Kendall is a former fashion editor who has written for NYmag.com, Lucky, InStyle, and NBC. She recently scrapped that glamorous life and is pursuing an MBA at MIT Sloan, in hopes of becoming an entrepreneur.
Last we spoke, I was living in Cambridge, MA working on StyleUp between my MIT Sloan classes. Now, I’m in Mountain View, CA working StyleUp full-time. It’s amazing and crazy and daunting and strange and wonderful. Recently, my co-founder and I even raised a little bit of investment capital which makes me feel like I’m just starting to make it as an entrepreneur. There is a very long road ahead, but I thought it might be useful to hear a few things I’ve learned so far.
1. It’s a roller-coaster – find your center. There are high highs and low lows. Your startup is a finalist in a contest! You lost the contest. You meet an angel investor who is interested in giving you lots of money–then they never email you back. You’re going to be featured in a magazine–the editors kill the story. Through it all, you have to be able to hold your control, not only to inspire your team but also to just get through the day. This past summer, anytime something went wrong with StyleUp, I would be in a funk for hours. That’s not sustainable or healthy. Nowadays, we have our fair share of negative user comments on the website. I try to understand the complaints without letting them deter our momentum. Do yoga, have a glass of wine, adopt a kitten–whatever you need to do to stay calm and stay the course, do it.
2. Your life goes from being surrounded by many, to a few, to one. At business school, I was constantly surrounded by people. In class, in the Retail Club, in study groups over the weekend, I was never lacking for socializing. Once I started StyleUp, I had way less time to linger over coffee with my friends. Now that I’m working on StyleUp full-time, I spend a lot of my time alone. Strip away the distractions, put on your blinders and just crush it. However, when you can socialize, don’t talk about work. Your friends know you work a lot; they probably do too. They care mostly about how you are, not how your business is.
3. You are only as strong as your weakest link. If you have a co-founder or employee or an intern or someone orbiting your life who isn’t pulling their weight, cut them loose. You have to. Without sounding too Godfather-inspired, it’s not personal, it’s business. Their bad energy will bring everyone else down. Don’t feel guilty about making those choices and make them sooner than later.
4. Pay it forward. While this lesson isn’t specific to entrepreneurship, its value has become incredibly clear to me as a startup founder. I’ve had several wonderfully generous executives or fellow entrepreneurs take time out of their day to coach me through big choices. In turn, you have to be gracious and generous. That mentality has shaped how I view our College Ambassador program. I will do anything for those girls to succeed and get the internships/jobs that they want. The fashion world’s a big ladder, and you have to reach down your hand for the people below you who deserve it.
5. Prepare to step away from fashion. Unexpected, right? You start a fashion/tech company, but you have a lot less fashion in your life. Don’t get me wrong, I spend just as many hours in my days scanning street style blogs as I did when I was at Lucky magazine. But in my own life, luxuries like manicures or a new Outnet purchase are G-O-N-E. Every disposable cent you have goes into your company. Buy a nail file, and embrace the unpolished look. Learn to work with what is in your closet vs. impulsively buying more–that’s what StyleUp is for after all! You just don’t have time to care about the externalities which is a bit sad and also surprisingly liberating.
6. Remember who you are serving. When I have moments of doubt or frustration with StyleUp, I think about some of our users who I’ve gotten to know over the past year. I think about how they look forward to getting a dose of outfit inspiration, and it’s my job to find the best one. I think about how they want e-commerce links at a low prices because, honestly, who can or wants to pay $1500 for boots? I think about how we need more diverse images of beauty in both body shape and ethnicity. Those thoughts fuel me to try really hard. I care so much about how our users view StyleUp. Remembering the end result can be really helpful in pushing you along day-to-day.
7. Don’t give up. There will be moments when you will want to. It might be a Sunday morning after a fight with your co-founder. It might be a Friday afternoon when a big meeting goes badly. Do. Not. Give. Up. Ever. I draw a lot of inspiration from people who have stuck to their seats. Jenna Lyons has been with J.Crew for TWENTY-TWO years. I imagine there have been some real ups and downs. I imagine that she’s been asked to join other brands. She’s stayed, and I admire her for it. When it comes to professional choices, one question I often ask myself is: “What would Jenna do?” She’d stick it out, and she’d wear something awesome.
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