Siri sabotage? Apple’s AI team implodes as outsiders move in

The tools and strategies behind rapid scaling

Hi ,

I’ll confess something: I get frustrated with my teenage kids for not helping clean up around the house.

Shocking I know.

I’d ask them to pitch in, and they’d sort of wander around, halfheartedly straightening a pillow or pushing a sock under the couch. It drove me nuts.

But then I realized something, something humbling.

They weren’t being lazy. They genuinely didn’t know what to do. And, if I was honest with myself... neither did I.

There was no plan. No system. Just a vague hope that somehow the house would clean itself if we all “pitched in.”

So I vibe coded a tool for vibe cleaning

A simple app to break household tasks into bite-sized, 15-minute missions anyone can follow. No nagging. No chaos. Just clarity. It’s for parents like me. And for kids like mine.

Let me know what you think.

Let’s dive in.

This week on the podcast:

  • Marco, the co-founder of Crono, shares how his AI-powered sales automation platform is redefining modern B2B outbound LINK

  • Brett Beck joins Ryan Estes to talk about how he built Bella Booty Fitness and launched the patented hip thrust belt that's changing how people train glutes LINK

  • Jake Johnson, co-founder of Bolto, to explore how AI is transforming global hiring and HR LINK

I’m sharing Spotify links for the podcast; is that best?

Tip of the spear:

Apple considers OpenAI and Anthropic for Siri LINK

  • Apple is reportedly in talks with OpenAI and Anthropic to explore replacing Siri's current backend with a version of either Claude or ChatGPT models.

  • The company asked both firms to develop special LLM versions that can run directly on Apple's own secure Private Cloud Compute infrastructure for user privacy.

  • This potential shift comes as Apple's internal AI team is said to struggle with poor morale, making it difficult to deliver major improvements to its technology.

Cloudflare debuts “Pay per Crawl”, a marketplace that lets sites charge AI crawlers per crawl LINK

  • Cloudflare's new Pay per Crawl marketplace experiment lets website owners charge AI companies a set rate for every single crawl of their content.

  • In a major policy shift, new domains set up with Cloudflare will now automatically block all AI crawlers by default to give owners control.

  • New data reveals OpenAI’s crawler scraped websites 17,000 times for every one referral, showing a huge imbalance compared to Google’s search crawler activity.

Amazon's robot workforce now exceeds one million LINK

  • The company has deployed its one millionth robot across its fulfillment centers, bringing its automated workforce closer in number to its 1.5 million human employees.

  • A new AI system called DeepFleet now functions like a traffic controller for robots, improving their travel efficiency by 10 percent using internal data and SageMaker.

  • The growing robot fleet includes a variety of specialized machines like the bipedal robot Digit and Sparrow, a robotic arm that picks individual items from totes.

Microsoft AI diagnoses 4 times more accurately than doctors LINK

  • Microsoft's AI system, when paired with OpenAI's o3 model, correctly diagnosed more than eight of ten complex cases from the New England Journal of Medicine.

  • In the same study, practicing physicians without access to colleagues or textbooks were only able to solve two out of the ten challenging diagnostic case studies.

  • The approach uses a special "diagnostic orchestrator" AI that mimics an expert panel, deciding which tests to order to reach a final conclusion on a case.

Prompt of the week:

Act as a marketing strategist. Analyze the advertising strategy and tactics of [Competitor Name]. Include their ad copy, creative style, messaging tone, channel selection (Google, Meta, YouTube, etc.), target audience, offer structure, landing pages, and funnel design. Highlight what seems to be working for them, what gaps or weaknesses exist, and how I can differentiate my brand (describe briefly: [Your Brand Description]). Provide actionable insights I can use to improve or outperform their approach.

In partnership:

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Keep it moving

US Senate removes controversial ‘AI moratorium’ from budget bill LINK

xAI raises $10B in debt and equity LINK

Grammarly acquires email startup Superhuman to expand beyond grammar and dominate AI work tools LINK

Google issues company-wide AI coding guidance to software engineers LINK

Half a million Spotify users are unknowingly grooving to an AI-generated band LINK

Apple is reportedly working on 7 new headset products LINK

Trump says he found a TikTok buyer LINK

AI is learning to lie, scheme, and threaten its creators LINK

Tesla launches long-awaited Robotaxi LINK

OpenAI removes Jony Ive's io brand amid trademark row LINK

US accuses DeepSeek of military aid and chip ban evasion LINK

OpenAI turns to Google for AI chips LINK

Meta didn’t just buy Scale. It bought the AI arms dealer LINK

Reddit turns 20, and it’s going big on AI LINK

Building with AI Series: 

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Once a month, we’ll dive into a 30-minute live module packed with actionable strategies, tools, and founder stories to help you leverage AI to grow your business.

No hype. Just practical insights from builders who have done it before.

Register free now: LINK

What I’m thinking about:

  • Are podcast transcripts training the next generation of AI? Blog

  • Podcast Interviews Are Feeding the Machine Blog

  • This Daily Practice Made My Digital Life 10x Better Blog

  • AI and the spectrum of consciousness YouTube

Top AI tools: HERE

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Thanks for listening.

-Ryan

p.s. When you are ready, here’s how I can help.


We have successfully booked podcast interviews for over 800 funded startup founders, entrepreneurs with exits, and C-suite executives. If you're ready to lead your company from the front, let Kitcaster handle your podcast scheduling and create a powerful stream of content for you and your brand.

I write about Revops, Product, and Founder-led marketing on Linkedin, Twitter, and my blog

And if you are in Denver, we have the #1 culture and discovery podcast dedicated to the Queen City of the Plains —> realgooddenver.com