SO MANY QUESTIONS... an interview podcast with curiosity, heart, and a little weirdness

Conversations with interesting people in art & design, entertainment, sports, and tech.

What drives someone to create? To compete? To build something new?

So Many Questions is a conversational podcast hosted by Kendall Guillemette. Each episode is an unscripted, long-form conversation guided by curiosity. Exploring ideas, lived experience, and the questions that shape how we see the world.

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So Many Questions is a space for listening, reflection, and thoughtful dialogue. Instead of hot takes or quick answers, the show focuses on slowing down and making room for complexity, nuance, and honest curiosity.

If you enjoy conversations that are human, exploratory, and unpolished, you’re in the right place.

The show can be found wherever you get your podcasts:

About the Host

Kendall is a designer and technologist who has spent decades working on the web. He approaches conversations as a listener first. Asking open, reflective questions and allowing guests space to think. The goal is to lead guests into conversation and explore questions together. Not for the highlight reel, but for the real story. The detours they took. The values that ground them. The moments that changed everything.

We talk about more than what people do. We talk about who they are and how they got there. The ideals they follow, the contradictions they carry, the joy and loss that shaped them along the way.

Real conversations are rarely tidy, and that's what makes them beautiful. Sometimes it's funny. Sometimes it's tender. Always real.