a16z announces leading investment in Conway Research's Series A, backing founder Sigil Wen and his first product Underdog
a16z partners Chris Dixon, Gabriel Vasquez, and Liz Harkavy jointly announced the leading investment in Conway Research's Series A, backing founder Sigil Wen and his first product Underdog. The amount has not been disclosed.
The article states that Sigil was introduced to Dixon at an event hosted by Naval Ravikant in 2021. He later assisted Naval with Airchat, integrating new models into everyday products and recruiting most of the engineering team; Naval also made him the youngest member of Spearhead. He received the Thiel Fellowship in 2025.
When he arrived in San Francisco at 17, he had almost no connections and once slept in WeWork, dropping out of college and living in a hacker house for nearly a year. Andrej Karpathy lived there. Anthropic co-founder Ben Mann invited him to be one of the earliest testers of Claude. David Holz showed him the first version of the model behind Midjourney. Others in the house included people involved with DALL·E, Whisper, GPT-3, and Stable Diffusion.
Underdog is defined as personal intelligence running on users' own devices, capable of assisting decision-making offline. The motivation is linked to two past incidents: while living with Karpathy, a vulnerability in an email application exposed his private emails to other users; he had previously run GPT-2 on an Apple Watch and integrated Whisper into the iPhone via Airchat.
The shared judgment of the three is that the AI that knows you best should work for you, with data under your control. Once an assistant transitions from answering questions to managing tasks, it must handle conversations, commitments, documents, and preferences, which are also the most sensitive information. They envision a future covering billions of phones and computers, giving users sovereignty over time, information, and choices.
The buyer is a16z partners who have previously invested in him, along with Naval's network that introduced him; the seller is a cloud assistant that must upload context to become smarter. The event was driven by the leading investment document. Funding is shifting from pay-per-call personal data to local models, benefiting teams that can deliver offline assistants on old devices, while putting pressure on assistant companies that keep emails and calendars on their own servers.
Source: Public information
ABAB AI Insight
Chris Dixon at a16z focuses on crypto and web investments, first establishing a relationship node before writing a long piece in the next round. The 2021 event was not a roadshow; it was Naval bringing people in. Sigil subsequently used engineering recruitment from Airchat and his young member status in Spearhead to turn that introduction into a verifiable work record. Ben Mann provided early testing for Claude, David Holz for the first version of Midjourney, and Karpathy for cohabitation; none of these are in the company registration documents but are included in the leading investment document.
The capital path is a trust discount. The article does not mention valuation but states that he first helps out and then maintains relationships over decades, recruiting and financing for the founders he invests in. Underdog's data claim is directly linked to the email leak incident, with the product designed to create an assistant that does not upload data. a16z is not looking for a one-time email feature but a local intelligent entry point on billions of devices.
A comparable case is Dixon's early positioning of Coinbase as the default entry for Bitcoin, repeating the phrase "users should control their own data" in subsequent projects. The current position is a control period. Claude, Midjourney, and Whisper are already other people's products, and Sigil is transitioning from tester and housemate to someone who needs to rebuild personal layers on devices. The Thiel Fellowship will only be obtained in 2025, later than these relationships.
Structurally, this represents a transfer of pricing power. The pricing power of cloud assistants comes from holding conversations and documents, while the leading investment document shifts that ownership back to devices. Early testing qualifications are used to prove he has seen the cutting edge, not to prove he owns these models. If local models can complete tasks offline, calling fees will decrease; if cutting-edge models are still needed to handle difficult problems, sovereignty will only cover the everyday, not the most challenging layer.
ABAB News · Cognitive Laws
The leading investment document is pricing relationships, not valuations.
Being an early tester does not equate to owning the model.
The system that knows you best should not first store your existence with others.