Legal Mistakes That Kill Deals
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Guest Introduction
Chris Rosselli is a partner at Eversheds Sutherland and an M&A attorney with 25 years of experience representing buyers and sellers in corporate transactions across all industries. Before joining Eversheds Sutherland, he served as deputy general counsel at a Fortune 500 global flooring manufacturer and as a partner at an AmLaw 50 law firm — giving him a perspective that goes beyond the deal table and into how business owners actually operate.
Summary
In this episode of the Power Exit Podcast, John Marsh sits down with Chris Rosselli, partner at Eversheds Sutherland, to unpack the legal mistakes that can weaken leverage, delay diligence, and reduce a seller’s outcome. Chris explains why sellers need to get organized early, involve legal counsel before the LOI is signed, and stay focused on running the business so they do not disappoint buyers mid-process.
Chris also breaks down the practical issues that show up in real transactions, including asset sale vs. stock sale tradeoffs, post-closing indemnification exposure, independent contractor classification, benefits compliance, immigration paperwork, and the founder behaviors that help deals move forward. He also makes the case that price matters most, but certainty to close is nearly as important, especially when sellers are choosing between multiple buyers or entering exclusivity too early.
You'll Learn
- Get organized early, because having documents and data collected, signed, and ready helps sellers stay focused on operating the business during a sale process.
- Involve a lawyer at the LOI stage, because buyers are often led by corporate development teams early on and sellers may gain leverage by negotiating legal points before the process hardens.
- Understand asset sale vs. stock sale, because structure affects both tax treatment and who keeps pre-closing liabilities.
- Spot legal risks before buyers do, especially around benefits, independent contractor classification, and immigration compliance.
- Negotiate indemnification limits early, including caps, holdbacks, escrow amounts, and timing, before those terms reduce cash at closing.
- Stay non-emotional in negotiations, because overly aggressive or non-market positions can slow momentum and make closing harder.
- Evaluate certainty to close, not just headline price, by asking whether the buyer has financing, internal approval, and the ability to execute.
- Create leverage with multiple buyers, keep exclusivity short, and keep backup buyers warm until the wire hits the bank.
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