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, will be delivered in a live, online virtual format for 2021. Students will submit a video pitch, and must be available for live, virtual judging and feedback on Saturday, April 24th, 2021 beginning at 9:30 a.m. until 2:15pm. Tune in to the event live stream here.

First prize: $10,000
Second prize: $5,000
Third prize: $3,000
Social Impact prize: $5,000

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.

New this year – the Ole Cup Social Impact winner automatically qualifies for the final round of the Fowler Global Social Innovation Challenge, where they will compete with teams from all over the globe for up to $50,000 in funding.

This year, the Northfield Enterprise Center will be offering a Northfield community prize of $500 to the Ole Cup team of their choice. We are pleased that the community of Northfield is supporting our student entrepreneurs!


Ole Cup 2021 – Information & Requirements

Get started by watching this video introduction to entrepreneurial resources at St. Olaf.

Student teams have access to 1-1 coaching to take their idea from concept to plan and pitch. Up to ten teams are chosen to participate in the Ole Cup finals. There are three application deadlines that serve as milestones to guide teams through the process:

Sunday, February 28, 2021:  Executive Summary deadline. The Executive Summary is a high-level description of your company (elevator pitch). It should be no longer than 100 words. Please submit via PDF. It should include a basic description of your business idea, such as a problem statement and value proposition. Submit your application through Handshake.

Tip: 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. 

Sunday, March 28, 2021: Business Plan deadline. The Business Plan should be between 10-15 pages and include: an overview of you product idea/venture, market analysis, business model, marketing plan, team, operations plan, and basic financial information, include an estimate of start-up costs and a 1-3 year proforma. Don’t be intimidated -there is coaching available to help you develop this!

Tip: Use the Business Plan Basics template as a guide.

Thursday, April 15, 2021: Video Pitch Submission deadline. The video pitch is five minutes long, and provides a high-level summary of your business idea. There is extensive coaching on pitch development throughout the three weeks preceding the submission deadline.

Tip: Watch previous Ole Cup competitions to get a sense of how to develop your pitch.

Teams must be available to attend the live, virtual judging event to answer questions and receive feedback on Saturday, April 24, 2021.

It is also highly recommended that you take advantage of the following resources:

  • [Link Coming Soon!] – these video prep sessions will introduce you to the concepts of venture development and the business plan, give you insights into the competition from previous years’ alumni, and point you to additional resources.
  • At least one 1-1 meeting with Margaret Bransford, prior to March 21. These sessions are currently available remotely and can be accessed via Handshake or by emailing Margaret with your availability.
  • At least two half-hour Pitch Readiness sessions during the month of April. These will be available remotely via video between the March 28 and April 15 deadlines.

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 previous Ole Cup competitions, and learn more about past participants, including winners and judges: 2014201520162017, 2018, 2019 and 2020.

Use this tutorial on presentation fundamentals for additional guidance.

  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, 2021.
  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.


After the Ole Cup, students receive support and guidance on the next steps for the business idea, win or lose. The winner of Ole Cup proceeds to the semi-finals of the MN Cup Student Division. The Social Impact winner proceeds to the finals of the Fowler Global Social Innovation Challenge.


If you have any questions, please contact Margaret Bransford, bransf1@stolaf.edu.