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IT HootClub — AI Community Newsletter

Hands-on. Career-focused. Future-ready.
Issued 2026-06-06

Building the Arena

Building the venue before the model showdown: a model catalog to pick the contender, and the groundwork for a verified Milwaukee inventory.

Announcements

New on hardais.com: A Model Catalog

There are an absurd number of AI models out there, more landing every week, and the question that actually matters — which one can I use for this? — is buried under marketing and leaderboards that all measure slightly different things. So I built a catalog to cut through it. Describe what you need in plain English — say, “an open-weight model good at legal summarization” — and it returns only models that are actually in the catalog, ranked, with the reason each one matched. Never an invented model, never a made-up spec. And you can still browse and compare them directly by the attributes that decide whether one fits a real project.

Each entry lays out the things you’d otherwise have to dig for — who made it, how big it is and what that implies for running it, how much context it can hold, whether the weights are open or closed, what the license allows commercially, and a plain-language summary of what it’s actually good at — with a short editorial take and comparable models alongside. Technical terms in the writeups are wrapped with plain-English definitions you can hover for, so the explanation comes to you instead of sending you off to look it up.

It’s an early version and I’ll keep filling and refining it, but it’s live and usable now. Regular readers will recognize the bigger reason it exists: this is the tool I’ll use to pick the model that goes into the Milwaukee assistant build — the contender, in this week’s Building Intelligence terms. Have a look and tell me what’s missing.

Browse the model catalog →

Building Intelligence

Building the Arena

This series has been pointing at a showdown for months now: a small, purpose-built Milwaukee tech assistant going up against the big general-purpose models with web search, judged head-to-head on a fixed rubric. That’s the whole bet — that something narrow and carefully fed can beat something vast and generic on its home turf. This week was not the fight. It was building the place the fight happens. You don’t stage a contest without a venue, and the venue didn’t exist yet.

So I spent the week on the website. hardais.com is where this model will eventually live — not a slide about a model, an actual thing you can query — and a fair showdown needs three things that weren’t there a week ago: a contender to put in the ring, a ground truth to judge its answers against, and a place to hold the whole thing. I made progress on the first two.

The contender first. You can’t put “an AI” in a ring — you have to pick a specific model, and there are a staggering number to pick from, with new ones landing weekly. So I built a model catalog: a search-and-compare feature for narrowing the field down to a model I can actually work with. That last part matters, because “best in general” and “best for what I’m doing” are different questions — I need one I can run, shape, and afford, not just one that tops a leaderboard. It launched this week and it’s in the Announcements above; consider it the tool I’ll use to choose the fighter.

The ground truth is the Milwaukee inventory — the database the assistant will draw from. Last week’s edition was about the hardest part of that: deciding what doesn’t go in, and building a schema that enforces the discipline instead of leaving it in my head. With that structure finally locked, this week it became easy to build a friendly way to actually fill it — and that turned out to be a small lesson in its own right, which is this week’s Under the Hood. The short version: getting the rigorous part right first is exactly what made the easy part easy.

But “fill it” doesn’t mean scrape the web and dump it in. The entire premise is that nothing goes in unverified, and a lot of what makes a community real isn’t published anywhere — it lives in the heads of the people running it. So this week I put correspondence out to several players in the Milwaukee tech scene, asking something more specific than “can I list you”: would they consent to being a source — someone I can point to when I claim a fact is true. That’s why the database carries consent flags on people and a paper trail on every source: a ground truth made of real Milwaukee folks who said yes is a very different thing from a list I assembled by guessing. The letters are out. I’m waiting to hear back, and I won’t pretend the inbox is full yet.

So that’s the honest state of things: the arena is going up, but the bell hasn’t rung. The contender-selection tool is live, the ground truth has a structure and its first real outreach, and the place it all lives is taking shape. The actual test — the model against the baselines, scored — only means anything once the venue is real, and the venue gets built before the fight, not during it. Next week tells me whether the inventory starts filling with real, consented, sourced organizations. Until then: the stage, not the show.

Under the Hood

Letting an AI Build the Front Door

Building Intelligence this week made a claim in passing: that getting the rigorous part right first is what made the easy part easy. This is the easy part. With the inventory’s structure finally locked, I needed a way to actually put organizations into it — and I let an AI build that for me in an afternoon. The interesting thing isn’t that I did it fast. It’s why doing it fast and loose was a safe choice rather than a reckless one.

Start with how data actually gets into a database. The commands that talk to a database come in two flavors, and both have names worth knowing. DDL — Data Definition Language — is the set of commands that define the structure: “create a table called organizations, give it these columns.” That’s the work I did last week building the schema. DML — Data Manipulation Language — is the set that handles the contents: “insert a row, put this name here, this website here.” Filling the inventory is a DML job. The old-fashioned way to do it is to hand-type those DML commands one organization at a time — which works, but it’s tedious and unforgiving: one fumbled line and you’ve quietly entered a broken or half-filled row. The friendlier way is a GUI — a graphical user interface, which just means a screen with labeled boxes and dropdown menus where you fill in a form, click Save, and something else writes the DML for you. I wanted the form. So I vibe-coded it: I described what I wanted in plain English to an AI, it wrote the code, and I shaped it by reaction — “make that a dropdown,” “move that field” — instead of writing a line of it myself.

Here’s why that should make you nervous, in general. Vibe coding produces something that looks right very quickly, and “looks right” is exactly the trap — an AI will confidently generate code that does something subtly wrong, and you may not notice until the damage is done. Pointing that loosely-built tool straight at the database that’s supposed to be my trustworthy source of truth sounds like a great way to fill it with quiet garbage.

It isn’t, and the reason is last week’s work. The rigor doesn’t live in the form — it lives in the database underneath it. All those rules I built into the schema (a field that can’t be left blank, an entry that has to point at a real cited source, a switch that defaults to “no” until a human says otherwise) are enforced by the database itself, no matter what hands it the data. The form is just a messenger. If the vibe-coded GUI tries to save something that breaks one of those rules, the database refuses it and hands back an error. The guardrails are in the foundation, so the convenience layer bolted on top is allowed to be casual — it physically cannot write a row the structure forbids.

And the structure didn’t just permit the form — it shaped it into something that nudges me toward clean data by default. Because the database already defines the fixed set of, say, allowed source types, the GUI can read that list and turn it into a dropdown automatically: I’m picking from known options, not free-typing “website” one day and “web site” the next and creating two things where there’s one. It puts the “raw, as-found” description and the “human-approved” description in two separate boxes, so the act of curating is built into the act of entering. The form is good not because the AI is clever, but because the schema gave it a clean shape to fill.

So here’s the lesson, and it cuts against how vibe coding usually gets sold. It’s pitched as a way to skip the hard part. What actually happened is the opposite: the hard part is the only reason the shortcut was safe. I did the slow, careful structural thinking where it counted — the schema, the rules, the defaults — and that’s precisely what earned me the right to be fast and loose on the layer where it didn’t. Schema before code, I’ve said before. This is the “before code” part paying off: the front door’s built, it can’t let anything ugly through, and now the only thing left is to walk the real organizations in.

The Learning Loop

DEFINITION Backpropagation
Backpropagation is a technique used in artificial neural networks to improve model performance, involving adjusting weights based on the error rate of predictions compared to the actual values.
Source: Wikipedia
TIP Progressive Elaboration
When tackling complex tasks, gradually expand on the details in your prompt as the AI progresses through each iteration, refining outputs with each step.
Source: ProductiveAI
TOOL PromptPerfect
PromptPerfect is an advanced tool designed to help optimize prompts for large language models by providing performance analytics and suggestions for refinement.
Source: https://promptperfect.io

Lift-Off

“Curiosity is the engine of achievement.”

— Ken Robinson — Ken Robinson was a British author, speaker, and international advisor on education in the arts to government, non-profits, education, and arts bodies. He is best known for his work on promoting creativity and innovation in education. Robinson was a professor emeritus at the University of Warwick in the UK and was knighted for his contributions to the arts.

The Nest Jest

Why do AI models struggle with relationships? They can never truly understand human data.

Upcoming Events

Event 06/08/2026 6:00 PM
(Hybrid) Random Testing with ‘Fuzz’: 35 Years of Finding Bugs — Online (Madison Central Public Library, 201 West Mifflin St. Room 302, Madison, WI)
online: https://youtube.com/live/DTOTDmrAjq4?feature=share Fuzz testing has passed its 35th birthday and, in that time, has gone from a disparaged and mocked technique to one that is the foundation of many efforts in software engineering and testing. The key idea behind fuzz testing is using random input and having an extremely simple test oracle that only looks for crashes or hangs in the program. Importantly, in all our studies, all our tools, test data, and results were made public so that o [Group: madison-ai]
Source: https://www.meetup.com/madison-ai/events/314652025/
Event 06/09/2026 7:00 PM
Superintelligent AI and Loss of Control | Virtual Workshop Series — Online (Online event)
​**A free, public workshop—no technical background needed** ​What would it actually mean for machines to become smarter than humans—not just at chess or writing, but at *everything*? For decades, scientists and researchers have debated the idea of Superintelligent AI: systems that could outperform humans across nearly all cognitive tasks. What once sounded like distant science fiction is now increasingly discussed as a real possibility within our lifetimes. ​This workshop is a guided, interactiv [Group: ai-safety-awareness-group-milwaukee]
Source: https://www.meetup.com/ai-safety-awareness-group-milwaukee/events/315021276/
Event 06/09/2026 6:00 PM
Milwaukee Bitcoin Summer Cruise — Edelweiss Highland Ave. Dock 205 W. Highland Ave. Milwaukee, WI
We’ll be hopping aboard the Edelweiss Fiesta Cruise for an evening of conversation, community, tacos, drinks, and summer lakefront views.
Source: https://www.meetup.com/milwaukee-wisconsin-bitcoin-meetup/events/314097541/?eventOrigin=group_similar_events
Event 06/10/2026 5:15 PM
Global AI Milwaukee June Meetup — Online (Milwaukee, WI)
TBD [Group: global-ai_milwaukee]
Source: https://www.meetup.com/global-ai_milwaukee/events/314771448/
Event 06/10/2026 5:30 pm
June Code + Brews — Magik4GamingHub 2222 N. Farwell Ave. Milwaukee, WI 53202
We are excited to invite you to our upcoming networking and coding event. This gathering is designed to foster connections within our local tech community. Whether you are a seasoned professional, a hobbyist, or just getting your feet wet in the world of coding, there's a place for you here.
Source: https://www.meetup.com/mitobyte/events/312261400/?eventOrigin=group_similar_events
Event 06/11/2026 7:00 PM
Intro to AI Evaluations |Virtual Workshop Series — Online (Online event)
**A free, public workshop—no technical background needed** ​AI systems can now write code, imitate human conversation, strategize, and even deceive. But despite how often we use these tools, most people still have no idea how they actually work—or how researchers test whether they’re safe. ​This workshop pulls back the curtain on modern AI systems and explores the emerging field of AI evaluations (“evals”): the methods researchers use to measure what these models are capable of, where they fail, [Group: ai-safety-awareness-group-milwaukee]
Source: https://www.meetup.com/ai-safety-awareness-group-milwaukee/events/315046646/
Event 06/13/2026 10:00 AM
MadAI Hackathon - AI Code Jam — Online (Madison, WI)
Join us for a day of augmented development and prompt engineering. Whether you are looking to accelerate a side project, learn the nuances of LLMs, or just see how fast you can break an agent, this is your space. This is a 5-hour collaborative working session designed to get you out of "tutorial hell" and into building mode with the help of AI. The Plan: This isn't a classroom. It's a lab. Bring your laptop and your current obsession. We are focusing on: * AI-Assisted Build: exploring how tools [Group: madison-ai]
Source: https://www.meetup.com/madison-ai/events/315011107/
Event 06/16/2026 7:00 PM
Data and Privacy in the Age of AI | Virtual Workshop Series — Online (Online event)
**A free, public workshop—no technical background needed** ​Most of us already know that companies, governments, and apps collect a lot of data about us. That part isn’t new. ​**What *is* new is what AI makes possible with that data.** ​For years, the privacy conversation has mostly been about tracking, ads, data brokers, social media, and surveillance. Those concerns still matter. But advanced AI changes the picture: once powerful models can analyze huge amounts of text, images, location data, [Group: ai-safety-awareness-group-milwaukee]
Source: https://www.meetup.com/ai-safety-awareness-group-milwaukee/events/315046737/
Event 06/18/2026 7:00 PM
AI Policy and Governance Overview | Virtual Workshop Series — Online (Online event)
**A free, public workshop—no technical background needed** ​AI is moving fast. The companies building it are moving fast. Governments are trying to respond, but most people still don’t have a clear picture of what is actually happening or what good policy would even look like. ​This workshop is meant to give people that bigger picture. ​We’ll start with a quick, plain-English overview of what AI is as a technology, how today’s systems work at a high level, and why the last few years have felt so [Group: ai-safety-awareness-group-milwaukee]
Source: https://www.meetup.com/ai-safety-awareness-group-milwaukee/events/315046819/
Event 07/24/2026 10:00 AM
Hands-On : Copilot Studio, Microsoft Fabric, Azure AI : Better Together — Online (Online event)
**Hands-On Online Workshop: Copilot Studio, Microsoft Fabric, Azure AI : Better Together** **Date: 24 July 2026, 10 AM to 5 PM Eastern Time** **Level: Beginners/Intermediate** **Registration Link:** https://www.eventbrite.com/e/hands-on-copilot-studio-microsoft-fabric-azure-ai-better-together-tickets-1983680029367?aff=oddtdtcreator **Who Should Attend?** This hands-on workshop is open to developers, senior software engineers, IT pros, architects, IT managers, citizen developers, technology pro [Group: artificialintelligenceandmachinelearning]
Source: https://www.meetup.com/artificialintelligenceandmachinelearning/events/313897285/
Event 07/29/2026 09:00 AM
Founders Day — Ward4, 313 N Plankinton Avenue, Milwaukee, WI 53203
Monthly networking and programming for Milwaukee's startup and technology community, hosted by MKE Tech Hub Coalition at Ward4. Recurring last Wednesday of the month.
Source: MKE Tech Hub Coalition (mketech.org)

In the News

News 2026-06-07TechCrunch
OpenAI unveils Lockdown Mode to protect sensitive data from prompt injection attacks
OpenAI has introduced a new feature called Lockdown Mode aimed at mitigating the risk of prompt injection attacks that could inadvertently expose sensitive data during interactions with AI models like ChatGPT. Although the mode does not completely eliminate threats, it is designed to reduce the likelihood of data leakage. This new addition underscores OpenAI’s commitment to advancing the security framework surrounding its AI technologies. read more
News 2026-06-07VentureBeat
Salesforce rolls out new Slackbot AI agent as it battles Microsoft and Google in workplace AI
Salesforce has launched a fully revamped Slackbot AI agent, transforming it from a simple notification tool into an advanced enterprise assistant capable of searching data, drafting documents, and executing actions for employees. This move signifies Salesforce's strategic push to enhance its AI capabilities amid stiff competition from Microsoft and Google in the workplace technology arena. The upgraded Slackbot aims to offer a sophisticated digital assistant experience for business users. read more
News 2026-06-07WIRED
OpenAI and Anthropic May Be Rivals, but Investors Aren’t Picking Sides
Despite ongoing rivalry in AI innovations between OpenAI and Anthropic, investors are showing interest in supporting both companies rather than choosing one. This dual support from investors highlights the confidence in both firms' potential to lead advancements in AI technology. The strategy of diversified investment mirrors the approach of backing competitive yet promising entities to maximize returns in the evolving AI industry. read more

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