Meet Our Newest Girlboss Grant Winner: Dressmate

Meet Our Newest Girlboss Grant Winner: Dressmate

Jennifer Simons’ startup idea came to her over a slice of pizza. At the time, she was 19 years old and pursuing a pre-med track at Georgetown University. But when the classes she was taking started painting a different reality than the childhood dreams she’d held for so long, she found herself back at square one trying to figure out what she wanted to pursue next.

But inspiration can strike anywhere, and over dinner with a friend she exchanged clothes with often, she had a lightbulb moment. She loved her friend’s wardrobe, but they were entirely different sizes (Simons is 5’11 and her friend is 5’2). She wondered what it would be like if they could shop the closets of girls on campus who were actually their size. That night, she set out to build a marketplace for women to rent out clothes to each other.

Simons said, “Every student, and by extension, every woman, has a closet filled with clothes. The possibility of tapping into 1,000 closets within a 1-mile radius and a fraction of the retail price was enticing enough that I dropped being pre-med to pursue this venture.”

“You have to be the biggest champion for yourself before anyone else is.”

It was a scrappy start that began with a Facebook group and a Venmo account, but Dressmate quickly found traction as a solution for frugal college students who enjoyed being able to try out something new without the hefty price tag that comes along with a new purchase. The only drawback? Dressmate was oversaturated with fast-fashion options that didn’t reflect one of Simons’ core values: sustainability.

Over time, the idea of community that Dressmate was built upon helped Simons refine her business idea to span beyond the peer-to-peer marketplace she first introduced several years ago. Now, at 22 years old , Simons is relaunching Dressmate as an e-commerce platform and Brooklyn-based retail concept that celebrates women-led, independent, and sustainable fashion designers (with a little help from the Girlboss Grant, of course).

As she gears up for her site relaunch on May 31, Simons spoke to us about what it’s like to pitch in front of investors, how to build a team when you have no management experience, and her long-term goals for Dressmate.

What have been some of the biggest challenges in getting Dressmate up and running?

“The hardest thing was eventually deciding that I was ready to be full-time with Dressmate. I don’t think anyone is ever ready when they first start, but also if don’t take the leap you’re never going to be ready. There’s such a risk putting yourself out there.”

“Fundraising is also really hard. I bombed at so many pitch competitions—like, truly embarrassed myself. You need to be a little crazy to want to start something on your own because essentially you’re looking at the competition—which exists in every industry no matter what you’re doing—and saying, ‘I think I can do it better.’”

How many times have you pitched Dressmate?

“Upwards of 70. I’ve heard a lot of ‘no’ and a lot of ‘maybe, we’ll see.’ You just never have any idea what you’re getting yourself into until you’re at the meeting. You always do research on the investors before you go meet with them because you want to know what industry they invest in, what stage they invest in, and historically what they are personally interested in. You go in with a set expectation, but you really have no idea until you’re there and hear the questions they ask you. It’s both emotionally and physically exhausting hearing no so times.”

What’s some advice you’d give others looking to get in front of investors?

“Do it as soon as possible. I think people have this idea that you can’t go to an investor until you have this picture-perfect model and business plan. But I think it’s from talking to investors and being told no a certain number of times that you realize if 30 people tell you no and they’re the best in their business, there must be something that you’re missing. So maybe there’s something you could change to turn the no into a yes.”

“Also, the most important thing is to always ask for something else in the meeting. It may hurt when someone who is successful or knows what they’re doing says, ‘Oh I’m not really interested,’ but they’re not saying no to you as a person. You can always ask them for something else like, ‘Can I talk to some of your portfolio companies that are also in the fashion industry?’ Act like it doesn’t matter whether they gave you a yes or a no. Interview them and see what they can do for you. You have to be the biggest champion for yourself before anyone else is.”

“Bottomline, don’t keep your idea to yourself. Tell as many people as possible and try to get as much feedback and advice as you can.”

Why is sustainability so important to you?

“When Dressmate first launched, I got a lot of feedback about the clothing on the platform. It was mostly fast-fashion that wasn’t making a huge difference in girls’ wardrobes. I really cared about aspirational, sustainable brands, and so did a lot of our community. People would send emails asking what the best sustainable brands to shop from are, even if we didn’t have them rentable on our site. That’s when I decided I wanted to make sure we were supporting those types of brands. Essentially, we want to feature smaller brands that the larger population might not know about. We already have partnerships with Paloma Wool, Samantha PleetAbout Arianne, Reike Nen, Nicole Saldana, Susan Alexandra, and more.”

Now that you’ve been able to build a small Dressmate team, how have you handled being a manager for the first time?

“We have about 12 part-time members on board. I don’t think I’m a traditional manager. And I haven’t had a lot of corporate experience, to be frank. I’ve volunteered at a pediatric unit, I was a camp counselor, a babysitter, a tutor, a mentor, a teacher’s assistant, etc. So I adopted a lot of those same principles and tried to hire people who know more than I do about whatever their role entails.

“My management style is friendly and very hands-off, and I think it’d be unnatural for me to adopt a super serious managerial position. Because look, I am absolutely younger than the people who I hire and I’m also here to learn. So I try to be very straightforward and honest about what I’m looking for. And I’m very clear on deadlines. From there, I just let them do their jobs and it usually turns out great. If it doesn’t, I’ll fire quickly and move on.”

How will you be using the Girlboss Foundation grant?

“We were able to hire a creative agency to redo our branding, which has been really exciting. And we’re going to renovate the inside of our retail space, which will be a fun undertaking but will cost us upfront.”

What are your biggest hopes and plans for Dressmate in 2019 and beyond?

“I’m excited to launch our store in Greenpoint this fall, and for our site relaunch. I want people to feel joy when they see Dressmate and buy something. In this world of [trending] minimalism, people forget that fashion is supposed to be fun and make you happy, and it’s okay to indulge and get the hair clip or the sweater that will make your week brighter. I’d love Dressmate to be that for people.”

“In the next five years I want to build a community of people who really want to support the designers we’re working with. And not just the designers, but the people that the designers are employing to manufacture and create the clothing and source the materials ethically and sustainably.”

“I still have the same goal for Dressmate that I had when I first started: that everybody has a closet filled with things they love and adore.”