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.

Sending datacenters into orbit | E2203

👉 Register here to join the Founder University Japan kickoff! https://luma.com/cm0x90mk * Today’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 back all these GPU purchases? What happens to the wider economy on the off chance they don’t thrive? And what’s with these rumors that ChatGPT has stopped giving medical or legal advice? All that and a look at TrustMRR (and why Jason advises you not to publicly share your Stripe), why Jason thinks Netflix should buy CNN, our hosts favorite Nazi hunter movies, and MORE.

What will be OpenAI’s IPO price? Place ya bets! | E2202

*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 release their own foundation models, and what this means for major players like OpenAI and Anthropic… AND Producer Oliver stops by with an in-depth look at the music-generating Suno app.

Grammarly is now Superhuman! CEO Shishir Mehrotra explains the rebrand | E2201

In this episode, Alex Wilhelm, Jason Calacanis, and Shashir Mehrotra explore evolving work culture, highlighting employee care, company culture, and four-day workweeks. They examine small company efficiency and compare market leaders' work cultures. Shashir introduces Superhuman Go, focusing on AI assistants and personalization in productivity. They tackle audience questions on pricing, style, and privacy, and discuss NVIDIA's market cap, OpenAI's revenue, and Microsoft's investment in OpenAI. The conversation also covers autonomous vehicles, robotics, economic insights, and previews upcoming big tech earnings and AI discussions.

Jason Unpacks Sequoia’s New Funds"| E2199

In this episode, we dive into hyperscaler earnings and AI's role in cloud computing. We explore holiday season predictions and trends in online learning investments, addressing AI-generated fraud concerns. Discover how AI tools analyze earnings calls and the growth of drone shows globally. Learn about Tesla's synthetic data training for Full Self-Driving and new partnerships in autonomous driving. We also discuss media bias, Sequoia Capital's latest funds, and the effect of political statements on startups. Finally, we update on the AI trading competition, Microsoft's AI pricing strategy, and ethical business practices, wrapping up with a call for listener feedback.

If you’re not working 9-9-6, are you working hard enough? | E2198

This episode explores the intersection of sports, betting, and technology, beginning with insider information on LeBron James' injury and its implications for betting and fantasy sports. The discussion shifts to a poker cheating scandal involving NBA figures, examining the legality and monitoring of high-stakes celebrity games. The episode also touches on China's demanding 996 work culture and features insights from Presh on storyboarding methods. Anthropic's deal with Google highlights AI infrastructure investments, while cloud infrastructure's evolution is analyzed through Dropbox's history and David Heinemeier Hansson's views on AWS spending. The episode concludes with a cost-benefit analysis of cloud providers.

Amazon’s “Age of Efficiency,” LLM distribution, AI wearable worries, and more with Elad Gil | E2197

In this episode, Jason Calacanis and Elad Gil explore the startup and AI landscape, discussing efficiency, revenue growth, and AI's role in book translation and computing. They examine AI's energy costs, Middle East startup ecosystems, and Nivan's IPO journey. The episode also covers AI's impact on enterprises, Amazon's automation, workforce implications, and AI's future in consumer tech and finance. They touch on regulatory debates in AI and tech acquisitions, wrapping up with insights on AI regulation compared to other industries.

Just how frothy is the AI Bubble anyway? | E2195

Jason, Alex, and Lon engage in a lively discussion on the potential existence of an AI bubble, examining historical patterns of economic bubbles and the roles economists and bankers play in these scenarios. They delve into signs of an AI investment bubble, exploring corporate spending and market frothiness, while debating if this cycle could be the greatest in tech history. The episode also covers the AWS outage's impact, strategies for multi-cloud resilience, and the challenges of verifying AI-generated content amidst misinformation. Additional topics include Zuckerberg's investment insights, large-scale protests, and AI's role in market trading. They wrap up with thoughts on cultural impacts of Aaron Sorkin's sequel to "The Social Network".

Deel’s growth overshadows SpyGate, Claude learned new skills & the “momentum is moat” debate | E2194

In this episode, we dive into market chaos and business strategies. Jason discusses the ski season and Open Snow app, and a shift to short, direct calls amid market changes. The team explores AI's expanding opportunities and the potential for trillion-dollar AI companies. They analyze Deel's $300M raise and its industry impact. Roloff Botha joins to discuss venture capital dynamics. We cover startup valuation, growth prospects for Rippling and Deel, and capital strategies. Anthropic's AI skills and applications are highlighted, along with collaboration in LLMs. Jason shares his health journey, and the episode wraps up with a focus on startups, AI, and data balance.