Sergei Chestakov, Angel Investor

Sergei Chestakov is an angel investor whose portfolio includes 222, a Los Angeles–based social platform that uses AI to arrange curated in-person experiences, helping Gen Z users build authentic connections outside of traditional dating apps. He invests at the Series A stage, supporting startups focused on social networking and consumer technology. Sergei is the founder of Sergei Dot Com, LLC, providing software services for high-growth startups in New York, and previously worked as a software engineer at Replit, where he contributed to developer tools and collaborative coding platforms.