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Jason Calacanis
This Week in Startups
Technology
English
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.
Website
Episodes
300
06 November 2025
Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204
Register for Founder University Japan’s kickoff! https://luma.com/cm0x90mkToday’s show:*On TWiST, Jason welcomes an all-star VC panel — Deedy Das of Menlo Partners and Jay Eum of GFT Ventures — for a deep dive into the shocking scale of early-stage AI raises, a transitional moment for investors, the growing importance of the “prosumer” market, ChatGPT’s insane smile curves, and much much more.IN...
1 h 23 min
03 November 2025
Sending datacenters into orbit | E2203
👉 Register here to join the Founder University Japan kickoff! https://luma.com/cm0x90mkToday’s show:*Starcloud has started sending AI chips into orbit. So is this where the datacenters the power AI will one day live? And does wifi work in the vacuum of space? We’re asking the TOUGH questions.PLUS Jason and Alex are doing a deep dive on all this week’s OpenAI news. Will they ever be able to pay...
1 h 17 min
01 November 2025
What will be OpenAI’s IPO price? Place ya bets! | E2202
What will be OpenAI’s IPO price? Place ya bets! | EXXX*Polymarket’s sharps are already placing bets on when ChatGPT maker OpenAI will go public… and Jason and Alex want in on this action. They’re placing side wagers on how the House that Sam Altman built will be valued once it finally goes public.PLUS find out why Amazon is Jason’s stock pick for the next five years… Why startups are starting to...
1 h 18 min
30 October 2025
Grammarly is now Superhuman! CEO Shishir Mehrotra explains the rebrand | E2201
Today’s show:*Why rebrand an app with 40 million daily active users?On TWiST, Grammarly CEO Shishir Mehrotra swings by to explain why he’s renaming his company after the mail app he just purchased, Superhuman.Plus he’s giving us a first look at the startup’s new AI assistant, Superhuman Go, digging into their new agent-centered strategy, looking ahead at the potential for AI job displacement, and...
1 h 38 min
29 October 2025
iPhone Air is “inspiring,” and a first step toward Apple Glasses (w/ Zach Handshoe of SpatialGen) | E2200
Today’s show:Jason’s been skeptical on Apple lately, but he’s BLOWN AWAY by his new iPhone Air.Hear why JCal thinks Cupertino’s latest release is “completely inspiring,” and why he’s sure it’s the next step on the road to Apple Glasses.We’re chatting with LAUNCH founder Zach Handshoe of spacial video startup SpatialGen about designing products for Cupertino AND the intense pressure of performing...
1 h 18 min
28 October 2025
Jason Unpacks Sequoia’s New Funds | E2199
Today’s show:Australia has accused Microsoft of employing a dark pattern… Hear why Jason says these kinds of sneaky tactics aren’t usually worth it.It’s a brand-new Monday TWiST and it’s PACKED with news. In addition to Australia’s allegations against MSFT, we’re looking at Chinese drone fails and wondering how live experiences will change in the age of AI.PLUS has Tesla finally “solved” FSD...
1 h 21 min
25 October 2025
If you’re not working 9-9-6, are you working hard enough? | E2198
Today’s show:*Working from 9 am to 9 pm, 6 days a week, might seem like TOO INTENSE a commitment for some, but Jason argues that elite performance — and the mega-compensation that goes along with it — sometimes requires personal sacrifice. While 72-hour weeks might lead to burnout for some, it really comes down to individual choice.PLUS Jason and Alex deep dive the NBA gambling scandal and the...
1 h 1 min
22 October 2025
Amazon’s “Age of Efficiency,” LLM distribution, AI wearable worries, and more with Elad Gil | E2197
Today’s show:*Amazon’s dropping a LOT of employees for AI and robots… are Jason’s darkest predictions coming true?Legendary investor Elad Gil joins Jason and Alex for the full show today! Together, they’re digging into the Amazon news, looking back at Jason’s predictions from just last month, and theorizing about just how many people will lose their jobs to computers, and what we’re going to do...
1 h 23 min
22 October 2025
Magic School uses AI to help kids learn, not cheat | E2196
Are AI tools in the classroom just time-savers, or can they have genuine educational value?In a must-watch TWiST 500 interview, Alex chats with Magic School founder (and former principal) Adeel Khan about how AI tools can make teachers more effective, and keep students inspired, without just doing all the work for them. He talks about turning an AI chatbot into a true assistant teacher, that...
57 min
21 October 2025
Just how frothy is the AI Bubble anyway? | E2195
Today’s show: *Is the AI bubble going to POP? And if so, how much of our economy is it going to take down with it?On a new TWiST, Jason, Alex, and Lon debate the size and scale of the AI bubble, whether poppage is imminent, and just who we can blame for the last few economic crises. (HINT: Not the tech industry!)PLUS why Jason STILL thinks the current AI cycle will be the biggest in tech history,...
59 min