Jason Calacanis

This Week in Startups

Jason Calacanis covers startups, tech, markets, media, and all the hottest topics in business and technology. He also interviews the world’s greatest founders, operators, investors, and innovators.

Author

Jason Calacanis

Category

Technology

Podcast website

thisweekinstartups.com

Latest episode

Jul 10, 2026

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Episodes

Battery Power for Texans with Zach Dell, plus Tim Apple is LEAVING?, Polymarket to the US, and a Tesla fan update | E2190 09.10.2025

Today's show: *Zach Dell of Base Power joins us at the top of today's show to talk about building batteries in Austin, that $1 billion investment, and why an "all of the above" energy strategy is the only way forward. PLUS Jason and Alex's thoughts on that Tesla non-upside down car announcement, growing resentments toward AI datacenters, Chinese robots actually going on sale, Tim Cook's potential...

We're Hiring! Join the This Week in Startups Team 08.10.2025

Everything's going great here at This Week in Startups — and we're expanding! As we launch a brand new podcast next year, we're looking to bring on two new creative roles: Video Editor — Full-time or part-time, remote or in-person (Austin). If you love startups and tech and you're skilled at editing, this is your shot. Send your portfolio to editor@launch.co . Short-Form Video Editor (CapCut) — He...

OpenAI's latest "bizarre" mega-deal, datacenters in space, previewing Tesla's big announcement and more | E2189 07.10.2025

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...

Sora app review, Perplexity's Comet is FREE, and which AI tools reign supreme? | E2188 04.10.2025

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 Jas...

Sora 2, Tilly Norwood, and the New Slop Era | E2187 02.10.2025

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...

Breaking the Sound Barrier with Blake Scholl from Boom Supersonic | E2186 30.09.2025

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 secre...

Why New Yorkers hate AI Friends, Producer Claude gets an update, and the value of human writers in the Age of Slop | E2185 29.09.2025

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 wit...

Is there an AI coding bubble? Plus Meta's new SlopTok product, Neon's divisive app shuts down, and more | E2184 27.09.2025

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 IS...

The rise of "workslop," Alibaba's insane new deepfake model, Tether's MASSIVE valuation, and more | E2183 25.09.2025

Today's show: 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...

Jason's H-1B pitch, the latest on the TikTok deal, and Howie's first ad | E2182 23.09.2025

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...

Meta's "creepy" new Ray Bans, Beehiiv teams with Discord, AND a visit from Lovable CEO Anton Osika! | E2181 19.09.2025

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 a...

Who Owns the Output? AI Copyright & IP Explained w/ Chris Paniewski | Startup Legal Basics 18.09.2025

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. Jason and...

Tesla and Uber team up! Plus Weave Robotics' Isaac and $OPEN bull Eric Jackson | E2180 17.09.2025

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 domesti...

Why Medium is HIDING from AI | E2179 16.09.2025

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 t...

Robinhood Venture Fund, Polymarket adds earnings, and LAUNCH Accelerator 35 is here! | E2178 15.09.2025

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! Timestamps:...

All-In Summit Highlights, Schools Could Block Social Media, FTC Chatbot Investigation, and Zoox hits Vegas | E2177 13.09.2025

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 investigat...

AI Copyright & Training Data w/ Chris Paniewski | Wilson Sonsini Startup Legal Basics 11.09.2025

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. Chris has worked on some of the biggest AI deals ever — including Scale AI's $14B+ partnership with Meta and OpenAI's $6.5B acquisition of Jony Ive's design studio — and brings practical, on-the-ground ins...

Republic opens private markets as Positron takes on GPUs: A TWiST500 doubleheader! | E2176 10.09.2025

Today's show: In this founder-focused episode of This Week in Startups, we sit down with Republic's Kendrick Nguyen to learn more about the company's efforts to make the private markets accessible to the common investor. Best known for its work in equity crowdfunding, the Valor-backed startup now offers access to secondary shares, tokenized assets, and much more. Following, TWiST spoke with Positr...

How Founders Are Building the Next Great Startups | Paid.ai, iTruckr & Tenax AI | E2175 09.09.2025

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-ho...

The Browser Wars heat up! PLUS, Khan on The Bulwark, rules for great domain names, and Polymarket returns | E2174 05.09.2025

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. Timestamps: (00:00) Sony respo...

Creative Structures w/ Becki DeGraw | Wilson Sonsini Startup Legal Basics 04.09.2025

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...

Uber, Lucid & Nuro team up on robotaxis by 2026 | E2173 03.09.2025

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 abo...

Jason's Tesla Optimus prediction, Anthropic's latest mega-raise and more | E2172 03.09.2025

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 anoth...

KPop Demon Hunters breaks records, Grok speeds up, and an AI-powered browser deep dive | E2171 29.08.2025

Today's show: *"KPop Demon Hunters" is one of the year's biggest smashes… AFTER Sony sold it off to Netflix for cheap! Hear about what went wrong with one of the year's worst deals… PLUS Grok is counting on SPEED to help it outpace rivals… How Rep. Ritchie Torres (D-NY) ran into trouble on the podcast circuit… Nvidia's big earnings report, and why everyone is watching that company in particular SO...

Market Update and Trends w/ Becki DeGraw | Wilson Sonsini Startup Legal Basics 28.08.2025

Today's show:Wilson Sonsini Partner Becki DeGraw returns to Startup Legal Basics with Jason to break down what's happening in today's startup market. From excess dry powder on the VC side to companies struggling to "grow into" their valuations, Becki shares what founders need to know about deal terms, pay-to-play provisions, and the shift from the 2021 heyday to today's more structured environment...

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