Why We Keep Showing Up: Nine Years of Startup Wisconsin Week

Startup Wisconsin Week starts today with events in 10 cities across the state until November 14th. In this special post, friend of StartMidwest Jacob Miller of Startup Wisconsin shares his thoughts after nine years of the event and what’s next.

In 2022, our CEO Andrew Verboncouer and I took over organizing Startup Wisconsin and Startup Wisconsin Week. We inherited something that had been running since 2017 out of Milwaukee, but we were based in Green Bay. Running events like this wasn’t new to us, but we’ve never managed state-wide efforts before.

Andrew and other locals that worked in tech had started a meetup for Northeast Wisconsin called Digital Fertilizer in the spring of 2013. From founder storytelling to hosting hackathons like Startup Weekend, we knew what we were getting into with a decade of doing this kind of thing.

We knew we wanted to rethink what Startup Wisconsin was and why it existed. New brand. New approach. New everything.

The first thing we did was refresh the brand to communicate that it was under new leadership more clearly. We knew we didn’t have the capacity and resources to do much more with it in year one. But we had a dream.

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I remember trying to find the words to describe it. The best answer I could come up with was that it just feels right. Like this is work that needs to exist, and if we don't do it, maybe nobody will.

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With both Andrew and I at Headway, we used ourselves, Headway resources, and sponsors to gain traction. It’s been finding the balance of maintaining the status quo with what people thought of Startup Wisconsin and Startup Wisconsin Week already, and then trying to figure out what is really the next step with this thing.

We’ve spent the last three years in listening mode. And that will continue:trying to just figure out where we can actually add value to Wisconsin’s startup and tech ecosystem. Not just add more events or duplicate efforts. 

The newsletter was phase one. We know awareness of what was going on across the state was a big problem. There wasn’t one place to find it all. By aggregating events, pitch contests, open accelerator applications, and news. Then we built up the database of those on our website to increase discoverability. All with the goal of amplifying what’s already going on.

Since 2022, we've tried to make Startup Wisconsin Week better based on what we heard from listening mode. Sometimes we nail it. Sometimes we don't. But we keep showing up, and  sometimes that’s the hardest part.

Last year around this time, Anna Lardinois of MKE Startup News asked me and Andrew a simple question: "Why do you do it? Why Startup Wisconsin?"

I remember trying to find the words to describe it. The best answer I could come up with was that it just feels right. Like this is work that needs to exist, and if we don't do it, maybe nobody will.

On a personal level, I'm extremely lucky that Andrew wants Headway to invest into the community through Startup Wisconsin. Andrew has been doing this work way longer than me. Quietly helping founders, making connections, supporting events. His impact isn't measurable, but it's everywhere. And that's kind of by design. We don't plaster Headway's name all over everything. We don't use Startup Wisconsin as a lead generation engine. Sure, we might get a few business opportunities because of the connections we make, but that's not our why.

We have a vision for Wisconsin's startup community. One that's exciting, helpful, kind, thriving, and generous. And the only way to build that is to actually show up and do the work.

Which brings me to the most important thing about Startup Wisconsin Week: it wouldn't exist without the countless volunteers across the state creating, coordinating, and hosting events in their cities.

This is truly grassroots.

The Greater Green Bay Chamber is helping with events in Green Bay. Our friends at gener8tor are helping host and collaborate. StartingBlock is bringing together founders in Madison. Rae Heggemeier Pederson and her team at Valorym are running things in Chippewa Valley. New North is hosting a pitch series, multiple economic development corporations are hosting pitch contests as well. The list goes on and it’s hard to name them all.

In my mind, many of these aren't “Startup Wisconsin” events. They're community events that happen to be during Startup Wisconsin Week. We just help amplify them and create a shared moment when the entire state is paying attention at the same time.

That distinction matters. Because Startup Wisconsin Week only works if it reflects what each community actually wants, not what we think they should want.

This year's theme - "Becoming Resourceful" - came from conversations we've been having all year. AI is changing everything about how startups get built. Founders need practical guidance on when to use AI, when to stay human, and how to do more with less.

But we're also seeing founder story sessions, pitch competitions, networking events, and coffee meetups. Because the best connections often happen over a beer or a cup of coffee, not in a conference room.

November 10-14, 2025 will be our ninth year. Over 500 events since 2017. More than 10,000 participants. But the numbers that matter most to me are the ones I can't measure: the founder who realized they weren't alone, the student who discovered Wisconsin's startup scene, the investor who found their next deal, the connection that turned into a collaboration.

I've also learned that progress is always greater than perfection. The newsletter might go out a few days late. We'll miss opportunities and make mistakes. But we'll keep showing up.

Because that's what ecosystem building actually looks like. Not polished press releases or perfect execution, but consistent effort from people who believe this work matters.

If you're in Wisconsin and you're building something, or thinking about building something, then Startup Wisconsin Week is your week.

Not because I'm telling you to show up, but because everyone else already is. And that's how ecosystems grow: one conversation, one connection, one week at a time.

We're still learning. Still listening. Still trying to make it better. And we'll be here next year doing the same thing.