This Isn’t an Exit. It’s an Investment. Here's How I'm Doubling Down on Milwaukee.
I’ve spent 20 years building and listening in Milwaukee. Now I’m writing it all down.
Why this matters: if you’re ambitious and deciding whether Milwaukee is the place to build something meaningful, I believe that you can do work that matters, grow real relationships, and shape this city.
Hey Milwaukee,
A lot of you have been asking about what’s next for me and how you can support it. We’ll get to that.
I’m going to share something later in this newsletter that I think is exciting and important for both Milwaukee and Wisconsin. However, I also want to be sure you know where my head and heart remain even while I launch a sharp pivot with Experience Milwaukee in 2026.
First, I am still 100% committed to finding a new space for all of us to gather, connect, grow, and build. As I continue work to activate the building directly behind the current Experience Milwaukee at the Wantable Cafe, I’m having other meetings with other spaces, too. In fact, I have one this afternoon that could be a good fit for how all of us work in the Waker’s Point Innovation District.
Second, and speaking of the Walker’s Point Innovation District, I am also 100% committed to working with Common Council President Jose Perez to realize the potential of this initiative. We’ve had numerous meetings with stakeholders in the District and others who support, fund, and build tech in and around Milwaukee. As we continue to finalize infrastructure, we’ll have some cool things to announce as the year gets rolling.
So, What’s Next?
As some of you may know, Experience Milwaukee started as a podcast in my basement in 2018. By focusing on the people, places, and events that made the city amazing, it was my way of giving back to a community that embraced me since 2007 when I started building my first company.
Almost immediately after publishing the first podcast episode, Adam Derus joined in the fun. Over the next several years, Adam and I covered as many restaurants, bars, musicians, festivals and more that we possibly could in a weekly show.
Throughout the eight years of the podcast, and in addition to the show’s cultural focus, I would inject special episodes on business, tech, and innovation.
These are topics I am obsessed with. Well, as we approach 2026, I’m making a full pivot into Milwaukee’s innovation economy.
What started as a podcast is evolving by adding a weekly Substack about what’s working, and what’s not, in Milwaukee’s approach to technology and innovation.
Each week starting today, I’ll share what’s happening with the people building Milwaukee’s future, the frameworks they’re using, the behind-the-scenes progress (or roadblocks), and what we can learn from other cities doing things differently.
Because we can’t make Milwaukee smarter if we don’t step back and ask better questions.
My hope is you take what you learn from this newsletter to build faster and stronger in Milwaukee.
2026 Experience Milwaukee Innovation Tour
That’s why in 2026, I’m hitting the road for the Experience Milwaukee Innovation Tour: 12 cities in 12 months.
Rather than going to the hype capitals, I’m choosing to visit places like Boulder, Durham, Chattanooga, and Salt Lake City to see what real, local innovation looks like on the ground.
I’ll meet with leaders, makers, and organizers and bring back practical ideas, things to avoid, and reflections that might just apply here. Or not.
This Substack is where I’ll share my journey every Monday with one goal: to make Milwaukee better.
Here’s How You Can Help
If this all sounds like something you want to follow, or shape, or challenge, then please subscribe.
And share this with anyone you know who wants more for this city.
Because, as you’ve asked, this is exactly how you can help.
Thanks for being part of my past, present, and future.
Love you Milwaukee.
Steve
What ambitious readers should take from this:
Milwaukee can still be a place where your contribution is felt.
The right city is not always the biggest one. Sometimes it’s the one where you can create outsized impact.
If you’re thinking about whether to stay, look at where you can build trust, momentum, and long-term opportunity fastest.
I am so down for this!