025: Paula Scher – The Greatest Risk Is Not Taking One

025: Paula Scher – The Greatest Risk Is Not Taking One

If you’re not taking risks, you’re standing still. But the moment that you experience any success, people start asking you to repeat yourself. So how do you keep evolving while also making a living? In this conversation with legendary graphic designer Paula Scher, we...
019: Matias Corea – The Road Less Traveled

019: Matias Corea – The Road Less Traveled

We all have dreams of quitting our jobs and just taking off. But how do you rationalize it? And when does leaping into the unknown outweigh the value of sticking to your routine? In this episode, I talk with designer, entrepreneur, and adventurer Matias Corea about...
009: Tyler Cowen – The Quiet Dangers of Complacency

009: Tyler Cowen – The Quiet Dangers of Complacency

Few authors have impacted my worldview more than Tyler Cowen. His latest book, The Complacent Class, fundamentally changed my understanding of what it means to be a risk-taker — and what it means to be American. In this episode, Tyler and I unpack the factors that are...
004: Kim Chambers – Calculated Risk, Stretch Goals, and Sharks

004: Kim Chambers – Calculated Risk, Stretch Goals, and Sharks

Risk-taking is often portrayed as a matter of bold decisions and brash actions. But what if it’s actually more incremental and calculated than the stories we tell ourselves? In this episode, I interview world record-breaking marathon swimmer Kim Chambers, who has...