Top News
The VC horror stories trend: Today on the show, Jason shared some viral tweets from well-known founders — Greg Isenberg, Travis Kalanick, Mark Pincus, and others — recalling bad venture capitalist behavior, along with some of his own fundraising experiences, positive and negative. It seems that every founder has at least a few anecdotes about awkward, embarrassing, or just unpleasant encounters with VC firms and their partners, and that a surprising number of them include people visibly falling asleep during pitches. Cloudflare CEO Matthew Prince’s stories were among the most widely shared. He shouts out Netscape icon Marc Andreessen for turning a “casual meeting” into a full-blown pitch. (Andreessen responded “there are no casual meetings with VCs.”) Prince also accuses Vinod Khosla of offending him by suggesting that he dump his co-founders and take their stock; Khosla disputes the details and adds “I may sometimes be wrong, but I will always give entrepreneurs my best and honest opinion, popular or not.”
Judge vacates Trump’s H-1B policy: Federal judge Leo Sorokin ruled against a proposed Trump policy, imposing a $100,000 fee on employers filing for H-1B visa applications. In response to a lawsuit brought against the policy by 20 states, Judge Sorokin found that the order violates both the Administrative Procedure Act and the US Constitution. Of course, major US tech companies have long relied on at least theoretically skilled workers from overseas via the H-1B program, which allows foreign-born, non-immigrant workers to take up “specialty occupations” in the US for up to six years. Last year, Trump argued that US companies are abusing the program, replacing American workers “with lower-paid, lower-skilled labor.” The Trump administration told CNBC that they plan to appeal Sorokin’s ruling. Prior to the Trump adjustment, H-1B fees ranged from $2,000 to $5,000 per application.
WSJ profiles Leopold Aschenbrenner’s fund: The 24-year-old German AI researcher and investor is best-known as a former member of OpenAI’s “Superalignment” team who was fired over an alleged leak. His AI-focused hedge fund is named Situational Awareness, after a 165-page paper he published in June 2024, centering around the threats posed to humanity by AGI, and protocols allowing humans to collaborate with superintelligent machines. At just two years old, it already has $20 billion in assets under management due to a number of smart bets. One particularly savvy move, an investment in Claude makers Anthropic, currently accounts for about 1/5th of the fund’s total assets.
TWiST 500
Another TWiST 500 company is leaving the nest and going public, always a bittersweet moment for us here in the newsletter. (But it does open up a new slot! More on that in a bit.)
Italy’s Bending Spoons exists on the border between private equity and a tech operating company. They acquire underperforming but mature digital brands and use a secret blend of corporate strategy, proprietary tech, and AI optimization to turn things around. But UNLIKE PE firms seeking to jumpstart and then re-sell brands over just a few years, Bending Spoons looks to continue managing these companies and expanding their footprints long-term.
Acquisitions to date include, most famously, AOL in 2025, but also the high-end video streaming platform Vimeo, file-sharing service WeTransfer, note-taking app Evernote, and AI-powered photo app Remini. According to their new SEC filing, Bending Spoons had revenue of $601 million (with a net income of $27.5 million) in Q1 of 2026. They’re targeting a valuation between $20 and $22 billion from the public offering.
Meanwhile, one of the startups now vying for the spot being vacated by The Spoon is PointFive. The company, founded in 2023, occupies an interesting niche in the AI landscape. They’re seeking to help companies cut down on wasteful computing expenses, particularly in the cloud.
In the era of always-on AI agents and “token-maxxing,” it’s clear some enterprises are going to require outside help targeting and eliminating unnecessary compute costs. So it’s perhaps not surprising that PointFive’s ARR jumped by six times in 2025, according to CEO Alon Arvatz. They’ve just raised $60 million in fresh capital, in a round led by Accel, at a $500 million valuation. – Lon
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This Week in Startups
E2297: Why does Anthropic want to slow down the development of AI? Aren’t they busy doing just the opposite? And what does Jason think about Vermont Sen. Bernie Sanders’ proposal, that the American people should get 50% stakes in all the major AI companies? Is JCal really considering proposals around Universal Basic (or even High) Income policies? We dig into these questions in a news-heavy TWiST. Plus ComfyUI founder Yoland Yan demos the free, open-source platform, which simplifies and fine-tunes text-to-image and text-to-video workflows, and has been used on high-profile projects like the holiday Coca-Cola ads and “Wizard of Oz” at the Vegas Sphere.
E2296: Want to get to space? Several launch companies can help you. SpaceX, Rocket Lab, the Russians, the list goes on. But what about once you make it upstairs, then what? Impulse Space CEO and CTO Tom Mueller is building the next stage of our orbital economy. Meanwhile, venture capitalists are enamored with the idea of humanoid robots — robots share our shape, our work environment, and even our tools. But startups like Dusty Robotics are taking a different tack; instead of building human-shaped robots, it’s building more specialized ‘bots. Dusty’s CEO, Dr. Tessa Lau, joins Alex to go deep on purpose-built robots in today’s build-crazy market.
E2295: On a two-part TWiST, Alex chats with Cortical Labs founder Dr. Hon Weng Chong about how they’re using human neurons alongside silicon hardware to create “Synthetic Biological Intelligence.” Find out why neurons are more efficient than GPUs at reinforcement learning, and delve into some of the technological and ethical implications of this groundbreaking work. THEN, we welcome Pyka co-founder/CEO Michael Norcia to explore the various uses for his startups’ autonomous aircraft, and why he’s developing the tech all the way down in Brazil.
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