Aileen Lee & Rachel Carlson: Venture Capital & Education

A Conversation with Aileen Lee and Rachel Carlson

This discussion was captured on September 7, 2021. It features insights from Aileen Lee, a highly regarded venture capitalist, and Rachel Carlson.

Aileen Lee’s Investment Philosophy

Aileen Lee, founder and General Partner at Cowboy Ventures, shared her key investment criteria during the conversation. Her standards are well-known within the venture capital community.

The discussion highlighted how Rachel Carlson, of Guild Education, successfully fulfilled – and surpassed – Lee’s rigorous requirements for investment.

Guild Education: A Case Study

The event provided a detailed look into the factors that made Guild Education an attractive investment opportunity. Lee and Carlson discussed the specific qualities that aligned with Cowboy Ventures’ portfolio strategy.

Live Startup Pitch Feedback

A unique element of the event was the opportunity for startups to receive direct feedback. Lee and Carlson offered their live assessments of pitches presented by members of the audience.

This interactive session provided valuable insights for aspiring entrepreneurs. The feedback focused on key areas such as market opportunity and execution strategy.

Cowboy Ventures’ approach to evaluating startups was clearly demonstrated through this live Q&A.