Launched in 2014, the Ole Cup is an annual student entrepreneurial pitch competition open to all St. Olaf students. The Ole Cup helped launch successful businesses like JonnyPops, Whiskey Woods, the Ole Thrift Shop, and The Shop 1500. The winner of the Ole Cup is awarded a $10,000 prize to help launch their business.
Save The Date: 2025 Ole Cup | Saturday, April 26
150+
Students have participated in the Ole Cup pitch competition since 2014.
$250,000+
Dollars are awarded to student teams for the purposes of starting their venture.
Ole Cup Application Details
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December 2, 2024: Applications open for interested students. Please submit one application per team via Google Form submission.
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February 15, 2025: Application deadline. No late submissions will be accepted.
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March 1, 2025: Applicants notified via email
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March 3, 2025 – April 26, 2025: Selected teams receive mentoring, business plan support, and workshops focused on pitch deck development.
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April 26, 2025: Ole Cup Pitch Competition
Program Requirements
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Any individual or group of First-Year, Sophomore, Junior, or Senior students enrolled at St. Olaf at the time of application.
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Applicants must be in good academic standing and have maintained professional conduct as a student.*
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At least one member on the team must be between the ages of 19-30 on the day of the competition.
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The idea needs to be economically viable and it cannot violate or infringe on the copyright or intellectual property of another.
*Good academic standing means a minimum GPA of 2.0, not on academic probation or academically dismissed according to the Registrar’s Office. Professional conduct is vetted by the Dean of Students Office.
Ole Cup Origins
Brad Cleveland ’82 (1959-2016) wanted St. Olaf College students to realize how much fun it can be to be an entrepreneur— no matter what type of organization they’re interested in building. So Cleveland, former CEO of Proto Labs, helped the St. Olaf Piper Center for Vocation and Career develop and fund a new business plan competition. The Ole Cup is modeled after the highly successful Minnesota Cup and will provide several students with the resources to help turn their business idea into reality.
2024 Ole Cup Prize Winners
Watch the Recording
Preparation Resources
Use this tutorial on presentation fundamentals and the Business Plan Basics template for additional guidance. More resources and Entrepreneurship workshop recordings are available here!
The winner of the Ole Cup automatically qualifies for the semi-final round of the Minnesota Cup student division where the winner (of the student division) is awarded $30,000, and can compete for the Minnesota Cup Grand Prize of $50,000.
Meghan McMillan (she, her, hers)
Associate Director, Ole Career Launcher, Innovation and the Arts
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