Crypto

Investing in Conway, the Creator of Underdog

Chris Dixon, Gabriel Vasquez, and Elizabeth Harkavy Posted October 2, 2026

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.

About the Contributors
Want More a16z Crypto?

Your go-to-guide to the next internet.

Learn More
Recommended For You
Infra

new Investing in doxxnet

Joel de la Garza and Martin Casado
Growth

new Investing in Armadin

David George and Stephenie Zhang
Consumer

Investing in Highstock

Olivia Moore and Justine Moore
Growth

Investing in Cognition

Marc Andreessen

Want More crypto?

Web3 Weekly, a newsletter from a16z crypto, is your go-to-guide to the next internet.

Sign Up On Substack

Views expressed in “posts” (including podcasts, videos, and social media) are those of the individual a16z personnel quoted therein and are not the views of a16z Capital Management, L.L.C. (“a16z”) or its respective affiliates. a16z Capital Management is an investment adviser registered with the Securities and Exchange Commission. Registration as an investment adviser does not imply any special skill or training. The posts are not directed to any investors or potential investors, and do not constitute an offer to sell — or a solicitation of an offer to buy — any securities, and may not be used or relied upon in evaluating the merits of any investment.

The contents in here — and available on any associated distribution platforms and any public a16z online social media accounts, platforms, and sites (collectively, “content distribution outlets”) — should not be construed as or relied upon in any manner as investment, legal, tax, or other advice. You should consult your own advisers as to legal, business, tax, and other related matters concerning any investment. Any projections, estimates, forecasts, targets, prospects and/or opinions expressed in these materials are subject to change without notice and may differ or be contrary to opinions expressed by others. Any charts provided here or on a16z content distribution outlets are for informational purposes only, and should not be relied upon when making any investment decision. Certain information contained in here has been obtained from third-party sources, including from portfolio companies of funds managed by a16z. While taken from sources believed to be reliable, a16z has not independently verified such information and makes no representations about the enduring accuracy of the information or its appropriateness for a given situation. In addition, posts may include third-party advertisements; a16z has not reviewed such advertisements and does not endorse any advertising content contained therein. All content speaks only as of the date indicated.

Under no circumstances should any posts or other information provided on this website — or on associated content distribution outlets — be construed as an offer soliciting the purchase or sale of any security or interest in any pooled investment vehicle sponsored, discussed, or mentioned by a16z personnel. Nor should it be construed as an offer to provide investment advisory services; an offer to invest in an a16z-managed pooled investment vehicle will be made separately and only by means of the confidential offering documents of the specific pooled investment vehicles — which should be read in their entirety, and only to those who, among other requirements, meet certain qualifications under federal securities laws. Such investors, defined as accredited investors and qualified purchasers, are generally deemed capable of evaluating the merits and risks of prospective investments and financial matters.

There can be no assurances that a16z’s investment objectives will be achieved or investment strategies will be successful. Any investment in a vehicle managed by a16z involves a high degree of risk including the risk that the entire amount invested is lost. Any investments or portfolio companies mentioned, referred to, or described are not representative of all investments in vehicles managed by a16z and there can be no assurance that the investments will be profitable or that other investments made in the future will have similar characteristics or results. A list of investments made by funds managed by a16z is available here: https://a16z.com/investments/. Past results of a16z’s investments, pooled investment vehicles, or investment strategies are not necessarily indicative of future results. Excluded from this list are investments (and certain publicly traded cryptocurrencies/ digital assets) for which the issuer has not provided permission for a16z to disclose publicly. As for its investments in any cryptocurrency or token project, a16z is acting in its own financial interest, not necessarily in the interests of other token holders. a16z has no special role in any of these projects or power over their management. a16z does not undertake to continue to have any involvement in these projects other than as an investor and token holder, and other token holders should not expect that it will or rely on it to have any particular involvement.

With respect to funds managed by a16z that are registered in Japan, a16z will provide to any member of the Japanese public a copy of such documents as are required to be made publicly available pursuant to Article 63 of the Financial Instruments and Exchange Act of Japan. Please contact compliance@a16z.com to request such documents.

For other site terms of use, please go here. Additional important information about a16z, including our Form ADV Part 2A Brochure, is available at the SEC’s website: http://www.adviserinfo.sec.gov.