Austin McChord built Datto from a dorm room into a billion-dollar company without an elite education background, then became a venture investor at Outsiders Fund where he backs founders outside traditional tech hubs and typical investor archetypes. Unlike most VCs who are former operators, he actively runs companies while investing—currently serving as CEO of health-tech company Casana alongside his Managing Director role—giving him real-time experience with the challenges founders face.

• Deep focus on the Managed Service Provider (MSP) industry and cybersecurity standards. He frequently discusses the critical role MSPs play in protecting small businesses and analyzes major security breaches, such as the Kaseya attack where he criticized poor security practices like storing passwords in plain text.
• Enthusiasm for hardware engineering and mechanical complexity. Beyond software, he is heavily involved in combat robotics through the league he founded and often tweets about physical tech, such as questioning how ethernet is routed through magnetic connectors on new computers or marveling at the density of equipment in an Airbus A350 avionics bay.
• Critical eye for user experience and digital privacy. He often calls out consumer applications for using dark patterns or intrusive data practices, such as UberEats making it difficult to disable ads without losing order tracking or Airbnb hosts using third-party algorithms to screen guests based on social media profiles.
• Active support for hardware-enabled health technology. He frequently highlights progress in remote patient monitoring, specifically mentioning his work with Casana, a company developing smart toilet seats to track health metrics, suggesting an interest in startups that bridge physical devices with healthcare data.