How Bernie Madoff's Niece Turned a Family Scandal Into a Mission to Fight Against Pay Inequities Jess Ekstrom discusses her passion for championing women entrepreneurs and tapping into the power of true optimism.

By Terry Rice Edited by Dan Bova

Opinions expressed by Entrepreneur contributors are their own.

In this episode of Reclaim + Advance, we'll hear from Jess Ekstrom. Jess is the founder of Headbands of Hope and Mic Drop Workshop. She also invests in women-owned businesses, is a two-time bestselling author, a top-rated speaker, and a new mom. Jess and her companies have been featured on Today, Good Morning America, 17 magazine, Vanity Fair, Forbes, People, and more importantly, they've helped millions of women and girls around the world.

For years Jess Ekstrom avoided speaking about a formative event in her family life — her family getting swindled out of money by her uncle, Bernie Madoff. But on the show, she explains what spurred her to start speaking about formative challenges, and how true optimism isn't naive.

In this episode, you'll hear:

  • How Jess turned a family scandal into fuel for her entrepreneurial journey.
  • The shocking pay gap revelation that inspired Jess to champion women speakers.
  • Why simplifying complex ideas is key to connecting with your audience.
  • How embracing vulnerability can amplify your impact as a speaker and leader.

I'll share a few of my favorite quotes from my conversation with Jess below:

On Authentic Expertise:

"A lot of [the] time, the thing that you teach to others is the thing that didn't come naturally to you. It's the thing that you had to will yourself to learn and to practice."

The Power of Simplicity:

"I like to simplify the complex for people. We make things too complicated, whether that be entrepreneurship or speaking or writing. I like to make things feel attainable to someone."

Embracing Struggle in Storytelling:

"No one wants to learn from someone who's just naturally good at something. Sometimes the greatest lessons that you have to share with others come from your worst moments."

Click here to listen on your platform of choice, or tune in below.

Terry Rice

Author, Speaker and Business Coach

Terry Rice is a keynote speaker, performance coach, and author who helps leaders and teams break through barriers, embrace discomfort, and unlock their next level of personal and professional growth.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Editor's Pick

Business News

You Can Get Paid $18,000 More a Year By Adding AI Skills to Your Resume, According to a New Study

Employers are emphasizing AI skills — and are willing to pay a lot more if you have them.

Business Ideas

70 Small Business Ideas to Start in 2025

We put together a list of the best, most profitable small business ideas for entrepreneurs to pursue in 2025.

Leadership

The Difference Between Entrepreneurs Who Survive Crises and Those Who Don't

In a business world accelerated by AI, visibility alone is fragile. Here's how strategic silence and consistency can turn reputation into your most powerful asset.

Leadership

7 Steps to De-Risking Big Business Decisions Before They Backfire

When the stakes are high, these seven steps can help you avoid costly mistakes, eliminate bias and make smarter decisions that actually scale.

Business News

United Airlines Says It Is Adding Extra Flights in Case Spirit 'Suddenly Goes Out of Business'

Rival airlines, including United and Frontier, are adding new routes as Spirit cuts 12 cities from its schedule.

Employee Experience & Recruiting

Here's the Real Reason Your Employees Are Checked Out — And the Missing Link That Could Fix It

Most disengaged employees aren't exhausted — they're disconnected, and storytelling may be the key to rebuilding that connection.