Cole Whaley says creating business plans and reading business books are his hobbies. When pressed, he admits he also likes playing ping pong—which is fitting because his career path was seemingly back and forth. Yet, as Whaley points out, it’s all about sales and hospitality.
When he was three, Whaley was adopted by an entrepreneurial single woman in Cleveland, Ohio. The man she was then dating took on a fatherly role. Even after the relationship ended, Whaley says he raised him as a son.
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A family friend, Jim, had a “big” sales job at a large manufacturing company. He was always dressed in a white starched shirt and wore a fancy watch. Whaley aspired to be like Jim and dreamt of a business career. But in third grade, Whaley volunteered to serve breakfast in the school cafeteria. It was the first time he saw a professional kitchen. He was fascinated by the equipment and huge walk-in refrigerator, feeling inspired to become a chef instead.
Whaley’s mom worked in hospital administration for 28 years, later starting her own business running group homes for people with disabilities. His dad owned a series of retail stores and got into real estate. Following in his parents’ footsteps, Whaley’s entrepreneurial pursuits started as a teenager.
“I started a snow shoveling and lawn mowing business and made flyers to promote it,” he says. “I got lots of business and was proud when I was able to buy a remote-control car with my own money.”
After high school, Whaley wanted to go to Cleveland State University. He hadn’t applied; he simply showed up and talked his way in. They didn’t have an entrepreneurship major, so he created his own interdisciplinary degree combining communications and business.
He started in sales working for the school newspaper as the head of advertising. He drummed up new business and doubled their ad sales. As a senior, he interned at Cleveland Magazine and had trouble selling full-page ads. He came up with the idea of selling business card-sized ads from multiple advertisers to fill the pages. He says the publisher still tells the story about his ingenuity.
After college, he moved to Phoenix, Arizona, and worked for Monster.com for five years in sales.
Cole Whaley
“I really liked taking clients to fine restaurants, and I started thinking again about becoming a chef,” Whaley says.
He left Monster.com and moved to Silver Springs, Maryland, with his wife and decided to start a food truck. That inspired him to attend culinary school at L’Academie de Cuisine, where he learned how to cook, create menus, and buy restaurant supplies.
“I ended up buying a restaurant and was the head chef,” Whaley says. “I loved the business side of it, but I didn’t want to be a chef.”
He noticed the biggest challenge in the restaurant business was hiring, so he sold his restaurant to start a hospitality recruitment firm. At that point, he realized he had officially created a career combining his passions from childhood: sales and hospitality. To find clients, he set a goal called “The 50 for 50”—he would contact 50 CEOs in hospitality in 50 days.
“I figured out their email addresses and got through to the CEOs of Red Lobster, Shake Shack, and Panera,” Whaley says. “But I still wanted to meet Warren Thompson, the CEO of Thompson Hospitality. From what I knew, we had much in common and even looked alike. I knew he believed in growth through acquisition, so I had an idea.”
Whaley contacted the vice president of human resources for Thompson Hospitality. His firm, AY Direct Hire, was retained to recruit restaurant staff. Through that work, he met Warren Thompson, and suggested he meet with a local restaurant chain that had 14 locations and done $50 million in revenue the year prior. At the end of that meeting, Whaley asked Thompson if there was more business development work he could do. Thompson arranged for Whaley to interview, and he was hired to handle business development for the company’s campus dining division.
While at Thompson, Whaley decided to invest in himself by taking Harvard Business School Online courses. He completed Organizational Leadership, Strategy Execution, and Negotiation Mastery, earning a Certificate of Specialization in Leadership and Management.
“Warren Thompson paid for two of the three courses I took,” Whaley says. “I learned a lot in Strategy Execution, but it was the hardest course of my life. My last course was Negotiation Mastery, and I use the levers I learned every single day. The courses changed my life.”
Whaley recently attended HBS Online’s annual learner conference Connext and met some of the faculty who taught his courses.
“When I realized I was assigned to Negotiation Mastery Professor Michael Wheeler’s case discussion, I flipped out,” he says. “I had a chance to talk to him after the session and I told him how impactful his program has been socially and in my career.”
Whaley adds, “I give all the credit to HBS Online for investing so much time from faculty and staff to create a world-class program. I dipped into my savings to take the courses and I really see the rewards.”
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Whaley is now back to his roots, serving as the regional vice president of sales at Whitsons Culinary Group, a K-12 dining service organization.
“I was that kid, and now I’m back in the school cafeteria business,” Whaley says.
Outside of work, he spends time with his three kids on the nonprofit they created, Food for the Holidays, which provides meals to families in need. It started as a holiday program, but they now partner with Whole Foods to provide food two times per week to 400 people.
“Our kids help pack the food at the end of every week because these people may not get food over the weekend,” Whaley says.
Whaley notes his “itch is scratched” with his nonprofit, which he plans to expand.
“Education is part of my life and has led to all of my career pivots,” Whaley says. “I’m not the smartest guy, but my grit and determination are my greatest skills. In addition to continuing my education, I plan to continue leveraging my natural talents. Within five years, I’d like to lead a team. In 10 years, I’d like to be CEO and take a company public.”
If you’d like to continue your education, make connections, and hone your business skills, Harvard Business School Online offers a variety of certificate courses on vital business topics, including strategy, entrepreneurship, and leadership and management.