Startup Lessons from the Worst Drink in Chicago

“It tastes like Havarti and Ross Perot.”

As far as I can tell, any reaction to a shot of Malort, Chicago’s weird-horrible-wonderful liquor, is equally appropriate.

My own response was a cross between confusion and disgust. Am I supposed to pretend to be liking this?

I downed the shot with my old friend Mason at a bar near his place out by the Cuban neighborhood. West Coast transplants to the midwest, we caught up quickly on almost 10 years.

We had our shots. He made fun of my reaction. And said the only appropriate thing: “Welcome to Chicago.”

Malort is bad. Malort is memorable. And, for all its craziness, Malort is a perfect case study for startups working to differentiate themselves.

Here’s why:

1. It’s the stuff of occasions.

Let’s be clear, nobody is drinking Malort on a regular basis.

But when you’re with people who you let your guard down with and you want to share a moment of joy with, you take a shot of Malort.

Reuniting with a friend: Malort.

Peer pressured at work: Malort.

Nobody needs or wants it every day, or even regularly. Which seems like a bad example for startups to follow. But what the drink company understands - that a lot of entrepreneurs forget - is that its purpose is limited.

More than what it is, the makers of Malort know everything they’re not.

They know you won’t drink it when the in-laws come over. That you won’t casually sip it throughout a dinner party, or make mixed drinks from it.

Rather than strive to be those things, and find wider acceptance, they’ve dug their heels in.

Here’s how the label reads:

"Most first-time drinkers...reject our liquor. Its strong, sharp taste is not for everyone."

When you’ve written a book, launched an app, built a platform, or started a service, it’s easy to convince yourself that what you’re doing is going to grab people’s attention and hold it. It’s easy to see everybody making it a central part of their lives, to keep reaching for it tomorrow and the day after that.

Hit product-market fit and they'll come crawling.

Hit product-market fit and they'll come crawling.

But it’s not that easy. Conversion rates are notoriously low, even when companies make huge improvements. Lots of people will straight up not like what you are offering.

And rather than strive to convince them otherwise, startups would do well to heed the Malort strategy.

Give people a moment. Give them a memory. Not where there wouldn’t be one, but in a way that puts your product as the main character.

Think about this:

In addition to the Malort, Mason and I had a couple of beers, and had a great talk.

But I don’t know the name of the beer. I don’t know the name of the bar. And, if you noticed, I don’t even remember the neighborhood.

What I remember and what I tell people about is my moment with Malort.


Make something so impactful that people tie their memories to it. To do that, you either need to create a new category for yourself or do the same old thing in a way nobody else is.  


2. There’s no middle ground.

Malort is a Chicago thing, but it’s actually pretty hard to find even in the city that birthed it.

It’s typical to ask a bouncer if their bar serves Malort, only to be met with a confused look and a Never heard of it. You can expect those who know about it to laugh in your face.

This is all part of it.

They make you go out of your way to find it, and embarrass you in the process.

Youngme Moon refers to brands like this as hostile brands, who take a unique approach to growth:

“Instead of laying down the welcome mat, they lay down a gauntlet.”

The hostile brand mold was made for brands like Jeppson's Malort. 

If they wanted it to be accepted and accessible, they wouldn’t have made the drink taste so bad. They would have modernized their design. They would have made a typical type of liquor and got a place on the (top or bottom) shelf at every bar in town.

Instead they created a category for themselves.

In doing so, they made something with personality. And by drawing a line in the sand between the people willing to go out of their way for a taste and those who stay in their lane, Malort creates pride.

Not many brands actually succeed in that.


Being accessible and being accepted means you risk drifting into the background of people’s lives. Erecting barriers to access and acceptance forces people to choose which side they’re on. If your product is worth it when they get there, at least some of them will end up on yours.


3. It challenges your assumptions.

On the surface, Malort doesn't give you anything you want, especially not in a drink. 

Nobody would speak up in a focus group for "more burnt orange peel" or say that "the hints of broken dreams are too faint".

But as somebody told by startups and dinosaur companies all day every day that consuming their product is evidence of my good taste, I can’t help but want to sign on with somebody who won't play the game. I like a company to move me out of my comfort zone, disrupt my routines and, geez, even mess with me a little bit.

Malort is a friend you don't agree with on paper but is still pretty damn cool.

Why - when there’s so many startups trying to make me comfortable - would I want something that’s the total opposite?

Because everybody is solving the obvious problems. I can get those things any time I want.

But companies solving those more nuanced problems - especially things that run backwards from logic like Malort does - are a rare thing to find. 

That this one also gets you buzzed is almost too much.

I start things and help people.

Kyle CrawfordComment