Rich Kleiman

Jordan Wise

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

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.

Nigel Sylvester

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

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.

Sloane Stephens

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.