Why Cream City Cyber Is Betting on Summerfest TechAI and on Milwaukee.
The duo behind one of Milwaukee's fastest-growing tech startups talks AI risk, the talent we keep exporting, and why people matter most.
Bios:
Celeste Cuffie, Chief People Officer and Co-founder, Cream City Cyber (photo by Robert Dodds)
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)
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)
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.
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.