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
Podcast website
Latest episode
Jul 10, 2026
Where to listen?
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Episodes
Clawdbot is an inflection point in AI history | E2240 27.01.2026 1:02:15
This Week In Startups is made possible by: Quo - http://quo.com/TWiST Lemon IO - https://lemon.io/twist Northwest Registered Agent - https://www.northwestregisteredagent.com/twist Today's show: Jason is back from Davos and Tokyo! We are jumping right back in with a group of Clawdbot power users: Alex Finn, Matt Von Horn, and Dan Penguine. Clawdbot is a hot open source AI project that lets users a...
Why You'll Choose an AI Doctor (feat. Fred Almeida and Max Weiss) | E2239 24.01.2026 1:03:24
This Week In Startups is made possible by: Sentry.io - sentry.io/twist Hubspot - clickhubspot.com/twist2 Northwest Registered Agent - https://northwestregisteredagent.com/twist Today's show: One day soon, you might consult an AI general practitioner about your health, and then the computer will recommend human specialists to take up your case. On TWiST Tokyo, Jason chats with Fred Almeida — founde...
From Blood Transfusions to Burritos, How Zipline is Automating Delivery | E2238 21.01.2026 1:03:34
This Week In Startups is made possible by: Northwest Registered Agent - www.northwestregisteredagent.com/twist Crusoe Cloud - https://crusoe.ai/savings LinkedIn Jobs - http://linkedIn.com/twist Today's show: On today's TWIST episode, Alex interviews two of the top startup co-founders: Keller Cliffton of Zipline and Anastasis Germanidis of Runway. Zipline announced its $600 million raise at a $7....
How startups suddenly became "cool" in Japan (feat. Shin Takamiya of Globis Capital) | E2237 20.01.2026 57:36
This Week In Startups is made possible by: Circle.so - http://Circle.so/twist Deel - http://deel.com/twist Uber AI Solutions - http://uber.com/twist Today's show: Not long ago, promising young Japanese graduates wanted to go work for the largest, most established, and even oldest corporations: Sony, Mitsubishi, and the like. But now, just over the last few years, more and more Japanese people are...
Avoiding buzzwords and marketing-speak (feat. Thomas McInerney) | E2236 16.01.2026 1:03:26
This Week In Startups is made possible by: Lemon.io - https://lemon.io/twist Deel - http://deel.com/twist LinkedIn Jobs - http://linkedIn.com/twist Today's show: Some pitches sound just like ads… and it's a huge red flag for investors. On our latest edition of TWiST Tokyo, Jason welcomes legendary angel investor (and long-time friend of the pod) Thomas McInerney. His list of investments reads lik...
Japan's Startup Revolution (feat. Kathy Matsui) | E2235 14.01.2026 1:07:44
This Week In Startups is made possible by: Every.io - http://every.io/ LinkedIn Jobs - https://www.linkedin.com/twist Zite - http://zite.com/twist Today's show: Why do 40% of Japanese students want to build a company rather than join the corporate workforce? On TWiST, Jason considers this question along with special guest Kathy Matsui, general partner of the global VC fund MPower Partners. Their...
How to Make Billions from Exposing Fraud | E2234 13.01.2026 1:05:17
This Week In Startups is made possible by: Netsuite - https://www.netsuite.com/twist LumaAi - https://lumalabs.ai/twist Squarespace - https://squarespace.com/twist Today's show: Government fraud and waste has become a prominent issue in the last month. That's what we are looking at. On Today's episode of TWiST, Jason interviews Alex Shieh of the The Antifraud Company. Under the False Claims Act,...
Secrets of Startup Recruiting in the US AND Japan! (feat. Sho Takei) | E2233 13.01.2026 52:03
This Week In Startups is made possible by: Northwest Registered Agent - www.northwestregisteredagent.com/twist Caldera Lab - http://calderalab.com/TWIST Pipedrive - http://pipedrive.com/twist Today's show: TWiST is coming to you all from TOKYO as we launch Japan's first-ever Founder University! That's right, a full week of key insights from Japan's top founders, investors, and tech visionaries… w...
Jason's Top CES Products and Takeaways | E2232 10.01.2026 1:09:09
This Week In Startups is made possible by: Hubspot - http://clickhubspot.com/twist1 Circle.so - http://circle.so/twist Sentry - http://sentry.io/twist Today's show: On the last TWiST episode before Jason goes to Japan and Alex begins on paternity leave, the hosts break down the blockbuster tech news that is kicking off 2026. Discord AND Strava both eyeing billion dollar IPOs, two massive social m...
AI makes you more creative, AI Roundtable with Steven Johnson and Grant Lee | E2231 08.01.2026 1:06:30
This Week In Startups is made possible by: Gusto - https://www.gusto.com/twist Lemon IO - https://lemon.io/twist Quo - http://quo.com/TWiST Today's show: We keep hearing about how AI is killing our ability to think, filling our media with slop, and ruining our kids' ability to learn. It seems the internet is filled with negative sentiment about the future AI is bringing. Jason is joined by Grant...
2026 Starts with a bang: META AI Drama and Nvidia's $20B Groq Acquisition | E2230 06.01.2026 54:40
This Week In Startups is made possible by: Crusoe Cloud - https://crusoe.ai/build Uber - http://uber.com/twist Every.io - http://every.io/ Today's show: Jason and Alex are BACK on TWiST for 2026! This holiday season was anything but calm, with deca-corn acquisitions, massive Polymarket bets, and major new startups breaking from stealth! Jason talks the recent Nvidia-Groq $20B acquisition, a majo...
THE 2025 TWISTY AWARDS! Biggest Trends, Best Guests, Top Name Drops, and more | E2229 30.12.2025 55:49
This Week In Startups is made possible by: LinkedIn Ads - http://linkedin.com/thisweekinstartups Squarespace - https://squarespace.com/twist Hubspot - http://clickhubspot.com/twist1 Today's show: We're saying goodbye to 2025 with our annual TWISTY Awards, looking back on our favorite pod moments from throughout the year. Featured clips include Jason's message to the members of Reddit's r/AntiWork...
Jason's ultimate dream mega-purchase + Founder Q's | E2228 29.12.2025 45:04
This Week In Startups is made possible by: Northwest Registered Agent- https://www.northwestregisteredagent.com/twist Vanta - http://www.vanta.com/twist Lemon IO - https://lemon.io/twist Today's show: Jason's already a millionaire many times over… but what are the huge, blockbuster, dream purchases that he's still holding off on? BESIDES the private jet we all know he wants? The Noti Gang has ask...
Waymo Madness in SF! Why robotaxis clogged the streets | E2227 23.12.2025 59:36
This Week In Startups is made possible by: Caldera + Lab - http://calderalab.com/TWIST Crusoe Cloud - https://crusoe.ai/build Uber - http://uber.com/twist Today's show: Why did a power outage in the Bay Area cause Waymos to pile up on city streets? Jason was actually in San Francisco to take in the spectacle of Waymos blocking traffic. But why did this happen? And can we look forward to a day whe...
Level up your copywriting w/ Sam Parr | E2226 20.12.2025 1:06:14
This Week In Startups is made possible by: Luma AI - https://lumalabs.ai/twist Northwest Registered Agent - https://www.northwestregisteredagent.com/twist Lemon IO - https://lemon.io/twist Today's show: DID YOU KNOW… most of the tried and true techniques devised by marketing gurus in the '40s and '50s still apply today? On TWiST, we're joined by online marketing expert Sam Parr, host of "My Firs...
INSIDE How AI Startups hire, AI Roundtable with Wade Foster, Mikey Schulman, and Ali Ansari | E2225 18.12.2025 1:26:46
This Week In Startups is made possible by: LinkedIn Ads- http://linkedin.com/thisweekinstartups Squarespace - https://squarespace.com/twist Enterpret - http://Enterpret.com/twist Today's show: How do top tech CEOs hire? AI has thrown out the playbook for getting hired — so what are the most innovative firms looking for? Anyone can learn any skill and automate much of it, what is to be valued in t...
Is this the end for the Roomba? Why iRobot went bankrupt | E2224 16.12.2025 1:00:43
This Week In Startups is made possible by: Vanta - https://www.vanta.com/twist NetSuite - https://www.netsuite.com/twist Lemon.io - https://lemon.io/twist * Today's show: Domestic robots have never been hotter… so why is iRobot in so much trouble?! On TWiST, we're investigating the recent troubles facing the automated vacuum robot, Roomba. We've all seen these little discs sweeping up our friends...
Disney and OpenAI sign landmark deal… and we saw it coming! | E2223 13.12.2025 57:59
This Week In Startups is made possible by: LinkedIn Ads - http://linkedin.com/thisweekinstartups DevStats - https://www.devstats.com/twist Crusoe - https://crusoe.ai/build Today's show: FINALLY, you can hang out with Kylo Ren and Olaf the Snowman… thanks to the magic of AI. On TWiST, we're digging into the mega OpenAI-Disney deal. Mickey is giving Sam Altman a $1 billion investment AND will allow...
"The best founders find a way to make it happen": VC Roundtable with Bryan Kim and David Clark | E2222 11.12.2025 1:10:26
This Week In Startups is made possible by: Uber - http://uber.com/twist Pilot - https://pilot.com/twist Northwest Registered Agent - https://www.northwestregisteredagent.com/twist Today's show: Boom is still making supersonic jets but ALSO plans to start selling their turbines as power sources for AI data centers. It's a perfect example of problem-solving on the go and how "the best founders… MA...
FLASHBACK: The future of remote work, juggling APIs, and dream integrations with Wade Foster of Zapier | E2221 10.12.2025 1:17:20
This Week In Startups is made possible by: Goldbelly - Goldbelly.com Every.io - http://every.io/ Zite - zite.com/twist Today's show: Today, Zapier's a multi-billion company helping enterprises integrate AI agents and other time-saving shortcuts into their workflows… but we had the founder on TWiST when they were just getting started! In a 2016 chat, founder Wade Foster walked JCal through their 20...
What's REALLY going on with those "ads" in ChatGPT | E2220 09.12.2025 1:02:25
This Week In Startups is made possible by: Superhuman - https://superhuman.com/podcast Squarespace - https://squarespace.com/twist Enterpret - https://www.enterpret.com/dlp/this-week-in-startups Today's show: A screenshot showing a "Target Ad" in ChatGPT results went viral… over the weekend, but the OpenAI chatbot has NOT actually opened the advertising floodgates just yet. As ChatGPT staffers we...
Netflix buys WB + why Jason should run Disney | E2219 06.12.2025 1:02:30
This Week In Startups is made possible by: Sentry - http://sentry.io/twist LinkedIn Ads - http://linkedin.com/thisweekinstartups Pipedrive - pipedrive.com/twist Today's show: Netflix wants to gobble up Warner Bros. Do they just want to own Batman and Harry Potter, or is this secretly about destroying movie theaters? Sure, this is usually a startup show, but news THIS BIG warrants attention! So Lon...
Getting past the "Cardinal Sins of Delegating" with Jonathan Swanson of Athena | E2218 04.12.2025 57:12
This Week In Startups is made possible by: Northwest Registered Agent - https://www.northwestregisteredagent.com/twist Crusoe - http://crusoe.ai/build Gusto - https://www.gusto.com/twist Today's show: Delegating is its own unique skill, requiring training and a real investment of time and attention. On TWiST, Jason chats for a full hour with the founder of one of his favorite startups, Athena, whi...
Monumental Makes Construction Bots Play Nice Together | E2217 03.12.2025 1:25:55
This Week In Startups is made possible by: LinkedIn Ads - http://linkedin.com/thisweekinstartups Vanta - https://www.vanta.com/twist Pilot - https://pilot.com/twist Today's show: Did you know there's actually a shortage of US bricklayers? It's TRUE! So feel free to marvel at Monumental's brick-laying robots. They're not putting anyone out of work, but filling a much-needed gap. Join Alex and Monu...
Is $MSTR over? Jason takes his victory lap. | E2216 02.12.2025 57:41
This Week In Startups is made possible by: Quo - http://quo.com/TWiST Squarespace - https://www. Squarespace.com/TWIST Miro - http://miro.com/ Today's show: Michael Saylor's Strategy play is struggling with the price of Bitcoin on a steep decline… Is his new "dollar reserve" the answer? On TWiST, we're looking into the state of $MSTR and why Jason remains SO skeptical about this increasingly conv...
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