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Make No Expensive

For an investor, a no is reversible. A yes is not. Every fundraising tactic that works falls out of that one asymmetry.

An investor can say no to you today, watch you land a big customer next week, and say yes on Friday. Nothing has been lost. Their optionality is fully intact.

But if they say yes and wire the money? They don't get to call you next Tuesday and go "hey, actually, give it back." Doesn't matter what happens to your company. Doesn't matter what happens to the market. The yes is permanent.

This is why so many investors say "too early" and "keep us posted." Every day they don't invest is another day's worth of information they gain to make better decisions.

So, the fundamental question is simply "why would an investor ever say yes?"

Because they believe their no is about to become irreversible.

Most founders get this backwards. They spend months trying to convince investors to say yes. That's the wrong target. Your job is to make no expensive.

I've been starting and coaching companies for thirty years and I promise you cannot throw a fundraising question at me where the answer doesn't come back to that one asymmetry. Deck structure, follow-up cadence, term negotiation, party rounds vs. leads, when to walk away. All tactics. All downstream of the same truth.

If your fundraising isn't working, you're probably still trying to earn a yes.

Make it impossible for them to say no.

Eric Marcoullier · Obvious Startup Advice
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