Squarespace: Anthony Casalena

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 nearly 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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Guy Raz interviews the world’s best-known entrepreneurs to learn how they built their iconic brands. In each episode, founders reveal deep, intimate moments of doubt and failure, and share insights on their eventual success. How I Built This is a master-class on innovation, creativity, leadership and how to navigate challenges of all kinds.New episodes on Mondays and Thursdays for free. Listen 1-week early and to all episodes ad-free with Wondery+ or Amazon Music with a Prime membership or Amazon Music Unlimited subscription.Get your How I Built This merch at WonderyShop.com/HowIBuiltThis