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Welcome to AI Toast!
Here’s what’s on the menu today:
OpenAI is reportedly preparing legal action against Apple
Anthropic debuts Claude for Small Business
Tutorial: How to Create your AI Avatar with HeyGen
Superhero Tools: Job
Quick Toasts: AI-powered hacking is becoming an “industrial-scale threat”
Total read time: About 5 minutes, perfect for a quick coffee break
The deal that put ChatGPT inside Siri looked like a win for both sides in 2024. Two years later, OpenAI says it's been a disaster and their lawyers are now quietly preparing legal action against Apple for breach of contract.
OpenAI believed the Apple partnership would drive millions of new subscribers and eventually become a billion-dollar revenue stream. Instead, Apple buried the integration so deep that most users never find it.
To use ChatGPT through Siri, users have to specifically say the word "ChatGPT" and even then, responses appear in a small, limited window compared to the full app experience.
An OpenAI executive said bluntly: "We have done everything from a product perspective. They have not and worse, they haven't even made an honest effort."
OpenAI is working with an outside law firm on options including sending Apple a formal breach of contract notice though no full lawsuit has been filed yet.
Adding to the tension: OpenAI is now building hardware, led by former Apple design chief Jony Ive and ex-Apple executives making it a potential direct competitor to the iPhone.
Apple has been quietly moving on too. It's now testing integrations with both Claude and Google Gemini for iOS 27, which is expected to be unveiled at WWDC on June 8. OpenAI will still be an option but it won't be the only one.
Apple settled a $250 million class action lawsuit earlier this month over false advertising about Siri AI features that still haven't shipped.
Personal Take: This is one of the messiest breakups in tech right now. OpenAI took a leap of faith, Apple didn't deliver, and now both sides are pointing fingers while quietly setting up alternatives. The irony is that iOS 27's new AI model picker which opens Siri up to Claude and Gemini too might actually give ChatGPT better visibility than the buried integration ever did. Sometimes the fallout works out.
Someone just spent $236,000,000 on a painting. Here’s why it matters for your wallet.
Late last year, a Klimt sold for the highest price ever paid for modern art at auction.
An outlier sure, but it wasn't a fluke. U.S. auction sales grew 23.1% in 2025. The $1-5mm segment even grew 40.8% YoY.
Meanwhile, Apollo’s chief economist Torsten Slok said to expect ‘zero in return in the S&P 500 over the coming decade.’
Each environment is unique, but after dot-com, post war and contemporary art grew about 24% annually for a decade. After 2008, about 11% for 12 years.
It’s also had near-zero correlation with the S&P 500 since ‘95.*
Now, Masterworks lets you invest in shares of artworks featuring legends like Banksy, Basquiat, and Picasso.
$1.3 billion invested across over 500 artworks.
28 sales to date.
Net annualized returns on sold works held 12 months+ like 14.6%, 17.6%, and 17.8%.
Shares can sell quickly, but my subscribers can skip the waitlist:
*Investing involves risk. Past performance is not indicative of future returns. See important Reg A disclosures at masterworks.com/cd.
Anthropic has always focused on big enterprise customers. That's changing. This week they launched Claude for Small Business, a suite of AI tools built specifically for smaller companies, plugging directly into the apps they already run their operations on.
It integrates with Google Workspace, Microsoft 365, Slack, HubSpot, Canva, QuickBooks, and PayPal the everyday tools most small businesses already use.
It runs inside Claude Cowork, Anthropic's automation platform that can browse the web, manage files, and handle multi-step workflows on your behalf no technical skills needed.
Out of the box it comes with 15 ready-to-run workflows and 15 pre-built skills across finance, operations, marketing, HR, and customer service.
Practical use cases include invoice tracking, meeting summaries, marketing content, document organisation, and customer communication the work that piles up after hours.
Anthropic is also taking this on the road, a 10-city US tour starting in Chicago, with free AI training workshops for up to 100 small business owners at each stop.
They've partnered with PayPal to launch a free online "AI Fluency for Small Business" course to help owners use AI tools safely and confidently.
Personal Take: This is Anthropic going after a market that most AI companies have largely ignored the small business owner who doesn't have an IT team but still has a mountain of admin work every week. The smart move here is meeting them inside tools they already know. Nobody wants to learn a new platform. If Claude can quietly handle the invoices, summaries, and follow-ups in the background, that's a genuinely useful product.
One brand built 30+ landing pages through Viktor without a single developer.
Each page mapped to a specific ad group. All deployed within hours. Viktor wrote the code and shipped every one from a Slack message.
That same team has Viktor monitoring ad accounts across the portfolio and posting performance briefs before the day starts. One colleague. Always on. Across every account.
5,700+ teams. 3,000+ integrations.
Superhero Tools (JOB)
Careerflow.ai: Trusted by OVER 1.2 million JOB SEEKERS! Land your dream job.
Without the stress.
AIApply: Get a job-specific cover letter, tailored resume and follow-up email instantly, then auto-apply faster.
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Payscale: Turns compensation into a competitive accelerator of retention, performance and growth putting compensation leaders, HR teams, executives and people managers in control of defensible decisions that finally move at the speed of your business.
Zapier Agents: Create your own superhuman teammates in minutes. Equip your Agents with company knowledge and have them do work across 9,000+ apps on command and while you sleep.
🛠 Step-by-Step Guide
Go to HeyGen
Visit HeyGen and sign in or create an account
Choose “Create Avatar”
Select the AI avatar option from the dashboard
Upload Your Video or Photos
Upload a clear front-facing video or images
Make sure lighting and audio are good
Train Your Avatar
HeyGen analyzes your face, expressions, and voice
AI creates a realistic digital avatar version of you
Add Your Voice
Record your voice or upload audio samples
Optional: use AI voice cloning
Write Your Script
Type what you want your avatar to say
Customize the Style
Choose background, outfit, camera angle, and language
Generate the Video
Click generate → your AI avatar video is created automatically
Download & Share
Export for YouTube, Instagram, presentations, ads, or reels
⚡ What You Can Do with HeyGen
Create talking avatars in minutes
Make videos without filming every time
Generate content in multiple languages
Use avatars for marketing, education, and social media
💡 Pro Tip
Upload a high-quality 2–5 minute video with natural expressions and clear speech → your AI avatar will look much more realistic and accurate.
Quick AI News Bites
Anthropic and the Gates Foundation launched a $200M AI partnership focused on healthcare, education, and scientific research, aiming to expand AI access in developing regions and improve support for African languages.
Anthropic reportedly secured terms for a massive new funding round that could value the company near $900B, showing how aggressively investors are betting on frontier AI.
AI cybersecurity competition is escalating as OpenAI introduced Daybreak, a security-focused AI initiative designed to automate vulnerability detection and patching.
AI-powered hacking is becoming an “industrial-scale threat,” according to new reporting tied to Google security research, with advanced models increasingly used in cyberattacks and exploit discovery.
Wall Street’s AI excitement continues growing, with AI infrastructure company Cerebras surging after its public debut as investors double down on the AI boom.
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— Poonam Soni