Bill Ready (Pinterest) on Social Media’s “Big Tobacco” Moment, Growing Pinterest to 578M Users, and What Gen Z Really Wants

Bill Ready has never been afraid to make big bets—and at Pinterest, those bets are paying off. Since becoming CEO, he’s doubled down on building a healthier internet: one where all accounts under 16 are private by default, AI is tuned for positivity, and users come away inspired instead of exhausted.

Today, Sammi sits down with Bill to trace his journey from his father’s auto shop in Kentucky to the helm of PayPal, Google, and now Pinterest. They dig into the headline-making decisions that reshaped Pinterest’s future, the rise of Gen Z shopping habits, and how collaborations like Pinterest Predicts with Emma Chamberlain’s coffee brand are setting cultural trends.

If you want a look at what social media can be when it prioritizes progress over doomscrolling, this conversation is it.

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00:00 Bill Ready’s Social Currency 

02:05 Early Lessons from the Auto Shop 

05:31 The Controversial Decision to Turn Accounts Private for Users Under 16 

06:43 Tuning AI for Positivity 

26:10 Evolving the Pinterest Shopping Experience 

31:58 Pinterest's Unique Approach to Video Content 

34:24 Inclusive AI Tools and Driving User Engagement 

41:44 How Pinterest Shapes and Predicts Trends 

51:45 Bill’s Systems for Success

53:14 Social Currency Corner 

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