Kenneth Cole’s Genius Hack That Sold 40,000 Shoes in 2 Days

Ken Cole had a dream to sell shoes he designed. But it was a bold move at a critical juncture in his career that turned him into Kenneth Cole.

At the start of his career, Ken Cole was like any other entrepreneur - he wanted to break into the big time.

And, like many entrepreneurs, he heard ‘no’ a lot. But it was the time that he wouldn’t take ‘no’ for an answer that created a fashion empire.

Shoe-a-Paloooza

Back when this all happened in 1982, Cole wanted to launch his new shoe brand and make a splash at the New York Shoe Show. This show was held at the Hilton downtown every year and was the premier event where buyers from across the globe gathered.

For any shoe brand, this show was the place to be, but it came with a hefty price tag. Inside the Hilton, 1,100 booths rented at a premium, and outside the hotel, nearby galleries rented out for even more for the two-day event.

With so much competition inside the hotel, and such extravagant prices outside, Cole was seemingly stuck.

With a Little Help From His Friends

Most people might have given up.

Kenneth Cole was not most people.

As luck would have it, Cole had a friend who owned a tractor trailer truck and the friend offered it to Cole.

And that gave Cole his big idea.

He figured that if he could not rent a showroom, he could create his own—right outside the hotel, where he would park the truck and turn it into a makeshift showroom.

Outthinking the Bureaucrat

Cole called the city to get a permit to park the truck across the street from the Hilton.

But the city clerk explained that only two types of permits were available for parking a trailer truck on a New York City street, and Cole met neither option:

1. Utility trucks could get a permit to park on the street, and

2. Motion picture trucks could also get such a permit

Here comes the idea that would change everything:

Undeterred, Cole decided to rename company Kenneth Cole Productions. He then applied for a permit to film a ‘documentary’ entitled The Birth of a Shoe Company. 

Ken Cole got the permit, becoming Kenneth Cole in the process.

History is Made

With permit in hand, Cole parked the trailer directly in front of the Hilton Hotel, rolled out a literal red carpet, and invited buyers to step inside.

Amused, amazed, intrigued, and smitten, the shoe world entered Cole’s domain and over the course of the show, his scrappy, innovative strategy paid off.

Keneth Cole sold 40,000 pairs of shoes—enough to catapult his fledgling brand into the national spotlight.

Today, Kenneth Cole Productions (yes, it is still called that!), is a global fashion powerhouse, but it all began with a big idea, a rented truck, and an unstoppable entrepreneurial determination.

The Takeaway:

When faced with a problem, do not ask, "Why can't I?" Instead, ask, "How can I?" Kenneth Cole's creative thinking during one of the most critical moments of his career is proof that persistence and ingenuity are often the greatest tools of all.

Steal This Strategy!

🎥 Video - Kenneth Cole on Creatively Breaking Into Your Career
Watch Kenneth share the importance of bold creativity.

📖 Book - The Power of Broke by Daymond John
Shark Tank’s resident fashionista explains how being resourceful and scrappy leads to massive breakthroughs.

🌐 Website - Kenneth Cole Productions
See how the spirit of innovation remains central to the brand’s identity.

🎙️ Podcast - The Story Behind Kenneth Cole Productions
Explore how a creative loophole led to one of fashion’s most memorable launches.