AI DUNN Right Weekly — Issue #34
- 5 days ago
- 7 min read
Practical AI insights for business growth
Hey AI Innovators!
This week, the AI world had a lot to say. OpenAI got some humbling news, Anthropic did something nobody saw coming, and two of the biggest platforms you already use got major AI upgrades.
There is a lot to cover, so let’s get into it.
Here’s what you need to know:
Anthropic quietly passed OpenAI in business AI spend... and the numbers are wild
Claude for Small Business launched with tools you already use every day
GPT-5.5 is now the free default for everyone
WhatsApp added a private AI mode with zero logs
Amazon’s Alexa can now buy things for you automatically
Read time: 6 minutes
Big Story
Anthropic Just Passed OpenAI in Business AI Spend
For a long time, the AI conversation in business went something like this: “Are you using ChatGPT?” It was the shorthand for AI adoption. The default assumption. The thing everyone meant when they said they were “trying AI.”
That assumption just got shaken.
Ramp, the corporate spend management platform used by over 50,000 U.S. businesses, releases a monthly AI Index that tracks actual paid AI usage across their customer base. Their May 2026 report landed like a quiet bombshell: for the first time ever, Anthropic has taken the lead in paid business AI adoption.
Anthropic: 34.4% of businesses paying for AI, up 3.8% in April alone
OpenAI: 32.3% of businesses paying for AI, down 2.9%
Overall AI usage across U.S. businesses now sits at 50.6%
What drove the swing? Two words: Claude Code. Anthropic’s agentic tool has been quietly spreading through finance, legal, and research teams. When those teams switched, the budget followed.
OpenAI’s leadership saw this coming. Fidji Simo, OpenAI’s CEO of Applications, reportedly declared a “code red” two months ago over Anthropic’s enterprise rise. That kind of internal alarm doesn’t happen unless the threat is real.
Here’s why this matters for you: these numbers reflect where real money is being spent by real companies. This is not a benchmark test or a press release. It is actual spend data from businesses paying for results.
The 50.6% overall figure is equally significant. We have crossed the halfway point. More than half of U.S. businesses on Ramp’s platform are now paying for AI tools. The question is no longer whether AI belongs in your business. It is which AI is earning its spot.
My take on this? This is the number that changes the narrative. ChatGPT built the category and Anthropic is now leading it in the market that matters most, the one where people are actually spending money. If you have been putting off choosing your primary AI tool, this is a good week to pay attention.
What’s New This Week
GPT-5.5 Is Now the Default for Everyone
OpenAI rolled out GPT-5.5 as the new default model for all ChatGPT users, including free tier. Some genuinely meaningful upgrades came with it:
52.5% fewer hallucinated claims on high-stakes topics like medicine, law, and finance
Better at following complex instructions and completing multi-step tasks
Same speed as before but significantly smarter
Extended thinking mode on paid plans for complex problems
The catch: it costs more per token for API users, and Claude still has an edge for structured file outputs like PDFs and spreadsheets. For most everyday tasks though, writing, research, summarizing, drafting, this is a real upgrade that makes the free tier meaningfully better.
OpenAI Codex Goes Mobile
OpenAI’s Codex, the agentic tool that runs long multi-step tasks on your behalf, just landed in the ChatGPT iOS app. Kick off a complex task from your laptop, step away, and check in on its progress from your phone. Review what it did, redirect it, approve or reject actions, all from mobile.
It uses a secure relay layer so your computer is not directly exposed to the internet, and it syncs across your ChatGPT sessions. AI that works in the background while you get on with your day. Available across all plans.
WhatsApp Adds a Private AI Mode
Meta quietly rolled out a private mode for the Meta AI assistant inside WhatsApp. Enable it and nothing from that conversation is stored, monitored, or used to train future models. No paper trail.
This opens the door for something a lot of people have wanted: the ability to talk to AI about sensitive topics, health questions, financial decisions, HR situations, without worrying about who is reading it. A significant move that could change how people use AI for personal and professional matters that previously felt too private to type into a chat window.
Amazon Alexa Becomes a Shopping Agent
Amazon folded its standalone Rufus chatbot (300+ million users in 2025) into “Alexa for Shopping,” and the result is genuinely impressive:
Auto-Buy: Set a target price and Alexa buys automatically when the item hits it
Buy for Me: Purchases items from non-Amazon stores on your behalf
Scheduled Actions: Automates restocking based on your usage patterns
Side-by-side product comparisons, price tracking, and delivery timing built in
For business owners who buy supplies regularly, or anyone who wants to stop spending time shopping online, this is worth exploring now.
Tool of the Week
NEW LAUNCH
Claude for Small Business
Anthropic just launched something that feels like it was built for this exact audience: Claude for Small Business.
Here is what makes it different from just “using Claude.” It connects directly to tools you are probably already using:
QuickBooks and PayPal for finances
HubSpot for sales and CRM
Canva for design
DocuSign for contracts
Google Workspace and Microsoft 365
It comes with 15 ready-made workflows across six business areas: finance, operations, sales, marketing, HR, and customer service. Pick a workflow, connect your tools, and Claude handles the task. It drafts, summarizes, sends, organizes, all with your approval before anything goes out, gets posted, or gets paid.
That last part is important. You stay in control. Claude does the work, you give the green light. The kind of setup that actually works for a small business owner who wants AI to save time, not take over.
Anthropic built this for the 44% of U.S. GDP that comes from small businesses. If you have been waiting for an AI tool that plugs into your existing setup without a steep learning curve, this is the one to try this week.
Quick Hits Worth Your Time
→ Anthropic and SpaceX struck a surprise deal. Anthropic now has access to Elon Musk’s Colossus 1 supercomputer in Memphis, 300+ megawatts of compute. This is the same Musk who called Anthropic “misanthropic” back in February. Turns out compute needs and public feuds are separate conversations.
→ SoftBank revealed OpenAI is worth $852 billion. 98% of SoftBank’s Vision Fund gains this year came from that single bet. That number says everything about where the money thinks AI is going.
→ Princeton just brought back supervised exams for the first time since 1893. The 133-year-old honor system could not survive AI and open-tab browsers. If one of the most prestigious universities in the world had to rethink trust and verification because of AI, that tells you something about where we are.
→ Nvidia became the first company in history to hit a $5.5 trillion market cap. CEO Jensen Huang joined Trump in meetings with China’s Xi Jinping. AI infrastructure is now geopolitics.
→ Apple is opening Siri to Claude and Google Gemini in iOS 27, debuting at WWDC on June 8. The Apple-OpenAI relationship is reportedly under serious strain, with OpenAI considering legal action over their 2024 deal not delivering the expected results.
→ Anthropic and the Bill and Melinda Gates Foundation announced a 4-year, $200 million partnership focused on AI for healthcare, education, African language support, and neglected diseases. Frontier AI companies are starting to build public-interest infrastructure, not just products.
Prompt of the Week
With half of U.S. businesses now paying for AI, the gap between businesses using it well and businesses using it occasionally is widening fast. This prompt helps you get specific about where AI can actually save you time.
PROMPT
Why this works: Most people use AI reactively, thinking of it only when they are stuck. This prompt flips that. You are giving the AI a full picture of how your time actually gets spent and asking it to find the leverage points. The three-bucket framework keeps you from handing off things you should not, while making sure you are not manually doing things AI could handle today. Run this once a quarter as your workload changes.
My Take
The Ramp data this week stopped me for a minute.
Not because Anthropic passed OpenAI. That is interesting, but it is not the part that matters most to you. The part that matters is the 50.6% figure. More than half of businesses are now paying for AI. The early adopter window is closing. The gap between businesses figuring this out and businesses still waiting is starting to show up in real numbers.
I hear from a lot of business owners who feel like they have been watching AI from the sidelines, reading newsletters like this one, nodding along, meaning to do something about it but not quite getting there. And I get it. The pace is genuinely hard to keep up with.
But here’s what I want you to take from this week: Claude for Small Business launched with 15 pre-built workflows that connect to QuickBooks, HubSpot, Canva, and the other tools already open on your desktop. WhatsApp added private AI for sensitive conversations. Amazon’s Alexa will now literally buy things for you on autopilot.
The tools are no longer asking you to change how you work. They’re coming to where you already are.
If there is one thing I’d ask you to do this week: try the prompt above. List out your recurring tasks and let AI tell you where you’re leaving time on the table. You might be surprised by what comes back.
See you next week.
Jackie
P.S.
I’m Speaking at the AI Clarity Summit
I am so excited to share this. I am one of the speakers at the AI Clarity Summit, hosted by the wonderful Stephanie Swanson, and registration is open right now.
This is a free, beginner-friendly online event running June 1-14, 2026. There are 28 speakers, all focused on one goal: making AI feel simple, safe, and actually useful for everyday life. If you have a friend, family member, or colleague who keeps saying “I want to learn AI but I don’t know where to start,” this summit was made for them.
My session: “Let’s Open ChatGPT Together: A Beginner’s First Hands-On Walkthrough”
I’m doing a live screen share with no jargon and no overwhelm. We open ChatGPT together, I show you exactly where to click, and you leave knowing how to actually use it in your real life. You’ll also get my free AI Confidence Kit through my speaker link.
A few other sessions from the lineup:
“AI Without the Overwhelm: Practical Prompts for Business Owners”
“The Top Everyday AI Uses: Save Hours Each Week”
“Beginner-Friendly ChatGPT Strategies”
“Using AI to Save Time Without Losing the Human Touch”
And 20 more sessions
Registration is free. This is one of those things I genuinely wish had existed when I was starting out, a warm, practical, no-intimidation space to actually learn this stuff.
Comments