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How These High School Best Friends Started

Their own successful business from their bunk beds!

Image by Flagpole
There are so many dreadful stories of couples and friends who start a company together, then seeing both the business and the relationship go down the tubes. It’s to be expected on most cases, because starting a business is very stressful, especially when you are doing it with someone that you have to see daily inside and outside of work!

Many entrepreneurs that create a business with a romantic partner or a best friend usually end up with broken finances and shattered relationships. Starting a business can be a “sink or swim” situation. However, there are a selected few who are passionate, tenacious and lucky enough to swim throughout the journey of starting a business and flourish!

Megan and Jaime of Flagpole are an example of two best friends who met while attending high school and quickly became inseparable. They didn’t have any experience, which is one of the biggest deterrents to launching a business for anyone. As teenagers, they didn’t have the finances, but they possess a “Don’t just do the walk, talk the walk” attitude.

Despite what you might think, you don’t actually need a ton of experience or a lot of money to get started. I had the wonderful opportunity to interview two young entrepreneurs and best friends recently, Megan and Jaime, who worked out of their beds for about five years when they first started their business. They launched Flagpole, a successful fashion brand that uses the highest quality Italian fabrics by artisan tailors in the heart of New York City’s Fashion District to produce each designer swimwear collection.

BL: What positive qualities do you bring out in each other?
MEGAN AND JAIME: We are both constantly pushing each other beyond our limits to be better. Whether it’s over a design or a new website feature, we are always openly critical. I think honesty is something we bring out in each other. We are not afraid to disagree or express disappointment. On the other side, we are both fiercely protective and supportive of each other. We really just bring out all the raw emotions.

BL: What’s one thing you gave up that made you more successful in your career? For ex., it can be a habit, behavior or mindset that was holding you back. How did you realize you needed to drop it, and how did making that change boost your success?
MEGAN AND JAIME: We both had to let go of the mindset that owning a company was just about us and our vision. We represent women all over the world and in being open to their feedback, we have created better fitting and looking suits than we could have ever imagined designing on our own. When we started it was just the two of us doing everything from our living room. We had to let go of the habit of only relying on each other and opening up to asking for help from others. One thing we both do to help us cope with the stress and pressure of running a business is go to therapy. Having an outside voice and safe place to vent our personal and work frustrations has been paramount to our success.


BL: What have you done to set boundaries on your work time — and what happened next? For ex., boundary-setting could include: refusing to schedule meetings at certain times, using apps to monitor your own behavior, or setting aside sacred time for certain activities you care about/don’t want to miss. What has worked for you? What hasn’t?
MEGAN AND JAIME: When we started this company we lived in bunk beds and we worked all the time. We would start and end our day with conversations from our respective bunks which is exactly as unhealthy as it sounds. We wore each other out through making our home and even our beds a space that felt like work. We eventually moved our office out of our living room, but going to and from work together still didn’t help to set any boundaries. After five years of living in our bunks, we decided that for our friendship and for our company, we needed to move out. This allowed for us both to have a personal space to turn everything off. Now that we have an office we have a set space for work, and when we leave, it’s much easier to switch conversations into that of just friends. For big activities that require taking a vacation it’s very hard not to feel guilty for missing even a day of work. That’s when we look to each other for reassurance and support to feel like it’s okay to miss a day here and there.


BL: How did you come up with such a unique name for a fashion brand?
MEGAN AND JAIME: When we first came up with this idea, we knew we didn’t want to name it after ourselves. We always hoped it would be bigger than just us and we wanted a name that we could expand under. We chose Flagpole because it’s the unofficial name of the beach we grew up on together in South Florida, and it felt like something that could grow and expand as far as we hoped we could.


BL: Why Flagpole — how does it different from other brands?
MEGAN AND JAIME: We push quality and fit above all. We are super grateful to make everything here in NYC right under our nose so we can ensure that every piece baring the Flagpole tag is up to our high standards. Personally, we also love the way everything looks, but we might be biased. 


For more information about Flagpole, visit here.

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