Make it Click

Nick Frosst is a co-founder of Cohere, the Toronto-based enterprise LLM company valued at $7 billion. In this episode of Make it Click, Willson sits down with Nick to talk about why Cohere bets exclusively on B2B, how on-prem deployments protect customer data in regulated industries, and why the consumer AI race has economics that don’t add up. Along the way, Nick shares his contrarian take on AGI...

Clio’s first investor found Jack Newton through a random blog post that almost never got read. Dennis Pilarinos sold his first company to Apple, then went back to building from scratch with Unblocked. In this episode, Willson sits down with Jack (CEO, Clio) and Dennis (CEO, Unblocked) to talk about the sliding door moments that define companies, why AI is transforming legal and developer tooling f...

In this episode of Make it Click, Willson Cross sits down with Andrew Wilkinson in Victoria, BC to trace the full arc, from college dropout pouring espresso shots to quietly becoming one of Canada's most prolific business builders. He gets honest about the failures along the way, the ADHD diagnosis that reframed everything, why he stopped drinking, and how AI is now letting him build without s...

In this episode of Make It Click, Willson (Borderless AI's Founder), sits down with Andrew Graham, CEO & Co-Founder of Borrowell, to learn what it actually takes to build a lasting FinTech company in Canada, without a idea or a roadmap (and in Andrew’s case, with a newborn at home).From hot-desking at TMU's Digital Media Zone to leading a platform trusted by nearly 4 million Canadians,...

In the first episode of Make It Click, hosted by Borderless AI Founder Willson Cross, we sit down with Matt Cohen, Founder & Managing Partner at Ripple Ventures, to unpack what actually makes a startup work, before there’s even a product, customers, or sometimes even a company. From backing founders at the idea stage to helping companies navigate pivots, shutdowns, and everything in between, M...