• Andrea has spent 15 years at CLA working with privately held and private-equity-owned manufacturers on audits, company sales and acquisitions, and owner transitions.

• She’s a UW Whitewater grad with a degree in accounting and finance.

• Andrea is also involved in Women in Manufacturing, helping to relaunch its SE Wisconsin chapter.

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It rained the whole way there.

I wasn’t sure what to expect on this journey, this day.

I was headed to a CPA firm to talk about audits, manufacturers, and private equity (PE). All things that fascinate me, but not exactly the usual tech beat.

Or so I thought.

Then Andrea sat down across from me and called tax season “opportunity season.”

I mean, us non-CPA types dread tax season.

So when she dropped the light-hearted euphemism, I knew this would be fun.

What does a CPA do?

For Andrea, the busy season is January through April. There are audits, reviews, financial statements, and everything else banks and PE firms require.

But her day-to-day is different.

She helps companies buy or sell other companies. She helps business owners work on what comes next, whether that’s a family handoff, a sale, or something else. All wrapped up in a strategic planning kind of way.

And she told me she hasn’t built a financial statement in years. She reviews them, but mostly she builds relationships.

“That’s not how I pictured my career would go at all,” she said.

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$500M put me in the room.

Here’s what initially caught my attention and my outreach to Andrea (thanks for the intro Lori Highby!).

I read that CLA was investing half a billion dollars into technology.

So, I asked Andrea about that.

She said CLA’s CEO indeed had pledged the $500M tech investment and here’s why.

There are fewer CPAs entering the profession. CLA wants to automate the data entry that eats up so much time in January through April and empower the team to focus on more value-add efforts.

As Andrea says, “No one wants to work 80+ hour weeks anymore.”

But isn’t AI coming for CPA jobs?

I mean, these are the headlines we’re all reading, correct?

Well, I heard the opposite from Andrea.

The $500M investment, she told me, is meant to bring more people into the career. If you take out the work few people really enjoy, the profession looks more appealing to someone deciding what to study.

Though it’s too early to see how this all plays out, it’s a better scenario than what the headlines are portraying these days.

What the heck else did we talk about?

The owners (and founders) who plan early, win.

Women in manufacturing.

What Andrea says to young women thinking about a career in finance, accounting, or manufacturing.

But you’ll have to listen below or on Spotify for all of those details.

Andrea is actually a self-described introvert.

But she was grateful we were sitting at the table talking. So was I.

I drove out there in the rain, not sure what I’d find.

I picked up some wisdom and a new friend. Totally worth it.

Love you, Milwaukee.

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• Currently, Tim is CIDO at Regal Rexnord where he’s been for the last 3 years.

• Regal Rexnord is a 70-year old industrial manufacturer that began in Beloit, Wisconsin and merged with Milwaukee’s Rexnord in 2021. Regal Rexnord makes products that transmit power and controls motion.

• Tim grew up in La Crosse, Wisconsin, and has spent years of his career in other major tech cities. He came back to Wisconsin to become Chief Information Officer (CIO) at Generac in 2020.

• Tim is one of the most visible tech leaders in Milwaukee, from local meetups to Summerfest TechAI and LinkedIn. Milwaukee runs through his veins.

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I love going behind the scenes at Milwaukee companies.

This is especially true when it’s Regal Rexnord to visit my good friend Tim Dickson.

Regal Rexnord’s HQ is right in the middle of downtown Milwaukee. It’s easy to park. You can see the 3rd Street Market Hall from the windows of the building. And one of my favorite local, craft distillers is a block away. (It’s Central Standard in case you were wondering).

When you walk into the lobby at Regal Rexnord, it’s basically a history wall of everything the company has made over the last 70 years. Gears, couplings, and parts that move things around the world.

I’ve never seen Tim beam with pride like he does when he walks visitors through the space. I can tell he loves it here.

When he greeted me, he walked me through the space again, launching into a tour until I reminded him I’ve heard it all before.

We laughed and he then walked me down the hall to the conference room Tim actually interviewed in three years ago. He told me this was the room that made it all happen.

Another day and another seat at a table I know I’m lucky to be at.

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“Tim makes it fun.”

That’s what Reshad Alam, Regal Rexnord’s singing CISO (Chief Information Security Officer), told me about Tim. (You can read/listen to my previous conversation with Reshad here.)

I asked: How you make a 70-year old manufacturing company’s tech team fun?

Tim said that when he interviewed, he saw a company with deep engineering and years of product innovation. What he didn’t see was energy around the tech or an identity for the team. And No brand in the city.

Those things are Tim’s secret sauce.

So he made changing those things his goal.

How?

Encourage people to bring their courage, creativity, and personality to their work. Make it safe to take risks. Innovation follows.

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The sign at the airport.

Tim’s brother lived in Milwaukee and worked at Milwaukee’s iconic Harley-Davidson for 20 years. Tim grew up in La Crosse, Wisconsin and moved away in high school. But he kept coming back to visit Milwaukee for things like Summerfest and Bucks and Brewers games. His brother, Tim said, is the reason he learned to love this city.

Fast forward to 2020, during COVID. Tim is flying to Milwaukee from DC to interview with Generac.

He gets off the plane at Milwaukee’s Mitchell airport and sees a sign on the wall: “Milwaukee, the Midwest’s most underrated city.”

That sign changed things for Tim, right there in that moment.

He took it personally. He thought of it as a message to him. That, if he got the job at Generac and moved his family here, he wanted to help turn that sign upside down. Or, as I said, “to rip it off the wall.” He didn’t argue.

He told me there are 100s of Tim Dicksons in bigger cities. in Milwaukee, he can stand out and matter. Milwaukee is the right size, the right culture, and in 2020, it was the right time.

We’ve gone from “should we” to “we’ve done it!”

I asked Tim what he’s seeing from his tech leader peers that gets him excited.

“Over the past two or three years, Milwaukee’s tech leaders have moved from “should we do this?” to “we’ve done this, let’s scale it!” Companies are getting real value from AI, sharing use cases (problems they solve with technology), and talking openly about what failed.

As someone who has written about Executive AInxiety, this makes me happy.

He pointed to data centers coming to the area, universities with strong AI programs, and local leaders collaborating more. From his perspective, AI became a reason for people to work together.

Behind the scenes, he and Reshad have hosted a private gathering of CISO’s for the past three years. “People get vulnerable in those rooms,” Tim said.

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So, what kind of tech city are we?

I’ve said Milwaukee IS a tech city and we should stop debating it. The better question is, what kind?

Tim, of course, had an answer.

Look around. Regal Rexnord, Rockwell Automation, Harley-Davidson, GE, Milwaukee Tool, Clarios, Johnson Controls. These are all companies that make and move things. And across all of them, the work is changing through automation and AI.

His answer: Industrial innovation and automation. The old and the new, in one sentence.

“We could own it,” I said.

He agreed. Nobody else, he told me, is claiming it.

Two asks for every Milwaukee tech leader.

I ended our conversation with this question: What’s one thing you want every Milwaukee tech leader to do differently in 2027?

Tim had two things.

First, step outside your company’s four walls. Coach someone through i.c.stars. Speak to students. Go to a meetup. Talk about something that might be a bit controversial.

Second, invest in your people. If we want to be a tech hub, our teams have to keep learning AND they have to want to stay.

Near the end, I told Tim something from the heart. He said there are hundreds of Tim Dicksons in other cities. I wish Milwaukee had 100 Tims here.

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

Love you, #Milwaukee.

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For this article, I interviewed Matt Sabljak of SRH, a brand / creative / media agency in the heart of the Walker’s Point Innovation District.

• Matt describes SRH as an agency that helps brands become more memorable, with an in-house media team that gets real results.

• SRH was one of the first tenants in the Eagleknit Building and the team now has 20 more people than when the agency started in Matt’s condo kitchen.

• Matt’s been getting louder on LinkedIn with a video series with a thesis that brands that get remembered get chosen. He wears magenta in all of these videos.

  ---

I hadn’t even asked a question. Matt kicked off our interview with “pass.”

I mean, who the hell does that?

Matt Sabljak, that’s who.

Somewhere in our two decades of friendship he and I fine-tuned our banter. It takes all that we have to stay on track in any conversation. This interview no exception.

On this day, I caught him at the tail end of exhaustion from a huge pitch. he and the SRH crew had been working on for a couple of weeks. A couple of weeks of 16 hour days, including weekends.

On this day, Matt and I were sitting at a long table in a meeting room at the SRH global HQ, nestled perfectly in the Walker’s Point Innovation District.

It’s a space that any creative would dream to work in. A space that SRH signed a lease to in a season when other agencies were doing the opposite and going fully remote.

But for SRH, nothing replaces being together and bouncing ideas around the space.

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“Brands that get remembered get chosen.”

That’s not just the thesis behind Matt’s videos, it’s the North star for SRH.

As Matt puts it, marketing has 2 jobs: build demand and harvest demand.

But somewhere over the last 25 years, the industry leaned so hard into harvesting, that it forgot how to help people like you and me get to know the brand in the first place.

So the question today becomes: how in will people remember you?

Steve: “What about AI?” Matt: “It’s changed nothing about the way we think about growing brands.”

I mean, I had to ask.

And Matt countered with, although AI is a powerful tool that’s changing how work gets done, it hasn’t changed the principles of brand growth.

Matt’s take is that every technology comes with the same panic. But, it’s not technology that matters in how brand’s get chosen; it’s memorability.

His own proof is simple.

He picked magenta, one of SRH’s colors, and wears only that in his videos. People often come up to him and say they love his pink videos.

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Why aren’t more companies doing this?

Because it can feel too basic.

As Matt puts it, we’re surrounded by CRMs, tracking pixels, and accountability in the c-suite, so “be memorable” sounds too simple. B2B marketing pushes this even further.

His counterpoint to that, is this: we’re not rational thinkers who sometimes feel. We’re feeling creatures who sometimes think. Even if we’re buying heavy equipment or SaaS platforms.

He pointed out the Volvo with Jean-Claude Van Damme example of doing the splits between two moving semis. That was memorable.

The Saturday night Matt decided to start over.

If you’re ever struggling to make a point, make a music correlation.

Matt did.

He was telling me how close the SRH team was on completing a prospective client pitch deck late on a recent Saturday. Something wasn’t sitting well with him, so Matt decided to clear his head. He turned to the Oasis documentary to do so.

In watching how the two Gallagher brothers from the band came back together over a decades long argument that broke up the band, it hit Matt. “This whole pitch was like cover music,” he told me.

It wasn’t an SRH song. Their song is about who they are: a group of curious, passionate people who love the work and each other.

So he went back to the team to start over. They did.

At the time of our interview, they hadn’t heard a decision from that prospective client.

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Milwaukee made it possible.

Near the end of our conversation, I asked Matt what this city means to him.

There was a long, heavy pause.

He’s born and raised here. His dad worked in the newspaper industry for 50 years. He shared stories of coming to downtown Milwaukee before condos and restaurants.

Then, he told me that Milwaukee felt accessible in a way that other cities didn’t. And that’s why he got into filmmaking. And launching his own creative agency.

His focus for SRH today is not to build a great Milwaukee agency. It’s to build a great agency that happens to be in Milwaukee.

If you want all of the above and more in a passionate, honest, vulnerable conversation, listen below or on Spotify.

After you listen, RSVP for a special AI vs. Brand discussion Matt and I are co-hosting with brand strategist and author Gair Maxwell at Great Lakes Distillery on Wednesday, October 28 from 7:30a-9:30a.

Love you, Milwaukee.

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• Wes and his team develop Komatsu’s next generation autonomous system for its mining portfolio.

• He studied mechanical engineering at Milwaukee School of Engineering (MSOE), started at Komatsu as an intern, and never left.

• His team works across Komatsu’s factories around the world from a base right here in the MKE!

There’s a coffee shop hiding inside a mining equipment company in the Walker’s Point Innovation District.

I met up with Wes after strolling through the front lobby at Komatsu. It’s a public space with a coffee shop, a calm waiting area, a company history wall, and plenty of interesting, hands-on Komatsu artifacts.

A few minutes before meeting Wes, I had responded to a text from my friend David Fockel about being at Komatsu. He quickly texted back, “Are you working from their coffee shop?”

It hadn’t dawned on me that I could do that. But, maybe I should do it more often.

People often ask how I find these places and people. I guess I’m fortunate to be able to do this work. Because, more often than not, I just show up and ask questions.

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You’ve probably driven past this building, too.

Komatsu acquired P&H, a longtime maker of mining equipment and Wes worked out of its old facility here in Milwaukee. When he told people where he worked, they’d ask what he did there.

“I work on mining equipment,” he’d say.

He’d get something similar to this back from whoever he was talking to…

“My grandfather spent 40 years in manufacturing there. He ran a lathe. But he never knew what he was building.”

To me, that’s the fascinating part of making things this big at Komatsu.

The machines are enormous, so the finished product rarely sits in one place. Pieces are built, loaded onto rail cars or semi trucks, and then put together on site by Komatsu dealers. Wes called it “big Legos.” Even inside the company, he shared, not many people see the final machine up close.

And Komatsu doesn’t advertise to the public. The company sells to billion-dollar mining companies, not people like me. So the building and the work in it often stays a mystery to most of us.

Can you understand why I wanted to sit in their lobby?

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“If it’s not grown, it’s mined.”

One of his first bosses at Komatsu often told Wes the above.

From steel in our city’s buildings, raw materials in our phones and computers, all of it comes from mining.

And the sites that Wes described are massive. Think small cities. They’re also factories with raw materials going in and finished products coming out.

Driverless trucks aren’t new to Komatsu.

Komatsu was one of the first to market with a fully autonomous haulage system. That was almost 20 years ago. Over the last year, they celebrated more than 1,000 autonomous trucks commissioned in the fleet, roughly 1/6th of the global fleet are autonomous.

I thought of Waymo. And I asked Wes about the comparison of what happens with autonomous engineering between Waymo and Komatsu.

Both companies work to attract the same kind of talent. Both rely on a similar original equipment ecosystem. Both are developing similar technologies. However, Komatsu designs for the harshest of environments in a 24/7 operating mindset. That’s pressure.

It’s not what you’d picture a mining job to be.

As Wes puts it, a lot of people still think of mining as a pickaxe and a rock. Nope.

Wes dubs his team as a “mini Silicon Valley.” He has roboticists, automation specialists, software engineers, and more.

Even when I toured the manufacturing floor, I noticed that it was clean, high tech, and full of people looking out for each other.

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The advice from Wes: bring your curiosity.

He didn’t plan on what he’s into professionally. Wes told me he didn’t even think he’d stay in Milwaukee because he didn’t think this kind of work existed here. He got the internship by fluke and didn’t know Komatsu was here. “Like many Milwaukee locals.”

And yet, both Wes and Komatsu have grown together. Because of the people there.

And for anyone considering a similar path, Wes says it’s hard to teach passion, so be curious.

If you like what you’ve read, then you need to listen to the full conversation below or on Spotify.

And maybe, one morning, stop by the Komatsu lobby and grab a coffee.

Love you, Milwaukee.

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• NVNG stands for Nothing Ventured Nothing Gained. It comes from the team’s roots at the Wisconsin Alumni Research Foundation (WARF).

• The NVNG fund is ~$50M and raised from Wisconsin corporations.

• NVNG invests in venture capital managers, not directly into startups.

• The NVNG portfolio includes ~24 venture funds and ~430 startups.

• Grady created +Venture North, an invite only event that brings venture funds, corporate investment groups, family offices, and more to Milwaukee every fall for the past four years. Experience Milwaukee is an invited partner.

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The bar wasn’t open yet (darn). The coffee was.

Grady and I met at The Pfister on what felt like an ordinary early morning. It was kind of humorous to us that people were walking by the entire time we were there. But nobody knew what we were recording.

I’ve wanted to record at The Pfister for years.

I’m glad I got to finally do that with someone who gets venture capitalists from around the country to come to Milwaukee.

Tuesday with Grady and coffee. So far, so good.

Grady invests in the people who invest.

He calls NVNG “the capital for the top of the capital.” NVNG puts money into venture capital firms who then put money into startups.

If you let him, Grady can get pretty deep on this stuff. Before you know it, you’re like, “what?!?”

So, in this interview, I keep him focused.

His view on what NVNG does? You can’t do this kind of work to be nice.

“Venture capital is a global sport,” he told me. A term sheet, which spells out an investment in a startup, for a Milwaukee founder should look the same as one might look for a founder in California, Boston, or New York. Because one day that founder will need a five or ten million dollar check, and the people who write those checks, according to Grady, don’t really live here in Milwaukee.

So he follows the innovation. A lot of his portfolio is in deep tech in places like Texas and across the Midwest. Wisconsin, he hopes, eventually.

What if we got them to come here?

Grady has 431 startups in the portfolio and few, if any, can get the attention of a Wisconsin corporation who might become an early customer or who can at least help validate the startup’s offering.

Ask any founder. It’s simply damn hard to get those kinds of meetings.

So Grady’s response was to start +Venture North, a free event built to help foster those important connections, even if the founders aren’t in the room.

About 250 people attended the first event a few years ago. And, at a glance, likely several hundred this year.

The vibe is interesting. You have a room full of people managing a lot of money. Or they’re managing a lot of very interesting, high growth startups. Or both.

But everyone is there to find ways to work together.

Jump into our conversation.

Grady can only do this a day or two a year. His goal is to make that connection run all year.

He’s definitely not short on ideas.

And he says it would be great if, in ten years, nobody at +Venture North needs a name tag because everyone will know everyone in the room. Love that.

Even though +Venture North is invite-only, I sat down with Grady at The Pfister so you could get in on the conversation.

Listen to our chat below or on Spotify.

Love you, Milwaukee!

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But first, let’s get to know today’s guest, Frank Di Meglio:

• Born Francesco, he goes by Frank, and moved to Milwaukee from New Jersey three years ago with his wife and daughters.

• His office covers Ozaukee County to Kenosha County and has about 250 advisors and associates.

• He started with Northwestern Mutual (NM) as a college intern 16 years before he moved to Milwaukee.

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This is why I took the NM coffee.

I’m just going to get this out of the way up front because I’m guessing you saw this was an article about NM and you’re thinking, “why is Steve going to talk about financial advisors?”

I get it.

Because, for months, people were telling me I needed to meet this Frank Di Meglio guy. And I was skeptical.

You, too, right?

I mean, I’m fairly certain that what I’m about to say has happened to all of you at some point. (If not, it will.)

Here’s the scenario: You’re on LinkedIn when suddenly a message pops into your inbox. It’s a financial advisor. They arrive with a nice, warm, and personal intro and they ask if you’d be up for a coffee meeting to expand both of your networks.

You hesitate.

That was me years ago when I was getting my first company, Spreenkler, off the ground. An advisor reached out and not only was I skeptical, but I figured I didn’t have time for the coffee meeting.

I took the coffee anyway.

Six or sevent years after that coffee meeting, when something unexpected happened, I had cash available I wouldn’t have otherwise. I’ve never forgotten that.

Still, when it came time to have a coffee and a conversation with Frank from NM, I wasn’t sure what to expect. I assumed we’d talk mostly about money and finances.

Nope.

We talked about people. And Milwaukee.

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Frank’s been here three years but if feels like he’s a lifelong Milwaukeean.

It’s interesting to get a guy’s take on Milwaukee when that guy moved his family here from New Jersey where he was born and raised.

Frank told me when he was being shown the city, his realtor apologized for the highway traffic. Frank wondered where the traffic was.

Living 20 minutes outside of downtown, Frank loves that he can get to a Bucks or Brewers game or to a great dinner with ease.

Within just a few weeks of arriving in Milwaukee, he joined a few local clubs and never felt like an outsider. This, in a city where people still ask where you went to high school.

I’m born and raised in Milwaukee and, in all honesty, I get grumpy about this place.

Frank sees things like our festivals, concerts, and more, things I take for granted, and he’s grateful for every bit of it because he knows Milwaukee is unique.

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So did we ever get into the numbers a financial advisor lives by?

Sort of.

But we talked more about people and why they matter. And why their goals matter. And finding out if they’re running a business of their own. What keeps them up at night? What gets them up in the morning?

If you listen to Experience Milwaukee, then you know I ask these kinds of questions of my guests all the time.

Hearing them come from Frank made me change how I see financial advisors reaching out on LinkedIn or anywhere else.

So, next time, take the coffee.

Thanks Frank’s advice to you, Milwaukee. Mine, too. And he and I say it without hesitation. Take the meeting.

Worst case, you get a free coffee and meet someone new and connect through each other’s networks. Best case, you get asked questions that change how you think about your own plans.

Frank added one more thing.

If all you know about Northwestern Mutual is a life insurance policy from years ago, maybe it’s time to go back for a second coffee!

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Why Milwaukee for Frank?

Frank looked at other cities before choosing Milwaukee. But he wanted to be somewhere he could make a real difference, fast.

This is a city where you can show up, get involved, and matter.

So, over the next few months, Frank and I will keep riffing on Milwaukee, business, tech, people, and coffee. Maybe even our take on our favorite whiskeys.

For now, take a listen below or on Spotify.

I guarantee you’ll be inspired about Milwaukee, your work, and how you spend your time in our city.

Love you, Milwaukee!

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• Bader Rutter is a 53 year old, Milwaukee based, business-to-business agency serving agriculture, food and beverage, manufacturing and more.

• Brian has worked for Bader Rutter for 15 years and originally launched the AI, Emerging Technology, and MarTech practice he leads.

• Over a 30 year career, Brian has worked in the marketing, data, and technology spaces from the early days of personalized direct mail to today’s multi-agent AI workflows.

If you’ve ever driven on Water Street in downtown Milwaukee, there’s a really good chance you’ve driven by Bader Rutter without knowing it.

I know. I’ve done it.

But on the day of my interview with Brian Kohlmann, Director of AI, Emerging Technology, and MarTech at Bader Rutter, I did not pass by. I successfully arrived at my destination.

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As I walked in, it looked more like a cafe for creative co-working than a B2B marketing agency. Residing in the building Laacke & Joys used to occupy, you get beautiful Milwaukee cream city brick along with matching views of Water Street and the riverfront.

Brian greeted me in the cafe. Then, we walked through the space to a room called the Library. To me, it was speakeasy meets thinking space, fully equipped with comfy furniture and tucked away from the hustle of the rest of the office.

And so thinking is what we did. And a lot of talking.

One swig of coffee and the conversation launched.

Even though he thinks a lot about AI in his daily work, Brian is totally anti-hype.

Every project at Bader Rutter starts with a business problem. The problem is what inspires and directs the do-we-have-something-already or do-we-build-something-new decision process.

For Brian, this process is kept intentionally simple.

Which, is refreshing for me.

Because I’ve been writing and talking about the executive AInxiety most of us are avoiding.

Brian sees this avoidance all the time and describes it like this.

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AI hype gets pushed down on leadership.

Which then gets pushed down to the team.

“Use AI!” For something. Anything. Cut costs. Personalize content. Go. Now.

In the midst of the scramble, everybody gets AInxious.

Nobody wants to pick the wrong direction or make the wrong investment.

Brian’s fix? Take a breath.

You see, Brian started in personalized direct mail. Back then, that was cutting edge magic. Today, he’s driving AI. Leading edge, but still just a tool.

Start with the problem, not the “magic.”

Is Milwaukee a place for tech?

We also shifted to this topic.

Brian’s answer to the question on Milwaukee’s tech scene: you betcha! And he adds, “come on in, the water’s fine!”

He’s worked in and with other places in other cities. What does he love most about working in tech in Milwaukee? The people.

Because he knows the AI hype will keep coming. And Brian will keep working with people, talking through the problems, and making decisions in the best interest of both.

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Brian and I get into all of this and more, in depth in the audio interview.

Take a listen below or on Spotify.

And let me know what you think about AInxiety in the comments.

Love you, Milwaukee.

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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.