Jessica Livington's recent book, Founders at Work, is a series of a interviews with successful technology entrepreneurs from the last twenty-five years. The format is a refreshing change from much of the tech press that focuses exclusively on launches, acquisitions, conferences and petty feuds. Instead Livingston, a partner at Y Combinator, shines the spotlight on the behind-the-scenes struggle to create something new and valuable. So many of the boiled-down lessons from successful entrepreneurs (ex. "focus on customers", "make it easy to use") are so common sensical as to be of little value since the devil is in the execution. Which is why reading the actual stories of their challenges and strategies is so engaging. A few highlights from the great collection of interviews:

  • For the Paul Graham fans out there, it includes the most detailed telling of the Viaweb story I've read. Like many of founders' stories where you know the happy ending, their path was fraught with near fatal events such Robert Morris summering at DEC and struggles with investors. It's easy to spot the roots for much of the advice Graham now dispenses, such as working out of an apartment instead of an office, startup deals often falling through, or having a co-founder.
  • Evan Williams tells how Blogger was the second idea for Pyra, and how they came to focus on their pet project, leaving their original product behind (history repeats itself, it seems). Also he describes the painful days running Blogger after laying off the rest of the employees and putting out the fires himself.
    That was a lot of just day-to-day, by-the-skin-of-my-teeth stuff for several months...Then there is another part going on around this time that I can't talk too much about. Suffice it to say my former teammates didn't all go away happy, and I spent almost as much money on my lawyer in 2001 as I paid myself.
  • Phil Greenspun's interview provides a detailed description of his view on the rise and fall of ArsDigita. Livingston does not inject herself into the interview (which more interviewers should emulate) and asks open-ended and non-confrontational questions. The closest thing comes from the Joel Spolsky interview that directly follows Phil's, where he veers from PhilG for blaming the ArsDigita flameout soley on the VCs and not on the huge market downturn that happened in early 2001. Spolsky says of ArsDigita,
    ...I think they probably think that it didn't work for them because of the VCs came in and mismanaged it, but actually all the other businesses that looked like their business failed at the same time. Even with good management, it's likely that their consulting business would have collapsed as ours did at that time.
  • I agree with Guy Kawasaki that James Hong is the funniest interview in the book. Certainly HotOrNot is a little more frivolous than most, but the story of how they survived massive, viral growth and how to carved out a successful business from the site is entertaining.

Update: Jessica Livingston spoke at Google about Founders at Work, and boils down some of the themes she found conducting her interviews, and what companies can learn.