Driving Alpha: Recycling Relationships With Matthew Greenfield

Driving Alpha

Matthew Greenfield is a Managing Partner at Rethink Education, a venture capital firm dedicated to innovative educational technology. He holds multiple board seats, including at SNHU and BrightBytes, and has co-founded several successful technology companies, such as near-unicorn Rethink First. An accomplished educator and thought leader with a BA, MA, and PhD from Yale, he is former professor at Bowdoin College and the City University of New York.

Episode Chapters

(00:00) Introduction

(01:57) How familial influences shaped Matthew Greenfield's passion and direction in venture capital

(02:30) The impact of female venture partners in Matt’s father’s VC journey

(06:04) How Matt leveraged his background for Rethink Education's mission

(06:42) The importance of relationship-building for venture capital investments

(09:27) Matt illustrates the power of strategic advice and networking through Rethink First’s success story

(11:08) The key to being a successful VC: recycling people

(16:50) How to be a good giver without letting it overwhelm you

(18:45) Adapting an open-minded, unbiased approach to discovering innovation

(23:37) The intersection of product-market fit, addressing genuine human needs, and venture capital success

In this episode…

In the fast-paced world of startups and funding, maintaining and rejuvenating relationships can be as valuable as the capital itself. This cyclical nature of relationships helps VCs stay connected with past successes and ensures they remain relevant in an ever-evolving market. How can you leverage relationships in the venture capital ecosystem to achieve outsized investment returns?

Matthew Greenfield, an ex-professor turned venture capital partner, shares how strategic relationships, mentorship, and candid guidance have shaped his approach to nurturing successful enterprises. Highlighting the importance of targeting real human problems for venture growth, Matt emphasizes assisting aspiring technologists and executives while being open to innovation from unexpected sources. Whether reconnecting with a successful founder for a new project or leveraging an old network to discover the next big idea, recycling relationships is a powerful tool for long-term success in the venture capital landscape. Matt’s reflections underscore the power of embracing innovation from all corners and honest feedback's transformative impact on founders and investors alike.

In this episode of the Driving Alpha Podcast, Brian Smiga chats with Matthew Greenfield, Managing Partner at Rethink Education, about shaping the future of education and venture success. Matt dives into his transition from academia to venture capital, the importance of building a diverse network of investors, and how to strengthen trust through constructive feedback to entrepreneurs. He also explores the concept of “thrifty recycling” and the benefits of CRMs for tracking and nurturing connections.