Main Street Deals

SMB Law Group LLP
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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 to give listeners a clear-eyed view of how small business deals really work. The focus isn’t theory or hype—it’s judgment, structure, and lessons learned inside hundreds of transactions.

Episodes

  1. 2D AGO

    From Big Law to Small Business M&A - Main Street Deals #3

    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 ultimately walking away from the corporate grind. From there, the conversation shifts to how a connection through the emerging ETA community led to the launch of their firm and why they saw a massive gap in legal services for small business buyers. They also unpack what today’s searchers and independent sponsors actually look like, how deals are being financed, and the industries attracting the most activity. Drawing from hundreds of transactions, they share perspective on who is buying businesses, how those deals are structured, and what makes this ecosystem different from traditional private equity. They discuss: Kevin’s journey from big law to entrepreneurship and why he chose to launch his own firm How the ETA community helped spark the creation of a law firm built for small business buyers The typical profile of today’s SMB acquirer, including age range, background, and financing strategies The difference between self-funded searchers and independent sponsors Common industries and deal structures across lower middle market transactions Why operating experience gives a different lens than traditional M&A law Links: SMB Law Group - https://smblaw.group/ Eric on LinkedIn - https://www.linkedin.com/in/eric-b-pacifici/ Kevin on LinkedIn - https://www.linkedin.com/in/khendersonco/ Sam on LinkedIn - https://www.linkedin.com/in/sam-rosati-68787a8/ Topics: (00:00:00) - Intro (00:02:09) - Kev’s origin story (00:06:40) - Lessons from a solo-practice upbringing (00:08:42) - Chasing top-tier deal training (00:14:11) - Burnout, in-house pivot & COVID (00:17:45) - ETA/Twitter DMs to a real firm (00:21:05) - Building a sustainable pipeline (00:25:03) - Why the ETA community needed a specialized SMB M&A law firm (00:28:28) - Buyer demographics (00:33:49) - How buyers finance acquisitions (00:37:59) - Independent sponsors explained (00:44:21) - Deal volume, war stories, and the entrepreneur-lawyer perspective

    50 min

  2. FEB 10

    What Really Kills Small Business Acquisitions - Main Street Deals Episode #2

    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 look at how quality of earnings, seller behavior, financing challenges, and even buyer readiness can determine whether a deal survives. They discuss: • Why financial reality gaps are the leading cause of busted deals • How quality of earnings findings often force renegotiation or termination • The role seller psychology and trust play throughout the deal process • Common financing and SBA-related issues that can unexpectedly kill transactions • How to identify warning signs early and protect yourself in the LOI stage This episode is a practical guide for buyers who want to understand what actually kills deals and how to improve their odds of getting to the closing table. Links: SMB Law Group - https://smblaw.group/ Eric on LinkedIn - https://www.linkedin.com/in/eric-b-pacifici/ Kevin on LinkedIn - https://www.linkedin.com/in/khendersonco/ Sam on LinkedIn - https://www.linkedin.com/in/sam-rosati-68787a8/ Topics: (00:00:00) - Intro(00:02:05) - Understanding deal killers(00:03:26) - The importance of data and LOI(00:05:32) - Breaking down deal killers(00:06:12) - Financial reality gaps(00:09:05) - Seller psychology and trust issues(00:09:24) - External factors and financing(00:11:03) - Recognizing deal signals(00:16:09) - Addressing financial reality in LOI(00:25:14) - Pressure testing assumptions in quality of earnings(00:25:39) - Negotiation strategies for buyers(00:28:13) - The human element in LOI negotiations(00:29:40) - Building trust and addressing psychological factors(00:36:00) - External factors impacting deals(00:40:29) - Legal matters and deal killers(00:46:37) - Personal reflections and final thoughts

    51 min

  3. FEB 3

    #1: What Buyers Get Wrong in Acquisitions - Welcome to Main Street Deals

    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 sets the tone for the show by focusing on real-world deal execution, common failure points, and the responsibility that comes with advising buyers and sellers navigating life-changing transactions. We discuss: Why M&A is filled with hidden pitfalls, and why most buyers underestimate the difficulty The gap between theory and reality in deal execution, diligence, and valuation How seller psychology, financing constraints, and quality of earnings drive deal outcomes The importance of hiring specialized experts instead of trying to DIY critical parts of a transaction What buyers, sellers, and advisors should realistically expect when navigating deals between $1 million and $25 million Links: SMB Law Group - https://smblaw.group/ Eric on LinkedIn - https://www.linkedin.com/in/eric-b-pacifici/ Kevin on LinkedIn - https://www.linkedin.com/in/khendersonco/ Sam on LinkedIn - https://www.linkedin.com/in/sam-rosati-68787a8/ Topics: (00:00:00) - Intro (00:03:53) - Meet the hosts: Eric, Kevin, and Sam (00:05:41) - The importance of experience in M&A (00:09:10) - Balancing legal and business responsibilities (00:18:13) - The role of experts in M&A transactions (00:20:15) - DIY legal pitfalls (00:21:04) - Market overview for 2025 (00:22:55) - Impact of government policies (00:24:10) - Diligence process insights (00:25:30) - Deal structuring strategies (00:27:58) - Busted deals and their causes (00:37:44) - Looking ahead to 2026 (00:39:16) - Final thoughts and resources

    40 min

  4. JAN 26

    Main Street Deals Trailer

    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 to give listeners a clear-eyed view of how small business deals really work. The focus isn’t theory or hype—it’s judgment, structure, and lessons learned inside hundreds of transactions. Main Street Deals is hosted by Eric Pacifici, Kevin Henderson, and Sam Rosati. The three are former Big Law M&A attorneys, active dealmakers, and operators who have sat on both sides of the table. Together, they bring pattern recognition earned from hundreds of transactions and the empathy that only comes from ownership.

    3 min

Trailer

About

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 to give listeners a clear-eyed view of how small business deals really work. The focus isn’t theory or hype—it’s judgment, structure, and lessons learned inside hundreds of transactions.

Information

  • Creator
    SMB Law Group LLP
  • Years Active
    2K
  • Episodes
    4

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