Why'd You Think You Could Do That?

Welcome to Why’d You Think You Could Do That?
Hosted by Sam Penny: entrepreneur, endurance athlete, and Coach for the Brave.
This podcast is for anyone who’s ever had a bold idea… and wondered if they were crazy to try it.
Each week, we dive into the minds of people who’ve done the extraordinary, not because they had permission, but because they chose to start before they felt ready.
From founders and creators to athletes and adventurers, you’ll hear raw, honest conversations about the moments that changed everything.
No filters. Just real stories of guts, grit, and going all in.

What to Expect:
  • Thursdays: Interviews with bold individuals who’ve built, challenged, or created something that shouldn’t have worked, but did.
  • Tuesdays: A short Bravery Digest to remind you that courage isn’t something you wait for, it’s something you practice.
If you’ve ever felt like you weren’t “ready”, this is your reminder:
You don’t need permission to do something extraordinary.
🔔 Subscribe now. New episodes every Tuesday and Thursday at 5am AEST.
🔗 Resources & Links
→ Watch or read the Bravery Digest: https://sampenny.com/blogs/the-bravery-digest
→ Explore all episodes: https://sampenny.com/podcast
→ Book a discovery call: https://sampenny.com/strategy

Creators and Guests

Host
Sam Penny
Sam Penny is an adventurer, entrepreneur, and keynote speaker who lives by the mantra “Say YES! to the Impossible.” From swimming the English Channel in winter to building and selling multi-million-dollar companies, Sam thrives on pushing boundaries in both business and life. As host of Why’d You Think You Could Do That?, he sits down with ordinary people who have done extraordinary things, uncovering the mindset, resilience, and bold decisions that made it possible — and showing listeners why their own impossible is closer than they think.

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.

Speaker 1:

Have you ever looked at someone doing something extraordinary and thought, why do you think you could do that? Well, good. That's exactly what we ask here. I'm Sam Penny, extreme swimmer, entrepreneur, and coach for the brave. Each week, I sit down with people who've done the impossible, not because they were fearless, but because they started before they felt ready.

Speaker 1:

From business builders to endurance athletes to bold creators, these are the stories of people who move before the path is clear. This show isn't about hacks or shortcuts. It's about decisions that change your life and the courage to make them. Because bravery isn't a feeling, it's a choice. And this show, it's your reminder that you don't need permission to do something extraordinary.

Speaker 1:

So subscribe to why do you think you could do that now. New episodes drop every Thursday at 5AM, and every Tuesday, you'll get a short punch of bravery to kick start your week. So let's go.