James Reinhart is the co-founder and CEO of thredUP, one of the world’s largest online resale platforms. thredUP designed a digital resale experience that aims to take the work and risk out of thrift in an effort to make used clothes the new normal and create a more sustainable future for fashion. Prior to thredUP, he helped develop one of the nation’s premier public schools, Pacific Collegiate School. In this conversation with Stanford adjunct lecturer Ravi Belani, Reinhart discusses how thredUp arrived at its business model, and explores the challenges, pivots, and insights that emerged during thredUP’s decade-long journey to becoming a publicly traded company.