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Why'd You Think You Could Do That?

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by Sam Penny

42 episodes

Updated Daily

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Podcast Overview

They’ve swum oceans, scaled mountains, launched empires, and shattered expectations. But before they did any of it, someone, maybe even themselves, thought: “You can’t do that.” Hosted by Sam Penny, Why’d You Think You Could Do That? dives into the minds of people who said “screw it” and went for it anyway. From adventurers and elite athletes to wildcard entrepreneurs and creative renegades, each episode unpacks the one question they all have in common: “Why'd you think you could do that?” If you’re wired for more, haunted by big ideas, or just sick of playing it safe, this is your show.

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7/22/2025

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Recent Episodes

June 22, 2026

From Accountant to Antarctic Explorer | Ian Evans

What makes an ordinary person attempt extraordinary things? In this episode of Why’d You Think You Could Do That?, Sam Penny sits down with adventurer, filmmaker and Chartered Accountant Ian Evans. Ian has spent decades pushing beyond conventional limits, from climbing some of the world's highest mountains and cycling across Australia to skiing 900 kilometres to the South Pole at nearly 60 years of age.But Ian's story isn't about records, fame or elite athleticism.It's about curiosity, resilience and discovering what happens when you stop asking "Can I?" and start asking "Why not?"Ian shares the lessons learned from mountaineering disasters, solo expeditions, rebuilding his life after losing almost everything, and creating the Elora Adventure Film Festival, a festival designed to inspire ordinary people to pursue extraordinary lives.If you've ever felt the pull of adventure, wondered whether you're capable of more, or needed a reminder that it's never too late to start, this conversation will stay with you long after it ends. In This Episode<ul><li> Growing up in England and the early signs of a lifelong explorer </li><li> Why Ian left school early and became a Chartered Accountant </li><li> The childhood fascination with Shackleton, Scott and Antarctica </li><li> Climbing Kilimanjaro and discovering a passion for adventure </li><li> Pursuing the Seven Summits and lessons from high-altitude mountaineering </li><li> Facing death, risk and fear on some of the world's toughest mountains </li><li> The terrifying fall on Mount Elbrus that changed everything </li><li> Cycling solo across Australia and crossing the Nullarbor </li><li> Why solitude can be one of life's greatest teachers </li><li> The power of stepping outside your comfort zone </li><li> Skiing to the South Pole at nearly 60 years old </li><li> The hidden mental cost of extreme expeditions </li><li> Losing his marriage, career and nearly his life within 60 days </li><li> Rebuilding from rock bottom using a simple whiteboard </li><li> Creating the Elora Adventure Film Festival </li><li> How storytelling inspires ordinary people to do extraordinary things </li><li> Why adventure has nothing to do with age </li><li> The difference between quitting and moving on </li><li> What bravery really means </li></ul>Memorable Quotes"I choose something that I want to do, not that I can do.""The more you're outside your comfort zone, the richer your life will be.""Anything's possible. You don't have to be talented. You just have to work on it.""The best expedition is the next one.""It's never too late. It's only too late if you decide it is."About Ian EvansIan Evans is a Canadian adventurer, speaker, filmmaker and former Chartered Accountant who has spent decades pursuing ambitious expeditions around the world.His adventures have included climbing major peaks across multiple continents, cycling across Australia, skiing to the South Pole, flying aircraft, and producing the documentary Lunatic, which chronicles his Antarctic journey.Today, Ian channels his passion for exploration into the Elora Adventure Film Festival, where he showcases inspiring stories of ordinary people achieving extraordinary things and encourages audiences to embrace adventure in their own lives.Resources & LinksIan Evans<ul><li> Website: <a href="https://ianevans.ca">ianevans.ca </a></li><li> Elora Adventure Film Festival: <a href="https://eloraadventurefilmfestival.ca">eloraadventurefilmfestival.ca </a></li></ul>Listen If You Want To Learn<ul><li> How to build confidence through action </li><li> Why adventure is accessible to ordinary people </li><li> How to overcome fear and self-doubt </li><li> The role of discomfort in personal growth </li><li> What extreme expeditions teach about life and business </li><li> How storytelling can spark life-changing decisions </li><li> Why it's never too late to pursue a bold dream </li></ul>If you enjoyed this episode, subscribe, leave a review and share it with someone who needs a reminder that their next adventure might be closer than they think.

November 26, 2025

David Keohan – The Man Bringing Ireland’s Lost Stone-Lifting Culture Back to Life

Centuries ago, young men in Celtic villages proved their strength and identity not in gyms but by lifting stones older than memory — rites of passage where pride, community, culture, and strength were one.That tradition vanished… until David Keohan rediscovered it.In this conversation, David reveals how the ancient Irish stones — some untouched for generations — are reawakening national pride, reconnecting people with ancestry, and giving young men and women a pathway back to meaningful challenge.From kettlebell world champion to cultural archaeologist of strength, David’s story shows how one person with a spark of curiosity can ignite a global movement.“The stones don’t care about who you are — they only want to be lifted.” — David Keohan📌 Based on our conversation recording — source: 🔥 Key Episode Themes<ul><li>Reviving ancient rites of passage — what lifting stones meant in Irish villages for thousands of years</li><li>COVID as the unlikely catalyst that led to the rediscovery of a forgotten strength culture</li><li>Ireland's lost cultural roots — and how colonialism wiped many of them from memory</li><li>Why people weep when they lift these stones</li><li>The moment David lifted Ireland’s most sacred stone — and a crowd sang him into history</li><li>How stone lifting is now spreading worldwide, including Australia and the USA</li><li>The powerful message for young people craving purpose and meaning</li></ul>🏋️ Who is David Keohan?<ul><li>Two-time World Champion in kettlebell sport</li><li>Founder of the movement restoring Ireland’s stone-lifting traditions</li><li>Cultural advocate working with archaeologists, historians and local communities</li><li>Creator of the documentary Made of Stone</li><li>Currently writing a book on the history, mythology and revival of stone lifting</li></ul>📍Episode ChaptersTimeChapter00:00 | The myth, the stones, and the revival begins 07:00 | From overweight dad to world champion 10:00 | The pandemic and a spark in the garden 14:00 | Lifting the legendary Fianna Stone in Scotland 18:00 | First discovery on the Aran Islands 26:00 | The moment that brought an entire island to tears 39:00 | Ancient strength on mountaintops 46:00 | What villages gain when stones are rediscovered 53:00 | A movement that’s now circling the world 59:00 | Why young people are craving real challenge 1:05:00 | A call to action: “Don’t overthink it — just start”🎧 Listen + Watch 📸 Featured Stone Locations in This Episode<ul><li>Inis Mór — Mór na Port Véal an Dúin</li><li>The Seafin Stone, County Derry</li><li>Wakes & Harvest stones in County Clare</li><li>…and many more emerging from the earth once again</li></ul>🧭 Connect with David KeohanInstagram: @indianastones Documentary: Made of Stone – RTE (global release pending)🚀 Ready to Find (and Lift) Your Impossible?David reclaimed a national tradition.You have your own stone to lift.If you’re a business owner who wants to build a company that runs without you — and one day sells for a life-changing exit — let’s work together.👉 Work with Sam 1-on-1 <a href="https://sampenny.com/action">https://sampenny.com/action</a>Or explore all coaching & programs: <a href="https://sampenny.com">https://sampenny.com</a>Let’s make your impossible… inevitable.

November 12, 2025

Pedalling Beyond Borders: Dr Kate Leeming on Purpose-Driven Adventure

What drives someone to cycle across Africa, through Siberia, over Australia’s wildest tracks, and into the remote corners of the Himalayas — not for glory, but for change?In this episode, Sam Penny sits down with Dr Kate Leeming, global explorer, educator, and the powerhouse behind Breaking the Cycle. With over 100,000 km of cycling expeditions across every continent, Kate shares how she uses extreme endurance journeys to shine a light on poverty, resilience, education, and environmental justice.Together, they dive into:🚴 Kate’s early spark for exploration and sport 🌍 Her most transformative expeditions — from the Canning Stock Route to the Skeleton Coast 🧭 What it means to have a “North Star” mission 📚 How she brings global stories into classrooms through immersive education 💡 The mindset that helps her turn adversity into impact ✨ Why true adventure isn’t about conquering — it’s about connectingKate isn’t just an explorer — she’s a builder of bridges between cultures, communities, and classrooms. Her stories remind us that no matter the terrain, purpose can carry us further than fear.🔗 Connect with Dr Kate Leeming🌐 Website: <a href="https://www.breakingthecycle.education">breakingthecycle.education</a> 📸 Instagram: <a href="https://www.instagram.com/leeming_kate/?hl=en">@leeming_kate</a> 📘 Book: Out There and Back 🎥 Watch her films, access school resources, and follow her next expedition💬 Loved this episode? Share it with someone who’s ready to choose the uphill path.🧭 Follow Sam Penny on Instagram <a href="https://www.instagram.com/90dayswithsam/?hl=en">@90dayswithsam</a> and visit <a href="https://sampenny.com">sampenny.com</a> for more episodes of Why’d You Think You Could Do That?

42 total episodes available

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What is Why'd You Think You Could Do That??: They’ve swum oceans, scaled mountains, launched empires, and shattered expectations. But before they did any of it, someone, maybe even themselves, thought: “You can’t do that.”

Hosted by Sam Penny, Why’d You Think You Could Do That? dives into the minds of people who said “screw it” and went for it anyway. From adventurers and elite athletes to wildcard entrepreneurs and creative renegades, each episode unpacks the one question they all have in common:

“Why'd you think you could do that?”

If you’re wired for more, haunted by big ideas, or just sick of playing it safe, this is your show.
How often does this podcast release new episodes?: This podcast updates daily.
Where can I listen to this podcast?: This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
Does this podcast accept guests?: Yes, this podcast regularly features guests.

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