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How This Entrepreneur Turned a Sour Job Interview Into a Multi-Million Dollar Pickle Business From an aspiring sneaker designer to a pickle mogul, Travis Grillo shares his journey and thoughts on the future of food.

By Terry Rice Edited by Dan Bova

Courtesy of Travis Grillo

Sometimes, rejection can be a blessing in disguise. Yes, that's truly annoying advice for someone who's recently been rejected, but honestly, it did work out well for Travis Grillo, founder of Grillo's Pickles. After being turned down for a job as a shoe designer at Nike, Travis took a not-so-obvious next step: he launched a pickle company. And that company grew into a multi-million-dollar behemoth, selling products in over 7,000 markets nationwide including Whole Foods, Target, Publix, Stop and Shop, Safeway, Bj's and many more. Here's how he turned a sour moment into a business idea that packed a wallop.

Turning rejection into a lightbulb moment

"After getting denied a job at Nike, I came home and had that lightbulb moment. I decided to start selling my grandfather's garden-fresh, 100-year-old pickle recipe. I started the business out of the back of my 1985 Cutlass Supreme selling at baseball games, parks and the Boston Marathon. Eventually, I upgraded to a hand-built, wooden pickle cart that I set up rain or shine in the Boston Common and was selling 2 spears for $1."

Related: Are You Financially Equipped to Run a Food Truck?

Combining passions

"After not getting the job at Nike, I used my creative design background to bring the brand to life. I created our iconic pickle character, Sam-Sam the Pickle Man, as well as all of the custom gear, which helped us stand out on the streets and spark conversation around the pickles. Being from Boston, the pickle colors of green and white really took off. People would always ask if we were a part of the Celtics but when they looked closer and realized it was pickles, they actually got even more excited. The merchandise was something that came naturally for the brand and has evolved and took us places I never thought Grillo's could go. We've worked with brands like Chalkline and I had my full circle sneaker design moment when I was able to fully design and release my very own Grillo's Pickle sneaker with Patrick Ewing. Now, we're seeing more food and fashion collaborations happen all over. It's really cool to see the food and fashion world work together years after we had our custom gear down at the pickle cart."

Lessons learned from the Boston Common Community

"Some of the best advice I ever got was from the homeless in the Boston Common. To see some of those people smiling just because it was a sunny day was a lesson all on its own. At first, we were invading their space, setting up our cart and selling pickles, but it only took a few days and a couple of tastes of the pickles to get everyone's respect on the block. I think a lot of that had to do with treating human beings like human beings. I would give out free pickles and greet some of the regulars that would sleep in the park every morning. We'd let an old-timer named Garry keep his soda cold in our cooler in exchange for him watching the cart if I needed to use the bathroom or go grab more pickles from storage across the street. Many of the people in the park would never speak to the homeless, but for Grillo's, they were our first customers and the ones that had our back and there was mutual respect. We've been lucky enough to donate pickles to the homeless shelter next to the park and this past February we were a sponsor and participants in the Boston Winter Walk for the homeless."

Related: 6 Years After 'Shark Tank,' This Lobster Roll Food Truck Clawed Its Way to Success

A pickle brand for the people

"Pickles have often always been an afterthought, served warm and soggy on the side of your plate or buried in the back of your fridge until the next cookout. To us, this gives pickles a bad rap and doesn't allow people everywhere to enjoy pickles the way they should be eaten. Other pickle brands are pumped with chemicals, stabilizers and other preservatives to increase shelf life. Now more than ever consumers are more conscious of what they are putting into their bodies, and Grillo's is truly a game-changer. No matter what your background is or where you're from we have made all types of people happy when they try our pickles. Pickles can instantly bring you back to a memory at an old deli or even munching on grandma's homemade pickles. And we've noticed over the years that people seriously love pickles. We get an average of 20 or so posts a day just on Instagram of people tagging @grillospickles in stories, pictures and videos of themselves posing with our pickles. It is truly amazing."

Related: This Pickle Company Bought a Robot -- But Not for the Reasons You Think

The future of food

"The future of food is bright and expanding quickly. We're seeing healthier food broadly available in both major conventional markets as well as small corner stores. The Beyond Meat IPO is a big sign of where the future of food is going and we're proud to be a part of that. Five years ago there were very limited options for plant-based diets. Today you have end caps at markets like Whole Foods promoting Beyond Meat and Grillo's Pickles side by side in some of most prime real estate in the store. Those end caps were filled with real burger meat and shelf-stable pickles even just 3 years ago. We're proud to be one of the pioneers and on the front lines of this new food age."

Terry Rice

Entrepreneur Staff

Business Development Expert-in-Residence

Terry Rice is the Business Development Expert-in-Residence at Entrepreneur and Managing Director of Growth & Partnerships at Good People Digital; an agency that provides marketing and monetization solutions for entrepreneurs. He writes a newsletter about how to build your business and personal resilience and personal brand in just 5 minutes per week and created a revenue optimization checklist to help you multiply your income potential. 

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