Gen X CEO of a popular retail chain was once a single mother surviving on $882 a month and pinto beans before finding success

Kelly Cook grew up riding the poverty line, skipping a four-year college to help her mother with finances. She’s since held C-suite roles at DSW, Kmart, and now, David’s Bridal.

Jun 27, 2025 - 16:52
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Gen X CEO of a popular retail chain was once a single mother surviving on $882 a month and pinto beans before finding success
  • The Gen X CEO of David’s Bridal lived off $882 a month, cornbread, and pinto beans when she was first starting her career. Juggling school work and a side job as a young single mother, Kelly Cook barely scraped by before rising to executive positions at DSW, Kmart and Pier 1 Imports, and helming the popular American bridal chain this April. Others like Shark Tank’s Mark Cuban and Starbucks’ Howard Shultz have similar humble origin stories. 

For some, the road to success starts with a cushy MBA and a fast-track grad scheme. For the CEO of the wedding dress giant, David’s Bridal, it was a rockier start than most. She was barely scraping by, juggling working weekends as a bartender, with taking care of her young child and college when she started out. 

“My take-home pay per month when I divorced her father and was living on my own as a single mom was $882. My car note was $350, and my rent was $350,” Kelly Cook told The New York Times in a recent interview.

To make do with what little she had in the early days of her career, she “ate a lot of pinto beans and cornbread.”

Cook is currently helming a bridal dress giant with 200 stores across the U.S. and Canada, boasting around 5,000 employees. But rewinding a few decades back, her life looked a lot different; she grew up without much money, having to get a job right after high school to help support her mother. Cook was later able to pursue higher education, marrying “very, very quickly” into her years at junior college and having a child. 

The 58-year-old executive’s first white-collar job at Continental Airlines would send her on a journey to executive roles at retail titans like DSW, Kmart, and Pier 1 Imports. But those early days, taking classes during the day and working at night, taught her an invaluable life lesson.

“It proved to me that life’s tough, but you don’t have to worry about life,” Cook said. “Just worry about today.”

Cook’s beginnings: riding the poverty line and juggling school, work, and a kid

The David’s Bridal executive has a very different origin story than the likes of Elon Musk and David Koch. 

Cook was raised somewhere between the lower and middle-class by a stay-at-home mother and firefighter father, but her life took a turn in high school when her parents got divorced, forcing Cook to give up a scholarship at Baylor University to help with her mom’s bills. She was later able to attend a junior college—taking every math class available—while also falling in love, quickly marrying and having a child eight months later. 

While Cook was still in school, she and her husband split, ushering in the responsibility of being a single mom.

“Classes were during the day, and I worked at night,” Cook recalled. “I was a Bennigan’s bartender on weekends, and during the week I worked as a registration clerk in the emergency room at the hospital my mother worked in.”

Thanks to her determination and passion for math, the Southern-born CEO went on to be a finance and logistics analyst for Continental Airlines in 1994. She worked her way up to director of customer relations management the airline business, proving her leadership chops to take on large administrative roles. 

Cook went on to be the vice president of employee and customer engagement at $93 billion company Waste Management Inc., before taking on the role of chief marketing officer at huge retail chains including DSW, Kmart and Sears, and Pier 1 Imports. Coming in as David’s Bridal’s CMO in 2019, she worked her way up to the CEO gig this April. 

Other CEOs who have humble origin stories

Cook’s not the only CEO who had to grind the pavement to make their own success. 

Howard Shultz, the former CEO of $111 billion coffee behemoth Starbucks, grew up in a housing project in Canarsie, Brooklyn, and was the first in his family to attend college. Pret A Manger’s CEO Pano Christou was also born to a working class family, and got his start at McDonald’s working the floor for $3.40 hourly. 

Doug McMillion was a Walmart warehouse worker at just 17 years old making $6.50 unloading trucks before rising through the ranks over 30 years to the company’s chief executive role in 2014. And Kurt Geiger’s boss Neil Clifford cleaned bathrooms at a Fiat car dealership for extra cash while trying to get a foot in the fashion world. 

Serial investor Mark Cuban also had a rough start to his entrepreneurial career. The former Shark Tank icon was flying by the seat of his pants during his 20s when first launching his technology company MicroSolutions. Cuban was strapped for cash, taking no days off for years because he was “broke as f-ck”.

“I was living, six guys in a three-bedroom apartment, which wasn’t great. It was a sh-thole,” said in an interview with Sports Illustrated.

This story was originally featured on Fortune.com