Glasswing Ventures
Glasswing Ventures is a first-capital-in venture capital firm dedicated to investing in startups applying AI and frontier technology to enterprise and cybersecurity markets. The firm was founded by visionary partners with decades of experience in these markets, a disciplined investment approach, and a strong track record of industry-leading returns. Glasswing leverages its deep domain expertise and world-leading advisory councils to invest in exceptional founders who transform markets and revolutionize industries. Glasswing Ventures was founded in 2016 and is headquartered in Boston, Massachusetts, USA. Per Crunchbase, Glasswing Ventures has made 88 investments, 41 as lead investor across 56 portfolio companies, with 12 exits.
Investing activity
Glasswing Ventures has made 88 investments according to Crunchbase across 56 portfolio companies, and has led 41 rounds and seen 12 exits.
Glasswing Ventures appears in 6 AI deals tracked by the Lounge deals desk, and led 3 of them. The rounds are mostly Seed, with a median round size of $5M and the largest at $9M. The most recent are Samepage (Seed, $4.8M, Jun 2026), Flux (Seed, $5M, Jun 2026) and Enlaye (Seed, $5M, Jun 2026).
Glasswing Ventures most often invests alongside Link Ventures, Justin Kan, Craft Ventures and Matthew Mullenweg, and the companies it backs on Lounge are mostly in AI.
Deals
Frequently asked questions about Glasswing Ventures
What AI companies has Glasswing Ventures invested in?
Glasswing Ventures's AI investments include Samepage, Flux, Enlaye, Krane, Cydelphi and GenFlux. The 6 rounds on Lounge are listed on this page with amounts, dates and co-investors.
Where is Glasswing Ventures based?
Glasswing Ventures is based in Boston, Massachusetts, United States.
What stage does Glasswing Ventures invest at?
In the rounds tracked on Lounge, Glasswing Ventures has invested at Seed, with a median round of $5M. Glasswing Ventures led 3 of those rounds.
Who does Glasswing Ventures co-invest with?
Glasswing Ventures's most frequent co-investors on Lounge are Link Ventures (2 deals), Justin Kan (1 deal), Craft Ventures (1 deal), Matthew Mullenweg (1 deal) and Freestyle Capital (1 deal).
How can founders reach Glasswing Ventures?
Founders on Lounge can see Glasswing Ventures's contact details in AI Investor Contacts (paid plans), check for a warm introduction through members who worked with the firm under Warm Paths, and add Glasswing Ventures to their Investor Pipeline to track the conversation.