TwentyTwo VC
VC Fund
San Francisco, United States
TwentyTwo VC is an early-stage venture capital firm dedicated to investing in a new generation of companies tackling our present and future quality of life.TwentyTwo VC are composed of active investors, investing in people and companies doing great things. We make early-stage investments in companies typically post-launch, pre-seed, seed. We arelooking for companies that are solving for quality of life, bringing something new to the table, and executing scalable business models. Beyond that, we seek magnetic, tenacious, adaptable founders who aren’t afraid of the big ideas and ultimately ship great things.
- Total investments:
- 69
- Last investment:
- Lead investor:
- 1%
- Fund size:
- $9.2M
- Last fund:
Last updated:
For AI agents: llms.txt
Industries TwentyTwo VC invests in
Stages TwentyTwo VC invests in
Countries TwentyTwo VC invests in
Round sizes
Contacts
| Name | Phone | Socials | |
|---|---|---|---|
Round size
- Seed
- $1.5M–$6M
- Pre-Seed
- $835k–$1.3M
- Series A
- $7M–$14M
Investment Focus
Industry
- Software 30 (43%)
- Artificial Intelligence 19 (28%)
- FinTech 18 (26%)
- Information Technology 17 (25%)
- SaaS 9 (13%)
Stage
- Seed 58 (84%)
- Pre-Seed 5 (7%)
- Series A 2 (3%)
- Series B 1 (1%)
- Funding Round 1 (1%)
Country
- United States 54 (78%)
- United Kingdom 2 (3%)
- Brazil 1 (1%)
- France 1 (1%)
- Mexico 1 (1%)
Team
| Name | Title | Investments | Links | |
|---|---|---|---|---|
Katherine Caldwell
Managing Partner
|
Managing Partner | Total investments: 13 | Find email |
Investments
| Company | Description | Round | Links |
|---|---|---|---|
| HUD is a platform that evaluates and enhances computer use agents across diverse environments and tasks. | $14M / Series A / Jun 18, 2026 | ||
| Crimson is a AI productivity platform that allows litigation lawyers to answer case specific questions. | $2.5M / Seed / May 28, 2026 | ||
| Agentic compliance software that makes GRC teams 10x more efficient. Already trusted by global leaders and the largest EU enterprises. What it does: - Extracts requirements from any file - Maps them to controls and policies - Shows gaps and monitors changes - Advises on maturity and next steps | $1.3M / Pre-Seed / May 21, 2026 | ||
| Mintlify is a software company that develops tools for creating, managing, and publishing developer documentation and API references. Its platform helps organizations build documentation websites, organize technical content, and provide searchable resources for developers. | $45M / Series B / Apr 14, 2026 | ||
| Nexus build production-ready AI agents without code for non-technical teams in large organizations. | $4.3M / Seed / Mar 31, 2026 | ||
| Sim is a software development company that provides an artificial intelligence platform to automate workflow and sync data. It is an open-source platform for designing, testing, and deploying AI agent workflows. It offers a visual, drag-and-drop canvas—similar to design tools—which lets developers connect large language models with various apps andlogic blocks. Users can integrate Sim with over 500 tools, such as Slack, Gmail, Supabase, and Pinecone, enabling autonomous agents that interact with real-world data and systems. The platform supports both hosted and self-hosted models, giving teams flexibility in choosing how and where their AI runs. Workflows built in Sim can be triggered manually, via scheduled events, or by webhooks, and they can be exposed as APIs or chat interfaces. Sim combines a no-code visual interface with production-grade capabilities like structured output, logging, and debugging, allowing teams to iterate quickly and scale their AI systems. | $7M / Series A / Nov 14, 2025 | ||
| Newton is an AI-powered dental workflow platform based in San Francisco that helps practices modernize patient engagement, reduce front desk burden, and drive revenue. Newton combines inbound and outbound voice AI for scheduling, AI-powered analytics for executive reporting, revenue cycle tools, and patient communication into one seamless platform.Newton drives revenue, streamlines operations, and delivers a patient-first experience.Newton was founded by Rohit Chaparala, CEO, and Sam Detjen, CTO. They are joined by Amsal Naseem, Founding Engineer; Cole Shaffer, Founding Operations Lead; Joe Olive, Founding Account Executive; and Rhea Phatak Nawaz, Product Designer. | $3.8M / Seed / Oct 22, 2025 | ||
| Dedalus Labs is building the MCP gateway for the next generation of AI applications by unifying the fragmented AI agents ecosystem with a single drop-in API endpoint. We host and manage your MCP servers, allowing users to go from idea to production in a single click. Users can pick any model from any vendor, mix-and-match whatever tools they wantfrom our MCP marketplace, and ship within minutes. YC S25. | $11M / Seed / Oct 15, 2025 | ||
| Vulcan builds AI tools that map U.S. laws and regulations, helping users draft, review, and stay compliant with legal documents. | $10.9M / Seed / Oct 09, 2025 | ||
| Lil Luv Dog is a premium pet care brand. | $1M / Pre-Seed / Sep 09, 2025 | ||
| See all 69 investments → | |||
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FAQ
What does TwentyTwo VC invest in?
TwentyTwo VC invests primarily in Software, Artificial Intelligence and FinTech startups, most often at Seed and Pre-Seed stage. Most of the 69 investments tracked by Shizune back companies in United States. The Investment Focus section breaks down every industry, stage and country in the portfolio.
What is TwentyTwo VC's check size?
TwentyTwo VC typically joins rounds of $1.5M–$6M at Seed, $835k–$1.3M at Pre-Seed and $7M–$14M at Series A. These ranges are 10th–90th percentile round sizes calculated from confirmed public funding rounds, so they are a realistic guide to the rounds TwentyTwo VC participates in.
How do I contact TwentyTwo VC?
Public channels for TwentyTwo VC include X (Twitter) and the website linked on this profile. For a verified work email and phone number, create a free Shizune account — contact data is searched across 20+ sources and validated before delivery, so your outreach lands in the right inbox.
Who are the partners at TwentyTwo VC?
The team at TwentyTwo VC includes Katherine Caldwell (Managing Partner). The Team section lists each member with their title, investment count and links.
Is Shizune's investor data accurate?
Yes — every stat on this profile is calculated from confirmed public funding rounds monitored across hundreds of sources since 2020. This profile was last refreshed in Sep 2026 and is updated monthly. Spotted something off? Use the “Suggest an edit” link near the top of the page.
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