The 4 Most Important Questions to Ask Yourself as a New Founder

Editor’s Note: This article was first published by Inc. here.

There are plenty of reasons to start a company.

But when hopeful founders reach out to me and ask for advice, I typically tell them to ask themselves one very important question: “Why now?”

What you’ll discover by asking this question is the mega-trend that’ll propel you forward.

For example, the “why now” reason I’ve had for starting my last five companies is that I have seen an undeniable shift – a massive change in our world. In other words, a mega-trend.

When my co-founder, Elias Torres, and I started Drift six years ago, we saw two things happening. The first was that at the time, there were limited options and so companies could dictate the selling process.

But all of a sudden it seemed like supply was infinite and the power was shifting to the buyer. However, all the tools that existed – such as customer relationship management (CRM) to marketing automation systems – were built for the seller. We recognized that all the tools that businesses used to sell and market to get new customers and retain existing customers would have to change.

That was a massive shift – but it wasn’t enough. We knew that we then had to figure it out. We asked ourselves if this shift is happening, what are the set of megatrends that are forcing us to adopt an entirely new behavior? How are habits changing? And can we use that behavior change to enter and re-segment an existing market?


There were a lot of changes, but one stood out to us. Everyone – from kids to grandparents to co-workers – was shifting to a messaging-first life. Messaging was the new primary way of communication.

And because of those two mega-trends, we thought we could ride that behavior change that we believed was happening – and is still happening today.

Now six years later, everyone across the globe is living through one of the biggest, if not the biggest, undeniable shifts in our entire lives. And that is Covid-19.

The pandemic has forced us all to adopt entirely new habits – and is an opportunity for current and future founders and leaders to think about how to resegment an existing product, create an entirely new category, or company, or an entirely new product or service line.

If you are looking for your “why now,” here are three more questions you should consider:

1. Who is your competition?

You’ll want to name your enemy. In every good story, there is an enemy. For us, it was forms. We knew that the current B2B customer didn’t want to fill out a form and wait for someone to get back to them just to answer a simple question (if they heard back at all). Ask yourself who you’re up against and consider how you’ll offer the better product or service.

2. How will you help customers win?

When you name an enemy, you prep people to wonder, “Okay, so how can I win?”

For our company, we helped people to have conversations, at any time, on their own terms. Whatever your answer is, it should be clear that your customers couldn’t achieve that without you.

3. Who else has done something similar?

This is a key part of answering “why now.” If something seems like a good idea, it could have also been a good idea three years ago. If you’re not seeing a direct example, here are two explanations. Either no one ever thought of it (which is highly unlikely), or, more likely, someone else tried it and it didn’t work.

Learn from history. Dig in and figure out why this didn’t work one, or three, or five years ago.


Three years from now there will be a huge uptick in new companies that are based on the habits we formed in the last year. But be prepared to answer the question, “Why now?”

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