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Once You're Lucky, Twice You're Good: The Rebirth of Silicon Valley and the Rise of Web 2.0

3.68  ·  Rating Details ·  356 Ratings  ·  56 Reviews
The captivating story of the mavericks who emerged from the dot-com rubble to found the multibillion-dollar companies taking the Web into the twenty-first century

Once You?re Lucky, Twice You?re Good is the story of the entrepreneurs who learned their lesson from the Internet bust of 2000 and in recent years have created groundbreaking new Web companies. The second iteratio
Paperback, 336 pages
Published June 2nd 2009 by Avery (first published May 15th 2008)
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Community Reviews

(showing 1-30)
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Michael Gerald
I was a late-comer in the Internet social media. I joined Facebook only in 2009, Twitter in 2012, LinkedIn in 2012, and Goodreads also in 2012. It was the initial suspicion of these sites that was the reason. I was wary of privacy issues (I still am.) But I admit, these media have been helpful and fun.

"Once You're Lucky, Twice You're Good" attempts to tell the story of how the advent of social media in the 2000s rejuvenated the Web and brought it more sophistication and maturity than the initial
Hayashi Sakawa
Jun 28, 2008 Hayashi Sakawa rated it it was amazing  ·  review of another edition
Recommends it for: yound people
Recommended to Hayashi by: book review on Wired magazine
I really enjoyed reading it. This is the compelling narrative of the history-in-the-making told from an insider's point of view.
Kinman Li
May 30, 2008 Kinman Li rated it really liked it  ·  review of another edition
Great stories about the main players in Silicon Valley. What they went through and how they got through it
Angad Singh
Nov 22, 2016 Angad Singh rated it really liked it  ·  review of another edition
One of the best books for the Silicon Valley history enthusiast.
Sep 21, 2011 Herve rated it really liked it  ·  review of another edition
This is the third book I report on this blog about entrepreneurs. In fact it is the fourth if I include Inside Steve’s Brain (but this one is about a single entrepreneur). The two previous ones were interviews of many, i.e. Betting it all and Founders at Work. The beauty (and at same time weakness) of Once you’re lucky, Twice you’re good is that is is about web2.0. Is this new step in the Internet development a speculative bubble or a speculative revolution. It is probably too early to say even ...more
Oct 24, 2010 Bob rated it liked it  ·  review of another edition
Sarah's book was heavy on recent stories, but light on details both past and present. For example, her portrait of Max Levchin includes a few rise to to meet the challenge childhood stories along with PayPal and Slide, but neglects to mention the fact that he had four startups prior to these. If you only took this book as the source you would think that Max really did just get lucky by running into Peter Thiel in Palo Alto and that he is really tenacious and hard working. There was some trial an ...more
Rodrigo Rivera
Wenn man sich für Unternehmertum im Internet interessiert, ist es immer gut die Erfolgsgeschichten von anderen lesen zu können und sich dadurch inspirieren lassen.
Das Buch erfüllt genau diese Aufgabe und erzählt auf einer einfachen Weise, was bekannten Internet-Unternehmer wie Max Levchin, Gründer von Paypal und Slide, nach der Dotcom-Blase gemacht haben und wie es geschafft haben, obwohl die Allgemeinheit gemeint hat, Internet wäre nach der Dotcom-Boom tot.

Allerdings finde ich, dass Founders at
Feb 04, 2009 Rachel rated it liked it  ·  review of another edition
Recommends it for: Valleywag devotees
The book is a series of short biographical sketches of a dozen people who each started a successful website. Full of touching anecdotes or revealingly personal details, such as Jay Adelson being edged out of his own company by his VC investors, the book is as readable as a magazine of celebrity gossip.

Unfortunately, as a gossip magazine might, it delights in details about whether Marc Andreessen uses "LOL" when he chats or that a YouTube video is posted by Mark Zuckerburg's sister. So what?

A se
May 21, 2008 Rex rated it liked it  ·  review of another edition
The first book I've read (in full) since moving to NYC is a tale of internet companies in Silicon Valley.

So be it.

For those in the industry, this book will reveal some small stories you've yet to hear. With its tales of heroes and anti-heroes, entrepreneurs and venture capitalists, it's a modest success as a well-told genre piece.

For those outside this world, god bless your souls, this will feel boring, turgid, life-less. The language is journalistic; the ideas, too. You'll wish for something m
Nov 03, 2011 trav rated it really liked it  ·  review of another edition
Shelves: business, technology
If you follow tech companies and start-ups, you will enjoy this book. Basically the book is a collection of profiles of both businesses and the people behind them. Lacy does a great job of laying out a clear map of how the internet has spawned some of the coolest online apps and services.

She also does a good job of introducing us to the brains behind such places as Facebook, Digg, PayPal, Six Apart, etc. I really enjoyed getting to know some of the history and connections behind all the names th
Mark Cheverton
I have a soft spot for this kind of book, I guess it's my alternative to soap - high tech gossip. I'm always fascinated by the lives behind successful entrepreneurs.

However, entertaining as this was, it did leave me feeling a little disappointed. The detail behind the main characters are thin, and mostly deal with successes, when they were successful. It also gives the impression of Silicon Valley being just a small group of incestuous friends (which it may be!). I guess I would have just liked
Jan 21, 2011 Liam rated it really liked it  ·  review of another edition
"Digitization of media was inevitable; Napster was just the one who happened to spark much of it. The power of the web would come from the digitization of identity. What does that mean? Basically getting a true picture of who you are as a person represented online. It includes tangibles like your favorite movies and music and who your friends are, but also all the fuzzy gray area between that's harder to define. Your essence. If the Web could capture that, it could unlock all kinds of new, power ...more
Dec 19, 2008 Chad rated it it was ok  ·  review of another edition
This is a quick and informative read for anyone interested in the new Valley/tech boom. Unfortunately, Sarah comes off as having drunk too much Web 2.0 kool-aid and spends a little too much time gushing about Facebook, which, if she and Zuckerberg are right, will become for the Web what AOL was ten years ago: a walled garden. Also, in the current economic climate, it might sound a little bullish, especially on companies like Slide who seem to have no future. Finally, for a book that only the dig ...more
Jul 17, 2009 Joseph rated it liked it
It's always tough to write about how Silicon Valley really works, but Lacy basically gets it right. She follows a bunch of web 2.0 founders (all of whom I know personally, which made the reading experience kinda weird) and talks about how things are different from the dot-com bubble. I found myself nodding my head constantly, though I'm not sure this account would be enough to really get thru to an outsider. Nevertheless, I'm glad she went to so much effort to document the last several years and ...more
May 27, 2009 Kingsley rated it it was ok  ·  review of another edition
Profiles the rise of popular web 2.0 sites like Facebook and... well other sites looking to be like Facebook. I couldn't help but feel like Lacy got paid off by a lot of the characters in this non fiction as her lips are firmly planted on their asses but I did enjoy reading how the founders worked hard to turn their ideas into reality. If you are a huge Facebok/Andreesen fanboy, this is the book for you.
Jul 10, 2008 Jeremy rated it did not like it  ·  review of another edition
Recommends it for: Technology freaks
Lacy covers some interesting pioneers of the internet revolution, and up and comers in the Web 2.0 world. You learn a lot about the people behind the companies that everyone is talking about. Unfortunately, the writing is not good, and Lacy's explanations of technology and company dynamics are exceptionally poor.

So, to sum up, poor writing, terrible explanations, but about people with very interesting stories. Read at your own peril!
Jan 13, 2009 Pat rated it liked it  ·  review of another edition
It's obvvious from reading this book that the entrepreneurial community in Solicon Valley is incestuous. The book takes you through the people who started some of the bigger Web 1.0 companies that took off and, then, after they had made their money, these entrepreneurs started sponsoring the the companies building Web 2.0 environments. That's what happens when you have all of this success before 30, you don't know what else to do but try to top yourself.
May 10, 2009 Boco rated it really liked it  ·  review of another edition
Sarah is a disciplined writer. I know this because i follow her tweets which do not contain the clean reporting style she employs here. She has enjoyed great access to the techno elite over the years and she shares that access in this highly readable chronicle of the rise of Web 2.0. I stole that from the title. There is so much out there about Web 2.0, this is a great place to start reading about the movers and shakers from a highly credible, dialed in but still objective source.
Aug 08, 2008 Lauren rated it really liked it  ·  review of another edition
Recommends it for: geeks
Recommended to Lauren by: read about it in wired
Shelves: professional
This was a great book to read. As someone who uses most of the sites described in the book, and who had an inkling of an idea about who everyone was, I really enjoyed how the book pulled all the pieces together. I imagine it's like politics for political science folks or the royal family for history buffs. This is the same idea, but for geeks. Fun and fast read!
Jan 14, 2013 Cyndi rated it liked it  ·  review of another edition
I would like to have given this more stars but it was a bit of a slow read. Also, I wish I would have read this book when it came out (sometime in 2008) since some of the companies they spoke about have gone by the wayside, such as Digg and MySpace. All in all still an interesting book about the companies that were created from the second web "bubble".
Jul 23, 2013 Tom rated it liked it  ·  review of another edition
Excellent. Well-written overview of the Web 2.0 revolution, which was born from the ashes of the 1999's web implosion. Mainly the book focuses on a few key characters, and offers a nicely drawn sketch of what motivated these people, how they overcame adversity, and how they tried not to repeat the mistakes of the earlier Web wave. Terrific first book.
Read this to get a better historical understanding of Silicon Valley. Some very interesting context here, but beware, bits of this come off a little "fan-girl-esque"... I think her writing (and objectivity) has improved substantially since she wrote this book. Still, not many people can give you this type of inside scoop and perspective on the entrepreneurial culture in Silicon Valley.
Nic Brisbourne
I enjoyed this for it's tittle tattle Valley gossip and some stories about some of the personalities and their companies that I hadn't heard before. I've read books that taught me more though. Much more.
Aug 08, 2008 Mike rated it it was ok  ·  review of another edition
Could have done without the gratuitous sweater vest-bashing (I am a long-time sweater vest advocate, as are most accountants). Other than that, just OK... I felt it over-simplified many of the individuals and companies that were subject matter...
Ronghui Li
Jan 29, 2015 Ronghui Li rated it really liked it  ·  review of another edition
Many details about many funding moments of Facebook/Twitter/Digg/Slide. Unfortunately, there are many controversial stories that are quite different from what had been written in and .
Sep 08, 2008 Jany rated it liked it  ·  review of another edition
Very interesting. Gives a nice summary of the Valley and the bubble for those of us who weren't here during that time. The founders seem both larger than life and very accessible at the same time.

I blogged about it, so I won't go into huge detail:
Jun 09, 2009 Troy rated it liked it  ·  review of another edition
Recommends it for: software startup entrepreneurs & employees
Recommended to Troy by: Sarah Lacy
Informative behind the scenes book about the concerns and experiences of several Web 2.0 entrepreneurs. I could do without the name dropping of Silicon Valley hotspots, though, which had me sometimes wondering if I suddenly picked up a People magazine instead.
this is a fun book to read when you're in the thick of it - i dont think people outside the industry would understand or appreciate or get it. sarah lacy's overly dramatic retellings of these people's lives is really annoying.
Feb 23, 2009 Rose rated it it was ok  ·  review of another edition
Much more a gossip book about the personalities of first and second generation Silicon Valley entrepeneurs than about the development and growth of Internet commerce and Web 2.0. I wouldn't recommend it.
An interesting look at the rise of Web 2.0, and some of its major players. It's a lot more focused on the individuals than it is on the companies. I'd recommend it to web entrepreneurs and those interested in web entrepreneurship.

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