Business Law and Transactions Law Blog
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
Business
Before You Exit: Navigating Succession Planning and Growth in Privately Held Companies
The Third Annual Private Business Owner Survey by Brown Brothers Harriman (BBH) is out, and it provides a revealing and timely look into the mindset, priorities, and risks facing today’s private business owners. We're all aware of it by now - the largest cohort of founders and business owners are reaching retirement age. The survey from BBH and findings in the report shed light on the intersection of personal planning and corporate continuity. For business owners, investors, advisors, and those preparing to take the reins, this report offers not just data, but direction. Succession and sustainable growth are clearly interconnected based on the information collected. The BBH report also underscores the importance of understanding the broader exit landscape. In addition to estate planning, it should be considered how search funds, independent sponsors, and family office buyers fit in. As deal volume rises and ownership transitions accelerate, sellers must weigh the nature of their successors just as carefully as the valuation terms. Succession: More Talked About, Still Under-Planned Although 62% of business owners express a desire to pass their business to the next generation, only 23% have taken concrete steps to implement a formal succession plan with key executives. An alarming 30% have no succession plan at all, despite the majority having been in business for decades. The balance (~46%) have some form of succession plan in progress. Key barriers to succession planning were reported to include: Emotional reluctance to step away (28%) Uncertainty over the right successor (41%) Complex family dynamics (46%) The business owner's perception of the successor's preparedness is also likely an issue, where the overwhelming majority reported that the successor is not yet fully prepared. Business owners hope that informal conversations will serve as a roadmap, but the reality is far less forgiving. Without clear documentation and defined leadership roles, businesses face confusion, instability, and risk of value erosion during a transition. Succession isn’t a one-time event - it’s a process requiring candid conversations, objective planning, and consistent follow-through. This is where search funds and independent sponsors can play a unique role. These buyers, often backed by seasoned investors or family offices, are well-positioned to acquire and operate businesses where no natural successor exists. Their appeal lies in their hands-on involvement, long-term view, and ability to step into the role of owner-operator while respecting the legacy of the founder. This also ties into the critical question of estate planning. The BBH report found that of the 70% of business owners with an estate plan, 76% will be using a trust. Growing and Sustaining: A Top Priority with Diverging Paths A strong growth mindset persists among private business owners. 78% of respondents prefer reinvestment and long-term growth over extracting profits or maintaining full ownership. However, this growth focus can lead to diverging opinions within ownership groups, especially when generational views or risk tolerances differ. The survey revealed that while 59% of owners believe their leadership teams are very well aligned on business strategy, 32% admitted to only moderate alignment. That misalignment can be costly—it often leads to stalled initiatives, delayed decision-making, and increased friction over strategic direction. To support growth, owners are considering various funding strategies: 69% plan to use traditional bank financing 30% are open to family office partnerships 20% are exploring private equity as a source of growth capital Still, the most commonly cited barrier to external capital is loss of control. Many owners fear that selling equity or bringing in new stakeholders may compromise their values, culture, or influence. However, those who thoughtfully structure outside capital arrangements may find they unlock opportunities that far exceed the costs. It’s worth noting that the search fund (ETA) and independent sponsor space is seeing a sharp uptick in activity, with many of these buyers receiving funding from family offices and specialty investors. Many of these groups offer capital and continuity without the pressures of a traditional private equity exit cycle. Some family offices are combining direct investment strategies with multi-generational wealth management, leading them to become increasingly active in small and mid-market acquisitions. The Legacy Lens: Transcending the Exit Succession is not simply about exiting the business or passing on shares. It’s about defining and preserving a legacy that goes beyond spreadsheets and valuations. Owners in the BBH survey expressed deep commitments to continuity. They desire to see family harmony, company culture, employee loyalty, and community impact. These “soft” values often matter just as much as legal or tax considerations. To preserve legacy and sustain the business beyond the current generation, owners must: Foster regular dialogue with heirs and management teams Evaluate successor readiness across leadership roles Introduce outside advisors who offer perspective and neutrality Reassess governance frameworks to support long-term strategy Document as much as possible Moreover, it’s vital to build structures that allow next-generation leaders to grow into their roles while being mentored by the outgoing generation. Done well, this approach creates both continuity and momentum. Preparing the Business, Not Just the Owner: Legal Review Succession planning is as much about preparing the business as it is about preparing the people. Even the most well-intentioned plan will falter if the company’s infrastructure, processes, or governance can’t support new leadership. Important readiness steps include: Reviewing key contracts for assignability or change-of-control clauses Establishing clear reporting systems and operational playbooks Addressing concentration risks (customer, supplier, key employee) Implementing equity compensation or retention plans for critical staff Transition planning should include a full enterprise audit of both legal and operational functions of the business to ensure the next owner or leader inherits a stable foundation. This level of diligence is especially critical in independent sponsor or search fund transactions. Buyers in these transactions often inherit businesses with informal structures or legacy systems that require immediate modernization. Business owners planning an exit should prepare for this scrutiny and invest in proactive documentation and governance to avoid valuation discounts or deal delays. This will also help the business command a higher valuation. Final Thoughts Whether your long-term vision includes a family transition, a management buyout, or a strategic sale to a search funder or family office, the path forward must be deliberate. Integrating succession with growth planning is key to protecting enterprise value and maintaining continuity. Planning early provides more flexibility, more stakeholder buy-in, and ultimately, a smoother transfer of both ownership and leadership. The BBH survey reveals a growing awareness of these issues, but this awareness must also be followed by action. Fortunately, a wide range of advisors, tools, and capital partners are now supporting business owners through these pivotal moments. Read the full BBH report here: BBH Thid Annual Business Owner Survey
November 14, 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
The SMB Market Is Moving: Record SBA Lending, Strong Deal Flow, and What It Means for Buyers
According to the latest BizBuySell report, Q3 2025 saw 2,599 small business sale transactions. This is an 8% year-over-year increase and 11% growth over Q2. Data also shows a steady wave of buyers are seeking the right opportunity to operate and grow established businesses. In parallel, the Small Business Administration (SBA) was on pace to close $4.8 billion in loan approvals before the federal shutdown temporarily paused operations. This is the highest volume of capital deployed to small businesses in a single fiscal year. That includes over 84,400 7(a) and 504 loans, amounting to 1,600 loans a week. The appetite is clear. What’s Fueling the Market? Despite macroeconomic pressures (inflation, tariff-driven supply costs, etc.), many buyers remain focused on long-term fundamentals. The median sale price for a business this quarter was $320,044, down slightly from last year. This is likely a lower sale price than many Searchfunders/Independent Sponsors are targeting, but the data also shows a shorter time on market (149 days), evidencing strong buyer demand. Essential services were the leading category of sales. I work with buyers, investors, and operators on a daily basis. Here is what I am noticing: These Are Small Businesses — Not Just Small Corporations Many of these deals involve main street and lower middle market businesses, where the seller is not just the owner — they’re often the primary operator, manager, and customer relationship lead. This model can work well, but it’s important for buyers to go in with eyes wide open. These are not absentee owner businesses. These are owner-operator businesses, and unless the buyer has a plan to step into the day-to-day, or grow and install leadership, the absence of middle management may lead to significant demands on the business owner's time. Diligence Is Critical — Especially for Deals at or below $1 Million Buyers and advisors need to scrutinize: Owner reliance — Will customer or vendor relationships walk out the door post-close? Documentation gaps — Are there written contracts? Employment terms? Assignable leases? Many of these businesses fail to properly maintain documentation. Employee risk — What’s the true culture, compensation model, and turnover rate? System maturity — Is there any standardization, or will you be rebuilding ops from scratch? The Desire to Own Must Match the Business Type Entrepreneurship through acquisition (ETA) is a powerful path. But not every business fits every buyer. I always advise clients to ask: “Do I want to run this business, or do I just want to own it?” In the start-up world this is called "founder-market fit." The same concept applies here. Some deals are perfect for someone who wants to buy a job and eventually grow it. Others might require an immediate team build or capital outlay to systematize operations. It’s critical to understand the type of role you’re buying into, the basics of the industry, and what that means when operating solo or with lean support. Deals Are Happening — But You Need the Right Team This market shows real momentum. That being said, deals still require precision. That means: Structuring with SBA or seller financing Negotiating reps, indemnities, and transition terms Performing adequate due diligence Aligning tax, legal, and operational diligence Preparing to serve as both the owner and the operator (or installing trusted leadership) I work closely with searchers, independent sponsors, and advisors both during the acquisition and long after the closing. From real estate and contracts to employee issues and outside general counsel support, you need the support to manage the risk and build the value. It is exciting to see the growing volume of deals and buyer interest. But remember not to lose sight of the need to find the right acquisition target and to protect your downside.
October 23, 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
Business
Non-Compliance with CMMC Could Put Your DoD Contracts at Risk
This past month, the Department of Defense sent the final rule for the new Cybersecurity Maturity Model Certification (CMMC) program under the Federal Acquisition Regulation to the Office of Information and Regulatory Affairs for review. This action precedes the inclusion of the new rule in Department of Defense contracts beginning this autumn. So, it is time to get into compliance for all who have been delaying the inevitable. Below is a quick review of these requirements. Background CMMC is designed to bolster the cybersecurity posture of the DoD’s supply chain by validating that DoD contractors and subcontractors possess the necessary cybersecurity practices and processes to safeguard Federal Contract Information (FCI) and various kinds of Controlled Unclassified Information (CUI). CMMC introduces a tiered, certification-based approach, ranging from Level 1 (basic cybersecurity practices for FCI) to Level 2 (advanced practices for most CUI), and Level 3 (expert practices for sensitive CUI). Why is This Important? Contractors and subcontractors must attain the appropriate CMMC level aligned with the security requirements of their contracts to bid and work on DoD projects. In addition to the cybersecurity and reputational risks of non-compliance, if contractors and subcontractors fib or cut corners, they could face False Claims Act (FCA) liability, including draconian damage and penalty assessments. One disgruntled employee who decides to bring an FCA complaint can cost a company significant pain. Contracts Covered by CMMC The CMMC requirement applies to DoD acquisitions that involve the handling of FCI and CUI. Major Contract Programs: Contracts for the procurement of defense systems, weapons, military equipment, and related services that require access to CUI or FCI will be directly impacted. This includes a broad spectrum of procurement categories across the DoD, from large-scale hardware contracts to software development and services. Subcontractors and Supply Chain: Importantly, the rule also extends to subcontractors at all tiers. This flow-down creates a ripple effect throughout the defense supply chain. Contracts Not Subject to CMMC While the rule is broad, it does not universally apply to all federal contracts. FAR Part 12 Commercial Item Contracts: Some commercial item contracts purchased under FAR Part 12 may be excluded unless the scope involves sensitive information or national security concerns. Contracts with No Access to CUI or FCI: Contracts that do not involve access to or handling of CUI/FCI will not be subject to CMMC requirements. Other Exceptions: The FAR Council has provisions for exemptions for technical or administrative reasons, but these are limited and require justification. What is FCI If you are a contractor or subcontractor that handles controlled information such as CUI, you likely have some sophistication regarding cybersecurity. But those with FCI may not be aware that they have protectible information, and most medium and larger-sized DoD contracts will have FCI. FCI refers to information that is not intended for public release but is provided by the federal government to a contractor or subcontractor for the purpose of fulfilling a federal contract. It includes data that is critical to the performance of government contracts. Examples include technical data (e.g., details about a supplier’s hardware specifications), contract schedules and milestones (e.g., timelines for delivering military equipment), and financial or administrative information shared with contractors. Typical Contracts:Smaller contracts Basic supply chain activities FCI Requires Level 1: Basic Cyber Hygiene Key Requirements: Implementation of basic controls, including access only by authorized users, maintaining identification and authentication, and physical protection of information systems. Practices include routine login credentials, portable device protections, and basic awareness training. Annual self-assessment and annual affirmation of compliance with CMMC requirements. What is CUI It’s not classified information, but it is information that requires safeguarding pursuant to various laws, regulations, and government policy. Examples include information about physical security, system vulnerability, or operational issues. CUI Requires Level 2 (Intermediate) or Level 3 (Expert) Processes Level 2: Intermediate Cyber HygienePractices: 110 practices, aligned with NIST SP 800-171 security requirements. Focus: Establishing more disciplined cybersecurity processes and practices suitable for organizations handling CUI. Third-party assessments are required for certification at this level. Level 3: Expert Cyber HygienePractices: Over 130 security controls, closely aligned with NIST SP 800-171, plus some additional practices. Focus: A mature, enterprise-wide cybersecurity program. This will apply only to a limited number of contractors with larger, more sensitive defense contracts that require higher levels of CUI protection. Third-party assessment is required.
August 27, 2025
Business
Business Tax Law Provisions of the OBBBA
The business tax provisions of the One Big Beautiful Bill Act (OBBBA), as signed by the president on July 4, reflect sweeping changes aimed at incentivizing small businesses, domestic investment, and manufacturing. Outlined below are key provisions of the bill that may impact your business. Extension and Enhancement of Immediate Expensing 100% Immediate Expensing for Qualified Property OBBA permanently reinstates 100% bonus depreciation for eligible business property acquired after January 19, 2025. Immediate Deduction for Domestic Research and Experimental Expenditures Immediate expensing of domestic research and experimental expenditures is now permanent, with an election to amortize certain expenditures. Permanent Small Business Deduction (Section 199A) Section 199A Deduction Made Permanent The 20% deduction for qualified business income (QBI) for pass-through entities is made permanent. The deduction remains at 20%, with expanded phase-in thresholds and an inflation-adjusted minimum deduction for taxpayers with at least $1,000 of qualifying income from active trades or businesses. Increased Expensing for Depreciable Business Assets Section 179 Expensing Limits Raised The maximum amount a taxpayer may expense under Section 179 is increased to $2.5 million, with a phase-out threshold of $4 million, both indexed for inflation. Modification of Business Interest Deduction Business Interest Expense Deduction Expanded The calculation of adjusted taxable income (ATI) for business interest deduction purposes is permanently based on EBITDA, increasing the amount of deductible business interest. Special Depreciation Allowance for Production Property Immediate Deduction for Qualified Production Property Businesses may elect a 100% bonus depreciation deduction for qualified production property placed in service after enactment and before January 1, 2031. Renewal and Enhancement of Opportunity Zones Second Round of Opportunity Zones (OZs) A new round of Opportunity Zones is created, with at least 33% of OZs designated as rural. Enhanced benefits for rural Qualified Opportunity Funds (RQOFs) are included, with a 30% step-up in basis after five years. Expanded Low-Income Housing and New Markets Tax Credits Low-Income Housing Tax Credit (LIHTC) Reforms The state housing credit ceiling is temporarily restored and increased for 2026–2029. Permanent Extension of New Markets Tax Credit (NMTC) The NMTC is made permanent, with a five-year carryover of unused limitation. Permanent Excess Business Loss Limitation Excess Business Loss (EBL) Rules Made Permanent The limitation on excess business losses for noncorporate taxpayers is permanent, with carryforwards treated as net operating losses (NOLs). Estate and Gift Tax Exemption Increased and Made Permanent The estate and lifetime gift tax exemption is permanently set at $15 million for single filers ($30 million for married couples), indexed for inflation. State and Local Tax (SALT) Deduction Changes The SALT deduction cap is temporarily increased for 2025 to $40,000 ($20,000 for married filing separately), with a permanent increase to $40,400 starting in 2026, subject to income limitations and phase-outs. For taxable years beginning after December 31, 2029, the limitation reverts to $10,000. Section 707(a)(2) Partnership Changes Allocations and distributions from partnerships that are, in substance, payments for property or services are now treated as such, rather than as allocations and distributions from a partnership to a partner. This codifies the disguised sale rules without reliance on regulations and applies to services performed and property transferred after enactment. The following “Quick at a Glance” table distills each major OBBBA business‑tax change into a concise, one‑line summary of its scope, benefits, and effective dates. SUMMARY TABLE: Major OBBBA Business Tax Provisions (as Amended) Provision Key Change/Benefit 100% Bonus Depreciation Permanent for eligible property. Section 179 Expensing $2.5M limit, $4M phase-out, indexed. Section 199A Deduction Permanent at 20%, broader phase-in, inflation-adjusted minimum. Business Interest Deduction Permanent EBITDA basis. Opportunity Zones New round, rural focus, enhanced rural benefits. LIHTC/NMTC Increased/extended, NMTC permanent, rural/Indian prioritization. Excess Business Loss Limit Permanent, NOL carryforward. Estate & Gift Tax Exemption $15M/$30M, indexed. SALT Deduction Cap increased to $40,000/$40,400, reverts to $10,000 after 2029. Section 707(a)(2) Disguised sale rules codified, applies to property/services after enactment.
July 8, 2025
Business
Maryland’s Sales Tax on IT Services: Key Insights and Compliance Tips
As part of its 2025 Budget Reconciliation and Financing Act, Maryland is introducing a 3% sales and use tax on a broad range of information technology (IT) services, effective July 1, 2025.[1] This “tech tax” is designed to modernize the state’s tax base and capture revenue from the rapidly expanding digital economy. The new law will impact service providers and purchasers across sectors, requiring careful attention to compliance and timely updates to accounting and billing systems. Scope of the New Tax The tax applies to IT and data services classified under specific North American Industry Classification System (NAICS) codes: 518 (data processing, hosting, and related services), 519 (web search portals, libraries, archives, and other information services), 5415 (computer systems design and related services), and 5132 (software publishing services). Covered services include cloud storage, web and server hosting, SaaS offerings, IT consulting, custom software development, and more.[2] Notably, the law eliminates the prior exemption for custom software and related services, meaning that even fully customized solutions, regardless of delivery method, are now taxable.[3] The tax rate is set at 3%, unless the service qualifies as a digital product or tangible personal property, in which case the standard 6% rate applies. Clarifications from Maryland Technical Bulletin No. 56 Maryland Technical Bulletin No. 56, published June 10, 2025, provides essential clarifications on the new sales and use tax for IT services. The Bulletin explicitly states that taxability is determined by the nature of the service provided, not the primary NAICS code reported by the business for federal or state income tax purposes. Each service must be evaluated individually against the NAICS activity descriptions for data or IT services and software publishing as defined by Maryland law.[4] For example, even if a business’s primary NAICS code is not one of the specified codes, any services it provides that fall under NAICS sectors 518, 519, 5415, or 5132 are subject to the 3% tax. Similarly, the NAICS code listed in a procurement contract is not determinative; taxability is based on the actual service provided.[5] The Bulletin also clarifies that the tax applies to internal services provided by one affiliated company to another, even if provided at cost, unless a specific exemption applies. Regarding timing, the Bulletin explains that for subscription-based services, each payment after July 1, 2025, is considered a separate sale and is taxable. However, installment or credit sales where the contract was executed before July 1, 2025, are generally not taxable, even if payments are made or services are delivered after that date.[6] Change orders expanding the scope of services after July 1, 2025, are considered new sales and are taxable.[7] Compliance and Exemptions Businesses must register for a Sales and Use Tax (SUT) license and prepare to collect and remit the new tax. The law provides exemptions for certain research and development contracts, such as those involving the University of Maryland’s Discovery District and its quantum computing partners.[8] Additionally, for services used simultaneously in multiple jurisdictions, buyers can provide a Multiple Points of Use (MPU) certificate, shifting the tax remittance responsibility to the buyer, who must apportion the tax based on Maryland usage.[9] Impact and Next Steps Maryland’s new tax on IT services marks a significant shift in the state’s approach to taxing the digital economy. It is expected to increase costs for both providers and purchasers of IT services, particularly in the technology, finance, and government contracting sectors. Businesses should review their service offerings, update compliance protocols, and use guidance from the Comptroller’s Office to ensure smooth implementation. Key Takeaways Effective Date: July 1, 2025 Tax Rate: 3% on qualifying IT and data services Covered Services: NAICS 518, 519, 5415, and 5132 Clarifications: Taxability determined by service, not business NAICS code; applies to internal and affiliate transactions; timing rules clarified for subscriptions, installments, and change orders. Compliance: Register for SUT license, review service offerings, and prepare to collect/remit tax. Exemptions: Research contracts with University of Maryland Discovery District; MPU certificates for multi-jurisdictional use. By proactively addressing these changes, businesses can minimize disruption and ensure compliance with Maryland’s new sales tax on information technology services. [1] “Budget Reconciliation and Financing Act of 2025” (“BRFA”), H.B. 325, 2025 Leg. Sess. (Md. 2025). [2] Comptroller of Maryland, Sales and Use Tax on Data or Information Technology Services and Software Publishing Services: Questions and Answers, Tax Bulletin No. 56 (June 10, 2025) (the “Maryland Technical Bulletin No. 56”). [3] See Maryland Technical Bulletin No. 56 para I. A. 7. [4] See Maryland Technical Bulletin No. 56 [5] See Maryland Technical Bulletin No. 56 Q&A I. A. 2. [6] See Maryland Technical Bulletin No. 56 Q&A II. C. 13. and 14. [7] See Maryland Technical Bulletin No. 56 Q&A II. C. 16. [8] See Maryland Technical Bulletin No. 56 Q&A III. B. 27. [9] See Maryland Technical Bulletin No. 56 Q&A III. C.
July 1, 2025
Business
AI Reps & Warranties: Emerging Issues in Deals and Commercial Contracts
Artificial intelligence quickly became embedded into business operations, software platforms, internal workflows, and consumer-facing applications. This means the legal risks associated with its development and growth are moving from the abstract to the real world. AI is not only changing how businesses operate, but also how leaders and legal practitioners must structure and negotiate contracts. Legal teams, in-house counsel, and M&A deal professionals can no longer consider this a niche issue and should consider it a negotiated deal point involving risk allocation, liability exposure, and asset valuation. While there is significant attention paid to the disruptive operational power of AI, its implications on representations and warranties in commercial agreements and corporate transactions deserve just as much attention within the legal community. Some tailored legal frameworks are already emerging to address the novel concerns around data privacy, intellectual property, indemnity, and operational continuity. These issues are especially critical in the context of software acquisitions, SaaS contracts, and any M&A deal involving AI-derived intellectual property or business processes. AI-Specific Representations in Deals The National Venture Capital Association (NVCA) model forms were updated at the end of 2024 to incorporate AI-specific representations and warranties. These terms are increasingly reflected in market practice: Targets must affirm that AI tools were used in compliance with applicable licenses, regulations, and data use agreements. Targets must represent that they did not input any personal, confidential, or protected information into AI tools, unless those tools guarantee that such data is not used for training or product enhancement. Targets must represent that data was deidentified or anonymized prior to use in training models to avoid running afoul of applicable data protection standards. Targets must disclose any generative AI platforms used to develop proprietary IP and warrant that such use does not jeopardize any ownership rights being acquired. The above issues are only the tip of the iceberg. Transactions and agreements involving complex AI products must include increasingly technical reps concerning: Model training logs and documentation Fine-tuning methods and retention of model weights Mechanisms used in retrieval-augmented generation (RAG) Use of synthetic or auto-generated content in commercial workflows Model validation performance thresholds, including floating point operation limits and accuracy ranges As the technology matures, the legal community is catching up by embedding operational guardrails directly into transactional documentation. Practical Contractual Risk Areas in AI Licensing Commercial licensing agreements involving AI must now be viewed through a much more detailed legal lens. Counsel should be prepared to negotiate contract terms specifically addressing: Non-infringement guarantees concerning both source code and training data, especially where data scraping or aggregation may have occurred Explicit ownership claims over AI outputs, derivatives, and model weights Training data auditability, including the legal basis for data collection, classification, and labeling Compliance with global privacy and cybersecurity laws, including GDPR, CPRA, and HIPAA when applicable Robust indemnification obligations for breaches of data usage restrictions, IP violations, or algorithmic harms Tech E&O and cyber liability insurance provisions, ensuring recourse exists if generative tools malfunction, hallucinate, or produce defamatory content In many cases, the liability profile of AI is uncertain and difficult to quantify. Because many models operate as "black boxes," licensees are often left without a clear explanation of how certain outputs were generated or what datasets were used in training. This makes traditional warranties about performance or fitness for a particular purpose difficult to enforce. As a result, buyers and licensees are demanding broader representations, heightened disclosure obligations, and post-closing audit rights to mitigate these unknowns (while sellers are seeking to disclaim warranties and narrow representations). M&A and AI Due Diligence AI risk has quickly become a key diligence category in M&A deals, especially in transactions involving software, e-commerce, analytics, or consumer engagement platforms. Buyers are now expected to conduct diligence not just on IP rights and customer contracts, but also on how AI has been implemented and governed. Pre-Acquisition Diligence Key diligence areas include: Training data sourcing: Was the data obtained lawfully and under enforceable terms? Privacy risk: Was any personally identifiable information (PII) used in training or prompting without consent? Third-party code and APIs: Does the AI product depend on third-party components that might limit assignability or trigger license fees? Model update and retraining rights: Who controls the model lifecycle, including patches and performance tuning? Export control risks: Could the AI model be subject to ITAR, EAR, or other national security controls due to its capabilities? Post-Closing Continuity Buyers should also require: Complete AI architecture diagrams and component inventories Documentation of ethical safeguards and bias mitigation processes Retention policies around input prompts and AI-generated output logs Model deployment playbooks and downtime risk disclosures Transition services agreements, software escrow, and founder retention may also be needed to ensure business continuity and proper knowledge transfer where AI is a critical but complex asset. IP, Privacy, and Employment Triggers This isn't only an issue for "tech transactions." As AI expands across business functions, its legal implications multiply. Core issues include: Intellectual property ownership, particularly whether AI-generated outputs are protectable under U.S. copyright law or must be secured as trade secrets Privacy and cybersecurity risks stemming from unstructured data ingestion and prompt leakage, especially when sensitive information is processed or used Employment law exposure, including discriminatory hiring algorithms or opaque automated decision-making processes that may violate EEOC or state-level labor rules Recent case law and regulatory action suggest that companies using AI for decision-making will be held to explainability and fairness standards, even if they do not fully control or understand the model. Additionally, companies leveraging AI in consumer products or safety-critical environments must consider product liability exposure under traditional tort theories, especially if AI contributes to physical or economic harm. Think about the auto-driving taxi that must decide whether to hit the pedestrian or crash the car. AI and IP Security Agreements As more companies develop proprietary AI tools, models, and datasets, lenders and investors are increasingly taking security interests in these intangible assets. This requires a rethinking of traditional IP Security Agreements. When collateral includes AI-generated or AI-driven intellectual property, legal teams should evaluate: Whether model weights, training datasets, or prompt libraries are clearly documented and listed as pledged assets Whether the borrower can demonstrate ownership and provenance of the training data and model code If the model is fine-tuned from a third-party foundation model, whether the underlying license permits encumbrance or assignment If retrieval-augmented generation (RAG) is used, whether the underlying corpuses and connectors are part of the security package The existence of source code escrow to ensure access in the event of default or bankruptcy Any restrictions in open source or SaaS agreements that may limit foreclosure or reassignment rights Moreover, the lender’s enforcement rights may be limited if the AI model or data is co-owned, cloud-hosted, or reliant on third-party APIs. Security interests must be carefully drafted to reflect operational dependencies, and perfection of those interests may require filings beyond the USPTO, including notice to cloud vendors or consent from licensors. IP Security Agreements for AI assets must go beyond standard boilerplate and should be tailored to the unique hybrid nature of AI systems combining software, services, and data streams. In many cases, a supplemental AI-specific collateral schedule may be appropriate. Takeaways for Legal and Deal Teams AI is no longer a novel technology element to be glossed over in standard reps and warranties. It is a high-stakes business driver that intersects with every major legal category: IP, privacy, cybersecurity, employment, antitrust, and contract liability. Actionable takeaways include: Draft AI-specific reps and warranties that cover data sourcing, training protocols, model rights, and use case restrictions Build diligence frameworks that include discussions with technical teams and review of logs, policies, and product roadmaps Negotiate indemnification mechanisms that allocate financial risk from misuse, error, or regulatory exposure Ensure insurance provisions cover AI incidents, from hallucinated content to data leakage Establish post-closing governance and monitoring structures, particularly in acquisitions involving live AI models or mission-critical algorithms Review and update IP Security Agreements to specifically address AI collateral and embedded third-party dependencies Ultimately, the central legal question becomes: When AI makes a mistake, who pays? Whether drafting a commercial SaaS agreement or executing a strategic acquisition, every deal team must be ready to answer that. As legal and technological standards continue to evolve, ongoing adaptation will be essential.
June 19, 2025
Business
Pennsylvania Limits Non-Compete Agreements for Health Care Practitioners
In July 2024, Pennsylvania Governor Josh Shapiro signed House Bill (HB) 1633, the Fair Contracting for Health Care Practitioners Act (the "Act"), into law. In summary, the Act: (1) limits the enforceability of non-competes against certain health care practitioners; and (2) imposes a notice obligation on employers of those practitioners. The Act became effective on January 1, 2025. The purpose of this article is to revisit this important legislative development in its first year of existence, given its potential to significantly impact the health care landscape. Here is a breakdown of the Act changes, including who it covers, its application in case law, and its potential impact on physician and other clinical professional employment contracts across the Commonwealth. Limits on Non-Competes The Act renders unenforceable non-compete covenants with a duration longer than one year for certain health care practitioners, subject to the following caveats: The Act only applies to “health care practitioners,” which the Act defines to include “medical doctors,” “doctors of osteopathy,” “certified registered nurse anesthetists,” “certified registered nurse practitioners,” and “physician assistants,” as those terms are defined in other Pennsylvania statutes. The Act only applies to “non-compete covenants,” defined as agreements between an employer and a health care practitioner that “has the effect of impeding the ability of the health care practitioner to continue treating patients or accepting patients.” Notably, the Act does not apply to other post-employment restrictive covenants, such as confidentiality provisions and employee non-solicitation clauses. The Act does not prohibit employers from enforcing non-competes with a duration of one year or less, provided that the employer did not terminate the health care practitioner’s employment without cause. This means that employers cannot enforce a non-compete against health care practitioners who are terminated without cause, regardless of the duration of the covenant. The Act is silent as to whether Pennsylvania courts may reform overbroad non-competes. Presumably, that decision is still within the discretion of the court. The Act does not apply to non-competes entered into in connection with the sale of a business or grant of equity, provided the health care practitioner was a party to the transaction. The Act becomes effective on January 1, 2025. Importantly, it does not apply retroactively. That means that non-compete agreements entered into with health care practitioners prior to the effective date will remain enforceable, subject to existing requirements under Pennsylvania law. Notification Requirement The Act also imposes a patient notice requirement on employers of health care practitioners. Within 90 days of a health care practitioner’s termination of employment, employers must notify the separated practitioner’s patients: (1) of the practitioner’s departure; (2) if the patient chooses to receive care from the departed health care practitioner or another health care practitioner, how the patient may transfer their health records to that provider; and (3) that the patient may be reassigned to another practitioner in the employ of the employer if the patient wants to continue treatment with the employer. Importantly, this notification obligation applies regardless of whether the separated practitioner is subject to a non-compete. In addition, an employer is required to provide these notifications within 90 days of the health care practitioner’s departure. However, the notification requirement applies only where the health care practitioner had an ongoing outpatient relationship with the patient for two or more years. Existing Case Law & Precedents Pre-Act Foundation: WellSpan Health v. Bayliss (2005) Under Pennsylvania common law, courts evaluating physician non-competes traditionally balance public interest—particularly patient access to care. In WellSpan Health v. Bayliss, the Commonwealth Court emphasized that ensuring patients can continue treatment is paramount when deciding whether to enforce restrictive covenants law. While predating the Act, this ruling sets the tone: Pennsylvania courts lean toward protecting continuity of care when non-competes might limit it. Post-Act Litigation: Thakkar v. AHN (2025) Shortly after the Act took effect, gastroenterologist Dr. Thakkar challenged Allegheny Health Network (AHN) in the Allegheny County Court of Common Pleas. After AHN declined to renew his contract, Dr. Thakkar stated that the existing non-compete prevented him from practicing in the same region, which disrupted patient care. Although the trial court sided with AHN, Thakkar has appealed to the Pennsylvania Superior Court. His argument underscores the Act’s protections: non-competes imposed post‑January 1, 2025, should be void if the practitioner is dismissed. Open Issues Under the Act The Act does not define many terms and is such a hodgepodge of concepts and requirements that it could be a health care employer's nightmare. Some unanswered questions include: Are reasonable non-compete covenants enforceable where the health care practitioner receives a tiny “ownership interest”? Are non-compete covenants effective for more than one year enforceable where an employment agreement is not renewed? Will a patient non-solicitation provision be included within the scope of the Act? Is the patient notice requirement triggered regardless of the reason for the end of the employment relationship? Does the death or retirement of a health care practitioner trigger a potential notice requirement? Is the patient notice requirement necessary where the health care practitioner is employed for only 23 months (i.e. two years)? How is patient notice accomplished? Is a website posting sufficient? Is there any penalty for noncompliance? The Act reflects a trend in states across the U.S. focused on promoting physician mobility and improving patient access to care, while raising important compliance considerations for hospitals, health systems, medical practices, and their legal teams. For physicians and other clinical professional employers, the Act presents both compliance challenges and the need for directional shifts. Employment contracts will need to be revised, and retention strategies will need to pivot from focusing on legal restrictions to emphasizing purposeful engagement, such as competitive compensation, workplace culture, or career growth opportunities.
June 18, 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
Business
Avoiding Common Contract Pitfalls: Legal Landmines in Agreements
Contracts are the backbone of every business relationship. Whether buying a business or entering into a new commercial agreement, many small to mid-sized businesses do not fully negotiate critical clauses within the document. Failing to fully negotiate certain language, relying on informal agreements, or failing to update commercial contracts with appropriate amendments as the relationship evolves can become a significant liability to a company. Informal arrangements may feel efficient in the short term but can create significant issues if a dispute arises. In this edition of Search Fund Operate, we break down the most commonly negotiated (and litigated) provisions in contracts. The below is an overview of how acquirers, operators, and business owners can proactively protect themselves from exposure. The Risk of Informal Agreements Many business relationships begin with trust — a handshake deal, an email exchange, or a PDF template someone downloaded online years ago. But when disputes arise, courts look for formal agreements. Informal or undocumented agreements often lack enforceable provisions around risk allocation, dispute resolution, and payment mechanics. Even worse, they often fail to outline each party’s actual responsibilities, deadlines, or remedies. Tip: If a dispute reaches litigation, and there is no signed agreement or only partial documentation, courts may rely on the parties' prior conduct or applicable statutory rules that might not reflect the parties’ original intentions. Inconsistencies can lead to conflicting testimony and unpredictable results. Without formal terms, operators risk operational confusion and disruptions, customer dissatisfaction, and expensive court battles. This risk grows exponentially when the business is being sold or scaled, as buyers expect to inherit clear, enforceable rights and obligations. Liability and Indemnification Indemnification Clauses Indemnity provisions shift the burden of financial responsibility for specific claims. These are some of the most heavily negotiated clauses. Poorly drafted clauses can: Leave you liable for the other party’s negligence or misconduct. Fail to include third-party claims (e.g., customer injuries from vendor products). Omit procedural requirements for notice and defense, leaving you without control of litigation that affects your reputation. Tip: Ensure that the indemnification clause is protective of your interests. Push for mutual indemnification, defense, and settlement rights, not just reimbursement. Also consider whether to limit indemnification to direct damages or extend it to consequential losses. Environmental Indemnity In certain industries — such as manufacturing, logistics, or commercial real estate — environmental risk requires special attention. Contracts should: Clearly allocate responsibility for environmental conditions, both known and unknown. Include representations about compliance with environmental laws and past environmental issues. Address remediation costs and third-party claims. Tip: Require the disclosing party to provide environmental reports and clarify who bears responsibility for pre-existing contamination. Liability Carve-Outs Clauses that attempt to shift risk should specify whether they cover negligence, gross negligence, or willful misconduct. The broader the language, the greater the protection. Sophisticated parties often negotiate carve-outs for fraud or breaches of confidentiality. Limitation of Liability: Know Your Exposure Exclusion of Damages Most contracts attempt to exclude certain categories of damages: Consequential damages (e.g., lost profits or reputational harm) Incidental damages (e.g., additional shipping or handling costs) Punitive damages (rare, but potentially significant in litigation) However, these clauses must be: Clearly drafted and conspicuously presented in the agreement Consistent with governing law and not prohibited by statute Tied to specific breaches or defined categories of claims Tip: Courts may strike down limitation clauses if they are hidden in boilerplate language or conflict with public policy (e.g., consumer harm or gross negligence). Careful drafting is necessary to ensure these clauses are enforceable. Caps on Damages Liability caps are common. These are often limited to: The total fees paid under the agreement over a certain period A multiple of the monthly or annual contract value These types of damages caps should be: Commercially reasonable Include carve outs for egregious conduct (e.g., fraud, IP infringement) Reviewed for enforceability in high-risk jurisdictions (such as California or New York) Tip: Combine caps on damages with tailored indemnification clauses and insurance requirements offer the most balanced protection. Right to Recover Damages Parties should not assume that silence on damages means full recovery. Contracts should affirmatively state: Whether consequential or incidental damages are recoverable Whether lost profits are compensable Whether the right to injunctive relief is preserved for breaches such as misuse of IP, confidential information, or violation of non-competes (if included and within a jurisdiction where enforceable) Tip: Courts can be reluctant to award damages not clearly contemplated in the contract language. Assignability and Change of Control An often overlooked provision is whether contracts can be assigned to another party — a crucial issue during a business sale or restructuring. If assignment is restricted, it may require: Written consent from the counterparty Disclosure of assignee's financial information Attorney fees associated with any legal review prior to consenting to the assignment Some contracts even treat a change of ownership or control as a default or termination trigger. Tip: Failing to secure assignability can delay or derail an acquisition, especially if key customer contracts are involved. Operators should inventory and review top agreements well before a contemplated sale. Payment Terms and Dispute Mechanics Clear Payment Language Contracts should specify: Invoice frequency and delivery method Payment deadlines, accepted payment methods Grace periods, late fees, and interest charges Whether payments are conditional on acceptance, delivery, or milestones Right to stop future delivery of services or products in the event of non-payment Vague or missing language around payment terms is a common source of cash flow disruption. Courts often apply standard practices or industry norms — which may not reflect your business model. Tip: Use net terms that clearly reflect the payment terms. Add provisions for disputed invoices and partial payments. Condition of Delivered Goods or Services Ensure the contract addresses: Acceptance criteria and inspection periods What constitutes a material defect Remedies for nonconforming or damaged goods Whether services must meet a defined performance standard Tip: If materials are delivered late or defective, and the contract is silent, the buyer may have limited options to reject or recover costs. Dispute Resolution Well-structured dispute resolution clauses can minimize litigation costs and clarify where and how conflicts are resolved. These clauses should address: Venue and jurisdiction Governing law (state of choice) Mediation or arbitration requirements before litigation Scope of issues subject to arbitration Tip: Choose arbitration only when you can afford and control it — not all arbitration is cheaper or faster than court. Choice of Law and Venue Failing to specify a governing law can create confusion and increase cost. Choose a state with predictable case law and commercial friendliness Clarify venue for both lawsuits and arbitration (county and state) Tip: Courts generally uphold these clauses, but ambiguity can invite satellite litigation over which rules apply. Recovery of Attorneys’ Fees By default, parties generally pay their own legal fees unless the contract provides otherwise. A prevailing party clause can: Deter frivolous lawsuits Improve recovery leverage for the aggrieved party Help offset enforcement costs in breach scenarios Tip: Ensure the clause clearly defines "prevailing party" and whether partial victories count. Other Heavily Litigated Provisions Force Majeure Since COVID-19, courts have closely scrutinized force majeure clauses. These should be specific and include: Pandemics, epidemics, and public health emergencies Cybersecurity incidents and data breaches Labor strikes, natural disasters, and government actions Tip: Clarify notice requirements and what obligations are suspended or excused. Termination Rights Contracts should clearly state: Whether either party may terminate for convenience Grounds for termination for cause (e.g., material breach, insolvency) Required notice periods Obligations upon termination (e.g., final payments, transition support) Tip: Courts often look to see if the termination provisions were exercised in good faith and consistent with the contract’s intent. Integration Clause A merger or integration clause ensures that only the written agreement governs the relationship. This is a critical protection against claims of oral promises or email side agreements that contradict the final document. Conclusion Contracts are not just formalities — they are critical risk allocation tools. Whether you are acquiring a business, managing a commercial relationship, or selling to customers, business owners should ensure that agreements are thorough, clear, and enforceable. This will reduce litigation risk and protect your enterprise value. For buyers and operators, reviewing all critical contracts pre- and post-close is an essential part of your diligence and compliance process. Don’t assume the existing agreements are sufficient — many are not. Where possible, standardize contract templates, build clear negotiation guardrails, and involve legal counsel to spot ambiguous or dangerous provisions before they become problems.
May 14, 2025
Business
Unexpected Tax Penalties in Talent Contracts: Could Your Motion Picture, Recording, or Sports Contract be Subject to IRC Section 409A?
Could your motion picture agreement, recording agreement, or sports contract be a non-qualified deferred compensation arrangement? You may think it unlikely, but a non-qualified deferred compensation arrangement refers to any agreement under which an employee or independent contractor—i.e., a “service provider”—may receive a payment in a taxable year later than the year in which the service provider had a legal right to the payment. There are specific rules governing non-qualified deferred compensation arrangements: Code Section 409A of the Internal Revenue Code of 1986, as amended. Failure to comply with the detailed requirements of Code Section 409A can trigger the immediate taxation of deferred income and impose an additional 20% penalty tax on that income. Any contract providing for the provision of services that provides that some payments may be made after the year that the contract was entered into may be a non-qualified deferred compensation arrangement. This is because the Internal Revenue Service takes the position that a service provider first has a legal right to payment when the contract is entered into, and this applies even if the contract requires the service provider to provide services and the services have not yet been provided. Entertainment Industry Examples: How Code Section 409A May Apply Motion picture contracts frequently provide top talent with a percentage of the box office as compensation for services. In recording contracts, a new artist is generally given an advance to deliver a master recording to a record company. The record company owns the master recording, but the agreement provides the artist receives a “royalty” equal to a certain percentage of sales that will be offset against the advance that the artist received. Since the artist does not have a property right in the master recording, the “royalties” are compensation and will be subject to Code Section 409A, unless an exception applies. Sports contracts often provide for deferred compensation in a colloquial sense. Since the payment to be received by the athlete is not a payment under a qualified retirement plan governed by ERISA, the deferred compensation will be subject to Code Section 409A unless an exception applies. One exception to Code Section 409A is the short-term deferral exception. A payment qualifies as a short-term deferral if the payment must be made by March 15 (for a calendar year service recipient) of the year following the year in which the payment becomes vested or is no longer “subject to a substantial risk of forfeiture.” In this case, this is a short-term deferral and Code Section 409A does not apply. Permissible Payment Events Under Code Section 409A If a payment constitutes non-qualified deferred compensation, then there are only certain events on which the payment can be made: An objectively determinable time or schedule set forth in the agreement (e.g., on January 1 of a certain year or the athlete’s 50th birthday) Death or disability Separation from service (with a very specific definition) Change of control (also a very special definition) Unforeseen emergency Once the payment terms are set forth in an agreement, the terms cannot change, except in very limited circumstances. The payment can never be accelerated by more than 30 days, and there are very strict rules regarding further deferral of the payment. One of those rules is that if a payment is deferred, it must be deferred by more than 5 years from the original payment date. Consequences of Violating Section 409A If Code Section 409A applies and is violated, the penalties are generally imposed on the service provider. These penalties include acceleration of recognition of income for all payments to be made under the agreement in the year in which the violation occurs. Additionally, the service provider is required to pay a 20% penalty tax, as well as ordinary income tax on these accelerated payments. Code Section 409A is complex and often overlooked in entertainment and sports agreements. But if your contract includes future payments tied to services performed now, it is worth asking whether these rules apply. Careful planning can help avoid unexpected taxes and penalties.
May 5, 2025
Business
How Buy-Sell Agreements Can Help Prevent a Messy Business Divorce
Just like any kind of relationship, not all business partnerships are built to stand the test of time. They can sour just as easily as a romantic partnership or friendship as vision and long-term goals diverge, financial stress comes into play, or personal issues enter the business relationship. When these kinds of factors arise, it can often result in a “business divorce.” A business divorce has the potential to be just as messy, emotionally charged, and costly as a marital divorce, particularly when there is no established plan in place to outline how the two parties will separate. This is why buy-sell agreements can be critical, helping to ensure a smooth and fair process in the case of a business divorce. It is always best to agree on buyout terms in advance while everyone is getting along and not leave it to the expense and risk of legal proceedings before an arbitrator or judge who does not understand your business. What is a Business Divorce? A business divorce occurs when two or more parties decide to end a business partnership, and it is estimated that anywhere from 50-70% of business partnerships will fail. There can be numerous contributing factors that lead to the dissolution of the partnership. As stated earlier, there are typically differing visions for the company’s future, the strategies used to achieve long-term goals, financial disagreements, or even personal issues that begin to impact the partnership. However, there can also be actions taken by a partner that reflect negatively on the company or even an illness or death that would require the partnership to dissolve. No matter the root cause of the divorce, there are several avenues that can be taken when the partners make the decision to split. This could be one partner buying out the other, fully dissolving the business, or some kind of restructuring that occurs. It is at this stage of deciding which path to take where emotions can start to come into play, and lawsuits and other disputes can arise if there is not an agreed-upon method to end the partnership. This is where buy-sell agreements can be a game changer. Why Buy-Sell Agreements are Critical Think of a buy-sell agreement as a prenuptial agreement for business owners. When a married couple has a prenup in place, it provides a roadmap for how to divide the assets if they divorce. Buy-sell agreements provide the same kind of roadmap for a partnership, outlining a course of action should one partner want or need to leave. As with a prenup, these are typically negotiated when the partnership is established; however, it is never too late to negotiate this in a partnership if one does not already exist. These agreements allow for a smoother process and minimize conflict, as they provide an established business valuation methodology as well as liquidity and exit plans, including the terms of the payout to the departing partner, which could be over several years so as not to impair the business cash flow. They can also prevent a spouse or heirs from attempting to assume a partnership role in the case of a partner’s death or disabling illness, and they can help stabilize the business during what can be a chaotic time. When considering structures for a buy-sell agreement, there are several options. These can include one or more owners buying out a departing owner’s stake, the actual business buying the departing partner’s stake, or some of combination of the two. In the case of death, the buy-sell can provide for the purchase of life insurance on the deceased partner. The structure of a buy-sell agreement is specific to the individual business and partnership and must be agreed upon by all parties involved. At the end of the day, a buy-sell agreement can save a great deal of heartache and expense if you find yourself in the middle of a business divorce. A little bit of additional planning on the front end could be the key to an amicable split that allows for the continuity of the business and avoids a legal mess.
April 18, 2025
Business
Succession Planning for Business Owners: Preparing for the Expected—and the Unexpected
Acquiring a business is an exciting and rewarding achievement, but it’s only the beginning of the journey. Many new business owners focus on growth, operations, and profitability, but one critical factor often gets overlooked: succession planning. What happens if you’re suddenly unable to lead? Have you prepared your business to survive and thrive beyond your direct involvement? According to industry insights, over two-thirds of small business owners plan to retire within the next decade, yet nearly two-thirds of family-owned businesses lack a documented succession plan. Without a solid contingency strategy, a business can face severe disruptions, loss of value, or even risk closure. Succession planning is not just about retirement—it’s about ensuring the business can withstand unexpected challenges, leadership transitions, and shifts in ownership dynamics. It must also take into account your financial legacy, meaning your estate plan is a critical piece of this process. Two Critical Aspects of Succession Planning Succession planning can be broken down into two key areas: management succession and ownership succession through estate planning. While management succession ensures the business continues to operate efficiently after leadership changes, ownership succession focuses on transitioning equity and control in a way that preserves family wealth and business continuity. Succession Planning for Management Purposes For search fund entrepreneurs and independent sponsors, acquiring a business often means stepping into an operation that has relied heavily on the prior owner’s relationships and institutional knowledge. If a crisis arises—whether due to illness, a sudden exit, or unforeseen personal events—having a structured plan ensures the company’s continuity and stability. A business should be able to function independently of its owner to maintain investment value, operational efficiency, and strategic direction. Investors such as family offices and other patient capital providers are increasingly focused on long-term business sustainability. They recognize that a company’s ability to transition leadership smoothly directly impacts its valuation, resilience, and growth potential. Businesses with strong management succession plans are inherently more attractive to investors, lenders, and strategic partners. Key Steps in Management Succession Planning Identifying Future Leadership – Develop a leadership pipeline and invest in training potential successors. Creating Governance Frameworks – Establish clear decision-making protocols, performance benchmarks, and board roles. Documenting Operational Processes – Maintain SOPs, financial reporting procedures, and relationship management protocols. Legal & Financial Structuring – Draft contingency plans, transition agreements, and updated leadership contracts. Employee & Stakeholder Communication – Foster transparency to maintain trust and engagement during transitions. Disney - A Succession Planning Failure: A well-known cautionary tale is Disney’s prolonged succession struggle. It offers a public case study in the risks of delayed or unclear leadership planning. Harvard Law’s analysis explores how missteps in succession planning can result in strategic confusion and shareholder concern. Succession Planning for Ownership & Estate Purposes While leadership succession supports operational continuity, ownership succession via estate planning ensures that equity transfers are executed in a tax-efficient, structured, and family-aligned way. Many business owners delay these conversations until it's too late, leading to conflict and financial inefficiencies. A recent article from J.P. Morgan Private Bank highlights the value of family meetings as tools for creating transparency, aligning generational goals, and easing the emotional weight of wealth transfer decisions. Clear communication and proactive planning are essential to avoiding misunderstandings and ensuring continuity. Key Considerations for Ownership & Estate Succession Planning Recapitalization & Equity Transfers – Gradually shift ownership to heirs, employees, or outside investors. Trust & Estate Structures – Use trusts, GRATs, or similar tools to reduce tax burden and streamline asset transition. Buy-Sell Agreements – Protect against disruption in the event of death, incapacity, or ownership disputes. Liquidity Planning – Ensure cash availability to meet estate taxes and avoid forced asset sales. Open Family Conversations – Define expectations, roles, and stewardship principles across generations. Estate Planning Beyond Business Ownership Estate planning must extend beyond business assets. All holdings—real estate, private equity, marketable securities, and personal property—should be included. A comprehensive plan reduces the risk of asset disputes, tax inefficiencies, and missed philanthropic goals. Key Components of a Comprehensive Estate Plan Multi-Generational Wealth Strategy – Articulate long-term objectives for family stewardship and legacy. Liquidity for Tax Obligations – Prepare for estate taxes without disturbing business operations. Asset Protection – Use legal mechanisms to guard against litigation and liability. Charitable Planning – Incorporate giving strategies that reflect family values and optimize tax outcomes. Building Your Estate Planning Team: Successful estate planning requires the coordinated efforts of legal, tax, and financial professionals. Business owners often work with corporate, tax, and estate attorneys. In addition to legal, family offices are increasingly emerging as a central resource for coordinating these efforts across generations. For example, Cresset Capital offers a holistic family office model that integrates investment, planning, and advisory services. The Role of Recapitalization in Succession Planning Recapitalization is a versatile strategy that supports both management transitions and estate planning. It allows business owners to restructure equity, generate liquidity, and introduce new ownership stakeholders while maintaining stability. Preserve Business Value – Transition ownership strategically to avoid disruption. Generate Liquidity – Create financial flexibility without an outright sale. Support Long-Term Sustainability – Bring in aligned investors who support the next generation of leadership. Final Thoughts: Don’t Leave the Future to Chance Whether you’re planning an exit, acquiring your first business, or simply organizing your affairs, succession planning is not optional. It’s a fundamental aspect of preserving the value you’ve built and ensuring your enterprise—and legacy—endures. A business without a succession plan is a business with an expiration date. Start now. Incorporate recapitalization, leadership development, and comprehensive estate planning into your long-term strategy.
March 21, 2025
Business
Financing in the Independent Sponsor and Search Fund World: SBA vs. Conventional Lending
Financing is one of the most critical components of a successful search fund or independent sponsor acquisition, influencing not just deal structure and capital requirements but also long-term financial health and growth potential. Entrepreneurs and investors evaluating a business purchase must carefully weigh two primary financing options: Small Business Administration (SBA) loans and conventional bank loans. While both have their merits, the choice between SBA and conventional lending impacts everything from cash flow management and debt servicing to operational flexibility and future capital raises. Selecting the right option requires a clear understanding of short-term liquidity needs, financial reporting obligations, investor expectations, and the intended growth trajectory of the acquired company. SBA Loans: Flexible but Costly in Equity Terms The SBA 7(a) loan program is a widely used financing tool, particularly for first-time entrepreneurs and acquisitions of lower middle-market businesses. The program is designed to make small business ownership more accessible by offering low down payments, extended repayment terms, and fewer financial covenants compared to conventional loans. Key Advantages of SBA Loans: Lower Equity Requirements – SBA loans typically require only 10% equity, making them an attractive option for buyers with limited personal capital. In contrast, conventional loans often require 20-50% equity, significantly raising the cash burden. Longer Repayment Terms – The standard 10-year amortization schedule allows borrowers to maintain lower monthly payments, easing cash flow constraints. Limited Financial Covenants – Unlike conventional lenders, SBA-backed loans do not impose strict financial performance benchmarks, providing greater flexibility in early-stage business operations. Easier Qualification Process – Many first-time buyers may find it easier to secure an SBA loan compared to conventional financing due to the government-backed guarantee, reducing lender risk. Challenges of SBA Loans Despite their accessibility, SBA loans come with notable downsides, particularly for search funders and independent sponsors looking for long-term capital efficiency and equity retention: Personal Guarantee Requirements – SBA loans require personal liability from the borrower, meaning that if the business fails, personal assets may be at risk. Restrictions on Seller Notes & Subordinated Debt – The SBA often limits the use of seller financing and additional subordinate debt, making capital structuring more rigid. Prepayment Penalties & Financing Limitations – Borrowers looking to refinance into more favorable debt structures down the road may face prepayment penalties, increasing overall financing costs. Growth Limitations – The lack of institutional-style covenants can prevent businesses from building the structured financial discipline needed for future capital raises or attracting private equity investment. For sponsors and search fund entrepreneurs planning recapitalization, secondary financing rounds, or eventual exit strategies, the limitations associated with SBA loans should be carefully considered. Conventional Bank Lending: More Rigid, but (Maybe) a Stronger Long-Term Fit For experienced operators or businesses with strong existing cash flow, conventional loans can be a more sustainable long-term financing solution. These loans provide greater flexibility in structuring deals, but they also come with stricter requirements. Key Advantages of Conventional Loans: Higher Loan Amounts – Unlike SBA loans, which cap at $5 million, conventional banks can finance larger acquisitions, making them more suitable for companies with $5M+ in EBITDA. Stronger Banking Relationships – Working with a commercial bank can create opportunities for long-term financial partnerships, including credit facilities, treasury services, and strategic capital allocation. More Favorable Equity Retention Terms – Conventional lenders often allow higher levels of seller financing and preferred equity arrangements, giving the buyer greater control over the capital stack. Stricter Covenants: More Financial Controls and Reporting Unlike SBA loans, conventional financing requires detailed financial oversight, which, while adding complexity, can ultimately benefit long-term financial planning and investor confidence: Debt Service Coverage Ratios (DSCR) – Lenders typically mandate a minimum DSCR threshold, ensuring the business maintains healthy cash flow relative to debt obligations. Regular Financial Reporting – Borrowers must provide quarterly and annual financial statements, reinforcing financial discipline and operational transparency. Leverage & Liquidity Limits – Many conventional loans include leverage constraints, preventing businesses from taking on excessive debt that could jeopardize financial stability. While these restrictions may seem burdensome, they prepare companies for future institutional investment and create stronger exit opportunities by making businesses more attractive to private equity firms and strategic acquirers. Choosing the Right Financing for Sponsors and Search Funds The decision between SBA and conventional financing depends largely on the business model, investor profile, and long-term capital strategy of the acquirer. SBA Loans Are Best For: First-time search funders acquiring sub-$5 million EBITDA businesses Deals where seller financing is limited or unavailable Entrepreneurs seeking maximum leverage with minimal equity investment Buyers prioritizing cash flow flexibility over institutional financing constraints Conventional Loans Are Best For: Larger acquisitions requiring more flexible financing structures Search funders looking to build long-term banking relationships Companies planning to secure future private capital or institutional investment Acquisitions where financial discipline and structured reporting will be critical for growth and scalability Final Thoughts: Aligning Capital with Growth Strategy For independent sponsors and search fund entrepreneurs, financing is about more than just getting the deal done—it’s about positioning the business for long-term success. SBA loans can provide immediate access to capital, but conventional financing ensures long-term scalability and financial discipline. Navigating the complexities of acquisition financing requires strategic planning and expert guidance. Working with an experienced attorney and financial advisor can help independent sponsors and search funders structure deals properly, negotiate loan agreements, and ensure compliance with lender requirements, ultimately protecting long-term equity value.
February 28, 2025
Business
Congress Extends Telehealth Waivers
On December 20, 2024, as part of its stopgap government funding legislation (the “Continuing Resolution”), Congress issued an important extension of telehealth waivers and flexibilities currently in place for the next two years through December 31, 2026. The Continuing Resolution also includes the following measures relevant to the telehealth market segment: Patients’ homes will continue to serve as eligible Originating Sites for all telehealth services. All Medicare-enrolled providers will continue to be eligible providers for the purpose of providing telehealth services. There will continue to be no geographic limitations on where the patient or the eligible provider is physically located within the United States during a telehealth service. Rural Health Clinics (RHCs) and Federally Qualified Health Centers (FQHCs) will continue to serve as eligible Distant Sites for non-behavioral health telehealth services. Providers may continue to use audio-only technology to provide reimbursable telehealth services. Hospice providers may continue to use audio-visual telehealth technologies to conduct face-to-face encounters to recertify hospice care eligibility. Additionally, the Continuing Resolution further delays the requirement that Medicare beneficiaries have an in-person visit with their behavioral health provider within six months of their initial telehealth appointment. This CR is indicative of the continued evolution of telehealth services, the trajectory of which accelerated dramatically during the COVID-19 Public Health Emergency. It has become clear that legislators believe telehealth services to be an integral aspect of the U.S. healthcare delivery system. The challenge in the future will be figuring out which industry segments (i.e., behavioral health, rural health access, remote monitoring) will benefit the most from making these rules permanent.
February 20, 2025
Business
Search Funds Are Changing the Small Business M&A Landscape
In recent years, search funds have seen increased usage in small business acquisitions, offering a structured yet flexible approach to acquiring and growing companies. The "origin story" is often credited as arising out of Stanford Business School in the 1980s, and has gained traction among entrepreneurs, investors, and family offices since then. It provides a new path to ownership and long-term value creation. So, why are search funds transforming the small business M&A landscape? The answer starts first with the structure of these search funds, how they differ from traditional private equity, and the legal and financial considerations investors and entrepreneurs need to understand. They share many similarities with independent sponsor deals but also have a number of stark differences. What Is a Search Fund? A search fund is a structured investment vehicle designed to help an entrepreneur find, acquire, and operate a small business. It typically follows a two-stage process: Search Phase Investors provide initial capital to support a qualified entrepreneur as they search for a business to acquire. The timeline for this search can typically take 12–24 months and is often dictated by the terms of the investment documents. This initial capital is used to cover due diligence expenses, professional fees, and provide some form of compensation to the searcher (although this last point can turn off some investors). Searchers typically target businesses that fit a particular investment thesis, such as those with strong recurring revenue, low customer concentration, and proven stability. The process requires extensive outreach, negotiation, and due diligence, making it both intensive and time-consuming. Acquisition & Operation Phase Once a suitable business is identified during the search phase, the entrepreneur leads the acquisition, often bringing in additional investor capital and financing for the purchase. SBA loans are often utilized as a financing option unless it is an asset-heavy target, in which case a traditional lender may be willing to finance the deal. Post-acquisition, the entrepreneur operates and scales the business, creating value for investors over a 5- to 10-year horizon. This differs from independent sponsor deals where the independent sponsor may prefer a "hands-off" approach rather than taking on the "operating partner" role. The target size for these acquisitions is typically small businesses with $1M–$5M in EBITDA, focusing on stable, profitable companies where an operational leader can add significant value. Some might be willing to acquire a business with less stable footing if there are clear deficiencies that can be quickly remedied. An example of these remedies can include digital transformation, improved sales or operational processes, faster accounts receivable cycles, or vendor/supplier issues that can be addressed with fresh capital. Why Are Search Funds Growing in Popularity? Aging Business Owners & Succession Gaps Many Baby Boomer-owned businesses are coming up for sale, but they lack internal succession plans. We've all heard about the upcoming "transfer of wealth." This is largely what is being discussed. There are huge amounts of capital locked up in small business ownership. Search funds provide a structured solution, offering business owners an exit while ensuring continuity under capable leadership. Alternative to Private Equity & Traditional M&A Private equity (PE) firms often seek larger, high-growth businesses or require substantial restructuring post-acquisition. Search funds focus on stable, cash-flow-positive businesses, often without excessive debt financing. These search funds also offer emerging managers a platform to showcase their skills and set up future (larger) deals. Strong Investor Interest in Small Business Buyouts Many family offices, high-net-worth individuals, and independent investors are attracted to the long-term, hands-on nature of search fund investments, and the chance to mentor emerging entrepreneurs. Unlike traditional PE, investors partner directly with an operator, aligning interests toward sustainable growth rather than quick flips. Proven Success & Institutional Recognition Studies show that successful search funds yield attractive returns. Stanford’s research indicates an average IRR of 30–35% for successful search fund investments. Business schools and institutional investors are increasingly supporting search funds as a legitimate investment class, with many schools creating "entrepreneurship through acquisition" workshops or curriculums. Key Legal & Financial Considerations While search funds present compelling opportunities, structuring the deal properly is critical to long-term success. Here are key legal and financial considerations investors and entrepreneurs should keep in mind: Legal Considerations: Fund Formation & Investor Agreements: Search fund structures vary—some use traditional LP/GP models, while others form LLCs with pro-rata investor rights. Well-drafted legal agreements define profit splits, investor rights, and operational control. Due Diligence & M&A Structuring: Business acquisitions involve legal, tax, and regulatory complexities. Asset vs. stock purchases have different tax implications and liability considerations. Governance & Founder-Investor Alignment: Search funds operate with investor oversight, often with board seats or advisory committees. Proper corporate governance structures protect both investors and the entrepreneur. Financial Considerations: Equity vs. Debt Financing: Search funds typically rely on equity-heavy funding rather than high levels of debt. However, some deals incorporate SBA 7(a) loans or seller financing to optimize capital efficiency. Profitability & Valuation Metrics: Investors focus on stable EBITDA margins, typically in the 15–25% range. Many search-acquired companies operate in low-tech, recession-resistant industries (e.g., B2B services, healthcare, niche manufacturing). Exit Strategies: Search fund exits typically occur via private equity acquisition, strategic buyer sale, or investor buyout. Holding periods range from 5–10 years, aligning with long-term wealth creation. Should You Invest in or Launch a Search Fund? For investors, search funds offer a compelling alternative to traditional private equity, allowing for: Higher potential returns in undercapitalized small business sectors. More direct involvement and operational influence in acquired businesses. Alignment with long-term value creation, rather than short-term financial engineering. For entrepreneurs, search funds provide: A structured pathway to business ownership with investor-backed support. Access to capital and advisory networks without needing personal funds upfront. A leadership role with strong financial upside. Final Thoughts: The Search Fund Model Is Likely to Continue Trending Upwards As small business ownership transitions accelerate, search funds will continue to play a growing role in the M&A ecosystem. For investors, they provide an opportunity to back talented entrepreneurs in acquiring and scaling high-quality businesses. For "searchers" or buyers, search funds offer a viable and structured alternative to a startup.
February 19, 2025
Business
Startup Success Starts with Governance Documents and Clear Ownership Rules
If you are launching a new business without proper governance documents, you’re risking financial loss and business owner disputes. Every business owner needs properly drafted governance documents. This cannot be overstated. It’s exciting to launch a new business, but failing to properly document the business relationship between owners is a major pitfall. It is not uncommon for attorneys to have witnessed this firsthand, numerous times, and it almost always results in financial loss or dispute. An episode on Acquiring Minds podcast provides a powerful example of the troubles you can face without these governance documents (jump to the 51-minute mark to hear why). Learn how to safeguard your venture from the outset. Assuming a business is structured as an LLC, an operating agreement sets the governance foundation and prevents many avoidable disputes. Key Provisions to Consider Equity Vesting Schedule: For startups and emerging companies, it’s critical to protect the company from premature departures. Implementing a vesting schedule keeps everyone incentivized for the long haul, ensuring commitment and stability. Dispute Resolution: Conflict is inevitable. Whether it’s a disagreement over strategy or management style, a clear dispute resolution mechanism (such as mediation or arbitration) can help resolve disputes without causing a full breakdown of the business. In the Acquiring Minds podcast example, a "shotgun clause" would have been helpful. This is a buyout mechanism that also doubles as a form of dispute resolution. These tools work together to protect the business during critical decision-making moments. Equity Buyout Terms: Define how ownership interests can be bought or sold to ensure fairness while protecting the business from being forced into unwelcome arrangements. Important terms include shotgun clauses, puts, and call options. Decision-Making Processes: Specify how major business decisions will be made. This includes setting voting thresholds and identifying areas that require unanimous consent. It’s also important to establish early on whether someone will hold a majority stake in the company. Even a 1–2% difference in ownership can make a significant impact. Exit Strategies: Plan for the future by outlining provisions for dissolution, sale, or succession. For instance, drag-along rights protect majority shareholders in a sale, while tag-along rights safeguard minority interests. These provisions ensure smooth transitions and clarity for all parties. Don’t Rely on A Handshake A handshake may start a partnership, but only a well-drafted operating agreement can protect it. Having robust governance documents isn’t just a best-practice, it’s essential for protecting your venture and ensuring long-term success. Don’t overlook the importance of partnering with experienced legal professionals to get it right.
January 29, 2025
Business
Why Are the Fees to Sell a Business So High? It’s a Matter of Expectations
“How much will it cost to sell my business?” It seems like a reasonable enough question—and a business owner is wise to plan ahead and think about the financial impact of merger, acquisition, or other business transactions early on. However, focusing on what you’ll pay to sell a business is a classic example of “missing the forest for the trees.” Or, to put it another way, missing the sale for the fees. I get it. Legal costs are never pretty. Most business owners are fortunate enough to only pay attorney’s fees periodically, on an as-needed basis, for relatively small projects. We’re talking about document review, collections, intellectual property development, and so forth. If you’re really unlucky, you may need to bring on a lawyer for litigation. The associated bills aren’t pleasant, but they won’t bankrupt you (and if they do, you hired the wrong attorney). When you have the opportunity to consummate the sale of your company, on the other hand, you can expect to receive the largest legal bill of your lifetime. Depending on the size of the deal, your attorney may charge you upwards of six figures. In any other situation, the price would seem exorbitant—outrageously so. But a business transaction isn’t like other situations. It’s an extraordinary event with exponentially higher stakes than an owner is used to. No business milestone compares. Yes, you’ll receive the largest legal bill of your lifetime—because you’re earning the biggest payday of your lifetime. It’s a matter of scale and complexity. You will not get a good second “bite of the apple.” For sellers, some level of legal “sticker shock” is understandable. Few people on Earth can normalize earning several million dollars, or several hundred million, at once. The problem arises when a business owner handcuffs their advisors due to fee constraints. The handcuffs could have unintended implications for a seller. I recently represented a client who had grown accustomed to relying on legal assistance from a family friend. He was used to essentially paying his lawyer a couple of bucks and a case of beer. When it came time to sell his business, the client realized he needed a different caliber of attorney—but failed to adjust his expectations accordingly. When he learned he owed approximately $300,000 in legal fees, I watched the color drain from his face. Keep in mind my client’s business sold for $75 million. Our fees amounted to less than 1% of the total sale price. That’s in line with (admittedly loose) industry standards—if not below. My client knew how many hours were invested in the matter—and he had the budget in mind before the deal commenced. He knew a substantial bill was coming. But it wasn’t tangible for him until the end. The moral of the story? Don’t wait until after you’ve sold your business to think about the costs of selling your business. Develop a financial plan—and speak to your advisors to understand the moving parts and inputs to a transaction. Be prepared to spend substantial fees paying your attorney, investment banker, accountant, M&A advisor(s), and any other professionals involved in your team. After all, the sale of your business likely will be the largest financial transaction of your lifetime. Then, move all that to the back of your mind and prepare yourself for the biggest question ahead: what you’ll do with all that money after you close?
October 17, 2024
Business
What M&A Buyers Lose by Keeping Their Closing Checklists to Themselves
I recently represented a group of business owners in the sale of their company. As with any merger or acquisition, the transaction demanded tremendous patience, effort, and commitment from all people involved. For my clients, however, the deal was far more onerous than it needed to be — because the buyer’s attorney chose not to work from a closing checklist. A closing checklist can be thought of as a shared roadmap for an M&A transaction. It lays out all the steps that must be taken to bring the deal to fruition, specifying the roles and responsibilities of the buyer, the seller, and any other participants. Checklists cover everything from sophisticated legal and financial considerations (e.g. intellectual property searches, lien releases, third-party consents) to minute particulars such as signatures and wiring instructions. Whatever its level of detail, any checklist is better than none. Deals without closing checklists sometimes waffle as parties experience distrust, restlessness, and confusion over priorities. While this transaction fortunately did go through, my clients faced significant friction and frustration. At times, a collapse appeared likely. Instead of providing a closing checklist, the buyer essentially assigned us several dozen to-dos, which was just a rundown of tasks we needed to complete in order to satisfy their pre-closing requirements. It was a one-sided, opaque way of doing business. It left us feeling as though we were operating in a vacuum and never working fast enough. This kind of approach not only strains the lines of communication between a buyer and seller, but also tends to dissolve any kind of meaningful negotiations. When you’re rushing through line items without the larger context of the deal in mind, you give up your leverage. A closing checklist is essential because it situates parties within the same universe and keeps their attention oriented on a shared goal. It’s a common point of reference for discussions and perspective — a constant reminder that all that labor and stress is in service of a mutually beneficial transaction. If you don’t have a closing checklist, you become blind to the other side’s objectives as well as your own. What is particularly baffling about the decision to keep the seller in the dark is that it creates more work for the buyer. Closing checklists are generated in almost every transaction. They flow naturally from the buyer’s documentation and due diligence. There’s no additional effort or risk to making them generally available to the other party. By refusing to share their checklist, the buyer chooses instead to dole out the information in a piecemeal manner, potentially causing errors and slowing down the deal. It’s the difference between telling a seller what you aim to accomplish and telling them what to do. It’s turning what should be a partnership into a managerial relationship. And ultimately, it’s unproductive. Few owners can put up with being bossed around—especially when they’re in the middle of exiting their business. Originally posted 09/26/2019 - no content changes.
October 3, 2024
Business
Not Sure if Your Company Is Ready to Sell? Consider the PAEI Model
For most business owners, the chance to sell your enterprise is a once-in-a-lifetime opportunity. But if you take that offer too early or at the wrong stage of business development, the sale could result in a number of undesired outcomes: a low valuation, difficulty finding a buyer, management disputes, contract issues, and other legal problems. Selling a business is like preparing a meal. It’s crucial for a business owner to be able to recognize if their business is either under or overcooked before taking it to market. Unfortunately, it’s not as simple as using a meat thermometer. Instead, owners rely on systems such as the PAEI Model, which Dr. Ichak Adizes developed in the 1970s to track business growth and stability. To this day, business owners use the model to understand their organizations’ lifecycles through the lens of management dynamics. How the PAEI Model Works “PAEI” stands for four different yet common management personae that affect a business’s short-term and long-term performance. Producers are managers who are task-oriented and focused on tangible results. They demonstrate big-picture thinking with little regard to interpersonal or individual concerns. Administrators are managers driven by procedure and planning, with a strong focus on routine and structure in order to maintain success. Entrepreneurs are managers driven by dreams and future achievement. They’re concerned less with day-to-day operations and more with a broad, long-lasting vision of the business. Integrators are managers who work well with others. These individuals are adept at both considering and balancing the concerns of other managers and employees. Each of these roles is important to business development, but each has its own time. The PAEI model lays out an arc of business growth, starting with “Courtship” (when an owner “flirts” with the business idea), which leads to “Infancy,” “Go-Go,” “Adolescence,” “Prime,” and ultimately stability. Which Stage Is the Ideal Moment to Sell? Every stage can spin off into a negative conclusion. For instance, Infancy can result in “Infant Mortality” when there’s nothing left but a Producer. Adolescence, meanwhile, can result in “Divorce” (the owner and the company split), which may lead to “Premature Aging” (the company peaks early without an entrepreneurial vision) and an “Unfulfilled Entrepreneur.” To avoid the potential pitfalls during every stage of a business’ lifecycle, each one of the four management styles must be present. But not everyone comes to the foreground in every stage. Instead, a single management style or combination of styles takes dominance at certain points along the way. For example, in Courtship, the very beginning stages of a new business, the Entrepreneurial management style is required for crafting the initial big ideas and long-term goals that will sway investors and fund the enterprise into Infancy. Once the money rolls in and the business reaches Infancy, it’s important for a Producer to recognize how to responsibly use the startup funds to survive on a daily basis. After some inevitable growing pains, a business reaches Adolescence with the help of an Administrator, whose management style shifts the focus away from sales and revenue generation—and toward cost-cutting, boosting profits, and keeping the company lean. At this stage, an organizational structure is key in order to reach the Prime period of a lifecycle. When the business is in its Prime—when profits are up, operations are running smoothly, and customer satisfaction is at an all-time high—that’s when it’s time to sell. Yes, believe it or not, the best time to sell your business is usually right before it reaches the Stable stage. While further growth can seem all but guaranteed at the Prime stage, according to the PAEI model, most companies begin to falter and precipitously lose value once they’ve become Stable. This is the period in which the Entrepreneurial management style begins to fade, and the Administrative and Integrator styles achieve dominance. In other words, the initial visionary is replaced by people who excel at bureaucracy and longevity. In the realm of mergers and acquisitions, the Integrator is frequently the buyer. As a seller, it’s up to you to ensure the business has reached its Prime and that all the elements are in place for continued success—and to get out right before the business peaks and starts to lose value. While the PAEI Model is not a guaranteed method of success, I believe it can provide rare insight into the business lifecycle. It presents a valuable framework for the roles and traits it takes to reach success and ultimately earn the highest possible sale price for your company.
September 19, 2024
Business
Letters of Intent (LOI) – Buyer’s Exclusivity
I’ve reviewed many LOIs over the years – some we’ve prepared and others the client prepared. I’ve found that too many people view LOIs as form documents containing commercial terms. Yes, LOIs are vital documents establishing the commercial terms of a transaction. However, LOIs should not be considered “throwaway” forms in the M&A process. I think the lax attitudes relate to the non-binding nature of most terms in the LOI. Yet, there should be specific binding terms in every LOI. For a buyer, one important binding term is the exclusivity provision. Most recently, I needed to enforce this provision due to a seller’s breach. My client invested much of their time and money evaluating a transaction and documenting the same (legal, accounting, and banker time). The exclusivity provision protects a buyer from a seller “two-timing” them by not committing fully to the contemplated transaction and not negotiating in good faith. In my instance, the seller committed to another transaction during my client’s exclusivity period, leaving my client with much frustration and wasted costs. Buyers rightly demand a fair time frame to evaluate and work with a seller to consummate a transaction. Buyers invest substantial front-end costs in this regard. Fairtrade is for the seller to commit to an exclusivity period (30, 60, 90 days) to allow the parties to finalize a transaction in good faith. My client had an exclusivity period with “teeth” that allowed him to recoup these costs – and the seller did reimburse. But buyers beware. Without an adequate exclusivity provision, among other protective provisions, much time and money can be lost when a seller changes course.
September 12, 2024
