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Startup Lessons From the Youngest Girl in the Room

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Whether you’re 15 or 50, you can learn a thing or two from the 20-something entrepreneur behind 99dresses.

By Lorraine Sanders (Contributing Writer, Women 2.0)

Australian-born entrepreneur Nikki Durkin has founded a startup, moved to the U.S., relaunched her company from Silicon Valley’s Y Combinator, watched it become a fast favorite among tech cognoscenti such as Robert Scoble and Ben Parr and decided to pivot once again to turn 99dresses into a mobile-only platform headquartered in New York and set to debut its new iOS app any day now.

P.S., she’s 22.

What’s in a Number?

While it’s true that age is just a number, it can easily become a factor for startup founders – even if you’re in an industry that’s more comfortable than most with youthful faces behind the wheels of companies.

“When I did the whole fundraising thing, I was 20, it was in Silicon Valley. Yeah, it was intimidating dealing with people that are two times your age,” Durkin says when I ask about her experience being the youngest one in the room.

It wasn’t always a comfortable spot for Durkin, who created the first incarnation of her clothes swapping ecommerce site 99dresses while still a teenager, but she is quick to point out that being different – far younger, in her case – than the majority of the people she encountered in the business landscape has its benefits and advantages.

Tough Experiences Make You Stronger

“It was intimidating, but it was also a really good learning experience to do that and face your fears. The way I think about a lot of stuff is, ‘Okay, I am going to get through this,’ learn from it and the next time I do it…I’ll come out of it and be like, ‘That wasn’t so bad,’” she says.

For Durkin, facing investors with skepticism about her age and experience not only helped her develop a thicker skin, but also resulted in weeding out people that probably wouldn’t have been a good fit in the long run.

Durkin recalls, “One VC firm brought up, ‘Hey you’re like 20,’ and the age thing was obviously an issue for them, and I didn’t feel like we would have been a fit working with each other.”

In many ways, the discomfort with Durkin’s age highlighted an underlying difference in philosophy.

“Some people view [working with someone young] as an opportunity, whereas some investors saw it as, ‘She’s young and not experienced,’” says Durkin.

Mentorship Perks

There are plenty of ways being young can actually make the path to launch easier, and not just because you can pull all-nighters.

“I always found that because I was young, I could get a lot more help. People are like, ‘You’re a young entrepreneur. I’ll help you,’ because they’re like, ‘That was me when I was starting out,’” she says.

Along with support from Y Combinator and current investors such as Tim Draper, Durkin has also tapped into a network of female startup entrepreneurs in her current hometown of New York. They have dinner regularly to discuss their various ventures.

Getting it Right Takes Time

Even with plenty of help, Durkin quickly acknowledges that she’s yet to get her company exactly right. She hopes to close in on that goal with the soon-to-launch mobile update on her original idea. When it relaunches as an iPhone app, 99dresses will allow users to upload images of clothing they’d like to post to the platform and immediately receive “buttons,” the platform’s virtual currency, in an amount calculated by an algorithm that assesses item value to the community. Users can then use those buttons to obtain items of clothing they want. Not having to wait for an item to sell is an aspect of the shopping experience Durkin hopes shoppers will appreciate.

“One of the big changes with this is instant gratification. You don’t have to wait five days for it to sell,” she says.

In theory, this change also stands to combat the user drop-off that can occur on resale marketplaces when users upload many items, sell only a fraction of what they’ve posted, get discouraged and fail to post more items or visit the site regularly.

Another key change is the addition of “karma,” a Klout-like well of points that ebbs and flows as users post new items to the site, engage on the platform and exchange buttons for new items. The more valuable the item uploaded for swapping happens to be, the higher the karma payout. The more engaged a user is and the better her contribution to the community is, in general, the higher her karma will be.

Why institute karma? It’s intimately tied to another new feature, which essentially turns the first 24 hours any item is on the site into a holding period, during which any user can register her interest in claiming it. When the 24 hours are up, the item goes to the girl with the highest karma. A user can increase their karma score by listing higher quality items and receiving positive feedback on a trade. If no one claims the item before the time runs out, the timer will automatically reset for an additional 24 hours.

“What we’re trying to do is recreate a physical clothes swap party,” Durkin says.

In much the same way that friends at physical swap parties might award an item to the girl who wears it best or wants it more than anyone else, karma brings an added twist to the mobile experience that aims to keep the community engaged and reward its most valuable members.

Says Durkin, “It’s a mechanism that comes into play to make sure that the people that are giving the best stuff are getting the best stuff.”

Don’t Hide Your Best Ideas

Speaking of building karma, Durkin also echoes the idea as she talks about her company’s earliest days and yet another lesson learned along the way.

“By being really open about your ideas, you get so much more benefit than worrying about people stealing your ideas,” she says.

While more than a few new and seasoned entrepreneurs are wary of talking openly about their ideas and plans, Durkin credits her decision to talk about 99dresses on social media as one of the lynchpins of her success. In a short time, she reached thousands of people and knew she had a viable concept.

Says Durkin: “If I’d been very closed and not shared my idea [on Facebook], I don’t think my company would have gotten off the ground.”

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lorraine-headshotAbout the blogger: Lorraine Sanders is a journalist, blogger and media consultant. She is the author of the San Francisco Chronicle Style Bytes column and writes regularly for FastCompany.com and others. She is founder of the blog Digital Style Digest and an inhabitant of the San Francisco Writers Grotto. Connect with her on Twitter @digitalstyledig or @lorrainesanders.