From a farm town in Ohio to penthouse events with billionaires in Chicago—Andrew Gunderman’s journey is anything but ordinary. By his early twenties, he had already founded and sold a startup, built founder communities from scratch, and begun curating some of the city’s most exclusive circles of entrepreneurs, investors, and influencers.

In this conversation, Andrew joins Mike Shannon and Corey Ferengul to unpack the strategy behind building Renowned Chicago, why exclusivity works when it’s paired with openness, and how relationships—not just capital—can accelerate a founder’s trajectory. He shares how aggressive outreach, mentorship, and an obsession with learning shaped his path, and why he believes networks can be one of the most valuable assets an entrepreneur can build.

We also dive into the evolving world of creators and influencers, the hidden leverage in connecting siloed communities, and how AI is already beginning to reshape how networks form.

If you’ve ever wondered how to break into circles that feel closed off—or how to turn relationships into real opportunities—Andrew’s story offers a playbook worth studying.