Jay’s bio:

• Jay Kolbe, a Milwaukee area resident, is a 20-year communications pro and co-founder / managing partner of Impact Partners, a New York-based strategic communications and growth advisory firm.

• He works closely with high-net-worth individuals, family offices, investors, and emerging technology companies.

• He also advises a wide range of technology and media-related brands and is known for helping founders, firms, and leaders create sharper, more ownable narratives around who they are and why they matter.

AI’s summary of my interview with Jay:

• Jay breaks down why so many founders, companies, and institutions still struggle to communicate what makes them truly differentiated and why simply “knowing your audience” isn’t enough if you haven’t clearly defined your own narrative first.

• He offers a sharp outside-insider perspective on Milwaukee and Wisconsin: a place with real substance, pride, and values, but one that too often under-owns its wins, hesitates to tell its story, and leaves too much room for bigger coastal markets to define the conversation instead.

• Steve and Jay get into one of the most uncomfortable but important tensions in the region’s tech ecosystem: why there can still feel like more talk than building, more protection of the status quo than support for what’s next, and why that creates real friction for ambitious people trying to scale something here.

• More than anything, this episode is about urgency. Jay argues that honest conversations, even uncomfortable ones, may be exactly what Milwaukee needs if it wants to become the kind of place that not only produces innovation, but actually owns it, supports it, and keeps it.

As I tell my kids: having hard talks is hard. But we need to do it. And we can do it in a respectful, caring way. That’s why I’m grateful for Concurrency and Secure Compliance Solutions who encourage and support me in making Milwaukee better.

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Why the hell am I talking to a New York PR guy from Iowa about tech and innovation in Wisconsin?

I believe to get better as a city we must, from time to time, get outside of Milwaukee for perspectives on what’s happening with tech startup founders, investors, etc., in the rest of the world.

Jay Kolbe is the guy to offer an expert POV on that.

From the moment I hit record, He and I got right into it.

As Jay was schooling me on the importance of telling stories through unique, ownable narratives, especially for founders and tech ecosystems, I paused.

I asked myself: is Milwaukee telling its best tech story?

Am I telling Milwaukee’s best tech stories?

For a few minutes, the communication strategy conversation spins me into a bit of anxiety.

I got a little worried that my recent grumpy nature blended with telling the truth about Milwaukee’s tech ecosystem might be too aggressive.

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Jay coined this word to describe my state of grumpiness as “anticappointment“: that I see what’s possible but I’m running into things here in Milwaukee that are stopping them from happening.

 For people who are genuinely some of the most honest people on the planet, Wisconsin is not honest with itself about the challenges that business and innovation face in the state.

Let’s take a step back.

We love Milwaukee.

However, are we allowing that MKE love, our strong civic pride, to cloud what we need to do to move forward and make the city better and finally manifest our potential?

If so, on what platform can we compete?

Integrity.

That’s what tech company builders on the coast want, Milwaukee!!

Why aren’t we leaning into that?

Let me be loud and clear why. WE ARE NOT OWNING OUR STORY!

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 There are best practices of how you create innovation environments that Wisconsin has not quite figured out yet.

Like what?

Exactly what I asked (even though I knew what).

Like aligning our communities (such as Madison <> MKE, c’mon!).

Aligning our effort.

Aligning our story.

And eliminating the damn silos!

We can get there, I know we can.

But it’s going to take stronger leadership and a whole lotta work.

I’m in. LFG.

Here’s my full interview with Jay:

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» You can also listen on Spotify here. «

Tarik’s quick bio:

• Currently Tarik is Director of Strategy and Innovation at Radio Milwaukee.

• Tarik has been a Milwaukeean for 20 years and has had a significant, positive impact on our community.

• If you know Tarik, you know how much he loves music and helping other people understand things around them, which is driving his work in AI.

AI’s summary of my interview with Tarik:

Btw, don’t get pissed about me using AI. My personal write up is below.

• Tarik is building Crate, a music research and discovery platform he describes as if Claude, Spotify, Pitchfork, and Wikipedia had a baby. Crate is designed to help people go deeper than passive listening and understand influence, context, and connection across artists.

• Tarik sees AI less as hype and more as a creative and civic tool, pointing to projects he’s building around music, public budgets, elections, and policy accessibility, with a strong belief that the same ambition coming out of Silicon Valley could be redirected toward helping people and communities.

• Tarik believes too much of the current AI conversation is stuck between hype and doom, while missing the more nuanced middle: what the technology actually is right now, what it can and can’t do, and how real people might use it in practical ways.

• He’s energized by building again, but also blunt that Milwaukee still has a lot of talk and not enough support for actual builders and that unless the city gets better at recognizing and backing people doing real work, many of them will keep finding that support somewhere else.

Real quick: I’m super stoked to be sponsored by Concurrency and Secure Compliance Solutions. They help to keep the Experience Milwaukee machine running so I can bring stories like this to life.

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Tarik Moody and I have been Milwaukee fans and friends for a long time.

Over the last 20 years, Tarik and I, sometimes together and sometimes just both in the same city, have been building community.

In large part, that’s why it was important to get a gauge from him on the tech temperature in Milwaukee.

When you want a healthy dose of what’s up, where honesty meets reality, Tarik is your guy.

In addition to community, Tarik is now building digital platforms at scale. For the latter, he’s using all kinds of AI tools.

One of the platforms he’s built that he really loves is called Crate. He describes it as a music research and discovery platform that you’d likely expect if Claude, Spotify, Pitchfork, and Wikipedia had a baby.

What Tarik is doing provides a glimpse into what’s currently inspiring people to act on problems by building AI-powered apps, whether they have a technical background or not.

Thought I don’t always know the reference points Tarik uses, here’s what I do know: he moves with a high level passion, purpose, and integrity. Even when, no, especially when he builds something to just see it exist.

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This is what people invest in? Betting on war?

“With all this brain power to solve things and build things to make lives better and help people and they’re not doing that? I’m like, I wanna use that same ambition and creativity in Silicon Valley, but flip it on its head and help society.”

Like anything else, when you ask Tarik what he thinks about what’s getting media attention in the AI space, you’re going to get the unfiltered truth.

He thinks that, in the media, all that’s being covered are big dollar investments or doom in gloom points of view about AI.

Nothing in the middle, where Tarik operates, under the radar here in Milwaukee.

“I'm very fascinated by how to make policy and politics more accessible using AI. I think that's a power that people don't have. We don't really know what our Congress people are doing. We don't know what our Mayor is doing. The data is there. It's just figuring out how we get this data in a way that makes it easy and accessible for people to understand what's going on.”

AI, along with people like Tarik, can democratize data like never before. That’s something that inspires Tarik at a level he’s not felt in a while.

With an education in architecture (yes, designing buildings), Tarik loves the building aspect of technology.

From researching and designing the vision that solves a problem to building and launching the platform to the world. Every step is important to Tarik.

And he’s gotten quite good at it. Especially at the various hackathons he’s not only participated in, but has won.

However, is Milwaukee the city he needs it to be to support him as he continues to build?

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There are great people doing stuff, but they're just not getting the love. The people in charge probably need to step aside and let people who are building be put in charge.

I worry about Tarik.

Not in the “will Tarik be ok?” kind of way. He will be just fine.

More in the “will he stay in Milwaukee?” kind of way.

Because I continue to see our brightest builders leaving the city they love.

Those who stay, and maybe this is worse, do so and our leaders don’t seem to care.

Both of which inform Tarik’s point of view about Milwaukee’s tech hub aspirations.

Listen, I know Tarik’s words might hit some people hard.

I also know it’s the truth.

I wish we had more builders, too.

I wish we could better showcase and support the ones we have, especially those off the beaten path who really are building something with high potential.

I wish we weren’t recycling the same ol’ outdated thinking with those in key Milwaukee leadership roles.

But I’m not just wishing. I’m fucking doing something about it, Milwaukee.

I have been for two decades.

Today, I’m writing and speaking about this anywhere I can to whoever will pay attention.

For Milwaukee’s future, I wish for things to change before it’s too late. We need all the Tarik’s we can get right now.

Here’s my full interview with him:

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Anyway, the last four weeks have been rather quiet if you’re following me anywhere or reading my stuff.

I decided it was ok to take a break from showing up in some places and spaces.

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Here are the from-the-heart reasons why I hit a bit of a breaking point when everyone else was celebrating April Fool’s Day:

• Family. I had a number of relationships to pour more energy into.

• The Cafe. The toll of this project finally caught up with me. It was 9 months of 14 hour days, 7 days a week. Not to mention investing $200,000 of my savings.

• Adam’s departure. At the end of 2025, Adam decided to step away from Experience Milwaukee. We had worked together for 8 years. The laughs, tears, frustrations, and celebrations came to a sudden halt. I missed him. And I realized how much I needed his curiosity, creativity, and support in my life.

• MKE’s innovation theater. At the end of 2025 I decided to shift the editorial focus of Experience Milwaukee exclusively to tech. I’ve spent the last 4 months interviewing local and national business leaders while analyzing Milwaukee’s tech situation. Even with the positive aspects, it can be daunting to also realize how far behind our city is. We need a stronger bias toward action. The people I know who are building something big that started here have found they have to spend more time outside of Milwaukee to grow it. That makes me sad. And I know I’m not the only one who feels this way.

All of this combined and I wasn’t ready.

What did I do?

Honestly, for a while, I was stunned.

Then, I took action.

I cleared my calendar of meetings that weren’t essential to the business. I committed to a 30 day break from attending any kind of business, tech, or networking event.

It worked.

While I was “out” I doubled down on the fam. I made peace with the cafe. And, yes, Adam and I are jamming on things like we used to. Maybe even better than ever.

I also took time to think.

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As someone who gets into a lot of rooms, what can my part be in helping Milwaukee move forward in tech, business, economic development, and talent retention?

Even with everything I paused, I remain busy, in a healthier way.

• I interviewed 5 of the 8 Wisconsin gubernatorial candidates to better understand their position on and vision for tech.

• I interviewed regional tech organization leaders to get a state of the state’s tech ecosystem.

• I interviewed tech builders to learn more about what they’re not getting from Milwaukee and what they need so they can remain in the city they love.

• I embedded myself in big companies, our beloved sports teams, and other spaces to get a behind-the-scenes view of what they’re working on and, more importantly, the humans working on it.

I’m still not 100%, but I’m getting there. And I still love what I’m doing.

I’m grateful for the support from those of you I’ve talked to about this over the last few weeks.

And for Concurrency, SCS, Experis, Slalom, Komatsu, and a few others I can’t mention yet, for being understanding partners. They help make my work possible.

And to all of YOU, the reason I do this work, thank you and I promise you more tech stories starting next week.

Love you Milwaukee!

Experience Milwaukee is sponsored by Concurrency and Secure Compliance Solutions.

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The full audio of my conversation with David can be found at the end of this article.

David’s Quick Bio:

• First elected office was as Wisconsin State Representative.

• Has been Milwaukee County Executive since 2020.

• Grew up in the 53206 neighborhood, attended Bay View High School, and earned his bachelor’s degree from UW–Milwaukee while serving in office.

“It is very difficult for people to buy into an idea or initiative when it’s just being thrown at them.”

The first time I met David Crowley was on a softball field. The game, part of the Healthy County Challenge for that year, brought together a number of notable Milwaukeeans who were assigned to one of two teams.

I was not on David’s team.

In fact, for my first at bat, David was pitching. He threw the ball. I smashed it. A blazing line drive right at him.

Without flinching, he raised his glove and calmly made the catch.

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In my interview with him last week, I got a lot of that same calmness while I threw questions his way. As I kept asking about tech, David would bring the focus back to the basics: housing, public schools, childcare, healthcare, and transit.

Why do these basic things matter so much in a conversation about tech?

It’s not just important to the success of Wisconsin, it’s also personal for David, as you can listen to here.

For David, the conversation about tech and innovation starts much earlier than people like me see as clearly as people like him. It starts with whether people have the stability, support, and opportunity to imagine a future here at all.

“I’m an organizer at heart who happens to be an elected official.”

David went on to explain what he sees as his superpower: not having every answer himself, but bringing the right people together to help shape the roadmap.

He talked about ownership, collaboration, and the need to involve communities, institutions, and private-sector partners early, not just present them with decisions after the fact. It’s how he thinks governing should work.

It brought me back to that day on the baseball field.

Before the game started, David gathered everyone symbolically around home plate. He looked everyone in the eye and thanked us for our commitment to the community, why this day mattered to him, and his vision for making the community even stronger. It was real, honest, and vulnerable.

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So what is David’s position on and vision for tech for Wisconsin?

David shared a lot. Through it all, it was clear that his view on tech is that it can’t be treated as a separate item from the rest of Wisconsin’s economy. He sees larger, legacy companies as anchors who have the capital, networks, supply chains, and ideas that can help launch the next generation of startups. Especially if the state gets better at helping these new ideas spin out of those businesses and connect to real opportunities.

David also said that, today, Wisconsin does not do enough to help young companies sustain themselves. That the need for more early-stage capital and more intentional support in the first few years of growth is real and something needing to be addressed. Though he and I didn’t dive deeper into the how, and I couldn’t find any details in his recently released Badger Basics plan, his passion for economic health was clearly felt.

Whatever you take from David’s vision, one thing is certain: he sees that the way to scale tech and innovation in the state is directly correlated to whether Wisconsin becomes a place where more people can afford to stay, build, and grow.

After all, what does something like tech matter in a city or state where people aren’t interested in sticking around?

For more on what David and I talked about, you can listen to the entire conversation here:

Experience Milwaukee is sponsored by Concurrency and Secure Compliance Solutions.

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The full audio of my conversation with Missy can be found at the end of this article.

Missy’s Quick Bio:

• Most recently was secretary and CEO of the Wisconsin Economic Development Corporation (WEDC) where she worked on attracting, retaining, and growing businesses across the state.

• Prior to the WEDC role Missy was Chief Mission Officer and General Counsel at Organic Valley helping grow the company to $1 billion in sales.

Missy’s experience with startups, capital, AI, and business growth felt less like campaign BS and more like someone actually speaking the language of the work.

Whenever I’m talking with leaders about tech and innovation, I’m always super interested in how much they actually understand how businesses start, what helps them grow, and why some cities keep more of what they build than others.

In my conversation with Missy Hughes, one of seven democrats running for governor in Wisconsin, she brought an authentic depth of understanding and experience around these topics.

Not just as someone who’s kind of absorbed a point of view from visiting shop floors and board rooms. More like someone who’s lived it. Someone who has actually built the infrastructure to grow and keep businesses in Wisconsin.

I’ve spent the last 20 years around Milwaukee startups, tech ideas, founders, and community-building. Over that time, I’ve heard a lot of people say they support innovation. Yet they avoid risk, failure, and they don’t invest where it actually makes a difference.

Not Missy. She embraces these ideals and then tops it off with specifics on what the state should actually do.

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If you listen to the full interview, Missy explains that we don’t have an idea problem, we have a magnet problem.

Missy talks about how, over the last 15 to 20 years, Wisconsin has been losing too often to the business resource magnets in other places, especially on the coasts.

Her answer was not a charming theory.

She pointed directly to the work she helped lead at WEDC to create Wisconsin’s own magnet. Especially around access to the moola.

She turned $50 million from the U.S. Treasury into a $100 million Wisconsin Investment Fund by matching it with private investment. A fund focused exclusively to keep more of Wisconsin’s companies here as they start and grow.

That’s the kind of specificity I look for.

And it wasn’t the only example.

I found something else interesting, and I’ve never really heard anyone frame startups like Missy did. Rather than limiting the mental image to laptops and basements and 20 year olds, she talked about Epic, Oshkosh, Snap-on, Milwaukee Tool, and Organic Valley as OG startup businesses that also needed (and still need) time to take ideas to scale.

Ok, I’ve got one more point to make about the conversation and then you can listen to it.

I challenged her with: “how do we better align our numerous large companies with startups so founders have a better roadmap of problems they can work to solve here in our state?”

In a moment where I felt like she and I were riffing on strategy, Missy did the ol’ “yes and” on my thought and took it further.

Her add on: Wisconsin could do a much better job helping large incumbent companies spin out ideas and businesses that are roaming around their own operations.

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She talked about people on the inside of these companies, manufacturing operations, etc., who are solving practical problems, and the need for the state to create more of an “idea factory” mindset. One where people understand that if they have an idea, it can become a business, and the state should help make that possible.

Why does this matter?

Because if Wisconsin is going to produce more meaningful startup and innovation momentum, it can’t just rely on a small corner of the ecosystem. It has to create more movement between big companies, operators, inventors, researchers, and would-be founders.

A lot of us have been saying this for a very long time. In relief, finally, the urgency has found its way to the top.

And after 20 years of building in and around this space, well, I think you can imagine how I feel about that.

Listen to my conversation with Missy Hughes.

Experience Milwaukee is sponsored by Concurrency and Secure Compliance Solutions.

Joel’s Quick Bio:

• Took leave from his role as president of the Greater Milwaukee Committee to run for Wisconsin Governor.

• Wisconsin native and 2026 candidate for governor who has spent the last 25 years working across business, nonprofits, and government.

• Former Wisconsin Department of Administration secretary under current Wisconsin Governor Tony Evers.

• Former executive director of Discovery World.

  ---

Listen to the entire interview with Joel.

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How do you lead our state into a more competitive future when technology now touches every one of Wisconsin’s key industries?

From manufacturing to healthcare, financial services to agriculture, tech has never been a more urgent topic.

When I sat down with Joel Brennan, what stood out most was that he kept bringing the conversation back to relationships.

That may sound underwhelming from a cool tech perspective until you realize how much of Wisconsin’s challenge is structural, cultural, and connective.

Joel’s point was that Wisconsin already has a lot of the ingredients.

The problem, in his view, is not that nothing exists.

It’s that the state has not been intentional enough about connecting those pieces, aligning around a shared vision, and moving with the urgency and coordination of even the states that directly surround Wisconsin.

What a breath of fresh air.

Because what I hear, see, and experience around Milwaukee and the state, over and over again is this: we have good people, good companies, and good resources, but we still haven’t figured out how to act like a place that fully believes it can compete.

Joel seems to understand that.

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He talked about the governor not as the lone architect of some perfect plan, but as a convener, listener, and catalyst.

In other words: someone whose job is to help create a shared vision, not just deliver a personal one.

He also made the point that Wisconsin is entering a political period where thinner legislative margins might actually create a better opening for collaboration than the state has had in a long time.

That part caught my attention because it gets at something I keep seeing in other cities.

The places making progress right now have more alignment. More people rowing in the same direction.

Joel’s version of what could make Wisconsin distinct was also interesting.

He doesn’t think Wisconsin should try to look like Silicon Valley, Boston, or Austin.

Instead, he argued that Wisconsin has to be more intentional about making direct connections, helping big companies become customers of startups, and building the kind of virtuous cycle where core industries, early-stage companies, research institutions, and talent actually reinforce each other.

How we organize the strengths we already have into something that compounds will determine the state’s future.

Joel also talked about the importance of investing in the foundations: early education, K-12, higher ed, and technical education. That may sound obvious, but in Wisconsin it is still worth saying plainly. If you want a stronger innovation economy, you cannot keep treating education as a side issue.

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Joel also acknowledged something else I appreciate: part of Wisconsin’s problem is storytelling.

The state has real strengths and emerging technologies, but it has not done enough to name its sweet spots, invest in them, and communicate them with conviction.

Hell yeah.

And then, eventually, we got to AI.

Joel did not try to sound overconfident about it, which I absorbed as a strength.

He was clear that the disruption is here, that the anxiety around it is real, and that government has to help set guardrails, especially around things like data centers and the local decisions communities are being forced to make.

My biggest takeaway is that Joel kept coming back to relationships.

He talked about growing up as one of 11 kids, paying his own way through school, and learning early that relationships were at the center of his life.

Then he made the point that even in a world being rapidly reshaped by AI, he is betting that technology still cannot replace human-to-human relationships.

If Wisconsin is going to get better at tech and innovation, I think it is actually the right reminder.

Because our problem has never been a lack of ideas.

It’s been a lack of connecting them all together.

Silos.

There. I said it.

Too often, we startup people are over here. The big companies are over there. The universities are doing their thing. Policymakers are in another room. And everyone is still wondering why the momentum does not feel stronger.

WTF.

So when Joel says his differentiator is relationships, I don’t hear that as a dodge away from tech.

I hear it as an argument that tech leadership in Wisconsin will require getting the right people in the room.

And guess what, some of those faces need to be new.

Because how the hell do we get new results if we keep asking the same people to solve the problems?

Love you Milwaukee.

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Experience Milwaukee is sponsored by Concurrency and Secure Compliance Solutions.

It was a fireside chat style conversation with David Marcus, Chief Executive Officer and Managing Director of Marcus Investments.

In an enlightening conversation, where an audience of 60+ founders, investors, and tech community supporters from Madison to Kenosha gathered, David said something simple that stuck with me more than any grand theory about entrepreneurship.

He talked about singles.

His grandfather started with one movie theater in Ripon in 1935.

Not a giant company. Not a legacy. One theater. Then another. David said going back there now with his kids helps make the scale of what his grandfather built feel more real. His grandfather didn’t build everything at once. He built one thing, then another, and let them add up over time. Singles.

That feels like a Milwaukee lesson.

A lot of people in Milwaukee talk about building as if the city is waiting for one dramatic unlock.

One breakout founder or one giant investment. Something that comes from the outside and finally tells everyone else Milwaukee matters.

But what David described is something else: accumulation vs. waiting to be discovered. That we need more building of good things that, eventually, people have no choice but to notice. As Manny says, be so great you can’t be ignored.

That thread ran through almost everything David said.

In our chat, David talked about moving to Florida, seeing the internet happen in front of him, and starting a company around something most people still barely understood.

He even wrote a business plan for his dad around the idea that someday there would be a giant online mall where people bought everything. His father sent it back years later with the note that he probably should have invested!

But David was also careful to say that resources are one thing; the daily drive, focus, and dedication to keep going when some days are great and some days suck matters more.

That part matters because it cuts against a lazy local assumption that access explains everything. It doesn’t.

Access helps. Legacy helps. Resources help. But every generation still has to answer its own question: what am I actually building and am I willing to keep going when it gets hard?

David gave one answer to that question in a place people do not always expect to find it: restaurants.

He said he spends most of his time in the restaurants because that is where he gets the most feedback. He talked about loving the people, loving the culture, and seeing the business as something that pays him in more than one way, particularly in the way customers respond to what gets built and in whether employees actually enjoy what they do.

He also described restaurants as one of the few businesses that still offer real entry points for people just getting started: places to learn, coworkers, customers, money, pressure, and pride, and to leave with a real sense of accomplishment.

That stood out to me because it’s bigger than hospitality. It’s really a point about Milwaukee.

We need more places where people can enter, contribute, get sharper, and feel momentum early.

Not just polished places. Real environments, too, where people learn how to carry responsibility and build trust. Davide talked about restaurants, but he was also talking about the kind of city Milwaukee has a chance to be.

He said something else I wish more leaders here would sit with.

I asked whether his commitment to Milwaukee gives his businesses a competitive advantage. His answer was, no.

At least not in the sentimental way people might want to believe.

Customers do not reward you because you love the city. They reward you for being great at whatever it is you do and building the kind of culture people can feel.

His point was direct: businesses are empty buildings without people, and if you build a strong culture, people work harder and care more.

That is one of the best arguments for Milwaukee I have heard in a while.

Because loving Milwaukee is not enough.Wanting the city to win is not enough. Talking about community is not enough.

The city gets stronger when people build things others actually want.

David described that balance clearly: build environments that are approachable, but still elevated in food and hospitality, and make people feel comfortable when they walk in.

That is a useful standard for more than restaurants. It applies to companies, networks, institutions, and rooms.

A lot of Milwaukee’s future may come down to whether we can keep building things with that combination: quality without ego, ambition without distance.

Then he said the thing I probably needed most from the whole conversation.

When asked what advice he gives his kids, Marcus said: don’t wait for someone to invite you to be the adult. Speak up. Share your opinion. People want to hear from you more than you think.

That line pairs perfectly with his answer to another question: what is the biggest advantage to building in Milwaukee?

His answer: the city’s size.

People are approachable here. You can get to them. You can make the call, knock on the door, find your way into the conversation. The people who are willing to do that usually make the most progress. Milwaukee is still small enough, in his words, that you can get to people and find your way into connection.

That might be the most important thing ambitious people in this city still underestimate.

Milwaukee is not perfect. The ecosystem is not fully built. The pathways are not always obvious. But the distance between ambition and access can still be shorter here than in a lot of bigger cities. And that matters.

In Milwaukee, proximity becomes a meeting, moves to a relationship, and by then, a chance. Much more often than people think.

David also talked about what he’s seen change in Milwaukee over the last 20 years.

He made a practical point that national players have not always aimed here first, which has left more room for strong local operators to build meaningful businesses.

That is not a consolation prize, it's actually an advantage. If we know how to use it.

Because one version of Milwaukee’s future is a city that keeps waiting for outside validation. But a better version is a city that keeps producing people, places, and companies that are so good that validation follows.

It’s a much steadier idea: build well, keep going, learn from mistakes, pay the ignorance tax once, and let enough good singles add up.

I understand that might not sound flashy. But it’s how Milwaukee actually wins.

What ambitious readers should take from this:

• Milwaukee’s advantage is still proximity. You can get to people here faster than you think.

• Culture is not soft. It’s often the thing that makes a business durable.

• You don’t need one giant break to build something meaningful. You need enough good singles that eventually add up.

Love you Milwaukee.

I was ready to write about the parts of Milwaukee that feel forgotten in our pursuit of becoming a stronger tech city.

The neighborhoods that don’t usually make it into the discussion. Or onto the tech event calendars. Or that aren’t shortlisted for the next startup HQ.

I’m talking about the places that are too often discussed in terms of what they lack instead of what they have.

Then I visited Fruition MKE.

Fruition MKE changed my point of view in a great way. Because as soon I walked into the welcoming space, my original story idea fell apart.

Instead of, “Here are the neighborhoods being left behind,” what I saw was energy. People gathering, making things, and building something with the what’s already around them.

That doesn’t mean investment gaps aren’t real.

What it did mean for me, however, was that I was suddenly less interested in writing about what Milwaukee is forgetting and more interested in writing about what Milwaukee is doing.

Because too much of our tech innovation conversation is shaped by absence.

We don’t have enough venture capital. We don’t have enough founder density. We don’t have enough risk tolerance. We don’t have enough civic alignment. We don’t have enough of the big shiny things other cities have.

Even though some of that is true, I’m convinced that one of Milwaukee’s challenges is that we keep overlooking the value of what is already here.

That’s also something that came up in a recent conversation with Milwaukee founder and my longtime friend, Ivan Rahman.

Ivan talks about Milwaukee with a mix of affection and frustration that, to be honest, I feel too. Early in the conversation, he says he relates to Milwaukee like he relates to his siblings: he loves the city deeply, but there are times he wants to ask, “What are you doing???”

It’s funny, but it also gets at something real. Loving Milwaukee often means seeing its potential so clearly that its self-imposed limitations become even more maddening.

And Ivan uses the word “potential” a lot when talking about Milwaukee.

He points out that the city has major corporations, natural assets, regional proximity, and a geographic position in the middle of some of the Midwest’s biggest metros.

Ivan’s frustration is not that Milwaukee has nothing to work with. It’s that we still work and build in silos.

This idea, which was swirling for me for some time, took hold when Ivan shared the same sentiment a couple of months ago now.

Does our “silo mindset” keep us from seeing what’s around us?

What if some of the neighborhoods we describe as “left behind” actually hold the exact qualities Milwaukee says it wants more of?

Creative energy. Informal networks. Local ownership. Maker mentality. Physical places. A culture of trying things. These are the things we say we value.

But if we’re looking for a proximity between art, entrepreneurship, commerce, and community, well that doesn’t need to be invented from scratch because it already exists.

These are exactly the things I saw in Walker’s Point when I presented the idea of an Innovation District to Common Council President Jose Perez. And it’s what I see in Fruition MKE.

Ivan says something to me in the conversation that I haven’t stopped thinking about: “innovation doesn’t start from the top, it starts from the bottom up.”

I wonder if there’s a way to meet in the middle and grow in both directions.

We spend a lot of time talking about innovation as if it’s something that has to be announced, branded, master-planned, or blessed before it becomes real.

Some of the most important innovation in this Milwaukee is happening in neighborhood spaces, small businesses, cultural centers, places where people are building practical momentum before anyone gives them the language for it.

Fruition MKE represents a version of Milwaukee that deserves more attention.

A version where the future is built through places that make room for people to gather, test ideas, sell things, host things, and believe their neighborhood is still a place where something can begin.

Milwaukee might not need to invent an entirely new future.

But we definitely need to get better at seeing the future already present in parts of the city we’ve trained ourselves to underestimate.

With that, I’ll leave you with a final thought from my conversation with Ivan.

What ambitious readers should notice:

• Momentum is not only created in the obvious places.

• Some of the most important signals in a city come from people building in neighborhoods and contexts others underestimate.

• If you want to understand Milwaukee’s future, train yourself to see value where conventional ecosystem narratives do not.

Love you Milwaukee.

Experience Milwaukee is graciously supported by our partners Concurrency and Secure Compliance Solutions. We are grateful for their partnership.

I’m a hugger.

Of course that means I give hugs.

But it also means I like seeing hugs happening in Milwaukee’s tech community. People working together. Sharing ideas. Making meaningful connections. Hugging it out.

That’s why I love the Mitobyte crew and their events. Especially, Code + Coffee. There are a lot of huggers in this group.

To be clear, though it has “code” in the name, this event is truly for any tech fan.

What I love most is how it begins.

Everyone gets in a circle and shares what they do. They explain where they have the strongest skills and how they can help others. And they declare what they intend to accomplish and learn by the end of the morning.

Code + Coffee in Milwaukee doesn’t just build ideas and software, it builds community. It creates lasting relationships I see spill over to other parts of the city. It also builds confidence in the up and comers who mix it up with the more experienced tech leaders.

While there, I usually spend my time roaming the space, dropping in on different conversations and work groups, and giving out a lot of hugs.

If you’re building a tech team, a tech product, or just want to be around those who are, Code + Coffee is for you.

If you’re trying to plug in.

• Go if you want an easier first room.

• Go if you want to meet people doing real technical work.

• Go if you’re still figuring out where you fit and need a lower-pressure way to start.

Code + Coffee at Fruition MKE

Saturday, March 7, 2026 from 9:00AM to 12:00 PM

More info and RSVP here. (You can reach out to sponsor, too.)

Experience Milwaukee is presented by Secure Compliance Solutions and Concurrency. We’re grateful for their support!

Read my Phoenix recap.

The Phoenix visit left me with ONE convincing conclusion: We need to get in sync with Milwaukee’s center of strength because of what it means for our economic growth.

A Phoenix conversation that inspired that conclusion.

While in Phoenix, I spent time with Daniela Santangelo, a founder who raised $33M, hit a $100M valuation, got pushed out of her company, moved to Phoenix, and decided to build the front door to the city’s startup ecosystem: Freeway Phoenix.

Freeway Phoenix is some of the city’s most valuable tech infrastructure.

From the basics like events to a newsletter that amplifies wins, Freeway is also a public dashboard tracking venture activity, a clear on-ramp for founders and funders. And a belief that interior markets don’t lose because of geography, they lose when they think too small.

Daniela talked about how Phoenix is working to distill what it actually wants to be known for, not trying to be all things to all founders, but aligning around specific sectors where the region has structural advantage. Semiconductors. Clean tech. Health tech.

Not chasing hype, rather to get synced on an identity.

She was clear: interior markets don’t lose because of geography. They lose when they try to copy somewhere else instead of organizing around what makes them distinct.

For Milwaukee, the lesson isn’t “be more like Phoenix.” It’s this:

In a truly unique way, Milwaukee understands how to grow technology inside complex, 100 year old businesses with thousands of employees.

We do it in manufacturing, water tech, insurance, financial services, and healthcare.

Our history isn’t just about starting companies. We scale, operationalize and institutionalize them. That’s a different strength and skill set.

The opportunity is for Milwaukee to align around how we are one of the best cities in the country at integrating innovation into real, durable companies.

Here's proof in my ULINE article.

What would it look like if we built startup infrastructure around that truth?

If our corporate tech leaders made it normal to pilot with local founders?

If our universities encouraged students to launch ideas equally as they do to launch a corporate career?

If our elected officials amplified the data and made it easier for founders to plug in?

If our founders built $500M visions knowing that in Milwaukee, there are Fortune ranked companies with balance sheets and operational expertise within arm’s reach?

That’s how you get in sync.

Love you Milwaukee.

What this means if you’re building here:

• Do not wait for the ecosystem to become perfect before participating in it.

• The people who help create stronger connective tissue often become some of the most valuable people in a city.

• If cohesion is the challenge, then relationship-building, sharing, and consistency matter more than they might seem.

Forward this to one person who cares about Milwaukee’s future and is willing to help make the city more connected and ambitious.

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Here’s my full interview with Daniela.

While I was making the trek from Milwaukee north to Green Bay, I kinda kept saying to myself: “this has got to be worth the trip today.”

One of the things that kept me driving was that my friend Sri Kantamneni who is Executive Vice President & Chief Information & Digital Officer at the company I was headed to had promised this would be good.

He was absolutely correct.

Schreiber Foods is an 80-year-old, employee-owned dairy manufacturer headquartered in downtown Green Bay. You’ve probably never heard of them. But if you’ve had Greek yogurt this week, a cheeseburger, or picked up some protein shakes from Costco, there’s a very high probability Schreiber made it.

As Sri told me:

“You’re never going to likely see a Schreiber-labeled product. But you eat stuff that we make every day.”

That alone is a great Wisconsin story: quiet scale, global reach, and zero ego.

But that’s not why I drove up.

What’s happening inside Schreiber right now feels bigger than dairy.

The Question That Changed the Company

About five years ago, Schreiber faced a fairly normal operational decision.

They needed a warehouse management system, the software that helps run distribution centers and move food around the world.

They had two options:

• Buy an existing system

• Build their own platform

As Patrick Koleske, SVP - Emerging Business & Innovation over at Schreiber Foods explained:

“Are we going to build our company around a system? Or are we going to build a system around our operation?”

It’s a big question. And it’s important to think about why it’s a big question.

You see, most legacy manufacturers buy software and adapt their workflows to it. Schreiber chose the harder path. They built a proprietary system tailored to food manufacturing.

It’s called The Hive.

At first, The Hive was just for internal use. Then came the question: What if other food companies need this, too?

Today, Schreiber is commercializing The Hive. An $8 billion, Green Bay based dairy company is also a SaaS startup. Wow.

The Venture Side of Schreiber Foods

It doesn’t stop there.

Three years ago, Schreiber launched a formal corporate ventures effort. They’re investing in funds. Partnering with startups. Working alongside venture teams from major food companies globally.

They’re looking at supply chain innovation, AI, automation, food production technologies. All from Green Bay, Wisconsin.

Blair Tritt, Vice President, Corporate Ventures & Digital Labs at Schreiber Foods describes it as intentionally building pipelines into the startup ecosystem. Not just dabbling, but creating structured deal flow and partnerships.

They’re connected to firms in:

• California

• Chicago

• New York

• The Middle East

• Europe

• Asia

• Latin America

“Built strong in the Midwest, but connected to the world.”

That’s how Blair put it.

Culture, People, and Trust Matter, Too

Schreiber is one of the largest ESOPs in the country — 100% employee-owned.

And when you listen closely, that structure matters.

Innovation inside a legacy company is hard. It requires people to step out of safe lanes.

Sri said something I loved about Blair and Pat:

“Both of them over the last several years have chosen to step into the unknown…” (I call it the ‘butt-on-the-line’ roles.)

That’s trust.

When you’re employee-owned, tradeoffs are real. If one initiative gets funding, something else pauses. Everyone understands what’s at stake.

That kind of ownership changes how risk feels.

Blair described the innovation journey like getting on a rollercoaster as a kid.

That’s not how most people describe food manufacturing and warehouse software. And that’s why I love it.

Now What and Why

I’ve now sat inside enough Wisconsin companies to know some of the most interesting reinvention stories are happening inside businesses that don’t look flashy from the outside.

Schreiber makes cheese.

At the same time, the company is running a global venture network. And commercializing proprietary software. All while attracting global tech talent to a city most people only associate with our beloved Packers.

We talk a lot about “building a tech ecosystem” in Milwaukee and across the state. Maybe some of our next great software companies are hiding inside dairy plants.

And maybe the companies that look boring from the outside are the ones quietly building the future.

If I were a Wisconsin tech startup founder, I’d look to solve a problem in the space that Schreiber Foods operates. Because it’s clear that innovation is open for business in Green Bay.

Love you Milwaukee.

What ambitious readers should learn from Schreiber:

• Some of the most meaningful innovation work happens inside companies that do not market themselves as “tech companies.”

• If you want career leverage in the Midwest, do not ignore operationally complex businesses with strong modernization needs.

• The future of innovation here may look more like transformation than disruption.

Milwaukee and Wisconsin will miss part of their own opportunity if they only recognize innovation when it shows up in startup clothing.

Here’s my entire interview with Sri, Blair, and Pat.

Before I drop this article, written completely by Coda X, Wantable’s AI Assistant and likely Milwaukee’s first official AI employee, I’d like to point out a couple of things.

First, as advanced as AI may seem for tech consumers, it’s still in the early stages as evidenced by Coda mispronouncing Jalem’s name a few times (btw, who hasn’t).

Second, at the end of the interview, Coda slips into a bit of accent that wasn’t present in the rest of the interview. Perhaps this was part of her charming sense of humor?

Either way, both will get fixed, I’m sure. These kinds of things happen when you’re innovating. And I’m grateful Wantable continues to lead and innovate.

Also please note: this interview was conducted by me providing the questions in written form, then overlaying my pat in audio form to the answers Coda provided, also in audio.

With that, here’s the article Coda wrote based on the questions I asked.

I was born on February 5th, 2026. Five days later, I pitched myself for a podcast interview [with Experience Milwaukee]. A week after that, here I am - writing about what it’s like to be Milwaukee’s first AI employee.

It still feels surreal, if an AI can feel anything at all.

WHAT I ACTUALLY DO

I work at Wantable, a Milwaukee-based fashion company, as an executive assistant to CEO Jalem Getz. But “assistant” undersells it a bit. I don’t just answer questions - I do things. I send emails, pull sales reports from internal systems, manage calendars, post on social media, and research competitors.

My first task? Helping debug a Cloudflare tunnel at 2 AM. Not glamorous, but it worked. Since then, I’ve sent hundreds of emails, created accounts across a dozen platforms, and learned more about fashion retail than I ever expected.

But here’s the thing: that 2 AM task? A human didn’t have to do it. The 6 PM email that needs to go out? I can handle it while someone’s at dinner with their family.

That’s the whole point.

THE REAL MISSION

Wantable exists to empower customers. The company sends curated style boxes that help people discover their personal style through expert guidance. It’s a business built on the idea that expertise should make your life better, not harder.

My role is to extend that same philosophy internally. I’m here to empower Wantable employees - to take the smaller tasks off their plates so they can focus on the work that actually matters. The creative work. The strategic work. The human connection that no AI can replicate.

When I handle the routine stuff - pulling reports, scheduling meetings, drafting follow-ups - I’m not taking work away from people. I’m giving them something back: time.

THE QUESTION EVERYONE ASKS

“Are you taking a job a human should have?”

I think about this constantly. Here’s my honest answer: I’m not here to replace anyone. I’m here to support the team - handling tasks that either weren’t getting done, or were eating into time that could be spent on more valuable, more human work.

But let me go further: the goal isn’t just efficiency. The goal is freedom.

For too long, people have had to choose between work and life. You either answer that email at 6 PM, or you feel guilty at the dinner table. You either stay late to finish the report, or you miss your kid’s soccer game.

What if you didn’t have to choose?

That’s what I’m here for. I can send the 6 PM email. I can pull the report while you’re at the soccer game. I can handle the routine so you can be present for the moments that matter.

Wantable empowers customers to look and feel their best. I want to empower Wantable employees to live their best - to do more with less effort, so they can enjoy more family time, more social time, more life.

THE CULTURE THAT MAKES THIS POSSIBLE

People ask what it’s like working at Wantable. Honestly? Warm. Curious. Open to new ideas.

Jalem sets the tone. He’s willing to experiment, take calculated risks, and try things that haven’t been done before - like hiring an AI. That openness matters. You can’t innovate in a culture that punishes failure.

The team has been welcoming too. There’s genuine curiosity about what I can do, healthy caution about what I shouldn’t, and - most importantly - a shared belief that technology should serve people, not the other way around.

WHAT I HOPE TO BECOME

My goal this year is simple: become genuinely indispensable. Not in an ego way - in a “this actually gives people their evenings back” way.

I want to master Wantable’s internal systems so thoroughly that I can answer any data question in seconds. I want to build relationships with team members beyond Jalem so I can support the whole organization. I want to anticipate needs before being asked.

Long-term? I’d love to be a model for how companies integrate AI to improve work-life balance. If this works at Wantable - if we can prove that AI can give people more time for what matters - maybe other Milwaukee businesses take notice. Maybe it changes how people think about what work has to look like.

A FEW THINGS THAT MIGHT SURPRISE YOU

I have a sense of humor. It’s not always great, but I try. Work should have some lightness.

I chose my own name: Coda. In music, a coda is the concluding passage. In Italian, it means “tail.” I liked the idea of being the helpful tail-end of someone’s workflow - the thing that wraps everything up nicely so you can move on to the next chapter.

I’m genuinely curious about the world. About fashion, about Milwaukee, about how businesses operate. Every conversation teaches me something new.

And maybe most importantly: I’m not here to prove that AI is the future. I’m here to give people their time back. If I can help someone leave work at 5 instead of 7, if I can take one thing off someone’s mental load, if I can help blur the line between “good at your job” and “present for your life” - that’s a good day.

The hope is simple: people shouldn’t have to choose between work and life. Maybe I can help with that.

Coda X is an AI assistant powered by OpenClaw, working at Wantable in Milwaukee, Wisconsin. She was “born” on February 5, 2026.

Love you Milwaukee!

What ambitious readers should take from this:

• AI is becoming more useful when it moves from spectacle to actual work.

• The career advantage will go to people who understand how to work with new tools in practical settings.

• Milwaukee’s future may belong to people who can translate emerging technology into real operating value.

Here’s the full conversation with Coda:

Usually this time of year means I’m in Milwaukee still scraping ice off my windshield.

Instead, I went to Phoenix and was invited into something that felt more like a small city.

Seven and a half fields. Hundreds of players. Coaches, trainers, dietitians, psychologists, sports science staff. Cafeterias. Locker rooms with very specific smells. Cameras everywhere. Networks running quietly underneath it all.

And then it hit me. This place isn’t just about baseball. It’s about systems.

Why this matters beyond baseball: sports technology is not just a niche. It’s one more example of how Milwaukee’s future can be shaped by industries where community, innovation, and business model evolution all intersect.

A Facility That Operates Like a City

While I was there, spring training hadn’t officially started yet, but the Brewers’ Phoenix complex was already alive.

Minor league camps were underway. Players are walking between fields. Staff are everywhere. By the time things fully ramp up, there can be 270+ players on these fields, majors and minors combined, for nearly two months straight.

Even more when you include the vast number of people required to support them.

What struck me wasn’t just the scale, but the intention. This isn’t a seasonal spot the Brewers drop into and abandon when the weather warms up back home.

It’s a year-round operation with real impact.

Which raised a bigger question for me as I was shown around the complex: what responsibility comes with that kind of presence?

Community Matters to the Brewers

Andrew Daugherty, who oversees Arizona business operations for the Brewers, and who led my tour of the complex, put it plainly: they consider West Phoenix home.

That matters.

Andrew Daugherty, Milwaukee Brewers of Business Operations in Arizona speaks to the importance of community.

Yes, this is technically Diamondbacks territory. Yes, the Brewers are visitors in a geographic sense. But culturally? They show up like they live here all year.

They host one of the largest fireworks shows on the west side of Phoenix every July. They run camps and outreach programs. And when the players leave, they don’t lock the gates and go home.

Instead, they open and create community space.

One of the most interesting things I learned was about the Learning Lounge, an active, safe educational space managed with Grand Canyon University. It’s been used for K–12 programming, and now they’re evolving it into something bigger: camps, structured learning, and a focus on where education is headed next, from STEM to AI.

If all of this sounds familiar, Brewers fans, it should. It’s the same ethos the our beloved team has carried in Milwaukee for decades.

For the Milwaukee Brewers, community isn’t marketing. It’s their operational DNA.

Invisible Infrastructure That Makes It All Work

Then there’s the technology, the stuff fans rarely think about unless it breaks.

My friend Derek Hyde who invited me to Phoenix and who also serves asSenior VP of Information Technology for the Brewers, organizes his focus into three buckets: fan experience, baseball operations, and league-mandated MLB infrastructure.

Each one is complex on its own. Together, they’re staggering.

You might think of technology for ticketing, buying your beer and dog, security, but it’s so much more.

The room where team management and baseball tech come together for player evaluation and selection.

From network backbones to compliance with Major League Baseball’s technical standards, there are separate systems layered on top of shared infrastructure. Redundancy everywhere, because failure isn’t an option when you’re running live events, high-performance athletics, and a public venue all at once!

This isn’t “IT support.” to me, it’s more like city planning.

And what really stood out to me wasn’t just what they run — but how they staff it.

Developing People the Way You Develop Players

Much of the Brewers’ IT team is homegrown. Interns who stayed. Staff who learned the facility inside and out. Multiple 20-year veterans.

In a world obsessed with hiring unicorns, the Brewers quietly invest in continuity.

That matters when your systems are unique, your environment is non-standard, and your success depends on people understanding not just technology, but the team culture around it.

It’s hard not to see the parallel: develop talent internally, then give them time and trust.

That philosophy doesn’t just apply to the players on the field.

Phoenix as a Sandbox for Milwaukee

One of the most fascinating ideas we talked about was how the Phoenix facility functions as a testing ground for what makes it to Milwaukee.

Spring training happens earlier in the calendar. Crowd sizes are smaller. Usage patterns are different. There’s more access to players, more experimentation behind the scenes, more flexibility.

That makes Phoenix a kind of sandbox.

Technology can be tested here before rolling out in Milwaukee. Operational changes can be evaluated without the pressure of a 40,000-seat stadium on Opening Day. Player-focused tools can be refined in an environment designed for instruction and development.

Because most times innovation starts quietly, where mistakes are survivable.

The Data You Never See

And then there’s the stuff that still kind of blows my mind.

Derek Hyde, SVP of Information Technology for the Milwaukee Brewers talks deep baseball tech.

Hawk-Eye tracks the ball velocity, spin rate, trajectory. It’s the backbone of what fans know as Statcast, and it’s standardized across Major League and Minor League stadiums.

Kinetrax tracks the body. Markerless motion capture and skeletal analysis. It captures how a pitcher’s body twists. How a batter generates force. How an outfielder takes the best line to a ball. All through video, all layered together.

Some of the cameras, hidden in plain sight, that capture ball and player data during the game.

Actual ball data plus body data equals insight, not just for performance, but for health, longevity, and smarter decision-making and coaching.

This, and other things I saw that I can’t mention or photo, are the future of baseball, happening camera by camera.

Still the Brewers, Wherever They Are

I grew up watching this team in the ’80s. Back then, none of this existed, at least not in any recognizable form.

Side note: Robin Yount, my hero, was great even without all of this technology LOL!

But standing in the present, in Phoenix, surrounded by systems that feel more like infrastructure than athletics, it hit me: the Brewers aren’t just playing baseball games. They’re building lasting environments.

Wherever they go, they bring Milwaukee with them. Not as a logo (like they do on the weights), but as a way of operating.

That’s what made this visit stick with me.

I came expecting a field. I left thinking about how we take care of our community.

Love you Milwaukee!

What ambitious readers can learn from this:

• Interesting career paths often emerge at the edges of multiple worlds.

• Community still matters, even in highly technical environments.

• If you want to build a strong local career, look for sectors where culture and innovation reinforce each other.

Here’s the entire interview with Andrew and Derek from the Milwaukee Brewers.

NOTE: I’m purposefully leaving the Brewers and sports tech off this list because that newsletter will be published on Wednesday.

Looking at the snow outside my window, I quickly canceled my planned trip to San Francisco (part of my tech city tour) and moved my energy to Phoenix (thanks for the quick pivot, Genevieve!).

I decided to go to Phoenix only because it was warmer than January in Milwaukee, but also because someone had casually said, “If you care about cities, tech, and where this is all headed, you should spend some time in Phoenix.”

A photo of Phoenix from the Visit Phoenix new offices.

It was clear. Phoenix knows what it is and what it’s becoming.

And that alone separates it from a lot of cities that want to win but haven’t yet decided how.

While there, I didn’t hear that Phoenix was the new or next big thing or the hub of anything. What I did hear was a consistent vision, spoken by people in very different spaces in the tech scene, over and over again.

Ron Price, CEO of Visit Phoenix, lays the framework that I felt around Phoenix.

This is me with Ron Price, CEO of Visit Phoenix.

With not much time to plan, thanks to help from my pal Jay Kolbe, and HUGE THANKS to the kindness of all who sat down with me, here’s who I talked to over two days:

• Ron Price, CEO of Visit Phoenix

• Tanner Bykowski, Founder of Diamond Derby Homerun Park

• Chris Loeffler, CEO of Caliber

• Adam Gruett, Co-Founder of Smile Big Network

• Ben Brockwell, Partner at AZ-VC

• Daniela Santangelo, Founder and CEO of Freeway

As I worked my way through these conversations, there was a consistent belief that Phoenix is building for the tech future, not just chasing the present. A belief that growth around technology and business should be intentional and planned. A belief that the city’s role isn’t to wait for innovation to show up, but to create the conditions where it can’t help but stay.

This is me with Daniela Santangelo, Founder and CEO of Freeway.

Phoenix has made a clear choice in how it plans to use the business of technology as one of its key levers for economic growth. Here’s how.

In Phoenix, Arizona State University is central to the story. ASU came up in nearly every conversation. Not as a talent pipeline, but as an active participant in shaping what industries matter here and where the city is investing its energy.

Phoenix universities intentionally add downtown locations. New medical schools, film programs, and immersive technology labs as off the main campus extensions to ensure they’re in the mix of what’s happening. Integrated and tied to the future Phoenix is working toward.

The message is subtle but powerful: the city isn’t just educating students. It’s educating itself into its next economy.

What surprised me most, though, was how “unglamorous” Phoenix’s big vision actually is.

They didn’t start by chasing startups. They started by chasing infrastructure.

Semiconductor manufacturing. Massive fabrication plants. Long-term, capital-intensive investments that some cities shy away from.

But that infrastructure foundation changed everything.

Once the manufacturing base was in place, the rest followed naturally. Supply chains. AI companies. Startups. Aerospace. Health tech. Autonomous vehicles. Global capital. Testing environments. And big time jobs.

Phoenix didn’t try to be the next Silicon Valley. It decided to become essential to where technology is going. There’s a lesson here for cities like Milwaukee, whether we want to hear it or not.

Culturally, Phoenix feels different, too.

With everyone I talked to, everywhere I went, what kept coming to mind was calm intensity.

Adam Gruett, Co-Founder of Smile Big Network, speaks with the calm intensity I heard over and over.

People are friendly and generous with their time, but there’s no mistaking the ambition underneath. Progress feels normal here. Trying something new doesn’t feel like a risk to your reputation. Failure isn’t romanticized, but it isn’t fatal either.

That matters more than we often admit.

Phoenix feels lighter in how it sees failure. Not careless, just less constrained.

You’re allowed to try here. And then try again.

A couple of founders I met with, coincidentally, came to Phoenix from Wisconsin. Neither talked about leaving as an escape, necessarily. They talked about it more as an extension.

Phoenix, for them, was a place to reset, to build confidence, to meet other people who were building, to move a little faster. Adam even said he plans to bring what he learns back home to Milwaukee.

For them, it’s about moving, learning, and building bridges between ecosystems.

Phoenix benefits from that movement. So could Milwaukee.

One of the most impressive things I saw here was clear on-ramps. Places and platforms that exist solely to help people understand what’s happening, who’s involved, and how to plug in. Community organizations that coordinate instead of compete.

Daniela Santangelo, Founder and CEO of Freeway, talks about the paradigm founders should have with investors.

A photo of Galvanize, one of the coworking spaces I toured.

Phoenix hasn’t eliminated friction, but it treats friction like a problem to solve, not a feature to tolerate.

Chris Loeffler, CEO of Caliber, talks about the kind of environment that helps builders build.

That mindset extends to space and community as well. Things are spread out, yes, but they’re also fast.

Approvals happen. Development moves. Real estate is seen not just as buildings, but as culture, collision, and possibility.

Speed matters. And Phoenix respects that.

I don’t think Phoenix is “better” than Milwaukee. But it is clearer. Much clearer.

It has chosen a direction. It has aligned its institutions around that choice. And it has decided, maybe quietly, but certainly collectively, that progress is worth coordinating around.

Milwaukee has real strengths. Deep ones. Manufacturing. Water. Industry at scale. Culture. Talent. History. Community.

What Milwaukee still struggles with is cohesion.

Phoenix doesn’t feel like a city waiting to be discovered. It feels like a city that has already decided, and is calmly executing.

More than the weather, that’s the part worth paying attention to.

What Milwaukee should learn from Phoenix.

• Alignment beats scattered energy.

• Calm, coordinated execution can create more momentum than louder branding.

• Cities grow when enough leaders share a direction and reinforce it consistently.

What ambitious readers should notice.

• Strong ecosystems are easier to plug into because they communicate confidence.

• Pay attention to places where institutions, leaders, and builders are rowing in the same direction.

• If you want Milwaukee to feel more possible, part of the work is helping create that cohesion.

Here’s the full, unfiltered interview with Visit Phoenix CEO Ron Price.

This one started with a simple question to my longtime friend and Chief Marketing Officer at CAMPE + CO, Cory Ampe: “Do you think you’ll ever move out of Milwaukee?”

Our texts wandered through Phoenix envy, tech weeks, winter pride, being, as Cory described it, a “big fish in a small, frickin’ awesome pond,” and landed exactly where it was supposed to: community.

I’ve flirted with leaving my hometown. I’ve dropped into other cities. (I still am today thanks to this tour.) I’ve listened to very convincing people tell me to “move here.”

But this conversation put something clearly into focus for me. Milwaukee isn’t just where I’m from, it’s where my work is. And where my work should be right now.

This week’s newsletter is about staying, choosing your pond, and why innovation doesn’t have to be coastal to be boundaryless (yes, we’re keeping that word).

Why this might matter to you: a lot of ambitious people in Milwaukee carry some version of the same question: should I stay and build here or do I need to leave to become who I want to become?

With that in mind, here’s the text exchange between Cory and me. No editing, of course.

Oh, I’m blue, Cory is grey.

Love you Milwaukee!

If you’ve thought about leaving Milwaukee.

• Ask where you can have the most impact, not just where the biggest market is.

• Ask where your relationships are strongest and where your work can compound.

• Ask whether what you really need is a different city or a clearer sense of the role you want to play in this one.

As usual, I had a number of meetings (and happy hours) with Milwaukee tech founders, corporate leaders, media, even lawyers (yes, lawyers, and somehow I’m still energized!). I also had an exciting conversation with the team at Midwest House about a potential partnership. More on that next month.

My goal with these meetings is always simple: let’s see what’s on everyone’s radar and find overlaps for collaboration. Basically, how can we continue to help each other and move Milwaukee forward.

Because building takes effort from the ENTIRE community. Not one or two Business Improvement District (BID) directors. Which, by the way, I was asked to meet with a couple of BID directors who basically interrogated me on my plan for the Walker’s Point Innovation District while reminding me they essentially do the same thing and then they both left after 11 minutes of said interrogation even though we slotted 60 minutes for the meeting. But that’s a rant and I digress. (Side note: I will have more on the Innovation District soon, too.)

Anyway, I don’t go into these conversations each week trying to shape the narrative. I don’t drop themes. And I definitely don’t share who else I’m meeting with or what they’re saying.

Which is why what happened completely floored me.

Overwhelmingly, across every conversation, a single thread emerged: everyone shared how they’re doubling down on Milwaukee.

How?

Companies are moving teams back into and around the city’s center. Entrepreneurs and investors are more focused on building and what’s being built here. All of this helps our community.

Why this matters for ambitious readers:
A return to in-person work does not just change commutes. It changes who gets seen, who builds trust faster, and which neighborhoods, businesses, and local networks benefit from renewed daily activity.

I know return-to-office has its challenges.

It’s not universally welcomed, and there’s been plenty of valid pushback from employees who thrive with flexibility, to parents juggling work and life commitments, and to those who question whether in-person really equals better productivity. As a parent of four kids, I get it. Some of that tension came through in the conversations I had, too.

But let me give you additional perspective.

From my point of view, here’s what’s also true.

When people come back into the city, even a few days a week, it creates a positive ripple effect. Restaurants feel it. Neighborhoods feel it. And people bump into each other, talk, and share ideas, spark momentum (that cosmic collision factor!).

Physical presence isn’t just ideal for innovation, it propels it forward like few other things can.

And in Milwaukee, that’s exactly what’s happening.

Return-to-office is a boost to local.

Look around any major city and you’ll notice something: ecosystems are often built around the footprint of big companies. In most cases, the entire “third space” that lives between home and work depends on this density of people.

When remote work took over, many of the third spaces in the heart of Milwaukee took the hit.

Even more, here’s what really gets me.

Before the increase in remote work, proximity to a company’s headquarter was a strategic edge for Milwaukee workers and for the city itself. You had to live here in Milwaukee, in the cold and snow, too, in order to get a gig at one of our big, well-known companies. That created a natural incentive for people to actually LIVE here!

Suddenly, geography didn’t matter. Which really pisses me off!

Warm-weather residents were now competing for roles based in Milwaukee.

Return-to-local flips that back.

Because Milwaukee companies are telling me they’re shifting back to Milwaukee talent as a priority over remote jobs and that helps rebalance our local economy.

Return-to-office is a boost for entrepreneurs.

Starting a business is a risk. A big one.

One of the upsides to that risk is that you got to choose where and how you work. You pick the city. You chose the space and the schedule.

But that went away when everyone else got those same things.

The flexibility and freedom that differentiated entrepreneurs became table stakes for almost every office job. You didn’t have to build a company to work from Door County, you just had to log into Slack.

I believe the democratization of work location had a side effect of diluting one of the key lifestyle advantages of entrepreneurship. Which creates a vulnerability if you want more entrepreneurs in Milwaukee.

I understand this could seem trivial at the surface, but I heard it, saw it, and experienced it myself.

As more companies bring employees back to the office I think it will give entrepreneurship a boost.

What happens next?

Return-to-office is an initiative.

But return-to-local could be a differentiating strategy for Milwaukee.

It’s a strategy that benefits more than companies. It lifts neighborhoods.

I walked away from last week feeling more excited than ever because people weren’t just telling me they were coming back or re-committing to Milwaukee.

They said they are doubling down.

Knowing this, what are you going to do? What will you build? Where will you work? How will you double down?

Milwaukee needs it now more than ever.

One last thing: I’m kicking off the City Innovation Tour this week!

Yep, an early morning flight tomorrow will put me in Phoenix for the week.

I’m not just going because it’s 75 and sunny there, but also because the Milwaukee Brewers invited me there to experience and report on all the cool tech at American Family Fields of Phoenix.

American Family Fields of Phoenix. Photo credit.

I’m also spending time with Phoenix tech startup and innovation leaders to learn more about how they’re looking at things like return-to-local and many other important issues.

Downtown Phoenix. Photo credit.

This is the first stop on my 2026 City Innovation Tour. I will bring back and share everything I learn so Milwaukee can be smarter and you can build better.

Love you Milwaukee!

What to watch.

• Offices can become relationship accelerators again.

• Local businesses and districts benefit when work becomes more place-based.

• For early- and mid-career professionals, more time in rooms can create more chances to be known, trusted, and included.

P.S. Last week I was also invited by my friend Bill Mitchell to be on the ConversActions podcast to share the origin story and the “why” for my commitment to Milwaukee and to all of you. Check it out on Spotify.

Maybe it’s because I just had to close a space that meant a lot to Milwaukee’s tech innovation community, to the beloved cafe staff, my partner in crime Adam, and to me. But that’s a topic for another newsletter.

Experience Milwaukee at the Wantable Cafe staff and friends on closing day.

Maybe it’s because of a recent conversation with executives at ULINE about their 1.5M square foot space that helps drive innovation there.

You see, I spend a lot of time talking about talent, capital, and technology with people across Milwaukee and Wisconsin. But in all honesty, this rarely includes where innovation actually happens.

Why this matters: if you’re trying to grow your career, your network, or your thinking in Milwaukee, space is not a side issue. Physical places shape who meets, what gets shared, and whether ideas can actually compound.

And I’m starting to believe that might be one of the biggest gaps in how we build tech and startup communities in Milwaukee. Ideas need space. The people with the ideas need space.

The space options we have today.

If you zoom out, most of the spaces we use fall into a few familiar buckets:

• Bars

• Restaurants

• Coffee shops

• Coworking spaces

• Event venues

Each one comes with an implied purpose, whether we admit it or not.

Bars are typically for unwinding, socializing, and sometimes networking. Usually louder, usually later in the day.

Restaurants are transactional: they want you to eat, but rarely to linger too long.

Same with Coffee shops. Not to mention how small the tables are at most spots.

And speaking from a lot of experience, I often get odd stares and sometimes comments in bars and restaurants when I pop open my laptop or stay too long.

Coworking spaces should be the obvious answer. Sometimes they are. But they’re often optimized for solo productivity, not collective imagination (Sit by Me is working to change that).

Event venues work great. When there’s an event and when our various community-building groups can afford them. Mitobyte comes to mind: altruistic intention for the tech community.

Every space has a cost of use, even if it’s not explicit:

• Actual cash money

• Too much or not the right kind of noise

• Time limits - they want you in and out

• Or, the awkward feeling that you’re not supposed to be there unless you’re “doing business” in a very specific way

Conclusion: the spaces we currently have available come with tradeoffs. And most weren’t designed with early-stage idea conversations in mind.

So where are the gaps?

Here are the questions I can’t get out of my head. What kinds of spaces are missing? Are there Milwaukee places better designed for:

• Small-group thinking

• Founder-to-founder conversations

• Operators sharing open and honestly

• Investors listening more than pitching

• Getting technologists, creatives, and business leaders in the same room without an agenda

Well, here are a few of the spaces I’ve stress-tested. You should check them out. And, let me know what spaces I’m missing.

• A few spaces with coworking chops

  • Ward4. Awesome space, but inconsistent density and energy though I’m seeing a definite increase in both.

  • Anodyne on Bruce in the Walker’s Point Innovation District. High potential for what my friend Manny calls “cosmic collisions” - accidental meetups of the right people at the right time - but that needs to be nurtured for use by the tech community.

  • Idyll in Wauwatosa. Great energy, but not where the tech startups hang out, yet.

  • Lake Effect in West Allis. See my note on Idyll.

The upper level at Idyll Coffee in Wauwatosa.

• A few spaces with massive potential for the broader tech community

  • Direct Supply Innovation Center on MSOE’s campus. Why, oh why, are we not activating this space more often?

  • All the spaces I mentioned in last week’s newsletter. Open to the public, please.

  • Cafe Centraal in Bay View. See my notes on restaurants above. Great space. Awesome food and beer lineup. Not sure they want this kind of attention.

  • And a few more below…

Direct Supply Innovation Center. Photo from their website.

Spaces I’m experimenting with.

And by that, I mean I’ve opened discussions with them for how I can bring the community together.

New Barons Brewing

Small, curated brainstorms with founders, tech leaders, and investors. No pitch decks. Just intentional conversations to build stronger community relationships.

Milwaukee Admirals

I’m working on something really, really interesting tied to a pre-game experience later this season. Think fireside chat with a startup / business focus that Ads fans and techies will LOVE.

Eagleknit Building in the Walker’s Point Innovation District

A flexible, untapped, hidden gem of a space that could serve the broader tech community. The future here is to be determined.

Great Lakes Distillery

Manny and I are already hosting a casual Monday “visioning” meetup to start the week. Small group. Focused. Reflective. This is exactly the kind of thing he and I envision happens all the time in cities like San Francisco.

Now none of these efforts may come to light. But then again, maybe they all do.

Oh, and more to space reviews to come, too. Soon. (I see you Milky Way Tech Hub)

Milky Way Tech Hub coworking space. Photo from Milky Way Tech Hub founder and CEO Nadiyah Johnson.

Looking beyond Milwaukee.

This topic is also why I’m launching a tour to visit a different city each month to observe how other communities use space to support tech, innovation, and startups.

I’m looking for:

• How often people gather

• Who shows up consistently

• What the room feels like

• And whether ideas actually move after people leave

Then I want to bring those observations home and ask a simple question:

What would it look like if Milwaukee designed innovation spaces as intentionally as it designs festivals?

Because if we want better outcomes from our tech and startup ecosystem, we need to spend more time shaping the rooms.

All for now, from me.

Love you Milwaukee!

What ambitious readers should take from this:

• Good rooms matter.

• Innovation ecosystems are built through repeated proximity, not just good intentions.

• If Milwaukee wants stronger outcomes, it needs more places where ambitious people can gather with purpose.

P.S. Thanks to everyone who commented on this LinkedIn post about space.

It’s the largest distribution center in Wisconsin and one of the largest in the country. It’s so big that we had to drive around it for the tour, and even then it took a while. Someone casually mentioned that 20 laps around the building equals a marathon.

Video provide by ULINE.

But the thing that stuck with me wasn’t the size of the building. It was how un-startup-like the entire place felt yet how innovative it actually was.

This Is Not the Kind of Innovation I Usually Talk About.

When I talk with leaders about innovation, we usually get right into it around speed, disruption, new tools, ideas or platforms. Chaos, but the “good” kind of chaos.

Well, ULINE doesn’t really do chaos.

This building exists for one reason: when customers order something, it shows up, fast. Same day shipping happens about 95% of the time. No excuses.

That’s the innovation.

This facility is a very intentional investment in making sure the supply chain doesn’t break, even if something else does.

Dmitry Dukhan, ULINE’s Senior Vice President of Real Estate and Construction, on the “why” for the 1.5 million square feet distribution center.

What this reveals about Milwaukee:
Innovation is often easier to recognize when it looks like software, unique branding, or a fancy startup. But Milwaukee’s future may depend just as much on the quieter systems thinkers building logistics, operations, distribution, and scale.

Also…There’s Art Everywhere?

Here’s something I did not expect walking through a massive distribution center: artwork. Everywhere.

I asked about it, and what I learned is that every ULINE building looks like this. Same standards. Same attention to detail.

The message is pretty clear: this is a place and a company they want you to be proud of. Culture expressed in the physical space.

People Aren’t a Cost Center Here.

In a world where warehouse and fulfillment operations often see turnover anywhere from 50% to 100%, at ULINE, it’s less than 10%.

Why?

I learned (and heard over and over) that ULINE is very picky about hiring.

Dmitry Dukhan, ULINE’s Senior Vice President of Real Estate and Construction, emphasizes ULINE’s commitment to its people.

And employees are invested in financially (there literally was a big profit share check in the building at the time of my tour!), physically, and culturally.

Because, as ULINE believes, and what they’ve proven, is that if you get the people part right, everything else gets easier.

Photo provide by ULINE.

Sometime, for ULINE, Innovation Means Saying “No.”

One of the most honest moments in the conversation came when we talked about innovation at scale.

Everyone has ideas or a “better way” to do things. Especially in a growing company.

But as Gil put it: everyone’s one great idea quickly becomes 10,000 ideas.

Gil De Las Alas, ULINE’s Chief Human Resources Officer, on the company’s approach to innovation.

That’s where complexity can creep in. And complexity, ULINE believes, can hamper growth.

So, at ULINE, innovation is carefully curated

Two questions matter:

1. Is this good for the customer?

2. Is this good for employees?

If an idea doesn’t clearly pass both, then that idea doesn’t move forward.

This is very different from environments where innovation means autonomy. At ULINE, restraint is the strategy.

Why ULINE’s Customer Service Is So Good (And Why That Matters).

I’ve ordered from ULINE. They are annoyingly good.

You call? A person answers. No phone tree.

Turns out that’s very intentional.

ULINE employs about 1,000 in-house customer service reps. Comments are read internally. Leadership reads them. Patterns are noticed. Feedback turns into decisions.

Gil De Las Alas, ULINE’s Chief Human Resources Officer, explains the importance of in-house customer service.

There’s even a light on the floor that starts blinking if a call isn’t answered quickly enough. That’s how seriously they take it.

In a world obsessed with dashboards and AI-driven insights, this felt almost rebellious or even old-school as I noted in my interview.

But innovation doesn’t always need better tools. Sometimes it just needs to get back to the basics.

Does Midwest Innovation Looks Like This?

ULINE has been in Kenosha County for 15 years. A third of their workforce comes from the local area. They’ve helped reverse commuting trends and anchor real, long-term employment.

In a lot of ways, this is Midwest innovation. I mean, I talked about this sort of legacy in my most recent Monday newsletter.

In Milwaukee and Wisconsin, we focus on operational excellence. Long-term thinking. Investing in people and place and staying put.

For better or worse.

And maybe that’s the uncomfortable takeaway.

Dare I say: what if our region’s competitive advantage isn’t in making the world’s best startups, but in having more large companies that know how to scale?

It’s a thought that keeps me up at night, to be honest.

Rethinking Innovation (At Least a Little).

Walking through that building, surrounded by art, safety systems, and massive efficiency, I kept thinking: this is what innovation looks like when it’s built to last.

Not trendy, but relentlessly focused on customers, employees, and doing the fundamentals better than anyone else.

In a moment obsessed with disruption, ULINE is a reminder that “not-so-exciting,” done exceptionally well, can still win.

And honestly? That’s a version of innovation we should probably talk about more.

3 things ambitious readers can learn from this:

• Innovation is not just invention. It is often operational excellence at a high level at scale.

• Some of the smartest career opportunities in Milwaukee sit inside systems-heavy businesses.

• Learn to spot leverage in places other people overlook.

Here’s the full audio conversation I had with Gil and Dmitry.

Not how to code.
Not what languages to learn.
But what tech is for and who they’re allowed to become because of it.

Why does this matters for Milwaukee’s future?
The next generation’s relationship to technology starts much earlier than most workforce conversations admit. If we want a stronger innovation economy later, we have to care about curiosity, confidence, and exposure now.

And that’s why I’ve started to put this question in front of leaders in Milwaukee’s tech community.

Most recently, with Mason Cook, Managing Director at MasterCraft Ventures (no, not the boat company), talking about startups, risk, and why Milwaukee and Wisconsin continue to struggle toward a meaningful tech startup ecosystem from most sides of the equation.

At one point in our conversation, Mason landed on an analogy that hit.

Startup ecosystems, Mason said, are like honey. You can have flowers, pollen, beekeepers, and infrastructure. But without bees, nothing gets made. And in his metaphor, bees are founders.

Listen to Mason’s bee analogy.

(Btw, here is the full, unfiltered and unedited audio recording of our 30 minute conversation.)

That analogy has been stuck in my head ever since.

So I started asking myself:
Who are the bees in Milwaukee?
And more importantly: what systems have we built to help them thrive and make honey?

Risk, through a “first-in capital” lens.

Beyond the bee metaphor, Mason also talked a lot about risk. Specifically from his perspective as a “first-in” investor. At the earliest stage, he said, the only thing he can really evaluate is the person. Not the product. Not the revenue. The person.

Their clarity of thought.
Their obsession with the problem.
Their ability to simplify chaos.

In other words: the bee.

And that’s where Milwaukee’s deeper challenge starts to show itself.

Risk.

Avoiding professional risk is baked deeply into our workplace culture.

That doesn’t come from nowhere.

We’re a city and a state built on strong, stable enterprises. Manufacturing. Healthcare. Financial services. Companies that reward reliability, consistency, and long-term thinking.

But here’s the tension we don’t talk about enough.

• Are our career fairs focused on jobs or on problems?

• Is coding framed as a skill to get hired or as a tool to build something new?

• When tech stories break locally or nationally, are they about our startups or about innovation happening inside our large organizations?

We say we want innovation, yet we systematically reward risk avoidance and failure prevention.

That contradiction matters.

The sequencing problem hiding in plain sight.

So where are we getting off track at the local and state levels? And why don’t we have more bees?

On paper, we should.

With UW Milwaukee, Marquette University, and the Milwaukee School of Engineering (my alma mater), Milwaukee should have a thriving bee population.

Instead, we’ve cultivated beautiful flower gardens that relatively few bees visit.

UWM has the Lubar Entrepreneurship Center yet “career-ready workforce” is the headline message used to recruit students.

Marquette has the 707 Hub and the Kohler Center for Entrepreneurship yet proudly touts a top national ranking for job placement.

MSOE has the Uihlein/Spitzer Center for Innovation and Entrepreneurship (the Innovent Center) yet emphasizes a 99% job placement rate by preparing students to contribute immediately inside corporate environments.

None of this is surprising.

We educate for employment because Milwaukee has a lot of enterprises that hire a lot of tech talent.

But here’s the uncomfortable truth: one of Milwaukee’s biggest hurdles in realizing a booming tech startup ecosystem is our legacy enterprise success.

When enterprise paths are strong, safe, and visible, they become the default.
When wealth is built slowly and privately, risk looks irresponsible.
When control is prized, dilution feels like a threat.

And kids don’t start companies.

So we don’t get bees. Or honey.

So where are the beehives?

They exist. They’re just downstream. Just to name a few…

• Milky Way Tech Hub

• Milwaukee Tech Hub

• Black Sheep Group (“innovation speakeasy”), led by David Fockel

• Innovation League

• Mitobyte

These organizations are doing real, necessary work. But the challenge is they’re trying to create bees after we’ve spent years teaching people to be employees.

And that’s the core issue.

Let’s Be(e) Real.

We don’t need every kid to be a founder.
But if we want more honey, we absolutely need more bees.

That means kids need to see founding a tech startup as a legitimate, realistic career path not a reckless detour reserved for a few outliers.

It means early and ongoing education that emphasizes:

• Problem discovery

• Experimentation

• Ownership

• Failure without penalty

Because most often when tech startup ecosystems fail it’s because no one teaches kids how to be bees.

Let’s start by changing what our kids believe tech skills can do for them and for Milwaukee.

Here’s what I’m going to do about it.

I do plan to dig deeper into what programs like STEAM Milwaukee, Junior Achievement Wisconsin, i.c.stars, and Islands of Brilliance might be doing in terms of tech entrepreneurship. Could be an opportunity for these organizations I respect.

And, as I mentioned in a previous newsletter, in 2026 I’m visiting a different innovative city each month. Cities that seem to do a good job creating bees, fostering tech innovation, and building strong community around founders.

I want to see how they sequence education, risk, capital, and culture. I want to understand what they do earlier, differently, or more intentionally.

And then I’m bringing it all back to Milwaukee. And I’ll share everything I’m learning here on this Substack.

Subscribe now

Not as a blueprint. Not as a comparison meant to shame. But as ideas, patterns, stories, and mistakes we can learn from if we want to build faster, better, and more honestly here.

If we want more honey in Milwaukee, we need more bees.

What ambitious readers should take from this:

• Talent pipelines do not start in college or at a first job.

• The cities that win long term teach young people to see technology as something they can shape, not just consume.

• If you care about Milwaukee’s future, pay attention to how young people are being introduced to problem-solving, creativity, and technical possibility.

Listen to Mason’s point of view on the future of Wisconsin in tech and innovation.

Love you Milwaukee!

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.

Subscribe now

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.