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VCs expect to ask for better terms, make a comparison shop, and use the leverage you have, but not after reaching a deal. It may seem obvious that this founder acted recklessly and unethically, but in the feverish pitch of deal-making, even smart and well-meaning people can lose sight of the fact that VC trading, under all term sheets and financial forecasts, is a process in which people decide who they want to connect with for years to come. In VC relationships, as in any long-term partnership, it is much easier to build trust than to rebuild it. If you find that you`ve agreed on terms without sufficient compensation or that you`ve made commitments that you`re not able to meet, you`d better play it directly: “I think I may have accepted something I don`t really feel comfortable with.” This will be an unpleasant conversation and the VC might not be ready to reopen the discussion. But there is a good chance that you will get a better result than if you break your promises, if they become expensive or uncomfortable. Venture capital is a small industry and, as one entrepreneur says, “In my industry, you don`t have a resume. You just have your reputation.┬áMany other terms obviously warrant careful consideration in every VC negotiation. My interest here is simply to highlight the importance of understanding the consequences of seemingly abstract provisions on the roadmap and to highlight how the decisions made by a VC during negotiation can serve as useful signals. A negotiator from the National Football League once told me that the only way to really understand what is at stake in negotiating a collective agreement with the players is to compare the agreement with a marriage. Except, he added, his negotiations are more difficult than marriage: “You can divorce your spouse, but we can`t divorce players.” After working with many founders who have negotiated with venture capitalists, I believe a related metaphor helps to grasp the economic and emotional issues associated with it: founders are like single parents who are looking for a spouse who loves and cares for their children as much as they do. And yet, despite the enormous value that can be created with a VC-entrepreneur partnership, these negotiations can lead to poor results.

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