At fifth annual Ole Cup competition, style reigns

Piper Center for Vocation and Career Director Leslie Moore ’77 (left) at the Ole Cup competition with first-place winner Shaquille Brown ’19 (center) and second-place winner Patrik Stefek ’18.

The winners of the fifth annual Ole Cup, the student entrepreneurial competition at St. Olaf College, all had one thing in common: style.

Shaquille Brown ’19 took first place, and a prize of $10,000, for her plan to launch a line of stylish designer lunch bags for the modern career woman. Her business, Willinda Constantine, “was borne out of a desire to provide career women with affordable, luxury lunch bag options.”

Patrik Stefek ’18 took second place, and a prize of $5,000, for his plan for Texima Group, an online marketplace, merchant, and distributor of high-quality, affordable, and customer-specific suspenders.

Wael Awada ’19 and Kenzi Laumann ’19 took third place, and a prize of $3,000, for Gay Apparel, a hand-embroidered clothing brand made by LGBTQ people for LGBTQ people. A percentage of Gay Apparel’s revenue goes to LGBTQ empowerment organizations.

The winners were among the 11 St. Olaf students/teams pitched their plans to a panel of entrepreneurs, business executives, and former recipients of the award.

An additional $5,000 is awarded to the student with the top social venture — this year that was Anna Wolle ’18. Her organization Teranga Strings, is a music program in Dakar, Senegal, that allows students of any age to study violin.

The Ole Cup was conceived by the late Brad Cleveland ‘82, CEO of Proto Labs, who wanted St. Olaf students to realize how much fun it can be to be an entrepreneur. In its first five years, it has helped launch successful businesses like JonnyPops and the Ole Thrift Shop.

Each year the winner of the Ole Cup automatically qualifies for the semi-final round of the Minnesota Cup student division. Brown will pitch her plan for Willinda Constantine alongside entrepreneurs from across the state.

To prepare student entrepreneurs for the Ole Cup, Piper Center for Vocation and Career Associate Director for Entrepreneurship Roberto Zayas provides business plan advising and feedback on students’ pitches. He connects teams to a loyal network of Ole entrepreneurs and investors — like Tina Rexing ’95, owner of T-Rex Cookie Co., who served as the keynote speaker at this year’s Ole Cup — as well as service providers in accounting, finance, legal, marketing, payroll, and human resources.

In addition to being a great experience for students, the Ole Cup is also a fun event to watch. Take a moment to watch the archived stream of the competition below.