Women Of The C-Suite: “An Entrepreneur needs to ride the waves” With Jayna Cooke, Former Groupon VP and CEO of EVENTup

I had the pleasure of interviewing Jayna Cooke. Jayna has been navigating the startup world as an entrepreneur, leader, philanthropist and investor for the last decade. A former vice president at Groupon, Cooke is currently CEO of EVENTup, an online marketplace that helps companies find the perfect event space. She has been a part of […]

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I had the pleasure of interviewing Jayna Cooke. Jayna has been navigating the startup world as an entrepreneur, leader, philanthropist and investor for the last decade. A former vice president at Groupon, Cooke is currently CEO of EVENTup, an online marketplace that helps companies find the perfect event space. She has been a part of three startups — two that went public and EVENTup, which was recently acquired by Gather Technologies.

Thank you so much for joining us! What is your “backstory”?

My foundation really began when I moved to Chicago and started working at Echo Global Logistics. At the time there were only about 20 employees. As a result, I was given many opportunities to determine where I could add value and was able to try on many hats. Within two weeks, I was the #1 sales rep and held onto that title until the day I left.

In addition to my sales duties, I was able to put my hands in many things, from interviewing prospects, training groups of new employees, leading and managing a team, and developing ways to create multi-year multi-million dollar contracts. While I was still at Echo, I started working for The Point, which was Groupon. At Groupon, again I was so early I was able to work in multiple areas, even though my core role was VP of Business Development. I establish myself as the #1 sales employee until the time I left over four years later in addition to working on many partnerships, business development initiatives, and so much more. I am fascinated with Oprah and her ability to connect with people on a human level. Based on this, I started reaching out to her team and eventually was able to get Groupon on her Favorite Things show. After I left Groupon I started a non-profit and most recently EVENTup.

Why did you found your company?

I know it sounds predictable, but I really just saw an opening in the market and dove in.

What is it about the work you’re doing that’s disruptive?

My businesses are going digital. It’s not the future, it is here. However, the events industry has been stuck in the “way we have always done it”, which requires lots of phone calls and emails to understand what a venue offers and book it. The EVENTup solution provides this type information ahead of time so you save time and money.

We all need a little help along the journey — who have been some of your mentors?

Brad Keywell, one of the founders of Groupon the Lightbank, has always been extremely instrumental in my success. He is fearless when solving challenging and complex problems, passionate about building businesses, relentless in his pursuit of learning and can conquer anything he sets his mind too.

There is saying “the harder I work, the luckier I get” and that could not be more true. My mom laid a foundation for me that I am eternally grateful for. Where others see closed doors, she taught me how to get into the house. She showed me what grit really looked like, taught me that failure is not option, gave me the gift creativity, and I learned from that resourcefulness is your best strength.

How are you going to shake things up next?

Great question! Not sure exactly what my next step is but I do know that I will solve large problems in big industries.

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

· My mom has always told me “ride the waves”. The journey is long and there are many highs and many lows. As an entrepreneur you can feel like you are on top of the world and you can feel like you are the gum on a sidewalk that gets stomped on, just ‘ride the waves.’

· If you think you can’t… then you won’t”. You have to believe in yourself and what you are creating. The universe gives you the value you deserve. You need to be the catalyst for change, you are the only person at the end of the day that can make your dreams come true. Take ownership.

· “If you’re not selling, you’re buying.” I learned this from Sam Zell and it has been deeply impactful. People do not understand there is always an inverse impact in life. For example everyday you go to work you are buying, so you need to ask yourself if that is really what you want to be doing and for the price. Sam gave a great example of someone coming and offering $40M for a company of his and the question he asked himself was ‘if I had 40M would I buy my company’ the answer was no so he sold it. I think majority of people do not realize that everyday they are “buying.”

What’s a book/podcast/talk that’s had a deep impact on your thinking? Share a story with us.

I actually was just at the Tony Robbins seminar called ‘Unleash the Power’ and was really moved by the experience. The reality is that most people do not take responsibility for their actions and so Tony went thru different exercises to teach people why this is the case and how you can change this. It is an insightful process and helped me confirm beliefs I already had through research he has performed.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this. 🙂

I have so many! One that comes top of mind is Sara Blakely, the founder of Spanx. Her ability to navigate the world is really incredible and I applaud the business decisions she made that were against the ‘grain’.

How can our readers follow you on social media?

Instagram: Jaynacooke

twitter: Jaynacooke

facebook: Jaynacooke


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