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Is it possible to make cybersecurity fun and engaging?

I sat down for an interview Reshad Alam and Corey Sodes. And I think both would answer the above, in chorus, with a loud YES!

Reshad is VP & Chief Information Security Officer (CISO) at Regal Rexnord. Corey is the CTO and co-founder of Secure Compliance Solutions (SCS).

Both carry an unmatched passion for their work.

And I mean it. Here’s Reshad in action.

Reshad regularly performs like this for the town halls hosted within Regal Rexnord, a Fortune 1000 company.

And If you you don’t think these songs have impact, just ask anyone who’s watched (now you, too) to recite a few lyrics.

You may not remember the PowerPoint slide that came with it. But you’ll begin to sing along. Including long after the performance. I’ve seen it happen.

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Cybersecurity has been the boring but important topic inside every company for years.

And that really was the point of my conversation with Reshad and Corey.

Because, with the rise of AI, cybersecurity has become more important than ever. And these are two guys who have figured out how to make people pay attention.

While Reshad makes cybersecurity memorable, Corey makes it visible. His sweet spot is the unique perspective and insight he brings from consulting with dozens of SCS clients and industries. He’s able to guide leaders through the cybersecurity maze with lessons from what he’s seeing across the gamut.

All in real time.

What will you get from listening to this interview?

Corey and Reshad riffed on a number of topics…

• AI isn’t exposing your data. It’s exposing how much of it is already in the hands of your employees.

• Don’t block. Redirect.

• Innovate with purpose.

• HR is not giving you a free t-shirt.

• How continuous learning is critical to landing a cybersecurity job.

Want the details?

Take a listen to the full conversation below or on Spotify.

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For this article, I interviewed Michael Regione, VP of sales and marketing at Digital Bridge.

• Digital Bridge was founded by Jeff Hanson who started refurbishing laptops from the campus of the Milwaukee School of Engineering (MSOE).

• Michael was in software startups and healthcare technology leading up to him joining Digital Bridge.

• He now leads the growth of Digital Bridge, including programs that keep electronics out of landfills by getting them into the hands of people who truly need them.

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You never know what you’re going to get when you enter a Walker’s Point warehouse.

As you might expect, I’ve toured my fair share of old warehouse buildings throughout Milwaukee.

In most, I cross my fingers and clench my cell phone, hoping not to get trapped somewhere in the building. Also, that nothing collapses on me unexpectedly.

This day, as I approached the HQ of Digital Bridge on 2nd street, sort of between Walker’s Point and the Third Ward, I nervously wondered what was in store for me.

However, rather than cringy corners and dangerous maneuvers, I stepped into an organized, safe, clean space filled with tech gear donated by those hoping for a second life for their laptops, televisions, phones, and more.

Oh, and I was greeted with enthusiastic, smiling faces from the Digital Bridge team, now totaling about 20 employees.

What started as a dream at MSOE now has real-world impact. Especially with those who need tech the most.

After a walk up the stairs, I settled in to chat with Michael. Within minutes, I forgot I was there to learn more about e-waste.

Because we ended up talking about people.

There was the guy in Connecticut who saw Michael on the Weather Channel and reached out to ship his Macs to Milwaukee. There was the community near Madison that filled a 20-foot truck with TVs, camcorders, old video games.

But the one that almost made me tear up was when Michael mentioned the woman who applied to and landed her first job on a laptop donated by Digital Bridge.

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That’s the thing about Digital Bridge. It’s not just an organization that recycles e-waste. It’s an organization putting tens of thousands of laptops to those who need tech the most. And it’s an organization that finally gives us permission to let go of what’s been sitting in our basements.

Which is why I’m so pumped to launch this partnership.

So welcome to the first of an ongoing series: Recycled by Digital Bridge. Because, like your old laptop, good stories deserve a second life, too.

Don’t stop here, listen to my full interview with Michael below or on Spotify.

And if you have an old laptop, well now you know where to send it:

https://www.digitalbridge.ngo

Love you, Milwaukee!

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1. There’s a rush on storytelling.

In July I wrote about the Executive AInxiety nobody’s talking about.

In that article, I talk about how we need more trust. And more spaces to leverage trust to have honest, compassionate conversations about what we don’t know.

Then, help each other figure it out.

What happened after I published that piece? Organizations started coming to me.

Of the fifteen to twenty firms I’ve talked to over the last few weeks, each has had their version of the same statement: we need help telling our tech story.

Here’s why that’s interesting to me. Just a few years ago, there weren’t many legacy Milwaukee companies who wanted to talk publicly solely about tech.

Today, the people doing serious tech work here want the world to know about it.

(btw, if you want your tech story told: steve@experiencemilwaukeepodcast.com)

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2. The worry within every conversation: talent.

You heard this in my conversation with the CEO who represents 3,800 Wisconsin businesses. It’s not technology keeping manufacturers up at night. It’s people.

I felt that everywhere this month. Not just in a couple conversations, but in more than two dozen meetups, meetings, and events around the city.

How does this all connect? The storytelling rush and the talent worry are the same story.

Every company that begins to tell its tech story makes Milwaukee more relevant and relatable.

Thus making storytelling an important part of talent infrastructure.

3. I promised you trust over a brewski. I meant it.

The AInxiety article ended with a goal of building trust that lets leaders admit what they don’t know. Best done over a brewski. Well, how about whiskey, too?

So here it is: Experience Milwaukee Bourbon Club is BACK!

If you were a member of the club from 2023-25, you know what this means. If you weren’t, it’s a collection of regional business and tech leaders coming together every other month at a different Milwaukee venue.

No agenda, programming, or pitches. Just valuable connections and honest conversation over your favorite pour. Even if that’s a brewski or a mocktail. (Don’t drink? We don’t care. It was never really about the booze anyway.)

The relaunch meetup is Wednesday, October 14 (during Wisconsin Tech Month) from 6-8PM. With giveaways of allocated bottles from Xorbix Technologies!

Interested? You can request your spot in the club here.

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4. Going multi-city means a slight name tweak here in Milwaukee.

On July 27, I launched a second tech-focused media publication in another city.

Why?

Because leaders there told me the same thing I’m hearing here: we need help telling our tech story.

The demand for this kind of storytelling is growing. It’s not just a Milwaukee quirk. And the model we’ve been building together right here, people first, honest conversations, and community + content, is what I’m taking there.

And that brings me to a change you’ll see here very soon. Experience Milwaukee is becoming Tech in MKE.

Same stories. Same happy hours. Same “love you, Milwaukee.”

What’s changing is that the name will finally say what this has become: a place where you can come for what’s happening in tech in MKE.

And it will sit alongside its new sister publication. (Comment if you want to know the new city.)

5. Here’s my direction as we head into fall.

Earlier this week, I asked what our unfair tech advantage is. The handful of comments on this article have been great. Keep ‘em coming!

Here’s my question added to my question.

If we’re really worried about keeping and attracting talent, but people can’t come to a place they’ve never heard of, then who’s job is it to make sure every ambitious person in and around Wisconsin has heard something about what’s happening here?

I’m living part of that answer, one happy hour and one article at a time.

But it can’t just be me. Or just a few of us.

I want to hear from you about a story you think nobody’s telling. I’ll get on it.

Love you, Milwaukee.

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• The organization Jeff leads, Sports Tech HQ, works to make Indiana a global hub for sports technology.

• A native of Indianapolis, Jeff has spent his career focused on what sports can do for a community.

• He’s a convener and connector, helping sports tech founders relocate, scale, and grow in Indiana.

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Making inroads in Indiana has been loaded with lessons.

When I jumped on this particular call with Jeff for our interview, I totally expected to geek out on sports tech.

We did.

But we also got into what makes cities special and successful when they truly lean into their unfair advantage.

You see, nearly 50 years ago, leaders in Indiana decided to lean into sports and, later, sports technology. Not as something charming to do. But to carve out a space to compete at a high level in business creation, attraction, and economic development.

50 years of intention, sometimes bold, occasionally out-on-a-limb decisions. And Jeff was kind enough to talk me through some of them in our conversation.

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The thing that inspired me the most from what Jeff shared was the state’s 2050 vision.

And, to be honest, it created a little jealousy because I wish we had that same tenacity for focus here in Milwaukee.

Because Jeff and I got into what it actually takes for a city to build an unfair advantage on purpose. And believe me, it’s not hoping the next tech trend or data center will find its way to you. It’s the ability to draft and hold a plan for decades.

I’m not going to lay it all out here. Because I think you should hear it from Jeff himself.

He gets into the bets, the vision, and more that Indiana has worked through.

And he leaves us with questions for ourselves. For our city.

Give it a listen right here or on Spotify if you’re on the go.

After you listen, go to the comments and let me know what you think is Milwaukee’s version of a 2050 vision. What is our city’s unfair advantage? I think it’s freshwater technology. What say you?

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Love you, Milwaukee.

This story is part of my city tech tour, sponsored proudly by Secure Compliance Solutions (SCS).

Quick summary of the interview:

• Kurt shares how tech plays out, or not, in the 90% of Wisconsin manufacturers with 100 employees or less. Hint: it’s not about the money.

• He also talks about the “dark factory” but that robots and automation still aren’t solving manufacturing’s biggest problem.

• Every manufacturing job creates four others. Kurt makes a strong case that what keeps Wisconsin manufacturers up at night should keep all of us up, too.

I’m the guy who loves to talk tech.

But this conversation with Kurt Bauer (LinkedIn), President and CEO of Wisconsin Manufacturers and Commerce (WMC), the tech talk was more about the people.

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Through WMC, Kurt represents 3,800 businesses in Wisconsin. Half of them, at least, are manufacturers. And when I asked him what these keeps these companies up at night, I totally expected to dive into areas like tariffs, AI/tech, or the cost of other inputs. Though each of these are weighing on the minds of business leaders, it’s people that causes the most concern.

Yes, people. Wisconsin isn’t keeping enough of them.

Baby Boomers are retiring every day and there aren’t enough of us behind them to fill the void.

At the same time, headlines are shouting how AI is coming for everyone’s job. All while some manufacturers here can’t fill a second shift, can’t bid on some contracts, and, in some case, can’t grow in Wisconsin alone.

And you wonder why I’m grumpy?

Many of the manufacturing jobs that are open are high-tech, high-pay, high-skill. But many people are simply driving by our nondescript industrial parks with no idea what’s happening inside.

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The people. That’s why I talk tech every week.

Tech is one of the key stories of this city right now. But I feature people. The familiar faces you already know and the new faces you ought to.

Because talking about what we have here is part of how careers get built and why people stay in Wisconsin.

You can’t want a job you’ve never heard of. You can’t work with people you’ve never met. Ain’t that right, Ian Abston?

So give this one a listen. Here or on Spotify.

Listen for the people. Including, maybe, you.

Experience Milwaukee is powered by Xorbix Technologies.

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NOTE: This first one is a freebie but I’m considering doing these in future weeks only for paid subscribers. Just a heads up.

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The one thing keeping manufacturing leaders up at night.

I recorded a podcast this week about the state of manufacturing in Wisconsin, what role tech is playing, what’s working, and what’s not.

Near the end I asked about what keeps manufacturers up most at night?

The answer arrived without hesitation: talent. Specifically, finding and keeping people in Wisconsin.

Emphasis on that came from a couple of other conversations this week while working on an idea to bring college journalism students into Experience Milwaukee. Yes, reviving a thesis from my first company, Spreenkler to give students real work, real bylines, real reasons to stay in Milwaukee.

One conversation opened a door deep into a major local university.

Another, with someone who sees this through an economic development and talent retention lens, helped me focus on how I should carry the idea forward.

Same problem even through different conversations: how does Milwaukee, or Wisconsin for that matter, retain its up-and-coming talent?

Lead with their pain, not your idea.

That economic development conversation gave me the single most useful piece of advice I got all week: when you walk into a room with an idea, don’t open with the idea. Understand the pain first. And let that tee up what you’ve brought.

It sounds obvious, I know. But I’ve watched hundreds of pitches (and made a few myself) that started with the solution and hoped the problem would surface later.

This was such a great reminder that I’m taking curiosity on the road with me.

I’ll be out West at the end of the month meeting with economic development, business, and tech leaders and I’m going with questions, not answers.

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For executive leaders, the AI conversation brings a hidden, complex layer of anxiety.

Conversations this week, from two different vantage points, ended eerily similarly.

One was with someone leading the AI charge inside one of Milwaukee’s legacy professional firms. They’re early in the journey of figuring out how to bring AI in at scale.

The other was an early-morning phone call with a former Fortune 500 CTO talking about what enterprise technology leaders are feeling right now.

I shared what I’ve been hearing and seeing in tech executive conversations for some time. It’s that underneath all the AI strategy decks, pilot programs, and POCs there’s a real insecurity.

CIOs / CDIOs / CTOs and the leaders who report to them aren’t entirely sure if they’re doing the right things, doing enough things, or heading in the right direction.

My former CTO friend didn’t hesitate. He’s hearing and seeing the exact same things across his national network.

It’s one thing to sense anxiety in a conversation. It’s another to have someone who spent years at the top of a global enterprise tell you the anxiety is everywhere.

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The goal I’m taking into next week.

If the smartest, most experienced tech leaders in our region are privately anxious about AI, what does this ecosystem owe them?

More case studies and vendor pitches clearly aren’t it.

Is it permission to say “I don’t know?”

Maybe it’s time to take the performance pressure off.

Let’s do what we do best in Milwaukee: grab a brewski (A or NA), a seat at the table, and sit down with friendly, honest folks and talk it out.

After all, I believe AI anxiety, like a lot of business problems at the moment, is that every leader thinks they’re the only one who feels unsure or that they’re falling behind.

And that, my friends, is b***s***.

It’s also part of why I said yes to a new role at Xorbix (I announced here earlier this month). I believe the work I’m doing can meet leaders where they are, somewhere in that anxiety.

So, the goal I’m carrying into next week is continuing to build trust that lets leaders admit what they don’t know. Whether that’s about AI or anything else. Sometimes professional things, sometimes personal. And likely over a brewski.

Love you, Milwaukee.

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• Austin Ramirez, CEO at Husco, a 1,600-person, Waukesha-based manufacturer of hydraulic and electromechanical components.

• Austin came back to Milwaukee in 2001 after school on the East Coast and work in California, meaning to stay only a year but never left.

• He’s proud of the K-12 school his family built that serves ~3,000 kids across two campuses and has ranked #1 in the state for several years running.

• Connect with Austin on LinkedIn.

The quick snapshot of my conversation with Austin:

• Husco’s nearly 500 degreed engineers design the guts of machines the world’s best-known brands put into the world.

• There’s a staggering amount of data his company collects and doesn’t yet use. The number he threw out surprised me, and it’s exactly why he thinks a US manufacturing renaissance is just getting started.

• Austin also shares something about Milwaukee’s kids that he directly calls out as a tragedy and what his family is doing about it.

I love when Milwaukee companies care so much about their city that they do something about its biggest challenges.

A lot of Milwaukee business leaders talk about the city’s challenges. Let me emphasize the a lot part of that sentence.

Few actually move on it. Do something. Get involved.

The Ramirez family, which owns Waukesha-based manufacturing company Husco, actually did something.

They started a school, Augustine Prep, to address the education gap in Milwaukee.

If you live here, or are familiar with the state of K-12 education in the city, you know what they did was big. Really big. Because Aug Prep shares on its website that “The 2024-25 State of Wisconsin Department of Public Instruction report card shows that Aug Prep remains the top K-12 school in Milwaukee, and continues to deliver one of the state’s highest rates for student academic growth.”

What does a K-12 school in Milwaukee have to do with a manufacturing company in Waukesha?

On the surface, one might say Aug Prep is a way to attract kids into the Husco’s talent pipeline.

Well, not exactly.

Though it’s great that, as Austin shares, some of the kids who have attended Aug Prep are now becoming ready recruits for the family business, in reality, the Ramirez family has a broader vision to equip students for the modern economy, whether that’s at Husco or elsewhere.

I think this is the kind of vision that makes Husco a successful manufacturer, too.

With a focus on manufacturing’s bigger picture and potential, the company moves into the future with agility and purpose.

In my interview with him, Austin shares how tech-forward Husco has been and will continue to be to build business and attract new talented people to the company.

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Austin’s wisdom hit home as I reflected on our conversation over the next couple of days.

Austin doesn’t separate the school and the shop floor like I was in my mind.

For him, building a great business and building up the city aren’t two projects competing for his attention. They’re the same project.

That’s the part I wish more business leaders around here understood.

We all talk about Wisconsin’s brain drain problem like if we just told a better story, the kids would stay.

But Austin’s point is simpler and harder: you can’t retain talent you never developed or engaged in the first place.

The kids are here. We’re just not giving all of them a shot at the economy we’ve built.

And the economy he’s building is a good one. Robots. Vision systems. Hundreds of engineers. Even a pile of manufacturing data he says they’ve barely scratched.

If you love tech, Austin will tell you there’s not a better place to be right now than in manufacturing. And there’s not a better place to do manufacturing than in Milwaukee.

Aug Prep certainly isn’t charity. And it isn’t recruiting. It’s what happens when someone decides the city they came home to is worth the f***ing work.

Take a listen below or on Spotify.

This is a good one.

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Kristin Milchanowski’s bio:

• Chief AI and Quantum Officer at BMO Financial Group, leading BMO’s AI, data, and analytics strategy.

• Author of Return on Intelligence, a 43-principle playbook for scaling AI responsibly so small businesses aren’t left behind.

• Connect with her on LinkedIn.

Interview summary:

• Kristin explains what AI actually looks like inside a bank, whether you see and feel it or not.

• She reveals the exact moment an employee’s job quietly changes when you hand them an AI “widget” and the bet BMO made on all employees.

• She declares the one trait that lets anyone keep up with AI. Hint: no tech degree required.

What’s going on in the professional tech world today?

With the full press onset of AI, there’s a lot of concern and uncertainty mixed with excitement and potential among those of us who operate in and around tech today. Hell, even if you don’t operate directly on the inside, I have a feeling you’re feeling it, too.

I mean on one hand, we’re all a little unsure of how AI is going to impact what we do professionally in the midst of already feeling the impact on how we do.

And for those of us closer to the front edge of this stuff, we’re also excited about the future and how it will create new opportunities around jobs, company creation, and more.

In an environment like this, where can we look for guidance on how to focus our energy and attention and effort?

Kristin Milchanowski is a breath of fresh air in corporate tech leadership.

When she and I sat down I immediately knew the opportunity I had in front of me: to have a real conversation on how everyone is feeling about AI in the workplace. Even more, in a bank.

And we got into it.

First, a little on Kristin, because it matters.

She’s the Chief AI and Quantum Officer at BMO Financial Group. She’s spent 20-plus years in this world and she just wrote a book called Return on Intelligence, which is essentially a playbook for scaling AI responsibly so small businesses don’t get left behind. She’s also an Oxford AI fellow with a PhD. Oh, and a licensed race car driver, but that’s a story for another day.

The point is: when someone with those credentials talks about AI, you’d expect it to go over your head. Mine included. And maybe parts of her panel earlier that morning did when she and moderator Tim Dickson (CDIO, Regal Rexnord) got into AI governance and some of the deeper technical elements.

But then she’d say something so human that the everything came into focus.

That’s the thing about Kristin. She doesn’t talk down to you, and she doesn’t dress it up to sound smarter than it needs to. She meets you where you are. And in this moment, when everyone’s a little unsure, it’s exactly what you want from someone who truly knows what they’re talking about.

What Kristin wants you to know to ease your uncertainty.

Kristin and I covered a lot in a short time: what AI really looks like inside a bank, the surprising moment your job changes, and the one trait Kristin swears matters more than any tech degree.

I could try to summarize it all here, but honestly, you should just hear it from her.

Hit play on the full conversation below (or listen on Spotify). It’s the kind of conversation that leaves you less anxious and more curious about what’s coming.

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Quick Bio:

• James Marino is President and CEO of Jackson’s Food Company, the Muskego-based maker of avocado-oil snacks.

• James is born-and-raised a Milwaukeean and is a Marquette High grad.

• Connect with him on LinkedIn.

Quick Summary:

• Jackson’s has quietly scaled its capacity 20X in just a few years. The reason why comes down to one unusual thing about their factory that most snack companies never get to start with.

• CEO James Marino walks through how a rare autoimmune diagnosis, a Shark Tank investment, and a shuttered brand all led to the “2.0” company making waves out of SE Wisconsin today.

• There’s a reason nobody touches the product from the cutting table to the end of the line and it says something bigger about where Milwaukee’s manufacturing talent fits into the future of food.

Sometimes these interviews make me hungry.

Particularly when they’re focused on a delicious snack company.

Anyway, back to why you’re here.

I recorded this conversation, my interview with James, earlier this year. Like February early. It wasn’t for lack of interest that caused the delay in publishing. It was thinking a lot about how this particular conversation fit into the editorial flow here on Substack.

For some reason, I felt it needed it’s own time and space to be published. Like after a holiday or some kind of break in my writing. Because the Jackson’s story is special.

It all started in the home of Megan and Scott Reamer as a way to help their son, Jackson, who had a rare autoimmune disorder.

They found that the way they made snacks for Jackson, and the ingredients they used, could ease Jackson’s symptoms.

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But it didn’t stop there. When friends and family got their hands on what Megan and Scott were making, they encouraged the couple to take the snacks to market!

On the shelves of Whole Foods. On the Shark Tank show. Boom. They suddenly had a real, growing company.

But in 2019, they shut down and essentially started from zero in 2020.

Technology enabled Jackson’s 2.0 to get off the ground.

Growing the way Jackson’s is growing to, of course, takes some good fortune and even better timing. Even more, it requires a great product produced with the perfect manufacturing setup.

When James and team were re-launching the company, they put all of the above together to ensure they could make the best tasting snacks in the aisle. They looked to Chicago for what happened to be the exact equipment they needed and moved everything to Muskego.

Using 50,000 square feet for production and warehousing soon became 130,000 square feet just for production with an additional warehouse / shipping facility in Oak Creek.

And they’re just getting started.

How exactly did they get this all done? Listen below and find out!

Listen to my entire conversation with James here or on Spotify.

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Who’s in this interview and what’s it about?

Sri Kantamneni [LinkedIn]: CIDO of Schreiber Foods.

Stephen Pounds [LinkedIn]: CEO of Vadar Alpha.

Summary: In this episode, I talk with Sri and Stephen about what happens when a food manufacturing giant teams up with a scrappy two-year-old startup. They break down (in lemonade-stand terms) how Vadar Alpha helps Schreiber manage pricing, risk, and the “spread” between what it buys and sells, and why the best partnerships pair deep data and expertise with the agility to actually use it. It’s a real-world look at cutting through AI hype to solve actual business problems. This is a preview of their fireside chat at Summerfest TechAI 2026 (more info and register here).

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A lot of startups are trying to sell to enterprise. Why is this different?

Every time I talk with Sri Kantamneni about what’s going on at Schreiber Foods I’m grateful that we have both in Wisconsin.

In a few short years, Sri has become an important part of the regional tech community. Not only attending events, but connecting the dots to what’s being built. And in a way, that not only helps Schreiber serve every part of its distribution and customer ecosystem better, but sometimes it also helps a startup keep starting.

That’s huge. Because the latter can require placing a big bet.

Now, when you have a guy like Stephen Pounds heading up said startup, you’ve got some serious firepower. His background in tech and finance is solid. And his company, Vadar Alpha, can turn math into metrics and decisions that matter. Which results in happier customers and sales that scale.

Let’s just say for Schreiber, their bet on Vadar Alpha is humming.

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What did I take away from this interview?

Two key things.

First, if you want to sell to the enterprise, you better bring your A-game. Solving their problem is table stakes. Often, it means you’re adding value to every step in the enterprise work and delivery streams.

Second, I learned that these two guys and their companies are leaning on tech, data, and AI to make people better and more empowered, not obsolete. Boom.

Third (did I say two key things?), in looking forward to their panel discussion with Kathleen Gallagher at Summerfest TechAI on Wednesday, June 24 at 10AM, I asked them what they were excited about. Their answers: connecting with people.

Right on.

And fourth (seriously, did I say TWO?), if you want to hear how a startup / enterprise match comes together and turns into a blossoming relationship, then you should definitely attend this Summerfest TechAI session.

I can go on and on, but you should listen for yourself.

Love you Milwaukee.

You can listen to the full conversation below or on Spotify.

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The call from Chris came from Paris.

Just past sunrise on a very early Milwaukee Friday morning, I took a call from Shazam founder, Chris Barton.

He was in Paris.

At times, I could hear the bustle behind him. Which reminded me that I was talking to someone who travels the world telling his story. Elevating his 17-year-old son in the process. Which I’m sure you’ll learn more about during his keynote at Summerfest TechAI on June 26 (details here).

We had a helluva conversation chatting like longtime friends. As a super successful founder, speaker, and soon to be author, Chris chopped it up like a pro.

He volleyed back on the questions like I suspect he does most days in interviews just like this one.

But for me, this was not just an interview. This was another pinch me moment.

I grew up in Milwaukee’s South side projects. Eventually rising through slightly less rough neighborhoods over time.

I fumbled my way into college. I didn’t know how to get in or even what the hell I was going to do once I got there. But through creative perseverance (a term Chris has coined), I did get there. And by the time I graduated from MATC in 1996 and then MSOE in 1998, I had become obsessed with technology and tech devices.

Meanwhile, in 1999, Chris came up with the idea for Shazam and in 2000 he and his co-founders began building it.

I’m not sure you can design people from two very different worlds.

Nor could you master plan to put them both on the phone together, one in Paris and the other in Greendale, a short 26 years later.

But it seems that for me, that’s how my life works.

While Chris was working on Shazam, an app that changed the world, I was in a bar using it.

Shazam is as awesome today as it was back then, too.

For discovering music? Yes.

But also for betting friends a round of drinks on what the song was that you were listening to in any one of Milwaukee’s corner bars. Then using Shazam to prove it.

Oh, the countless times I held my phone toward the speakers FTW.

So what, Steve. Why should we be excited to catch Chris’ keynote at Summerfest TechAI on June 26?

I asked Claude that very question myself. Here’s what came back:

From my experience in talking to Chris, here’s what else you’ll get.

Honest enthusiasm from the heart. Scaled founder experience and proof points from someone who’s done it. Ideas for how you can do it, too, as a founder or C-suite executive and everyone in between.

All because the guy sincerely wants to share the wisdom and give back to others.

So, take a listen to the full interview below. Or listen to it on Spotify.

Then join me in catching Chris’ keynote at Summerfest TechAI on June 26. Get more info and register here.

Love you Milwaukee.

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Who you need to know from this interview:

Tim Dickson: [LinkedIn] The maestro. The connector. The guy who is always celebrating tech in Milwaukee and who brings all of us together. Also, he’s the Chief Digital & Information Officer at Regal Rexnord. He’ll be moderating the panel with Robert and Derek at Summerfest TechAI on Wednesday, June 24 at 2:00PM CST. Register for Summerfest TechAI here.

Robert Cordova: [LinkedIn] Always keeping it real. Also, the guy who promised to give me a private tech tour at the Fiserv Forum. Oh, and he’s Chief Technology & Strategy Officer for our Milwaukee Bucks.

Derek Hyde: [LinkedIn] One of my faves to grab a beer with. He always brings the passion for sports tech and Milwaukee to any discussion. He also works as SVP of Information Technology at our Milwaukee Brewers.

Lena DeLaet: [LinkedIn] How the hell does she make Summerfest TechAI happen every year? Because she’s incredible and loves the work she does for our city. Which reminds me, Lena is Director, Sales & Summerfest TechAI.

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Quick summary of the interview:

• Robert and Derek reveal how AI is quietly reshaping what you experience at the game, often before you’ve even walked through the gate.

• There’s an AI agent working the Milwaukee sports scene right now, and she’s been busy in a lot of inboxes. Who is she, and what’s she up to?

• One local team has fans opting into face-scanning technology at a rate that surprised even the people who rolled it out and the number says something bigger about Milwaukee.

• Plus: how the smallest market in Major League Baseball is using AI to punch way above its weight and a preview of the panel Tim Dickson is moderating at Summerfest TechAI on June 24.

What can I say about when Lena, Tim, Derek, Robert and I get together?

It’s been a few years since this group convened an Experience Milwaukee podcast conversation about the city’s sports tech scened. And the last one included Kenny Ansel from the Green Bay Packers (we miss you Kenny!).

There’s such a chemistry from this group. So much that I often wonder why we all just gel on and off the mics.

Here’s what I think.

We all love tech, Milwaukee, sports, and community building. When you mash all those together, you get this group.

And that’s where all the love comes from.

So what’s in store for sports tech at Summerfest TechAI this year?

As much as we dug in and jumped around, we only scratched the surface of what you’re going to get from the panel comprised of Tim, Derek, and Robert at Summerfest TechAI in just a couple weeks.

Tim, as the panel’s moderator, always comes prepared. Derek and Robert always bring their A-games. You’re going to learn a lot, have a few laughs, and walk away with three tech leaders in your network.

To get to the precise details on the panel and all the Summerfest TechAI programming, go here.

From AI agents to facial recognition technology, not to mention the core technologies that run game day, Derek and Robert sure have their hands full.

I hope they hit on what their talented teams look like in this panel discussion. And how people like you and me can apply LOL.

Jump in and listen to the conversation.

There are a few low key good jokes I drop in this one. Even Robert starts us off with a banger of a dig on Tim.

It’s worth a listen.

Plus, it’ll give you some prep for the panel to ask some damn good questions yourself.

Either way, when you go see this group at Summerfest TechAI on June 24, be sure to get a selfie with them!

Love you Milwaukee.

You can listen to the interview below or you can listen on Spotify here.

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Celeste Cuffie, Chief People Officer and Co-founder, Cream City Cyber (photo by Robert Dodds)

• LinkedIn

• Celeste owns culture, strategy, and communication at Cream City Cyber and brings a people-first lens. She stands strong that most “technology problems” are really culture and communication problems in disguise.

• Holds a doctorate in strategic leadership; her research and practice center on how people adapt (or get left behind) as technology accelerates.

Sheldon Cuffie, CEO & Co-founder, Cream City Cyber (photo by Robert Dodds)

• LinkedIn

• Cybersecurity veteran with expertise from enterprise security leadership at companies like American Family Insurance and Northwestern Mutual.

• Specializing in security strategy, cloud security, governance and compliance, and resilience, Sheldon is now bootstrapping a second Milwaukee-based venture, Cream City AI.

Lena DeLaet, Director of Sales & Summerfest TechAI (photo by Robert Dodds)

• LinkedIn

• Has grown Summerfest Tech from a three-hour local gathering into a four-day national conference.

• A champion of Milwaukee who came up through media sales and now works to convene every sector of the tech community while weaving in the Summerfest music festival experience.

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Summary:

• Sheldon and Celeste share how they bootstrapped Cream City Cyber from scratch into a nearly 40-person, multimillion-dollar cybersecurity firm in the last 18 months.

• They also announced they’re now launching a second Milwaukee venture, Cream City AI, focused on the human side of adoption.

• They make the case that AI is moving at “light speed,” but the real risk isn’t the technology, it’s that people don’t change at that pace, and companies keep dressing up culture and communication problems as tech problems.

• On the cybersecurity front, Sheldon warns that AI is becoming “a firecracker on top of a rocket ship” with non-human identities and agentic AI multiplying risk at organizations that don’t even have control of their human identities yet.

• The conversation turns to Milwaukee’s biggest challenge: exporting homegrown talent instead of retaining it, and why Lena sees Summerfest TechAI as a way to connect the region’s students, startups, corporations, and investors in one place.

I had a beer with Sheldon, Celeste, and Lena. And that’s why I love this work.

Typically, when I sit down for a beer it’s to get into a tech conversation.

This particular Tuesday, my beer was poured at Boone & Crockett (my first time there), and the discussion immediately got nerdy.

I found myself quickly jumping in with Sheldon and Celeste Cuffie, the husband-and-wife team behind Cream City Cyber. We were also joined by Lena Delaet, from Summerfest TechAI to talk tech and about this year’s partnership between the two organizations.

In the midst of all the nerdiness, Celeste kept us grounded. She reminded us at each turn that the focus of tech should be on the people making it happen and those affected by the outcomes.

“Let’s remember to say ‘please’ and ‘thank you!’

And that grounding mattered, because Sheldon and Celeste have a lot to be nerdy about. They’ve bootstrapped Cream City Cyber into a nearly 40-person, multimillion-dollar cybersecurity firm in about 18 months.

Sheldon, Cream City Cyber’s CEO, is decades deep in enterprise security. Celeste, the firm’s chief people officer, is the perfect match to keep the company balanced. While Sheldon talked threat landscapes and rocket ships, Celeste would pull the conversation back to humans.

Because AI is moving at light speed. The tools are racing ahead. But, as Celeste said, people don’t move at that same speed. That can create problems. On the surface, leaders might see these as technology problems. However, Celeste points out that they’re more often culture and communication problems.

The fix? Sometimes it’s just remembering to say please and thank you.

Thanks to Concurrency and Secure Compliance Solutions, sponsors of Experience Milwaukee!

“A firecracker on top of a rocket ship!”

Sheldon doesn’t sugarcoat where the tech security is headed. He shared just hoq quickly AI and its extraordinary promise can turn into real danger if you handle it wrong. His worry is that most organizations don’t have a handle on their human identities yet, and now we’re handing the keys to non-human, agentic AI.

Then, the conversation turned to tech in Milwaukee.

Sheldon named our city’s problem directly: we grow incredible talent here, and then we export it. We’ve got the universities, the graduates, the manufacturers, the banks, the insurance giants. What we don’t do well enough is give people a reason to stay. Celeste pushed it a bit further: it’s not just about keeping people, it’s about access. Who gets into the room and who doesn’t.

And that’s exactly where Lena comes in.

Lena sees Summerfest TechAI as one of the answers. It’s a place where students, startups, corporations, and investors come together to build stronger relationships. And the partnership with Cream City Cyber this year is a piece of that: local working with local (I LOVE IT!).

So, yeah, I had a beer with Sheldon, Celeste, and Lena. And in our attempt to denerdify the nerdiest of things, I learned once again that tech conversations aren’t always about tech. They’re also about people coming together and bringing everyone along for the ride.

You can find out for yourself at Summerfest TechAI on June 23–26. Register today!

This article is part of our 2026 Summerfest TechAI series, sponsored by Cream City Cyber. Listen to the full conversation below or listen on Spotify.

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The full audio of my conversation with Mandela can be found at the end of this article. But here’s a preview.

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Mandela’s Quick Bio:

• Former Lieutenant Governor of Wisconsin and U.S. Senate candidate.

• A Milwaukee native and vocal advocate for economic equity, he’s championed policies that expand access to tech, education, and opportunity for communities too often left behind by innovation.

• Now running for governor, Barnes is making the case that Wisconsin’s best days are ahead, if the state invests in its schools, retains its homegrown talent, and holds corporations accountable as AI reshapes the workforce.

Quick Interview Summary:

• Mandela Barnes makes the case that Wisconsin has everything it needs to compete: affordable cost of living, homegrown talent, and a deep manufacturing and innovation heritage, but has to stop letting that talent walk out the door to Chicago, New York, and LA.

• On AI, he’s direct that it’s not a train that can be stopped, but companies using it to eliminate good-paying jobs should be denied the tax incentives they’ve grown accustomed to receiving.

• From fully funding public schools to increasing support for the UW system, Barnes sees education as the foundation for making Wisconsin a state where startups can scale and workers can thrive in the age of AI.

• He draws a straight line from his grandfather’s union steel job in Milwaukee to today’s workforce disruptions and argues that if we’ve seen this story before with factory closures and offshoring, we can’t afford to repeat the same mistakes with artificial intelligence.

Let’s hear it for Concurrency and Secure Compliance Solutions! Their financial support keeps the Experience Milwaukee machine running so I can bring stories like this to life!

I wasn’t sure what to expect from this interview with Mandela.

For the last couple years, of all the candidates running for governor in Wisconsin right now, I’ve spent the most time talking with Mandela. And watching him mingle at events.

He shows up.

Not just at the “who’s who” type of events. All the events.

That’s what I’ve always admired about him.

So when I had the chance to chat with him on his vision for tech in Wisconsin, I was curious as to what his point of view would be. Because this is something, whether in person or text, we’d never really talked about.

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The first thing you notice about Mandela is his calmness.

Maybe it’s more a quiet passion for the stuff that’s required of someone to run for a public position like governor.

In our conversation, he maintained an even tone. He never overcomplicated his dialogue, whether about politics or technology. And he tied it all together from beginning to end with perspective from the past, present, and future.

It’s hard not to like a someone who keeps it real.

So where do we go from here?

Like all the candidates, Mandela shared the “we need to…” perspective for tech, innovation, and our state’s economy. Which, in a way, was reassuring that the things that are important to Milwaukee’s tech community are also on the mind of whichever one of these candidates becomes our future state leader.

Funding education. Increasing resources, specifically financial resources, for companies to start, grow, and stay here. Keeping the talent we develop engaged and living here long term. Will whoever wins the election get these things done?

Because whether gross domestic product, talent drain, investment per capita, people moving away, and more, Milwaukee is not just trailing cities that used to be peers, we’re continuing to fall behind.

The time is now to unify the state on a vision for how Wisconsin participates not just nationally, but globally, in the tech economy. Today, we do not have such a vision.

Whether our next governor is Mandela Barnes or any of the other candidates I’ve talked to, we need a strong vision with even stronger follow through. Urgently.

Here’s my full interview with Mandela. You can also listen on Spotify.

Brooke Casazza’s quick bio:

• LinkedIn Profile.

• Leads the Bucks’ revenue-generating tech stack, everything that drives ticket sales, marketing, and fan engagement, plus shapes the organization’s enterprise AI strategy from governance to real-world application.

• Came up through AT&T and Samsung with a gift for making tech easily understandable, which landed her in the Bucks’ IT team as the bridge between business problems and technology solutions.

Michael Dairyko’s quick bio:

• LinkedIn profile.

• Oversees a three-pronged analytics operation covering data science, business intelligence, and market research, all focused on the fan experience and the business of basketball.

• Holds a PhD in applied mathematics from Iowa State, got recruited into sports via our Milwaukee Brewers, and landed at the Bucks after being handed a business card mid-conversation at a networking event.

Can Mike predict when someone is going to retire from basketball?

Claude’s interview summary:

• Brooke and Mike share how the Bucks think about AI as a productivity and revenue driver that touches everything from ticket sales and concessions to fan engagement.

• The majority of Bucks fans will never set foot in the Fiserv Forum so the team is building a connected digital ecosystem to engage, personalize, and delight fans wherever they are.

• From a PhD in applied mathematics (Mike) to a career in cell phone sales (Brooke), their career paths into sports tech were anything but linear and their advice for the next generation is refreshingly practical.

• Both see Milwaukee at an inflection point where investing in data, technology, and local talent could flip the script on brain drain and make the city a serious tech destination.

I almost got lost heading to the interview.

When one has the opportunity to visit the global HQ of our beloved Milwaukee Bucks, one must hustle to make it happen. Being late isn’t an option. And this is coming from someone who just mishandled their calendar and missed a meeting with Bill Davidson from THE Harley-Davidson, another beloved Milwaukee brand.

So, I left early for this interview with the Bucks and I’m lucky I did. I have zero map reading skills. So I new I was doomed when a map was provided to me in an effort to make it easier to locate the Bucks front door. However, after about twenty minutes of searching, I did make it there on time.

Anyway, enough about me and my shortcomings.

Because after all, I did get in and then I got to spend time inside the sacred place with Brooke Casazza, Director of Sales and Marketing Enablement, and Mike Dairyko, Senior Director, Business Strategy and Analytics.

Here’s what happened.

How AI started at the Bucks.

Before the Bucks built anything with AI, they asked a simple question: what is AI? Brooke, who leads the Buck’s enterprise AI strategy, said that getting clarity around that question was the top priority.

You see, she’s getting bombarded with sales calls every day from people selling AI tools. So the team had to cut through the noise and get aligned on the problems they were actually looking to solve, and what responsible use looked like inside their organization.

Most Bucks fans will never step foot in the arena.

Though a definite eye opener, this is just one of the insights that drives a lot of what the Bucks are building.

Whether it’s the frictionless checkout experience inside the Fiserv powered by computer vision, or the personalized digital touch-points for fans who only follow the team from their couch (i,e. me), the Bucks are thinking about the entire connected ecosystem not just the 18,000 people in the seats on a game night.

The data goes deeper than you’d think.

Mike, who holds a PhD in applied mathematics and spent time at the Milwaukee Brewers before joining the Bucks, oversees a business analytics operation that spans data science, Power BI dashboards, market research, and even HR analytics.

Interestingly, it’s NOT about what’s happening on the court.

It’s all about running a smarter business. From staffing the arena efficiently and understanding the voice of the fan to helping sales and marketing teams make faster, better decisions.

Think about it. The Bucks are using an enormous amount of data and analyzing that data to make sure every way you interact with the team brings you value.

Quick note: Let’s hear it for Concurrency and Secure Compliance Solutions! Their financial support keeps the Experience Milwaukee machine running so I can bring stories like this to life!

So how did Brooke and Mike land these jobs?

Brooke sold cell phones. Mike wanted to be a math professor. Neither planned on ending up in sports.

But both landed here because they could take complex problems and translate them into language that moves people to action.

Their advice for anyone trying to break into tech? Be curious. Ask questions. Build in public = don’t be afraid to try things and to get feedback on those things.

Oh, and don’t wait until you have all the answers before you walk into the room.

Like I’m hearing from all of my guests lately, Milwaukee is at a tech inflection point.

Both Brooke and Mike see potential in Milwaukee.

The talent is here. The industries are here. What’s been missing is the willingness to treat technology as a strategic function, not just a support function.

The Bucks are trying to model what that looks like.

And if more Milwaukee companies follow, both believe the brain drain to Chicago, New York, and LA starts to slow down.

Hell yeah.

Here’s the full conversation with Brooke and Mike.

You can also listen on Spotify here.

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The full audio of my conversation with Kelda can be found at the end of this article. But here’s a preview.

Kelda’s Quick Bio:

• Kelda is a Wisconsin-born attorney, state senator, and tech founder running for governor.

• She has over two decades of bipartisan legislative wins and a track record of turning big ideas into law.

• She’s a tech entrepreneur who founded a business to make home-buying more affordable, and a champion for Wisconsin’s startup ecosystem advocating for the capital access and policy reforms that help homegrown companies scale without leaving the state.

• She’s also a mom and stepmom of five.

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AI’s take on my interview with Kelda:

• Kelda makes her case for why she’s the most experienced candidate in the Wisconsin governor’s race and what that experience actually means for the state’s tech and business future.

• She also talks about why Wisconsin keeps losing startups and talent to neighboring states, and the concrete policy fixes she’d push as governor, including a bigger state fund-of-funds for growth-stage companies.

• Her take on building a statewide culture that embraces risk and failure, and why that mindset shift matters as much as any tax credit.

• A candid conversation about healthcare, small business, and what other candidates are getting wrong about economic development.

Here’s my take.

This interview with Kelda was unlike any other of the three candidate interviews I did leading up to this one (which now makes 4 of the 8 gubernatorial candidates). I’m batting .500 and doing math on Substack.

As a tech guy worried about where Milwaukee and Wisconsin are headed around technology, it was refreshing to hear specifics on policy and language from an actual tech founder. Now I know there are other things the next Wisconsin governor will need to know beyond technology, but I write about tech and Kelda knows her stuff.

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What you won’t hear in this recording is numerous breaks she and I had to take because of traffic sounds, horns, sirens….OMG I was worried she was getting ticked off. But she rolled with it and this turned out great because it’s informative and you can hear the uplifting vibe our conversation had in the absence of the edited out background noise (we recorded live on the Great Lakes Distillery patio).

I want to say more, but the twenty minute conversation says it all. Take a listen here or on Spotify.

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Before I forget…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.

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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