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
  • The SMB Acquisition Process Explained - Main Street Deals #10

    The SMB Acquisition Process Explained - Main Street Deals #10
    Apr 7 2026
    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 competition has evolved, why the process is more complex than it appears, and how buyers should think about risk, timing, and execution. Throughout, they stress that while the deal process is demanding, it is ultimately just the pathway to owning and operating a business. They discuss: Why financial diligence is the biggest risk to blowing up a deal post LOI The step-by-step acquisition process from sourcing to closing and integration Brokered deals vs proprietary deals and the tradeoffs of each approach How to structure and negotiate a strong letter of intent Realistic timelines and why most deals take 10 to 12 weeks post LOI 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(00:00:58) - Market update and deal flow(00:03:18) - Why buying is harder now(00:05:54) - The acquisition process overview(00:08:14) - From LOI to integration(00:12:18) - Where to find deals(00:13:00) - Brokered deals pros and cons(00:16:26) - Proprietary deals reality check(00:18:42) - First-time buyer advice(00:20:24) - Market reality check(00:21:44) - LOI basics explained(00:22:59) - Why an LOI de-risks deals(00:26:53) - Staging diligence spend(00:29:54) - Three stage deal map(00:35:45) - Herding stakeholders(00:40:00) - Final wrap and thanks
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    40 mins
  • Planning for Acquisition Costs - Main Street Deals #8

    Planning for Acquisition Costs - Main Street Deals #8
    Mar 24 2026
    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 operational realities that sit beneath the headline purchase price. Along the way, they share hard-earned lessons from working with buyers navigating SBA-backed acquisitions and raising capital for the first time. They discuss: - Why the true cost of a deal extends far beyond the purchase price, often by hundreds of thousands of dollars - The most commonly overlooked expenses, including legal, quality of earnings, bank fees, and hidden taxes - How insufficient working capital planning can quickly lead to cash flow issues post-close - What SBA loan structures actually look like in practice and how they impact deal flexibility - How buyers should think about seller notes, equity raises, and building a strategic investor base 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(00:03:27) - Buyer journey post loi(00:05:48) - Sources and uses basics(00:08:58) - Working capital cash buffer(00:11:33) - Deal expenses reality check(00:12:25) - Qoe and legal budgeting(00:16:50) - Bank deposits and refunds(00:19:08) - SBA guarantee fee explained(00:21:01) - Hidden costs of vehicle sales tax(00:23:14) - Vehicle sales tax shock(00:25:00) - True transaction cost math(00:29:14) - SBA loan percent rules(00:34:11) - Demystifying SBA closings(00:36:54) - Seller note myths(00:40:09) - Line of credit traps(00:42:14) - Equity raising reality(00:45:46) - Strategic investors value(00:47:54) - Wrap up and contact
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    49 mins