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Course Description

Title

Ole Cup Entrepreneurship: A Liberal Arts Guide to the St. Olaf Pitch Competition

Audience

This course is designed for all St. Olaf College students regardless of major — music, art, studio art, theater, biology, chemistry, computer science, mathematics, history, political science, religion, or any other field of study. No prior business coursework is required.

The ideal reader is a curious student who has an idea — or wants to find one — and is willing to explore how their passions, skills, and sense of purpose can become the foundation of a venture worth pitching. Students who have completed any single course in any discipline (first-years through seniors) have the prerequisite background needed.

The textbook is specifically built to support participation in the Ole Cup, St. Olaf's annual Shark Tank-style pitch competition hosted by the Piper Center for Vocation and Career, with prize money ranging from $3,000 to $10,000 and automatic qualification for the Minnesota Cup student division.

Prerequisites

Students need only:

  • Curiosity — a willingness to explore ideas without knowing where they will lead
  • Willingness to share ideas — comfort pitching rough concepts to peers for feedback
  • Basic written and verbal communication — the ability to write a paragraph and speak for two minutes
  • No prior business, economics, finance, or entrepreneurship coursework is assumed or required

Topics

  1. Ikigai and Self-Discovery — The Japanese concept of Ikigai ("reason for being") as a framework for entrepreneurship. The four-circle Venn diagram: What You Love, What You Are Good At, What the World Needs, What You Can Be Paid For. Intersections: Passion, Mission, Vocation, Profession. Finding your personal Ikigai as the seed of a venture idea.

  2. Ideation Across the Liberal Arts — Generating business and social venture ideas from music, visual arts, theater, writing, science, history, religion, philosophy, and athletics. Cross-disciplinary creativity techniques: SCAMPER, random association, problem inversion, user empathy mapping. The liberal arts advantage in entrepreneurship.

  3. Recognizing Opportunity — The difference between an idea and an opportunity. Customer pain points, underserved markets, and social gaps. Trends and signal-reading: demographic shifts, technology waves, cultural movements, regulatory changes. The opportunity evaluation matrix.

  4. Value Propositions — What problem does your venture solve, and for whom? Crafting a clear, testable value proposition. The Value Proposition Canvas. Distinguishing features from benefits. The "Mom Test": how to talk to potential customers without misleading yourself.

  5. Minimum Viable Product (MVP) Thinking — Building the smallest thing that tests your most important assumption. Paper prototypes, wireframes, and landing pages. The Build-Measure-Learn cycle. Running low-cost experiments before writing a line of code or spending a dollar.

  6. Social Ventures and Impact — The spectrum from pure nonprofit to pure for-profit and the hybrid social enterprise models in between. B-Corp certification, benefit corporations, and co-ops. Measuring social impact alongside financial return. The Ole Cup Social Impact Prize and how social ventures are judged.

  7. Team Formation and Roles — Why diverse teams outperform solo founders. Identifying complementary skills: the builder, the seller, and the visionary. How to pitch your idea to potential co-founders. Conflict and co-founder agreements. Team dynamics in a college context.

  8. Business Model Canvas — The nine building blocks: Customer Segments, Value Propositions, Channels, Customer Relationships, Revenue Streams, Key Resources, Key Activities, Key Partnerships, Cost Structure. Completing a canvas for your own venture. Iterating the canvas as assumptions are tested.

  9. Financial Fundamentals for Founders — Revenue models: product sales, subscriptions, marketplaces, licensing, freemium, services. Unit economics: customer acquisition cost (CAC), lifetime value (LTV), gross margin. A simple financial projection for a student venture. Why profitability matters even when you are starting small.

  10. Marketing and Storytelling — How to tell your venture's story in a way that resonates. The hero's journey applied to entrepreneurship. Social media, word-of-mouth, and campus community channels. Brand identity on a zero budget. Early adopters versus the mass market.

  11. The Pitch Deck — Structure of a winning pitch: Problem, Solution, Market, Traction, Team, Ask. Slide design principles: one idea per slide, data over decoration, visuals over text. Delivering a pitch under time pressure. Handling tough questions from judges. Video pitches versus live pitches.

  12. Ole Cup Process and Rules — Full Ole Cup competition timeline (application, mentoring phase, competition day). Eligibility requirements. Prize structure: $10,000 first prize, $7,500 second prize, $5,000 third prize, $7,500 social impact prize, $3,000 People's Choice. Judging criteria. The pathway from Ole Cup to Minnesota Cup.

  13. Mentorship and the St. Olaf Entrepreneurship Ecosystem — The Piper Center for Vocation and Career. The Finstad Entrepreneurial Grant program. Svoboda Scholars, Mayo Innovation Scholars, Norway Innovation Scholars. The Creative Makerspace and DiSCO digital scholarship center. Partner organizations: Lunar Startups, Bunker Labs, Minnesota Cup, Mayo Clinic, Fueled Collective, Impact Hub.

  14. Learning from Failure and Iteration — Why most first ideas fail and why that is the point. The pivot: real examples from Ole Cup history. Psychological safety and the growth mindset. Post-mortem analysis. How St. Olaf liberal arts training — critical thinking, writing, rhetoric — becomes a competitive advantage when things go wrong.

  15. From Pitch to Launch — What happens after you win (or don't). Next steps: prototyping, customer discovery, forming an LLC, applying for grants, finding early revenue. Ole Cup alumni success stories: JonnyPops, The Kombucha Shop (featured on Shark Tank), Netless Catch, Vasikana Vedu, Elimisha Kakuma, Foodle (Hult Prize global finalist).

Topics NOT Covered

This course does NOT cover:

  • Advanced corporate finance, valuation, or investment banking
  • Intellectual property law, patent filing, or trademark registration
  • Securities law, equity financing structures, or term sheets
  • MBA-level operations management or supply chain optimization
  • General management theory or organizational behavior at scale
  • Coding, software engineering, or technical product development
  • Macroeconomics or economic policy analysis
  • Nonprofit administration or grant writing beyond an introductory level

Learning Outcomes

By the end of this book, the reader will be able to:

  • Remember: List the four overlapping circles of the Ikigai Venn diagram and name the four intersection zones (Passion, Mission, Vocation, Profession).
  • Remember: Recall the nine building blocks of the Business Model Canvas and the order in which they are typically completed.

  • Remember: State the Ole Cup prize amounts, application deadline, competition date, and eligibility requirements, including the Minnesota Cup qualification pathway.

  • Understand: Explain how the liberal arts — music, art, science, humanities — provide an entrepreneurial advantage; describe what distinguishes a social venture from a for-profit startup; and interpret why team diversity matters in venture creation.

  • Apply: Complete a personal Ikigai diagram to identify a venture idea; fill in a Business Model Canvas for a proposed venture; and construct a five-minute pitch deck using the Problem-Solution-Market-Traction-Team-Ask structure.

  • Analyze: Evaluate a business idea using the Opportunity Evaluation Matrix, the Value Proposition Canvas, and basic unit economics (CAC, LTV, gross margin); identify the riskiest assumption in a proposed venture and design a minimum viable experiment to test it; and conduct a basic competitive landscape analysis by mapping competitors across two dimensions to identify underserved white-space opportunities.

  • Evaluate: Critique peer pitch decks using the same rubric as Ole Cup judges; assess whether a venture idea is better suited to a for-profit, nonprofit, or hybrid social enterprise model; and judge the credibility and scalability of a proposed revenue model.

  • Create: Develop an original venture concept rooted in personal Ikigai; build and present a complete Ole Cup-ready pitch including a pitch deck, financial projections, and a social impact statement; and recruit at least one co-founder or team member with a complementary skill set.

Connection to the Ole Cup Competition

This textbook is structured around the Ole Cup application and competition cycle:

Ole Cup Phase Chapters Covered
Ideation and self-discovery 1–3 (Ikigai, Liberal Arts Ideas, Opportunity)
Concept development 4–6 (Value Prop, MVP, Social Ventures)
Team and business model 7–9 (Team, Canvas, Financials)
Pitch preparation 10–12 (Marketing, Pitch Deck, Ole Cup Rules)
Support and ecosystem 13–14 (Mentorship, Failure)
Post-competition 15 (Launch)

Applications open December 1 and close February 15. The competition is held in late April. Students who work through this textbook before the application deadline will be well-prepared to apply and compete.

About the Ole Cup

The Ole Cup was founded in 2014 with support from the late Brad Cleveland '82, CEO of Proto Labs, who believed entrepreneurship should be accessible to every St. Olaf student regardless of major. Since its founding:

  • 150+ students have participated
  • $250,000+ in prize money has been awarded
  • $615,000+ in total entrepreneurial funding (including grants) has gone to students
  • 20 entrepreneurship-related courses are available across disciplines
  • Notable alumni ventures include JonnyPops (multi-million dollar company, Target/Costco), The Kombucha Shop (Shark Tank), Netless Catch (acquired), Foodle (Hult Prize global finalist), and Vasikana Vedu (active social venture in sub-Saharan Africa)

About Ikigai

Ikigai (生き甲斐) is a Japanese concept combining iki ("life") and gai ("value" or "worth") — roughly "that which makes life worth living." In its Western entrepreneurship adaptation, it is visualized as a four-circle Venn diagram whose overlapping regions describe the territory where a fulfilling and sustainable venture can be found:

          What You LOVE
               ↕
    Passion ← ● → Mission
               ↕
  What You    IKIGAI    What the
Are GOOD At ← ● →  World NEEDS
               ↕
   Vocation ← ● → Profession
               ↕
     What You Can Be PAID FOR

The four intersections:

Intersection Contains
Love + Good At Passion — joy without income
Good At + Paid For Profession — income without meaning
Paid For + World Needs Vocation — service without joy
World Needs + Love Mission — purpose without income
All four Ikigai — the entrepreneurial sweet spot

This framework is used throughout the book as the primary lens for idea generation, team role identification, and venture evaluation.