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In just five years, Upper Bound has grown from a 400-person birthday party to one of Canada’s largest AI-centred events, drawing in thousands of people each year.  But it isn’t the only thing that has changed: the way we talk about and use machine learning is also completely different in 2026. On the latest episode of Approximately Correct, Stephanie Enders joins to discuss how the conversation around AI has shifted in recent years. As Amii’s Chief Delivery Officer, she oversees a large portfolio that includes the conference, which brings together academics, business leaders, and anyone interested in learning more about AI. 

“To grow to 8,000 people in five years, I don't think that was on anyone's wish list,” she tells host Scott Lilwall.

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“But we kept on growing and responding to what people really enjoyed, which was like deep access to people who think deeply about this technology.”

Enders notes that one of the biggest changes over the years has been how much more connected all parts of the AI ecosystem have become. In the first year, academic lectures and business sessions were largely separated from one another. But now, machine learning is much more interconnected and interdisciplinary. The barriers between research, adoption and innovation have broken down. Spaces like Upper Bound are important for people from all levels of familiarity and technical knowledge to be able to meet and share ideas. “Any of those barriers that we can remove that make it easy for the folks that love to go into a room and have a conversation,” she says.

Check out the full episode for more from Stephanie Enders on how the way we talk about AI is changing.

Approximately Correct: An AI Podcast from Amii is hosted by Alona Fyshe and Scott Lilwall. It is produced by Lynda Vang, with video production by Chris Onciul. Subscribe to the podcast on Apple Podcasts or Spotify.