Main Street Deals

Sam Rosati and David Brackett explore the business of building SMB Law Group, a firm designed specifically for acquisition entrepreneurs. Brackett, the firm's COO, joined roughly six months after launch when the three founding attorneys needed help scaling beyond a glorified solo practice. Today, the firm employs 28 people and has earned recognition from Financial Times and law.com for innovation...

Sam Rosati and Kevin Henderson explore the legal work stream in small business acquisitions and how buyers can reduce deal risk from letter of intent through closing. The conversation addresses why so many deals fall apart after LOI despite strong financials, focusing on the specific legal provisions and negotiation tactics that either protect or jeopardize a transaction. Henderson emphasizes that...

Sam Rosati and Eric Pacifici examine the critical period between signing a letter of intent and closing a small business acquisition on Main Street Deals. Drawing from their firm's 387 closed transactions, they reveal that roughly 68% of deals under LOI actually reach closing — a reality that contradicts the false confidence many first-time buyers feel after signing. They discuss: - Why quality of...

Sam Rosati and Eric Pacifici break down the 2025 SRS Acquiom Lower Middle Market Research Report, examining transaction terms for deals under $50 million. The conversation focuses on how purchase agreement structures and legal terms affect risk allocation between buyers and sellers. Eric and Sam explain why understanding indemnification caps, escrows, and earn-outs matters just as much as negotiat...

Eric Pacifici and Kevin Henderson examine restrictive covenants in small business acquisitions on Main Street Deals. The discussion clarifies how business sale non-competes differ from employment agreements and why they remain enforceable even in restrictive jurisdictions like California. Kevin and Eric explain the legal frameworks governing covenant scope and duration, including state-specific ru...

Sam Rosati and Kevin Henderson are joined by Kevin's wife Tara Henderson to discuss the realities of buying and operating a business as a married couple. Tara recently stepped into the full-time operator role at Supreme Wraps Dallas, a car wrapping franchise the couple acquired in January 2025. The conversation unpacks the challenges of transitioning from part-time work and raising three children...

Sam Rosati and Kevin Henderson explore common mistakes first-time small business buyers make during the search and acquisition process on this episode of Main Street Deals.  Drawing from their work with 10 to 30 active searchers at any given time, the co-founders of SMB Law Group share tactical lessons about search hygiene, deal team selection, and the timing decisions that can make or break a tra...

Eric Pacifici and Kevin Henderson reflect on four years of building SMB Law Group from scratch, using the anniversary as a lens to examine the realities of entrepreneurship through acquisition, lower middle market M&A, and operating a fast-growing law firm. The conversation blends personal reflection with tactical lessons from nearly 400 closed transactions, including how their views on diligence,...

In this episode of Main Street Deals, Sam Rosati and Kevin Henderson break down the role of Quality of Earnings reports in small business acquisitions and why financial diligence can make or break a deal. They explain how Q of E reports help buyers validate a company’s financial reality, uncover hidden risks, and avoid dramatically overpaying for inflated or inaccurate earnings. The conversation w...

Kevin Henderson and Eric Pacifici break down the realities of legal due diligence in small business acquisitions, clarifying one of the most misunderstood parts of the deal process. Drawing on hundreds of transactions, they explain why diligence is not about finding a reason to walk away, but instead about identifying, understanding, and allocating risk. The conversation walks through how buyers s...

Sam Rosati and Kevin Henderson break down one of the most misunderstood and critical concepts in small business acquisitions: working capital. Prompted by listener requests, they walk through why working capital is often a top deal killer and how misalignment between buyers and sellers can derail otherwise strong transactions. Through clear examples and practical frameworks, they explain how worki...

Sam Rosati and Kevin Henderson break down what it actually takes to win a small business acquisition without being the highest bidder. Drawing from real deal experience and active transaction volume, they walk through the full buyer journey from sourcing deals to navigating LOIs and closing, emphasizing the importance of positioning, communication, and psychology in competitive processes. The conv...

Sam Rosati and Eric Pacifici break down the realities of sell-side M&A in the lower middle market, drawing from their experience advising both buyers and sellers. They share practical insights on when business owners should begin preparing for a sale, why proactive legal organization matters more than most realize, and how the dynamics of today’s market favor well-prepared sellers. The conversatio...

Eric Pacifici and Kevin Henderson walk through the full lifecycle of acquiring a small business, breaking down each stage from sourcing deals to post-close integration. They provide a practical, step-by-step overview tailored to self-funded searchers, independent sponsors, and lower middle market buyers, while highlighting where deals most commonly break down. The conversation emphasizes how compe...

Kevin Henderson is joined by Evan Thomson to break down one of the most overlooked yet critical parts of any acquisition: legal due diligence. Drawing from Evan’s experience as fractional general counsel, they explore how legal diligence differs from financial diligence and why it rarely kills deals but can create serious downstream risk if ignored. The conversation focuses on practical, real-worl...

Kevin Henderson and Sam Rosati break down one of the most overlooked aspects of buying a small business: how to properly plan and structure the full capital stack. Using a practical sources and uses framework, they walk through what actually happens after an LOI is signed and where first-time buyers tend to get caught off guard. The conversation highlights the real costs, financing dynamics, and o...

Sam Rosati and Eric Pacifici break down one of the most important structural decisions in any small business acquisition: whether to buy a company through an asset purchase or a stock purchase. Drawing from real deal experience, they explain how the choice affects liability, taxes, contracts, and the overall risk profile for buyers. The conversation walks through how each structure works in practi...

Eric Pacifici and Kevin Henderson draw on their experience closing hundreds of lower middle market transactions to break down real problems that can surface after buying a business. Rather than focusing on theory, they share anonymized stories from actual deals where issues like seller misconduct, working capital mistakes, and poorly structured transactions created major risks for buyers. The conv...

In this episode of Main Street Deals, Kevin Henderson and Sam Rosati continue their deep dive into letters of intent, picking up where the prior conversation left off. They move beyond headline purchase price terms and into the often overlooked mechanics that can materially change a deal’s outcome. From seller notes and personal guarantees to working capital adjustments and indemnification structu...

Eric Pacifici and Sam Rosati break down one of the most important documents in any small business acquisition: the Letter of Intent. In this episode, they walk line by line through their LOI template and explain why every sentence matters, from structuring purchase price to protecting exclusivity. Drawing on real transaction experience and common deal failures, they highlight the practical decisio...

In this episode of Main Street Deals, Sam Rosati and Kevin Henderson step back from deal breakdowns to share the origin story behind their partnership and the law firm they built to serve the small business acquisition community. Kevin walks through his path from growing up in California to Michigan Law and the highest levels of big law, navigating the 2008 financial crisis, burnout, and ultimatel...

In this episode of Main Street Deals, Kevin Henderson and Sam Rosati break down the most common reasons small business acquisitions fall apart and what buyers can do to spot red flags early. Drawing from real transaction data and firsthand deal experience, they walk through the financial, psychological, and external factors that derail deals long before closing. The conversation offers a candid lo...

In the inaugural episode of Main Street Deals, co-hosts Sam Rosati, Eric Pacifici, and Kevin Henderson lay out why small and medium-sized business acquisitions deserve a more honest, experience-driven conversation. Drawing from hundreds of closed and broken transactions, they explain why M&A at the Main Street level is harder, messier, and more consequential than most people expect. The discussion...

Main Street Deals is a practical podcast for entrepreneurs buying, selling, and operating small businesses. Hosted by experienced M&A attorneys, the show breaks down what actually matters in real-world acquisitions—from LOIs and diligence to closing and the first 90 days of ownership. Each episode combines deal education, war stories, and conversations with buyers, operators, and industry experts...