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  "markdown": "Venture firm.\n\nWebsite: https://gaingels.com\n\n## Companies on Anchor Terminal\n\n- **Ashby, Inc.**, Series D, July 2025\n  - [Ashby](https://www.anchorterminal.com/tools/ashby.md), graded C, 61.4/100\n  - Source: https://www.ashbyhq.com/blog/culture/series-d\n- **FreshBooks**, Series E, August 2021\n  - [FreshBooks API](https://www.anchorterminal.com/tools/freshbooks.md), graded E, 45.5/100\n  - Source: https://www.freshbooks.com/press/releases/freshbooks-secures-130m-in-funding-another-unicorn-is-born\n- **Gladia**, Series A, October 2024\n  - [Gladia Speech-to-Text API + MCP](https://www.anchorterminal.com/tools/gladia-stt.md), graded B, 69.6/100\n  - Source: https://www.gladia.io/blog/road-to-real-time-audio-ai-series-a\n- **Middesk, Inc.**, Series B, July 2022\n  - [Middesk](https://www.anchorterminal.com/tools/middesk.md), graded C, 59.1/100\n  - Source: https://www.middesk.com/blog/announcing-our-57m-series-b\n\n## Where they invest\n\n- Recruiting \u0026 applicant tracking, 1\n- Accounting \u0026 invoicing, 1\n- Speech-to-text, 1\n- Identity \u0026 business verification, 1\n\n## Founders they backed\n\n- [Benjamin Encz](https://www.anchorterminal.com/people/benjamin-encz/), Ashby, Inc.\n- [Abhik Pramanik](https://www.anchorterminal.com/people/abhik-pramanik/), Ashby, Inc.\n- [Mike McDerment](https://www.anchorterminal.com/people/mike-mcderment/), FreshBooks\n- [Jean-Louis Quéguiner](https://www.anchorterminal.com/people/jean-louis-queguiner/), Gladia\n- [Kyle Mack](https://www.anchorterminal.com/people/kyle-mack/), Middesk, Inc.\n- [Kurt Ruppel](https://www.anchorterminal.com/people/kurt-ruppel/), Middesk, Inc.\n\n## Questions\n\n### Which AI tools has Gaingels invested in?\n\nAnchor Terminal lists Ashby, Inc., FreshBooks, Gladia and Middesk, Inc. backed by Gaingels.\n\n### How are Gaingels's companies graded?\n\nOn 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).\n\nInvestors 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. 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.\n",
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