Where Is Simon Going? with journalist Cal Fussman

A Bit of Optimism

The Optimism Company from Simon Sinek

Business, Education, Careers, Self-improvement

4.8 • 2.3K Ratings

🗓️ 13 May 2025

⏱️ 50 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

Sometimes in life, we must stop and ask ourselves, “Where am I you going next?” Other times, it’s more fun to do a podcast takeover. No one has ever interviewed me quite like Cal Fussman. Cal has a gift – he pulls things out of you that you didn’t even know were there. A prolific Writer At Large for Esquire, Cal has interviewed legends like Muhammad Ali and Mikhail Gorbachev, and he’s the host of the podcast Big Questions. So, to mark 15 years since writing Start With Why, I invited Cal to take over my podcast and ask me the questions I don’t usually get asked. Cal did get me to open up in this conversation, but not in the way you might expect. We talk about where I’ve been, where I’m going, the infinite game, creativity in AI…and why I’ve become so obsessed with friendship lately. This…is A Bit of Optimism For more on Cal and his work, check out: Big Questions with Cal Fussman

Transcript

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0:00.0	The common thread in all of my work was a friend there to support me, was a friend there to hold me up,
0:07.2	and I know who those people are. It's Jen, it's Johnny Quest, it's Johnny Bravo, it's Kendra, writing about friendship now, because it's my, it's going to bring me to tears.
0:19.6	It's a letter of gratitude. I'm writing this
0:23.1	book to say thank you. Hi, I am not Simon Sinek. I'm Cal Fussman, and today I'm taking over for
0:33.5	Simon to interview Simon. It's been 15 years since the release of Start with Why,
0:39.8	and so we thought it'd be fun to flip the script
0:43.1	and let me interview Simon about where we've been
0:46.8	and where we're going.
0:48.5	I first met Simon in 2019 when he came on my podcast,
0:53.6	and that conversation was a feast of epiphanies.
0:57.6	Today, I came back for more, but my overriding question is, where is Simon going?
1:06.8	And you're going to find out, but in a most circuitous way.
1:11.4	You're going to hear two older gentlemen who are not technologists talk about AI.
1:18.3	You're going to hear some things that may surprise you, even if you are a technologist.
1:23.9	And in the end, you're going to run into the moment where Simon answers the question.
1:30.3	This is where he's going.
1:33.1	And of course, it contains a bit of optimism.
1:40.4	The takeover!
1:43.1	I'll let Simon explain.
1:45.0	So a bunch of years ago, the Infinite Game had just come out, and I was doing the podcast tour, interview tour, and I was invited onto your show, onto your podcast.
1:57.0	You got more out of me than probably any interview I've ever done before and probably since.
2:02.8	There were new ideas that were coming out, revelations.
	...

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