What is your “why now”?

Every successful company has a clear “why now.”

You’re probably not the first person in the world to come up with your particular business idea. If that’s the case, you have to ask yourself: why doesn’t this business already exist? There are two options:

Option 1: it doesn’t exist because it’s a bad business, and you just don’t understand why yet. (Said another way: people have tried and failed to start your business in the past, which is why it doesn’t currently exist.)

Option 2: something has changed in the world that now makes this business possible, in a way that wasn’t possible previously. What is the unique combination of conditions that make now the right time for your company? This is your “why now”.

If you’re not sure what your “why now” is, you should be nervously asking yourself whether you actually have an “Option 1” business.

Let’s make this concrete with the example of Pilot. Pilot didn’t invent the idea of doing accounting for companies—or even the idea of “Maybe the computer should help a team of people do the accounting for companies.”

So why didn’t Pilot already exist? Per above, either there’s something about the business that makes it a terrible business that’s doomed to fail (and we haven’t yet discovered it), or there’s something that’s changed in the world that now makes it possible.

In our case, there are two developments that make Pilot now possible, in a way that would have made it impossible to build Pilot in 2007:

1. Everything is now in the cloud, and everything has APIs.

   
   When we were starting our first company back in 2008, the following things literally did not exist: Expensify, Gusto, Rippling, Stripe, Brex, Carta, Plaid, QuickBooks Online. Your bank statement arrived at your office in an envelope, in the mail.
   
   Said another way, the building blocks for our business simply didn’t exist until comparatively recently.
   

2. Consumer behavior has changed. Ten years ago, you might’ve wanted to meet your tax preparer at their office, bringing in your shoebox of receipts. Even if it were technically possible, being remote was a bug, not a feature. These days, you’d much rather interact with your team online, and this trend has only further been accelerated by the pandemic.

If you have aspirations to build a large, iconic, enduring company, you have to understand the thing that enables it—your “why now.”