- April 3, 2025
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You’re minding your own business, running some errands on some unassuming day when you see it. That first glint of green. First a table, then some sashes. Then boxes and boxes of Girl Scout cookies. Depending on who you are, you either run toward this serendipitous encounter with delicious treasure, or you do everything in your power to avoid temptation.
Either way, if you’ve been living in Lee county for the last dozen years or so, there’s a chance you encountered high school senior Olivia Trader. The 18-year-old has sold over 50,000 boxes (50,264 at the time the Business Observer interviewed her) of cookies since she first joined Girl Scouts in first grade. Spread over 12 years, that's good enough to set an all-time cookie sale record for the Gulfcoast Council.
Beyond that record, Olivia, a senior at the The Canterbury School, a private school in Fort Myers, has several other Girl Scout accolades. She won the Girl Scout Gold Award — Scouting’s highest award — with a 100+ hour project to prevent violence against women. She's been a delegate at the National Council Session of Girl Scouts USA where she spoke at the United Nations’ 67th Commission on the Status of Women and, notably, she's been pictured on the front of a cookie box.
That doesn't mean cookies came easy to Olivia.
“My first cookie booth, I was too scared to ask anybody standing outside the Publix if they wanted to buy cookies,” Trader recalls. “And it was super intimidating at first, but as I got more used to it, and I kind of started to develop my own identity, my own sense of self, I was able to not only become confident who I was, but who I was as a cookie entrepreneur as well.”
Over time, Trader began to hit her stride. Her first year, she set a goal of selling 1,000 boxes — and reached it. Every year she added another thousand to her goal, as she continuously refined her selling technique.
Trader's stride includes something that can be a lesson for anyone in sales, at nearly any time: don't forget to smile.
“Some of the sales tips, I would say, at cookie booths that were really effective and some of these are going to sound cheesy and basic, but they are what worked for me,” Trader notes. “One of my biggest tips was always having a smile on my face, because unfortunately I have actually walked past a lot of Girl Scout cookie booths, and they're not really smiling. They're not really engaging with customers all that much.”
That confident approach worked quite well, but isn’t always enough to close the deal.
“I feel as though at this point I've heard about every single excuse under the planet,” she says of why potential customers reject a sale.
That's everything from being vegan, to gluten free, to diabetic. In those cases, it’s a matter of being armed with product knowledge. Thin Mints, the highest selling cookie, are vegan, she might say. Or Toffee-tastics, first introduced in 2017, are gluten free. For those who can’t have any sweet treats, there’s an option: How would you like to buy boxes for troops overseas?
Even for her lowest seller, Lemon Ups, Trader's technique came from a fortuitous encounter with a stray lemon. Someone had dropped a lemon in the parking lot at Publix. When she went to turn it in to the store, the manager told her to keep it. She placed it by the Lemon Ups boxes and noted a sudden increased interest. From then on, she put a lemon out by those boxes.
Not all customers are sweet.
Trader notes, “People aren’t usually as open to the idea of an older Girl Scout. And I find that really sad because you can be a Girl Scout at any age. You should be just as welcoming to go up to that cookie booth and say yes to the cute little girl or to the more developed, more mature teenager who's out there as well.”
She says that it can be discouraging to middle and high schoolers who end up dropping out because they feel they’ve aged out of the program.
Aside from these hurdles, which are relatively universal, the biggest obstacle came while in seventh grade.
In 2018, she won the National Cookie Pro contest and was able to travel to New York, meet several industry CEOs and was also featured on a Tagalongs box. Then, 2020 was supposed to be the debut year of the boxes with her likeness and was also the year she aimed to sell 7,000 boxes. She was standing at a cookie booth when her mom got the call: all booths would be shutting down due to the pandemic.
“I was just in total despair because this was supposed to be my big year. And then after that, I decided, you know what? I'm not going to quit. I'm way too far along to quit now, so I decided to try and come up with fun ways to make the most of my situation.” Trader says.
She changed up her strategy completely. She called everyone on her contact list offering contactless delivery, jumped on social media and even offered a roll of toilet paper for every case sold when that was quite the valuable currency.
It all paid off: She sold 7,616 boxes of cookies that year and it was then she decided to make her personal goal selling 50,000 boxes.
As her senior year of high school winds down and her time with the scouts comes to a close, Trader is ready to put all of her adventures and life skills learned over the years to work.
“I've decided that I want to go into business, and specifically marketing and advertising,” she says, with ambitions of being the head of her own agency.
Now, looking back on hours of service and projects and cookie sales, she has advice for the next generation: “Take advantage of every single opportunity, and don't just stand there and wait for somebody to open the door for you.”
