We’re back for Episode 3 of Season 2 of The Future With Friends, and this time Simon Waller (or should we say Bigsy) is joined by his long-time friend Anthony “Richo” Richardson, one of the first people he met when he relocated to Melbourne. This isn’t a professional connection, more a camping and degustation buddy from years gone by. It’s a friendship that’s stretched across decades, which gives the conversation a very different kind of honesty and ease.

The theme of this episode is The Future of Regret, based on a scenario Richo has written, set 42 years into the future. It’s a deeply reflective exploration of what life, meaning, and responsibility might look like in a future shaped by radically extended lifespans, AI-driven education, and accelerating technological change.

Richo brings a grounded, human lens to the conversation, imagining everyday moments that make the future feel tangible, like a 94-year-old still cycling with friends, while also surfacing the emotional weight of what gets lost or left unresolved across such long lives.

The conversation moves beyond fascination with technology and into more uncomfortable territory. They explore how extended lifespans might reshape our relationship with purpose, regret, and legacy, and whether having “more time” actually makes us more fulfilled or simply delays the things we avoid confronting today.

Underneath it all is a quieter, more confronting question about inequality, opportunity, and what kind of future we are actually building for each other.

As always, the conversation is rooted in lived experience as much as it is in future thinking. Simon and Richo reflect on the choices we make now as parents, citizens, and professionals, and how those choices quietly shape the emotional and cultural inheritance we pass on to future generations.