I sat down with Andy McLoughlin, Partner at Uncork Capital and former founder who built and scaled Huddle, to talk about the transition from operator to early-stage investor and what he’s learned on both sides of the table.

Andy shared lessons from founding Huddle and navigating a product exit, and how those experiences shape the way he evaluates startups today. We discussed why some of the most durable companies are built in “unsexy” markets, what separates must-have products from nice-to-haves, and how investors actually make decisions when conviction forms early.

We also dug into Andy’s leadership philosophy, how founders can build products that truly stick, and how early-stage venture is evolving as new technologies reshape the market.

If you’re building, exiting, or thinking about what makes a company indispensable, this episode is for you.