Thoughts that inform my investment decision making these days…

  1. The two things that matter most in the best-of-the-best companies post product-market fit are: (a) Cost efficient growth mechanisms (eg: virality, customer success driven growth) (b) Product-driven structural defensibility (eg: network effects).
  2. The common thread across the greatest of investors has been their focus on moat/defensibility. Warren Buffett used to make the analog of the ‘unregulated toll bridge’; Peter Thiel talks about monopolies; Fred Wilson/USV talks about ‘Large networks of engaged users, differentiated through user experience, and defensible through network effects’.
  3. The desire to be great vs. good is very important.
  4. As an investor, it’s easy to fall into the trap of pattern matching. Yes, pattern matching matters. But more important to retain the open mindedness to be able to identify a founder who’s going to rewrite the rules in an industry. That’s where alpha gets created.
  5. Founder’s domain expertise/experience can provide a first-mover advantage that dates prior to the founding of the startup.
GovTech CEO Interview Series: Zachary Bookman, OpenGov

GovTech CEO Interview Series: Zachary Bookman, OpenGov