First Round Capital
Seed-stage firm known for its founder community and operational support, with early bets on Uber and Square.
First Round is the gold standard of seed investing - they literally pioneered the category when Sand Hill Road dismissed them as a 'cute novelty' in 2005. What makes them special isn't just their legendary returns (that $510K Uber investment became $2.5B), it's their operator-first approach that treats founders like partners, not just portfolio companies. Founders say their First Round partner is 'the first person they text and call, their coach in the corner — and the kick in the ass when they need it most.' The firm built an entire platform team (GTM experts, recruiters, content strategists) to fill functional gaps in your early team - usually founders have to choose between early stage focus and functional expertise, but with First Round you can have your cake and eat it too. Their data-driven insights (like female-founded companies outperforming all-male teams by 63%) and content empire (First Round Review) show they're not just writing checks but building the playbook for early-stage success.
- —Best for: Seed-stage founders who want a true partner, not just capital - they'll fill functional gaps until you hire your own team
- —Known for: Legendary returns, operator-first approach, and creating the modern seed investing category
- —Sweet spot: Contrarian founders with compelling insights into markets others miss, especially in enterprise/AI/fintech
First Round's core thesis centers on finding compelling and contrarian insights into how the world works. They specifically look for founders who understand markets or needs in ways others miss, paired with the strongest possible founding teams. Rather than predicting the future themselves, they position founders as the discoverers of what's next, and First Round's role is to accelerate their path from idea to product-market fit.
First Round Capital invests exclusively at the Seed and Series A stages, with check sizes ranging from $750K to $4M on the lead side. Their investments tend to cluster around enterprise, AI, hardware, healthcare, fintech, and consumer, but they maintain curiosity beyond those areas. They're sector-agnostic primarily focusing on seed-stage technology startups, having invested in over 847 startups with a robust portfolio including high-profile companies.
Josh has been an active entrepreneur and investor since the Internet's commercialization. He's been a founder three times (four if you include founding First Round). In 1992, while in college, Josh co-founded Infonautics Corporation and took it public on NASDAQ in 1996. Josh co-founded Half.com in 1999 and led it to become one of the largest sellers of used books, movies and music in the world. Half.com was acquired by eBay in 2000. Since founding First Round in 2004, Josh has frequently made the Forbes 'Midas List' which ranks the top 100 tech investors.
Bill Trenchard is a founder-turned-VC who scaled LiveOps to $100M, sold Jump Networks to Microsoft, and teaches a process-driven fundraising playbook (Pitch Assist, 10/90 rule) to spot category-defining startups early. He's known as a fundraising savant who created First Round's hands-on Pitch Assist program and teaches founders his distinctive process-driven approach. Bill joined in 2012 and has made the Midas List five times after leading investments in Looker, Verkada, and Flexport.
Brett Berson started at First Round in 2008 as a college intern before being named a partner in 2016. He focuses on enterprise and go-to-market investments and has been instrumental in developing First Round's operational approach to supporting founders.
Todd Jackson spent his career in product management at some of the biggest companies in tech, including Google, Facebook, Twitter, and Dropbox. He brings deep product expertise to First Round's AI and product-focused investments.
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