The Full Story of Julie Wainwright: From Pets.com CEO to Founding The RealReal

In this episode, Julie Wainwright shares the extraordinary story of her career — from leading Pets.com through its highly publicized collapse to founding and growing The RealReal into a billion-dollar company. She opens up about the lessons learned from failure, the grit it took to rebuild, and the early years of building a pioneering business around sustainability and luxury resale. Julie also reflects on taking The RealReal public, navigating life as a woman CEO in tech, and what she’s learned about resilience, reinvention, and purpose along the way. A powerful conversation about courage, conviction, and starting over.

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Chapters:
00:00 Intro
00:55 What Julie does for movement
05:00 Julie on fashion
08:10 How Julie shops for clothes
11:00 How TheRealReal started
14:30 What was the .com bust
20:45 Comparing the .com bust to current AI trends
22:20 How TheRealReal will integrate AI
28:55 Julie’s rise to CEO
35:55 How Julie navigated through the fall of Pets.com
40:55 How Julie dealt with criticism
44:03 Julie on being a woman in tech
51:05 Julie on taking risks
53:20 How Julie got the idea of TheRealReal
55:43 Was Julie always fashionable
1:01:43 What brands was TheRealReal prioritizing
1:03:20 What Julie had to figure out with the fashion industry
1:05:40 What were big turning points for TheRealReal
1:09:22 The first product Julie bought from TheRealReal
1:11:00 Stories about resellers
1:15:02 Julie on customer service
1:16:30 Julie’s reaction to TheRealReal IPO
1:18:40 Julie on getting fired
1:22:35 What Julie does now
1:25:25 Julie’s new book
1:26:00 Julie’s advice to her younger self