A quick digest:
Web Analytics 2.0 by Avinash Kaushik
Maybe not the sexiest book to jump start the list, but I gotta admit, even though he's the digital marketing evangelist for the company that helps pay my bills, Kaushik's notes give a solid foundation on how to translate the sea of daunting web metrics (also known as clickstream analysis) into actionable insights driven by data. I once took a course in college that focused on financial analysis by showing how consumer behavior can be better understood through a company's balance sheets, income statements and cash flow statements (example: looking at a retail company's inventory turnover in order to show where consumer demand is highest). Kaushik's teachings are basically the digital/online version of such financial analysis. If you're interested in the topic, I also highly recommend his blog.
What Technology Wants by Kevin Kelly
As co-founder of Wired and Cool Tools, I'd say that Kevin Kelly knows a thing or two thousand about technology. His book views the industry not as a business driving growth lever for a country's GDP, but instead Kelly examines technology as a separate breathing entity, as something that wants to make your life better. He's optimistic for sure, but he also takes the reader through his adventures in Amish Pennsylvania where he, coincidentally, found himself liberated in the technology starved communities. The book couldn't be more macro in theme.
So Good They Can't Ignore You by Cal Newport
My full run down is here. But to be concise, Newport's book argues that the passion for your job doesn't come instantly and it only comes after patiently uncovering skills and tasks that one can perform really well. The book was an incredibly fast read, but I can't exactly vouch for the effectiveness of his advice. I'll let you know in ten years though.
Bossypants by Tina Fey
Two big takeaways here. The first is that Tina Fey's learnings in improv largely inform how she carries out her day-to-day operations, from writing scripts to parenting a child. Isn't that poetic? The second takeaway is that I'm one of the few men who actually started (and one of the even fewer who finished) this book and I'm seriously hampering my dating life by broadcasting this here. Still though, I found the read worthwhile.
Tubes: Journey to the Center of the Internet by Andrew Blum
I wanted to love this. I really did. If you're curious, I suggest looking up "internet" on Wikipedia and saving yourself the time.
Not Fade Away: A Short Life Well Lived by Laurence Shames
If you've got 'em, hit me with your recommendations in the comments!