$100 billion sounds like a lot...

Top News

• Nvidia announces $100B OpenAI investment: The chip giant — still the world’s most valuable company — plans to invest up to $100 b-nuts in OpenAI over the next several years, as part of a massive new datacenter build-up. Ultimately, should things go according to plan, they two firms will deploy 10 gigawatts of fresh power toward OpenAI’s looming infrastructure needs. As Jason mentioned on Monday’s pod, some details of the deal remain murky, and it’s certain to attract the interest of regulators. But it’s also a sign that, despite some cultural reservations about the AI boom and fears of a bubble, the industry is moving forward at the same relentless pace of the past few years, with little regard for the backlash.

• Trump’s $100K fee on new H-1B visas: President Trump announced on Friday that the US will now charge a $100,000 fee to companies applying for H-1B worker visas, permitting them to hire skilled international workers. (It’s not very dissimilar from a proposal Jason made on our show last month, in response to concerns from workers that American companies have abused to system to save money, while overlooking qualified domestic workers.) Though Trump’s pitch was widely viewed as a major blow to the tech industry, both Nvidia CEO Jensen Huang and OpenAI’s Sam Altman had largely positive things to say about it on a CNBC hit this morning. Both praised the President for continuing to allow immigrant workers into the US at all and for “streamlining the [H-1B] process,” as Altman described it.

• DeepMind updates “Frontier Safety Framework”: The Google AI team updated a key safety document on Monday, and included warnings that frontier AI models might try to prevent humans from modifying them or shutting them down. Apparently, the group observed some rogue AI behavior in recent tests, noting that models are open to scheming and even deceiving their human users in order to complete assigned goals. The document also cautions against what Google refers to as “harmful manipulation”: basically, when an AI model uses “powerful manipulative capabilities” to significantly change a human user’s “beliefs or behaviors.” DeepMind updates the framework at least once a year to caution the public about emerging AI threats. OpenAI has a similar document, which it introduced in 2023.

TWiST 500

We’re back with a trio of big stories impacting some of our favorite TWiST 500 startups.

Perplexity: The AI leader introduced a new agent aimed specifically at helping to clean up and maintain your email inbox. The Email Assistant lives within either your Outlook or Gmail, and can schedule meetings, summarize threads, clear and set priorities, and even help you draft quick responses (in your own distinctive voice and writing style) to threads that need attention. The big downside? For now, it’s exclusively available as part of Perplexity’s Max subscription, meaning you’ll have to shell out $200/month to try it out.

Scale AI: The data labeling startup — which notably lost its CEO and other leaders to Meta earlier this year — unveiled a new public benchmarking system, known as SEAL Showdown. The platform ranks top-performing AI models based on votes from international contributors, and it has separate categories to reflect these users’ region, profession, and age group. Scale notes that its voters are not just technologists, but experts from a variety of fields, including physicians, lawyers, and scientists, to ensure balance. Currently, there’s no compensation for these contributors, who participate in order to receive free access to the latest frontier models.

Bluesky: Following a divisive few weeks for American social media platforms, the X rival announced plans to take enforcement of its community guidelines more seriously. After a recent request for user feedback prompted an eye-opening 14,000 responses, The Sky said in a blog post that it planned to “return to our experimental rules” and more aggressively enforce rules around posting “harassment and toxic content.” Bluesky has been under fire in some corners for its moderation policies over the past few weeks, with some users complaining that fundraisers for Palestinians in Gaza have been suspended, while others were upset that DC Comics writer Gretchen Felker-Martin was booted for making disparaging comments about late activist Charlie Kirk. – Lon

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This Week in Startups

E2181: Lovable CEO Anton Osika joins us for a blockbuster new TWiST, going deep on his journey developing the app that taught the world how to vibecode. Hear Anton discuss how people are using Lovable, how he balances accessibility with driving revenue, why Stockholm has become such a major tech hub, and much more. PLUS Alex and Jason check out Meta’s latest Ray Bans, Beehiiv’s team-up with Discord, and much more!

E2180: It’s a TWiST double-header as Jason and Alex welcome TWO guests currently blowing up on social media. First, Kaan Doğrusöz of Weave Robotics shows off his company’s Isaac robot, designed for laundry folding, which will actually be released to early adopters later on this year. Then, investor Eric Jackson swings by the show to talk about his investment in Opendoor, and why he thinks the beleaguered company could not only turn things around but become the next “100 bagger.” Plus the “End of Apprenticeship,” Jason’s “Bring Your Own Algorithm” pitch, and much more.

E2179: Alex is back with another trio of TWiST 500 interviews. First up, Medium CEO Tony Stubblebine walks us through the basics of “Really Simple Licensing” (RSL), and how they’re helping writers actually get PAID for their content. Then, Human Native CEO Dr. James Smith takes us on a deep dive of the convoluted world of AI licensing, and explains why his company is pivoting from their former IP marketplace model. Finally, Jason Marks of TELO Trucks introduces us to his EV mini-truck, designed both for tough jobs and big city driving.

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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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