As all women know and can relate, getting dressed in the morning is never as easy as we wish it could be. To the women who feel confident in tossing on whatever they please regardless of how it will match or how it will look – power to ya – but if you’re like me, then your morning routine can be a little bit more complex. One minute you want a pullover sweater, but the next minute you’re eyeing that cardigan that you haven’t touched in months. If you’re in Seattle, you’ll start off your morning bright and sunny and by afternoon caught in a torrential downpour. Making sure your outfits are appropriate for the weather can be one of life’s unexpected challenges… so what if there were something to make your life and choosing outfits a little bit easier? Former fashion editor at Lucky Magazine and MBA grad turned entrepreneur Kendall Herbst created a solution. StyleUp was designed to simplify your morning routine by sending you personal recommendations on an outfit to wear to match the weather of your location daily. I have been receiving emails from StyleUp for the last year and have loved the daily inspiration regardless of whether or not I’m re-creating the outfit myself that day. Since Kendall has had such a diverse background in working in the real world to going back to school to creating her own start-up, I thought that she would be a great woman to feature on Yow Yow’s “Women Who Are Making It” series.
Q: You’ve done so much with your career already. Can you give us an entire back story on your career path and how you go to where you are today?
Kendall: Thanks! Out of college, my first job was at New York magazine, helping them build out their online fashion presence. Then I moved over to Lucky magazine as the Fashion News Editor. I wrote two sections of the magazine and covered all the up-and-coming designers, major news and rising trends. I also did stints at InStyle magazine, J.Crew and Ann Taylor LOFT. After about five years of that life, I got really inspired by the Gilt Groupe women and decided to go to business school. At MIT Sloan, I got my idea for StyleUp and participated in Y Combinator earlier this year. My life has changed drastically from a few years ago — less fashion shows and more time talking to engineers — but I absolutely love it.
Q: In November of 2012, I had read a story on Fashionista.com that you left the fashion writing industry behind to pursue your MBA at MIT Sloan. What motivated you to make this huge decision?
Kendall: Fashion was changing so quickly with the rise of blogs and new ecommerce models, (see the mobile eCommerce statistics for an idea). Because clothes were being sold in a different way, they were therefore also being designed and marketed differently and things like SEO for these ecommerce models became very important. I won’t go into that in too much detail, but you can visit https://victoriousseo.com/verticals/ecommerce-seo/ to find out more. It just all seemed very different. I admired all these women launching amazing businesses. Meanwhile, I had become a bit too comfortable, even complacent in my job as a fashion editor. I decided I wanted to stretch myself and saw business school as a great new adventure. Business school is the start of something rewarding for people who have that drive and determination to be in this sector. If you are contemplating it, you can get more info from websites such as fortunaadmissions.com to see how you can get in.
Q: What was the transition like leaving the working world and going back into school again?
Kendall: It was certainly a bit strange at first — buying notebooks and taking midterms felt like a lifetime ago. Also being an intern the summer between your first and second years was a little odd as a 27-year-old. All that said, it was a really refreshing change of pace and a terrific environment to try out new ideas and work on my weaknesses in such a low-risk classroom situation.
Q: At what point was StyleUp born and where did you find the inspiration for this idea?
Kendall: In many ways, my whole life has been leading to StyleUp. From spending way too much time in shopping malls when I was young, to working as a fashion editor, to going to business school — I’ve talked to a lot of women in my life about how fashion makes them feel. I started playing around with the idea in the late winter 2012, realizing that the market was missing a platform for really actionable fashion advice — what should I wear tomorrow? I wanted to create something that just made the process a little easier for busy, modern women. StyleUp doesn’t tell you everything, but it offers personalized inspiration to make the daily process not just easier but a lot more fun.
Q: What does a typical day look like for you?
Kendall: Like many people, there are no typical days but I do have one routine that I try to maintain: going for a jog along the river in the morning to clear my head. Then, I check in with my team to make sure no one has any roadblocks ahead of them. I’ll look over the daily metrics. I’ll meet with brand executives. I’ll chat with our members to get their feedback — one of my favorite parts! I’ll handle the company finances and budget — one of my least favorite parts! On any given day, I touch about every aspect of the business. Lately, a lot of my time has been spent on creating StyleUp shopping which launches soon. Stay tuned for that!
Q: I noticed that your team consists of you and your co-founder, but is your team much larger now?
Kendall: We’ve brought on a designer and another developer and some college interns. Overall, I love working in a small team and I like handling many different roles. I look for people who like that dynamic experience as well. We’re quite lean and scrappy, and I never want to lose that.
Q: I’ve been receiving StyleUp daily emails for quite some time, but I am curious, what is your process for selecting an outfit for the day for the correct region depending on the weather? How far in advance are you finding these daily outfits and where are your usual sources because sometimes they come straight from street style or from celebrities?
Kendall: All of our images are tagged by a series of fashion and weather properties, and our system sorts them based on each member’s weather forecast and style preferences. We work on a day-by-day basis so we can provide the most accurate weather for every StyleUpper. I’ve learned our women love variety and see StyleUp as this fun surprise Monday-Friday, so I aim to show a great mix of inspiration images.
Q: Has StyleUp been able to collaborate with anyone yet and if so what is a collaboration that you are most proud of?
Kendall: We’re starting down the road now — stay tuned!
Q: As we all know, the road to building a startup is both rewarding and challenging. What are some challenges or obstacles that you have faced on the way to creating StyleUp?
Kendall: There are many. A major one is my lack of experience. As a first-time founder, I’ve never done a lot of the things I have to do for StyleUp, but that’s also what makes it so exciting! I try to remind myself to enjoy all this craziness and realize what a special time it is vs. letting it stress me out completely. Some days I’m more successful than others!
Q: StyleUp is based out in Mountain View, CA and the Bay Area has become one of my favorite places to visit within the last year. Can you let us in on some of your favorite spots?
Kendall: StyleUp’s HQ has been my living room for the past year, which means it’s transitioned from Cambridge, MA to Mountain View, CA to now NY, NY. I absolutely loved Mountain View — though I spent about 90% of I‘d go to the farmer’s market on the weekend, especially because the weather is usually perfect. There are cute bookstores on Castro St. — Books Inc. has a solid cookbook section — and tons of places to eat outside. Mostly, I enjoyed walking around my neighborhood with all the lemon trees, the adorable houses, the bright flowers everywhere. Perfect escape from the Cambridge winter!
Q: You’ve spent a great deal of time on the East Coast before moving to the West, what is your favorite part about this region and is there anything you are still adapting to?
Kendall: I’ve boomeranged from East Coast to West Coast and back again. I love them both, and have been so lucky to live in such great places. My favorite thing about the West Coast was how many people were starting their own companies. It’s great to be so near all these amazing startups and talk with people in all the stages of startup life. It’s such a founder-friendly ecosystem. You’ve got to look at all areas of a startup before embarking, for instance, people may not know the answer to “what is sip trunking?” when in relation to business communications, but it is a good thing to know, especially if you plan on expanding your business.
Q: Kendall, this year on Yow Yow! we are focusing on the life of a 20-something and being a recent post grad transitioning out of college. What advice do you have for young adults at this age and moving into the adult world?
Kendall: That’s a great focus, and one I talk about often with our college interns. Find a job that truly challenges you. You’re going to make mistakes, but absorb them all as learning moments and don’t make the same one twice. You’re about to embark on a huge learning curve so get comfortable with being uncomfortable and enjoy the ride.
Q: Kendall you have established such an accomplished career. What is next for you and StyleUp? Are there any other endeavors that you would like to pursue outside of this?
Kendall: When I was younger, I was always so eager to move up to a better job or a cooler brand. Now, I’m so happy with StyleUp, I’ll work on this forever, if I get the pleasure.
To learn more about StyleUp and to sign up, please visit the website here.
