Jayna Cooke

Jayna Cooke

CEO and Partner of EVENTup

Founder of Closet Angels

Chicago, IL



Just like Rent the Runway’s co-founders, there are a ton of women who have leapt into the uncharted, often-insane world of entrepreneurship. We’re inviting these risk-takers to be part of a community we’re calling “The Real Runway:” a collection of voices to motivate and inspire your own runway, whatever that may be.



It all started with… Groupon.


For four years in a row, Jayna Cooke was the top salesperson at Groupon. In fact, she’s credited with bringing in 25 percent of the start-up’s total revenue in 2009 alone. Though she wasn’t even 30 years old at the time, she earned a reputation for being one of the most successful sales and business development pros in tech start-ups… ever. But she craved a new challenge and founded Closet Angels in 2012, a non-profit that sells used designer clothes to benefit St. Jude’s Children Research Hospital. Two years later, she was recruited to revive the struggling start-up, EVENTup, a service that simplifies the search for event spaces. As CEO, she completely revamped the company. Hear what Jayna has to say now that she’s her own boss.



Bag, Kotur



What’s life like as a CEO?


The second I wake up, there are a million things that run through my head. I take my responsibilities very seriously and start working and solving problems right away. I’m proud of my resourcefulness — I always try to figure out solutions to any problems I’m faced with. I really don’t like the phrase, “I can’t.” I wholeheartedly believe there is always a way to make things work. I’m naturally very hardworking and struggle with balance — but I make sure I give enough time to my friends and family, as well as my team.


I love challenges and coming up with creative solutions. I jump out of bed excited to do that every day.


How do you respond to hearing “No?”


I hear that word all day long. The rejection factor is huge in this world. Even if you look at Groupon, it’s a $7 billion company and people still hate on it today. You just have to trust your gut. It also helps to keep positive people around who are solution-oriented and don’t dwell on negativity.





What’s the greatest lesson you’ve learned?


I’ve learned to relax and roll with the punches more. I’m often in a room with people who have 10 or even 20 years more experience than me, which has been very humbling. I’ve learned to allow people into my world, and as long as I get the right results, let them do things on their own. Relinquishing control is an ever-evolving lesson. People in power — like me — have a hard time learning how to trust. But I’ve found that when I let go, what I get in return is more valuable than the control I gave up.


I never want to be the smartest person in the room.


How does style factor into your life?


One of the reasons I created Closet Angels was because I love clothing. I love that it’s a creative way to express who you are. When you meet someone, your outfit is probably one of the first things they notice about you. So I like interesting pieces that don’t overpower the person wearing them. And cute, comfortable shoes are a must. I hate when people can’t walk in their shoes!



Bag, Kotur; Ring, Nineteen Pieces; Bracelet, Eddie Borgo; Dress, Vionnet



When you need a jolt of inspiration, what do you do?


I workout, walk my dog, maybe even do some online shopping. I need to do one thing for myself every day. I also find meeting young entrepreneurs with new ideas really motivating — you can just feel their passion.



My mantra is ‘Work like a captain and play like a pirate.’ It’s easy to get wrapped up in the day-to-day, but I always make sure that my team and I are having fun.


What’s your advice to other entrepreneurs?


Find what makes you happy. It’s different for everyone, but listen to yourself and understand what it means to you. When you’re chasing your dream, it serves as a reminder of why you do what you do. For me, I love solving problems. I love my team, friends and family. I love my dog to death. I try to find joy every day. And that fuels me.





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