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TwentyTwo VC

San Francisco, California · Invests in US; LATAM; Asia · Website

Pre-SeedSeedE-commerce & MarketplacesB2B SaaSAI & Machine LearningDeveloper ToolsFintechEnterprise SoftwareDeveloper Tools & InfrastructureFintech & Payments

Thesis

Invest earlier than most other investors and make decisions quickly. We focus on ambitious founders building unusually great companies in SaaS, developer tools, fintech, open source, and marketplaces. Our smaller check sizes allow founders to maintain control and enable us to deploy efficiently across 100+ companies.

Likely not a fit for

We avoid large, slow decision-making processes, mature companies, or founders who need extensive governance involvement.

How they invest

Lead or follow
Leads or follows
Typical decision
~1 week
Warm intro
Not required
Involvement
Advisor
Fund status
Actively deploying
Decision process
Partnership vote

Partners & team

2 contacts on file

KC

Katey Caldwell

General PartnerFounder and Managing Partner · Primary contact

+ Pitch

k•••@tw•••.vc

LinkedIn profile

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FB

Fred Benenson

General PartnerGeneral Partner

+ Pitch

f•••@tw•••.vc

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Portfolio

AirbyteDeveloper Tools Infra

Airbyte is the open-source standard for EL(T), enabling data teams to replicate data from applications, APIs, and databases to data warehouses, lakes, and other destinations. Founded in 2020, the company focuses on solving data integration challenges through an open-source approach, allowing teams to adapt pre-built connectors to their specific needs.

Build BuddyDeveloper Tools Infra

BuildBuddy is the developer productivity platform built for Bazel — the open source build system that allows you to build and test software 10x faster. It offers remote build execution, caching, and a user-friendly web UI for build logs.

CronEnterprise Software

Cron is the next-generation calendar for professionals and teams, now integrated with Notion to enhance time management and organization.

DotsGaming

Dots is a game design studio known for its engaging puzzle games like Two Dots and Garden Tails, which challenge players to connect dots and solve puzzles across various levels.

FinleyFintech Payments

Finley Technologies provides modern loan administration software and services for private credit and banks, focusing on automation, compliance, and portfolio monitoring.

FractionalProptech Real Estate

Fractional is a financial technology company that facilitates fractional ownership of investment properties through investment clubs, allowing individuals to pool resources and make collective investment decisions without the complexities of traditional syndications.

GlooEnterprise Software

Gloo Chat Inc. provides services that involve processing personal information for various purposes, including improving and administering their services, communicating with users, and ensuring security.

Great QuestionEnterprise Software

Great Question is an all-in-one UX research platform that empowers teams to conduct customer research efficiently, integrating recruitment, scheduling, interviews, analysis, and sharing into a single AI-powered solution.

InfisicalSecurity Cyber

Infisical is an all-in-one platform for securely managing application secrets, certificates, and access management across teams and infrastructure, automating key security processes to enhance security posture and operational efficiency.

Keeper
LoopsEnterprise Software

Loops is an email platform designed specifically for modern software companies, enabling them to manage product, marketing, and transactional emails through a single interface.

PoplarML

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Research briefRead more
TwentyTwo VC Research Document Investment Thesis TwentyTwo VC, founded by Katey Caldwell in 2018, is an early-stage seed fund with a singular conviction: invest earlier than most other investors and make decisions quickly. The fund focuses on ambitious founders building unusually great companies in sectors where small, fast checks can create outsized impact. Rather than following market consensus,

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