Like many classic technology stories, Squarespace started in a college dorm room. In 2003, 21-year-old Anthony Casalena created a website-building tool for himself. But after hearing some positive feedback from friends, he decided to put the tool online and start a business. For years, Anthony ran Squarespace almost entirely on his own but the stress took a toll and he reached the limits of what he could accomplish by himself. The journey to hiring a staff and scaling the company had its own set of growing pains for Anthony, including difficulty letting go of control, and learning how to manage other people. Today, Squarespace has grown to more than 800 employees, and valued at $1.7 billion. PLUS in our postscript "How You Built That," how Kate Westervelt took an overwhelming experience and turned it into a gift box for new moms – filled with essential items women need to recover from childbirth.

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