Main Street Deals

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...