Harper Reed is one of the world’s foremost thinkers on data and digital innovation. He served as the CTO of Obama’s re-election campaign and was also one of the founders of Threadless.com. His latest company, Modest, inc, was recently acquired by Paypal, where he is now working to figure out the future of commerce. Over dinner at Soho House in Chicago, we talked about digital bias and the stubborn persistence of paper, why technology is best used as a force multiplier of people power, the quantification of marketing and how smarter tools replace the need for experts, reactionary interfaces and why retailers are afraid of their customers, why iTunes credit is more meaningful to kids than cash, the power of ‘undo’ in e-commerce, and the link between local infrastructure and global innovation.