Twenty Two Ventures is an early-stage venture capital firm founded by Katey Caldwell, investing in ambitious founders building SaaS, fintech, open source, marketplaces, and developer tools companies. The firm writes small, fast checks at the pre-seed and seed stages.
Deal activity increased 300% year-over-year (4 deals in the last 12 months). Their most common stage is seed (89% of deals). Average disclosed round size is $3.9M (across 26 rounds with reported amounts).
Portfolio
26
Fund Size
$20M
Top Stage
Seed
Last 12 Mo
4
Team
Portfolio Breakdown
Stage Distribution
Sector Distribution
Investment Activity
DealsAvg Round Size
Portfolio
28 investments
| Company | Round | Amount | Date |
|---|---|---|---|
 Crimson | Seed | $2.5M | May 2026 |
 Nexus Enterprise | Seed | $4.3M | Apr 2026 |
 Nexus | Seed | — | Jan 2026 |
| Crimson | Seed | $2.5M | Jan 2026 |
 NEXUS | Seed | $4.3M | Jan 2026 |
 Socratix AI | Seed | $4.1M | Oct 2025 |
| Socratix AI | Unknown | $4.1M | Oct 2025 |
 Magic Patterns | Series A | $6M | Jan 2025 |
 Socratix | Seed | $4.1M | Jan 2025 |
 Fondo | Seed | $7M | Nov 2024 |
 Greenboard | Seed | $4.5M | May 2024 |
 PointOne | Seed | $3.5M | Jan 2024 |
 PointOne | Seed | $3.5M | Jan 2024 |
 Mintlify | Seed | $2.8M | May 2022 |
 Slai | Seed | $3.5M | May 2022 |
 slapdash | Seed | $3.7M | Mar 2021 |
 Fondo | Seed | $7M | — |
 Ellipsis | Seed | $2M | — |
 Pirros | Seed | $2M | — |
 Trigger.dev | Seed | — | — |
 Voicepanel | Seed | $2.4M | — |
 Archil | Seed | $6.7M | — |
 TRIGGER | Seed | $3M | — |
 Resquared | Seed | $5M | — |
 Dropback | Pre-Seed | $1.6M | — |
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Top Co-Investors
Y Combinator26 shared
General Catalyst8 shared
Transpose Platform6 shared
Wayfinder Ventures4 shared
Liquid 2 Ventures4 shared
Soma Capital4 shared
Rebel Fund4 shared
Phosphor Capital3 shared
Pear VC3 shared
Pioneer Fund3 shared
Amino Capital3 shared
FundersClub3 shared
8VC3 shared
Script Capital3 shared
Ritual Capital3 shared
Bessemer Venture Partners3 shared
Gokul Rajaram2 shared
Motley Fool Ventures2 shared
Symphony Ventures2 shared
Together Fund2 shared
Last updated: 7 October 2026