Happiness Business

By Bowdoin Magazine

Emily Drappi ’02 loves being hands-on in the happiness business.

Emily Drappi ’02

How did your career unfold?

Looking back at my career now, it’s clear how my Bowdoin education and work experience prepared me to grow and manage our own local, family business—entrepreneurial spirit, innovation, and scrappiness were all key characteristics of each phase of my career. After graduating from Bowdoin, I moved to Boston and started working at a small ecommerce startup called CSN Stores, a company that grew exponentially during my ten years there and eventually rebranded as Wayfair. Early on, the founders thrust me into a role managing the company’s search and email marketing, which in the early 2000s was a very new and ever-evolving challenge. The owners gave me the opportunity to take the lead with it, and that kicked off my career in a direction that I’d never expected.

I was one of the department heads in the Wayfair marketing department for several years when I decided to leave the company in 2013, wanting to enjoy time with our first son, Leo. After a few years of doing some part-time consulting from home, and the arrival of our second son, Marty, we moved to my home state of Maine. My husband, Paul, whom I met at Wayfair in 2003, was asked to launch Wayfair’s Brunswick branch in 2016. I’d always hoped to move back to the Brunswick area one day, so this was the perfect excuse to bring our family home to Maine.

I started working at a marketing agency in Portland called iBec Creative, where I got to work closely with several of Maine’s most successful and fast-growing businesses, helping them develop growth strategies that involved digital marketing, e-commerce, and branding. I loved being able to use my experience in a new way, working with a wide variety of business models and business owners. It was inspiring to see their success and fueled my desire to do something of my own. 

I was still working at iBec when we became owners of Island Treasure Toys in October of 2019. Our plan was that Paul would manage the stores, and I would continue working at iBec and help out a little on the side, but—long story short—I couldn’t keep myself away. I loved being hands-on with our customers that first holiday season, talking to them about the kids they were shopping for, wrapping piles of gifts—it felt like the North Pole. I started doing some of the buying, and I quickly found that choosing the best products for the stores is something I feel passionate about. Seeing the joy on kids’ faces as they find toys that I stocked is so rewarding—I feel like I am a part of their happiness.

It was a tough first year because the pandemic hit shortly after our first holiday season, and we were shut down for months. Our e-commerce experience really came in handy, as we quickly got a website up and running with curbside pickup options, and we even started delivering purchases ourselves—our whole house turned into a logistics center. I was still working full-time at iBec until September of that year, not wanting to leave a job that I loved, but also working nonstop at night on the toy store website and buying and entertaining two kids during lockdown. I finally followed my heart and invested it fully into our toy business, and I have never looked back. Working in-house at Wayfair I had a lot of autonomy and sense of ownership, but it wasn’t mine. Working at an agency, I had great clients who listened and valued our guidance, but their decisions were theirs to make. Having a business that Paul and I could build together? That feels limitless and fulfilling in a completely different way.

At the time that we bought the business in fall of 2019 it was three stores, and we have added two more locations since then. We added a seasonal location in Kennebunkport in 2021 (another case of adopting an existing store from retiring owners) and added our first new location in 2024 on Maine Street in Brunswick, a dream come true to come home to the downtown I once enjoyed exploring as a student.

What inspired you to buy the toy store business? 

After leaving Wayfair, we both knew that we wanted to own our own business someday, and we felt better about building on an existing foundation than starting from scratch, so we started looking for businesses for sale in our area. Just by luck, we discovered that the owners of our favorite local toy store were retiring and looking for new owners to keep it going. It was one of those moments in life where things fall together with an element of kismet—while owning a toy business was never our plan, it now seems like our paths landed us here for a purpose.

What do you find rewarding about it? It obviously seems fun, but it must also have many challenges.

There is nothing more rewarding than having a family arrive in our store, hearing the kids squeal with delight and then scamper off to discover all the fun. And parents and grandparents love it too—everyone feels young at heart in a toy store! It’s wonderful to be able to create that experience and preserve the nostalgia of being able to shop in a classic toy store for a new generation. Year after year, we get to see kids grow and, being their family’s go-to spot for every birthday and holiday, we get to know our community in a really special way.

Are there ways that your academic or extracurricular work at Bowdoin has come into play in your life or career?

I was a psychology major at Bowdoin, and that education was certainly helpful in my work as a marketer, from analyzing audience data to putting myself in our customers’ shoes to identify their needs and motivators. My work-study experience was very helpful, as well. For my four years at Bowdoin I worked as the assistant web coordinator, managing Bowdoin’s web site and doing everything from web coding to creating graphics—those skills were a big part of why I got the opportunities that I did in my early days at Wayfair.

What brought you to Bowdoin?

When I was in middle school, I went on a camp field trip to Bowdoin’s art museum. When I saw the Quad and the beautiful architecture and felt the spirit of the campus, it sounds cheesy but it really was a love-at-first-sight experience. I always pictured Bowdoin when I thought of “college,” and even after touring other colleges, nothing could outdo the feeling of home and aspiration that I’d felt on that first visit to Bowdoin. I applied early and was thrilled to find myself a Polar Bear!

What inspires you?

I love spending time with our customers, helping them shop one-on-one. We do a lot of hands-on customer service helping parents and grandparents to find great gifts for their kids, and I love the very specific challenges that we get. I do all of the buying for our stores, and hearing firsthand what families are looking for gives me great guidance. 

Is there something about your work or life that others would find surprising?

My very first job in high school was actually in a small wooden toy factory in central Maine. We made pull-along wooden toys that were sold at L.L. Bean. I painted a lot of little wooden wheels that year! It was a very elf-ish first job.

Is there something about YOU that others might find surprising?

I think a lot of people are surprised that a small toy store owner got her start working at a large ecommerce company—it may seem a little backwards given how much retail has shifted online. We believe that people really want and miss the connection and customer service that shopping used to have. That’s why we don’t think of our stores as just a retail business but as hospitality too—how do we create an experience that will make our customers want to come in to see us in our stores instead of going online or to a big box store? That’s a challenge with the ease of shopping online and how busy everyone is, but our success proves that there’s a place for a neighborhood toy store. We have team members that people in our communities know and love and want to visit, we are able to give great recommendations when people feel lost and don’t know what to get “the kid who has everything,” we have a uniquely curated selection of toys that are truly high quality, we gift wrap, and in our biggest store in Freeport we have lots of play attractions like train tables, an enchanted closet, and a pretend play market so families can have fun while they shop. You can’t get any of those things at a big box store or by letting a kid make a wish list in an app.

What do you enjoy doing in your spare time?

I love reading and gardening, though lately I’ve been more successful at cultivating weeds and feeding deer than harvesting vegetables. We have twenty-five apple trees and make cider with family and friends every fall with an old-fashioned cider press.

Best Bowdoin memory, or most-lasting lesson from your Bowdoin days? 

Once I got to Bowdoin, I didn’t want to leave. I spent summer on campus every year, working in the communications office as the assistant web coordinator, and then my senior year as an interviewer and tour guide at the admissions office. Being a tour guide was one of the highlights of my time at Bowdoin—I loved getting to see the campus through the eyes of prospective students and their families and helping them to see it as I did on my first visit.


Bowdoin Magazine Fall 2025

 

This story first appeared in the Spring 2025 issue of Bowdoin Magazine. Manage your subscription and see other stories from the magazine on the Bowdoin Magazine website.