Episode Details

Episode Description:

Before Cal Fussman interviewed Muhammad Ali, Mikhail Gorbachev, Kobe Bryant, Serena Williams, Al Pacino, Robert De Niro, and hundreds of other extraordinary people, he spent nearly a decade traveling the world without much of a plan.

He would get on buses without knowing where they were going. He had little money, so he often needed to strike up a conversation with a stranger and build enough trust to be invited home.

That became his training.

Cal learned to read people, listen closely, follow curiosity, and ask the question that could turn a stranger into a friend. Those same skills eventually became the foundation of his celebrated What I’ve Learned interviews for Esquire.

In this first conversation between James and Cal, they explore why questioning is becoming more valuable in a world overflowing with answers. Google can give you information almost instantly. What it cannot necessarily give you is the question that changes how someone sees their own life.

Cal explains why television interviews often fail to create real connection, why canned questions produce canned answers, and why he eventually stopped bringing a written list of questions into interviews.

Preparation still matters. But once the conversation begins, the interviewer has to listen.

James and Cal also talk about curiosity as a skill that gets suppressed over time. Children ask questions constantly. Adults often stop because asking reveals that they do not know something. Cal argues that the process can be reversed: curiosity can be deliberately rebuilt.

They break down some of Cal’s most memorable interviews, including the question that opened up Mikhail Gorbachev, what he learned from Larry King and Oprah Winfrey, and why a seemingly strange question to Dr. Dre can reveal far more about passion than asking someone directly whether they work hard.

The conversation eventually turns back on James. Cal becomes fascinated by James’s ability to simplify ideas into repeatable formats, and the two start brainstorming how questions themselves could become tools for hiring, parenting, relationships, education, and business.

Underneath all of it is a simple idea:

A better question can lead somewhere you never expected to go.

Editorial Note:

This is a From the Archive episode and the first interview between James Altucher and Cal Fussman. The original episode, #324: “The Art of a Great Question,” was published March 5, 2018.

References to Cal being new to podcasting, Big Questions just getting started, his role at Esquire, the state of magazines and terrestrial radio, and podcasting being in its “second inning” reflect the original recording period.

Several people discussed in the episode have since died, including Kobe Bryant, Larry King, and Mikhail Gorbachev. Their interviews are discussed here in the context of Cal’s career and his experiences with them.

Cal’s Big Questions podcast remains active, and his work today continues to center on questioning, human connection, leadership, and increasingly the future of work in the age of AI.

What You’ll Learn:

• How a decade of unplanned travel taught Cal to connect with almost anyone.
• Why Cal believes great questions have become more valuable in a world overflowing with answers.
• How asking questions helped turn a young sportswriter into one of the world’s best-known interviewers.
• Why Cal prepares extensively but throws away his written questions once the interview starts.
• How curiosity gets suppressed as we grow older—and how to deliberately rebuild it.
• Why asking the heart before the head can produce a completely different conversation.
• What Cal learned about interviewing from Mikhail G