This Two-Letter Word Will Destroy Your Company

Aaron Dinin, PhD
4 min readJan 30, 2020

During a recent meeting with an entrepreneur I’ve been advising, he excitedly shared some news: “There’s a big investor in New York who invited us up to meet with him next week. We’re all going!”

“That’s great,” I said. “I hope it goes well. Are you sure everyone on your team needs to go? That’s a big expense.”

“This is a really important meeting,” my advisee assured me. “If we can get this investor on board, we’ll be able to raise our next round.”

And there it was… the two-letter word with the power to destroy any company no matter how large or small. It’s so short and familiar and easy to say that most people don’t notice it. But not me. I’ve spent the past decade fine-tuning my ability to hear it every time it’s used. I’m at the point where simply hearing the word is as jarring as nails on a chalkboard.

Did you notice the word that’s going to cause this entrepreneur so many problems? Again, here’s what he said:

“This is a really important meeting. If we can get this investor on board, we’ll be able to raise our next round.”

The terrible two-letter word is “if.”

It’s unassuming and easy to overlook because it sits at the beginning of a sentence with such a positive outcome. Don’t be fooled. Anytime someone uses the word “if” in the context of describing a business outcome, stop whatever you’re talking about and deconstruct what that deceptive two-letter word really means. You’ll be surprised at all the complexity it’s hiding.

Here are some common uses of the word “if” that you’ve probably heard before. You may have personally used them:

  • “If we can close X% of the leads we’ve got coming into the pipeline…”
  • “If only X% of our website visitors click…”
  • “If we can just get picked up by a couple of media outlets…”
  • “If just one of our videos goes viral…”
  • “If we get just one investor to commit…”

Do you see the pattern? It’s a pattern people deploy when strategizing or planning future steps that come after what has to be done right now. Yes, looking ahead is necessary, but we have to be careful about minimizing all the…

Aaron Dinin, PhD

I teach entrepreneurship at Duke. Software Engineer. PhD in English. I write about the mistakes entrepreneurs make since I’ve made plenty. More @