Practical AI for Chicago teams
AI training your team will actually use on Monday.
Hands-on workshops and 1:1 coaching for Chicago & Chicagoland businesses, plus help building a business with AI. No hype, no jargon.
25+ years in Chicago real estate · $100M+ in sales · Top 5%, Chicago Association of REALTORS® · AI instructor, Infiniti Properties · Former WCPT 820 AM host · Used to be on WLS radio
01 — Workshops
Learn it. Try it. Use it.
60–90 minutes, hands-on, laptops or phones open. We set the focus together on a quick call first. Everyone leaves with reusable prompts, a one-page cheat sheet and at least one task they can do faster this week.
- Write & researchChatGPT, Claude, Gemini, Grok, Copilot, Perplexity, NotebookLM
- Images & slidesMidjourney, Adobe Firefly, Ideogram, Canva, Gamma
- Video & voiceRunway, HeyGen, Synthesia, Descript, CapCut, ElevenLabs
- Sites & appsLovable, Bolt, Replit, v0, Wix AI, Framer
- AutomationMicrosoft 365 Copilot, Notion AI, Zapier, Make, Otter
02 — Made for your world
Built around your industry.
- InsuranceRenewal reminders and plain-English coverage explainers, reviewed by a licensed pro.
- MortgageBorrower follow-ups and Realtor-partner content without a blank page.
- Salons & spasA month of posts and rebooking texts in your own voice.
- Law firmsIntake summaries and client letters with safe, approved workflows.
- Gyms & restaurantsPromos, win-back emails, menu copy and review replies.
Also a great fit for chambers of commerce, real estate offices and small businesses of every kind.
| Task | Before | With AI |
|---|---|---|
| Listing or product description | 45 min | 3 min |
| A week of social posts | 3 hrs | 20 min |
| Customer email reply | 15 min | 3 min |
| Meeting notes & summary | 40 min | 5 min |
Illustrative examples of everyday tasks. Your results depend on the task and your review process.
Free AI tips for Chicago businesses
Short, practical ideas you can use at work, in plain English.
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03 — Build a business
Build your business with AI.
I help people build businesses with AI and teach you to do it yourself. Whether you are starting from an idea or growing a small business, we work 1:1 or in a small group.
- Shape the ideaResearch your market and customers, and pressure-test the idea.
- Package the offerName, pricing, a simple site and a pitch you can use.
- Market itPosts, emails, flyers and short videos in your voice.
- Run itSimple automations for the day-to-day busywork.
04 — Pricing
Simple, upfront pricing.
In person across Chicago & Chicagoland, or virtual. Final scope is confirmed on a free 15-minute call.
- 1:1 sessions$125 /HR
Private coaching, including business-building. 60-minute minimum.
- Team workshopsFROM $750
60–90 minutes, your location or virtual. Prompt library and cheat sheet included.
05 — About
Hi, I’m Jason.
I’m a self-taught, multi-platform AI instructor, and I train agents on AI at Infiniti Properties. I’m also a Chicago-area real estate broker with more than 25 years of experience and $100M+ in sales.
As the former host of The Jason Rosenberg Show and former co-host of Bell & Company on WCPT 820 AM, I spent years turning conversations into connections, and I used to be on WLS radio. I bring that same approachable, real-world energy to teaching AI, and I use these tools every day in my own business.
I believe AI should feel useful, not intimidating.
06 — Your next step
Ready when you are.
A relaxed 15-minute conversation about where AI could help you most, and whether a workshop or 1:1 coaching is the right fit. No pressure.
FAQ
A few good questions.
I’m a total beginner. Is this for me?
Absolutely. Most groups mix “never opened ChatGPT” with “use it daily.” We start with the basics, go at a comfortable pace and everyone gets hands-on time.
Can the workshop fit my industry?
Yes, that’s the point. On a quick intro call we pick the tasks your team does every week and build the exercises around them.
What about privacy and accuracy?
We practice with fictitious, non-sensitive material and cover each tool’s privacy settings. Protect confidential data, fact-check every output, and keep a human approving anything sensitive. We always work within your firm’s policies.
Can you help me build a business with AI?
Yes, 1:1 at the same $125/hour or in a small-group workshop. The goal is that you learn to do it yourself. Educational coaching only; not legal, tax or financial advice.
How do we book?
Book a free 15-minute intro call, email thejasonrosenbergshow@gmail.com or call 312.882.9797. I’ll follow up with a tailored agenda and quote.