In 2009, Anthony Casalena was listening to a lot of podcasts, especially one called “This Week in Tech,” a round table where tech reporters gathered to talk about things like Farmville, Foursquare and the iFart app.
Though the website building business he started in his dorm room six years before had yet to make a profit, he decided to make a big bet. He spent around $20,000 for an ad on the show to tell listeners about Squarespace.