We all know that the best way to grow is to get out of our comfort zone. The problem with this profound wisdom is that our comfort zone is something we’ve been working to perfect our entire lives, and it’s amazingly comfortable. That’s why I feels it’s part of my responsibility to make founders squirm.

I know that most entrepreneurs have been meeting with enablers -- people who are just too nice or don’t like to make other people uncomfortable. Their startup idea has been nurtured in a loving and supportive environment, and I willingly accept the challenge to wreak some havoc on their universe.

The real world is neither loving nor supporting and it’s time to get a dose of reality.

The Ultimate Squirm-Producing Question

There are many ways to make these new founders squirm. Everyone has their own flavor. Hunter Walk of Homebrew asks founders the Why of your startup? That’s a good one. I’m sure he gets plenty of blank stares and quickly made up answers. Brian Cohen asks founders about how they plan to exit. That will surely put you on the hot seat.

I've got my own arsenal of questions and topics to draw upon, but I’ve got one question that works without fail. It’s such a simple question and so fundamental, yet most people don’t have a good answer. I can pick on these guys now because they are crushing it, but when I started with Digital Ocean at the very beginning, we didn’t know the answer to this. I'll never forget this. We sat in a conference room for a whole afternoon and debated our place in the universe on the day before we were flew to Boulder for TechStars.

Here’s the question:

“What problem are you solving?”

That’s it. I told you it was simple. And yet, it’s so difficult for an entrepreneur to answer.

A Problem with the Problem

Assuming I get an answer at all, it usually falls into one of the two buckets below.

  1. Anything but the problem: The most common response is normally a 5 minute adventure of an explanation about their product, the target market and many other non-problem related pieces of information. It sometimes becomes painfully apparent that the product isn’t actually solving a problem at all. And that’s a huge problem.

  2. Multiple problems: Another typical response is that “We are solving this and this and this and this.” It actually sounds more like, "We are Pinterest + Instagram + Etsy and a little bit of LinkedIn with a side of Facebook and Google.” Although this is slightly better than solving no problem at all, it’s not good. The most successful startups in the world got that way because they solved one problem better than anyone else on the planet, and just solving that one problem is really, really, really hard to do.

A Squirm a Day

The reason I make it my duty to watch founders squirm is twofold:

(a) when they are done squirming, a lightbulb goes off. I force them to think about the really difficult questions that they’ve been ignoring. I help them burn their idea to the ground and hit them with brutal honesty, and ultimately, they come out better for it.

(b) I strongly believe in the new world order of sales — you should only be selling something that you truly believe in to people who will benefit from it. I know that if you aren’t ready to answer some difficult questions about your startup, you’re definitely not ready for development. We want to work with people who are ready to embrace the squirm.

Real entrepreneurs get excited about being put through the wringer. They know that they need to be prepared for these uncomfortable questions if their startup hopes to achieve any level of success. Luckily for them, I won’t shy away from the uncomfortable.