Charlie Cheever

Charlie Cheever is a highly influential angel investor, primarily known for his co-founding roles at Quora and Expo. His transition into angel investing has seen him back some of the most successful technology companies of the past decade, establishing him as a prominent figure in the early-stage venture ecosystem. Cheever's investment philosophy appears to favor disruptive software and fintech solutions, often identifying companies with strong product-market fit and significant growth potential early on.

With a portfolio boasting over 25 investments, Cheever has demonstrated a keen eye for identifying future industry leaders. His notable early-stage bets include companies like Figma, which was acquired by Adobe for approximately $20 billion, and Plaid, acquired by Visa for $5.3 billion. Other significant investments include productivity giant Notion, valued at over $10 billion, and HR/payroll platform Rippling, which reached an $11.25 billion valuation. These successful exits and high valuations underscore his ability to pick winners and provide strategic value to nascent startups.

Cheever typically participates in Seed and Series A rounds, leveraging his deep operational experience from building and scaling Quora and Expo. While specific check sizes are not publicly disclosed for all his deals, given the competitive nature of the rounds he participates in and the caliber of the founders he backs, his initial investments likely range from $50,000 to $500,000. He is known for being a founder-friendly investor, offering not just capital but also valuable insights and network access to help early-stage companies navigate their growth trajectories. His track record solidifies his reputation as a sought-after angel investor in the Silicon Valley ecosystem.