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A Bit of Optimism

The Confidence Conversation We Need to Have with Scott Galloway

A Bit of Optimism

The Optimism Company from Simon Sinek

Education, Business, Self-improvement, Careers

4.82.3K Ratings

🗓️ 24 February 2026

⏱️ 55 minutes

🧾️ Download transcript

Summary

Scott Galloway and I don’t always see the world the same way, but our friendly debates almost always lead us back to common ground. It’s probably why we enjoy talking to each other as much as we do. If you haven’t heard my friend Scott’s name before, he’s known for being brilliant, provocative, and unapologetically himself. He’s a professor at NYU Stern School of Business, entrepreneur, bestselling author, and larger-than-life social commentator. In recent years, his work, which includes his new book Notes on Being a Man, has explored the challenges facing men today, from loneliness and dating to purpose and identity. Scott and I have different views on what “healthy masculinity” looks like. He’s not afraid to say things during this podcast that might ruffle some feathers. But inevitably, the conclusions we get to are introspective, vulnerable, and often universal. That’s certainly true for one revelation we share: confidence matters. Not the loud, performative kind. The real kind. The kind that helps people risk rejection, build meaningful relationships, and show up more generously in the world. In this episode, Scott and I talk about the “masculinity crisis,” why young people are struggling to connect, how purpose outlasts happiness, and why masculine and feminine traits are complementary rather than competing. We explore the need for good social risks like leaving the house, meeting people, pursuing relationships, and hearing “no,” and why confidence is less about ego and more about security, kindness, and connection. This is a conversation between two opposites who challenge each other, listen deeply, and ultimately agree that building real confidence may be one of the most important skills we can teach the next generation. This… is A Bit of Optimism. --------------------------- If you want to read Scott’s new book Notes on Being a Man, head to: https://www.simonandschuster.com/books/Notes-on-Being-a-Man Check out Scott’s podcast “The Prof G Pod”: https://www.youtube.com/c/TheProfGShow-ScottGalloway You can also watch his podcast “Pivot with Kara Swisher and Scott Galloway”: https://www.youtube.com/@pivot To stay up to date with all of Scott’s work, head over to: https://www.profgalloway.com/ ---------------------------

Transcript

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0:00.0

I had some fucked up sense of masculinity when I was younger. I never showed my emotions. Didn't cry

0:03.2

between the ages of 29 and 44. Didn't laugh out loud. Now I purposely try to train myself

0:08.0

into laughing out loud because 50% of having a good sense of humor is appreciating other people's

0:14.1

cleverness. I think learning to laugh, that's an expression of something you're feeling on the inside,

0:19.1

I would argue, is vulnerability.

0:21.8

I think when you're a younger man, sometimes you have this belief that recognizing someone else

0:29.3

is funny, acknowledging someone else's success, somehow takes away from your success.

0:34.8

Yeah, yeah, yeah.

0:35.8

That it's a zero-sum game.

0:37.3

And what you realize is you get older is the guy who says to another guy, wow, you're so impressive or laughs at his joke and says, wow, that was really funny. That's confidence. Yes, you're describing confidence. It's 100%. That's all it is. Most of us have at least one friend who's got a total opposite personality to us.

0:56.0

On paper, it shouldn't work.

0:58.6

But for some reason, it just does.

1:01.9

That's me and Scott Galloway.

1:03.8

Let's cause some trouble.

1:05.4

If you don't know, Scott, he's a force of nature.

1:08.2

A professor, entrepreneur, podcaster, best-selling author,

1:11.3

who's built a reputation as a provocative social commentator, unafraid of triggering his audience,

1:16.8

or me, or anyone listening to this podcast.

1:20.9

And I'll get shit for this.

1:22.4

Recently, the masculinity crisis has been one of Scott's main focuses, which inspired his new book Notes on Being a Man.

1:30.0

This also served as the starting point for our debate. I mean conversation.

1:35.1

Yes, we have very different ideas about healthy masculinity, but we agree on one thing.

...

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