Episode 257: Orlando von Einsiedel - The Cycle of Love
Tue Feb 03 2026
Oscar-winner, snowboarder, and one of the most influential documentary filmmakers working today, Orlando von Einsiedel makes his return to the show, nearly eight years after his first appearance.
In that time, films such as Virunga, The White Helmets and The Lost Children have set a new standard in gripping, immersive documentary story-telling.
Recorded live at the 2025 Kendal Mountain Festival in front of a sold out audience, this wide-ranging conversation centres on Orlando’s latest film The Cycle of Love, which is currently cleaning up on the festival circuit.
It also a rare, honest insight into the reality of life at the sharp end of documentary filmmaking, even when you appear to have achieved the success everybody craves.
We dig into Orlando’s creative process, the state of the documentary landscape, and the somewhat dire financial realities of getting ambitious projects off the ground, even for an artist of Orlando’s calibre.
If you enjoyed my recent episode with Lucy Walker, or are interested in the real, often precarious mechanics of a creative career, this one’s for you.
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To find out more about what I do, you can sign up as a subscriber to my Substack newsletter here. There's a brilliant community and much more than just the podcasts.
This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.wearelookingsideways.com/subscribe
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Oscar-winner, snowboarder, and one of the most influential documentary filmmakers working today, Orlando von Einsiedel makes his return to the show, nearly eight years after his first appearance. In that time, films such as Virunga, The White Helmets and The Lost Children have set a new standard in gripping, immersive documentary story-telling. Recorded live at the 2025 Kendal Mountain Festival in front of a sold out audience, this wide-ranging conversation centres on Orlando’s latest film The Cycle of Love, which is currently cleaning up on the festival circuit. It also a rare, honest insight into the reality of life at the sharp end of documentary filmmaking, even when you appear to have achieved the success everybody craves. We dig into Orlando’s creative process, the state of the documentary landscape, and the somewhat dire financial realities of getting ambitious projects off the ground, even for an artist of Orlando’s calibre. If you enjoyed my recent episode with Lucy Walker, or are interested in the real, often precarious mechanics of a creative career, this one’s for you. -- This week’s codes to use for some big old savings: LOOKINGSIDEWAYS for HUGE savings on ski and snowboard hire with Intersport this winter. LOOKINGSIDEWAYS10 for 10% off any order from Finisterre LOOKINGSIDEWAYSXDB for 15% off anything from Db LOOKINGSIDEWAYS2025 for 15% off any Albion purchase LOOKINGSIDEWAYS for a whopping 20% off anything from Goodrays. LOOKINGSIDEWAYS for 15% off any Stance order -- To find out more about what I do, you can sign up as a subscriber to my Substack newsletter here. There's a brilliant community and much more than just the podcasts. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.wearelookingsideways.com/subscribe