Career Advice From Hukkster: 'Never Wear a Black Suit'

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Between e-commerce, blogs, apps, and the vast world of social media, fashion is as much about technology these days as it is about style. In a new series, we sit down with some of the many women who are killing it in the fashion-tech industry and find out how they're kicking ass in their careers. Their worst mistakes, their best advice... it's all here. This is Ladies Who Launch.

When Erica Bell and Katie Finnegan launched their online sale-shopping tool Hukkster last October, the juiciest part of the story was that the millionaire Winklevoss twins (who came to fame as the Winklevii in the Facebook movie), were investors.

But Hukkster has emerged from the Winklevoss' shadow and come into its own. Time Inc. named it one of 10 New York-based startups to watch this year, and constant updates—influencer-curated content called Tastemaker Hukks launched this week, and a mobile relaunch is scheduled for September—are helping the site evolve quickly as it gains traction with users. We talked to Erica and Katie about the chumminess of Silicon Valley, cleavage in the board room, and risking your personal savings on a business idea.

Racked: You guys were both merchandisers at J.Crew before leaving to launch Hukkster. How did that help you in the startup world?
Erica: In merchandising, you really have to wear both both creative and analytical hats. You talk to the designers, plan out the assortment, identify what's trending and what styles you are going to watch on the creative side. On the flip side, you work with your planner and your production team, deconstruct cost components, and actually try to build a profitable business. We couldn't have planned to have that experience and then go on to launching our own company, but now, looking back, that has come in handy.

Racked: What made you decide to leave a corporate job to start your own company?
Katie: We were just so passionate about this idea that we didn't necessarily do a full risk assessment. Which is probably better.

Erica: We had also seen the end results of launching a new idea when we were at J.Crew, which added to the excitement. We saw Crewcuts and Madewell launch, which were two very successful, cool brands. So I think we saw the benefit and the sense of satisfaction in that process.

Racked: Did you have mentors as you took the leap?
Katie: We really did reach out to anyone and everyone that we had seen jump from a corporate role into a startup. We were nervous, because you feel like you need to keep your idea protected and that you can't go out to world with it before you have built it. But we learned very early on that you have to put yourself out there and tell everyone and anyone that will listen. From that we have learned a lot of best practices. The entrepreneurs we talked to were willing to share their mistakes, so that when we launched we had some perspective on how to approach certain scenarios.

Erica: I would say to anyone that is looking to starting a company, don't be afraid to reach out. You will be shocked at the response you get. The startup scene is very exciting right now, and anyone that we had a remote, eighth-degree connection to was willing to have coffee with us. Had we be gun shy and not asked for help, we wouldn't have gotten it.

Racked: You guys used your own money to fund the business, which sounds terrifying. How did you have the courage to risk your personal savings?
Katie: Had someone sat me down six months before launch and said, 'Katie, you are going to spend this much,' I don't think I would have agreed to that big of a check. It was little by little, like, 'Lets do this little cost and see what happens,' and then that was well received. We saw the traction. And once we saw success, we added the next milestone. I think that is very important early on before we throw it all up in the air.

Erica: I think that is such a valuable lesson for anyone that wants to be an entrepreneur. You can't say, 'OK, these are all of the milestones I need to hit this year, and this is how much its going to cost me.' We had to set priorities week by week. Breaking it down into those pieces made it a lot more manageable.

Racked: You've managed to secure some impressive investments at this point, including from Winklevoss Capital, aka the venture capital fund run by the Winklevoss twins of Facebook fame. How do you explain fashion to investors and other business partners outside the fashion industry?
Erica: You really have to remember that retail and fashion is a multibillion dollar industry, and that you're the expert. If you are female, and if you love fashion, and if you are an expert in this industry, you have powerful insights and expertise. Have confidence in that, although you might not be what a traditional entrepreneur looked like five years ago, or what an entrepreneur in Silicon Valley looks like today. There are a lot of people that will really look at you as a great investment.

Racked: As women who are selling a fashion product outside of the fashion industry, how do you present yourselves in meetings? Do you show off your fashion chops, or do you tone it down and wear a black suit?
Katie: First and foremost, we never wear a black suit. But there is a level of sophistication, of wanting to be taken seriously—especially as a female entrepreneur. So revealing clothing is a no, but a great pair of bright pink pumps? Absolutely.

Racked: How do you pick a partner to launch a business with?
Katie: We had worked together in a professional environment for five to six years at J.Crew by the time we decided to launch a business together, so we already knew each other's pressure points. You really need to make sure the person you choose to partner with on a business is not just someone you go to brunch with or have a beer with. You might get along really well with that person, but its different at a personal level. If you have not been fortunate enough to work together, I would suggest doing things like training for a marathon—really seeing difficult situations, because that is what a startup is. It's like a marathon everyday.

Racked: How do you deal with work fights? Do you have advice on smoothing it over when it gets bumpy?
Erica: Something that we are learning is that you can't just ignore those situations. If something happens and you feel frustrated with the other person, or if your opinion isn't being heard, you have to bring it up. You can't keep it inside. It's hard because you don't necessarily want to take a step out of that situation at the moment and say, 'Let's talk through this dialog," but, like any relationship, you really have to open those lines of communication. Not all the conversations are fuzzy and friendly and rainbows.

Katie: You have to be committed. It's a lot easier to be like, 'That's annoying, but I'm going to let it go." But in retrospect, it's better to talk it out. If I just let it roll off my shoulder, but then two weeks later something similar is going to happen and then I am going to blow up. It's kind of like a marriage; you are committed to making it work. You took these vows together that we are going to get through this.

Racked: What's the biggest mistake you've made in your career?
Katie: I swam in college, so I had this mentality that the harder I worked, the better I would be, and I would get promoted and all that. Early in my career I had one boss who was not ready to promote me. I went to her and explained that I was working so late every night, and I didn't understand why I wasn't getting promoted. 'But that's the whole point,' she said. 'If you are working so late on this job, how can you take on more responsibility?' At first I was so taken aback, but it's so true. My mentality originally was the later I worked, the better. But I really should have worked smarter, and that's way more well received. I had to show that I have this under control. [Ed note: For anyone interested, Katie recommends this Harvard Business Review article on how to work more efficiently.]

Racked: What are the pros of working at a scrappy start-up?
Katie: Especially in New York right now, the tech scene is so exciting. I feel like working in tech is such a cool opportunity for people that don't really know where they are going or what their passion is but want to get their foot in the door. A startup is the place where you can go and get 15 different types of experience, even as a very junior person in an organization. You can try out marketing, you can try out social media, you can try out analytics, and then kind of figure it out. We always joke that we wish we had this opportunity when we were right out of school, because it's kind of like a crash course on what business is all about.

Racked: What advice would you give to anyone who wants to follow in your footsteps?
Katie: You do not have to have an end goal on the first day. So often people think "If I'm going to do this, I need to know where I'm going to get, how much I'm going to make, etc." If you do what you love, it will figure itself out. Or at least you will be very happy. That's also really important.

This interview has been edited for length and clarity.

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