In this episode of Outlaws, we sit down with Sam Flynn, former litigation lawyer and co-founder of Josef, an AI automation platform transforming how legal work gets done around the world.

Sam started on the traditional legal path. Law school. Top firm. Supreme Court clerkship. The funnel was working exactly as designed. But along the way, something shifted.

What began as volunteering with civil liberties organisations led to a lightbulb moment: when Sam and his collaborators built a simple legal tool to help people navigate Victoria’s infringement system, 30,000 people used it on day one. Within a month, 60,000 people had accessed it. The law eventually changed.

That experience sparked Josef. Today, the platform is used by organisations like Bumble, L’Oreal and Bupa, as well as community legal centres and universities, to automate legal questions, generate documents and streamline workflows. At its core is a belief that self-service legal tools, when properly supervised, can help close the access to justice gap rather than widen it.

But this conversation isn’t just about legal tech.

Sam talks openly about what he had to unlearn from legal training. The obsession with risk. The fear of embarrassment. The idea that failure defines you. He shares the moment he realised that striving is far less embarrassing than staying small to avoid criticism.

We explore identity shifts, burnout, creativity, storytelling in business, and why lawyers statistically make “bad founders” unless they learn to turn down the risk dial.

If you’ve ever felt pulled toward something different.

This episode is your reminder: you can follow your curiosity. You can build something new. You can strive anyway.

If you’re a lawyer wondering whether the traditional path is right for you, or you’re curious about legal tech, AI in law, or alternative career options for law graduates, this episode offers both inspiration and practical insight.

You don’t have to abandon law to reinvent it. Sometimes you just have to step into the arena.

Theodore Roosevelt’s speech - The Man in the Arena

Sam on LinkedIn 

Sam’s newsletter: https://www.linkedin.com/newsletters/scooped-7183318477628223488/

Sam's Fireside Chat series with Tom Dreyfus https://open.spotify.com/show/2tBSFrxTSO30Pknjmyb7RG

Josef

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Hosted and produced by Shayla Strapps and Kate Offer