#218 CEO Etsy, Josh Silverman: Second Acts

Guest: Josh Silverman, CEO of Etsy

When Josh Silverman joined the board of Etsy, he had one condition: “Don’t ask me to the be the CEO.” And technically, they didn’t ask. One day, he got a phone call informing him the board had elected him as the new CEO, just days before an earnings miss. He knew the odds were against him — layoffs would be necessary, and “I was going to have to be the villain” — but decided to say yes out of a sense of duty to Etsy’s users and workers. “If I can be helpful, I have a responsibility to do it,” Josh says.

00:00 Introduction
00:07 Energy management
02:03 Meetings
09:53 Etsy's strategy
13:43 Learning to delegate
17:34 Setting an example
25:14 Evite's rise and fall
29:04 Self vs. company
32:05 Legacy
36:29 Control and agency
40:13 Joining Etsy's board
43:21 Becoming CEO
49:18 Culture shock
51:17 "We need you, trust us"
55:03 eBay and Skype
1:01:46 Pushed out
1:05:40 Accountability and family
1:09:16 Time horizons
1:11:28 Gen AI-supported art
1:14:17 Who Etsy is hiring, what “grit” means to Josh
1:15:17 Outro

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