From Failed Waitress to the First Female President of the New York Stock Exchange

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In 2018, the New York Stock Exchange (NYSE) made history. After over 200 years, a woman took the helm.

Stacey Cunningham's appointment as president was quite a moment, coming just months after the iconic "Fearless Girl" statue was placed defiantly facing the NYSE.

Cunningham's journey to the top wasn't exactly planned. While on a college break, she was looking for a waitressing gig, but her lack of experience was a roadblock. Her father, a stockbroker, helped her a temporary job on the trading floor.

"I just fell in love with the trading floor. I walked in and thought, 'This is what I want to do."

Her father’s influence in her career was undeniable. Though he never talked about what he did for a living (as a child she thought he was actually a “sock trader”) “when I was growing up, there was always a big painting of the New York Stock Exchange floor hanging on the wall in his den. When I became the President of the New York Stock Exchange, he gave me that painting”, she said in a Time interview.

Cunningham has often said that her career path did not have a clear plan for where she wanted to go and that her trajectory could be defined as "fairly nonlinear and unexpected."

Passion for finance wasn't something she pursued; it found her. That internship on the NYSE trading floor sealed the deal. "In that moment, I knew that's where I wanted to work," she told Time magazine.

But Wall Street was a man's world. When Cunningham became a member, there were only about 30 women compared to 1,300 men. It took 175 years for the Exchange to have its first female member. Muriel Siebert became a member in 1967. She had to get sponsored, and the first nine men she asked said no.

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When she finally became a member, there was no ladies' room for Muriel on the 7th floor where the members would get together. Eventually, they turned a phone booth into a bathroom.

"I was a female floor operator, and I never thought about it, I never thought for a moment whether that could happen or not, and whether or not it was an opportunity available to me," Cunningham told The Street Journal. “And it's because Muriel paved the way. I think it's really important to recognize that every time a woman pushes boundaries and redefines boundaries, she is redefining them for everyone who follows her”.

In a surprising move, Stacey took a break to attend culinary school. The program included six weeks working in a real restaurant, a period spent in the kitchen of Ouest, one of the trendiest establishments on the Upper West Side. The experience would later provide important lessons for his career on Wall Street.

“The bottom line is, whether in a kitchen or on a trading floor, you have to take responsibility for your mistakes, fix them, and move on.”

She returned to finance, working at Nasdaq before returning to the NYSE in 2012. She became COO in 2015, focusing on making markets more accessible to small businesses and investors. Three years later, she was appointed president.

Cunningham's tenure was marked by reforms aimed at simplifying market structures and increasing transparency. She tackled challenges head-on, implementing changes to prevent future volatility after the major 2015 trading disruption.

Though she stepped down in 2021, Cunningham's impact continues. She serves on the NYSE Board of Directors and advises private companies and Georgetown University. She is also an Operating Partner at Advent International.

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Here are some gems on how Stacey views business:

🟣 1. Fill the room with diverse voices.

When building a management team, Stacey views diversity of thought as critical.

🟣 2. Going public can be viewed as a social good.

Highlighting that the U.S is a nation built on shared success, Stacey views IPOs and public markets as an opportunity for companies to share their success with the community, whereas staying private longer actually contributes to the bifurcation of wealth.

🟣 3. Direct Listing allow companies to reimagine their path to public.

Slack and Spotify are the only companies that have taken this route to date, allowing them to decouple capital raising from going public. Companies primed for Direct Listing are well-capitalized with no need to raise new capital and have generally raised significant capital in private markets, giving them a large number of shareholders.

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Looking to Raise Money for Your Startup?

Check out these 37 female-led VC funds.

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