Meet 9 Young Entrepreneurs Who Risked Everything — & Won

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We get it. You want to do your own thing. Start a business. Be your own boss. But, while it’s easy to complain about your current secure-but-not-so-satisfying position and ramble fantastically about an ingenious invention or innovative business idea you have, one daunting question always remains: Where would you actually start?

In our latest installment of Beauty Nation's The New Provocateurs, we teamed up with Revlon to track down nine brilliant young entrepreneurs who once arrived at that same crossroads and asked them how they found the courage to make the leap. Below, they talk openly and honestly about going into debt, getting fired, and becoming power players in brand-new fields. Their stories are equal parts empowering and unnerving — but that seems to be the guiding principle when it comes to successful entrepreneurship.

And, these sharp, fearless women have made it work. They share how they keep it all together, from defining a work-life balance to perfecting their executive-level beauty moves. So, grab a memo pad and put on your thinking cap. It’s time to draft that business plan.

The Tell-All Art Director: Jessica Walsh

PHOTOGRAPHED BY GEORDY PEARSON.
If you’re well-versed in the design world, you’re probably familiar with Jessica Walsh, co-founder of the two-year-old design firm, Sagmeister & Walsh. The NYC-based company is most notably known for a set of graphic, body-painting ads for a luxury department store in the Middle East, in which Walsh splayed typographic images and inspirational messages all over people’s faces and bodies — ads that were printed in newspapers, in magazines, and on billboards throughout Lebanon. In fact, Walsh even went nude herself with her partner Stefan Sagmeister (who was also in his birthday suit) on announcement cards when they launched their firm in 2012.
But, for the non-acquainted, just a little casual Googling will tell you that Walsh was the infamous love interest (of sorts) in the viral 2013 online social experiment 40 Days of Dating. In it, Walsh dated one of her best platonic guy friends, Timothy Goodman, for 40 days. It was a real life, will-they-won’t-they journey that was equal parts hilarious, heartbreaking, and incredibly vulnerable. It’s clear this designer isn’t scared to put her body, her personal life, and, above all, her designs out there. Below, Walsh bares the secrets to her success.
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On being a young entrepreneur
“I think people were surprised by my age when I first partnered with Stefan Sagmeister, [my former boss]. I was 25, and that was a little shocking for some people, with Stefan being 50. But, we just do what we do. I’m confident and passionate about the work I’m doing, and eventually people see that and get over [my age].”
Don’t be afraid to be vulnerable
“Last year, I did a project called 40 Days of Dating, which was a social experiment and design project where I dated one of my best friends for 40 days. We had totally opposite issues in love, and we wanted to see if we could maybe help each other out, meet in the middle, or end up dating. We posted it online, and the response was incredible. It was the responses that people sent in — sharing how much it helped them to hear these raw honest feelings — that made me realize I want to bring more of the personal aspect, the human element, into my work. I’m going to be doing more of that in the future: combining design with personal stories.”
Get personal with your audience
“It was important that we were completely open about all of our issues and all of our shit. We even talked about when we had sex [for 40 Days of Dating]. Very, very personal stuff. But, seeing how well people responded to that stuff, people don’t want you to be perfect. I think that’s been really helpful.”
The key to staying creative
“What I do isn’t pegged to one thing: I’m a designer, an illustrator, an art director, but I get to work in so many different fields. Right now, I’m collaborating on a fashion line with my friend Valentina. I’m doing a line of sunglasses. I want to keep doing lots of new things within the creative world. I definitely don’t want to be attached to one thing. I want to keep expanding and learning.”
Where I find inspiration
“The trick for me is not to look within design. You can go on design blogs and see what’s going on all around the world instantly, which can be great, but a lot of people start regurgitating the same exact styles and ideas, over and over. So, when I’m looking for inspiration, I try to look completely outside of my own field. I’m inspired by furniture, fashion, astronomy, and psychology books — I pull from all of these things.”
Create the team you want
“I see more and more successful young female designers, but when you look at the landscape of older successful designers, it is male dominated. I haven’t experienced any challenges personally, luckily enough. I think within larger advertising companies, where there’s more of a hierarchy, you would start to see some of those issues. But, I have a small team; we all love and respect each other, and I don’t really face that.”
Sophia Webster heels, Chromat pants, Norma Kamali top, And Other Stories bracelet, model's own rings.
Photographed by Geordy Pearson; Makeup by Sophie Haig; Hair by Michiko; Styled by Laura Pritchard.