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IT HootClub — AI Community Newsletter

Hands-on. Career-focused. Future-ready.
Issued 2026-05-21

The Schema Becomes Real

Building Intelligence Week 7: the inventory schema stands up as a real Postgres database on Neon. Plus a Rabbit Hole on OpenClaw and the due-diligence questions an introduction isn't responsible for answering.

Announcements

A note that came to the HootClub directly: Clayton Custer of gener8tor reached out to invite our community to the gALPHA program kicking off at WCTC's Applied AI Lab. I'm passing it along because it's a genuinely good fit for the people who read this — and because the registration window is short.

Register by Saturday, May 30 — the program begins Monday, June 1.

gALPHA is a free, four-week venture-creation workshop run by gener8tor (a nationally ranked startup accelerator) and sponsored by WCTC. The Applied AI Lab version takes a "back to basics" approach to building a business, but with AI woven through every stage — using generative tools to rethink the business model canvas, validate ideas, prototype with no-code workflow tools, and pitch. No prior AI experience is required, and it's open to anyone in the Greater Waukesha area, not just WCTC students.

What the four weeks cover:

The format is a weekly Monday Lunch & Learn (streamable over Zoom), Wednesday-evening group collaboration sessions, and flexible one-on-one coaching. Throughout, teams take on an AI Workflow Challenge — build an AI-enabled workflow that improves your business, pitch it at the showcase, and the best one wins six months (or $300) of a free AI service, sponsored by gener8tor.

If you've been sitting on an idea, this is a low-cost, high-support way to actually move on it — and a good chance to meet other technologists in the area. I'd encourage you to take a look.

Apply: gener8tor.com/galpha/applied-ai-lab  ·  Contact: Clayton Custer, Program Manager, clayton.custer@gener8tor.com

Building Intelligence

Last week I drew the schema — six core entities, the junction tables between them, the rules each one encodes. It was a plan. A diagram. Something that existed in dbdiagram.io and in my head, but nowhere a row of real data could ever land. This week it became real. The schema is now a Postgres database, the tables exist, and they are sitting there empty, waiting for Milwaukee.

That's the whole milestone, and I want to be honest that it's a small one on purpose. I didn't load any data. I didn't pick a model. I didn't write a single line of the code that will eventually fill these tables. I translated the design into a real structure and confirmed it holds together — the order of operations this series keeps insisting on: schema before code before content. The structure exists now. Next week it starts to fill.

But standing it up surfaced a question I didn't expect, and it's the more interesting story. The database lives on Neon — managed Postgres that my hardais.com site already connects to. When I went to create it, I found I already had a Neon project there: hardais-catalog, the database behind a LLM catalog the site is intending to offer, where visitors search and sort information about language models. That stopped me. Because the thing I'm building — a searchable, sortable inventory of entities with relationships and provenance — is also a catalog. And the site already has a lab where you can ask a question of a model that uses vector-based retrieval versus one that doesn't, which is almost exactly what this whole series is demonstrating. (The components themselves — Neon, Postgres, the migration tools, pgvector — get the full what-and-why treatment in Under the Hood this week, if you want to go a level deeper.)

So the question wasn't "where do I put this." It was something bigger: is this build a separate thing, or is it the prototype for how all of my catalogs should eventually work? The LLM catalog, the retrieval lab, the visitor chat that will someday want a real knowledge base — they're all variations on the same shape this Milwaukee inventory is taking. I'm not answering that yet. I built the inventory in its own clean, separate Neon project for now, which keeps the work isolated and keeps every door open. But I'm flagging it out loud, because it's the kind of realization that only shows up once you stop drawing and start building.

Next week is the one I've been pointing at for a while: getting the data. The structure is built. Now comes the hard, honest part — filling it with real Milwaukee tech organizations, events, and people, with sources attached and the right level of verification for each. That's where this stops being architecture and starts being an answer to the question that started it all.

Under the Hood

Last week's Under the Hood described a stack I was going to use: Postgres running in a Docker container on my machine, verified with a tool called DBeaver. When I actually sat down to build it, I used neither. That's not a reversal — it's what happens when an abstract plan meets a real environment, and the reasoning behind each cut is worth more than the original plan was. So here's the stack I actually built on, what each piece is, and why two of last week's pieces turned out to be solving problems I don't have.

Postgres, and where it actually lives

The foundation is PostgreSQL — the relational database the whole design assumes. That part didn't change. What changed is where it runs, and there's a common misconception buried in here worth clearing up. I'd been thinking of the database as "hosted on Vercel," because hardais.com runs on Vercel. That's not how it works. Vercel hosts the website — the front end and the small server functions behind it — but Vercel does not run a database. Instead, the site connects to a database that lives somewhere else, over a connection string. That somewhere else, for me, is Neon: a managed Postgres provider built to pair with exactly this kind of setup. Managed simply means I don't run or patch the database server myself — Neon does — and I get a connection string the site (and my build) point at. Same Postgres, just run for me instead of by me.

Why I dropped Docker

Docker is a tool for packaging software — here, a Postgres database plus its exact version and settings — into a self-contained "container" that runs identically on any machine. Last week I planned to run Postgres in a Docker container locally. The reason I dropped it is clarifying: Docker's whole value is making a local environment reproducible and portable. But I'm building directly against Neon, where the database already exists and is already reproducible — that's what managed hosting is. There's no local environment for Docker to package, so Docker would be ceremony, not substance. And if I ever did want to work locally, I already have Postgres installed on my machine; I'd build there and copy the result up to Neon, still never needing the container layer. Docker is a genuinely good tool. It was just answering a question my setup doesn't ask.

How the schema actually got built: ORMs and migrations

The design lived in a .dbml file — the text version of last week's diagram. Turning that into real tables is the job of two tools that work together. The first is SQLAlchemy, an ORM — Object-Relational Mapper. An ORM lets me describe database tables as objects in Python code instead of writing raw SQL by hand; it's the translation layer between "code I write" and "tables the database understands." The second is Alembic, which handles migrations. A migration is a versioned, recorded change to the database structure — "add this table, this column, this relationship" — saved as a file you can review, replay, and roll back. The principle is the one that runs through this whole project: schema changes deserve version control just like code does. You don't quietly edit a database and hope you remember what you did. You write the change down, run it, and have a record. That's how the six entities and their junctions went from a diagram into a structure that exists.

Why I dropped DBeaver too

DBeaver is a database tool that can, among other things, render an entity-relationship diagram from a live database, and last week I'd planned to use it to verify the schema. Dropping it was an honest redundant-tool call. I'd already built and rendered the ERD in dbdiagram.io, which served that purpose, and the migration running cleanly is what actually confirms the tables match the design. DBeaver may be a bit more robust, but it would just produce a second picture of something I'd already verified — so it's no longer needed.

The piece I deliberately did not build: pgvector

pgvector is a Postgres extension that lets the database store and search embeddings — the numerical representations of text that make semantic, meaning-based retrieval (the "RAG" in retrieval-augmented generation) possible. It is going to matter. Not someday in the abstract: three things on my site already point straight at it — the LLM catalog, the retrieval lab that demonstrates RAG-versus-no-RAG, and the visitor chat that will eventually want a real knowledge base — and the Milwaukee inventory will want it too. So why didn't I build it now? Because there is nothing to embed yet. Embeddings are for text that exists, and right now the tables are empty. Standing up vector search this week would be building a tool with nothing to point it at.

This is what forethought actually looks like, and it's the reason the foundation choices matter. pgvector isn't a separate system I'd have to bolt on later — it's an extension you enable with a single command, CREATE EXTENSION vector;, on the Postgres database I already have. Choosing managed Postgres on Neon now means the vector piece is one migration away when there's finally data to embed, not a re-platform. I'm not provisioning it prematurely. I'm provisioning the ground it will stand on, and leaving the rest for the week it's actually needed — which, fittingly, is the week the data starts arriving.

The Rabbit Hole

A while back, a talk at a local meetup introduced me to OpenClaw — a self-hosted platform for running an AI agent you can message from chat apps. It was a genuinely useful introduction, and it did what a good introduction does: it left me with questions. Specifically, the questions I'd want answered before putting something like this anywhere near real work. So I went and researched them. This is the conversation that came out of it — the due-diligence layer an introduction isn't responsible for providing.

Q: OpenClaw is "self-hosted." Doesn't that mean my data stays private — nothing leaves my machine?

A: This was the first thing I had to get precise about, because "self-hosted" is true but narrower than it sounds. What's self-hosted is the orchestration — the gateway process, the routing, the session history, the tool execution. That all runs on your hardware. But the thinking happens wherever the model lives. If you point OpenClaw at a frontier model like GPT or Claude, every prompt still gets sent to that provider's servers — and in an agent setup, "the prompt" isn't just your message. It's your message plus whatever the agent's tools pulled in to answer it: files it read, command output it captured, pages it fetched. So the data crossing the boundary can actually be larger than a normal chatbot query. Self-hosting the gateway doesn't change that one bit. The only configuration where data genuinely never leaves is when the model itself runs locally too. "Self-hosted gateway" and "private inference" are two different claims, and only the second one is about where your data goes.

Q: Fine — but I can lock it down so only I can message it. Doesn't that close the security problem?

A: It closes one door, and it's an important one. You can absolutely configure OpenClaw so only you can send it messages — allowlists, pairing for unknown senders, all of it. That stops a stranger from instructing the agent directly. But here's the distinction that took me a minute to see clearly: controlling who can message it is not the same as controlling what it reads while working. The moment you ask it to do something useful — "summarize this thread," "check this repo's issues," "read this page" — the agent ingests content written by people who aren't on your allowlist. And if that content contains hidden instructions, the agent encounters them regardless of how tightly you locked the front door. This is prompt injection, and the unsettling part is it doesn't need a malicious sender. It rides in on the very material you asked the agent to look at. The allowlist guards the request. It does nothing to guard the material the request pulls in.

Q: Isn't this the same risk as any AI coding tool? Why single out OpenClaw?

A: The injection vector is the same — any agent that reads outside content can be fed a hidden instruction, and that includes the everyday tools many of us already use. So no, OpenClaw isn't uniquely dangerous in kind. Where it differs is degree, along three axes. First, attendance: an interactive tool acts while you're watching and you can stop a weird step; OpenClaw is designed to run unattended, on a schedule, so the same bad step can land at 3 a.m. with no one in the loop. Second, the inbound channel: connecting it to messaging apps expands who could put content in front of it from "things I chose to open" to "anyone who can reach the channel." Third, standing access: it's a persistent process holding standing credentials, not a session that ends when you close the laptop. None of these is a flaw to patch.

Q: So what's the actual takeaway — is it safe to use or not?

A: The takeaway is the thing that reframed it for me, and it's not "safe" or "unsafe." It's that the features being sold are the same features that carry the risk. Unattended operation, inbound chat channels, standing autonomous access — those three things are exactly why OpenClaw is appealing, and they're exactly the three things that turn an ordinary injection risk into a serious one. You can't keep the appeal and engineer the risk away separately, because they're the same property. That doesn't mean don't use it. It means the right question isn't "is it secure" — it's "what is the worst thing this agent could do if it were turned against me, and have I made that worst case survivable?" The defenses that actually matter follow from that: run the model locally if your data can't leave, give the agent its own scoped credentials rather than your real ones, keep it away from anything you can't afford to lose, and treat everything it reads as potentially hostile. The platform can be configured responsibly. But it's the kind of tool where you have to decide the posture deliberately, because the convenient default and the safe default are not the same default.

None of this is a knock on OpenClaw or on the talk that pointed me toward it — both did exactly what they were supposed to. The lesson I came away with is bigger than one platform: as agents move from "tool you invoke" to "service that runs," the interesting questions stop being about capability and start being about blast radius. What can it reach, who can steer it, and what happens if it's wrong. Those are the questions worth asking before you adopt any of this — and they're the ones an enthusiastic introduction will rarely answer for you.

The Learning Loop

DEFINITION Quantization
Quantization is the process of converting an AI model's high-precision numerical values into lower-precision formats (such as 8-bit integers) to significantly reduce the model's size and increase its processing speed on standard hardware.
Source: https://huggingface.co/docs/optimum/concept_guides/quantization
TIP XML Tagging
Wrap different components of your prompt in XML-style tags (e.g., , , or ) to provide a clear hierarchy that helps the AI distinguish between your commands and the data it needs to process.
Source: https://docs.anthropic.com/en/docs/build-with-claude/prompt-engineering/use-xml-tags
TOOL Consensus
Consensus is an AI-powered search engine that finds answers to questions directly from peer-reviewed scientific research papers, providing evidence-based summaries and direct citations for every claim.
Source: https://consensus.app

Lift-Off

“There is no doubt that the best technique is the one which is not noticeable.”

— Satyajit Ray — He was an Indian filmmaker, screenwriter, and author widely regarded as one of the greatest auteurs in cinema history. He received an Academy Honorary Award in 1992 for his profound influence on the art of motion pictures. His work often focused on the humanistic details of daily life and utilized a masterful economy of storytelling.

The Nest Jest

Why did the AI skip the party? It didn't want to overfit.

Upcoming Events

Event 05/21/2026 7:00 PM
Intro to AI Evals (non-technical) | Virtual — 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 th [Group: ai-safety-awareness-group-milwaukee]
Source: https://www.meetup.com/ai-safety-awareness-group-milwaukee/events/314870893/
Event 05/26/2026 9:00 AM
Cisco CCNA Training & Certification Program in Milwaukee, WI — 1433 N Water St, Milwaukee, WI
Get CCNA 200-301 certified with hands-on Cisco labs, expert-led training, real-world networking skills, and career guidance.
Source: https://www.eventbrite.com/e/cisco-ccna-training-certification-program-in-milwaukee-wi-tickets-1982985891181
Event 05/27/2026 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)
Event 05/27/2026 6:00 PM
Reasoning for Complex Data through Self-Supervised Learning — Online (Madison Central Public Library, 201 West Mifflin St. Room 302, Madison, WI)
*** Self-supervised learning deals with problems that have little or no available labeled data. Recent work has shown impressive results when underlying classes have significant semantic differences. We will discuss strategies to tackle to enable learning from unlabeled data even when samples from different classes are not prominently diverse. We approach the problem by leveraging novel ensemble-based clustering strategies where clusters derived from different configurations are combined to gen [Group: madison-ai]
Source: https://www.meetup.com/madison-ai/events/314652384/
Event 05/27/2026 9:00 AM
PMI-CPMAI Certification Training – 3-Day Bootcamp in Milwaukee, WI — 1433 N Water St, Milwaukee, WI
Master AI in Project Management & project in AI concepts with PMI-CPMAI™. 4-day training, real use cases & exam prep.
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Event 06/02/2026 9:00 AM
Machine Learning & AI Essentials 2 Days Training – Milwaukee, WI — For venue information, Please contact us: info@skelora.com, Milwaukee, WI, WI
Learn AI & ML fundamentals with practical insights, real-world use cases, and hands-on concepts to boost your career. By Skelora Edu Tech.
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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 9:00 AM
Become AI Project Ready – PMI-CPMAI Training Program in Milwaukee, WI — 1433 N Water St, Milwaukee, WI
Gain in-demand skills in Project in AI with this 3-day PMI-CPMAI® training. Learn to manage AI projects, align business goals.
Source: https://www.eventbrite.com/e/become-ai-project-ready-pmi-cpmai-training-program-in-milwaukee-wi-tickets-1986350283168
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 06/12/2026 5:00 PM
AI Specialists: Supercharge Your Career with AIConnect Networking! - Milwaukee — Location TBD; Register Online, Milwaukee, WI
Experience specialists supercharge networking in Milwaukee on 12 Jun 2026, 5 PM CDT. Connect with professionals!
Source: https://www.eventbrite.com/e/ai-specialists-supercharge-your-career-with-aiconnect-networking-milwaukee-tickets-1989002793899
Event 06/15/2026 6:00 PM
Using AI Wisely: Tips for Everyday Decisions — Antioch Public Library District, Antioch, IL
Get smart about using AI in your daily life with easy tips that actually make decisions simpler and better.
Source: https://www.eventbrite.com/e/using-ai-wisely-tips-for-everyday-decisions-tickets-1988633612668
Event 06/16/2026 9:00 AM
4-Day Data Science with Python Bootcamp in Milwaukee, WI — 1433 N Water St, Milwaukee, WI
Join our 4-Day Data Science with Python bootcamp! Learn data analysis, ML basics, and work on real-world projects.
Source: https://www.eventbrite.com/e/4-day-data-science-with-python-bootcamp-in-milwaukee-wi-tickets-1985353840782
Event 06/17/2026 5:00 PM
AI Specialists: AgenticAI Career Catalyst - Connect & Grow! - Milwaukee — Location TBD; Register Online, Milwaukee, WI
Don't miss specialists agenticai networking in Milwaukee on 17 Jun 2026, 5 PM CDT. Connect with professionals!
Source: https://www.eventbrite.com/e/ai-specialists-agenticai-career-catalyst-connect-grow-milwaukee-tickets-1989905503929
Event 06/19/2026 9:00 AM
Artificial Intelligence & Automation 1 Day Workshop |Milwaukee, WI — For venue details reach us at info@learnerring.com, Milwaukee, WI
Understand AI, Automation & Real-World Business Applications | Hands-On | Beginner to Intermediate
Source: https://www.eventbrite.com/e/artificial-intelligence-automation-1-day-workshop-milwaukee-wi-tickets-1980168783135
Event 06/20/2026 9:00 AM
PMI-CPMAI® Weekend Training – Project in AI Certification in Milwaukee, WI — 1433 N Water St, Milwaukee, WI
Join our PMI-CPMAI® weekend training and master Project in AI. Learn AI project lifecycle, data strategy, and real-world implementation.
Source: https://www.eventbrite.com/e/pmi-cpmai-weekend-training-project-in-ai-certification-in-milwaukee-wi-tickets-1986052225670
Event 06/20/2026 11:00 AM
Know Your Money 2.0 — Powered by AI — Milwaukee Central Library, Milwaukee, WI
7 expert speakers. Free lunch. 3 hours. Open to all Wisconsin residents. In-person at Milwaukee Public Library + virtual. Saturday, June 20.
Source: https://www.eventbrite.com/e/know-your-money-20-powered-by-ai-tickets-1989964513428
Event 06/20/2026 9:00 AM
PMI-CPMAI® Weekend Training –Project in AI Certification in Kenosha, WI — 100 N Atkinson Rd, Grayslake, IL
Join our PMI-CPMAI® weekend training and master Project in AI. Learn AI project lifecycle, data strategy, and real-world implementation.
Source: https://www.eventbrite.com/e/pmi-cpmai-weekend-training-project-in-ai-certification-in-kenosha-wi-tickets-1986115976350
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 2026-05-21VentureBeat
Google just redesigned the search box for the first time in 25 years — here’s why it matters more than you think.
At its annual I/O developer conference, Google announced a sweeping redesign of its iconic search box to retire the 25-year-old traditional interface. The update integrates AI-centric features directly into the search experience, moving away from the classic "list of blue links." This shift marks a fundamental change in how the company intends for users to interact with information through generative AI. read more
News 2026-05-21TechCrunch
Hark raises $700M Series A for its secretive “universal” AI interface
AI startup Hark has secured $700 million in Series A funding, bringing the company’s valuation to $6 billion. Founded by Brett Adcock, the firm is developing a secretive "universal" AI interface aimed at transforming human-computer interaction. The massive investment highlights the continued high demand for foundational AI technology and innovative user interfaces. read more
News 2026-05-21TechCrunch
The Path, founded by Tony Robbins and Calm alums, hopes to offer safer AI therapy
The Path is a new AI-driven therapy platform founded by wellness and technology veterans to provide more secure mental health support. The startup claims its specialized AI model achieved a score of 95 on the Vera-MH safety benchmark, significantly outperforming general consumer chatbots. The tool is designed to address safety concerns prevalent in general-purpose AI by using benchmarks specifically for mental health applications. read more

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