FREEAgent

About FREEAgent

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.

Publisher

TRNSMISSIONradio

Category

business

Language

en

Explicit

No

First episode

17 Mar 2025

Latest episode

12 Oct 2026

Latest episodes

14 episodes in the feed.

1. 

   12 Oct 2026

   Jeff Staple

   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 bird Why the original Pigeon Dunk was never meant to "make sense" to Nike’s Oregon team The unexpected journalistic assignment that got him on Nike’s radar in the first place How he built a full-service agency mindset before ever calling it an agency Why he thinks "consultant" is the wrong word, and what he really wants to do for brands Jeff 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.

2. 

   14 Sept 2026

   Brenda Schamy

   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.

3. 

   8 Jun 2026

   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.

4. 

   23 May 2026

   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.

5. 

   10 Nov 2025

   TJ Adeshola

   TJ Adeshola recounts his career, from ESPN intern to private equity partner, and highlights cultural translation and community engagement in sports, in this interview.

6. 

   30 Sept 2025

   Beatrice Domond

   Beatrice Domond discusses how her family's support and her mother's resilience shaped her skateboarding career, leading to professional success and creative collaborations, in this interview.

7. 

   18 Aug 2025

   Nigel Sylvester

   BMX athlete Nigel Sylvester shares his journey of resilience and creativity, detailing his path from Jamaica, Queens to global brand deals in this interview.

8. 

   5 Aug 2025

   Darnell Strom

   Talent agent Darnell Strom explores the convergence of culture and commerce in the entertainment industry, highlighting the importance of representation and collaboration in building successful careers, in an interview with Kenny.

9. 

   17 Jul 2025

   Sloane Stephens

   Professional tennis player Sloane Stephens discusses her unique path to professional sports, her philanthropic work, and her approach to strategic brand investments in this interview.

10. 

    14 Jul 2025

    Rich Kleiman

    Rich Kleiman recounts his career shift from music to sports management, explaining his investment strategies with 35 Ventures and the development of the Boardroom media platform in this interview.

11. 

    7 Apr 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.

12. 

    31 Mar 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.

13. 

    24 Mar 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.

14. 

    17 Mar 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.

Who has been a guest on FREEAgent

Names identified in recent episode analyses. Showing up to five guests.

• TJ Adeshola
• Beatrice Domond
• Nigel Sylvester
• Darnell Strom
• Sloane Stephens

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

2 ratings

Spotify

5.0 / 5

8 ratings