Disney and OpenAI sign landmark deal… and we saw it coming! | E2223

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 is copyrighted characters to appear in Sora and ChatGPT images. Of course, Jason predicted this would happen WAY BACK during the summer months and even showed off his “Darth Calacanis” creation on the “All-In Podcast.” PLUS Amazon has been launching and pulling AI features from Prime Video… what gives? Jason’s predictions on the coming AI blowback and who’s on what side. Why he’s so focused on Education, Health Care, and Housing as issues. AND why founders should always take calls from Big Companies, even if it might just be a fishing expedition. It’s a new Friday TWiST! Check it out!

“The best founders find a way to make it happen”: VC Roundtable with Bryan Kim and David Clark | E2222

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… MAKE IT HAPPEN.” Join us for another insightful VC roundtable episode, featuring special guests Bryan Kim (a16z) and David Clark (Ven Cap). They’re discussing why Boom’s turbine announcement is about necessity AND opportunity PLUS… - Why we might NOT be in an AI bubble after all - Promoting your startup without spending your entire runway on marketing - Why founders need to be RELENTLESS - Bill Gurley’s classic response about Uber’s Total Addressable Market - AND LOTS MORE

FLASHBACK: The future of remote work, juggling APIs, and dream integrations with Wade Foster of Zapier | E2221

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 2012 seed round, running a small entirely remote team with no HQ, the complexities of building a tool that relies on third-party APIs, and why Microsoft Office was the “Holy Grail” for his integration software. PLUS we’ve got a new entrant in your Gamma Pitch Deck competition! Tour CEO/CTO Amulya Parmer tells us how his app is saving property managers time and grief, while eliminating “looky-loos” and increasing their “hit rate.” FINALLY, Alex chats with Tomas Puig of TWiST 500 marketing analysis startup Alembic. It turns out, LLMs aren’t ideal for scrutinizing marketing campaigns because they lack the requisite historical data. Find out how they’re using Spiking Neural Networks (SNN) to dig deeper than GPT and Claude can go.

What’s REALLY going on with those “ads” in ChatGPT | E2220

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 were quick to explain on social media, this was actually an invitation for a user to integrate their Target account into ChatGPT, for an easier agentic browsing and shopping experience. But it does prompt Jason and Alex to ask some intriguing questions… Is OpenAI just waiting for Google or someone else to launch AI ads first, and face the inevitable flood of backlash they’ll presumably receive? Is there someone at OpenAI already thinking DEEPLY about how these in-feed ads should work? And what does this mean for their wager on when ChatGPT is going to actually get ads? Is that already decided?

Netflix buys WB + why Jason should run Disney | E2219

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 stops by to tell Jason and Alex about the big Netflix acquisition news, why so many theatrical movie fans are terrified for the future, and why this might face particular regulatory scrutiny both at home and abroad. PLUS… are Googlers gaming Polymarket? This is one scenario in which prediction markets are NOT exactly like stocks. THEN we’re looking at some of our favorite startups from the Fall ‘25 Y Combinator cohort (and asking Producer Claude for his picks)… Considering why Perplexity keeps getting sued and how they can stop it… and doing a victory lap for Jason’s early investment in breakout AI training project Micro1.

Getting past the “Cardinal Sins of Delegating” with Jonathan Swanson of Athena | E2218

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, which trains online assistants and pairs them with busy founders and executives. (Jason has 2!) But getting the MOST out of your executive assistants is less obvious than it looks. Jonathan unpacks some of the secrets to “Black Diamond Delegating,” and how he manages to keep 6 different high-level helpers operating at once. Plus, Jason and Jonathan look back at the Open Angel Forum days, where Jason invested in Jonathan’s previous company, Thumbtack, praise the “Checklist Manifesto,” discuss the telltale signs you’ve achieved market pull, and lots more insights.

Monumental Makes Construction Bots Play Nice Together | E2217

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 Monumental founder/CEO Salar al Khafaji for a deep-dive on how the startup is making construction robots play nice together by maintaining separate “zones” of operation, why Salar thinks startups need to focus on truly complex, real-world problems to truly blossom, and the secrets of fundraising in Europe. PLUS Alex chats with Seasats CEO Mike Flanigan about designing the next generation of autonomous marine crafts. (That is to say, ocean drones.) From their home base in San Diego, the company is trying to get completely independent of all Chinese parts.

Is $MSTR over? Jason takes his victory lap. | E2216

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 convoluted financial scheme. Is CNBC giving Michael Saylor a pass? Is that why he won’t go on “All-In”? And do investors realize that loans go BEFORE equity? We’re asking the TOUGH questions… PLUS Jason’s Four Red Flags for companies with convoluted tactics… Why S&P Global downgraded Tether, and why Jason thinks the US government waited TOO LONG to pass stablecoin regulations… Jason reacts to the NYT “hit piece” on Bestie David Sacks… we’re checking out the new Matic robot vacuum and Sunday Robotics’ Memo bot… PLUS much more of the day’s biggest tech news and stories.

SO MANY THINGS need to go right just so you can watch a TikTok! | E2215

On TWiST, Alex is chatting with Neubird CEO Gou Rao about the intricate complexity of IT Ops, and the vast amount of layers and components that have to be delivered very quickly to your phone in order to stream a simple video clip. Neubird has developed Hawkeye, an AI “engineer” that uses “context engineering” to isolate and troubleshoot problems, while still keeping costs down. Loading up a video to show your friends may SOUND straightforward, but it’s actually, as Alex notes, a miracle anything on the internet works at all. PLUS we’ve got Subject AI CEO Michael Vilardo stopping by to tell us how the app uses gamification to keep kids learning and engaged. NOTE TO FOUNDERS: Mike got invited on the show because he sends email updates to his “dream investors,” including Jason. It’s a solid best practice!

Even great startups sometimes need to pivot (feat. Francisco Cornejo of Theo) | E2214

Today’s show: The team from Familify had released a well-reviewed storytelling app for kids and parents… but it just wasn’t growing! Then they noticed that Bible stories and faith-based content was particularly popular. So they decided released a brand new app, Theo, just for these sorts of lessons and stories. And the new product overtook Storybook in just a few weeks! It’s a vital lesson for founders… Even if you succeed, you may be able to succeed EVEN MORE. Remain flexible and open to strong new ideas (especially if, like Francisco, your wife suggests them!) PLUS we’re chatting with Collin from En Vérité about how AI can make do diligence much less painful for investors AND checking out our latest Gamma Pitch Deck competitor. Find out why Jason says Jake Triton from Pitch Prfct might just be closing in on Product Market Fit.

Jason predicts a “major M&A moment” in the next six months! | E2213

Today’s show: Google and Meta had their cases dismissed (or received a slap on the wrist)… Despite all the backlash and cynicism, AI companies continue making bank and releasing hot new products… What does it all mean? For Jason Calacanis, the signs are pointing to a “major M&A moment,” with huge opportunities for increased efficiency and consolidation among America’s favorite brands and largest companies? Who will it be? Join Jason and Alex for a round of hot speculation. PLUS why Jason thinks Michael Burry is both right and wrong about GPU depreciation, why NOTHING is certain about these OpenAI mega-deals, Google’s Nano Banana Pro can make infographics and they’re VERY impressive… and much more.

Why data is the biggest AI bottleneck (feat. Arthur Mensch of Mistral AI) | E2212

Today’s show: The race for more compute gets all the headlines, but Mistral AI CEO Arthur Mensch tells us the REAL danger is running out of data! On TWiST, Jason and Alex are chatting with the head of France’s largest foundation AI company, Mistral AI, about how enterprises can get more out of their AI pilots, whether the West is lacking leadership on open-source, why Mistral AI isn’t pursuing every possible kind of AI application, and optimizing your models for performance rather than benchmarks (aka benchmaxxing). Find out what it’s like to run a huge AI company in today’s intense environment! PLUS… why everyone made the wrong call on OpenAI vs. Google… Kraken’s fresh $20 billion valuation… Jason’s urgent message to every company thinking about M&A… and much more!

AI Model Showdown: Grok 4.1 vs. Gemini 3 | E2211

Today’s show: Will the arrival of two hotly-anticipated, intensely powerful AI models snap the Doomer cycle? On a new TWiST, Jason and Alex consider the current AI landscape, one where cynicism about insider mega-deals, fear of job displacement, and concerns about bubble bursts seem to rule the day. Will the arrival of two powerful new models — xAI’s Grok 4.1 and Google’s Gemini 3 — help the industry to course-correct? And how do we decide how much these models have improved anyway? PLUS we’re investigating Cloudflare’s recent downtime and their acquisition of Replicate. Are we heading toward a future in which everyone runs their own models, locally? And how worried should founders get if their products or sites go down for a few hours? Finally, if you’re an investor, and want to come to Jason’s Dim Sum Demo Day in San Francisco, here’s the link: http://launch.co/dimsum

Archer buys an airport, Ramp’s huge raise, RIP KitKat, Bezos returns to the C-Suite, and more | E2210

Are we finally reaching Peak eVTOL? Jason and Alex on Joby’s big Abu Dhabi moves and Archer’s purchase of LA’s Hawthorne Airport. On a PACKED Monday TWiST, Jason is BACK from MENA and Tokyo. Hear tales from his whirlwind trips launching new Founder University satellite programs… and find out why construction and fintech are BOOMING across the Middle East. PLUS Ramp raised $300M… here’s why Alex calls the round “pretty baller.” We question why AI companies are growing SO MUCH FOUNDER than their SaaS counterparts. We’re digging into the Problem with Dropbox. AND we’re saying goodbye to KitKat, the beloved SF bodega cat who was reportedly run over by a Waymo.

Stop ghosting your friends with Nox’s RPLY, plus Alloy Automation and a Shopify flashback | E2209

Today’s show: Nox’s new app RPLY reminds you to text your friends back, getting you to iMessage inbox zero. On today’s TWiST, we’ve got Molly Cantillon of Nox, telling us how she plans to make lackadaisical texters (like our co-host Alex) more effective, even if it means breaking into Apple’s walled garden. Hear about how RPLY maps your relationships so that it can understand your messages contextually, and help you stay organized. Then, Gregg Mojica of Alloy Automation swings by the show to dispel some common myths about AI agents. For the most part, these little machine learning helps aren’t truly autonomous… Hear how Alloy’s agents decide when it’s time to bring in a human for help. PLUS is AI in a “lull” right now? Hear why Gregg thinks there’s still a LOT of room for these apps to improve.

Why We Need Ferries and Tugboats in Space w/ Orbital Operations | E2208

Today’s show: Just getting our stuff into orbit isn’t enough… Orbital Operations wants to help companies take things HIGHER. In today’s TWiST 500 interview, Alex chats with Ben Schleuniger, whose startup Orbital Operations is solving the complexity of space logistics. The advent of reusable rockets has made it easier and cheaper than ever for us to place objects in Low Earth Orbit (or LEO). But what if we want to reach higher orbits? That’s a much more challenging issue: space is already kind of CROWDED, and not all of our vehicles can carry enough fuel to power them that far out into the cosmos. Orbital’s fix? Cryogenic orbital maneuvering vehicles (or OMVs) like the Astraeus, which uses hyper-efficient propulsion systems, allowing them to travel further and faster speeds, and even potentially get refueled in orbit.

Inside Harvey AI’s $8 billion AI lawyer app, PLUS How OpenRouter unites the LLMs | E2207

Today’s show: On today’s TWiST, Alex takes a deep dive into LLM Law with Harvey AI co-founder/president Gabe Pereyra. It turns out, much like software development, doing legal work relies on learning specialized language and sifting through a dense and expansive corpus of information… making it an IDEAL use case for LLMs. Buuuuut AI works so fast… the current structure of legal payments (billable hours) no longer applies. Find out how Harvey is working around these challenges — and what they plan to do if OpenAI decides to get into the legal game — in this fascinating interview. THEN, Alex chats with another AI visionary — OpenRouter co-founder and CEO Alex Atallah — who allows developers to plug and play all the major models into their applications.

IPO Mania hits the TWiST 500! Three companies are ready to go public | E2206

Today’s show: *Three of our favorite TWiST 500 startups — Ledger, 1Password, AND Mercury — are circling IPOs. Find out why the cybersecurity space remains so hot… AND why Jason says you really need to have multiple banks. PLUS Marc Andreessen called The Pope an AI Doomer on X, then thought better of it. We’re tracking the entire viral controversy… SPEAKING OF viral feuds, allegations are FLYING around about recently-funded AI agent makers Giga. Does the startup pose some genuine red flags, or was it just a questionable launch video? AND why Alex and Jason remain optimistic the AI vibes could turn around, presentation maker Gamma is growing FAST, plus an update on Jason and Alex’s Polymarket IPO wager…

It’s a boat, it’s a plane, it’s REGENT’s Seafarer | E2205

Today’s show: *The key to avoiding long airport delays? Low-altitude sea planes! Why didn’t you think of that? We’ve got an awesome line-up of TWiST 500 founders giving us an inside glimpse inside their startups on this Friday special edition. FIRST: Billy Thalheimer of REGENT introduces us to their aircraft/boat hybrid The Seaglider, and walk us through how it all works, AND why they’re operating in BOTH the commercial and defense sectors from their Rhode Island HQ. THEN, we’ve got Convexia co-founder Ayan Parekh showcasing how they’re using a collective of specialist AI agents to exploit other pharma labs’ leftovers and turn them into new drugs and treatments for rare diseases. FINALLY, Hunter Leath of Archil joins the show to tell us why efficient utilization of cloud data remains a surprisingly complex, and unsolved problem. His solution? Caching-as-a-Service! Find out how it all works, and why pre-caching is SO difficult to do, in this TWiST exclusive chat.

Is investing REALLY the hardest job in tech? A TWIST VC Roundtable (ft. Deedy Das and Jay Eum) | E2204

In this episode, Jason Calacanis is joined by Didi Doss and Jay from GFT Ventures to explore the shifting landscape of venture capital and startup ecosystems. They delve into Sequoia's leadership change and Roloff Botha's legacy, discussing the evolution of capital allocation and the rise of global decacorns. The panel examines the increasing expectations for pre-seed funding, the disparities in venture funding, and the challenges of overpaying while ensuring returns for LPs. They also touch on the impact of AI on customer retention and the growth of companies like Anthropic and OpenAI. The episode wraps with insights into the rise of AI-generated content and storytelling in startup marketing.