Bernie Madoff’s Niece on Her Mission to Fight Pay Inequities

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.”

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