The Confidence Conversation We Need to Have with Scott Galloway

368 snips

Feb 24, 2026

Scott Galloway, NYU professor, entrepreneur, and bestselling author, discusses masculinity, confidence, and why real confidence is about security, kindness, and connection. He and Simon debate social risk, dating dynamics, digital distortions, and practical fixes like service, better wages, and parenting that builds resilience. Short, candid, and provocative conversation.

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INSIGHT

Fearless Public Risk Builds Opportunity

Scott Galloway attributes much of his success to being less afraid of public failure and taking frequent public risks like starting businesses and podcasts.
He views public failure as a low curb that rarely matters and trains himself to risk rejection in jobs, dating, and ventures.

INSIGHT

Complementary Sex Differences Matter

Scott argues biological and cultural differences produce tendencies: men trend toward risk-taking and women toward observation and caregiving, and both are valuable.
He warns against pathologizing masculinity wholesale and urges celebrating masculine strengths while demanding equal opportunity.

ADVICE

Give Boys A Practical Aspirational Code

Teach boys an aspirational masculine code: economic viability, protection, and practical softness like noticing partners' lives.
Galloway prescribes concrete actions: gain marketable skills, err on side of protection, and practice noticing and follow-up.

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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.

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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/

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