Beatrice Domond

In this episode, we delve into the profound impact of family and upbringing on Beatrice Domond's illustrious career. Growing up in a supportive environment, Beatrice's journey into professional skateboarding was shaped by her family's encouragement and her mother's inspiring pursuit of dreams despite life's challenges. Discover how these early influences instilled resilience and creativity in Beatrice, propelling her to become a trailblazer in the world of skateboarding and beyond.We also highlight key moments in Beatrice's career, including her triumphant turn to professional status with Fucking Awesome, celebrated with city-wide recognition, and her creative collaborations with Vans, where she honors her heritage and family legacy. Additionally, Beatrice's groundbreaking signing with Supreme marked her as a pioneering figure in a male-dominated sport, further cementing her status as a cultural icon. These milestones underscore her unique blend of athletic prowess and artistic vision, making her a standout figure in the skateboarding community.

Jeff Staple breaks down the real blueprint behind building cultural impact that lasts for decades - from turning a pigeon into a global symbol to navigating Nike, corporate boardrooms, and a creative career that refuses to sit still. If you're a designer, founder, artist, or anyone trying to turn taste into leverage, this conversation is packed with the kind of hard-earned lessons most people never hear. Kenny sits down with Jeff in person for a wide-ranging conversation that traces the path from a sneakerhead teenager to founder of Staple and Reed Art Department and into a new era of consulting, advising, and helping brands move with real cultural intelligence. Jeff opens up about the 30-year evolution of Staple, the origin story of the Pigeon, and why a symbol everyone once dismissed became one of sneaker culture's most coveted grails. You'll discover:How Jeff landed on the Pigeon by seeing himself in the city’s most hated birdWhy the original Pigeon Dunk was never meant to "make sense" to Nike’s Oregon teamThe unexpected journalistic assignment that got him on Nike’s radar in the first placeHow he built a full-service agency mindset before ever calling it an agencyWhy he thinks "consultant" is the wrong word, and what he really wants to do for brandsJeff also shares the operating philosophy that has kept him relevant across fashion, footwear, sportswear, food and beverage, fintech, and even football. He explains why success is not just about creativity, but about understanding finance, strategy, sales, legal, and the machine behind the work - because the best ideas in the world still need a path to the world. We also get into his collaboration with FC St. Pauli in Hamburg, one of the most community-owned, anti-fascist, anti-racist clubs in football, and why that project felt like a perfect match for his own worldview around culture, identity, and belonging. This is a masterclass in creative longevity, strategic freedom, and knowing when to say yes - and when to protect your value. Perfect for anyone who wants more than inspiration and needs a real framework for building a career, a brand, or a voice that actually lasts. Jeff Staple is the founder of Staple, one of streetwear’s longest-running brands, and Reed Art Department, his creative agency focused on helping brands tell better stories. He’s known for the iconic Pigeon mark, his early work with Nike, and his ability to translate culture across fashion, sport, and business.

Brenda Schamy joins the Free Agent Podcast to share how she built a relationship-first legal practice across entertainment, sports, fashion, hospitality, and the wider creative world.From public defense to representing talent, brands, and entrepreneurs, Brenda breaks down what it takes to become a true part of a client’s team. The conversation explores trust, collaboration with agents and managers, navigating fast-moving industries like AI, protecting creative ideas, and the story behind her signature phrase: “CCing my lawyer, Brenda.”A candid conversation about ambition, service, building a meaningful career, and creating a version of balance that works on your own terms.

In a world where sports and entertainment collide, few trailblazers shine as brightly as Crystal, founder of Madwoman PR. With her unique approach to public relations, she has transformed the landscape of sports marketing, merging creativity with strategy to create unforgettable campaigns. Join us as we delve into her inspiring journey from Los Angeles to New York, and how she carved a niche for herself in the male-dominated world of sports.

Jordan Wise shares his journey from a successful career in trading to becoming a prominent football agent and the founder of Gaffer Magazine. He discusses the challenges and triumphs of navigating the football agency landscape, including the rigorous licensing exam and the importance of building relationships with young talent. Jordan also delves into the creation of Gaffer Magazine, a platform designed to showcase athletes' stories and personalities, and the innovative collaborations with brands that have emerged from it. Throughout the discussion, he emphasizes the significance of understanding both the sports and creative industries to effectively represent athletes and tell their stories. In this engaging conversation, Jordan Wise shares his experiences in the world of photography, particularly focusing on memorable shoots with iconic athletes and celebrities. He discusses the challenges and triumphs of capturing these moments, the passion behind launching a print magazine during a digital age, and the evolution of his creative agency. The dialogue also delves into the ambitious Komi 100 project, showcasing a diverse range of cultural figures, and concludes with insights on embracing chaos and executing ideas with conviction.

TJ Adeshola explores the journey from his early days as an intern at ESPN to becoming an operating partner at a private equity firm. They discuss the importance of internships, building relationships, and adapting to the changing landscape of sports and digital media. TJ shares insights on navigating corporate culture, overcoming imposter syndrome, and leveraging his unique experiences to thrive in the tech industry. In this conversation, TJ shares his journey from working at ESPN to building a sports vertical at Twitter, emphasising the importance of cultural translation and community engagement in sports. He discusses his experiences navigating the corporate landscape, the significance of representation, and the challenges of transitioning out of Twitter during a tumultuous time. TJ highlights the value of being a cultural translator in the sports industry and his current role in private equity, focusing on ownership and investment in sports franchises.

Step into the world of Nigel Sylvester, a BMX athlete whose story is a testament to resilience and creativity. Growing up in Jamaica, Queens, Nigel faced the unique challenge of pursuing a career in a sport without clear pathways or role models. In this episode, he shares candid insights into the struggles and triumphs that marked his journey, from crafting "sponsor me" tapes as a teenager to landing groundbreaking deals with brands like Nike and Gatorade. Nigel reflects on the pivotal role of family, the influence of his community, and the moments of self-doubt that tested his resolve. With a focus on storytelling and cultural impact, Nigel's journey is a powerful reminder of what can be achieved with passion and perseverance. Whether you're a BMX enthusiast or simply love a compelling personal story, this episode offers a deep dive into the heart and soul of a true innovator.

Darnell Strom shares his journey from politics to the entertainment industry, detailing his role at UTA and the unique intersection of culture and commerce. He discusses his extensive client list, the importance of representation, and how his background in politics informs his work in entertainment. Darnell emphasizes the blending of different worlds and the value of collaboration in building successful careers for his clients. In this conversation, Darnell Strom and Kenny discuss the importance of building relationships in various industries, particularly in sports and culture. They reflect on their personal connections, the impact of influential figures like Virgil Abloh, and the recent acquisition of ID Magazine by Carly Kloss. The dialogue emphasizes the convergence of culture and sports, the innovative roles within sports management, and the significance of mentorship and legacy in creative fields.

In this engaging conversation, Sloane Stephens shares her journey from a late starter in tennis to becoming a professional athlete and a successful entrepreneur. She discusses her foundation aimed at introducing tennis to underprivileged kids, her experiences in the media, and her passion for investing in brands that resonate with her values. Sloane reflects on her career highlights, the challenges of being a professional athlete, and her commitment to wellness and self-care through her brand, Doc & Glo.

In this engaging conversation, Rich Kleinman shares his journey from the music industry to sports management, detailing his investment strategies through 35 Ventures and the creation of the Boardroom media platform. He discusses the importance of building relationships, the challenges of transitioning industries, and the vision behind his ventures, including the recent investment in PSG. Rich emphasises the significance of community and the role of print media in a digital age, providing insights into the evolving landscape of athlete representation and entrepreneurship.