Making It with Jaime of Flagpole NYC

It was the August 2014 Vogue that introduced me to this swimsuit company, Flagpole NYC. The Stephanie suit that graced it’s glossy pages stood out to me because of its silhouette, shapes, and colors: a high-waisted bikini, with geometric color blocking of black and cobalt blue. I illustrated it. I posted it on Instagram. Then Flagpole reposted it. I was shocked! They were in Vogue! I had just graduated from university. And that was the start to our relationship. 

Fast forward almost ten years. I interviewed Jaime back in February when I was in New York for Fashion Week. What a different time and a different world we lived in only six months ago!  It was my second time visiting the co-founders, yet I still felt like I was that fresh- out-of-university girl geeking out about the ladies who were featured in Vogue. My nerves about meeting up after not having seen or talked to Megan and Jaime in years had me a little too cautious about my commute time. I ended up arriving in Brooklyn early, so I lazily walked around in the rain to kill some time. I made it up to the floor of their studio, still a few minutes early. I continued my lazy walk, gawking at the rad space they got to work in before I arrived. I shyly knocked on the door because I felt so unofficial, unlike this building and the other people I’ve seen walking around. But as soon as the door opens, I’m welcomed by a ginormous “Hello!” from Jaime followed by a hug. I’m taken aback, but then I remembered she’s from Florida. We Southerners hug, though I’ve lost that form of greeting since having lived in the West. For a second her greeting made me forget my nerves and we were talking like this relationship was founded organically, and not through Instagram reposts and likes. 

This interview took place just shy of a month before Covid-19 shut down our lives and I can’t help but feel like Jaime’s words are timely. She’s warm. She’s kind and inspiring. Jaime opens up about starting a business in her twenties and how her thirties have given her a new perspective. From self-care to imposter syndrome, Jaime’s insights are very...well, insightful. 

To help the reader, the following transcription of my interview with Jaime is edited and organized under a few headings that indicate key themes. 

THE STRESS OF RUNNING A BUSINESS

Stress affects your body in every way and you don't realize it until shit is hitting the fan. Megan [Flagpole NYC’s co-founder] and I will take care of an infection that we got in our bodies because we just weren't drinking enough water, and it’s after assessing why we were sick that we realized it was because of stress. 

In the past two years Megan and I have changed our mentality. It started when we turned 30, but 31 for some reason was a really formative year for us. We weren’t prioritizing our physical and mental health because of how we were running our business. For example, the push and pull we have with our investors—it’s extremely stressful! But I need to make sure that I’m taking care of myself. 

In another world, Megan and I might have been twins because we experience the same things and often at the same time. Last year, we were hit with a ton of bricks, but in different ways. We’re in a different place now. Our future has always been Flagpole and it always will be, but our priorities are just shifting and that’s okay because we don't get these years back. This business is a piece of you - it’s our baby, our blood, sweat and tears - but we’re implementing ways to help us detach physically and mentally from Flagpole to find that balance of running a successful business and having a healthy mental and physical lifestyle. 

JAIME’S NEW MINDSET

I’m thinking about the next guy I’m going to date and going through that dating process again. In my younger years I was like, “cool dating apps! I’ll just date and date and date because I love meeting new people.” I wasn’t serious about it, but now my time is much more important. It’s much more valuable! Amen! [high fives herself above her head] And I don’t have time for bullshit! So I’m very specific about the next partner that I’ll be with. I’m independent, maybe stubbornly independent, and the business has made me realize that I would like someone who is supportive and someone that I can lean on in crazy times and there are gonna be crazy times! I think when I was younger I thought I could get through everything and anything by myself and to a certain extent you can do that. “Me time” is so important, but maybe that “me time” can be with somebody else.

THE BIRTH OF FLAGPOLE

We were 22, sleeping in bunk beds in Brooklyn. I was in a factory when the idea came to me. I called Megan immediately and her reaction was, “Oh my God, this is really wow!”

We grew up dancing our whole life and growing up in Florida, we were the little Rugrats on the beach, running and swimming. I thought I was really cool that I could skimboard. Megan always played soccer. At the time string bikinis were the only option so we lived in them, but we were always in fear of falling out. I questioned, why couldn’t I be in a leotard and be in swim? Why wasn’t that construction out there? Why do you have to feel like you’re always falling out of your bathing suit? So when we got this idea of a leotard construction we knew that was a suit you could jump around in! It was a big ah-ha moment for us!

We slowly started working on it and got our first investment when we turned 23. Getting that first small check forced us to  write a business plan and that experience was very formative. It teaches you things you didn’t know you needed to know. The process of writing the plan is even more important than formulating the plan. If you can’t get through that, then you probably shouldn’t start a business! Even after you’re done writing it, you won’t understand how much it affects your business. Every two years, we’ll read over that first business plan. It’s funny how we are doing what we wrote back when we were so young! Back when we didn’t know what we were doing! It was like we were trying to predict the future! 

STARTING A BUSINESS IN YOUR TWENTIES

We started our business so young! You grow up quickly and in a different way. It’s probably similar to having a kid. Because we lived together, we felt like we were married! We had just birthed this thing that we now had to keep alive. We were working on it every single day and not sleeping! We were just trying to figure out how to do this thing that we didn’t know how to do. It forces you to be really nimble and you mature in a way that your peers weren’t. For us, our friends were out partying all the time. We tried to experience some of that, but we couldn’t afford to be hung over because we had to be on our toes at all times! We had everything going against us so we had to be on the edge of the next thing, anticipating every step! 

When we turned 30, for better or for worse, we felt different from our friends who had a very different experience. For all the positives that came out of having been so focused and disciplined, after having lived this way for 10 years, we’re having to teach ourselves it’s okay to live a little by allowing ourselves to chill, which is very hard to do. We live in one of the best cities and we realized that after all this time, we don’t have any memories. When the weekend came around, all we wanted to do was recharge by staying inside and watching Netflix. We would take the occasional walk around the block, but then it was like, “Okay, we’re good. We need to get back to designing!” We were so stressed and focused on the business that we didn’t live! We can’t do this again! Plus, we deserve to have memories of doing fun things in New York City!

OUR BUSINESS IN OUR THIRTIES

People say that the most beautiful thing about being 30 is you just start to not give a shit. I’m like does that world exist?! You still care but your cares change. I truly felt that there was something about turning thirty where I felt a release, like this weight off of my shoulders. You could be yourself and unapologetically do what you love. It’s taken Megan and I two years to figure out what that really means. We had accomplished so much as two girls from West Palm Beach, Florida who had no money and no celebrity to start a business. No one knew our names. Flagpole meant nothing to anybody. We weren’t a fashion house and we weren’t attached to anybody. We’re in a place where we are finally able to look back at our accolades and know that we secured funding simply because we wrote out a business plan.

SERIOUS, BUT NOT TOO SERIOUS

We launched our first collection with Barney’s and in that same season, we quickly were in every magazine and in a time where the magazine world [says out the side of her mouth “RIP magazines”] meant a lot and it felt so crazy! It just happened so quickly! We’re still these two insane human beings! Behind the scenes we’re doing celebratory dances to Justin Beiber and doing karaoke on the weekends, if we could. We launched this incredibly serious, sophisticated brand. When people would meet us, they would ask in skepticism, “You guys started this brand?!” Part of us is like, “Fuck you.” But also we get it because we’re ding dongs! We just don’t take life seriously and yet we were able to create this really high end, very sophisticated brand that made it in every major store and magazine. That helped us get taken seriously.

WE WERE OUTSIDERS

But from the very beginning we weren’t taken seriously because we were told by a man that women did not want to wear one piece swimsuits. That’s funny! Why would you know that?! Also, yes they do! In our first Barney’s meeting we were told that women don’t want to wear this! We had second guessed ourselves, “Oh, you’re right! What are we doing?!” But then after that meeting we were like, “No, women do want to wear these because we’re women and we want to wear these!” Why did we listen to them? But the currency that the opinion of the Barney’s buyer held to a brand like ours could make or break us!

We felt like such outsiders in the fashion world that we held their words with such weight. Their words don’t anymore, but in the beginning because we were such outsiders, we took everything they said.

STYLE AND IMPOSTER SYNDROME

We also didn’t fit in because we didn’t have the money where we could style ourselves in a way where we could easily fit in. Style obviously isn’t about having money. That can only get you so far. You need to adopt this personality within your style. Half my clothes were from a Goodwill in Savannah, Georgia. God bless! I found some amazing pieces! But we had imposter syndrome because we were not our customer and we felt less than our customer. We were so afraid before every meeting they were going to see right through us. But what happened was that people looked at our brand, they looked at our photos, they felt our suits and tried them on. After that it was unquestionable! People were like, we need this! They were refreshed that Megan and I were ourselves. We were funny and silly. We contained it a bit in the first couple of meetings. We weren’t full blown Jaime and Megan, but I guess we just had to test the waters, so to speak. We were scared of being ourselves because we were scared of rejection on all fronts; that people wouldn’t want to meet with us, that a store or a magazine wouldn’t take us, or a factory wouldn’t want to work with us. There were so many things that could get in our way and we felt like we had to tone ourselves down. But people loved our product because we identified so much with our product. It’s literally our blood, sweat and tears! A compliment to our suits was a compliment to us personally. It would feel like when Mario gets the mushroom and he gets bigger. You just walk with your head a tiny bit higher than before.

WE’RE NOT NEW ANYMORE

I listen to “How I Built This” and what I learned is that every business starts off like a shiny new thing, especially in fashion. But the minute you’re not new anymore, you need another story because you’re not going to get featured in the “Top 10 Best High Waisted Suits” or “Top 10 Weirdest Tan Lines” or “What is Your Swimsuit’s Sex and the City Character?” Those were all very real.

You hit a point where you hit the sophomore slump. The second time you do something, like your next album or your next collection, you have to be incredibly disciplined because the person you’re competing with is yourself and your brand. You want to make it better than the last time and we feel that we’ve been able to, but the fashion industry has changed so much since then. We weren’t new anymore. The industry was changing. We were changing. It was a weird place to be in. We had to ask ourselves, “Are we not relevant?, Are we not doing well? Or is the fashion industry not doing well?” And it’s always your inclination to be like, “Oh, it’s us! It’s something that we’re doing! We’re not enough or we’re not right!” But amidst this change, we had to step back and we decided to just do what we know and that if we do that we’ll at least get to the next step. It’s so important to detach yourselves from its identity so you can look at your business objectively. Being able to do that allowed us to care less about what the fashion industry thought, what Vogue thought, and what Nordstrom might think! The minute we stopped thinking about what others might think, we were able to direct that question to ourselves and ask how we make our business successful to us.

HAPPINESS AND SUCCESS

There’s so many things out there that tell you what happiness is, like getting your products featured in a magazine. And you experience that oxytocin release when you’re in a magazine, but when you’re not in the magazines anymore you gotta ask yourself, “Do I care? Did I really enjoy that?”

Not being in magazines anymore was the most beneficial thing that happened to us because we then turned to digital marketing. We didn’t do it at the time because we were trying to please everybody. We’re a small team and all our energy was focused on making a brand new suit, getting our suits to the stores on time, and making a sample for a magazine cover. And then we didn’t see any sales from that. But we’re on the cover of Self or the cover of Health with Brooke Shields running in our suit!?  We were literally the cream of the crop and bending over backwards to give everybody what they want, signing on to stores and taking huge percentages off and it was killing us! We thought that that is what success was and that that was how we were going to sell and yet none of it translated to sales. We had to take a step back, well, the industry kind of did it for us, but we realized that there was a whole other world that we haven’t even tapped into and that we didn’t even know the first thing about. The minute we did that, in our first year we had 300% growth from our website. 

OWNING IT

We felt controlled by everyone else. They were determining what we were doing was cool or what was going to sell. Oftentimes buyers would buy a suit and we knew in our hearts that, even though we loved the design because it’s our design, when we presented that suit it wasn’t going to sell to that customer. But we let them buy it and then it didn't sell. It happened enough times that we knew we had to put our foot down. If we don't believe in it, it’s not going to sell. But we didn’t know how we were going to make those sales happen. These stores and magazines had all the power and we suddenly started to take some of that power back. Again, we were afraid we’d wake up one day and somebody would say, “Wait, you guys don’t belong here!” But we knew that we were right! So we started telling buyers no and telling them that we weren’t going to do that discount. We learned who we are and started putting our foot down to do what was best for our business instead of what’s doing best for the other guys. That got us on a totally different track where we were assessing before we even started designing, “What is best for Flagpole? What is the Flagpole woman?” as opposed to what Net-a-Porter and the magazines going to like. At the end of the day, you can’t blame somebody else for your lack of sales. It’s your business and you have to take responsibility because those stores aren’t taking the responsibility. 

It’s wild being on the other side of that because we look back and we can see that the grass isn't greener over there. The digital market and the online world has infinite possibilities! 

So in not a nutshell, that’s how we’re doing!

We’re ever changing and we’re learning every single day. That’s probably why we’re still in this and still going strong. You learn every single day about yourself, about how to run a business successfully or unsuccessfully. The most valuable thing is to be able to be humble and take responsibility when something doesn’t work. But you have to be willing to test things and take risks.

Shop Flagpole NYC Final Sale with Styles up to 80% off. I do not earn commissions off of sales. I just really love Flagpole and I’m heartbroken to see them go! All the love and support to Jaime and Megan! xoxo The Riza