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How Pose's Co-Founder Went From Broke Freelance Journalist to Tech Entrepreneur

"Be curious, know more than one thing, and don’t be afraid of change." When Alisa Gould-Simon offers career advice, you sit up and listen. Co-fou

"Be curious, know more than one thing, and don’t be afraid of change." When Alisa Gould-Simon offers career advice, you sit up and listen. Co-founder and VP of Creative and Partnerships at Pose, a leading online fashion platform counting two million users and Rachel Zoe as an investor, Gould-Simon has that rare mix of self-assuredness and approachability that you’d expect from a contributor to Good Morning America and the New York Times (yep, she's done both). At Pose, Gould-Simon creates pilot programs with brands (like Coach, Intermix and eBay), pitches her company to venture capitalists (over $4 million has been raised to date), and helps decide what blow-your-mind new features to roll out next. It’s a pretty plum job in one of the highest growth industries out there: technology startups. But just three short years ago, Gould-Simon's day-to-day was anything but plush. Graduating from NYU with a journalism degree, she had proceeded to head into one of the toughest industries--publishing--during what would soon become one of the toughest economies in memory. “I spent six months really freaking out.” It was 2009 and publishers went from paying $1 per word to $25 per post. “It was just shocking and you couldn’t make a living off of it.” Looking at what happened next, you see Gould-Simon’s own career advice at play: “See where there is opportunity, and then ask for the chance to do it. I’ve tried to take that approach with everything I’ve done.” In a few short months, Gould-Simon had relocated to L.A. (“I felt like if I stayed in New York any longer I wouldn’t know how to live anywhere else”), had a fortuitous meeting with her now co-founder Dustin Rosen, and took a chance jumping on board to help launch Pose. It’s a series of decisions that suggests both serious initiative and killer instincts. And yeah, it paid off. Defining what drew her away from fashion to the world of technology startups, which she sees as “a bubble that will never burst,” Gould-Simon offers, “You’re constantly moving with the changes in the industry so you’re never done, and I find that really exciting.” They're (heeled) footsteps she hopes more will follow, describing a “big need” for women (and men) from the fashion industry to make their mark within the tech startup community. I caught up with Gould-Simon near Pose’s Santa Monica headquarters to talk breaking the fashion-tech divide. You began as a journalist and are now a pioneer of high-fashion tech. How did you get your start in the fashion industry? When I was a sophomore at NYU I got a job as a shopgirl at Unis in NoLita. I am now friends with the designer, Eunice Lee. That job helped me get accustomed to what was happening culturally in New York then, it helped me become more versed in global brands, and it helped me really understand design and manufacturing. At the time I graduated I had been interning at a new media startup focused on cultural coverage. I was really fortunate to have Karin Nelson, now the features editor at W, as my editor. I very quickly became accustomed to the community and what was happening in music, fashion, film and art in New York. Because it was such a small operation I was able to have a lot of freedom and do the interviews I wanted to do, and so many of them happened to be in fashion. So I focused on fashion somewhat subconsciously and grew a network there, and when I started freelancing a lot of assignments were organically in fashion. What about the fashion community pulled you in back then? When I started to interview people and get to know the characters in all these different industries, I was consistently impressed with how smart and well-educated the people that are influential in fashion are. People often discount fashion as being materialistic and superfluous, but when you get to know the top editors and designers you realize they have phenomenal instincts, phenomenal educations and are incredibly charming and interesting. That made me fall in love with the industry. How did you approach fashion journalism? I took great lengths to write about trends on the business side or profile interesting people in the industry, instead of just fluff pieces. I focused a lot of my life as a journalist on how I could put myself in a position to learn from these people that I so admire, and understand their story and how they got here. It sounds like you gave yourself a lot of creative freedom rather than following editorial assignments, per se. [Laughs] You make it sound way cooler than what I had in my mind at the time. You can get kind of pushed into a box, and I think honestly that’s why I was never on staff anywhere and why I didn’t make any money. As a freelancer it’s really hard, and eventually that’s why I had to leave the business. But I loved the freedom and being able to say, ‘These are the ten stories that I want to write, and I just need to find the places that will publish them.’

So how did the jump to tech come about? I kind of annoyed the crap out of my boyfriend for six months crying about how I couldn’t make any money. It was 2009 and major publishers went from paying $1 per word to $25 per post. The change was shocking and you couldn’t make a living off of it. So I thought about what my strengths were. I thought about going back to school. I considered everything. I realized that because I had come up in a digital space, I really understood the packaging and distribution of online content. So I decided I was going to start a consulting firm. I called it The Rackit, I had a friend create the logo and I bought the domain. And just as I was getting it up and running I met my now co-founder. Four weeks later I was on board at Pose, and two months after that we had our beta out in the marketplace. That sounds like a circuitous path. How did you make those decisions? I wouldn’t have articulated it this way back then, but I could feel that there was a momentum in technology and startups. To be happy and satiated I need to constantly be learning new things, and maybe even exposing myself to things that are scary because they’re unknown. Technology and startups felt like that. After being in fashion so long, being the only woman in the room was new and interesting, and to this day no one on our team has a background in fashion. It was exciting to have very clear value add, as opposed to being in an industry where there are a number of people who know what I know and can do what I do. Going from fashion journalism to a tech startup must have been a big adjustment. How did your skill set have to evolve? I was really being hired for my storytelling skills, and I didn’t realize how important that would be beyond creating editorial and press materials. Storytelling is integral to heading up advertising and sales, to pitching your company to a venture capitalist fund, and to branding your company so your users identify with a vision. When I started, my role was focused on PR and communications. But to the true credit of my co-founder, at many instances I’ve said ‘I think I can do this, I want these responsibilities’ and he’s never been reluctant to give me those. Heading up an advertising department is not something I’ve done before, but through sheer determination I can figure it out and build one. I’ve tried to take that approach with everything I’ve done--seeing where there is opportunity, and then asking for the chance to do it. And so once you’re given that chance, how do you succeed? It’s always finding the right people. I think of the phrase ‘hire for your weaknesses’. There’s no way you can know everything. I am happy to admit what I don’t know, and I think once you can do that you can find the people who do have that knowledge. How do you manage someone who knows more than you? You have to be confident in what you know, and then you can admit to what you don’t know. You need to be able to hear them out and not feel insecure learning from them or suggesting your own ideas. We are a collaborative company, and sometimes the best ideas do come from people who are seeing things from a different lens--product ideas from an engineer, or marketing ideas from a designer… Not being the smartest person in the room can actually be a real asset if it leads to not focusing on just what you already know. You’ve gone from being a fashion person in the fashion space to being a fashion person in the tech space. How has that changed how you look at the industry? Looking at the fashion industry from a tech perspective inevitably puts you a little on the outside. But I also think that the majority of consumers feel like they’re on the outside of the fashion industry. Fashion is insular--it’s an incredible beast that can perpetuate huge cultural shifts, but at the same time it can be very alienating. Understanding how to talk about fashion in a way that makes it accessible to tech people ties into building a product that is not just for fashion insiders, but can be approachable for any woman who likes to shop. So your job sounds pretty amazing. Tell us about some of the challenges you face. There is never enough time in the day. We are a startup and try to live lean, so prioritizing is really tough because everything feels like it needs your attention. My co-founder and I talk a lot about what our respective top three or top five goals are right now. If anything falls below a ‘five’, we put it aside. That’s really important for both not burning out and staying as focused as possible. Often our biggest challenge is ensuring our employees are happy and not overworked. Everyone is keeping stride with a stressful, fast-paced industry, but we want our team to still feel motivated and satisfied. Startups are notoriously collaborative and nimble. Do you think those principles apply to traditional fashion companies, as well? Yes, I think they need it. If you’re only focused on your industry and only focused on solving the same problems, you’re will lose out on potential ways to innovate or approach things from a new angle. Startups are often lean and don’t have the resources to buy users or buy press, so we have to really think outside of the box and carefully consider return and value. You said you’re often the only fashion person in the room. Is there opportunity for more fashion people to get involved in tech startups? There’s a huge opportunity. I hear so often of tech startups that are focused on the fashion space, and much to my dismay don’t have anyone from the fashion industry involved, or don’t even have any women on the team. There is a big need for women from the fashion industry to get in the room and become part of the conversation. What advice would you give to recent graduates who want to do what you do? You have to be endlessly curious. If you are curious you will inevitably find things that excite you, and that helps lead you. You also have to know linear growth doesn’t exist anymore. Starting as an assistant doesn’t necessarily mean you’ll be promoted to senior director. You also have to cross-pollinate your education and not know just one thing. One of our interns is majoring in linguistics but also minoring in computer science and business. Candidates like that have a much easier time finding high-growth opportunities because they have multiple skill sets and are adaptive. The reality of working with any startup is that you are going to do four different jobs at once… and maybe six [laughs]. You have to be really confident but also open to learning new things and applying different sets of skills. For a fashion person interested in getting into the tech startup space, where should someone start? Read TechCrunch and GigaOm. If you see a company that you think is doing something really interesting, get involved and reach out. If a company is doing well they may be in a position to hire even if the job posting is not out there. You’ve done work on the journalism side, brand side and tech side. What else do you want to accomplish in your career? I really want to learn how to code. From everything I’ve understood, it’s a different way of thinking and that is where we as people are moving. At Pose we dream up crazy features and our engineers are like, ‘Okay, we’ll go build that.’ I want to understand how that happens. And I want to become a better gardener. Any final words of wisdom for people trying to make it? (1) Hang in there. It’s a scary market right now, and that’s how I felt when I was freelancing and being paid $25 for something that took hours of my time.

(2) Be a little cutthroat. Don’t get sidetracked with opportunities that may sound good but not provide a lot of value.

(3) Don’t be afraid of change. So often it’s the change and the uncomfortable parts of life that will be the most rewarding.

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Melanie Bender is a brand and marketing consultant who has created approaches with Sephora, Topshop, Louis Vuitton and W Hotels, and is a co-founding partner of innovation and communication firm Post+Beam. Find her on Twitter at @melliebe.