When I first heard Cal Fussman on Tim Ferriss in 2016, it inspired me to start traveling internationally. It opened me up to the world and I couldn’t be more grateful.
I wanted to meet Cal and thank him for sharing his stories. We got the opportunity to have breakfast in early 2020. We became fast friends and even shared Thanksgiving together a couple years back.
I share this to show how the most unlikely connections can result in the most fulfilling relationships.
Conversations like these inspire the communities I’m building. Learn more on my Now page.
Table of Contents
What I Learned From Watching a Master
Cal spent decades as a journalist interviewing everyone from Muhammad Ali to Mikhail Gorbachev. His gift isn’t knowledge. It’s questions.
What I noticed over breakfast was that he never asked a question he already knew the answer to. Every question was genuinely open. He wasn’t steering the conversation toward a destination. He was exploring.
Most people ask questions to confirm what they already think. Cal asks questions to find out something he doesn’t know. That distinction changes everything about what comes back.
I’ve tried to apply that ever since, in investor meetings, in first conversations with founders, in pretty much any room where the instinct is to perform instead of listen.
How It Changed How I Meet People
Before I met Cal, I would go into meetings with an agenda. A list of things I wanted to cover. A version of the conversation I was already running in my head.
After spending time with him, I started showing up differently. Fewer prepared questions. More genuine curiosity about what this specific person has seen that I haven’t.
The conversations got better immediately. Deals moved faster. Relationships went deeper.
The simplest thing I took from Cal: ask the question you’re actually curious about, not the one that makes you sound smart. The real question usually leads somewhere the other person has never gone before.
And that’s where the best conversations start.