This episode is part of our 2026 Summerfest TechAI series, sponsored by Cream City Cyber.

Steve's guests on this one include:

• Celeste Cuffie, Chief People Officer and Co-founder, Cream City Cyber
• Sheldon Cuffie, CEO & Co-founder, Cream City Cyber
• Lena DeLaet, Director of Sales & Summerfest TechAI

What you'll get:

• 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,

• They make the case that AI is moving at “light speed,” but the real risk isn’t the technology

• On the cybersecurity front, Sheldon warns that AI is becoming “a firecracker on top of a rocket ship”
• The conversation then turns to Milwaukee’s biggest challenge

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

In this episode, Steve talks with Mandela on his take on innovation, startups, AI accountability, and why Wisconsin has everything it needs to compete if we're willing to invest in it.

NOTE: This article is not an endorsement for Mandela Barnes. The purpose was to have a conversation about his vision for technology and innovation for the state. I have asked all eight Wisconsin gubernatorial candidates to join me on this platform for the same conversation and coverage.

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.

Guests Brooke Casazza and Michael Dairyko give an honest and interesting take on AI, data, and tech in sports.

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.

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.

In this one, Steve sits down with Kelda Roys for an informative discussion on Kelda's case that Wisconsin's economic future depends on.

About Kelda:

• 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.

About the episode:

• 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.

  Follow us on Substack: www.experiencemilwaukee.com

  Sponsored by SCS and Concurrencty.

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.

Jay 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.

In this episode, Jay 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 also get into one of the most uncomfortable but important tensions in the region’s tech ecosystem.

Sponsored by Concurrency and Secure Compliance Solutions.

This episode explains the evolution of Experience Milwaukee from a culture-focused podcast into a platform centered on business, tech, innovation, and the people shaping Milwaukee’s future, without losing sight of the city’s cultural fabric.

Steve shares more of his own story than he usually does, including how growing up with limited access to professional networks shaped his long-term mission: build connections and shorten the curve for others trying to grow their careers or companies in Milwaukee.

The conversation gets into why Milwaukee is both well-positioned and behind in tech: strong enterprise talent, strong big-company DNA, but not enough alignment, coordination, or shared direction to fully capitalize on that advantage.

Steve also lays out a more specific vision for where this could go next: an enterprise-led, Midwest-wide innovation movement that connects big companies, founders, and outside startups around real problems worth solving here.

Most of all, the episode sets up what you should expect from the refreshed Experience Milwaukee: more point of view, more honesty, more access to the leaders behind Milwaukee’s tech evolution, and more clarity on who ambitious people should know and why.

"In this episode, Steve sits down with Mark Fairbanks, Cofounder & Executive Director of Islands of Brilliance

Talking points include: Neurodiversity, Special Interest Focusing, Program Growth, and Trains!

Special thank you to local Milwaukee band Paper Valley for their track "Breakaway" - check them out at https://open.spotify.com/artist/4lsijeS7nxgLPGdqnsmmz4?si=f25NjrndTsO62Q-SuRYqnA

Episode edited by Stevie Salinas, Social Media & Content Director at Experience Milwaukee"

In this episode, Steve and Adam sit down with Charlie Connelly, Manager of Corporate Partnerships & Fulfillment for your Milwaukee Admirals.

Talking points include: Cortados, Collaboration, Coaching Sports, and Crappy Gifts!

Special thank you to local Milwaukee band Paper Valley for their track "Breakaway" - check them out at https://open.spotify.com/artist/4lsijeS7nxgLPGdqnsmmz4?si=jYdWejRQTXuosgy2TO9L2g

Episode edited by Stevie Salinas, Social Media & Content Director at Experience Milwaukee

In this episode, Steve sits down with Jockey President and Chief Operating Officer, Mark Fedyk.

Recorded live at the brand-new Kenosha Innovation Neighborhood, this episode delivers an inspiring look at how one of Wisconsin’s long standing brands continues to innovate like a startup.

Mark breaks down how Jockey defines innovation—not just as a process, but as a mindset woven into its nearly 150-year DNA.

From “routine” updates to “disruptive” and even radical innovation, the company keeps close to its customers through data, insights, and an enduring human touch.

We also learn that through connection to community, legacy and innovation can coexist.

The conversation is both humorous yet insightful, exploring how a heritage brand stays fresh, relevant, and ready for what’s next.

Experience Milwaukee is presented by Habush Habush & Rottier, VISIT Milwaukee, the Milwaukee Admirals, nvisia, Summerfest, and Crescent 9 THC Seltzers and our official beer partner is New Barons Brewing Cooperative.

Thanks for listening.

Love you, Milwaukee.

In this episode, Steve and Adam dive into one of Milwaukee's most beloved annual traditions - Doors Open Milwaukee - celebrating its 15th anniversary this September 27th and 28th.

They're joined by Grace from Historic Milwaukee, who coordinates this incredible event that opens more than 150 locations across the city for free public tours, from private clubs like the Wisconsin Club to neighborhood gems you'd never normally see inside.

They also chat with Jeff from Milwaukee Fashion Week about how their fashion showcase is partnering with Doors Open at City Hall's rotunda, and CK from Villa Arco, the stunning former funeral home turned event space and art gallery.

Whether you're interested in historic architecture, local fashion, or discovering the hidden stories behind Milwaukee's most intriguing buildings, this episode has something for everyone ready to explore our city.

For more information on Doors Open Milwaukee: https://historicmilwaukee.org/doors-open

Experience Milwaukee is presented by Habush Habush & Rottier, VISIT Milwaukee, the Milwaukee Admirals, nvisia, Summerfest, and Crescent 9 THC Seltzers and our official beer partner is New Barons Brewing Cooperative.

Thanks for listening.

Love you, Milwaukee.

John DenBoer grew up in Waukesha raised by his mom and grandmother, which sparked his lifelong passion for working with older adults - he eventually became a geriatric neuropsychologist specializing in detecting dementia way before symptoms show up.

After studying at places like Harvard and building a successful digital health company out west, he and his wife decided to make Milwaukee home (funny how he had to move to Phoenix to meet someone from down the road!).

Now he's launching a venture studio to find and support game-changing technologies to tackle big problems - think dementia, farm tech, water, and more. Which really hits home here in Wisconsin.

This podcast series is going to follow John and his team as they build the venture studio from the ground up, working with some heavy hitters in the Milwaukee startup scene.