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Paul Cheek

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Paul Cheek is an American entrepreneur, educator, software engineer, and author. He is recognized for his contributions to innovation-driven entrepreneurship and his leadership roles at the Massachusetts Institute of Technology (MIT).

Cheek has co-founded multiple venture-backed startups, contributed to the global entrepreneurship ecosystem, and authored work on startup methodology.

Early Life and Education

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Cheek grew up in Wellesley, Massachusetts, where he developed an early interest in technology, business, and problem-solving. He attended Bentley University, where he pursued a multidisciplinary education, studying Finance, Accounting, Marketing, and Computer Information Systems. His broad academic background laid the foundation for his unique ability to bridge technical and business domains in entrepreneurial ventures.

Career

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Entrepreneurship

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Cheek is a serial technology entrepreneur with a focus on mission-driven ventures. He co-founded Oceanworks, a for-profit company with a mission to end plastic pollution, and Work Today, a venture-backed digital staffing and recruiting company. His entrepreneurial ventures have earned him recognition, including being named to Forbes 30 Under 30 in the Energy category in 2022. Forbes

MIT Involvement

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Cheek has played a significant role at MIT, where he served as Executive Director of the Martin Trust Center for MIT Entrepreneurship and as a Senior Lecturer at the MIT Sloan School of Management. He was the institute’s first Hacker in Residence, a role created to support technical innovation and student entrepreneurship.

At MIT, he has taught and mentored thousands of students and global entrepreneurs. He is known for designing and teaching “Venture Creation Tactics,” an advanced course on startup execution, and for leading the iconic “New Enterprises” course, one of MIT’s longest-running entrepreneurship classes.

In May 2025, Cheek stepped down from his executive role at the Trust Center to focus on new ventures, advisory roles, and public speaking, while continuing his faculty position at MIT.

Speaking and Thought Leadership

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Cheek is a frequent keynote speaker at conferences, universities, and corporate events, where he presents on the future of entrepreneurship, innovation ecosystems, and artificial intelligence. He is a leading advocate for a new model of company creation centered on AI-Driven Enterprises (AIDEs)—businesses operated autonomously by generative AI agents with minimal human intervention.

He coined the term AIDE to describe this emerging category, positioning it alongside small and medium-sized enterprises (SMEs) and innovation-driven enterprises (IDEs). His work explores how AI is lowering the barriers to entrepreneurship by reducing capital requirements and operational complexity, enabling the creation of scalable companies with fewer resources.[1]

Through his writing, speaking, and advisory roles, Cheek promotes a vision of entrepreneurship where structure, automation, and agentic systems unlock new economic opportunities. He is a frequent contributor to discussions on AI policy, automation ethics, and the intersection of technology and entrepreneurial education.

Publications

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Recognition

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  • Named to Forbes 30 Under 30 list in the Energy category in 2022. Forbes
  • Featured in publications including Forbes, Entrepreneur, and Inc Magazine. Paul Cheek
  • Monsoon Prize
    • The Monsoon Prize is an annual award presented by the Martin Trust Center for MIT Entrepreneurship. It recognizes outstanding entrepreneurial efforts focused on addressing critical challenges in emerging markets. The prize is awarded to an MIT student or team developing innovative solutions in areas such as healthcare, energy, education, and water access within underserved communities. The Monsoon Prize includes a $2,500 cash award and is part of the broader MIT Entrepreneurship Awards program, which supports innovation and impact-driven ventures launched by members of the MIT community.
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Sources:

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References

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  1. ^ "AI-Driven Enterprises: How AI is Redefining Innovation-Driven Enterprises". Paul Cheek. Retrieved 2025-05-14.