*By Chloe Aiello* *As Cheddar reflects on 2018, we are profiling the most innovative, flamboyant, and often-controversial entrepreneurs and corporate leaders who delivered the year's most memorable moments in business. Of the CEO Class of 2018, who was crowned Biggest Flirt? Class Clown? Most Likely to Succeed? Check [here](https://www.cheddar.com/) for all the Cheddar Awards and more year-end coverage.* Equity trading runs in Stacey Cunningham's blood. Her father was a trader, and in 1994 she followed in his footsteps and took an internship on the floor of the exchange that she would eventually run. Cunningham eventually earned a clerkship at NYSE. Things were different then: she was one of a few dozen women among more than 1,000 men, [Fortune reported](http://fortune.com/2018/05/22/nyse-president-stacey-cunningham-woman/). Circumstances have changed, but not by quantum leaps. There's still comparatively few females running Fortune 500 companies, and the majority of the women on the exchange floor work for media operations. Cunningham has spent most of her almost 25-year career at the NYSE, with brief interludes for culinary school and a few positions at rival exchange Nasdaq. Cunningham said she has been "fortunate" that gender has not adversely affected her career. "I’m not saying that every woman would have had that same experience. I’m sure there are women who tried to draw lines and they were ignored. I was fortunate that when I drew lines people stayed outside them," she [told The Guardian](https://www.theguardian.com/business/2018/jul/20/stacey-cunningham-new-york-stock-exchange-first-female-president). Cunningham stuck with it through all these years, largely because she loved the energy at NYSE. “That community is really unparalleled," she told Cheddar. Cunningham started at the bottom ー and now, at 43, she's the first female president in the 226-year history of the New York Stock Exchange. But she's also taking the helm at a particularly challenging time. Some of the obstacles in the path of Cunningham's first year as president include a rise in electronic trading (and subsequent decline in human traders) and NYSE's eroding market share at the hands of a deepening pool of competitors, among others. Cunningham isn't daunted by the difficulties facing the exchange. Although Cunningham was instrumental in architecting the NYSE’s technological upgrade, she's not giving up on human traders altogether. Instead, she uses a strategy called "people and technology" ー automating some parts of trading without sacrificing the human element, which is key for investor confidence. "We think we've nailed it," Cunningham [told Cheddar](https://cheddar.com/videos/nyse-ceo-people-and-technology-makes-the-big-board-the-best-place-to-ipo). And yet still NYSE is losing market share to exchanges run by big banks, which made up about 40 percent of total trades in spring 2017, [according to CFA Institute](https://www.cfainstitute.org/en/advocacy/issues/dark-pools). Cunningham insists companies still want to list on NYSE -- which makes 2019 a very particularly exciting time for the exchange. A roster of technology unicorns ー including Airbnb, Lyft, Uber, Pinterest, and Slack ー are all reportedly considering major public debuts next year. Due to an abundance of venture capital and a bit of an aversion to regulation, [many companies are waiting to IPO](https://www.vox.com/2014/9/11/6134529/a-new-york-stock-exchange-exec-explains-why-ipos-are-becoming-less). The upcoming slate of expected debuts will provide a major opportunity for NYSE to pick up some market share. And Cunningham thinks NYSE has a fair shot. “When you look over time, you see 43 out of the last 47 large IPO ー IPOs that raised more than $700 million ー they’ve all chosen to list on the New York Stock Exchange, because of what we can provide them,” she said. Her confidence doesn’t mean the NYSE is complacent.Cunningham is a big proponent of loosening regulations around public debuts so companies can list sooner and investors of all sizes can participate. She said she’s been spending a lot of time in D.C. pushing for policies that “provide investor production, but also balance /[it/] with issuer flexibility.” “We want to make sure that the public markets are providing opportunities for companies of all sizes and investors of all sizes,” she said. “When we look at the growth of this nation, it’s been driven by companies raising money so they can go out and change the world. And they're giving investors an opportunity to share in that success.” Cunningham says she has the freedom to shake things up at NYSE. Her boss, Jeffrey Sprecher of the Intercontinental Exchange, is himself a disruptor. He’s given quite a bit of leeway to go forth and instigate change. “Frankly that was a great thing for me personally, being part of an organization that now came in with a guy like Jeff being able to say: ‘Go re-invent this place, nothing is sacred,’” [Cunningham told Fortune](http://fortune.com/2018/12/07/nyse-president-stacey-cunningham/). “Knowing I can do that for an organization I love so much is ー I couldn’t have asked for a better job,” she added. For her climb from intern to first female president and for the promise ahead, Cunningham is the Cheddar class of 2018’s Most Likely to Succeed.
