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Main Street Deals

Main Street Deals

Von: 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.
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  • Quality of Earnings and the Hidden Risks in Acquisitions

    Quality of Earnings and the Hidden Risks in Acquisitions
    May 12 2026
    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 walks through the mechanics of revenue testing, working capital analysis, cash proofs, and normalized EBITDA adjustments while also highlighting the limitations of Q of E reports in SMB transactions. Sam and Kevin also share real-world examples of deals where financial diligence uncovered major issues, forced renegotiations, or protected buyers from catastrophic mistakes. We discuss: What a Quality of Earnings report actually is and how it differs from audited financials Why inaccurate seller financials can dramatically inflate purchase price How cash proofs and revenue testing uncover hidden financial issues The most common EBITDA adjustments that lead to deal renegotiations Why small business buyers should rarely skip financial diligence The limitations of Q of E reports and the fraud risks they cannot fully eliminate How working capital analysis impacts deal structure and purchase price Why third-party diligence providers add psychological and negotiation leverage during acquisitions This episode is a practical guide for SMB buyers, investors, and operators who want to understand the real financial risks hiding inside acquisition deals. Links: SMB Law Group - https://smblaw.group/ Evan on LinkedIn - https://www.linkedin.com/in/evan-thomson-327a78216/ 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(00:01:11) - What is a QOE?(00:04:45) - Assurance vs audit(00:07:20) - Inside the workbook(00:09:25) - Restating the P&L(00:13:39) - Balance sheet working capital(00:15:05) - Cash proof testing(00:19:07) - Limitations and QOE lite(00:23:38) - Fraud risks and lender requirements(00:25:52) - Renegotiating after findings(00:37:28) - Who can skip QOE(00:40:30) - When QOE is better(00:42:41) - Wrap up and reviews
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    43 Min.
  • Deep Diving Legal Due Diligence

    Deep Diving Legal Due Diligence
    May 5 2026
    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 should think about legal diligence in practice, what actually matters during the process, and how deal structure influences risk exposure. They also highlight the importance of seller character, the limitations of diligence, and how buyers can protect themselves when not everything can be uncovered. They discuss: Why legal due diligence is primarily a risk allocation exercise rather than a deal-killing process The three core pillars of diligence including business, financial, and legal and how they work together in a transaction Key legal diligence categories like corporate history, contracts, employment, litigation, and environmental risk The difference between asset deals and stock deals and how each impacts risk exposure and diligence priorities Why seller behavior and trustworthiness can be just as important as anything uncovered in diligence Links: SMB Law Group - https://smblaw.group/ Evan on LinkedIn - https://www.linkedin.com/in/evan-thomson-327a78216/ 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(00:02:08) - Introducing legal due diligence - the three buckets to care about(00:04:37) - What are we trying to do when conducting legal due diligence?(00:09:31) - What to look for when evaluating a business(00:20:16) - Approaching legal diligence in asset vs. stock deals
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    34 Min.
  • How to Negotiate Working Capital in Acquisitions

    How to Negotiate Working Capital in Acquisitions
    Apr 28 2026
    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 working capital directly impacts purchase price, liquidity, and post-close operations. The episode serves as a foundational guide for buyers navigating financial diligence and structuring deals with confidence. They discuss: Why working capital is effectively a purchase price negotiation How insufficient working capital can create immediate cash flow crises post-close The concept of a working capital target and the mechanics of true-ups Common pitfalls, including AR ownership, customer deposits, and prepaid expenses How sellers can unintentionally or intentionally manipulate working capital before closing Links: SMB Law Group - https://smblaw.group/ Evan on LinkedIn - https://www.linkedin.com/in/evan-thomson-327a78216/ 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(00:02:56) - Working capital as a deal killer(00:09:20) - Working capital defined(00:10:39) - Where buyers get tripped up(00:12:23) - Receivables nightmare scenario(00:16:25) - Working capital target explained(00:19:37) - Normalizing and setting targets(00:21:38) - QofE support(00:27:03) - The SBA cash trap(00:33:39) - Deposits and prepaids(00:38:32) - Overdelivery pitfalls(00:41:39) - Handling overdue AR(00:44:18) - Advanced topics(00:47:00) - Final takeaways
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    1 Std.
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