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Publisher's Summary

The first inside account of life within a Silicon Valley venture capital firm, eBoys is the fascinating true story of the six tall men who backed eBay, Webvan, and other billion-dollar start-ups that are transforming the Internet and setting a new pace for the economy.

Randall Stross, author of acclaimed books on Microsoft and Steve Jobs, blends a business historian's perspective with a journalist's flair for suspenseful storytelling to look at wealth creation up close. For two years, Stross gained unprecedented access to the venture capitalists at Benchmark, an upstart firm founded by thirtysomething renegades whose average height happens to be 6'5. Since Benchmark's founding in 1995, each partner's net worth has increased, on average, $100 million annually.

Stross was present as the Benchmark boys debated which businesses to support, and by recounting their conversations in testosterone-rich detail, he offers listeners the most precise and enlightening account of the ways in which venture capitalists think, evaluate prospects, and wield influence.

The author also gained access to a number of the Benchmark-backed start-ups, including a small, privately held San Jose company called eBay. The value of the company grew from $20 million to more than $21 billion within two years of Benchmark's investment, an increase of 100,000 percent. Business Week called it "probably the best venture capital investment of all time."

Executive Producer: Dan Zitt
Original Jacket Photo: (front) Kevin Harvey, Andy Rachleff, Bruce Dunlevie; (back) Dave Beirne, Bill Gurley, Bob Kagle/Margot Hartford
Original Jacket Design: Whitney Cookman
©2000 by Randall E. Stross
(P)2000 Random House, Inc.

Critic Reviews

"This eye-opening first-hand account of the young, gutsy, and mega-rich entrepreneurs who are financing today's hottest Web-based businesses will leave you gasping." (Glenn Brenner, author of The Emperors of Chocolate)

What members say

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  • Overall
  • Sean
  • Newport Beach, CA, USA
  • 12-01-03

Entertaining but misinformed

I found the book to be totally engrossing and entertaining, but also amusing (not always in a good way), a little inaccurate, and probably more than a little embarrassing to the participants in hindsight. If you are looking for an entertaining read about the highest fliers in the internet bubble, this is a great choice. But if you are hoping to learn more about venture capital from an insiders point of view, this book will lead you astray.

The description of the attitudes and lingo at Benchmark and other venture firms in the book seem out of place. The author seems to be describing the macho environment of an investment bank rather than the more subdued approach of venture capitalists. But maybe that's the way things actually were at Benchmark in the late 1990s.

As a venture capitalist myself, I was surprised by the apparent lack of due diligence and the thin premises upon which the partners seemed to make their investment decisions. I'm sure that my perception of this is in part a consequence of the author's choice to gloss over the nitty gritty details. But explicit dialogue between the partners shows that the partners did in fact have a shoot-from-the-hip style. I am hardly qualified to question the partners' instincts when they were so successful. But I do think it is a wildly inaccurate portrayal of the industry as a whole.

16 of 17 people found this review helpful

  • Overall

Entertaining look at one VC firm

I thoroughly enjoyed listening to eBoys. The audiobook doesn't attempt to be a treatise on Venture Capital. Instead, it gives you a glimpse at a new "democratic" VC firm, Benchmark, and describes some of the more interesting ventures like Ebay and Webvan. It gives you the venture capitalist perspective on those ventures, and how the standards of investing changed during the dot-com mania. This is not a textbook on venture capital, but it is an entertaining peek at how some of the big internet deals went down.

6 of 6 people found this review helpful

  • Overall
  • Wayzon
  • Holly Springs, GA, USA
  • 01-23-08

Could have been a lot better

I aspired to be a venture capitalist before I heard this book. It is interesting to get a fly-on-the-wall perspective of how VC's make multimillion dollar decisions like most people debate what to get on their pizza. It's filled with tons of profanity quoting Dave Burns which I find unnecessary. I wasn't impressed with any of the characters and as an entrepreneur, it makes me want to avoid VC funding at all costs.

3 of 3 people found this review helpful

  • Overall

Intriguing look into venture capital

Although a bit dated (from the pre-tech crash era), a thoroughly engrossing view of how venture capital works. Lots about the development of EBay.

1 of 1 people found this review helpful

  • Overall
  • Andrew
  • Shreveport, LA, United States
  • 01-25-05

THE book on inside venture capital investing

I tend to only review books that I either absolutely love or absolutely hate... this book falls into the former category. I read the actual book a couple months ago and found that it was so good I didn't want to put it down -- I as actually sad when I finished. I was ecstatic to see that Audible added it as an audiobook... I just finished listening to it and again find myself awestruck by this book.

Eboys is about Benchmark Capital of Menlo Park, California -- arguably the #1 venture capital firm in the world. It chronicles the day to day dealings of the partners, their interactions with entrepreneurs from all walks of life, and the multi-billion dollar companies they've funded... the most prominent of which is eBay, a company that made all of the founding partners 300 million dollars each.

This is an awesome book for a budding entrepreneur -- it really gives you an inside fly-on-the-wall look at how the mysterious and sometimes daunting world of high stakes venture capital works. But it's not just a how-to guide in obtaining venture capital, as the real life stories of the Eboys are fascinating, entertaining, and incredibly inspiring.

Don't think about it -- GET THIS BOOK!

3 of 4 people found this review helpful

  • Overall
  • Bob
  • Valrico, FL, USA
  • 01-08-04

Good entertaining read

Great entertaining read on the efforts made by several of the popular internet startups to get funding and start in the internet boom years.

Only two quirks, seems to jump around date wise as the different projects (ebay, webvan,, etc) are followed. And the book took place in 2000 so the stories are a bit dated.

1 of 1 people found this review helpful

  • Overall

Strong Language Alert

This is a fascinating book but it contains numerous sections of densely packed profanity. I know there are two schools of thought on this, to include crude profanity or not to. However, I found the straightforward reporting (sans the macho quotes from overamped venture capitalists) to be engrossing. But hearing an F-bomb every few minutes was too jarring and I reluctantly had to abandon ship.

This book is not safe to listen to with kids in the car with you...

2 of 3 people found this review helpful

  • Overall
  • Eric
  • Lawrence, KS, USA
  • 08-18-04


I found this one hard to get through. The writer did a horrible job of keeping focus and the story was all over the place. I would recommend Dot.bomb before this one. The only exciting part of the book was eBay's IPO and "the outage." Other than that, a totally snoozer. I couldn't wait for it to be done and I'm glad it's finally finished.

3 of 5 people found this review helpful

  • Overall


Great content and a great story.

  • Overall
  • Tej
  • Cupertino, CA, USA
  • 09-05-07

A little pompous

.. at times.. a little light on what it takes to run a start-up.. but it makes a good short listen about the go-go days of the internet.