Bob Philion spent 20 years wearing the cat on his chest—first as employee #1 launching Puma Golf, then as the architect behind Cobra Puma Golf, and ultimately as the leader of Puma North America. In this conversation with Ryan, Bob retraces three distinct “chapters”: moving from Europe back to Boston to start a category from scratch, building Cobra Puma Golf into a global disruptor out of Carlsbad, and then steering Puma’s North American engine across basketball, running, soccer, Formula One, and beyond. He shares what courage looked like inside the brand—betting on golf, doubling down with Cobra, and re-entering basketball. Now on sabbatical and writing a book, Bob distills three decades in sports into lessons on growth, mentorship, and vision—because, as he puts it, “growth is fun, growth is good, and it’s always worth chasing.”

Courage Brands Win. This week, we hit pause on the usual interview format for a fast, fun “Courage Brands Spotlight” discussion featuring Ryan and his partners Nicole Miller and Billy Collins. Nicole kicks things off with The Female Quotient—an unapologetic, action-oriented force that meets leaders where they already gather (CES, Cannes) with Equality Lounges and hard conversations everyone’s invited to join. Billy spotlights the Savannah Bananas, who are on a mission to rewire baseball for sheer fun; two-hour games, innings ending when someone scores, and fans recording an out by catching a foul ball. Ryan closes with BeatBox Beverages—the party-ready, wine-based cocktail that started on Shark Tank and is now riding a wave of success with Shaq.

Knight Campbell turns mountains into meeting rooms. A former Navy helicopter pilot and Naval Academy leadership instructor, he now takes executive teams off-grid—rock climbing, rafting, and trekking—to work on the real “crux” of how they lead. Phones go away. Titles fade. Trust and honest talk show up. In his conversation with Ryan, Knight recalls a Joshua Tree client who lost service and then chose to keep her phone off until Monday, proving that awe and accountability open conversations no boardroom can. He shares a core lesson from the alpine: sometimes speed is safety, but great leaders fight the real enemy—hurry—by practicing presence.

Bree Groff thinks it’s an emergency that half of us feel dread at work every week, and that we’re trading five‑sevenths of our lives just to reach Friday. In this conversation with Ryan, the former NOBL CEO and current SYPartners advisor traces how losing her mom to cancer and caring for a dad with Alzheimer’s jolted her from helping leaders execute their vision to stating her own. She introduces a few characters and themes from her latest book, Today Was Fun, including Bob the Alien, who decides Google Calendar secretly runs Earth. Bree’s metric is simple: curl into bed most nights and honestly say, today was fun. If not, rewrite the rules—you made them up anyway.

Bart Berkey believes in doing what most people don’t—remembering names, anticipating needs, and showing up with contagious positivity. A former global exec in luxury hospitality (Ritz-Carlton, Hyatt), Bart took three decades of service experience and turned it into a movement. In this episode, Ryan and Bart talk about the power of “active remembering,” why being kind beats being right, and how the phrase Most People Don’t. But You Do. became a calling card for courageous leadership. Bart shares lessons from the stage, his podcast, and the frontlines of hospitality, offering practical ways to notice more, include others, and overdeliver. His belief? The smallest gestures often have the biggest impact—and our job as leaders is to help others feel seen.

Todd Kaplan believes legacy brands should feel as fresh as a track that just dropped. In his first ten months as CMO of Kraft Heinz North America, the former Pepsi disruptor has already launched DJ Mustard’s limited-edition condiment, staged the Oscar Mayer “Wienie 500,” and watched each sell out or go viral in minutes. In this episode of The Courageous Podcast, Todd tells Ryan how his “collaborativity” sessions collapse client-agency walls so ideas can sprint from a cafeteria napkin to Grammy broadcast almost overnight. He explains why marketers must “play to win,” and how short steps plus a long vision keep 70 household staples evolving without losing their soul. From Nike’s Kool-Aid sneakers to reviving 150-year-old pantry icons, Todd shows that speed, fun, and strategic risk are now table stakes for brands.

Alexi Lalas. Naomi Girma. Tim Howard. Landon Donovan. Richard Motzkin has been there representing each of them throughout their careers as their Sports Agent. In this conversation with Ryan, Rich recalls his journey of quitting big-firm law to become U.S. Soccer’s first in-house counsel, and how that leap led to his own agency which began before Major League Soccer even had a name. He explains how the early days of MLS felt like a startup, complete with fax machines and jersey swaps that exposed just how far U.S. soccer still had to go. Now a top executive at Wasserman, Richard reflects on what’s changed, what still holds the sport back, and why chasing happiness, not just trophies, remains his north star.

Dr. Jonah Essers fights insurance red tape with the same rigor he once brought to genetic research at Columbia and Harvard. In this conversation with Ryan, he explains how his blunt LinkedIn posts—naming pharmacy-benefit managers and citing peer-reviewed data—have forced billion-dollar payers to reverse drug denials within hours, delivering treatments that 45-day appeals would delay. He recalls the day a hospital CMO tried to silence him but, after hearing the evidence, granted full support. Ryan and Dr. Essers also unpack Walter Cronkite’s jab at America’s “healthy, caring system,” debate fairness versus justice, and explore the quiet fear doctors feel when advocacy risks their jobs.

Dr. Christopher Bader has spent a decade mapping the nation’s anxieties through the Chapman Survey of American Fears, and the picture he paints is as revealing as it is sobering. In this episode of the Courageous Podcast, Dr. Bader explains why “corrupt government officials” has topped the list since 2014, how media algorithms amplify our sense of danger, and why withdrawing from public life only makes neighborhoods less safe. He shares the survey’s most startling insight - that most Americans worry about threats they can’t control while underestimating the risks closest to home. Dr. Bader also previews the eleventh wave of the study and traces his own path from Seattle kid to Chapman professor.

Kass and Mike Lazerow run companies the way great doubles teams win tennis matches: Kass owns the baseline of operations while Mike roams the net hunting openings -- neither drifts into the other’s court. In their conversation with Ryan, they unpack their new baby of a book; Shoveling $h!t, what they describe as an entrepreneurial love story and deeply personal playbook that distills eight ventures and nearly $10 billion in exits into fifty straight-talk lessons any founder can lift. Kass shows how fixed Wednesday date nights and clearly drawn responsibilities turn raw startup chaos into durable culture. Mike retraces the pattern-recognition that carried him from a college newswire to Buddy Media and an early Liquid Death stake. Their closing charge is simple: protect your partnership, share the upside, reinvest in the world - and never be afraid to pick up a shovel when the next idea calls.