I’m often asked by friends or startups I advise for a practical reading list that provides context, expected skills, and common vocabulary for the new job. Below is the reading list I gave to my new hires at Square when I led the risk, data science, and Square Capital teams. For each section the list is deliberately short—because I’m picky about signal-to-noise when requiring others to read. Hope you find this helpful:

General Business

Making Good Investments


Product Management

Data Science

Successful Interactions With People

People Management

  • High Output Management: the definitive guide on effective people management techniques; comes across as a bit dry / unempathetic so make sure to balance with HTWFAIP
  • The Hard Thing About Hard Things: the best of Ben Horowitz; practical advise from a startup manager who learned on the job
  • The Checklist Manifesto: create, refine, and adhere to checklists to improve performance (link is to a free summary rather than the actual book)