Borderless AI’s Make It Click podcast continues its series of conversations with Canadian technology leaders by turning to one of the country’s most experienced early-stage investors.
In Episode 6, host Willson Cross sits down with Boris Wertz, General Partner at Version One Ventures, for a one-hour conversation about venture capital, founder ambition, artificial intelligence, marketplaces, Canadian deal flow, and why the biggest outcomes in technology are increasingly concentrated among a small number of breakout companies.
Wertz is the founding partner of Version One Ventures and a leading early-stage technology investor in North America. Before becoming a full-time investor, he built JustBooks, an online marketplace for used and out-of-print books. The company was acquired by AbeBooks, which was later sold to Amazon.
That founder-to-investor journey shapes much of the episode. Wertz brings the perspective of someone who has built, sold, and backed technology companies, and now deploys roughly half a billion dollars in Canadian capital into early-stage, mission-driven founders.
The conversation arrives as Version One continues to double down on its strategy of backing companies before their categories become obvious. In the episode, Wertz discusses the firm’s new $78 million Fund Five and $30 million opportunity fund, which give Version One more room to support breakout companies as they scale.
The episode also highlights some of the companies that have shaped Version One’s track record, including Clio, Jobber, Ada, and Coinbase. For founders and talent leaders, those examples point to one of the episode’s central themes: the largest outcomes often come from companies that look early, unusual, or non-consensus before the market catches up.
For Canada’s tech talent ecosystem, the conversation offers a useful look at how venture investors think about ambition, timing, and category creation. Wertz explains why outlier companies matter so much to the economics of venture capital, how investors evaluate founders before the opportunity is obvious, and why early conviction can matter more than consensus.
The discussion also touches on artificial intelligence and its impact on the application layer. As AI changes how software is built, distributed, and adopted, founders are being forced to rethink product strategy, defensibility, and what it means to build a lasting company in a fast-moving market.
Wertz also shares his perspective on marketplaces, one of his longstanding investment areas, as well as the strengths and challenges of Canadian startup deal flow. For Canadian founders, the episode offers a reminder that global ambition, category insight, and the ability to attract talent can matter just as much as geography.
As with other episodes of Make It Click, the conversation is especially relevant for founders, operators, early employees, investors, and talent teams trying to understand how enduring companies are built. Wertz’s perspective shows that while venture capital may be a numbers-driven business, the best investments often begin with people who see a market differently before everyone else does.
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.