Description
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.
Episodes
- 2025 / 8 / 29KPop Demon Hunters breaks records, Grok speeds up, and an AI-powered browser deep dive | E2171Today’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...
- 2025 / 8 / 28Market Update and Trends w/ Becki DeGraw | Wilson Sonsini Startup Legal BasicsToday’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...
- 2025 / 8 / 27Google is Nano Banana, Apple AI plans & The Great H1B Visa Debate | E2170Today’s show:On a brand-new TWiST, Jason and Alex are asking why there are SO MANY note-taking AI apps?Plus another death has been linked to ChatGPT… is it too easy to get past chatbot guardrails? Why Donald...
- 2025 / 8 / 26xAI’s App Store lawsuit, Intel shares vs. grocery stores, and Netskope’s IPO | E2169Today’s show:On an upbeat and optimistic new TWiST, Jason and Alex are debating why any new innovation or technology gets hit with a wave of bitter cynicism.PLUS Jason defends the government taking shares of...
- 2025 / 8 / 22Do Kwon Guilty, Powell Pivot & OpenAI’s $12B Run Rate | E2168Today’s show:Terra’s collapse, Powell’s pivot, and OpenAI’s explosive growth all collide in this TWiST deep dive.Do Kwon has pled guilty after Terra/Luna’s $60B implosion, Fed Chair Powell hints at a...
- 2025 / 8 / 20Is Chalk.ai the ‘Next Databricks’? + Tollbit’s Bot Paywall for AI Agents | E2167Today’s show:In this TWiST 500 double feature, Alex sits down with two breakout founders: Chalk’s Marc Freed-Finnegan & Tollbit’s Toshit Panigrahi!First, Chalk’s CEO Marc Freed-Finnegan is tackling one of...
- 2025 / 8 / 19Scaling AI Photo Editing to 300M Users with Photoroom’s Matt Rouif | AI Basics with Google CloudIn this AI Basics episode, Jason sits down with Matt Rouif, Co-founder & CEO of Photoroom — the AI photo editing app with 300M+ downloads and 5B images processed annually.They break down:Why Photoroom...
- 2025 / 8 / 18Decart makes AI faster, Lume teaches lamps to fold laundry | E2166Today’s show:We’re back with two insightful new TWiST founder interviews.First up: Dean Leitersdorf of Decart tells us about squeezing maximum productivity out of your GPUs. But it’s not all talk: he also...
- 2025 / 8 / 15Meta’s “Sensual” AI Doc LEAKS, Opendoor’s dreams became memes + OpenAI plans $1T data center spend | E2165It’s a Friday TWiST and Jason and Alex are FIRED UP about this internal Meta doc laying out appropriate vs. inappropriate AI behavior… You won’t BELIEVE with what Zuck approves for 8-year-old users.PLUS… AI...
- 2025 / 8 / 14The End of the ZIRP Era, and why recruiting is SO PAINFUL | E2164Today’s show:We’re back with another all-star VC roundtable discussion.Joining Jason are Dave McClure of Practical VC, NVNG’s Grady Buchanan, and Tomasz Tunguz of Theory VC. Together, they’re having a deep...
- 2025 / 8 / 12GPT Psychosis is spreading, the NYT is Super-Doxxing Zuck, and Trump is wetting his beak on Chinese chip exports | E2163Today’s show:On an all-new Monday TWiST, Lon joins Jason and Alex to talk about a whole bunch of stories at the intersection of tech, business, and pop culture.First up, is GPT Psychosis real? And if so, what...
- 2025 / 8 / 8GPT-5 comes alive, Apple is struggling, and Ripple bought Rail | E2162Today’s show:Jason and Lon recorded a Thursday night special edition, so no Alex this time, but still lots to talk about.First up, Jason thinks it’s time for Tim Apple to exit the stage in lieu of a product...
- 2025 / 8 / 7Communist coffee hits NYC, RIP Hulu, GPT-5 arrives and more | E2161Today’s show:It’s a brand-new PACKED episode of TWiST. Jason and Alex welcome guest Zach Dive of Adam.new, to tell us why he made a deepfake AI ad starring Jason and the All-In besties.PLUS a rundown of the...
- 2025 / 8 / 5Lina Khan’s Figma victory lap, Meta’s Superintelligence Team, BYD mega car-carrier video & MORE | E2160Today’s show:Jason and Alex are running down the biggest tech, startup, and business stories of the day on a brand-new Monday TWIST.Which countries are leading the AI race, based on academic papers? Why Jason...
- 2025 / 8 / 1TWiST 500 interviews with Cortical Labs, Turing, AND Mercor | E2159Today’s show:Alex is back with three more awesome interviews with founders on the bleeding edge of innovative tech.Dr. Hon Weng Chong walks us through the basics of biological computing and Cortical Labs’...
- 2025 / 7 / 30All Star Investor Panel! Sophia Amoruso and Ryan Hoover | E2158Today’s show:It’s another All Star Investor Panel! Jason and Alex welcome TrustFund VC founder Sophia Amoruso AND WeekendFund investor/Product Hunt founder Ryan Hoover.Together they’re going DEEP on the...
- 2025 / 7 / 29Figma IPO, IMAX AI Festival, the Tea app spill, that one Sydney Sweeney jeans ad, and more! | E2157Today’s show:SYDNEY SWEENEY’S AMERICAN EAGLE AD DIVIDES OUR PANEL!PLUS WHAT STARTUPS CAN LEARN FROM THE VIRAL ASTRONOMER RESPONSEJason, Alex, and Lon are looking at some of the biggest media stories of the...
- 2025 / 7 / 25Behind the scenes at the ALL-IN AI SUMMIT w/ POTUS, JD Vance, Jensen Huang, Lisa Su, and more… | E2156Today’s show:Jason’s back and filling us in on his experiences in Washington DC, at the All-In AI Summit, including getting a Trump shoutout from stage, debating immigration with VP Vance, and calling out...
- 2025 / 7 / 23AUTOMATING HEALTH CARE, THERMODYNAMIC COMPUTING, AND PRODUCT VELOCITY | E2155Today’s show:TWiST is back with a three more hugely insightful (and also fun!) founder interviews.First up, Trey Holterman from Tennr tells us why getting in to see a specialist is so time consuming, and how...
- 2025 / 7 / 21Manufacturing in the US, Building in Open Source… and more | E2154Today’s show:TWiST is back with a trio of can’t miss interviews with some of our favorite TWiST 500 founders.First up, John Jeremy Harris of Harbinger Motors tells us about making his EV batteries right here...
- 2025 / 7 / 18Inside Substack’s $100M Push to Fend Off Beehiiv | E2153Today’s show:WHY DOES @SUBSTACKINC NEED $100M IN NEW FUNDING?HOW DO THEY PLAN TO STAY AHEAD OF @BEEHIIV?Jason and Alex are debating the future of indie publishing on an all-new TWiST, considering the future...
- 2025 / 7 / 17Thinking Machines’ RECORD seed round, VC Geoff Lewis, and MORE | E2152Today’s show:Jason and Alex tackle a full tech and business news docket on today’s show, including Jason’s big SF trip with Launch Accelerator’s 34th cohort, some peculiar social media posts from VC Geoff...
- 2025 / 7 / 14Blitzhiring and the Complicated Case of Windsurf, OpenAI and Google | E2151Today’s show:On today’s show… Jason and Alex are considering the fallout of Windsurf’s OpenAI deal, the company’s latest agreements with both Google and Cognition AI, and how “blitzhiring” is actually playing...
- 2025 / 7 / 12Grok 4 Beats OpenAI + The $300 AI Agent Era | E2150Today’s show: Grok 4 just leapfrogged OpenAI to become the top AI model—and it’s not just hype. In this episode, @Jason and @alex break down Grok’s AGI-level performance, the massive drop in LLM pricing, and...
- 2025 / 7 / 10Orchestrating Smarter AI Systems with AI21 Labs’ Yoav Shoham | AI Basics with Google CloudIn this episode of AI Basics, Jason sits down with Yoav Shoham — Stanford professor emeritus and co-founder of AI21 Labs, creators of Jurassic-2, Wordtune, and the new orchestration system Maestro.They...
- 2025 / 7 / 9Starlink + Tesla? $4T Nvidia? Perplexity Browser? Linda Yaccarino Steps Down? | E2149On a brand new TWiST, Jason and Alex ponder… What if every Tesla doubled as a Starlink-powered Wi-Fi hotspot? Plus, Nvidia’s historic $4T valuation, Perplexity’s fancy new AI browser that literally books...
- 2025 / 7 / 9Cloud Seeding, Conspiracies & the Texas Floods | BONUS EPISODE!Today’s show:Cloud seeding startup Rainmaker faced a viral backlash after deadly floods in Texas—so @Jason hosted an emergency X Spaces with founder Augustus Doricko to unpack what really happened. Did...
- 2025 / 7 / 7Exits Are Back, QSB Stock & The New America Party? | E2148Today’s show:Startup exits are heating up with $67.7B in Q2 activity, QSBS just got a major expansion, and Robinhood is pushing boundaries with tokenized SPVs. In this episode, @Jason and @alex break down...
- 2025 / 7 / 2Startup Valuations, Biotech’s Crunch & AI’s Massive TAM | E2147Today’s show:It’s another blockbuster panel of insiders, as Alex sits down with Astasia Myers from Felicis, Matt Turck from First Mark Capital, and D.A. Wallach of Time BioVentures. AI is reshaping...
- 2025 / 7 / 1The Grammarly–Superhuman Megadeal, plus TWiST 500 chats with LabelBox and Apptronik’s founders | E2146Today’s show:Grammarly is acquiring the beloved email app Superhuman! In today’s extremely timely episode, @alex sits down with Grammarly CEO Shishir Mehrotra and Superhuman founder Rahul Vohra to unpack why...
- 2025 / 6 / 30Rebuilding Civilization from First Principles: Inside Balaji’s Network State Vision | E2145Today’s show: Jason sits down with Balaji Srinivasan in Singapore to explore how he's turning years of theory into reality with Network School—the first node of a broader vision for internet-native,...
- 2025 / 6 / 27Travis’ Uber Comeback, AGI’s Stakes, Meta’s $100M AI Hires & Prediction Market Gold Rush | E2144Today’s show:EVs are igniting a global tariff war, and Xiaomi’s shockingly cheap, high-quality electric cars threaten to obliterate Western automakers, sparking fears of a manufacturing wipeout. In today’s...
- 2025 / 6 / 26Multi-Agent AI, Open Protocols & Startup Acceleration with Saurabh Tiwary | AI BasicsIn this episode, Jason dives deep into the future of multi-agent systems with Saurabh Tiwary, VP & GM of Cloud AI at Google. They explore how teams of AI agents—not just single models—can collaborate to solve...
- 2025 / 6 / 26VC Roundtable: Recruiting Secrets, Second-Time Founders & Product-Market Fit Myths | E2143Today’s show:In this powerhouse VC roundtable, @Jason sits down with Sequoia’s Doug Leone and Cyberstarts’ Gili Raanan to share brutally honest insights on startup recruiting, evaluating second-time founders,...
- 2025 / 6 / 24AI Producers, Tesla Robotaxis & the Rise of the “Tiny Teams” Era | E2142Today’s show:Tesla’s robotaxi launch, AI producers, job destruction, and smart toilets? In this episode of This Week in Startups, @Jason and @alex break down Tesla’s cautious rollout strategy, how AI is...
- 2025 / 6 / 21The Strip Mining Era of LLMs—And Why It’s About to End | E2141Today’s show:AI has been feasting on the open web—but is the free lunch over? In this explosive episode, @Jason and @alex call out OpenAI and others for “strip mining” the internet’s content without paying...
- 2025 / 6 / 18From Drones to Dystopia: The Future of Jobs, Fires & Meta’s AI Land Grab | E2140Today’s show:In this episode, @Jason and @alex explore how AI is reshaping the economy—from Pano AI’s $44M raise to fight wildfires with drones, to Amazon CEO Andy Jassy’s memo foreshadowing white-collar job...
- 2025 / 6 / 17Meta, Scale, and the Future of AI Labeling: Did Zuck Just Kill a Category? | E2139Today’s show:Meta just took a 49% stake in Scale AI, and the shockwaves are hitting the entire AI ecosystem. In this episode, @Jason and @alex unpack the deal’s implications: Google ($150M customer!) and...
- 2025 / 6 / 13Stripe’s Crypto Wallet, M&A Momentum, and Robots Replacing Soul-Crushing Jobs | E2138Today’s show:In this episode of This Week in Startups, @Jason and @Alex break down Stripe’s big bet on crypto wallets with its latest acquisition of Privy, the return of major M&A activity from Meta,...
- 2025 / 6 / 12TWIST VC Roundtable: Startup Valuations, Secondary Markets & the YC Revenue Illusion | E2137Today’s show: Alex moderates a TWIST VC Roundtable with Jason, Paige Doherty (Behind Genius), and Altimeter’s Megan Reynolds about the state of early-stage venture capital. They break down the rise of...
- 2025 / 6 / 10YC Valuations, VC Slowdown, and Office Hours with CustomerIQ | E2136Today’s show: Jason and Alex dive into why Y Combinator startups are raising at sky-high valuations with relatively low ARR—what does that mean for investors and founders? VC funds are slowing down and...
- 2025 / 6 / 7Circle’s IPO Soars, The Future of VC and Cursor’s Crazy Growth | E2135Today’s show: Jason and Alex dicuss stories shaping the tech and startup world: Circle’s explosive IPO and what it signals about crypto regulation and public market sentiment, the potential for tokenized...
- 2025 / 6 / 4Anthropic Cuts Off Windsurf, Deel Rewrites the Narrative and Flock Safety’s Surveillance Tech | E2134Today’s show: Alex and Lon discuss Windsurf getting abruptly cut off from Anthropic just before a rumored $3B acquisition by OpenAI, sparking questions around platform risk and foundation-model politics; Deel...
- 2025 / 6 / 2Grammarly’s $1B Round, Brain Computers, and NYT Licenses To Amazon | E2133Today’s show: Jason and Alex discuss the hottest tech and startup news: Grammarly secures a massive $1B investment from General Catalyst to fuel its AI ambitions and expand into deeper enterprise offerings; a...
- 2025 / 5 / 30How AthenaHQ and Browser Use Are Building the Next Layer of the Internet | E2132Today’s show: Alex interviews two cutting-edge startups shaping the future of AI: AthenaHQ, pioneering “GEO” (Generative Engine Optimization) to help brands rank in AI-powered search engines like ChatGPT and...
- 2025 / 5 / 28Google’s AI Design Tool, Salesforce’s $8B Comeback Deal, and M&A Momentum Builds | E2131In this episode, we cover three major stories shaping the startup and tech landscape. First, Google unveils Stitch, an AI-powered web design tool with one-click export to Figma—signaling a major disruption...
- 2025 / 5 / 23Apple’s Tariff Trouble, Anthropic’s New Models, and Our Founder Friday Finale | E2130Today’s show: Trump takes aim at Apple with a potential 25% iPhone tariff, Anthropic releases two powerful new Claude models claiming top performance in coding tasks, and two founders go head-to-head in the...
- 2025 / 5 / 22David Friedberg on AI-First Startups & the Future of Biology, Business & Creativity | AI Basics with Google CloudIn this episode, Jason chats with David Friedberg—CEO of Ohalo Genetics and co-host of the All-In Podcast—about how AI is transforming agriculture and startups. David introduces Ohalo’s "Boosted Breeding"...
- 2025 / 5 / 21Jony Ive Joins OpenAI, Waymo Hits 10M Rides, and How to Launch a Marketplace from Scratch | E2129Today’s show: Jason and Alex dicsuss Jony Ive's $6.5B deal with OpenAI and what it means for the future of AI hardware, Tesla’s push into robotaxis vs. Waymo’s 10M paid rides, and Microsoft’s latest move...
- 2025 / 5 / 20Drones, Design, and Digital Espionage | E2128Today’s show: Jason and Lon explore the wild edges of tech innovation and regulation — from a student-built acoustic weapon that takes down drones (without harming humans) to the legal gray areas of drone...