Matthew Greenfield – Startup Investor Profile

Matthew Greenfield is the Managing Partner at Rethink Education, focusing on investing in educational technology. Rethink Education’s investment thesis for 2021 highlights the significant global spending on edtech. Their investment focus areas include K-12 and higher education, with a preference for software, edtech, and TMT sectors. Greenfield leads seed investments ranging from $250k to $750k, targeting early-stage companies in education. Geographically, Rethink Education primarily invests in the United States. Previous investments by Greenfield at Rethink Education demonstrate a commitment to impacting education positively. The investment check size typically ranges from 100-500 million dollars. Partnership and collaboration styles reflect a desire to bring new approaches to education through a mission-driven, innovative, and scalable approach.

Location: White Plains, NY

Country: Australia

Investment Regions: EU, NA

Investment Stages: pre-seed, seed

Website:

AI Reasoning: I found Rethink Education’s October 15, 2025 newsletter stating they completed three new investments in the months prior to that date: Flourish Schools (pre-seed), Rallyboard (pre-seed), and a stealth early learning platform. These investments occurred within the past 6 months from the reference date; the most recent known investments are in Q3-Q4 2025, which is less than 6 months ago. One startup invested: Flourish Schools. Therefore the appropriate tag is very-active.

Low Activity – Only known angel investments more than 12 months ago.

Active – Known angel investments between the last 12 and 6 months.

Very Active – Known angel investments in the last 6 months.