Borderless AI’s Make It Click podcast is continuing its look at Canadian founders, operators, and investors with a conversation featuring one of the country’s most prolific business builders.
In Episode 3, host Willson Cross sits down with Andrew Wilkinson, co-founder and Chairman of Tiny, for a 70-minute conversation about building companies, buying businesses, avoiding the traditional venture capital path, and using artificial intelligence to operate more efficiently.
Wilkinson, based in Victoria, B.C., is the co-founder of Tiny, a publicly traded holding company often described as the “Berkshire Hathaway of the tech world.” The company owns more than 40 businesses, including AeroPress, Letterboxd, and Serato, and generates more than $250 million in annual revenue, according to Borderless AI.
The episode traces Wilkinson’s path from college dropout and local barista to entrepreneur, author, and holding company builder. It also explores the failures, personal turning points, and operating lessons that shaped his approach to business.
A central theme of the conversation is that building a large company does not always require following the traditional Silicon Valley script. Wilkinson built Tiny without venture capital, without a conventional board structure, and without selling businesses simply because a buyer appeared. Instead, the discussion highlights a quieter, ownership-focused model inspired in part by Warren Buffett: acquire strong businesses, operate them with discipline, and build for the long term.
For Canada’s tech talent ecosystem, the episode offers a useful perspective on entrepreneurship outside the venture-backed growth-at-all-costs model. Wilkinson’s story shows how founders can think differently about ownership, capital, hiring, and scale.
The conversation also touches on how AI is changing the way companies operate. Wilkinson discusses how AI agents can help businesses run leaner, allowing founders and teams to build without necessarily adding headcount at the same pace. That theme fits closely with the future-of-work questions many companies are now asking: what work should be automated, where human judgment matters most, and how teams can stay productive as AI tools become more capable.
The episode also gets personal. Wilkinson talks about the failures along the way, an ADHD diagnosis that reframed how he understood himself, why he stopped drinking, and the real cost of maintaining a public persona. Those reflections give the conversation a broader relevance beyond company-building tactics, touching on the human side of entrepreneurship, ambition, and financial freedom.
For founders, executives, HR leaders, and talent teams, the episode offers a practical look at what it takes to build durable companies while staying clear-eyed about the tradeoffs involved.
Watch the full episode of Make It Click below.
Borderless AI is a sponsor of Techtalent.ca. Through its Make It Click series, the company is spotlighting conversations with technology leaders about company building, talent, AI, and the future of work.