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Main Street Deals

Main Street Deals

By: SMB Law Group LLP
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Summary

 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. Economics Leadership Management & Leadership Personal Finance
Episodes
  • 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 mins
  • 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 hr
  • Small Business Acquisition Strategies That Actually Win

    Small Business Acquisition Strategies That Actually Win
    Apr 21 2026
    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 conversation highlights how buyers can stand out early with brokers, build trust with sellers, and avoid common mistakes that quietly eliminate them from deals. We discuss: Why buyers can win deals without offering the highest price and how sellers evaluate more than just valuation How to stand out with brokers early through speed, preparation, and clear positioning The biggest mistakes buyers make during NDA, IOI, and LOI stages that get them eliminated How to build trust with sellers through communication, relatability, and understanding their motivations Red flags in deals and seller behavior that signal when buyers should walk away 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(00:01:31) - Firm update deal surge(00:03:31) - Seller market and buyer competition(00:05:23) - Non money seller motivators(00:06:21) - Direct to seller vs brokered deals(00:08:40) - Sell side process recap(00:11:45) - LOI flood and broker screening(00:14:27) - Get past the gatekeeper(00:17:57) - NDA mistakes to avoid(00:19:14) - Smart questions and personal touch(00:21:55) - What sellers value(00:23:20) - Win beyond price(00:26:50) - Storytelling over spreadsheets(00:29:43) - When to walk away(00:30:51) - Red flags and noncompetes(00:33:21) - LOI is not the finish(00:35:14) - Diligence communication tactics(00:37:56) - Flexibility and organization(00:41:36) - Finding the right deals(00:42:15) - Wrap up and next steps
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    43 mins
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