Uploaded February 2026 | Updated September 2026, 2 weeks ago
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: simonandschuster.com/books/Notes-on-Being-a-Man
Check out Scott’s podcast “The Prof G Pod”: youtube.com/c/TheProfGShow-ScottGalloway
You can also watch his podcast “Pivot with Kara Swisher and Scott Galloway”: youtube.com/@pivot
To stay up to date with all of Scott’s work, head over to: profgalloway.com
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Simon is an unshakable optimist. He believes in a bright future and our ability to build it together.
Described as “a visionary thinker with a rare intellect,” Simon has devoted his professional life to help advance a vision of the world that does not yet exist; a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are and end the day fulfilled by the work that they do.
Simon is the author of multiple best-selling books including Start With Why, Leaders Eat Last, Together is Better, and The Infinite Game.
+ + +
Website: simonsinek.com
Live Online Classes: simonsinek.com/classes
Podcast: apple.co/simonsinek
Instagram: instagram.com/simonsinek
Linkedin: linkedin.com/in/simonsinek
Twitter: twitter.com/simonsinek
Facebook: facebook.com/simonsinek
Simon’s books:
The Infinite Game: simonsinek.com/books/the-infinite-game
Start With Why: simonsinek.com/books/start-with-why
Find Your Why: simonsinek.com/books/find-your-why
Leaders Eat Last: simonsinek.com/books/leaders-eat-last
Together is Better: simonsinek.com/books/together-is-better
+ + +
#SimonSinek
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: simonandschuster.com/books/Notes-on-Being-a-Man
Check out Scott’s podcast “The Prof G Pod”: youtube.com/c/TheProfGShow-ScottGalloway
You can also watch his podcast “Pivot with Kara Swisher and Scott Galloway”: youtube.com/@pivot
To stay up to date with all of Scott’s work, head over to: profgalloway.com
+ + +
Simon is an unshakable optimist. He believes in a bright future and our ability to build it together.
Described as “a visionary thinker with a rare intellect,” Simon has devoted his professional life to help advance a vision of the world that does not yet exist; a world in which the vast majority of people wake up every single morning inspired, feel safe wherever they are and end the day fulfilled by the work that they do.
Simon is the author of multiple best-selling books including Start With Why, Leaders Eat Last, Together is Better, and The Infinite Game.
+ + +
Website: simonsinek.com
Live Online Classes: simonsinek.com/classes
Podcast: apple.co/simonsinek
Instagram: instagram.com/simonsinek
Linkedin: linkedin.com/in/simonsinek
Twitter: twitter.com/simonsinek
Facebook: facebook.com/simonsinek
Simon’s books:
The Infinite Game: simonsinek.com/books/the-infinite-game
Start With Why: simonsinek.com/books/start-with-why
Find Your Why: simonsinek.com/books/find-your-why
Leaders Eat Last: simonsinek.com/books/leaders-eat-last
Together is Better: simonsinek.com/books/together-is-better
+ + +
#SimonSinek
