When we first backed Sigil Wen, we knew we were backing an unusually resourceful builder. He seeks out exceptional people, finds ways to help them, earns their trust, and keeps choosing harder problems.
With Conway Research — and its first product, Underdog — Sigil is taking on the challenge of bringing personal intelligence onto the devices we own. He is motivated by a conviction we share: the AI that knows us best should work for us, with data we control.
Sigil came to San Francisco at 17 without much of a network. For a time, he slept at a WeWork. He skipped college to work on AI and spent nearly a year in a hacker house, building alongside researchers and engineers who helped create DALL·E, Whisper, GPT-3, and Stable Diffusion.
Andrej Karpathy lived there. Anthropic cofounder Ben Mann invited Sigil to become one of the earliest testers of what became Claude. David Holz showed him the first version of the model behind Midjourney.
We first met Sigil when Naval Ravikant brought him to an event Chris was hosting in 2021. Sigil went on to help Naval launch Airchat, bringing emerging AI models into a product people used every day and recruiting most of its engineering team. Naval also made him the youngest member of Spearhead. In 2025, Sigil received the Thiel Fellowship.
The common thread is how Sigil builds relationships. He helps first, whether he’s recruiting engineers or helping the founders he backs hire and raise money. He treats each relationship as if it would exist for decades, as he puts it. Those relationships have given him years of learning directly from people building at AI’s frontier.
Since then, we’ve watched him develop his own point of view on AI. The problem behind Underdog is personal. Years ago, while Sigil was living and hacking alongside Karpathy, a bug in a popular email app exposed his private, privileged emails to other users. The fallout helped motivate him to build products that empower people while keeping their data safe.
At the same time, he was exploring how much intelligence could fit on the devices we carry every day. He got GPT-2 running on his Apple Watch and later helped bring Whisper to the iPhone at Airchat. As smaller models became more capable and hardware improved, he saw a path to running useful personal AI locally.
As AI moves from answering questions to acting on our behalf, its usefulness increasingly depends on access to our conversations, commitments, documents, and preferences. The information that makes an assistant valuable is also the information we most need to protect.
Underdog is Sigil’s answer: personal intelligence that runs on your own devices, helping you make decisions and reclaim your time, even offline.
For us, the opportunity extends beyond any one task. As Underdog improves its models and brings them to more consumer devices, we believe it can put powerful AI in billions of people’s hands. AI should be a liberating equalizer: free, capable, reliable assistance that gives everyone with a phone or computer sovereignty over their time, information, and choices.
Sigil has spent years earning people’s trust and pushing the limits of what he could build. With Conway Research, he is bringing those strengths together around a problem that will matter to everyone using AI.
We’re thrilled to lead Conway Research’s first round of funding and partner with Sigil as he builds Underdog.
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