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eBoys: The First Inside Account of Venture Capitalists at Work

3.92 of 5 stars 3.92  ·  rating details  ·  182 ratings  ·  11 reviews
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
Mark Casey
This was a fantastic listen. Randall Stross had great access to the Benchmark team, and told the story of their 1998-1999 investments extremely well.

It's too bad he published the book before the big crash of 2000, as it would have been fun and interesting to see what he and the partners thought on the way down.

As it is, we know what happened both on the good side of things (eBay, Red Hat, Juniper, Ariba to a degree) and on the bad (Webvan, TriStrata, and a few others).

I had forgotten all about
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.
Jerry Tian
Great book that peeks into a famous VC firm in the pre-bubble era.
Pretty interesting story following the guys from Benchmark through the dotcom boom. The jacket hypes them as the "guys who backed Ebay, Webvan..."

Webvan. Interesting.
At the time I found this an entertaining read. It was a good introduction to the world of venture capital, and the valley during the first internet boom.
Sean Flynn
Interesting read for anyone that ever wants to learn about the venture capital industry.
Jim Kelly
A great book on the bubble before it burst! So exciting.
Josh Steimle
A great snippet of dot com history.
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“On a daily basis the venture capitalist was not concerned with historical impact; he worked to create wealth for himself and his limited partners. However, among the Benchmark partners there was awareness that framing one’s professional raison d’être in the language of financial return meant that one was hostage to the vagaries of the market—and even when the market is buoyant, there is little that is soul-quenching about mere numbers. “The really big wins are where all the rewards come from,” Bob Kagle once pointed out, before eBay had gone public. The rewards he was referring to were the emotional ones, not the financial ones, and they were rewards derived not from a game of assuming personal risk—the venture guys had a portfolio across which risk could be spread—but from being backers of entrepreneurs, the ones who commercialized new technology and introduced new products and services—and were the ones who really took on risk. “Nine times out of ten they’re taking on some big, established system of some sort.” He dropped his voice for emphasis: If the individual entrepreneur won, even for the venture guys it produced an “exhilarating feeling”—he groped for the right words—“it’s confirmation that one person with courage can make a difference.” This was the minidrama Kagle and his colleagues had seen play out triumphantly again and again. The work itself did not have any neat demarcations of beginning, middle, and end. The funds seemed to be evergreen, fresh capital materializing as soon as the till was exhausted. The calendars of the partners, revolving as they did around looking at new business plans, meeting new entrepreneurs, considering new deals, gave a feeling of perennially beginning afresh. For them, it was the best place in the cosmos to get the first peek at the future.” 0 likes
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