Ole Cup

The Ole Cup is an annual student entrepreneurial competition conceived by Brad Cleveland ‘82. The competition, which is open to all St. Olaf students, is on Saturday, April 25th, 2020 9:00 a.m.-12:30 p.m. The grand prize winner(s) receives $10,000, and is paired with alumni and parent mentors to receive pro-bono legal, accounting, HR, and other services to support the business for up to one year. The second prize winner(s) receives $5,000 and the third place, $3,000. There will be an additional award of $5,000 for the best social venture. 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.


Ole Cup 2020 – Information & Requirements

Student teams must submit an Executive Summary by Sunday, March 15, 2020, and a Business Plan by April 5, 2020.

You must also attend the following:

  • One Business Plan Basics session, one Business Plan Review Session, OR 1-1 with Margaret Bransford prior to April 1 2020. Business Plan sessions are offered throughout February and March.
  • At least one Pitch Readiness session during the month of April.

Margaret Bransford, the Associate Director for Entrepreneurship and Outreach, provides 1-1 coaching and group programs to help students develop and refine their business ideas. From ideation, to market realities, to financial forecasting, she is here to help students as they prepare to pitch their ideas.

View 2014201520162017, 2018, and 2019 participants, including winners and judges.

  1. Any individual or group of First-Year, Sophomore, Junior, or Senior students enrolled at St. Olaf at the time of application.
  2. Applicants must be in good academic standing and have maintained professional conduct as a student*
  3. At least one member on the team must be between the ages of 19-30 on April 25, 2020.
  4. 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.

Application Process

1. Executive Summary (This is your elevator pitch) – Due in Handshake by the end of the day Sunday, March 15, 2020. (100 word max).

2. Business Plan – Student(s) should complete a high level business plan by April 5, 2020. Submit through Handshake 

St Olaf Entrepreneurship Basic Business Plan Template

3. Meet with a coach – Margaret Bransford after submitting the Executive Summary to review the Final Business Plan/Pitch before April 5. (REQUIRED)

4. Pitch – Student(s) will pitch their business during the Ole Cup on Saturday, April 25th, 2019.

Use this tutorial on presentation fundamentals for additional guidance.

If you have any questions, please contact Margaret Bransford, bransf1@stolaf.edu or stop by her office in RML 474 (office hours: 3-5pm Wednesdays).


After the Ole Cup, students receive support and guidance on the next steps for the business idea, win or lose.