FREEAgent

TRNSMISSIONradio

5.0 (2)
Business
Updated Weekly

Hosted by Kenny Annan-Jonathan, founder of sports marketing agency The Mailroom. FREEAgent is a series of conversations with some of the worlds greatest visionaries in Sports, Culture and Business.

Jun 8

Crystal Frost

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.

1h 13m
May 23

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.

1h 20m
11/10/2025

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.

1h 18m
08/18/2025

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.

1h 11m
08/05/2025

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.

1h 9m
07/17/2025

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.

1h 4m
07/14/2025

Rich Kleiman

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.

43 min
04/07/2025

Alex Wilde

Alex Wilde shares his journey from working in PR to founding his own sports marketing agency Status. He discusses his early career at Beats by Dre, the cultural impact of the brand, and key moments that shaped his career, including the London 2012 Olympics. Alex reflects on the importance of building authentic relationships in marketing and the challenges he faced transitioning to EA Sports. He emphasizes the significance of being indispensable in the industry and the value of identifying talent early on.

1h 11m
03/31/2025

David Bellion

David Bellion relives his unique journey from being a professional football player to becoming a creative director at Red Star Football Club. He discusses the importance of curiosity, creativity, and the supportive role of his chairman in supporting and shaping his vision from player to Creative Director of the same club he played for. David emphasizes the significance of pursuing one's passions and the unconventional path he took in transitioning from sports to the creative industry.

59 min
03/24/2025

Stuart Duguid

Stuart Duguid shares his journey in sports management, highlighting his experiences with top athletes like Naomi Osaka, Nick Kyrgios and Aryna Sabalenka. He discusses the importance of authenticity in athlete branding, the challenges of transitioning from a large agency to starting his own company Evolve, and the innovative strategies he employs to navigate the evolving landscape of sports marketing and media production.

59 min
03/17/2025

Daniel Yaw Miller

Daniel unpacks his multifaceted journey from a corporate lawyer to a prominent journalist in the sports and fashion industry that landed him a position at The Business Of Fashion, one of the world’s leading fashion media outlets. He discusses his unique experiences, including living in Japan, his pivotal career shifts, and the intersection of sports and fashion. Dan emphasises the importance of honesty in journalism and the relationships he has built with industry leaders, while also reflecting on the challenges of navigating these connections whilst keeping a fair approach to his documentation.

56 min

11 Episodes

5

out of 5

2 Ratings

Insightful

03/24/2025

confidential notice

This show is very insightful and gives me a window seat into the lives of those at the intersection of sports and marketing.

Hosted by Kenny Annan-Jonathan, founder of sports marketing agency The Mailroom. FREEAgent is a series of conversations with some of the worlds greatest visionaries in Sports, Culture and Business.

Creator

TRNSMISSIONradio
Years Active

2025 - 2026
Episodes

11
Rating

Explicit
Copyright

© TRNSMISSIONradio
Show Website

FREEAgent