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

by Sarah Lacy

The captivating story of the mavericks who emerged from the dotcom rubble to found the multibillion-dollar companies taking the Web into the twenty-first century

Everyone has heard the story of the Internet Bubble. Beginning with Netscape’s IPO in 1996, billions flowed into Internet startups, and companies with no revenues and shaky business plans earned sky-high valuations on Wall Street. It was the era of paper millionaires, $800 office chairs, and Super Bowl ads for dotcoms. Then in 2000 the Bubble burst, with the NASDAQ losing 75 percent of its value and hundreds of companies closing up shop. It was all written off to “irrational exuberance,” and everyone moved on.

Once You’re Lucky, Twice You’re Good is the story of the entrepreneurs who learned their lesson from the bust and in recent years have created groundbreaking new Web companies. The second iteration of the dotcoms—dubbed Web 2.0—is all about bringing people together. Social networking sites such as Facebook and MySpace unite friends online; YouTube lets anyone posts videos for the world to see; Digg.com allows Internet users to vote on the most relevant news of the day; Six Apart sells software that enables bloggers to post their viewpoints online; and Slide helps people customize their virtual selves.

Business reporter Sarah Lacy brings to light the entire Web 2.0 scene: the wide-eyed but wary entrepreneurs, the hated venture capitalists, the bloggers fueling the hype, the programmers coding through the night, the twenty-something millionaires, and the Internet “fan boys” eager for all the promises to come true.

Genres: Business, Technology, Nonfiction, History, Entrepreneurship

304 pages, Hardcover

First published May 15, 2008

Reviews

[Michael Gerald · Rating 2 out of 5]

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 frenzy in the 1990s did. It argues that the Internet bubble of the 1990s was merely an aberration, and the second revolution in the first decade of the 21st century is here to stay.

Lacy attributes the success of this reinvigorated Web primarily to two things: open source software and peer-to-peer file sharing. The first gave the public not only the software but also the CODE that makes them run; people can work on it, tinker with it, and even make improvements on it - if you only know how. Examples are Linux and Mozilla. Open source software made the new innovations on the Web faster and cheaper.

The second phenomenon, peer-to-peer file sharing, challenged the big companies' monopoly of the products and services that previously they alone were able to purvey. The most famous - or notorious example - was Napster. Though it has unsavory implications on intellectual property, this system made it known that the demand from the consuming public for alternative access to these things exists. Together, these two phenomena effectively put an end to the Internet as solely the domain of geeks and academics. It is now more accessible to more people, just like how the assembly system and the Ford Model T made the car more affordable to Americans in the early 1900s.

However, there are also some flaws. The book only showed the supply side of the process: how the different Web prodigies came up with their ideas like Netscape, PayPal, LinkedIn, Digg, Facebook, Twitter, etc., their lifestyles, their quirks, their hard work. Sure, the author's access to the creators is revealing, but it would have been better if the demand side was also presented: how the public uses these services and platforms.

And there's this:

"Some people believe the more we socialize online, the bigger the rift is in the real-world social fabric. That interacting with each other via machines makes us more anti-social. Nothing could be further from the truth. The Web isn't a replacement for offline relationships: it's merely an efficient tool to keep in touch with people more easily, reconnect with friends and family once lost, or discover new friends that you may never meet in the real world. There are no online or offline friends: friends are friends."

Well, ten years of social networking, we know better. While Facebook and others are certainly beneficial in boosting our connectivity and relationships with people, the irony of Internet social networking is that, while most people have seen their "friends" increase, many people also found that their real-life interactions actually decreased. Yeah, sure, you have 5000 friends, but how many of them do you know personally or have even seen in the flesh? Do all of your "friends" bother to greet you on your birthday? Or even bother to read what you post?. Some friends. Maybe this phenomenon can be called "anonymous friendships" or "friendly indifference".

To be fair, the author mentions in passing the problem of online harassment, bullying, and fraud, problems that have profound consequences. Sadly, these problems have even led to murder and suicide.

The Internet is an amoral platform; it can be used for good or bad. Let us hope that the benefits from it would eventually outdo the ugly side. If that were to happen, then the coming of the Internet would be recognized as one of the most revolutionary and history-changing accomplishments of Man.

[Hayashi Sakawa · Rating 5 out of 5]

I really enjoyed reading it. This is the compelling narrative of the history-in-the-making told from an insider's point of view.

[Herve · Rating 4 out of 5]

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 if author Tracy Lacy (appearing in another post) is quite convinced it is a revolution.


It is a beautiful book because it shows once again the richness of individual connections. I have done below my illustration of it. Paypal and its founders appear to be at the center of this network. Fairchild had such a similar situation at the beginning of Silicon Valley in the sixties, Apple, Sun, Cisco thereafter.

Another interesting element is about investors. There has been a popular idea that web2.0 was not funded by venture capitalists anymore because the web2.0 business angels who were web1.0 entrepreneurs had learnt their lesson. The situation is more complex as the web2.0 financing shows. Greylock, CRV, Accel but also Benchmark and Sequoia are vey active. Finally, it shows again and again what entrepreneurs are: passionate, driven individuals and I can only advise reading the epilogue about Levchin’s childhood. Quite fascinating…

More on http://www.startup-book.com/2008/11/0...

[Rex · Rating 3 out of 5]

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 more.

One can't help thinking of Michael Wolff's "Burn Rate," the Web 1.0 equivalent, while breezing through this. That book was full of energy and wanted to be more than an MBA manual disguised as an anti-MBA manual.

But now I'm being too harsh. In short, this is a really good Business Week article, which is all it ever wanted to be.

[Jeremy · Rating 1 out of 5]

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!

[Kingsley · Rating 2 out of 5]

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.

[Kinman Li · Rating 4 out of 5]

Great stories about the main players in Silicon Valley. What they went through and how they got through it

[Samson Momanyi · Rating 2 out of 5]

Good

[Angad Singh · Rating 4 out of 5]

One of the best books for the Silicon Valley history enthusiast.

[Kwang Wei Long · Rating 3 out of 5]

good history from web 1.0 to web 2.0 era of the tech boom. from paypal to facebook and linkedin.
not much direct lessons to be gleamed. more of a recount.

[Robert · Rating 3 out of 5]

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 and error mixed with some early success that really rounds out the picture. The general feel of the book is that Sarah befriends or rather cozies up to the person she wants to write about and then throws soft ball questions their way. Even still, there was some interesting information in the book even if Sarah, who I have met, did not do much research in conjunction with the interviews and profiles in it.

Something else that I guess is worth pointing out is the fact that this book by Sarah follows the format of Michael Lewis's 'The New New Thing: A Silicon Valley Story' very closely. If you enjoyed that book then you will probably enjoy reading this book. Similarly, if you enjoyed reading this book you should definitely read Lewis's book.

[Rodrigo Rivera · Rating 3 out of 5]

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 Work viel interessanter ist und man es vorziehen sollte. Once You're Lucky, Twice You're Good ist zwar unterhaltsam aber man lernt eher weniger über die Fehler und Gründe hinter des Erfolgs der Web2.0-Startups. Weiterhin bevorzuge ich persönlich das Interview-Format von FaW und die Vielfalt der Gründer - nicht alle sind aus der Internet-Branche-. Außerdem ist Once You're Lucky zu kurz für mein Geschmack und beschränkt sich auf wenige Startups.

Dennoch ist das Buch gut und wenn man schon Founders at Work gelesen hat und ein bisschen Inspiration während der Konzeptionsphase seiner nächsten Startup sucht, sollte man sich dieses Buch kaufen.

[Rachel · Rating 3 out of 5]

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 second problem: Sarah Lacy admires her subjects too much to be a good observer. She loves getting into the parties and conferences, loves being the sympathetic listener to skater-boy CEOs, loves going to the coffee places where an idea for a website was hatched. The benefit of her enthusiasm is that almost everyone would talk to her, sometimes with surprising honesty. The problem is that biography is supposed to offer perspective the subject can't see. Lacy's book is closer to a series of short, ghost-written autobiographies.

[Travis · Rating 4 out of 5]

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 that I have heard over and over for the past 5 years, as all these geeks become millionaires.

If you're the kind of person that keeps up with what Google is doing or joining the ranks against the new Facebook design, you'll digg (hah!) this book.

[Mark Cheverton (scifipraxis) · Rating 4 out of 5]

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 more depth on the stories contained, although many of them still remain to be played out.

Overall a good read, shedding light on the renewed life in Silicon Valley with the rise of Web 2.0

[Chad · Rating 2 out of 5]

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 digerati and other tech-savvy folks will read, it explains some of the new technologies using oversimplified and inapt metaphors.

[Liam · Rating 4 out of 5]

"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, powerful applications from meeting the perfect mate to finding the perfect job. The Web would know you, and as a result what you would like." (145)

[Joseph · Rating 3 out of 5]

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 the people involved, and it makes me happy to reflect on living through this part of history.

[Pat · Rating 3 out of 5]

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.

[Boco · Rating 4 out of 5]

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.

[Cyndi · Rating 3 out of 5]

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".

[Tom · Rating 3 out of 5]

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.

[Natalia · Rating 3 out of 5]

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.

[Jany · Rating 3 out of 5]

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: http://janyxu.com/2008/06/09/lucky/

[Rose · Rating 2 out of 5]

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.

[Troy · Rating 3 out of 5]

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.

[Wendy · Rating 5 out of 5]

This book is amazing! Sarah Lacy is a true insider with access to so many of the people causing major change in Silicon Valley. She writes with enthusiasm and depth that reinforces the idea that this is a fantastic time to be living and working in the area. I can't wait for her next book.

[- · Rating 3 out of 5]

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.

3.5

[Nic Brisbourne · Rating 2 out of 5]

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.

[Ronghui Li · Rating 4 out of 5]

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 .