What makes an idea truly worthy of your time? Nir Zicherman, co-founder of Anchor and former Head of Audiobooks at Spotify, thought he’d left the startup world behind. But he kept wondering if he could help people learn in a better way. And oboe.com was born. In this conversation, Nir and Jason explore how to know when you’ve found something that’s more than a project. It’s your next calling. Learn more about your ad choices. Visit megaphone.fm/adchoices

When Jared Foster of Times Ticking bought a small watch shop, he realized one question was killing sales. So he replaced it with a simple, repeatable strategy that made customers feel welcome and ready to buy. That shift helped Times Ticking land on Entrepreneur’s list of America’s Favorite Mom & Pop Shops and turn quick repairs into big sales. This episode is brought to you by CLA. With you on every step of your financial journey. To learn more, visit CLAConnect.com. Learn more about your ad choices. Visit megaphone.fm/adchoices

 Executive coach Muriel Wilkins joins the show to unpack one of the biggest growth blockers in business. The leader who needs to be involved in everything. Drawing from her new book Leadership Unblocked, she breaks down how that urge forms, why it destroys trust and agency inside organizations, and how to recalibrate your time toward the work that actually drives results. Learn more about your ad choices. Visit megaphone.fm/adchoices

NBA stars don’t open up easily, but Taylor Rooks makes it look effortless. The lead host of Amazon’s NBA on Prime joins the show to share how she earns trust fast, even from the most guarded people in the room. It’s not just about asking questions. Whether you’re interviewing the team or leading it, trust is the foundation of every successful relationship. Learn more about your ad choices. Visit megaphone.fm/adchoices

Michael Bosstick, founder and CEO of Dear Media, breaks down the mechanics of audience growth and what smart creators do after they’ve built one. He shares his proven blueprint for turning attention into impact. This conversation will change how you think about the audience as an asset, not just a metric. Learn more about your ad choices. Visit megaphone.fm/adchoices

Most people think taking a month off work is impossible, but what if it’s actually a smart career move? Jillian Johnsrud, author of Retire Often, argues that planning a “mini-retirement” isn’t just good for your sanity. It forces you (and your company) to build better systems, and delegate more effectively. In this episode, Jason digs into her framework for making extended time off possible in any situation. Learn more about your ad choices. Visit megaphone.fm/adchoices

John Levy, behavioral scientist and author of Team Intelligence, is here to blow up what you thought you knew about leading teams. He reveals why most leadership advice is outdated, how the entire industry is built on a con man’s research from the 1900s, and what actually drives people to follow great leaders. He also shares one scientifically proven tip to build a smarter team. Learn more about your ad choices. Visit megaphone.fm/adchoices

Entrepreneurs face two kinds of problems: One has clear answers, the other does not. But is it possible to take unclear paths... and make them clearer? Alibaba.com president Kuo Zhang joins the show to talk about Accio, the company’s new AI tool that helps entrepreneurs create products, and the larger business lesson it represents. Learn more about your ad choices. Visit megaphone.fm/adchoices

Most businesses that resist change die. But Jake Shivery refused to give up analog photography and turned his Portland shop, Blue Moon Camera and Machine, into a thriving 26-person business.  But to keep his mission alive, Jake had to embrace changes he never wanted, from digitizing film to building a social media presence. In this episode, he shares how to balance stubborn focus with strategic flexibility and what every entrepreneur can learn about surviving disruption.    This episode is brought to you by CLA. With you on every step of your financial journey. To learn more, visit CLAConnect.com. Learn more about your ad choices. Visit megaphone.fm/adchoices

Branding expert Laura Ries joins Jason to talk about her new book, The Strategic Enemy , and the power of positioning. Together, they break down how companies can define what they stand against, win customers, and become the go-to name in their category. This is a packed conversation about how to create campaigns that resonate and understand the strategy behind the marketing that shapes our world. Learn more about your ad choices. Visit megaphone.fm/adchoices

What do you do when your company is running out of money, your industry has collapsed, and even you think your idea is dumb? That’s the situation Siqi Chen, now founder and CEO of the finance platform Runway, faced in 2016 when he became CEO of Sandbox, a VR startup. Yet through a bold move, Chen managed to get the right people to believe, securing funding for a product that was a stupid good time.  Learn more about your ad choices. Visit megaphone.fm/adchoices

Search is changing. Instead of typing a few words into Google, clients are now asking AI tools for hyper-specific recommendations. So how do you make sure they still find you? In this episode, Max DesMarais of Vital Designs shares how to position your business so large language models present you as the solution to your client's problem. Learn more about your ad choices. Visit megaphone.fm/adchoices

Marcus Lemonis built his reputation as the guy who could fix anything. It’s even in the name of his TV show The Fixer on FOX his new show following the success of The Profit on CNBC. But now, as he enters a new phase of leadership, he’s rethinking what it really means to lead. Lemonis has evolved. He’s leading from behind, pushing people harder than they’d push themselves, and even playing the villain if that’s what the business needs.  Learn more about your ad choices. Visit megaphone.fm/adchoices

 Michael Jacobson joined his uncle’s flower shop to help close it down.  Instead, he uncovered industry-wide problems like outdated tech, inefficient supply chains, and reliance on costly middlemen. By solving them one by one, he grew the French Florist into a thriving franchise that’s redefining the floral business. Learn more about your ad choices. Visit megaphone.fm/adchoices

The myth of the genius jerk founder has shaped startup culture for decades, but it’s wrong. Dr. Richard Hagberg and Tien Tzuo, co-authors of Founders Keepers, have the data to prove it. In this episode, they unpack the real traits that define high-performing founders, why bad behavior gets glorified, and how emotional intelligence and adaptability, not arrogance, drive lasting success. Learn more about your ad choices. Visit megaphone.fm/adchoices

Julia Hartz is the co-founder and CEO of Eventbrite, the platform built to help anyone host and sell tickets to an event. But after years in the business, Julia and her team realized something surprising. Their biggest growth opportunity wasn’t with the people creating events, it was with the people searching for them. On this episode, Julia shares how Eventbrite rethought its product, reimagined discovery, and why, in an AI-saturated world, real human connection might just be the ultimate value proposition. Learn more about your ad choices. Visit megaphone.fm/adchoices

 Ania Smith, CEO of TaskRabbit, has spent her career building marketplace businesses. She shares the operational challenges of matching people who need tasks done with people who can do them and how TaskRabbit solves for the millions of unpredictable human variables that come with it. Balancing supply and demand at scale means identifying the patterns and solving the problems. Learn more about your ad choices. Visit megaphone.fm/adchoices

Eynat Guez, co-founder and CEO of Papaya Global, shares how a single contract clause nearly bankrupted her first company and why confronting that worst-case scenario changed everything. Instead of panicking, she mapped out the fallout, turned it into leverage, and negotiated a way out. That mindset became a repeatable leadership strategy, helping her build a $3 billion global payroll platform while navigating both personal and professional risk. Learn more about your ad choices. Visit megaphone.fm/adchoices

How does an old video game get reborn as a modern entertainment behemoth? Just ask the producers behind Sonic the Hedgehog, Tomb Raider, and more. Their names are Dmitri M. Johnson and Mike Goldberg, co-founders of Story Kitchen, a media company that specializes in adapting classic video games and other unconventional IP for TV and film. Upcoming projects include adaptations for Toys R' Us, Teddy Ruxpin, Toe Jam & Earl, and more. On this episode, they share what makes a character worth reviving — and how to do it right. Learn more about your ad choices. Visit megaphone.fm/adchoices

Remember the Sonic “Two Guys” commercials? That simple marketing campaign transformed the brand — but creating it wasn’t simple at all. In this episode, Cliff Hudson (former Sonic CEO) and Craig Miller (former Sonic CIO) share how the “Two Guys” campaign emerged through testing, refinement, and real-time feedback. This  low-budget idea turned into a powerful brand asset. Hungry for more? Check out their book, Bricks and Clicks: How We Drove Sonic into the Digital Age. Learn more about your ad choices. Visit megaphone.fm/adchoices