Simon Sinek

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The Confidence Conversation We Need to Have with Scott Galloway

A Bit of Optimism

My career is an accident. It started when I set out to rediscover my passion and reignite a spark I’d lost — and that journey led me to the work I do now.

If you know me from my books or my speaking, you know I’m fascinated by why people do what they do. What makes someone find joy and meaning in their life, or pursue something far greater than themselves?
I started A Bit of Optimism to explore those ideas and expand my own perspective. This podcast is a trove of honest conversations, with people who challenge me, teach me, or simply help me see things in a different way. Some guests are household names, and others you may be meeting for the first time. But each one of them has something to share that can help all of us grow.

So if you’re looking for a spark — some insight, inspiration, or just a reminder that good things are possible — join me on A Bit of Optimism! 

Let’s grow together.

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: <a target="_blank" rel="noopener noreferrer">https://www.simonandschuster.com/books/Notes-on-Being-a-Man</a>
Check out Scott’s podcast “The Prof G Pod”: <a href="https://www.youtube.com/c/TheProfGShow-ScottGalloway" target="_blank" rel="noopener noreferrer">https://www.youtube.com/c/TheProfGShow-ScottGalloway</a>
You can also watch his podcast “Pivot with Kara Swisher and Scott Galloway”: <a href="https://www.youtube.com/@pivot" target="_blank" rel="noopener noreferrer">https://www.youtube.com/@pivot</a>
To stay up to date with all of Scott’s work, head over to: <a href="https://www.profgalloway.com/" target="_blank" rel="noopener noreferrer">https://www.profgalloway.com/</a>
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