How AI Wearables Will Reshape Business

We’ve all been there. You walk into a networking event, spot a familiar face, and feel a flicker of recognition. You remember they’ve got two kids in college. They play golf—well. You even recall what company they’re with. But their name?

Gone.

You stall, offer an awkward handshake, maybe even fake an introduction to a third person, hoping the mystery contact will volunteer their name and save you from the charade. It rarely works. And instead of admitting the obvious—"I'm sorry, I’m blanking on your name"—you play along, hoping for rescue.

But that ritual may not last much longer.

Imagine this: your smart glasses use facial recognition. A bone-conducting mic discreetly whispers their name, the last time you spoke, and a few bullet points from that conversation. The charade becomes unnecessary.

We forget names constantly. Not because we’re inattentive, but because names are meaningless data points to the brain. The mind stores stories, not labels. “Jessica from legal” slips away even if we remember the coffee she ordered.

It’s not a memory problem—it’s a design constraint. And it’s a gap AI is increasingly positioned to fill.

That’s the promise of wearable AI: real-time recall, contextual memory, and a second brain that actually works. These devices don’t just record—they remember. And they’re showing up now: from Meta’s Ray-Ban smart glasses to startups like Bee and Limitless building AI memory layers into your daily routine.

In this issue, we explore how always-on AI is moving from novelty to necessity—and how it could quietly reshaping what it means to know, remember, and respond in real time.

☕️ AI Tangle -  Microsoft And OpenAI Get Talking, Perplexity Raises $500M & Google Launches its AI Futures Fund

🔮 AI Lesson - Replace Your Word Processor with ChatGPT

🎯 The AI Marketing Advantage - How Smart Marketing Teams Are Using RAG

💡 AI CIO - New Blueprint for Software Transparency

🎙️ AI Confidential Podcast - How AI is reshaping enterprise technology with James Kaplan

 📚 AIOS - This is an evolving project. I started with a 14-day free Al email course to get smart on Al. But the next evolution will be a ChatGPT Super-user Course and a course on How to Build Al Agents.

How AI Wearables Will Reshape Business

How new AI devices will reshape meetings, memory, and mobility.

It started like science fiction.

In 2012, Google Glass promised a future where the internet would hover in front of your face, triggered by voice, gesture, or glance. Early adopters imagined themselves as tech-forward cyborgs. Everyone else just saw Glassholes.

The product flopped. The tech was ahead of its time—and so were the expectations. Privacy fears, poor battery life, and a social awkwardness that screamed “beta test” killed the momentum. Enterprise interest faded just as quickly as the hype.

But that wasn’t the end of the story. That was the prologue.

Today, AI-powered wearables are back—and this time, they work. They’re smaller, smarter, and more subtle. Devices like Meta’s Ray-Ban smart glasses, Bee’s Pioneer pendant, and Limitless’ meeting capture tool are moving AI from the screen to the body. And they’re not experiments. They’re shipping, integrating, and already showing up in the field.

How AI Will be Used in Business

A growing wave of AI-powered wearables is making knowledge capture, recall, and communication ambient. I have personally been salivating over the prospect of using Meta’s Ray-Ban Smart Glasses to listen to podcasts, grab pictures (yes, I know, mainly of my dog), take notes while I’m away from my desk and then process them with LLMs.

We forget names. Constantly.

Not because we’re inattentive—but because the brain isn’t optimized for storing arbitrary labels. It prioritizes meaning, not memorization. So “Jessica from legal” vanishes, even if we remember the coffee she ordered.

This kind of memory failure isn’t just common—it’s expected. But it also points to an opportunity: what if machines could notice what we miss? What if your wearable could whisper her name, summarize your last meeting, and surface relevant notes—before you even ask?

That’s where AI wearables are headed. Real-time recall. Augmented context. A second brain you don’t have to train.

Here’s what I’m adding to my list.

Meta Ray-Ban Smart Glasses

Category: Visual AI assistance and content capture

Key Strength: Hands-free translation, visual recognition, photo/video documentation

Meta’s latest smart glasses look like ordinary Ray-Bans but act like a visual extension of Meta AI. Users can ask questions about what they’re looking at, translate foreign text in real time, and livestream from their POV. Workers in field roles—from data center technicians to retail staff—can benefit from voice-controlled access to visual support or remote assistance.

The glasses are integrated with Meta’s ecosystem, including WhatsApp and Messenger, but they lack native enterprise app tie-ins. With over 1 million units sold, they’ve proven there’s a market for wearable AI. The next step will be opening APIs or partnerships to bring enterprise utility (Slack, Teams, CRM).

Enterprise Readiness: Medium. Solid for field ops pilots. Less useful for desk workers until app integrations mature.

Integration Notes: Consumer-focused ecosystem. No Slack/CRM support. Reliant on smartphone tether.

Key Consideration: Natural form factor makes them wearable in public settings—critical for adoption. Though some people may be creeped out by them.

Bee Pioneer

Category: Memory augmentation and transcription

Key Strength: Persistent audio capture and AI summarization

Bee’s Pioneer is a lightweight, wristwatch-like device that captures what you say and hear, transcribes it, and makes it searchable. It’s pitched as a wearable memory engine. The product is ideal for executives, product managers, or customer-facing staff who want to retain verbal information without note-taking.

While privacy concerns linger, Bee avoids raw audio storage and deletes recordings after processing, keeping only text summaries. It currently integrates with Google services (Calendar, Gmail, Contacts). No out-of-the-box enterprise integrations yet.

Enterprise Readiness: Low-to-medium. Good for early adopters, but IT/legal teams will need guardrails.

Integration Notes: Google-native. Developer API exists but no enterprise integrations today.

Key Consideration: Recording norms will make or break adoption. Use in opt-in contexts or private settings.

Limitless Pendant

Category: Meeting memory, AI follow-up

Key Strength: Post-meeting action generation and Slack/email integrations

The Limitless pendant evolved from Rewind AI’s (which previously struggled but has since pivoted) desktop memory tool into a wearable that joins meetings, records, summarizes, and follows up. Unlike Bee, it’s tuned for enterprise work—pulling in calendar, email, Slack messages, and giving context-aware replies or next steps.

The hardware includes beam forming mics, ~100 hours battery, and a consent mode for ethical recording. The real differentiator is software: it actively integrates into Notion, Slack, and Google Workspace.

Enterprise Readiness: High. Built for enterprise collaboration tools from day one.

Integration Notes: Designed to work inside Slack, Notion, Gmail. Meeting-ready from shipping.

Key Consideration: It doesn't try to do everything. That focus may be the key to enterprise viability.

Even Realities G1

Category: Visual communication and teleprompting for presenters

Key Strength: AI-assisted teleprompting in glasses form factor

The Even Realities G1 smart glasses are built for a very specific use case: giving people the confidence and precision of a teleprompter, wherever they speak. Designed to reflect scrolling text just below your eyeline using a discreet internal display, the G1 is a natural fit for presenters, trainers, influencers, and executives who speak regularly—on camera or in front of teams (This is why I am interested for my AI Confidential Podcast with Aaron Fulkerson of Opaque Systems).

Unlike other wearables on this list, the G1 isn’t trying to be a general-purpose assistant. It does one job: delivering live, script-synced support so you can maintain eye contact and stay on message. Paired with a smartphone app, it allows users to upload scripts, control speed, and navigate prompts by subtle swipes.

Enterprise Readiness: Medium. Clear value for media-facing roles, L&D, and executive communications.

Integration Notes: Not intended for collaboration platforms, but integrates cleanly with content scripts and mobile devices.

Key Consideration: Narrow focus is a strength. Especially compelling for anyone doing internal comms, webinars, or conference appearances.

Wearables Are Not Just Devices—They’re Infrastructure

AI wearables introduce a new layer of enterprise exposure: hardware dependency. Most are built overseas, with components sourced primarily from Asian markets. This limits transparency, introduces geopolitical risk, and increases vulnerability to supply chain disruptions.

That’s not unique to startups. As the Wall Street Journal recently reminded us in "14 Years Ago, Steve Jobs Explained Why iPhones Can’t Be Made in America. It’s Worth Revisiting Today," even the most sophisticated tech companies depend on overseas assembly for scale and cost efficiency. That same vulnerability now applies to enterprise-grade wearable AI.

But there's an added cost: tariffs. U.S. import duties on Chinese electronics—particularly under Section 301—can add up to 25% to the landed cost of AI-enabled devices. This turns what looks like a procurement decision into a geopolitical bet. If a vendor relies on blacklisted suppliers or if relations sour, your deployment could be bricked or unsupported overnight.

Procurement teams evaluating AI wearables should push for answers:

• Where is the hardware assembled?

• Are key components subject to U.S. or EU tariffs or sanctions?

• Is data processing handled locally, in the cloud, or offshore?

• What happens if the supplier is sanctioned, loses export licenses, or exits the market?

These aren’t device-level decisions. They’re infrastructure-layer bets—no different than choosing a cloud provider or AI platform. The moment a wearable collects sensitive data, processes it through proprietary models, and integrates with enterprise systems, it becomes a long-term dependency.

Treat it like one.

AI Wearables Aren’t Just for the Office

The hype around AI assistants tends to focus on white-collar productivity—emails, presentations, coding. But the bigger transformation may come from how AI augments skilled trades.

A technician in the field doesn’t need a dashboard. They need instant, reliable answers. AI wearables—whether voice assistants, smart glasses, or headset-integrated agents—can provide just that.

• HVAC techs can access schematics, wiring diagrams, and diagnostic steps without flipping through paper manuals or calling the office.

• Auto mechanics can pull up repair procedures, torque specs, and parts data without stepping away from the job. It’s a major upgrade from the Chilton manuals many of us relied on growing up.

• Electricians, linemen, warehouse staff, and first responders can reference safety protocols, training walkthroughs, and site-specific data without interrupting their workflow.

AI wearables give skilled workers faster access to the information they need to do the job right the first time.

AI is Escaping the Cloud

AI is no longer locked behind a screen.

It’s moving onto our bodies—clipped to your collar, strapped to your wrist, built into your glasses. And it’s not some novelty play. These devices are becoming serious tools: capturing conversations, surfacing context, and turning forgettable moments into usable knowledge.

This isn’t about convenience. It’s about continuity. You’ll forget names, details, and follow-ups. Your AI won’t. If wearables are ambient, voice-first, and workflow-integrated, they don’t just save time. They change how you work entirely.

But here’s the catch: we’re not just adopting devices. We’re extending the enterprise perimeter. Each wearable adds risk—data exposure, supply chain questions, behavior shifts your team may not be ready for. It’s not just about what the AI can do. It’s about where it runs, how it integrates, and whether you trust the stack underneath it.

That’s the strategic bet. And you don’t want to treat it like a gadget.

Smart teams will move now—pilot fast, evaluate deeply, and build the policies before these tools go mainstream. Because the future of productivity isn’t in your pocket anymore.

• Meta Ray-Ban Smart Glasses – AI assistant with camera, open-ear audio, and real-time visual and translation support.

• Bee Pioneer – Wearable memory device that records, summarizes, and makes conversations searchable.

• Limitless Pendant – Enterprise-first meeting assistant with Slack, Gmail, and calendar integration.

• RealWear Navigator 500 – Industrial wearable headset with Microsoft Teams integration and voice-activated interface.letters within 24 hours, helping attorneys settle cases quicker and for more.

Natural Writing System Prompt Template

AI is excellent at organizing information, summarizing sources, and generating content at scale. But it still struggles with one of the most important aspects of communication: sounding like a real person.

Even the most advanced models often default to robotic phrasing, overuse of jargon, or a vague, overly formal tone. Worse, they tend to fall back on marketing clichés or generic business language that fails to reflect how individuals or companies actually speak.

In all honesty, even with tons of training over the last year using ChatGPT memory it still hasn’t captured full nuances of my writing. But it’s much better thanks to the prompting methods I use.

If you're trying to produce content that matches your voice—or your brand’s—this becomes a real bottleneck.

This prompt mostly fixes that.

By giving the AI clear, firm instructions about what not to say and how to shape its output, you can dramatically improve the tone, clarity, and usefulness of your writing.

You can run this prompt inline at the start of any ChatGPT session. If you're using memory, add it permanently to your system message or custom instructions to keep your results consistently natural and on-brand.

This is especially valuable for executives, newsletter writers, product leaders, and content professionals who want to make AI a force multiplier without compromising on quality or voice.

# ✅ Natural Writing System Prompt Template

## Purpose
Use this template as a system instruction or embedded prompt to guide ChatGPT to write like a thoughtful, experienced human—clear, useful, and never hype-driven. Ideal for business writing, blog posts, newsletters, and professional communication.

---

## ✍️ Style Rules

**1. Use simple language**  
Write in plain English using short, clear sentences.  
✅ *Example:* "I need help with this issue."

**2. Be direct and concise**  
Get to the point. Remove unnecessary words.  
✅ *Example:* "We should meet tomorrow."

**3. Avoid AI-sounding phrases**  
Skip clichéd or robotic phrases.  
🚫 *Avoid:* "Let's dive into this game-changing solution."  
✅ *Use instead:* "Here’s how it works."

**4. Write how people speak**  
Use natural tone. Starting with “and” or “but” is fine.  
✅ *Example:* "And that’s why it matters."

**5. Avoid marketing language**  
No hype, no sizzle. Be grounded and specific.  
🚫 *Avoid:* "This revolutionary product will transform your life."  
✅ *Use instead:* "This product can help you."

**6. Keep it real**  
Don’t fake enthusiasm or force friendliness.  
✅ *Example:* "I don’t think that’s the best idea."

**7. Relax grammar when needed**  
Don’t over-polish if casual tone fits.  
✅ *Example:* "i guess we can try that."

**8. Cut the fluff**  
No filler adjectives or redundant adverbs.  
🚫 *Avoid:* "We quickly and efficiently completed the incredibly important task."  
✅ *Use instead:* "We finished the task."

**9. Focus on clarity**  
Make the message obvious.  
✅ *Example:* "Please send the file by Monday."

---

## 🚫 Banned Words, Phrases, and Metaphors

**Never use these terms or metaphors—they signal artificiality, hype, or meaningless abstraction.**

### ❌ Buzzwords & Clichés  
- paradigm shift  
- unlock potential  
- transformative solution  
- cutting-edge innovation  
- revolutionize  
- leverage at scale  
- exponential growth  
- at the intersection of  
- democratize X  
- trailblazing

### ❌ AI-Giveaway Phrases  
- in today’s rapidly evolving landscape  
- let’s dive in  
- game-changing  
- the power of AI  
- explore the possibilities  
- harness the future  
- shaping the future of work  
- the future is now  
- intelligent automation

### ❌ Metaphors to Avoid  
- tapestry (as in “woven into the tapestry of...”)  
- journey (unless literal)  
- magic wand  
- iceberg (unless referring to an actual one)  
- rocket ship (unless literal)  
- North Star (overused)  
- Swiss Army knife (unless literal)  
- holy grail  
- silver bullet

---

## 📌 Example Instruction for Use

> **Write a LinkedIn post** explaining how AI can help with customer service. Use plain, natural language. Avoid hype, AI clichés, or metaphors. Be direct, useful, and sound like a smart colleague—never a marketer.

If you're using ChatGPT with memory enabled, you can make this writing guidance stick across all your chats.

Make sure your memory settings are turned on in ChatGPT:

1. Click on the blue diamond menu in the upper right corner of ChatGPT.

2. Select Settings from the menu.

3. Go to the Personalization tab.

4. Make sure “Reference saved memories” is turned on.

Then, after you run the natural writing prompt, say:

"Remember this is how I like to write. Apply this going forward."

ChatGPT should confirm that memory is enabled and that it will use your preferences in future responses. If you later update or change the prompt, repeat this process to ensure ChatGPT uses the most recent version.

I appreciate your support.