Venture firm in listed AI tools
Gaingels
Gaingels has backed 4 companies behind 4 listings on Anchor Terminal.
Companies on Anchor Terminal
Ashby, Inc. Series D, July 2025
FreshBooks Series E, August 2021
Gladia Series A, October 2024
Source gladia.io/blog/…
Middesk, Inc. Series B, July 2022
Source middesk.com/blog/…
Where they invest
Recruiting & applicant tracking 1 Accounting & invoicing 1 Speech-to-text 1 Identity & business verification 1
Founders they backed
- Benjamin Encz Ashby, Inc.
- Abhik Pramanik Ashby, Inc.
- Mike McDerment FreshBooks
- Jean-Louis Quéguiner Gladia
- Kyle Mack Middesk, Inc.
- Kurt Ruppel Middesk, Inc.
Questions
Which AI tools has Gaingels invested in?
Anchor Terminal lists Ashby, Inc., FreshBooks, Gladia and Middesk, Inc. backed by Gaingels.
How are Gaingels's companies graded?
On Anchor Terminal's benchmark, Ashby (C, 61.4), FreshBooks API (E, 45.5), Gladia Speech-to-Text API + MCP (B, 69.6) and Middesk (C, 59.1).
Investors are named from the companies' own announcements, the investors' own pages, Y Combinator's company pages, public filings and news reports of a round, each with its source and the date it was researched. An investor isn't a sign of quality, and nobody can pay to be listed or to change a grade. To correct something or have a page removed, write to privacy@anchorterminal.com.