B-Schooled Podcast Episode #310: Josh Silverman on Evite, Skype, and Turning Around Etsy

B-Schooled

On the newest B-Schooled episode, Stacy Blackman sits down with Josh Silverman, Executive Chair and former CEO of Etsy. Their Paths Less Traveled conversation traces a career built on choices almost nobody else would have made. Josh entered college as a theater major and graduated with no job. He slept on couches in Washington until he talked his way into a $13,000-a-year Senate mailroom job. Decades later, he’d led Skype, run a $13 billion business at American Express, and spent nearly nine years as Etsy’s CEO, turning a stalled marketplace into a household name.

Stacy Blackman and Etsy Executive Chair Josh Silverman on a video call for B-Schooled Podcast Episode #310.

Stacy, who has known Josh for years, walks him back through the moves in between. They talk about why he shared a meal with nearly every one of his 316 Stanford GSB classmates. Then there’s the panicked Thanksgiving discovery that turned his own startup plan into Evite. Josh is candid about the dot-com crash, and about what it feels like when the company people remember as a hit didn’t feel like one at the time.

Josh also shares the three questions he asks before taking any new role. That simple test has pointed him toward jobs most people told him to turn down. For applicants who picture the MBA as a ladder to one clearly marked first job, his story is a reminder that it can be the foundation for decades of unexpected moves.

Listen to B-Schooled episode #310 here, or on your favorite podcast app.

B-Schooled is available on most major podcast apps, including:

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Prefer to read? View the transcript here.

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