Once You're Lucky, Twice You're Good - review

Readers of this blog will know I ordered the new Sarah Lacy book, 'Once You're Lucky, Twice You're Good' and it arrived about a week ago.

I finished it today on the flight to Perth - so thought I'd throw a bit of a review together for anyone who was interested and is maybe considering buying the book.

I really enjoyed reading this book. Lacy is a great writer and structures the book in a way that makes it hard to put down, and it's a good resource for those who pay attention to the Valley/SF Web scene and also for those with only a passing interest ... the core theme of the book seems (to me anyway) to be the underlying motivations of the leading Web 2.0 entrepreneurs and what drives them.

What drives them appears to be making the next shit hot product ... not VC or going public ... they want to create something that makes a difference to users. With that in mind, it's no surprise that the book mainly focusses on the development side of things rather than the real world, business element. Huge valuations are thrown around ($8b for Facebook, $200m+ for Digg, $500m+ for Slide) with no real justification of why these companies are valued in the way they are.

For someone on the business side, this was frustrating ... they talked about the YouTube valuation of $1.5b back in 06 but there is minimal explanation that right now YouTube is still struggling to monetise its audience and content.

The book revolves around a few main characters.

- Max Levchin. Slide CEO, paypal founder, angel investor ... all round Silicon Valley key player
- Marc Andreesen. Netscape co-founder, Mosaic founder, Opsware founder and now Ning
- Jay Adelson. Revision3 Chairman, Digg CEO, Equinix
- Mark Zuckerberg. Facebook CEO and founder
- Kevin Rose. Digg Chief Architect, Pownce, Revision 3 - Diggnation.tv
- Reid Hoffman. LinkedIn Chairman
- Sean Parker. Napster, Facebook
- Ben and Mena Trott. Six Apart
- Peter Thiel. Paypal Co-Founder, VC, Angel Investor
- David Sze. VC
- Evan Williams. Blogger founder, Twitter

Those familiar with the above list will know it's a mix of initial dot com guys who had successes and new blood. The theme that links them is that right now in the Valley things have changed - there is a contempt (or at least cynicism) around venture capital ... and there isn't a single minded goal/desire to take the company public.

With the already successful guys (Andreesen, Levchin, Williams) there is a desire to show their peers that their first success wasn't a fluke. For Levchin (who is probably the star of this book) there is almost a single goal to make sure Slide is more successful than Paypal. What Lacy misses is that potentially Slide is just a fad ... and that when you compare it to Paypal right now, it seems a little irrelevant. There are pages dedicated to Slides dedication to building Facebook apps like Top Friends and Horoscopes and 8 Balls ... which to me seem irrelevant when compared to a revolutionary payment platform. Maybe I'm missing something ... (edit: Lacy does mention within the book that perhaps Slide isn't the game changer PayPal was ... however in my opinion doesn't flesh this out near enough)

I really enjoyed reading about Digg and the Jay Adelson, Kevin Rose dynamic. Some of the best parts of the book are the two recounting the talks they'd had with other companies to acquire Digg - amongst them Yahoo, Newscorp and even Al Gore.

From reading this book, and being in San Fran earlier in the year, it is a very exciting time in the web world. Plenty of innovation, sure, but also realism. This book I think could do more to talk about the business reality of some of these Internet plays - I think at times Lacy seems to show a distaste for the 'blue shirt MBA guys' and admiration for the tech, coder types.

My thoughts are the two need to co-exist and great web businesses acknowledge this in all aspects of the business. Maybe I am missing what the general feeling is in the US right now ... but with the likes of Slide, Ning, Digg etc it seems the logic behind them is build a great product, generate a strong userbase and then monetise.

Problem is, there is no shortage of great web tools/properties with large audiences ... the problem that will force many of them out is not being able to properly monetise their audience. I think this is a valid challenge of Web 2.0 and one not being acknowledged ... especially if the new breed (or the old breed's new projects) are determined not to repeat the mistakes of the past.

I would even argue that smart Biz Dev guys are more important than ever now - and in short supply.

Still, I recommend this book to anyone wanting not only an insight into these companies, but an insight into where the web is heading.

Top 5 moments ...

1. The conditions (alleged) Mark Zuckerberg places on his girlfriend in terms of dates per week and how much time he gets to himself. Zuckerberg actually comes across as a bit of a douche in the book I think.

2. Kevin Rose talking about buy out talks with Al Gore.

3. That Ross Levinsohn - former head of Fox Interactive Media - wanted to buy Digg ... the Digg guys met with Rupert and the Newscorp bigwigs, Digg wanted to sell, Levinsohn was dead keen on the concept ... but an offer never came. Weeks later Levinsohn bailed from FIM ... you have to wonder what could have come out of a Myspace/Digg product.

4. Jay Adelson's description of his days at Equinix are actually quite sad ... you don't really know if it was naive optimism or gritty determination that kept him at a company that seemed determined to burn him.

5. Reid Hoffman. Seems like a good guy and potentially is sitting on the most valuable product of them all in LinkedIn

Buy from Amazon - http://www.amazon.com/gp/product/1592403824/ref=cm_cr_pr_product_top