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The Confidence Conversation We Need to Have with Scott Galloway | A Bit of Optimism

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/ + + + 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: http://simonsinek.com/ Live Online Classes: https://simonsinek.com/classes/ Podcast: http://apple.co/simonsinek Instagram: https://instagram.com/simonsinek/ Linkedin: https://linkedin.com/in/simonsinek/ Twitter: https://twitter.com/simonsinek Facebook: https://www.facebook.com/simonsinek Simon’s books: The Infinite Game: https://simonsinek.com/books/the-infinite-game/ Start With Why: https://simonsinek.com/books/start-with-why/ Find Your Why: https://simonsinek.com/books/find-your-why/ Leaders Eat Last: https://simonsinek.com/books/leaders-eat-last/ Together is Better: https://simonsinek.com/books/together-is-better/ + + + #SimonSinek

Scott GallowayguestSimon Sinekhost
Feb 24, 202654mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. SG

    I had some [censored] up sense of masculinity when I was young where I never showed my emotions, didn't cry between the ages of 29 and 44, didn't laugh out loud. Now I purposely try to train myself into laughing out loud because 50% of having a good sense of humor is appreciating other people's cleverness.

  2. SS

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

  3. SG

    I think when you're a younger man, sometimes you have this belief that recognizing someone else is funny, acknowledging someone else's success somehow takes away from your success.

  4. SS

    Yeah, yeah, yeah.

  5. SG

    That it's a zero-sum game, and what you realize as 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.

  6. SS

    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. On paper, it shouldn't work, but for some reason it just does. That's me and Scott Galloway.

  7. SG

    Let's cause some trouble.

  8. SS

    If you don't know Scott, he's a force of nature, a professor, entrepreneur, podcaster, bestselling author who's built a reputation as a provocative social commentator, unafraid of triggering his audience, or me, or anyone listening to this podcast.

  9. SG

    And I'll get [censored] for this.

  10. SS

    Recently, the masculinity crisis has been one of Scott's main focuses, which inspired his new book, Notes on Being a Man. This also served as the starting point for our debate. I, I mean conversation. Yes, we have very different ideas about healthy masculinity, but we agree on one thing: confidence is the thing, and the question is, how do we help people build their confidence? Real men can listen, grow, disagree with respect, and still find common ground, just like me and my masculine friend, Scott. This is A Bit of Optimism. You were a business guy.

  11. SG

    Right.

  12. SS

    Then, then you were a teacher.

  13. SG

    Right.

  14. SS

    And now you've sort of taken on a larger-than-life presence as a podcaster, but n- also some social commentator. What's happening in your head? Are you growing up? Are you maturing? What philosophies have you completely abandoned? Is it age? Is it wisdom? Like, what's the thing that took you from there to here?

  15. SG

    It's a generous question. I, I think a couple things are driving me. Uh, one, I'm an atheist, and I think that really soon nobody we know or love is gonna remember us or be remembered, and so why wouldn't you try and live your life to the fullest and speak your mind and say things you're thinking but you're worried about being shamed, but you think that they're right? So I'm trying to live my life fearlessly. I always say that my goal is to live my life like I'm dancing with no one watching.

  16. SS

    Yeah.

  17. SG

    I think it's important to reverse engineer your success to things that weren't your fault. Like, I'm not a humble person. We've talked about this. I think I'm a fucking monster. I think I'm in the top 1% of grit and hardworking and creative. But that puts you in a room the size of Germany. That puts you in a room of 75 million people. When I look back on the things that have resulted in a lifestyle my parents couldn't have dreamt of in terms of economics or influence or interesting friends and peers, it's, one, the irrational passion for my wellbeing and my mother. So I try to think about mentoring young men and finding programs that support and show young people value. Two, the University of California. I got Pell Grants. I got to go to UCLA when the admissions rate was 76%. This year it'll be 9%. I got to go to graduate school at Berkeley with a 2.27 GPA from UCLA for basically no money, so I'm very involved. I spent a lot of money, for me at least, on, uh, access or broadening access to state-supported education.

  18. SS

    Yeah.

  19. SG

    People say, "What's the secret of your success?" For me, it's pretty straightforward, and that is I have been less afraid of public failure than most people. When you put out a podcast and you start a business, you're risking public failure.

  20. SS

    Yeah.

  21. SG

    When you express, "I wanna be better friends with Simon Sinek," that's a certain amount of public failure and exposure.

  22. SS

    Yeah.

  23. SG

    When you approach a strange woman and express romantic interest, you're setting yourself up for public failure. Most of my businesses have failed, but what I've been good at is, is risking public failure, and I wanna do more of that because if you think about the real obstacle between most people in a democratic society with the prosperity Americans enjoy and success or a better life, it's their fear of public failure.

  24. SS

    Yeah.

  25. SG

    And what I've learned is the fear of public failure is a curb that is two inches high and really doesn't fucking matter. If you start a business and it doesn't work, people go, "Oh, it didn't work," and then they go back to thinking about themselves. If you approach a woman and express interest and she's not interested in you and you're respectful, you're both gonna be just fine.

  26. SS

    Yeah.

  27. SG

    So I'm trying to be fearless, and I'm trying to also think about how I help or contribute to the things that gave me an irrational amount of success.

  28. SS

    I have a friend, she's a, a female entrepreneur, who believes, and there's a caveat at the end, but she believes that men make better entrepreneurs than women. And she came to this belief because she said when we're young, traditional roles still apply where men have to be the social initiators for the most part. So, you know, the boy has to ask the girl to the prom. Those conventions still exist, and so men from an early age, boys from an early age, have to build up the courage to ask, get shot down, ask again, get shot down, ask, get shot down. And so when they grow up and they join the business world, they become more comfortable trying, get shot down, sales pitch, get shot down. And her, her attitude is that, that, that muscle, that grit, that fearlessness is, is cultivated young.And the caveat now is now in a world where everybody seems to have re- retracted from taking social risk, or too many people have, and you can sit in your room and swipe right.

  29. SG

    Yeah.

  30. SS

    And you never feel rejected. You can just assume they didn't see your picture or whatever it is, that that muscle isn't building for anybody.

Episode duration: 54:53

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