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Keep your existing investors engaged and excited. The other piece of advice that I hear myself constantly reminding our companies of is to keep the existing investors engaged and excited. Too often, those monthly emails or short phone calls or coffee are taken for granted. Sure, entrepreneurs are busy. But investors start to wonder how the company is faring if they don’t hear anything. In the case of a seed extension, it’s imperative to keep the momentum, especially when the Series A marketplace may provide a negative signal. Little nuggets like customer anecdotes, compelling stats, etc. that the partner on the deal can share with her/his partners help keep up the momentum.
Gut check the insiders. When the company appears to be heading towards a seed extension, with a minimum six months before cash out, it’s wise to start taking a gut check of the current investors. Who plans to write the extension check and for how much? Some funds are automatic in the extension, some will do pro-rata of the total raised, some insiders will price/others will not.