The Courageous Podcast with Ryan Berman

Jackie Plaza knows a thing or two about betting on yourself. She left a successful career in Los Angeles for a new opportunity in San Diego, stepped into the challenge of helping reshape perceptions of one of the world’s most recognizable theme parks, and discovered that taking risks gets a little easier once you’ve survived a few that didn’t work out. Today, as VP Marketingand Sales at SeaWorldSan Diego, Jackie is bringing that same willingness to experiment to a brand with more than 60 years of history. In their conversation, Ryan and Jackie talk about the freedom that comes from getting comfortable with failure, why the best leaders know when to call an audible, and what happened when a seemingly crazy idea for a hip-hop and R&B concert series became a massive hit. Jackie also shares the side of SeaWorld she didn’t fully understand until she joined the company, including its decades of animal rescue work and the experience of releasing rehabilitated animals back into the wild.

Ania Smith learned early that you can’t control everything that happens to you, but you can be intentional about what you do next. After moving from Poland to South Dakota at 12 without speaking English, she developed a curiosity and adaptability that would eventually take her to companies including Airbnb, Uber Eats, Walmart, and now Taskrabbit, where she serves as CEO. In this conversation with Ryan, Ania talks about the difference between reacting to change and choosing it for yourself, and why asking better questions has given her the confidence to keep making big moves. She also opens up about taking her family on a gap year in Argentina and the surprisingly simple framework she and her husband use to balance two ambitious careers with raising three kids. Plus, Ania shares what she’s learned from more than a decade building marketplaces, how AI could transform the way we hire people to help in our homes, and why staying close to Taskers remains deeply personal to her.

Everyone wants change to be easier. Ryan Berman thinks that's exactly the wrong goal. In this solo episode, Ryan challenges the growing belief that transformation should be effortless and makes the case that the strongest teams don't avoid friction—they create the right kind of it. Ryan explains why hard conversations are the real starting point of change, why leaders should stop trying to eliminate discomfort, and how alignment, belief, and clarity create the foundation for lasting transformation. He also shares the question every team should be asking, why "believe again" became one of Courageous' earliest rallying cries, and the mindset shift that can help leaders stop waiting for change and start creating it.

Elle McCarthy is drawn to transformation. It's the thread that connects everything she does, from challenging outdated ways of thinking to helping some of the world's biggest brands—including Ford, PayPal, EA, and now McAfee—reinvent themselves from the inside out. In this conversation with Ryan, Elle shares why real change starts by getting people to believe in what's possible, why the strongest brands are built long before a campaign ever launches, and how a little "chaos magic" has helped shape her approach to leadership. They also discuss building trust during times of change, the lessons motherhood has taught her about leading others, and the personal promise she's made to stay true to the values that first drew her into marketing.

Adam Markel has built his career around helping people navigate change, but lately he's been asking a bigger question: what if the real challenge isn't changing ourselves, but changing the systems we work in every day? After years advising Fortune 500 companies and studying resilience, Adam has become convinced that culture isn't a byproduct of leadership—it's the reason organizations succeed or struggle in the first place. In this conversation with Ryan, he unpacks why leaders can no longer expect employees to shoulder the burden of resilience alone, and what it looks like to build a culture that people actually want to be part of. They also dig into why so many well-intentioned leaders still get culture wrong and the simple idea that sits at the heart of Adam's new book, Re-Culture.

Helen Calcraft believes the best creative work can't exist without joy. At a time when fear, AI, and constant change are reshaping the advertising industry, the co-founder of Lucky Generals joins Ryan for a thoughtful conversation about what leaders can do to protect creativity instead of stifling it. Together, they explore why saying no is sometimes the most important decision a business can make, how trust became the foundation of Helen's decades-long creative partnership, and what she learned from building not one but two successful agencies. They also discuss the challenge of letting go of day to day control, the surprising lessons Helen is taking from executive coaching, and why designing the next chapter of your life requires every bit as much intention as building a great brand.

DJ DiDonna has spent years studying what happens when people have the courage to step away from work, and his new book, Big Time Off, makes the case that the biggest breakthroughs rarely happen while we're glued to our calendars. A senior lecturer at Harvard Business School and founder of The Sabbatical Project, DJ joins Ryan to challenge one of our most deeply held beliefs: that the path to success is always to keep pushing forward. Together, they explore why so many people wait for burnout, layoffs, or life-changing events before giving themselves permission to pause, and why creating space intentionally can lead to greater clarity, stronger leadership, and a more meaningful life. Ryan and DJ also discuss identity, ambition, the pressure to always be productive, and the surprising lessons that came from DJ's own 900-mile pilgrimage across Japan.

Mike McCabe has spent the last two decades helping shape the world of competitive gaming, but what excites him most is what comes next. In this conversation with Ryan, the Esports Foundation CEO shares his vision for esports as a truly global sport while reflecting on the realities of building something at a scale few people can imagine. From helping bring together the world's biggest games, players, and clubs to navigating the last-minute decision to move the Esports World Cup from Riyadh to Paris just weeks before competition, Mike offers a candid look at leadership under pressure. They also explore fandom, innovation, resilience, and the opportunities esports is creating for a new generation of competitors around the world. Their conversation comes just ahead of the Esports World Cup Paris 2026, which begins July 6 and runs through August 23. Follow the action at https://esportsworldcup.com/en

Melissa Ninegar has built a career helping people navigate some of life's biggest moments, but her most valuable leadership lessons didn't come from a handbook or HR playbook. In this conversation with Ryan, the Senior Director of People & Culture at Once Upon a Farm shares the hard-earned truths that have shaped how she leads, from believing you belong in every room you enter to choosing how life's toughest moments define you. Ryan and Melissa explore imposter syndrome, resilience, grief, growth, and why some of the most important leadership skills are rarely taught. They also discuss the power of showing up authentically, finding magic in the messy moments, and why the real opportunity in leadership begins when we stop seeing people as resources and start seeing them as humans.

After 15 years helping shape the storytelling behind Disney’s most iconic experiences, former Vice President of Global Creative Jim Real joins The Courageous Podcast to talk about what it means to leave a dream job in pursuit of what’s next. Drawing on a career that spans Disney, global agencies, and years spent building brands across the U.S. and Asia, Jim shares why courage is less about fearlessness and more about moving forward before the path is fully clear. Ryan and Jim explore the power of storytelling and the importance of curiosity. Jim also reflects on lessons from his father’s journey to sobriety, and why the next chapter of his career is focused on helping leaders, brands, and teams find the stories only they can tell.