Ole Cup Process and Rules

Summary

This chapter is your complete reference for the Ole Cup competition itself — the application process, eligibility requirements, mentoring phase, judging criteria, prize structure, and the pathway to the Minnesota Cup. You will map every chapter of this book to a specific part of the application or judging rubric so that working through the textbook is working through your Ole Cup prep. By the end of this chapter, you will have a competition calendar with personal deadlines for every deliverable.

Concepts Covered

This chapter covers the following 8 concepts from the learning graph:

1. Ole Cup Competition
2. Ole Cup Application
3. Ole Cup Eligibility
4. Ole Cup Timeline
5. Ole Cup Mentoring Phase
6. Ole Cup Judging Criteria
7. People's Choice Award
8. Minnesota Cup

Prerequisites

This chapter builds on concepts from:

• Chapter 11: The Pitch Deck

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Every year, the same scene: a student who has been working on their venture quietly for months — refining the idea, talking to customers, iterating the deck — walks up to the Piper Center desk in late January to ask about the Ole Cup application.

The application deadline is February 15.

They have three weeks.

They make it. (Usually.) But those three weeks look very different from the founders who have been building toward competition day since September — who have already done their customer discovery, completed their canvas, run their MVP experiments, and practiced their pitch enough times that the story flows without notes.

This chapter exists so that you are the second kind of student. It maps the Ole Cup timeline, the application requirements, the judging criteria, and the prize structure onto a concrete personal calendar — so that by the time applications open in December, you are not starting from zero.

Chapter 12: The competition is the goal, and this is the map

Everything in this book has been building toward a single event: Ole Cup competition day. This chapter tells you exactly what to expect — the dates, the criteria, the prizes, and the path beyond. By the end, you will have a personal deadline calendar that turns "someday I'll enter the Ole Cup" into a series of specific dates with specific deliverables.

The Ole Cup: What It Is and Why It Exists

The Ole Cup was founded in 2014 with a grant from Brad Cleveland '82 — CEO of Proto Labs and a firm believer that entrepreneurship should be accessible to every St. Olaf student regardless of major. Brad's founding conviction was simple: liberal arts students have exactly the skills and perspectives that ventures need, but nobody was telling them that. The Ole Cup exists to close that gap.

Since 2014:

• 150+ students have participated
• $250,000+ in prize money has been awarded
• $615,000+ in total entrepreneurial funding (prizes plus grants) has gone to students
• 20 entrepreneurship-related courses are available across disciplines

Every Ole Cup participant, winner or not, reports the same experience: the process of building toward a competitive pitch forced them to develop their idea more rigorously than they would have on their own. The competition is the curriculum.

Eligibility Requirements

The Ole Cup is open to all currently enrolled St. Olaf College students. Specifically:

• Enrolled students only: You must be enrolled at St. Olaf at the time of application and competition. Recent graduates are not eligible, but an enrolled student on a team that includes a recent graduate may still apply.
• All years and majors: First-year through senior; any major or no declared major.
• No prior funding required: You do not need to have already received a Finstad Grant or any other funding. The Ole Cup is open to teams at any stage from early ideation through active revenue generation.
• Team composition: Teams of one to four members are accepted. Solo founders may apply. Teams of two or three tend to be most competitive based on historical results, but this is not a criterion.
• No exclusive IP requirement: You can apply with an idea that is also being explored independently elsewhere. The Ole Cup does not require exclusivity.

The Competition Timeline

The Ole Cup runs on an academic year cycle. The key dates:

Phase	Date	What Happens
Applications open	December 1	Application portal goes live on the Piper Center website
Application deadline	February 15	All materials due; late applications not accepted
Semi-finalist notification	Early March	Teams accepted into the mentoring phase are notified
Mentoring phase	March through mid-April	Semi-finalists work with assigned mentors
Finalist notification	Mid-April	Teams advancing to competition day are selected
Competition day	Late April	Live pitches to judge panel; prizes awarded
Minnesota Cup opening	May	Ole Cup winners automatically qualify for the MN Cup student division

The specific dates shift slightly year to year. The Piper Center website and your assigned mentor will always have the current year's calendar. For planning purposes, treat December 1 as your "everything should be ready for review" date and February 15 as an absolute hard stop.

The Application

The Ole Cup application typically includes the following components. Requirements may vary slightly year to year — always verify the current year's requirements on the Piper Center website.

Required components:

1. Executive Summary (1–2 pages): A written description of the venture covering the problem, the solution, the target market, the business model, the team, and the current stage of development. The executive summary is the first filter; applications that do not clearly and specifically answer all six components are typically not advanced.

2. Pitch Deck (PDF): Your six-slide deck from Chapter 11 (or an early version of it), submitted as a PDF. Judges reviewing applications do not watch live pitches at this stage — the deck must stand on its own.

3. One-Minute Video Pitch: A short video introduction of the team and the venture. This is assessed for communication ability and founder conviction, not production quality. A phone recording in good light with clear audio is entirely appropriate.

4. Financial Projection (optional but recommended): A one-page financial model showing first-year revenue, costs, and key unit economics. Teams that include a thoughtful financial projection typically score higher in the review process.

The application review panel includes Piper Center staff, faculty advisors, and alumni judges. They are looking for: problem specificity, evidence of customer discovery, plausibility of the business model, team complementarity, and — most importantly — founder conviction and authenticity.

Start with the executive summary, not the deck

The executive summary forces you to explain your venture in prose, without the visual crutch of slides. If you cannot write a clear, specific executive summary, your pitch deck has gaps you have not noticed yet. Write the summary first; the deck clarity usually improves as a result.

The Mentoring Phase

Semi-finalists are assigned one or more mentors from the St. Olaf alumni and business community. The mentoring phase runs from early March through mid-April — approximately six weeks of structured interaction between your team and your assigned mentors.

What the mentoring phase is:

• A scheduled series of one-hour conversations with your mentor(s)
• An opportunity to test your assumptions with experienced founders and operators
• A chance to refine your pitch based on real feedback from people who have built companies
• Access to the broader Piper Center network of resources (DiSCO, Creative Makerspace, Finstad Grants)

What the mentoring phase is not:

• A guarantee that your mentor will validate your idea
• A passive experience where mentors do the work for you
• A reason to stop customer discovery and experimentation

The teams that make the most of the mentoring phase come prepared to each session with a specific question, a specific update on what they have built or tested since the last session, and specific feedback they are seeking. Mentors who are asked "what do you think of our idea?" give less useful feedback than mentors who are asked "we tried X and learned Y — do you think the implication is Z, or are we drawing the wrong conclusion?"

Judging Criteria

The Ole Cup judging rubric evaluates each team across five dimensions. Understanding these dimensions is identical to understanding what to build toward in every chapter of this book.

Criterion	What Judges Assess	Chapter That Prepares You
Problem and Opportunity	Is the problem real, specific, and significant? Is the market opportunity credible?	Ch. 3, 9
Solution and Value Proposition	Does the solution directly address the problem? Is the value proposition clear and differentiated?	Ch. 4, 10
Business Model and Viability	Is there a plausible path to financial sustainability? Are the unit economics coherent?	Ch. 8, 9
Traction and Validation	Is there evidence that real customers want this? Have the founders tested their assumptions?	Ch. 5, 4
Team	Does the team have the complementary skills to execute? Are founders convincing in their conviction and knowledge?	Ch. 7, 11

Judges score each criterion on a 1–5 scale. The total is out of 25 points, though the exact weighting may vary year to year. The Social Impact Prize has its own additional scoring rubric (theory of change, impact measurement plan, financial sustainability for mission) that supplements the main criteria for eligible ventures.

Prize Structure

The Ole Cup offers the following prizes, totaling up to $35,000 in available awards:

Prize	Amount	Criteria
First Place	$10,000	Highest overall score
Second Place	$7,500	Second-highest overall score
Third Place	$5,000	Third-highest overall score
Social Impact Prize	$7,500	Best social/environmental impact alongside financial sustainability
People's Choice Award	$3,000	Audience vote during or after presentations

A single venture can win multiple prizes — for example, a social venture could win First Place and the Social Impact Prize simultaneously, earning $17,500. The People's Choice Award is determined by audience voting, which means that campus community building before competition day (exactly the word-of-mouth and campus marketing from Chapter 10) has direct financial value.

The People's Choice Award in particular rewards ventures that have built genuine community awareness and enthusiasm before competition day. A team that has tabled at Buntrock, gotten Manitou Messenger coverage, and built an audience of invested supporters will mobilize more audience votes than a team that is new to most attendees.

The Minnesota Cup Pathway

All Ole Cup prize winners automatically qualify for the Minnesota Cup student division — the state's largest business competition, hosted annually by the University of Minnesota Carlson School of Management.

The Minnesota Cup provides:

• Connections to the broader Twin Cities entrepreneurship ecosystem (Lunar Startups, Bunker Labs, Impact Hub)
• Access to additional prize money (the student division awards up to $10,000)
• Mentorship from a larger and more diverse professional network
• Visibility with potential investors and partners beyond the St. Olaf community

For ventures with genuine commercial or social potential, the Minnesota Cup pathway is not a consolation prize — it is the first step in a much larger journey. Foodle (Jakob Otten '19) and other Ole Cup teams have used the Minnesota Cup as a launchpad for further competition, national accelerator applications, and early investment conversations.

The Ole Cup is the beginning of the story, not the end

Every successful Ole Cup alumnus says the same thing in retrospect: winning (or even competing) was not the moment that mattered most. The preparation — the customer conversations, the experiments, the team formation, the pitch refinement — was the education. The prize was a signal that the education was working.

Your Personal Competition Calendar

The table below maps each chapter of this book to the Ole Cup application or judging criterion it prepares — and assigns a suggested completion target based on the December 1 application opening and February 15 deadline.

Chapter	Delivers	Suggested Completion Target
1 — Ikigai	Personal statement "why you"	September
2 — Ideation	Three candidate ideas	September
3 — Opportunity	One validated opportunity	October
4 — Value Proposition	One-sentence value proposition, MVP concept	October
5 — MVP Thinking	Riskiest assumption + experiment design	October–November
6 — Social Ventures	Organizational model decision	October
7 — Team Formation	Team assembled, roles defined	October–November
8 — Business Model Canvas	First-draft canvas	November
9 — Financial Fundamentals	Unit economics + 6-month projection	November
10 — Marketing and Storytelling	Founder story + marketing plan	November
11 — Pitch Deck	First-draft deck, practiced 5 times	November–December
12 — Ole Cup Rules	Competition calendar complete	December
Application opens	All of the above ready for review	December 1
Application materials finalized	Executive summary + deck + video + financials	February 1–10
Application deadline	Everything submitted	February 15
13 — Ecosystem	Mentor outreach + advanced tools	During mentoring phase (March–April)
14 — Failure	Post-mortem analysis + iteration	Throughout
15 — Launch	90-day post-competition plan	Competition day +

Diagram: Ole Cup Competition Calendar

Interactive Ole Cup Competition Calendar — track your progress toward every application deadline

Type: MicroSim sim-id: ole-cup-calendar
Library: vis-timeline
Status: Specified

Learning objective: Students create a personal competition calendar by mapping chapter deliverables to target completion dates and tracking their progress. (Bloom's Taxonomy: Applying)

Canvas: 740×420px responsive, redraws on window resize events.

Timeline: A horizontal vis-timeline spanning August 1 through April 30 of the academic year. The x-axis shows months; the y-axis shows two groups:

Group 1: Key Competition Dates (fixed, read-only events): - Sep 1: "Semester begins — start building" - Dec 1: "Applications open" - Feb 15: "Application deadline" (highlighted in red) - Early March: "Semi-finalist notification" - Late March–April: "Mentoring phase" - Late April: "Competition day" (highlighted in gold) - May: "Minnesota Cup opens"

Group 2: My Deliverables (editable, student-owned items): Pre-populated with the 12 chapter deliverables from the table above, each placed at the "suggested completion target" date. Each item has: - A label (e.g., "Ch.3: One validated opportunity") - A status toggle: Not started / In progress / Complete (shown as color: red / yellow / green) - The ability to drag the item left or right on the timeline to adjust the target date.

Interaction: - Hovering any item shows a tooltip with the chapter number, the deliverable description, and the chapter this connects to in the Ole Cup judging rubric. - Clicking an item opens a small status panel: toggle the status, add a brief note ("Customer interviews done; need to finalize one-sentence VP"). - A progress bar at the bottom shows: "X of 12 deliverables complete."

Responsive design: On window resize, recalculate and redraw. At widths below 600px, switch to a vertical scrollable list of deliverables with status indicators. Minimum canvas width: 320px.

Accessibility: All items are keyboard-navigable. Status changes are announced via aria-live. The timeline data is also available as a sortable accessible table below the canvas.

Try It

1. Build Your Personal Calendar. Using the interactive calendar above (or a spreadsheet), map the 12 chapter deliverables to specific target dates on your own academic calendar. Identify the three deliverables where you are furthest behind and write a one-paragraph catch-up plan for each.

2. Read the Application. Find the current year's Ole Cup application on the Piper Center website. Read every field and every question. For each field, identify the chapter in this book that produces the content to fill it. Note any fields that surprise you — where you expected one thing and found another.

3. Write Your Executive Summary Draft. Using the structure described above (problem, solution, target market, business model, team, current stage), write a two-page executive summary of your venture. This draft will be imperfect — that is the point. The imperfections reveal the gaps in your thinking.

4. People's Choice Strategy. Write a one-paragraph strategy for building campus community awareness before competition day. Specifically: what will you do to make sure that 50 people in the competition audience already know about your venture before they walk in? Name the specific channels and the specific actions.

Ole Cup Connection

This entire chapter is the Ole Cup connection. The most important thing it delivers is the personal competition calendar: a concrete list of what to have done, by when, so that February 15 does not arrive as a surprise. Treat the calendar as a living document — update the status of each deliverable weekly starting in September. Students who track their progress this way consistently report that they feel more prepared, make better use of their mentor time, and perform better under the pressure of competition day because the preparation has been systematic rather than frantic.

You have the full map — now you know where you are going

Dates, criteria, prizes, pathway — you now know exactly what the Ole Cup requires and exactly how this book prepares you for it. In Chapter 13, we go beyond the competition itself and explore the full St. Olaf entrepreneurship ecosystem: the grants, the mentors, the partner organizations, and the advanced customer discovery tools that become most powerful when you have an experienced guide helping you use them.