How a Decade of Pickles Taught Me to Build Boldly}

How a Decade of Pickles Taught Me to Build Boldly

Reintroductions & New Beginnings

There are lots of new faces around here lately, which makes this the perfect time to reintroduce myself — and share a bit about how we got here and where we’re headed next.

I’m Charlotte, co-founder of Olive My Pickle, which my husband Shai and I started back in 2010. What began as a few barrels of pickles and olives at the farmers markets became a decade-long adventure in entrepreneurship, creativity, and, let’s be honest — sheer persistence.

Bootstrapped from the start, we were up before dawn for the markets, hand-labeling jars late into the night, and patching together equipment however we could. (The panels for our very first walk-in cooler? Pulled out of a dumpster.) Our young boys were our unofficial crew, helping where as best they could before we could afford to hire anyone. It was scrappy, imperfect, exhausting, and deeply rewarding.

The Early Hustle

For the first eight years, our Saturdays were spent at the markets, meeting customers face-to-face and learning what they loved. During the week, we’d deliver to a growing list of natural food retail stores — at one point, more than 40 stores across Florida. We’d load up the box truck, drive for hours, set up tasting demos, and talk to anyone who’d listen about gut health and live culture ferments.

Then, in 2018, everything changed. Our two largest retail partners, Lucky’s and Earth Fare, went out of business within months of each other. Practically overnight, what we thought was the future of our business disappeared.

That’s when Shai and I looked at each other and said, “It’s e-commerce or bust.”

Building Online, Brick by Brick

We kept the farmers markets going while learning how to sell online — from scratch. Shai’s talents have always been in operations and product development. He not only refined our recipes but engineered custom fermentation systems to solve the many growth problems over the years– today he holds many unofficial patents for these inventions.  

Meanwhile, I took on the brand and marketing side. I became a self-taught digital marketer — watching YouTube tutorials, writing blog posts, shooting photos, copywriting slogans, learning SEO, designing packaging, running ads — whatever it took to move the needle.

And when the spreadsheets and screens were too much, I stepped away and turned to color.

Color as a Lifeline

I’ve always been obsessed with color and style. When I needed to reset, I’d pick up a can of paint. Sometimes it was hand-painting a market sign, stenciling a spray painted mural on the warehouse wall, or I’d need to work out a new label color palette that no one asked for but I had to try.

We didn’t have any budget, so I created with what was around me — dumpster diving for display props, turning scrap wood into signage, and collecting spray paint colors, (I still have a hard time throwing away empty cans of my favorite shades.)

Those projects were more than creative outlets — they were my lifeline. When you’re bootstrapping for years on end, creativity becomes a kind of survival skill. It gives expression to hope — and when the sales aren’t there yet, making something with your own hands can feel like proof that progress is still happening.

Over the years, I’ve collaborated with incredible designers and artists who helped bring our brand to life. While I can stencil a sign and spray-paint a barrel, it took a community of creative people to fully express what Olive My Pickle would become.

Twelve Years In

It took over a decade for the business to really turn a corner financially. That’s a long time to keep the faith. There were plenty of moments when it would have been easier to stop — but I kept coming back to the act of making things. From painting warehouse shelves hot pink to hand-stenciling pickle barrels, those creative pursuits helped me make sense of the long arc of the journey. Life felt like a blank canvas, and I was creating my own masterpiece — one can of spray paint at a time.

Because at its core, creativity and entrepreneurship aren’t all that different. Both are about seeing what doesn’t exist yet and solving every single the problem that stands in the way of getting there.

The Pickle Factory: A Creative Homecoming

In 2024, after years of earned status as rockstar merchants at the farmers markets, we opened The Pickle Factory — a brick and mortar retail space that celebrates all things pickles. 

Somewhere between choosing the wall colors, designing signage, and merchandising the space, I realized I’d come full circle to my original (pre OMP) career roots in retail, fashion, and lifestyle brands. The process of creating The Pickle Factory reignited a love I hadn’t realized I’d been missing: the joy of expression through style, texture, products and storytelling.

The Pickle Factory became not just a store, but a celebration — of pickles, yes, but also of creativity, community, and connection.

Because Pickles

Meanwhile something else was fermenting. Over the past year and a half, I’ve been pouring that same energy into another project: Because Picklesa fashion and lifestyle brand inspired by joy, food, and humor.

When I first dreamed up Because Pickles, I had the concept and the name — but it wasn’t until I met illustrator Marianna Fierro that everything finally clicked. Mari’s playful food illustrations and color-happy sensibility give Because Pickles its visual soul. As Creative Director, she brings the brand’s world to life in every detail, which lets me focus on steering the marketing and business development side of things.

We like to say that Because Pickles is for people who take their snacks seriously and themselves a little less so.

Join the Jar

So that’s where the journey has led! From barrels at the farmers market to an e-commerce pickle business, from murals and spray paint to a retail space and now a lifestyle brand — it’s been a long, wild, creative, humbling ride.

I’m beyond excited to share this next chapter with you.

👉 Come see what I’ve been working on — explore BecausePickles.com, follow us on social, and (as we like to say) join the jar.