OpenAI’s latest “bizarre” mega-deal, previewing Tesla’s big announcement and more | E2189

Today’s show: How many weirdly circular mega-deals is OpenAI going to sign this year? On a new TWiST, Jason and Alex consider OpenAI’s latest agreement with AMD, how the biggest American companies keep trading cash and chips back and forth, and whether or not the entire AI economy might be a house of cards. PLUS what kind of fan/leafblower tech is Tesla working on… what can Jevons Paradox tell us about the AI landscape… how easy is it to master games in the YC Arena… and WHY has NASA never built a base on the moon? We’re asking the TOUGH QUESTIONS so you don’t have to, only on the #1 tech podcast, “This Week in Startups.”

Sora app review, Perplexity’s Comet is FREE, and which AI tools reign supreme? | E2188

Today’s show: Is Sora not just a copyright-killer but a TikTok-killer? Hear our review! The “This Week in Startups” team has been playing around inside OpenAI’s viral app, which just hit #1 in the iOS Store. See all of Lon’s creations, explore the land beyond the Uncanny Valley, and find out why the hottest new social app could stand to be a bit more social. PLUS Brave surpasses 100M MAUs… why Jason would sell ALL his OpenAI shares right away, Apple pulls the ICEBlock app from the App Store, AND how one founder hacked his local coffee shop to network and even get face time with a few VCs! It’s all happening of a fast-paced Friday TWiST.

Sora 2, Tilly Norwood, and the New Slop Era | E2187

Today’s show: Sora 2 will generate a video of whatever you like and respects no IP (unless they opt out) On a brand new TWiST, Jason and Alex check out Sora 2, the latest text-to-video app from TWiST 500 mainstays OpenAI, and look at some of the video videos that have already emerged from the TikTok-style scrolling video app. (TikSlop?) THEN we’re considering the case of “AI actress” Tilly Norwood, and whether her big debut is a legit shift in the world of entertainment or just a marketing gimmick-slash-sales pitch. PLUS Jason’s thoughts on the Wealthfront IPO, how Spotify shifted the entire music economy, Jason’s pitch for making bets with stock purchases, why Americans need more financial literacy, AND another check-in with the sharps over at Polymarket.

Breaking the Sound Barrier with Blake Scholl from Boom Supersonic | E2186

Today’s show: How do you get investors excited about jets when they’re hyper-focused on new AI tools? In a fresh TWiST 500 interview, Alex sits down with Blake Scholl of Boom Supersonic to talk about the Overture, the world’s fastest plane that recently broke the sound barrier over the Mojave Desert. (That’s a first for a private company, rather than a military or government.) Hear about the secrets to avoiding a noisy and disruptive sonic boom, using satellites to set the most efficient routes, designing the Overture’s complex engine, dispelling the common myth that hardware startups are money pits and much much more. PLUS we’ve got two brand new companies entering our Gamma Pitch Deck Competition. Time to see how they stack up to our first impressive entrant, Where2Wheel.

Why New Yorkers hate AI Friends, Producer Claude gets an update, and the value of human writers in the Age of Slop | E2185

Today’s show: Friend’s new AI pendant just wants to be your new pal. So why do New Yorkers hate them? On a brand-new TWiST, Jason and Alex consider the Friend AI pendant, which listens to everything you say all day and then sends you snarky texts about it. WIRED says it’s unhelpful and will make your friends hate you. New Yorkers are so sick of their aggressive subway ads, they’re tagging them with graffiti. But what do Jason and Alex think of the wearable companion? PLUS the value of bringing your last team with you to your new project… why partnerships often lead to purchases… Producer Claude got an upgrade… two fresh TWiST 500 companies… the rise and fall and further fall of Tai Lopez… AND Jason explains the rules of private jets.

Is there an AI coding bubble? Plus Meta’s new SlopTok product, Neon’s divisive app shuts down, and more | E2184

Today’s show: Factory, a Sequoia-backed producer of AI agents for programming, raised $50 million at a $300 million valuation. So Jason and Alex are wondering… how much capital is TOO MUCH? We’re going deep on a question that often perplexes founders: How would weigh a HUGE potential market against STIFF pre-existing competition. PLUS that Neon app that records your calls deleted itself, why AI ISN’T taking away all the radiology jobs yet, how inherent biases impact everyone’s view of the economy, ChatGPT may be getting ads very soon, and MUCH MUCH MORE.

The rise of “workslop,” Alibaba’s insane new deepfake model, Tether’s MASSIVE valuation, and more | E2183

What is “workslop”? And is it already slowing you down at the office? On a new This Week in Startups, we’ve got full co-host quorum with JCal, Alex, AND Lon tackling a meaty docket of news at the cross-section of tech, startups, and pop culture. For starters: A new Harvard/Stanford study suggests that AI isn’t massively improving workplace efficiency because SOME workers aren’t using it properly. Are low-quality, lazily-assembled AI outputs costing US enterprises millions in lost productivity? It’s certainly possible based on these results. PLUS, why YouTube invited back all those banned creators… a deep-dive into CA’s new social media law that’s dividing tech and civil rights advocacy groups… what we can learn from Stripe’s mega-share buyback… a look at what Polymarket’s sharps think will happen with the US TikTok deal… and much more.

Jason’s H-1B pitch, the latest on the TikTok deal, and Howie’s first ad | E2182

Today’s show: New proposal on H-1B visas… and it’s pretty similar to Jason’s pitch from last month! On a new TWiST, Jason and Lon wonder if the White House is watching the pod and borrowing some of our best ideas! Specifically, the new $100K H-1B visa proposal sounds a lot like Jason’s suggestion from August… with a few significant tweaks. PLUS we’re looking at the latest news about the US TikTok entity, why Jason’s not concerned about the new algorithm, the explosion of major data centers in Scandinavia, the European Commission’s scaling back of anti-cookie regulations, AND the first big marketing push from virtual assistant startup Howie! That’s a packed show!

Meta’s “creepy” new Ray Bans, Beehiiv teams with Discord, AND a visit from Lovable CEO Anton Osika! | E2181

Today’s show: On an action-packed TWiST, Alex and Jason check out Meta’s latest wearables, which promise to fix the “constantly staring down at your phone” problem and prevent you from blocking that little light letting others know you’re filming them. Think the upgrade is worth $799 of your hard-earned money? PLUS, Lovable CEO Anton Osika stops by to answer YOUR questions, talk about how people are using the iconic vibecoding app, balancing accessibility and user engagement with the need to actually bring in revenue, and why Stockholm has become arguably Europe’s leading tech hub. AND Beehiiv joins with Discord, Google bakes Gemini into Chrome, and MORE of the week’s biggest tech news. Check out all this and more in a brand-new “This Week in Startups”!

Who Owns the Output? AI Copyright & IP Explained w/ Chris Paniewski | Startup Legal Basics

Today’s show: Jason sits down with Wilson Sonsini partner Chris Paniewski for part two of our *Startup Legal Basics* series on AI law — this time tackling the question every founder is asking: who owns the output of AI systems? Chris has advised on some of the biggest AI deals in history, and in this episode he helps break down how intellectual property law is colliding with generative AI.

Tesla and Uber team up! Plus Weave Robotics’ Isaac and $OPEN bull Eric Jackson | E2180

Today’s show: Hear why Eric Jackson thinks Opendoor is the new Carvana, and how he’s planning to bring Drake on board as an investor (plus Jason’s Bestie Chamath). On a brand-new TWiST, Jason and Alex are chatting with Jackson of EMJ Capital about his hunt for elusive 100 baggers (stocks that return 100-to-1). PLUS we’re chatting with Weave Robotics’ Kaan Doğrusöz about designing practical domestic robots RIGHT NOW, rather than prototypes for 2030. Hear about how they got Isaac to fold laundry like a pro. All that and… why board members should always have skin in the game, AND Uber and Tesla’s first team-up to haul freight!

Why Medium is HIDING from AI | E2179

Today’s show: On a special edition of TWiST, Alex presents a trio of TWiST 500 interviews. First up, Medium CEO Tony Stubblebine on the company’s new Really Simple Licensing (or RSL) initiative, and how it’s helping to compensate writers for their content. THEN, Human Native CEO Dr. James Smith joins for an even deeper dive on AI licensing, why a writer’s content isn’t just DATA to them, and why the company is pivoting away from its old marketplace model. FINALLY, Jason Marks of TELO Trucks stops by to show off his EV mini-truck, walk us through why people need a powerful but tiny truck, and explain why they’re building trucks right here in the US of A.

Robinhood Venture Fund, Polymarket adds earnings, and LAUNCH Accelerator 35 is here! | E2178

Today’s show: There are new LAUNCH Accelerator and Founder U cohorts this week, and Jason’s running down some of his favorite new startups. PLUS Alphabet is the latest member of the $3T club, why Eric Schmidt was SO RIGHT about remote work, Robinhood is opening up private companies to more investors, Polymarket adds earnings reports, how Jason wagered on The Emmys this year, and MORE!

All-In Summit Highlights, Schools Could Block Social Media, FTC Chatbot Investigation, and Zoox hits Vegas | E2177

Today’s show: On Friday’s TWiST, Jason, Alex, and Lon look back at some highlights from this week’s big All-In Summit in Los Angeles, including a fiery, no holds barred presentation from Palantir CEO Alex Karp, Elon Musk delving into the key challenges facing Optimus, and Tucker Carlson debating Mark Cuban on Ukraine. PLUS… why schools may start blocking social media apps, the FTC’s new investigation into social chatbots, AND omnidirectional Zoox robotaxis are headed to Las Vegas.

AI Copyright & Training Data w/ Chris Paniewski | Wilson Sonsini Startup Legal Basics

Today’s show: Jason sits down with Wilson Sonsini partner Chris Paniewski for a special *Startup Legal Basics* on one of the thorniest questions in tech right now: how copyright law applies to AI training data. In this episode, Jason and Chris cover: - Why AI copyright law is unsettled and will take years to shake out - The difference between *training data* and *output* in legal terms - How “fair use” really works (and why it’s a defense, not a permission slip) - The risks of scraping vs. licensing, and why open source ≠ free use - How investors are diligencing AI startups around training data - Why startups must think differently once they’re funded vs. hacking in a dorm room Whether you’re building an AI product, investing in one, or just trying to understand where the law is headed, this conversation breaks down the real legal risks every founder should know.

How Founders Are Building the Next Great Startups | Paid.ai, iTruckr & Tenax AI | E2175

Today’s show: In this TWiST founder triple-shot, Alex digs into the real-world rollout of AI agents: Paid.ai’s Manny Medina explains agent economics and value-based pricing, iTruckr’s Camilo Ramirez shows agents booking loads and coordinating drivers, and Tenax’s Elise Myrans demos computer vision + drones that score a single home’s wildfire/flood risk for smarter underwriting—plus live office-hours on winning enterprise pilots without getting stuck in PoC purgatory.

The Browser Wars heat up! PLUS, Khan on The Bulwark, rules for great domain names, and Polymarket returns | E2174

Today’s show: Jason heard Lina Khan on The Bulwark and got a little fired up. Plus Google doesn’t have to invest in Chrome… or basically do much of anything… Atlassian picked up not just any browser company but THE Browser Company… Follow-up thoughts on that MIT “companies aren’t using AI” study… AND Jason’s “two stock markets” theory. It’s a can’t-miss Friday TWiST.

Creative Structures w/ Becki DeGraw | Wilson Sonsini Startup Legal Basics

Today’s show: Wilson Sonsini Partner Becki DeGraw returns to Startup Legal Basics with Jason. This time, they dive into the *“have” companies* — the breakout startups with multiple term sheets, competitive valuations, and unusual deal terms. From founder voting proxies to mandatory follow-on investment clauses, Becki breaks down the creative “off-menu” structures showing up in today’s financings, and what founders and investors need to watch for. Whether you’re a founder navigating investor FOMO or a VC competing to get on the best cap tables, this conversation will give you insight into the new rules of the game.

Uber, Lucid & Nuro team up on robotaxis by 2026 | E2173

Today’s show: Jason and Alex are joined by Nuro’s Dave Ferguson to unpack the Lucid–Uber–Nuro deal aiming to launch fully driverless Gravity SUVs on Uber by 2026. They dig into why off-the-shelf sensors and Nvidia’s Thor chip drive costs down, how mapping 150 cities improves safety, and why lidar still matters for night and edge cases. Plus: lessons from Cruise’s collapse, how regulators think about safety multiples, and why autonomy could finally make rides cheaper than owning a car.

Jason’s Tesla Optimus prediction, Anthropic’s latest mega-raise and more | E2172

Today’s show: Find out why it’s important to “get curious,” and more deep founder insights on a new TWiST. Jason and Alex are back with a look at Robot vs. Human violence spilling out into the streets, Elon Musk’s vision for humanoid robots, and a reconsideration of Apple’s open-source AI models. Is the hardware giant not getting enough credit for its smaller-scale innovations? Plus Grok has another hit model, AND a chat with Scale Social founder Runbin Dong about the importance of knowing your worth.