Make it Click

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 scaling headcount.Most founders think the only path to building something big runs through Sand Hill Road. Andrew Wilkinson proves otherwise.Andrew is the co-founder of Tiny, a holding company that owns 25+ businesses, including AeroPress, Letterboxd, and Serato, generating over $250M in annual revenue. He built it without venture capital, without a board breathing down his neck, and without sacrificing the businesses he loved to the highest bidder. He also wrote the book on it, literally: Never Enough: From Barista to Billionaire.If you've ever wondered whether there's a smarter, quieter way to build wealth without giving away your company, this one's for you.You'll hear about: the Warren Buffett-inspired acquisition model that changed everything · why B2B SaaS might be the next e-commerce · using AI agents to run businesses lean · the real cost of public persona and people-pleasing · and what financial freedom actually feels like when you get there.Key moments: 00:00 – Introduction04:38 – The $500 BBQ job that started everything05:38 – How Andrew lost it all on cat furniture and an online DJ school06:21 – The Warren Buffett idea that became Tiny07:00 – AeroPress, Letterboxd, Serato — following passion into acquisitions14:00 – Why Andrew never raised venture capital22:00 – The difference between being rich and being free31:00 – The ADHD diagnosis that reframed his entire career38:00 – Why he stopped drinking and what changed45:00 – Divorce, vulnerability, and the email that broke all his records52:00 – Why B2B SaaS might be the next e-commerce57:00 – Using AI agents and Claude Code to run businesses lean01:04:00 – Two meetings a week and total freedom — what his days look like now

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, Andrew shares how he went from political staffer to Harvard MBA to corporate executive and why he walked away from all of it to solve a problem he couldn't stop thinking about.- Why you don't need an idea to start a company, just a problem worth solving- The double-sided fundraise nobody warns you about when building a lending business- How Borrowell turns competitor ad spend into their own growth- What building a remote-first Canadian company actually looks like at scale- Why there's never a perfect time to take the leap (and why that's actually good news)If you've ever wondered what separates founders who survive the early chaos from those who don't, or what it really looks like to build something meaningful over a decade in Canada, this conversation is worth your time.Because sometimes, the thing that makes a company click… is falling in love with the problem before you ever find the solution.

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, Matt shares how he evaluates early signals most people miss and why team, problem, recruiting, and fundraising matter more than any pitch deck.In this episode, we get into:- The traits that truly separate great founders from the rest- Why many startups fail - How early-stage investors think about risk, pivots, and second chances- The difference between Canadian and U.S. founder ambition- What founders need to figure out about their life before starting anythingIf you’ve ever thought about building a company, or wondered why some ideas take off while others stall, this conversation offers a clear look at what’s really happening behind the scenes.Because sometimes, the thing that makes a company “click”… isn’t what you think.--- Keep the conversation going: Follow Borderless AI on LinkedIn: linkedin.com/company/hireborderlessConnect with Willson: https://www.linkedin.com/in/willsoncross/Connect with Matt: https://www.linkedin.com/in/matt-cohen1/Interested in diving deeper? Check out our Media Lab: https://www.hireborderless.com/media-lab