most effective governance documents anticipate potential areas of conflict and provide clear, executable resolution mechanisms, preventing operational disruptions that could derail post-merger value creation. For an in-depth discussion on the role of governing documents, you can refer to our dedicated article here.

The Final Score

M&As are dynamic, complex, and high-stakes transactions that demand the precision of a championship team. The most successful deals, like winning seasons, require careful preparation, strategic execution, and flawless teamwork. By focusing on deal protection, strategic escrows, earnouts, and post-merger governance, parties can maximize value creation and achieve long-term success. Just as championship teams combine talent, strategy, and execution, successful M&A transactions blend careful planning with decisive action. In today’s competitive arena, mastering these elements can mean the difference between hoisting the trophy and watching from the sidelines.

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