Kendall Herbst

When Kendall Herbst switched from working as a Conde Nast fashion editor to getting her MBA at MIT, she found she had a lot less time to think about what she was going to wear (a feeling we know all too well!). But Kendall still wanted to feel fashionable.

So, Kendall combined her fashion and business smarts and created StyleUp, a site that’s essentially a personalized style assistant. Every morning StyleUp users get an email with an outfit that matches their personal style and works with the local weather.

Read on to learn more about how Kendall manages the intense schedule of an entrepreneur and the “little bit crazy” she says it takes to be like her.

Let’s be honest: you have to be a little bit crazy to start a startup.

How did you discover your current job?

I created it! When I transitioned from working as a Conde Nast fashion editor to getting my MBA at MIT, I had a lot less time to think about what I was going to wear. But I still wanted to feel fashionable. I noticed there wasn’t a platform for personalized style inspiration -- something that would give you fashion ideas for your weather and taste. So that’s what I’ve create with StyleUp. It’s like an on-the-go, personalized fashion magazine.

Who’s on your team?

I have the world’s great teammates and any success StyleUp enjoys is a direct result of their effort. Chris is our CTO and is not only an amazing developer who understands the value of getting work done quickly and leanly, but he’s also a wonderful person and a genuine friend. Nathalie is our Art Director. She was a StyleUpper who reached out in spring 2013 and has made herself an integral part of the team. I can’t imagine doing StyleUp with anyone else, and true to her French/Italian roots, she has the best taste. We’ve had the pleasure of working with some talented college interns too. I know they’re going to conquer the world in their own way, and I’m excited to cheer them on. In general, StyleUp attracts wonderful people, and I hope that positivity and team spirit comes out in the product.

How do you organize your day?

I try to start off with a list of today’s must do’s and make sure to tackle at least one of them right off the bat. After that, each day takes on it’s own life. Some days that means me bouncing around NYC in meetings with brands and bloggers. Sometimes it’s me working with my team to coordinate a new product feature or brainstorming session. Sometimes it’s just me banging out the work solo, listening to embarrassingly bad pop music.

What is it about your job that makes you feel it’s the right fit for you?

At StyleUp, we have a daily product. So there’s no taking a day off. It would have become clear real quick if this concept wasn’t the right fit for me. I would have not been motivated enough to keep working on the product every ... single ... day. It’s easy to be passionate about an idea for a week or a month, less so to sustain it beyond a year. I look forward to many, many more years of it and all the crazy adventures to come.

What challenges keep you awake at night?

So many! I’m even answering these questions at 11 p.m. with no end in sight to my day. I have to make sure that we hit our goals so that we can fundraise from investors as needed. I also think a lot about keeping my teammates motivated, keeping StyleUppers excited and ensuring that we’re going as fast and leanly as we can toward our big vision.

Is work/life balance ever a problem with you? If so, what is one no-fail tactic you use to create balance?

I’ve come to not really think about work/life balance. Your life doesn’t stop when you’re at work, right? And you sometimes think about work when you’re away from your desk. In my head, I’ve done away with the work/life balance, and I just see it all as life and as work. I work usually seven days a week, but I can be honest with myself and slow down if I feel burned out. There’s nothing that some red wine, a Bravo TV marathon and an early bedtime can’t cure.

Was there ever a moment in your career where you’ve thought, “I made it!” What was it?

The first day walking into Conde Nast as the fashion news editor of Lucky magazine was a really big life moment. I had grown up dreaming of becoming a fashion editor, and at 24, I was. Also, getting into Y Combinator was a real “pinch me” moment. I felt so honored to get to go work with those amazingly talented people. Overall, I don’t have a “I made it!” moment, and part of me hopes that I never do and that I keep looking to see what’s next.

What are some of the rules you live by?

Do what you can with what you have. It’s so easy to focus on what you don’t have -- a nicer apartment, a technical co-founder, a Series A from Andreessen Horowitz, a higher salary or better hair. Big and small, things that you feel are blockers to what you want to do or who you want to be can be paralyzing. Instead, I try to focus on what I do have and make the most of it. Being grateful is a great path toward being happy.

What qualities does it take for someone to be successful in your line of work?

Let’s be honest: you have to be a little bit crazy to start a startup. The odds are not in your favor, yet you have to doggedly ignore reality and 150 percent believe you will be the exception. You have to inspire others to join you in that vision and stick with you through lean times. You have to be able to fly very low and handle minute details and fly very high and define your company’s purpose for being. The role takes a very resilient and nimble personality.

What one piece of advice do you wish you could tell a 21-year-old version of yourself?

Learn to code! I’m learning now, but it would have been nice to have 8 years of experience under my belt already.