It's time to get Siri-ous

Top News

• Google may win the Apple AI bakeoff: Apple’s AI woes may be slightly overstated — see yesterday’s show for more — but no matter how you frame the matter, Cupertino’s Siri assistant is dated. That could change next year. Bloomberg reports that Apple is working on a tool called ‘World Knowledge Answers,’ an ‘answer engine’ that will improve Siri’s performance. Google’s AI tech could form its core. The two companies are longterm partners in search, so the tie-up makes sense.

• DuckDuckGo hates the Google remedies: Yesterday Google’s search monopoly case reached the remedy stage, with a judge applying a series of rulings on the tech giant. What were they? Google is banned from exclusive search deals and will have to share some data with rivals, but was not banned from paying for search partnerships nor will it be forced to divest Chrome. DuckDuckGo and other search rivals are crying foul, having hoped for more, and stiffer penalties for the incumbent.

• One more spying saga: The remains of Scale AI is suing a former employee, claiming that he took key documents to Mercor, his new employer. We’ll keep tabs on the case, but in the meantime, are tech companies spying more than before, or are we just hearing about it more often? The Deel-Rippling mess is, of course, still brewing. Sure, the stakes are higher, but seeing more tech shops allegedly engaging in skulduggery is disappointing. (Recall that this sort of corporate case is not de novo to 2025!)

TWiST500

Today in TWiST500-land, we’re looking at two stories:

• xAI’s CFO is out, following a few other senior execs leaving the AI and social media company.

• OpenAI’s secondary offering at a $500 billion valuation is growing, from an initial $6 billion target to more than $10 billion.

Both stories underscore how quickly the AI industry is moving. xAI has churned through senior staff, yes, but it’s also shipping models that are eating market share on the double. (I wrote about Grok Code Fast 1 here, if you want more.) At the same time, interest in AI investments is hardly waning, as OpenAI’s impending tender makes clear.

Nonetheless, it feels like we’ve left AI summer and transported ourselves instantly to AI winter when it comes to market sentiment. Earlier this year, it was common practice for AI fans to keep close tabs on the social media accounts of various lab employees, hoping for hints about the future. But since the release of GPT-5, a model that is performant and lower cost than some expected, the mood has changed.

People expected GPT-5 to do more. And if OpenAI cannot move the ball further forward in the time it took to build GPT-5, perhaps all the AI chatter we’ve been hearing was more smoke and less fire?

Yes and no. Some folks clearly got ahead of their skis and predicted the far future as being close enough to touch. But companies like xAI and OpenAI are still putting models out that people want to use, driving their revenues higher and higher.

Of course, it’s not great that xAI just lost its CFO. Nor is it great that OpenAI has lost a good bit of its luster. But all the same, we can’t stop talking about the large AI labs because they keep shipping. So, as we navigate the news, keep your eyes on the horizon, and not on your shoes. — Alex

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This Week in Startups

E2172: Jason and Alex are back with a packed new TWiST. First up, as humanoid robots become increasingly visible on our streets, and in our lives, is human vs. clanker violence INEVITABLE? Plus…. Apple’s open-source AI models have started to impress, triggering a rethink of the hardware giant’s position in the ongoing race. PLUS another hit model from Grok, Jason’s thoughts on the importance of curiosity, AND a chat with Runbin Dong of Scale Social about knowing your worth as a founder.

E2171: On an all-new TWiST, Jason, Alex, and Lon ponder the mega-success of Netflix’s “KPop Demon Hunters,” whether it will change the company’s strategy regarding theatrical releases, and how Sony — which produced the film, then sold it off for pennies on the dollar — missed out on a huge potential payday. PLUS Grok is counting on speed to outpace its rivals, Nvidia’s massive latest earnings report, and Polymarket attempts to predict the future of OpenAI.

E2170: On Wednesday’s new TWiST, Jason and Alex survey the flood of AI-powered note-taking apps and debate whether there’s any more need for Granola now that Notion has its own native version. PLUS another death has been linked to ChatGPT… is it too easy to get around OpenAI’s safeguards? Is it time for Apple to just buy its way to AI success? Will the US Navy clear a path for more defense tech startups? PLUS a check-in with Colin Russ, whose viral X thread suggested companies may be posting fake jobs to manipulate the H-1B visa process. Check it out!

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Angel University is Back!

Jason and Mike Savino are hosting our next virtual Angel University workshop on Tuesday, October 7. Jason will share proven strategies he’s used to invest $200M+ in over 500 startups. Whether you’re new to angel investing or looking to sharpen your skills, this is your chance to learn directly from one of the most active angel investors in the world. Register now at angel.university!

Founder U is Coming to the MENA Region!

Our 12-week pre-accelerator—designed to help early-stage founders build and grow—kicks off this fall in Saudi Arabia. The first cohort launches in Riyadh on November 3rd, followed by in-person and virtual sessions throughout the program. Founders in MENA: this is your chance to turn your idea into a business and get world-class insights on building a successful startup. Apply today: https://mena.founder.university/

SF Live-Work Space Now Available

Need a flexible living and working environment in San Francisco? This thoughtfully designed loft-style residence at 787 Bryant St., the heart of the vibrant SOMA district and the city’s creative hub, is now available for rent or purchase. Check the listing for more details.

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