Book Review – Once You’re Lucky, Twice You’re Good

On the recommendation of my friend and colleague Jeremy Lichtman, I just completed the book “Once You’re Lucky, Twice You’re Good” by Sarah Lacy, which is about the rebirth of Silicon Valley and the development of what is now known as Web 2.0. It was an excellent book, prompting me to write this review.

As an aside, while I am a passionate reader, often reading as many as 5 books simultaneously, I have never written a book review before. Hopefully, however, this will become a habit, and I will try to write a book review at least once per month in the upcoming months.

The book was a fascinating read. Sarah has successfully described not only the success of the various entrepreneurs who were actively developing new sites in the post-dot com era, but also their motivation, and what differentiates them from their predecessors. The book provided insight into the psychology of the new generation of developers, their past, their motivators, and their ambitions.

The book was not cut and dry, but an excellent interactive read. Modeled after the websites developed by the subjects of the book, Sarah engages her readers in the decisions of her subjects, the debates they held with themselves, the factors involved which motivated them to succeed.

She writes about Max Levchin, the founder of PayPal and Slide, and an investor in Yelp. She talks about where he came from, what motivated him to succeed at that level. She discusses his fears, debates, and decision-making process. Read about Mark Zuckerberg, the founder of Facebook, and how he turned down an offer of $1 billion from Yahoo in June 2006 (a wise move, as it would turn out, with a current estimated value exceeding $15 billion). Read about the people who helped them, who were there to teach them the lessons they learned during the dotcom bubble.

All in all, this was a fantastic book, and a must read for anyone who is thinking of developing a piece of software or an online platform, as it will teach you many of the lessons that have been learned during the last decade.