Borderless AI’s Make It Click podcast begins with a question every founder, investor, and early employee has wrestled with: what makes a startup work before there is even a product, customers, or sometimes a company?
In Episode 1, host Willson Cross sits down with Matt Cohen, Founder and Managing Partner at Ripple Ventures, for an hour long conversation about early-stage investing, founder signals, startup failure, and what separates promising ideas from companies that can actually scale.
Cohen founded Ripple Ventures in 2018 after building a career across institutional finance, angel investing, enterprise software, and startup operations. Before launching the fund, he was the founding investor in Turnstyle Solutions, which was later acquired by Yelp. According to Borderless AI, Cohen did more than write a cheque, helping the early team recruit employees, drive sales, and raise capital.
That operator-first perspective shapes much of the episode. Cohen argues that early-stage startups rarely succeed because of a pitch deck alone. Instead, the conversation focuses on the signals that matter before the metrics are obvious: the quality of the team, the depth of the problem, the founder’s ability to recruit, and the discipline required to fundraise before product-market fit.
The episode also explores what Cohen describes as the “death valley” many startups face before reaching product-market fit. It is the stage where founders often need more than capital. They need operational guidance, practical playbooks, customer insight, investor relationships, and the resilience to navigate pivots, shutdowns, and second chances.
For Canada’s tech talent ecosystem, the conversation offers a useful look at how founders are evaluated before their companies are fully formed. Cohen discusses the traits that separate great founders from the rest, why many startups fail, and how early-stage investors think about risk. He also touches on the difference between Canadian and U.S. founder ambition, a recurring topic in conversations about how Canada can build more globally competitive technology companies.
The episode is especially relevant for founders, operators, early employees, and talent leaders because so much of startup success comes down to people. Before a company has brand recognition or scale, its ability to attract talent, build trust, and convince others to join the mission can determine whether the company survives long enough to find its market.
Cohen also brings a community-building lens to the conversation. In addition to leading Ripple Ventures, he hosts Tank Talks, a weekly podcast featuring founders, investors, and leaders shaping the future of technology and venture capital.
As the first episode of Make It Click, the conversation sets the tone for the series. It is not just about celebrating startup success after the fact. It is about understanding the early decisions, personal tradeoffs, and founder qualities that make success possible in the first place.
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.