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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This week’s codes to use for some big old savings: 

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If you ask me, this week’s guest Axel Pauporte is one of the most influential snowboarders of the 1990s and 2000s.

Even if you don’t know his name, you’re living in a snowboarding culture that he helped shape. Especially if you’re a European snowboarder. 

To qualify this rather bold claim, it helps to remember how singular an outlier Axel truly was. 

Back in the early 90s, professional snowboarders from mainland Europe were a genuine rarity. Professional snowboarders from flat Northern European countries such as the Netherlands, the UK or Belgium, where Axel was brought up? Legitimate trailblazing pioneers.

All of which makes Axel’s career path especially legendary. Here was a rider who started snowboarding late - and on dry slope to boot.

And who, by the end of a storied twenty-year career, was universally regarded as one of snowboarding’s greatest ever freeriders, and had demonstrated that European riders could lead the way in a proving ground like Alaska alongside peers such as Travis Rice, Jonaven Moore and Jeremy Jones. 

And the story of how Axel made this happen is as unlikely as it is instructive. This isn’t your standard pro snowboarder origin story. 

Here we have an outsider, both literally and figuratively, who was driven by a potent emotional combination: his own insecurities, a Stakhanovite work ethic, and a ferocious desire to use snowboarding a way of finding a sense of belonging. 

In Axel’s case, that ultimately led him to AK, and the pursuit of risks that today make him pause and wonder, as we discussed. 

As you might be gathering, this is a very honest conversation that covers belonging, identity, and the psychology and selfishness of risk; as well as the reckoning that comes to us all once the body and mind begins to fade, and other priorities take precedence.

Big thanks to Axel and my friend Dave Mailman for the help with this one. 

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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 

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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.

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It’s December 24th. Which must means it’s time for my much-loved Festive Special with close friends-of-the-show Tim Warwood and Adam Gendle!

This might well be the conversation I look forward to the most each year. If you’re new to the show, some background: I go back thirty years with these boys, who I first met through the very close British snowboarding community we’re so lucky to be an integral part of.

Eight years ago, we got together at Christmas to record the first Looking Sideways special, and it’s since become a tradition during which we get together to catch up, and generally glory in the closeness that comes when you’ve been friends for as long as the three of us have.

And this is a lesson I’ve especially learned this year: that as you get older, the fundamental element of trust that exists between you and your oldest pals provides a level of increasingly-needed comfort.

It’s one of the best parts of getting old. Especially as it’s so difficult to see the people you love. So as the years pass, this episode becomes ever more important and cathartic to me.

As ever, it’s a freewheeling catch up that saw us cover our usual topics - our annual Yuletide review, our highlights of 2025, our hopes for 2026, and the now traditional quiz of the year (spoiler alert: I won!).

As ever, wherever you’re listening to this, grab a festive drink and a mince pie, don the Santa hat, and join us as we wax festive for a couple of hours.

I’ve been fortunate enough to enjoy another brilliant Looking Sideways year, so huge thanks for listening and supporting what I do. I’ll be back refreshed, rested and ready to go once again in 2026 - in the meantime, have a brilliant break 🎄

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Some links to use below - merry Christmas!

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

--

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Adam Skolnick is a journalist, none-fiction writer, famed Roll On podcaster, and the author behind the brilliant new novel - his first! - American Tiger.

American Tiger (a work that has been gestating for years) is a milestone for Adam in more ways than one.

As his first published novel it is, of course, the latest stage in his evolution as an artist.

But it is also confirmation of the way that personal philosophies inevitably seep into the work we produce. 

Because while the book is ostensibly about a young girl called Bell spotting a tiger in suburban California, it’s really about much more.

Like all the best works of art, American Tiger brings together the preoccupations that have underpinned Adam’s career up to now into one artistically coherent and page-turning whole. 

It’s an LA novel, a coming-of-age novel, and a novel about the way that Adam sees nature as a partner, not a resource.

And the story of how Skolnick brought this thing into the world is itself an instructive tale for anybody attempting to get their own creative vision off the ground: part creative psychology, part survival guide to the modern writer’s life, part sheer bloody-minded entrepreneurialism in an era of shrinking outlets and collapsing budgets.

I loved this conversation, and I think you will too. Find it via my website, the link in bio, or the usual platform.

My thanks to Adam for the brilliant chat, and to April for all the help. Looking forward to meeting you both in person soon! 

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

In this latest follow-up episode to The Announcement, I’m joined by activist, entrepreneur, engineer, and policy researcher Len Necefer for a conversation in which we discuss the tension between ideological purity and pragmatic action when it comes to genuine environmental and social change.

Len, a proud member of the Navajo Nation, works at the intersection of Indigenous peoples, natural resource, and environmental policy. 

He is the founder of Natives Outdoors, a board member at the Honnold Foundation, and somebody whose work has become essential when it comes to the current debate around how to create meaningful impact in an imperfect system.  

This, of course, was a key theme of my Announcement series proper. And it is the territory Len provocatively and articulately explores through his work and writings, in which he respectfully yet firmly challenges the comfortable assumptions around ‘purpose’ that tend to dominate the discourse in outdoor and adventure spaces.

As you’ll be aware if you’ve read Len’s brilliant Substack or follow him on social media, he is not interested in letting individuals, brands, or organisations mark their own homework. 

Instead, he is interested in asking the only questions that truly matter: Will this have an impact? Is your work upsetting the right people? Is it calculated to drive forward the change you claim to seek? 

The more I explore these avenues, the more I think these are really the only honest questions worth asking, which is why I admire Len’s work and his willingness to ask these questions so outspokenly and articulately. 

From this challenging conversation, you'll gain insights into:

- Why accountability matters more than stated intentions in purpose-driven business

- How Indigenous perspectives fundamentally shift conversations around environmental policy and outdoor access

- What it means to take genuinely bold approaches, rather than performative stands

- Why challenging industry orthodoxy is essential to meaningful progress

This was the type of challenging and progressive conversation that Len specialises in— full of provocations, unimpeachable logic, and the moral integrity we sorely need at this time. 

For bonus and behind-the-scenes material, click here.

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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Filmmaker, surfer, seeker and - OK, then - influencer: Seth Hughes is one of British surfing’s most thought-provoking creative presences.

We’ve been friends for a few years now, and like everybody who follows him on Instagram, over the last few years I’ve been following his ‘apprenticeship to the land and sea’ with fascination and interest.

I’ve also appreciated the increasingly searching and occasionally uncomfortable questions he likes to pose.

How to regain a new understanding of health and wellness. How to regain our lost relationship to nature. How we escape the pernicious power of addictive technology. And how to reconcile our ‘real’ and public-facing selves, and the many masks we wear.

These are Seth’s preoccupations and themes. And they were among the many topics we discussed in this meandering, insightful and hugely enjoyable exchange, recorded during my visit to Cornwall at the end of October 2025.

We began this conversation on the site of the old mining slag heap that forms a backdrop to our mutual pal Chris Hines’ beautiful property, before heading inside to record this evocative conversation.

I’m very grateful to Seth and Chris for the lovely afternoon. I learned a lot from our conversation, not least about my own views and behaviours.Hope you enjoy it as much as I did. 

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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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Skateboarder, photographer, artist, Toy Machine company owner - Ed Templeton is one of skateboarding’s most influential and beloved influences. 

And as a 14-year-old who obsessively wore out their copy of 1281 back in the day, he was a real and important influence on me personally when it came to working out how to express myself as a creative person. 

What, you could be into this stuff - and also art, culture, and literature? And skateboarding and snowboarding could be the catalystt for this exploration? This was revelatory to me.  

All of which is why I’ve been hoping to interview Ed since I began Looking Sideways back in 2017. In October 2025, we finally made it happen.

Whenever you interview somebody of such notoriety, who at this point has been interviewed countless times, the challenge is always the same: how can I make this person comfortable, and get them to open up?

As is often the case on Looking Sideways, a shared interest in art and creativity was the foundation of a conversation rich in insight and honesty.

Yes, we spoke about skateboarding, Toy Machine, Welcome to Hell, art and photography, as you might expect.

But we did so through an unexpectedly wistful and nostalgic lens as Ed, now in his 50s; and with the wit, candour and humility that have always been his hallmarks; grapples with the topics that come for us all in the end: aging, impermanence, the value of possessions, the influence of our forebears, and the legacy we want to leave behind.

Special thanks to Don Brown and Thomas Campbell for their help with this one.

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Legendary surf and skate film-maker Thomas Campbell’s new film Yi-Wo has been ten years in the making.

So when TC got in touch to ask if he could come back on the podcast to talk me through the decade-long creative process that went into the making of this instant classic, I was in. I’ve had the good fortune to see Yi-Wo a few times now, and can confirm that this long-awaited release is a wondrous, challenging and completely artistically uncompromising piece of work that confirms TC’s position as surfing’s premiere bloody-minded auteur.

And personally, I appreciate that. As we discussed during our conversation, in times of social and political turmoil such as these, the role of art becomes ever more important. Especially a work like Yi-Wo, which rejects immediacy, defies easy characterisation, and asks many necessary questions of the audience.

If you’ve listened to my first two chats with Thomas, during which we delved into his creative process in great detail, you’ll appreciate this conversation as a complement to those previous exchanges.

Here is the culmination of ten years of ‘sitting in the chair’, as he likes to say, an active demonstration of where TC’s curiosity, principles and artistic integrity have led him; and a brilliant summation of the fact that, in the end, creativity is about making decisions, putting one foot in front of the other, and seeing where it leads you and your audience.

As ever, it was a great privilege to get such a priceless insight into this unique artist’s creative process, and to catch up with one of surfing’s great original voices.

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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

In this fourth follow-up episode of The Announcement, which was recorded live at MAD Fest in early July 2025, I’m exploring a question that is directly related to the topics I explored in The Announcement series proper - what does effective activism for brands actually look like?

MAD Fest is a huge festival for brands and agencies that takes place each year in East London, and I was invited to take part in this year’s event by organiser Dan Brain, who it turns out is an avid Looking Sideways and Announcement listener.

As he put it in a very kind blog he wrote in the lead up to the show, ““I’ve been a big fan of Looking Sideways for some time now and I’m excited to bring a live version to MAD//Fest that will ask important questions like whether brands can use their reach, cash and influence for good, or if there’s a fundamental contradiction between sales growth and sustainability”

To help me answer these question, I spoke four brilliant guests, each experts on the topic in their own particular way: Finisterre CMO Bronwen Foster-Butler, activist Lauren MacCallum, CEO of B Corps Chris Turner, and author and purpose pioneer Thomas Kolster.

Among the questions I was interested in discussing:

- What role (if any!) should brands play in activism and using their scale, audience and money to address local, national and global issues? 

- Is purpose something all brands should establish, or an act of greenwashing that sounds good in an annual report but delivers little meaningful impact? 

- Are brand partnerships and activities an effective means through which to drive change?

What followed was a lively, passionate and very well informed discussion recorded in front of an equally engaged crowd - they’d put me in a prime slot on the big stage, much to my surprise - and we got through a lot in our allotted 35 minute stage time.

A note on the sound - a few audio teething issues meant we weren’t able to hear our fellow panelists super clearly, which might account for the somewhat strident way we’re all speaking to each other during this conversation. But hey, it was live, and that’s the way it goes sometimes.

Huge thanks to Dan and everybody at MAD Fest for getting me involved, to Bronwen, Lauren, Chris and Thomas - looking forward to hearing what everybody thinks.

For bonus and behind-the-scenes material, click here.

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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250 episodes of Looking Sideways! And to mark the occasion, I invited the great Jeremy Jones back for this second visit, six years after we recorded our first conversation for the podcast.

Much has changed in Looking Sideways land since that first chat. Back then, the show was basically me interviewing famous action sports types about their lives and careers. This was pre-Type 2, and certainly pre-The Announcement, and since then Looking Sideways has evolved into something pretty different.

All of which made Jeremy an especially fitting guest with whom to mark this milestone. Why? Because few high-profile professional snowboarders, surfers or skateboarders (if any, come to think of it) connect the worlds of performance and activism like Jeremy does.

As a pro rider, he is of course one of the greatest to ever do it. Certainly, he’s one of the most influential snowboarders ever, whether that’s through his own extraordinary feats, his company Jones, or his creative work as a proponent of what he calls ‘shralpinism’.

Then there’s his hugely influential activism. For right or wrong, in many ways Jeremy’s strategic work with Protect Our Winters has come to define winter sports activism over the last decades, and he’s certainly the figure who has come to be associated with what he refers to as the outdoor state’s response to the climate crisis.

All of which makes him the perfect guest to connect the past and present of Looking Sideways for this milestone episode: especially as he’s been such a supporter of my own work in recent years.

We caught up to record this episode in early July 2025, and it’s an open, relaxed and revealing conversation about politics, risk, family life, and what snowboarding means to Jeremy now in the classic Looking Sideways mould.

Hope you enjoy this episode, and thanks to everybody for supporting Looking Sideways over the last eight years.

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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