You’re envious of someone. Why? Pick the reason. They make more money than you. Accomplish more than you. Their career is bigger. Their title is cooler. You already know that comparison is the thief of joy. Jason doesn't need to tell you that — and anyway, knowing it doesn’t help. So today, Jason will give you something that actually helps: he will show you how the people you envy aren’t as enviable as you think — and how you can celebrate what you have.

If someone says the wrong thing, is it actually helpful to tell them? Today's caller, Jeff, got a message from an acquaintance asking if Jeff could secure an internship for his son. Jeff told his acquaintance that it would have been better if the son had reached out directly... should he have said that? Today, Jason and Nicole help you find the line that separates helpful feedback from overkill.

Today, Jason teaches you how to chill out… while getting everything important done. Because for all the wild stories out there about hustlers hustling, there’s something important you need to know. Jason explains.

Rebecca Minkoff has built brands, led teams, negotiated deals, and navigated high-stakes conversations for decades — so it’s no surprise she’s become an expert communicator along the way. Today, Rebecca joins Nicole to share the exact scripts she uses for moments most people dread: firing someone, giving tough feedback, asking for a refund, setting boundaries, and more.

In a Mother's Day rerun, Jason checks in with Nicole to see how she's managing the demands of work and parenting a four-month-old. Nicole opens up about the mental load of being the parent responsible for most of the childcare logistics. Jason then phones a friend—his wife, Jen—who shares the systems she and Jason have put in place to create a more balanced and equitable approach to parenting.

When the pressure’s on, it’s easy to believe that everything hinges on this one moment. But what if the stakes aren’t as high as you think? In this episode, Jason shares a personal story about how reframing the situation can reduce stress, improve your decision-making, and lead to better results.

A throwback episode! When a video of a plane passenger refusing to give up her seat for a toddler went viral, the internet had thoughts—and most of them weren’t kind. Today, Jason and Nicole sit down to unpack why they're siding with the passenger, and what this viral moment reveals about how we rush to judgment online. This episode isn’t just about plane etiquette—it’s about the stories we tell, the facts we skip, and the cost of outrage culture. By the end of the episode, you’ll walk away with a sharper lens for spotting bias in viral narratives—and how that same skill can help you make better, smarter decisions in business and in life. ⁠HERE⁠ is the story referenced in the episode.

Jenny Stojkovic is a venture capitalist and a top LinkedIn creator thinking critically about AI, the future of social media, and the mistakes creators can make as they scale. And as you’re about to hear, that is actually how Nicole and Jenny met. Today, they share that story, and the essential lessons anyone building on social media today needs to know. From the conversation, check out: The creator rights and IP resource Jenny coauthored with Rebecca Rechtszaid Shira Lazar and What’s Trending Sim Kaur and Friends That Invest The Women Creators Tyler Chou, The Creators’ Attorney Jenny Stojkovic linkedin.com/in/jenniferstojkovic instagram.com/jennystojkovic tiktok.com/@jennystojkovic youtube.com/jenny.stojkovic Join 50K subscribers for Jenny’s weekly newsletter:⁠ play.jennystojkovic.com⁠

What happens when you are getting less out of a situation than you would like? It can be hard to know if the little you are getting is worth it or not. Jason has developed a useful framework for how to make that decision. And it all starts with thinking about a bag of chips….

Have you ever felt misunderstood by a manager? If so, you know how frustrating—and downright demoralizing—it can be. Today’s caller, Mike, is stuck in that very situation. His manager constantly second-guesses his work, and Mike is desperate to find a way to get on the same page. To tackle this challenge, Jason is joined by Jenny Wood, former Google executive and author, to break it all down. Together, they equip Mike with a clear, actionable framework to transform his next conversation with his manager—turning tension into trust and frustration into forward momentum. Buy Jenny's book Wild Courage ⁠here⁠!