Experience Milwaukee

Experience Milwaukee

Sipping whiskey and talking tech with Mason Cook, Managing Director of Mastercraft Ventures

A conversation that exposed a quiet contradiction in our tech ecosystem.

Steve Glynn's avatar
Steve Glynn
Jan 05, 2026
∙ Paid

I sat down with Mason Cook, Managing Director of Mastercraft Ventures, to talk candidly about what it really takes to build startups and a startup ecosystem in Milwaukee and Wisconsin.

We covered his path into venture capital.

What stuck with me most was how clearly Mason articulated the difference between multi-generational businesses and venture-backed startups.

Drawing on his experience living and working across the Midwest, Mason shared an optimistic but unsentimental view of Wisconsin’s tech future.

He summed it up with a metaphor that has stayed with me since. But you’ll have to listen for more on that.

» For paid subscribers: Listen to the full audio conversation I had with Mason below «

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