32nd out of 38 books — 24 voters
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eBoys: The First Inside Account of Venture Capitalists at Work
Stross takes readers behind the scenes and inside the heads of the gutsy entrepreneurs who are financing the hottest businesses on the Web. The six tall men who started Benchmark, Silicon Valley's most exciting venture capital firm, put themselves at the cutting edge of the new economy by backing billion dollar start-ups like eBay and Webvan.
Paperback, 352 pages
Published May 29th 2001 by Ballantine Books
(first published May 23rd 2000)
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Interesting story of Benchmark Capital, a Silicon Valley VC firm and their investments during the dotcom boom in the late 90s and early 00s, pre- bursting of the bubble. Conveys the atmosphere of the industry and the personalities - all very gung-ho and "American", which makes for entertaining reading. The stories and mini-case studies of individual investments are quite insightful - there are a lot of pages devoted to Ebay's development and other less successful investments (e.g. ToysRUs websit...more
The world of venture capital is pretty opaque to me. This book is the best thing I've found so far about the courtship dance of the deal and the role VCs play in their portfolio companies. But, reading the book 10 years later, there's a lot of bubble-era absurdity too: the parade of vague ideas and barely-formed companies drawing bidding wars and hundred million dollar valuations is pretty unintentionally humorous in hindsight.
If you're interested in the subject of venture capital (or you're curious to hear how eBay got started) this is a GREAT read. The author also does a great job educating the reader on how VC works and what the jargon means. Probably a little dense for anyone who doesn't already have an interest in the topic. Only complaint was the foul language--too many F-words for a Mormon boy like me.