# Gaingels

> Gaingels's investments in AI tools on Anchor Terminal, Ashby, Inc., FreshBooks, Gladia and Middesk, Inc., with each listing's grade and the founders behind it.

- Canonical: https://www.anchorterminal.com/investors/gaingels/
- Markdown: https://www.anchorterminal.com/investors/gaingels/index.md (~750 tokens)
- Slim: https://www.anchorterminal.com/investors/gaingels/index.min.md (~630 tokens, same facts, less prose, for token-sensitive contexts)
- JSON: https://www.anchorterminal.com/investors/gaingels/index.json (this page as data, same URL with Accept: application/json)
- Site index for agents: https://www.anchorterminal.com/llms.txt (full text: https://www.anchorterminal.com/llms-full.txt)
- API: https://www.anchorterminal.com/api/v1/index.json
- MCP: https://www.anchorterminal.com/mcp (the whole catalogue as tools, no key)
- Licence: CC BY 4.0, credit Anchor Terminal and link this page (https://www.anchorterminal.com/terms/#data)
- Updated: 2026-10-28

Venture firm.

Website: https://gaingels.com

## Companies on Anchor Terminal

- **Ashby, Inc.**, Series D, July 2025
  - [Ashby](https://www.anchorterminal.com/tools/ashby.md), graded C, 61.4/100
  - Source: https://www.ashbyhq.com/blog/culture/series-d
- **FreshBooks**, Series E, August 2021
  - [FreshBooks API](https://www.anchorterminal.com/tools/freshbooks.md), graded E, 45.5/100
  - Source: https://www.freshbooks.com/press/releases/freshbooks-secures-130m-in-funding-another-unicorn-is-born
- **Gladia**, Series A, October 2024
  - [Gladia Speech-to-Text API + MCP](https://www.anchorterminal.com/tools/gladia-stt.md), graded B, 69.6/100
  - Source: https://www.gladia.io/blog/road-to-real-time-audio-ai-series-a
- **Middesk, Inc.**, Series B, July 2022
  - [Middesk](https://www.anchorterminal.com/tools/middesk.md), graded C, 59.1/100
  - Source: https://www.middesk.com/blog/announcing-our-57m-series-b

## Where they invest

- Recruiting & applicant tracking, 1
- Accounting & invoicing, 1
- Speech-to-text, 1
- Identity & business verification, 1

## Founders they backed

- [Benjamin Encz](https://www.anchorterminal.com/people/benjamin-encz/), Ashby, Inc.
- [Abhik Pramanik](https://www.anchorterminal.com/people/abhik-pramanik/), Ashby, Inc.
- [Mike McDerment](https://www.anchorterminal.com/people/mike-mcderment/), FreshBooks
- [Jean-Louis Quéguiner](https://www.anchorterminal.com/people/jean-louis-queguiner/), Gladia
- [Kyle Mack](https://www.anchorterminal.com/people/kyle-mack/), Middesk, Inc.
- [Kurt Ruppel](https://www.anchorterminal.com/people/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. 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.

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