We put a lot of trust into online shopping: sharing our names, addresses, and handing over money. In return, we have faith that the purchased item appears at our doorstep in a few days or weeks. That trust didn’t come easily. In 1995, we took our first steps out of the brick and mortar store to load our digital shopping cart.

Robert Spector reveals how Amazon.com’s business foundations are in data—and being early to the internet. Sandeep Krishnamurthy recounts the rise of eBay. Angela Robinson describes the technology that makes secure transactions and trustworthy e-commerce possible. Kartik Shastri shares how difficult it was to store and process consumer data. And Katie Wilson explains how some big tech companies are different from previous monopolies, but are following many of the same paths.

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