Henrick Johansson sits down with product design leader Simon Corry in New York City for a wide-ranging conversation about creativity, compliance, velocity, and what it really takes to build products people trust.

Simon traces his unlikely path from British art school and Royal Mail to Amsterdam’s creative scene, where the early ideas behind WeTransfer grew out of a very real problem: agencies needed a simple, trustworthy way to send large files without accounts, passwords, or friction.

From there, the conversation moves through Facebook, anonymity, AI regulation, and Simon’s current work at Ramp, where speed, recruitment, education, and culture are central to scaling without becoming slow.

At the heart of the interview is a tension every modern company faces: how do you move fast without losing responsibility, customer empathy, or trust?

Simon argues that great teams win by listening closely, staying willing to be wrong, and avoiding the gatekeepers that slow progress down.

This is a conversation about design leadership, startup culture, product velocity,

AI, compliance, and the human judgment required to build companies that can move quickly without breaking what matters.

Featuring stories from WeTransfer, Facebook, Royal Mail, and Ramp, this episode is for anyone interested in product design, leadership, startups, fintech, compliance, AI, and the future of fast-moving teams.

What happens when you sit down for a simple game of chess… and end up in a deep conversation about prison, rules, and human nature?

Henrick Johansson asks the questions nobody else will.

Due Diligence is a new podcast featuring sharp, satirical conversations with founders, operators, and investors in tech.

One guest a week. All on the record.

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