Kyle Tsai, investment manager at Wayra, is one of our top 50 Rising Stars in corporate venturing for 2025.

Kyle Tsai was a product manager, a founder and a VC investor before coming to corporate VC. But before that, he worked as a wine sommelier, which is not as big a change as you might think. 

“Drinking wine is not too different to investing,” he says. Indeed, having to smell and taste wines over and over again is not far away from the levels of analysis a startup needs. 

“When you really taste the wine is when you really make the investment,” he says. “And every time you drink wine, there is an aftertaste – that is like post-investment in a startup. You have to take care of them through their entire journey to make sure it goes as well as possible.” 

Tsai is an investment manager at Telefonica’s Wayra unit, originating and managing deal flow for investments and business development opportunities with startups. Having been on both sides of the VC fence, he soon realised that there is plenty of scope for expanding how the industry can communicate, and he describes his deal-sourcing strategy as community-based. 

“CVCs are not that collaborative and we are not actually utilising our corporate resources or our corporate validation power,” he says. “I am very good at finding a group of people who share the same pain point, so that leads me to either find investors looking at a similar area or find a founder working on the pain point we want to solve.” 

Tsai wants to get to the point where he can explore new areas and technologies as an investor that could eventually impact Telefonica’s entire business. For now, the most fulfilling part of his work is finding startups that fit strategically. 

“When a really good wine came in, we called it ‘mariage’ – marriage, in French,” he says. “Right now, I am looking for the right marriage between a startup and a corporate. We have to make sure they echo each other, are really complementary and that they can grow together.”  

“Every time you drink wine, there is an aftertaste – that is like post-investment in a startup. You have to take care of them through their entire journey to make sure it goes as well as possible” 

See the full list of Rising Stars 2025 here.