I recently read eBoys, a book by Randall Stross about the founding Benchmark Capital team’s investments in the run-up to the 2000 internet bubble. These investments include eBay and Webvan.
The book is the result of the Benchmark team giving access to Randall to sit in on their internal meetings and interact with their portfolio companies. This decision was likely taken to market the newly founded fund and while it worked out in some respects, it also backfired in others. There are several instances in the book that the Benchmark partners would have likely preferred to leave out.
But setting that aside, the book provides valuable insights into the chaotic world of startups, the uncertainty which governs venture investments, and lessons from the run-up to the 2000 internet bubble.
If you want to read the book, you can buy it here.
Also published on Medium.