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If the Shoe Fits: Drizly, Tough Questions and You

by Miki Saxon

A Friday series exploring Startups and the people who make them go. Read all If the Shoe Fits posts here

5726760809_bf0bf0f558_mDid you see the story of Drizly Bear by founder/CEO Nicholas Rellas on LinkedIn?

Rellas wanted to disrupt the way liquor is purchased.

The idea was pure and incredibly simple: Alcohol delivery, connecting consumers to local retailers at the touch of a button to have alcohol delivered in just 20 to 40 minutes.

The problem is that liquor regulation makes the taxi industry look unregulated.

The question, given the amount of regulation and the fact that it differs state-to-state and even city/county-to-city/county within each state, was where to start.

Where many would have chosen to start in the least regulated market to get traction Drizly took the opposite approach.

We started Drizly in Boston, MA, a city steeped in alcohol lore and one that is so tightly regulated that there are no happy hours.

If you think he was crazy, then he was, as they say, crazy like a fox.

The definition of a tough (or hard) question is one of the the most critical things that everybody needs to know.

And it’s incredibly simple, too.

It’s something that every salesperson learns immediately, but it applies to any industry, field, situation or effort.

A tough question is any question that can draw a response of ‘no’.

Rellas believed if Drizly could address every regulation in Boston, then they could address regulations anywhere — and he was right.

What we formed was a cookie cutter model of adding supply to our network that now scales with minimal capital and human investment and has allowed us to expand to over 18 cities in as many months.

Rellas wraps your take-away perfectly.

So ask the hard questions. Answer them upfront. Be truthful about your answers. There are reasons why great ideas won’t, or didn’t, work. We fight those every day. Some are insurmountable, others are not. Knowing which mountain to climb is as much of the challenge as the climbing itself. But by not asking and answering the hard questions, for a new business or a new line of business in an existing one, we’re doomed to fail from the very beginning.

Image credit: HikingArtist

 

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