Meet the 33-Year-Old Professional Negotiator Who Got Her Start by Talking Her Way Into an Ivy League Degree

Courtesy Ashley Feinstein Gerstley

Ashley Feinstein Gerstley managed to turn a 2006 rejection letter from the University of Pennsylvania into an acceptance. She credits her success to something many of us don't do after being told "no." Instead of giving up, she asked again.

"It's a lesson my dad taught me, to always ask," she says. "Once, we got to go backstage at a BB King concert because he asked."

Today, Gerstley, 33, is the founder of The Fiscal Femme, a financial services company that offers consulting and classes to help women make more money. Although much of her focus is on negotiation in the workplace (check out her best tips to snare a raise), she traces the inspiration for the company back to that Ivy League negotiation she initiated at age 20. "That shaped so much," she says. "Like how I live in the world and believe that I can ask for things."

How Gerstley talked her way into the Ivy League

Gerstley was about to start her sophomore year at Tulane University in New Orleans when Hurricane Katrina hit, closing the campus for the first time since the Civil War. Students were asked to continue their education elsewhere for one semester and, luckily, many schools came to the aid of the displaced. After a "mini-application process," Gerstley headed to Penn.

"The plan was this would be for the semester," she says. "But I ended up loving it and getting really involved...that is where I wanted to be."

Gerstley, first row on the left, poses at her Penn graduation with some classmates.
Courtesy Ashley Feinstein Gerstley

With the help of a mentor, who was a Penn '76 alum, she put in an application to officially transfer to Penn rather than return to Tulane—only to receive a rejection letter. When she called her mentor with the disappointing news, he asked her, "So you're just going to give up?"

"That was the spark," Gerstley recalls.

She scheduled a call with the dean of admissions to state her case. Ahead of time, she wrote out her argument and practiced it on friends at coffee shops. On her mom's advice, she took the call somewhere near the dean's office, just in case he wanted to meet with her in person. It's a move that, in retrospect, she calls "so critical."

Minutes into the conversation, she started crying. "It was not a negotiation tactic," Gerstley says. "I was just upset and that was my first inclination. He said, 'I know who you are. Where are you? Let's talk about this.'" Because she was already nearby, she was able to quickly get to the dean's office to make her appeal in person.

Just having the negotiation is a lot of the battle, even though it's really scary to show up and have these conversations.
Ashley Feinstein Gerstley
founder, The Fiscal Femme

"I was probably a terrible negotiator," she says. "But just having the negotiation is a lot of the battle, even though it's really scary to show up and have these conversations."

The face-to-face meeting sealed the deal. Gerstley would be allowed to attend Penn in the fall of 2006, provided that she earned good grades in her summer classes. She graduated in 2008 with a bachelor's degree in finance from the university's Wharton School.

Less than five years later, Gerstley founded The Fiscal Femme. Now she regularly speaks on panels about how to negotiate better deals.

"We often hear 'no' and are just like, 'OK'," Gerstley says. "But it's helpful to understand why and see if there are ways to make it work for everybody."

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