Female Disruptors: How Jess Ekstrom of Mic Drop Workshop is Shaking Up New Opportunities For Women Speakers

Yitzi Weiner
Jul 14 · 6 min read
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As a part of our series about women who are shaking things up in their industry, I had the pleasure of interviewing Jess Ekstrom.

Jess is the founder and CEO of Headbands of Hope, a company that donates headbands to kids with cancer. Jess is also a professional speaker and host of Mic Drop Workshop, an online course and community to empower women to get more keynote spots.


Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

My backstory begins selling my American Girl Dolls on eBay when I was 12. That’s when my entrepreneurial spirit started to kick in… until I started selling my sister’s toys and my operation got shut down.

Then when I was in college, I was interning for a wish-granting organization and I saw that kids loved to wear headbands after losing their hair to chemotherapy. So my junior year of college, I launched Headbands of Hope. For every headband sold, one is given to a child with cancer.

Now, I tell the story of Headbands of Hope in my new book, Chasing the Bright Side, and as a professional speaker.

I was interning for Make-A-Wish and I saw a lot of kids that were losing their hair to chemotherapy. They’d be offered wigs or hats, but a lot of them wanted to wear headbands instead of covering up their heads.

I did some Google searches and realized that no one was providing that, so I thought, “why not me?”

I believe that’s the moment when you become an entrepreneur. Not when you hit a million dollars in sales or not when you make it on a list, but when you decide to create what you wish existed.

I started Headbands of Hope out of my dorm room in college in 2012: for every headband sold, one is donated to a child with cancer. To date, we’ve donated over half a million headbands to kids with cancer and have reached every children’s hospital in America and 15 countries.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

One of the things I noticed as I started to speak professionally was how few women there were on stage. Especially in the business and tech space, there would be all male lineups or just a token woman here and there.

I’ve met so many amazing women with incredible stories who should be on stage telling them, and getting paid to do it. However, there’s a discrepancy to male speakers versus women speakers who are putting their names in the hat for keynote spots.

I want to change that and get more women on stage as keynote speakers, so I started Mic Drop Workshop. Mic Drop Workshop is an online course and community to give women the tools they need to become paid speakers.

We all need a little help along the journey — who have been some of your mentors? Can you share a story about how they made an impact?

My dad. As you’ll read in my book Chasing the Bright Side, he took a huge gamble on me and gave me a loan for my first round of production. The manufacturer I was working with was fraudulent and ran with the money. Nevertheless, he still believed in me and I’m proud to say I’ve paid him back… with $1 interest!

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

1. Remember Why You Started

Starting a company can be really, really hard. There, I said it. Starting and building my business has been the most challenging thing I’ve ever done, but it has also been the most rewarding. I’ve learned that meaningful work doesn’t mean it’s easy — it means it’s going to be worth it. Whenever times get tough, I pull up a file on my computer of all the pictures and letters we’ve received from hospitals (thousands of them) and remember why I started this in the first place. At the end of the day, success is not what it looks like to others, it’s what it feels like to you.

2. Every expert was once a beginner.

A really freeing revelation for me was that every expert was once a beginner.

Teachers first had to be students. Anyone who runs first had to learn to walk. Everyone who’s ever solved a problem was once just pondering an idea. But everyone who’s done something great had to have a moment where they turned that idea into action.

So if everyone had to start somewhere, why not here? And if success isn’t about our skills or all of our expertise, then why not you?

Everyone who’s ever done something great has always had to believe that they could be the ones to do it.

3. If you want it bad enough, you’ll figure it out.

I got my first logo by persuading a graphic design teacher to make my logo creation an assignment for her class. I made my first website by paying a computer design student in Chipotle burritos.

When I got the idea for Headbands of Hope, I didn’t have a lot of money or experience, but I looked at what did have and started there.

It’s so easy to look over the fence and think about what you don’t have that’s holding you back. Instead, focus that time and energy into being resourceful with the things that are right in front of you.

How are you going to shake things up next?

Through Mic Drop Workshop, I’ve become really passionate about making people feel qualified to tell their story. I’d like to keep creating products and programs to give people the tools and confidence they need to tell their story whether that be through speaking, book writing, podcasting or whatever medium they choose.

Do you have a book/podcast/talk that’s had a deep impact on your thinking? Can you share a story with us?

Marc Randolph’s That Will Never Work is the birth story of Netflix. It really goes to show that success is within all of us and you just have to be scrappy and adaptive to figure it out. He talks about the Netflix site crashing within the first fifteen minutes of being live and so many other hurdles that they came across that really normalizes the process of going for it.

I was thrilled when Marc actually endorsed my book, Chasing the Bright Side.

We are very blessed that 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. :-)

Sara Blakely for sure. She humanizes the hustle and makes entrepreneurship fun and not feel so heavy. I would give her unlimited headbands for life if she’d have a meal with me! :)

How can our readers follow you online?

www.instagram.com/jess_ekstrom

www.facebook.com/jessekstrom

www.twitter.com/jess_ekstrom

This was very inspiring. Thank you so much for joining us!

Authority Magazine

Leadership Lessons from Authorities in Business, Film…

Yitzi Weiner

Written by

A “Positive” Influencer, Founder & Editor of Authority Magazine, CEO of Thought Leader Incubator

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

Yitzi Weiner

Written by

A “Positive” Influencer, Founder & Editor of Authority Magazine, CEO of Thought Leader Incubator

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

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