Pineapple Landscaping: Be the Hero of Your Brand
In Polynesia, pineapple means happy home. In colonial America, it was the symbol of warmth, hospitality, and homecoming. And if you live in Chevy Chase, Bethesda, or Northwest DC, it’s the cheerful green and orange logo for Pineapple Landscaping, whose trucks manage to make me grin every time they’re parked down my street. Like its namesake, the business serves up a flavor that is once sweet, whimsical, and friendly. Founded in 2013 by then-13-year-old Alex Neilsen, Pineapple Landscaping has grown into of the region’s largest landscaping companies, with 40 to 50 employees, 1100 weekly lawn contracts, and a diversified suite of services that include deck and patio construction, hardscaping and snow removal. Impressive in itself. But what makes Pineapple epic is its backstory. Half little engine that could, half heartwarming father-son saga, Pineapple doesn’t just leave its history in the past. Pineapple Landscaping is its origin story, with can-do enthusiasm, joy for service, and love of family that reflects in its business model, its customer service, and its ever-smiling brand. Too often, business owners sanitize their brands and keep their personalities, values, and backstory at a cool distance from their customers. But customers are human, and they want to know, like, and trust those other imperfect humans to whom they surrender their money. So build a brand that lets your customers join you on a journey. Let them see you stumble, pick yourself up, conquer big problems, and forge your business around your values. Put simply, they want a hero. Read on to discover how Pineapple Landscaping built a business that takes its customers on a hero’s journey worthy of legend. The Hero’s Journey A decade ago, Alex Neilsen was a Bethesda seven-grader who needed extra cash to buy chips and soda. Bypassing the parental handout, he knocked on his neighbor’s door and offered to mow their lawn. And then he knocked on more doors. His neighbors, charmed by the cheerful determination of the teen mogul, signed up in droves. By 2015, he had 40 weekly mowing contracts. He also had the makings of a solid crew. Alex’s mother is from Spain, so he established an easy rapport in Spanish with other landscapers, who couldn’t help but root for the young entrepreneur and agreed to help him on larger projects. But as his business grew, so did trouble at school. He quit football and spent little time with friends. Teachers, unaware of the budding deal-maker in the back row, complained that he was always on his phone in class. In December 2015, his parents lowered the boom. The business was too big, too distracting. They wanted him to enjoy just being a teenager. Alex listened, thought about it, and approached his dad with a deal: “What if we partner up? You quit your job, and run the business.” Finn Nielsen, not wanting to squash his son’s dreams, humored him with what he thought was an outlandish counter-offer: “Get 100 mowing clients, and I’ll quit tomorrow.” Alex nodded and left to go knock on doors. Two weeks later, he returned triumphant: 105 clients. So Finn, true to his word, quit his job as news director at WNAV Annapolis the next day. Over the next five years, Finn led the business while Alex focused on finishing high school and heading to the University of New Haven for college. If Alex was the risk-taking visionary, Finn was the seasoned integrator. Committed to building a lean business with a healthy cash position, Finn himself mowed 100 lawns each week. He used his experience having owned two Domino’s Pizza franchises to implement the “boring stuff” required to build a sustainable business: licenses and registrations, financial projections, and org charts. In 2021, when Alex was ready to return to the business full-time, he stepped into a thriving mid-seven-figure enterprise. A Brand on a Quest From Beowulf to the Odyssey, Star Wars to The Lion King, our best tales share a fundamental path. Joseph Campbell, professor of literature, author of The Hero with a Thousand Faces (1949), and inspiration to George Lucas, famously explained the ur-tale that captures our imagination: “A hero ventures forth from the world of common day into a region of supernatural wonder: fabulous forces are there encountered and a decisive victory is won: the hero comes back from this mysterious adventure with the power to bestow boons on his fellow man.” More recently, marketers like Donald Miller have adopted the hero’s tale as a way for brands to structure a simple, empowering message that positions their customer as the hero: But customers can sniff an astroturf brand engineered on Madison Avenue. The very best brands, like the very best stories, resonate because they are both authentic and timeless. Like Luke Skywalker, Alex is the unlikely hero, itching for something bigger. Finn is Obi-Wan, whose patience and sacrifice guide the hero to his full potential. And all the overwhelming odds against small business success stand in for Darth Vader. A stretch, perhaps. But it’s a mistake to underestimate the psychological pull your customers feel towards an underdog story. Great brands tell stories, but they also deliver But no one falls faster than the hero unmasked. Everyone loves a prodigy, but does anyone look at Mark Zuckerberg and still think of an artless Harvard dropout? Which means your brand can’t just tell a story. It has to embody that story’s values. Pineapple’s brand is family, grit, loyalty, and community. “I like to think we’re very much a family-friendly kitchen table landscaping company,” Finn explains. They wanted a company “built on their DNA”: lean, fairly priced, hyper-local. For Pineapple, that’s not a gimmick, it’s a promise. Alex and Finn answer their own phones, and their personal mobile numbers and emails feature prominently on the website. They both go on calls with new clients, and Finn is still known as the “mobile pit crew,” scurrying around town to repair the odd lawnmower for his team. Some longstanding clients find themselves on a fixed income,
