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What Makes a Startup “Click”, Before It Even Exists?
Guest
Matt Cohen
Matt Cohen founded Ripple Ventures in 2018 after a successful run in institutional finance & angel investing. Before launching the fund, Matt cut his teeth as the founding investor in Turnstyle Solutions—acquired by Yelp—where he went beyond just writing checks. Matt rolled up his sleeves helping the early team recruit employees, drive early sales, and help fundraise from investors.
After selling Turnstyle, Matt noticed a gap in the early-stage market where founders needed more than just money, they needed operational guidance, seasoned networks, and practical playbooks to survive death valley where most startups die before eventually reaching PMF.
Matt joined a Toronto-based fintech startup Street Context (Acquired by Thoma Bravo/BlueMatrix), selling enterprise software to global financial institutions and moved to Boston to lead enterprise sales. Upon returning to Toronto, he built a strong angel portfolio and his track record caught the attention of family offices and high-net-worth investors, ultimately leading to the launch of Ripple Ventures in 2018. Today, Matt is all about:
- Empowering early-stage founders with mentorship, tangible support and global connections.
- Avoiding common pitfalls by sharing lessons from his own entrepreneurial, operational and investing journey.
- Building an engaged community through his weekly podcast, “Tank Talks,” where he interviews founders, investors, and global leaders shaping the future.
Description
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.
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