7-Figure Negotiation Mistakes Founders Make When Selling Their Business with MIT’s John Richardson

Most founders think they’re not great negotiators. John Richardson thinks they’re wrong. Richardson has spent decades teaching negotiation at MIT’s Sloan School of Management and before that at Harvard Law, where he was an associate at the Harvard Negotiation Project and co-authored foundational texts with Roger Fisher and Howard Raiffa. His new book is called Never Settle. In this episode, you discover how to 

• use a “best guess” about a buyer’s motivations to get them talking, even when they’re deliberately keeping their cards close 

• reframe yourself as the first offer at the table, so you walk into every conversation with leverage you already own 

• prepare for the emotional flood that hits founders in high-stakes negotiations, and the neuroscience-backed technique that short-circuits it 

• tell the difference between a buyer who’s genuinely nervous about AI disruption and one who’s using uncertainty as a bargaining chip 

• respond to a retrade without blowing up the deal, including the exact language Richardson recommends 

• avoid the trap of stating a non-negotiable term too early, and why doing so often ends negotiations before they begin 

• find out why the highest offer is not always the best deal, and how to build a personal scorecard that reflects what you actually want 

Show Notes & Links

Check out Never Settle: Persuasion and Negotiation Skills to Get What

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Definitions

Due-Diligence: This is a comprehensive appraisal of a business or investment undertaken before a merger, acquisition, or investment. It seeks to validate the information provided and uncover any potential risks or liabilities.

Earn-out: This is a financing arrangement for the purchase of a business, where the seller must meet certain performance goals before receiving the full purchase price. It reduces the buyer’s risk and aligns the interests of both parties post-acquisition.

Roll Over Investor: A rollover investor, in the context of selling a business, refers to an individual or entity that rolls some of their proceeds from the sale with the buyer. This strategy allows the seller to defer capital gains taxes and potentially leverage their expertise or resources in a new venture.

Re-Trading: This occurs when a buyer attempts to renegotiate the purchase price of a deal after initially agreeing to one. It is often seen unfavorably as it occurs after due diligence, seemingly exploiting newly discovered information.

TAM: “Total Addressable Market.” It’s a business term that represents the overall revenue opportunity available for a product or service in a specific market. To put it simply, TAM is the maximum amount of money a company could potentially make if they captured every single customer in a given market who might be interested in what they’re selling.

About Our Guest

John Richardson

John’s path to negotiation began with family tragedy. His father lost his brother Syd, a pilot killed over Germany in WWII, which devastated his dad for life. Years later at Harvard Law, John met Roger Fisher, co-author of Getting to Yes, who had flown weather missions in that same war. Fisher’s plane inadvertently helped the Enola Gay drop the atomic bomb on Hiroshima while schoolchildren were still outside, a burden Fisher carried forever. It drove his life’s mission: save the world from war through better negotiation. That same mission now applies to the daily conflicts in our relationships and workplaces. John is a MIT Sloan School of Management Lecturer on negotiation.