In this episode, we sit down with Sam Applebee, festival organiser, social entrepreneur, and technologist, whose journey brings together AI consulting, social innovation, and community-led creativity. Sam shares how early experiments with self-organising systems in a London AI startup shaped his views on leadership and collaboration, and how those lessons now inform his work on Beginnings, a volunteer-led music and arts festival in Portugal.

We explore what it takes to build trust-based organisations, why radical transparency can both empower and overwhelm, and how scaling inevitably reshapes the dynamics of collaboration. Sam reflects on “cooking slow and not growing too fast” when it comes to building meaningful communities.

The conversation ranges from self-set salaries and peer-reviewed systems to the joy and tension of organising festivals without on-site money. We discuss the deeper questions: How do organisations thrive when AI accelerates automation? What role can creativity and community play in helping us navigate a future where meaning and purpose need new anchors?

Talking Points:

• Early experiments with self-managing systems and the challenges of scaling.

• The creation and evolution of Beginnings, a 500-person community festival.

• Why processes can both support and stifle collaboration.

• Lessons on slowing down, staying small, and prioritising relationships.

• How AI could reshape purpose, productivity, and creativity in organisations.

Tune in for a thought-provoking exploration of how communities and organisations can design themselves for meaning, creativity, and resilience in a rapidly changing world.

Do you want to bring these practices into your organisation? Reach out at [email protected] or visit us at kholo.co to start the conversation.