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 / 9 / 27Is there an AI coding bubble? Plus Meta’s new SlopTok product, Neon’s divisive app shuts down, and more | E2184Today’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...
- 2025 / 9 / 25The rise of “workslop,” Alibaba’s insane new deepfake model, Tether’s MASSIVE valuation, and more | E2183Today’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...
- 2025 / 9 / 23Jason’s H-1B pitch, the latest on the TikTok deal, and Howie’s first ad | E2182Today’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...
- 2025 / 9 / 19Meta’s “creepy” new Ray Bans, Beehiiv teams with Discord, AND a visit from Lovable CEO Anton Osika! | E2181Today’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...
- 2025 / 9 / 18Who Owns the Output? AI Copyright & IP Explained w/ Chris Paniewski | Startup Legal BasicsToday’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...
- 2025 / 9 / 17Tesla and Uber team up! Plus Weave Robotics’ Isaac and $OPEN bull Eric Jackson | E2180Today’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...
- 2025 / 9 / 16Why Medium is HIDING from AI | E2179Today’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...
- 2025 / 9 / 15Robinhood Venture Fund, Polymarket adds earnings, and LAUNCH Accelerator 35 is here! | E2178Today’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...
- 2025 / 9 / 13All-In Summit Highlights, Schools Could Block Social Media, FTC Chatbot Investigation, and Zoox hits Vegas | E2177Today’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...
- 2025 / 9 / 11AI Copyright & Training Data w/ Chris Paniewski | Wilson Sonsini Startup Legal BasicsJason 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...
- 2025 / 9 / 10Republic opens private markets as Positron takes on GPUs: A TWiST500 doubleheader! | E2176Today’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...
- 2025 / 9 / 9How Founders Are Building the Next Great Startups | Paid.ai, iTruckr & Tenax AI | E2175Today’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...
- 2025 / 9 / 5The Browser Wars heat up! PLUS, Khan on The Bulwark, rules for great domain names, and Polymarket returns | E2174Today’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...
- 2025 / 9 / 4Creative Structures w/ Becki DeGraw | Wilson Sonsini Startup Legal BasicsToday’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...
- 2025 / 9 / 3Uber, Lucid & Nuro team up on robotaxis by 2026 | E2173Today’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...
- 2025 / 9 / 3Jason’s Tesla Optimus prediction, Anthropic’s latest mega-raise and more | E2172Today’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...
- 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,...