Brian Nichols is the co-founder of Angel Squad, a community where you’ll learn how to angel invest and get a chance to invest as little as $1k into Hustle Fund's top performing early-stage startups

Ev Williams grew up on a farm in Clarks, Nebraska. He dropped out of the University of Nebraska after a year and a half and moved around for several years doing technical work before landing in Silicon Valley in the late 1990s. In 1999 he co-founded Pyra Labs and built Blogger, one of the first widely accessible blogging tools. The word "blogger" comes directly from the product name. Google acquired Pyra Labs in early 2003.

He then co-founded Odeo, a podcasting platform, and Obvious Corp, an incubator. From Obvious Corp in 2006 emerged Twitter, the microblogging service that became one of the defining internet platforms of the next decade and a half. Williams became CEO of Twitter in 2008 and stepped down in 2010. He remained a significant shareholder.

The Twitter Wealth and Obvious Ventures

Ev Williams investments accelerated significantly when Twitter went public in 2013. In 2017 he sold approximately 30% of his Twitter holdings to finance new projects, including Obvious Ventures, the firm he had co-founded in 2014 with James Joaquin and Vishal Vasishth.

Obvious Ventures operates from a specific thesis: invest in companies that can make a positive change in the world. The firm has raised approximately $585 million across multiple funds, including a $123 million first fund, $191 million second fund, and $271 million third fund. In February 2025, Obvious filed to raise a $400 million fourth fund.

The portfolio reflects the world-positive thesis directly. Beyond Meat, the plant-based protein company, was an early Obvious investment and Williams had personal conviction about the category as a vegetarian himself. Beyond Meat IPO'd in May 2019 at a $1.5 billion valuation, though the stock has since fallen significantly from its peak. Blue Bottle Coffee, another Obvious investment, was acquired by Nestlé for $500 million in 2017. Nest, the smart home device company, was acquired by Google for $3.2 billion in 2014. Branch, the deeplinks infrastructure company, was acquired by Facebook.

Eric Bahn of Hustle Fund has observed that the most interesting investment funds are the ones built around a genuine thesis about what makes a category worth backing, rather than opportunistic deal flow. Obvious Ventures is an example: every deal runs through the same filter of world-positive impact plus viable business model. Angel Squad members developing their own investment theses can explore similar frameworks within the community at hustlefund.vc/squad.

Medium and the Long Bet

In 2012 Williams launched Medium, a publishing platform designed to give long-form writing the same accessibility that Blogger had given blogging. He has served as CEO and then Chairman. Medium has struggled to find a sustainable business model over its 12-year existence, cycling through multiple monetization strategies including advertising, subscription, and creator partnerships.

Williams has described Medium as a long-term bet on the idea that there is genuine appetite for thoughtful long-form content, and that the platform economics will eventually work in favor of the writers who produce it. That bet is still unresolved.

Medium and the Publishing Bet

Williams has described Medium as his most complex and unresolved business challenge. The platform has strong brand recognition among writers and readers who value long-form content. It has struggled to monetize in a way that adequately compensates the writers who produce that content, which creates a supply-side churn problem that eventually undermines the reader experience.

The platform has tried advertising, sponsorships, partner program revenue sharing, and subscription access. As of 2025, it runs primarily on a subscription model where paid members access all partner-program content and writers earn based on reading time. The model has critics who argue it underpays writers relative to the value they generate. Williams has been public about his belief that the right economic structure for quality writing platforms has not yet been found, and that Medium is still the experiment to find it.

That persistence is itself a signal. Williams has made $2 billion and could do anything. He keeps working on Medium.

Mozi and the Anti-Scroll Thesis

In 2024 Williams co-founded Mozi with entrepreneur Molly DeWolf Swenson. Mozi is a private social network that notifies users when friends or contacts are in the same city and shows them what local events their network is attending. There are no likes, no comments, and no algorithmic feed. The app is explicitly anti-engagement-metric, designed to get people off their screens and into the same room.

Mozi raised $6 million in a seed round from investors including Obvious Ventures, WndrCo, and BBG Ventures. It launched publicly at SXSW in March 2025.

Williams has explained the origin in personal terms: preparing his 50th birthday guest list, he realized he had fewer close friendships than he wanted. That personal recognition became the product insight.

Shiyan Koh of Hustle Fund has noted that the most durable founder stories are the ones where the problem is deeply personal to the founder. Williams built Blogger because he wanted an easier way to publish. He built Twitter because long-distance communication was too expensive. He built Mozi because he felt under-invested in real relationships. Each company starts from the same place. Angel Squad members learn to identify that personal-problem-to-company arc as one of the most reliable signals in early-stage evaluation. See the community at hustlefund.vc/squad.