Every Entrepreneur Is a Negotiator—Jess Ekstrom's Story Proves It
Every entrepreneur is a negotiator, whether they realize it or not. Jess Ekstrom’s journey from a college dorm room to leading a global brand proves this truth. She started Headbands of Hope with just $300. By 2024, her company had donated over one million headbands to children fighting cancer in 22 countries. Along the way, she negotiated share sales, joined boards, invested in startups, built Mic Drop Workshop to help women speak publicly, and published her own book through her own imprint. Then she made her boldest move: she resigned as CEO—not from her company, but from her title. She did the math on where her time created the most value and renegotiated her role. This same discipline turned every major deal into a win. Her story shows that the question isn’t whether you’ll negotiate. It’s whether you’ll do it well.
You Are Already Negotiating—Even If You Don’t Know It
Most entrepreneurs don’t see themselves as negotiators. They think of themselves as builders, operators, or visionaries. They imagine negotiation happens only in boardrooms with lawyers. This is a costly mistake.
In her book Making It Without Losing It, Ekstrom shares a simple formula: Situation + Space + Choice of Action = Intention. By pausing before reacting, you make decisions that match your true interests—not your automatic habits. Research from Columbia University Medical Center backs this up. A pause of just 50 to 100 milliseconds helps your brain filter out distractions and improve decision accuracy.
Without that space, entrepreneurs accept default terms on contracts, roles, and expectations. They never realize those terms were negotiable. Ekstrom calls this “anxious ambition”: running forward not because you know where you’re going, but because stopping feels like falling behind. It’s the autopilot trap, and it costs founders more than they think.
The Education That Comes with a Price Tag
Ekstrom’s negotiation education started the hard way. Early in her career, she signed what she later called a “really bad deal.” She did it without a lawyer and without advocating for her own value. Leaving that contract cost her hundreds of thousands of dollars. She calls it tuition—not failure.
What she did next matters more. She learned to negotiate share sales, secure board seats, and make smart investments. The same founder who once underestimated her leverage became a master at creating it—even at the top of her own company. She realized her CEO duties were eating up the creative energy that built the business. So she stepped out of the role, hired an operator, and became Chief Creative Officer. Research on “job crafting” by Wrzesniewski and Dutton shows that professionals who actively reshape their tasks feel more fulfilled and less burned out. Your job description isn’t a contract. It’s an opening bid.
The Third Option: Create New Choices
Most entrepreneurs treat negotiation as a simple yes or no. Saying yes too often leads to bad deals. Saying no too often closes doors for no reason. Both leave value on the table.
The smarter move—the one Ekstrom models—is the third option: reject the choices in front of you and propose new ones. When she published her book, she didn’t wait for a traditional publisher or give up. She started her own imprint and controlled every term. Harvard Law School’s Program on Negotiation calls this integrative bargaining. It moves from a fixed-pie mindset to collaborative value creation. The best dealmakers don’t just negotiate the deal. They negotiate the frame.
The Negotiations That Define You
The most important entrepreneurial negotiations are often the least visible. Beyond contracts and equity terms lie tougher ones:
- Negotiating with your own standards: Knowing your value well enough to walk away from deals that don’t reflect it.
- Negotiating with people close to you: Unmanaged expectations from family and friends can drain your business energy.
- Negotiating what success means: The U.S. Census Bureau recorded nearly 5.8 million new business applications in 2024. Few of those founders stop to ask whether the success they’re chasing is truly theirs.
Ekstrom herself is the best answer to anyone who says they’re not a natural negotiator. She wasn’t always great at this. She signed a bad contract. She underestimated her leverage. She learned—deal by deal, mistake by mistake—until negotiation became a core skill. That’s not a talent story. That’s a skill story. And every elite negotiator has a version of it.
When I interviewed Ekstrom on the Negotiate Anything podcast, she explained how the same skills that shaped her business deals also built her public speaking career. She now teaches those skills to countless women through Mic Drop Workshop. You can watch the episode here.
Final Thought: Negotiate with Intention
Every entrepreneur is already negotiating. The real question is whether you’re doing it with intention or on autopilot. Jess Ekstrom’s journey—from a dorm room in Raleigh to over a million headbands donated across 22 countries—proves that those who master this skill don’t just make it. They make it without losing themselves along the way.
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