GPT-5 comes alive, Apple is struggling, and Ripple bought Rail | E2162

Today’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 obsessive innovator. Speaking of new products, GPT-5 is here and the hosts are… not exactly blown away. Are we in the midst of the AI trough of despair? PLUS we’re talking Ripple’s acquisition of Rail, Donald Trump’s new AI chatbot, Bumble’s new direction, Airbnb’s potential paths forward and MUCH MUCH MORE.

Chinese coffee hits NYC, RIP Hulu, GPT-5 arrives and more | E2161

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 biggest tech and startup news of the day, including Disney’s decision to sunset Hulu, OpenAI’s new open-weight models, the Cloudflare vs. Perplexity feud, Uber’s newly-announced stock buyback, China’s Luckin Coffee coming to Manhattan, and much much more!

TWiST 500 interviews with Cortical Labs, Turing, AND Mercor | E2159

Today’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’ first-ever commercial computer running on living human cells. - Turing founder Jonathan Siddarth unpacks the secrets of LLM benchmarking, and explains why even our most advanced tests need to get much much harder right away. - Finally, Mercor founder Brendan Foody on how AI is about to reinvent the hiring process, and marrying the effectiveness of recruiters with the ease of online job boards. It’s three — count ’em, three — can’t miss TWiST interviews guaranteed to make you smarter

All Star Investor Panel! Sophia Amoruso and Ryan Hoover | E2158

Today’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 current environment for startups, founders, and investors. How do tell durable from brittle revenue… Everyone’s different approaches to follow-on investments and recycling… Strategies on when to trim a position… The benefits of hosting co-working events and jam sessions… And LOTS LOTS more! It’s an essential watch for anyone building or investing in companies in 2025!

Figma IPO, IMAX AI Festival, the Tea app spill, that one Sydney Sweeney jeans ad, and more! | E2157

SYDNEY SWEENEY’S AMERICAN EAGLE AD DIVIDES OUR PANEL! PLUS WHAT STARTUPS CAN LEARN FROM THE VIRAL ASTRONOMER RESPONSE Jason, Alex, and Lon are looking at some of the biggest media stories of the day before returning to their favorite topic, tech. Tune in for deep dives on IMAX’s new AI film festival, Figma’s big IPO and much more!

Behind the scenes at the ALL-IN AI SUMMIT w/ POTUS, JD Vance, Jensen Huang, Lisa Su, and more… | E2156

Today’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 Sec. Wright for dismissing solar power. THEN Jason and Alex talk about the immense promise of open-source robotics and check out Hugging Face’s Reachy… PLUS picking apart the White House’s new AI-related executive orders, why Jason is afraid of China repeating its Huawei success, a free exchange about tariffs vs. free trade, AND a pressing query from a founder on Reddit: how bad is it to add AI to your product too early?

AUTOMATING HEALTH CARE, THERMODYNAMIC COMPUTING, AND PRODUCT VELOCITY | E2155

Today’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 AI is making the entire health care industry more streamlined. THEN Gill Verdon from Extropic AI unpacks deterministic vs. probabilistic computing, and how thermodynamics can make everything from robots to VR more effective. FINALLY, Tyler Denk from our fav newsletter platform Beehiiv walks us through their future roadmap, and explains why they’re adding new features SO OFTEN. It’s a packed episode full of fresh insights for founders. Check it out!

Manufacturing in the US, Building in Open Source… and more | E2154

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 in the USA, and why the loss of EV tax credits might not hurt the business as much as you’d think… THEN, we’re talking to James Hawkins of PostHog about how keeping his burn rate low opened up a wealth of new opportunities for his company… THEN Yoshi Yokokawa from Alpaca HQ stops by to talk about working in a category that’s no longer the hottest thing in the Valley (like fintech) and the importance of stable coins to his business model. You won’t want to miss this one! Tons of fresh and important insights for founders.

Inside Substack’s $100M Push to Fend Off Beehiiv | E2153

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 of these rival platforms, plus Patreon and more. PLUS they’re digging into Lovable’s latest raise and what it says about the current economics of vibecoding, surveying the automated driving landscape in light of Uber’s new agreement Lucid and Euro, explaining Jason’s “meme processing” theory of internet humor, AND looking ahead to Christopher Nolan’s IMAX epic “The Odyssey.” Join us for the longest-running and most in-depth podcast on Earth for startup founders.

Thinking Machines’ RECORD seed round, VC Geoff Lewis, and MORE | E2152

Today’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 Lewis, a look inside the HUGE seed rounds being commanded by early-stage AI startups, crunching the numbers on how much compute data centers need to sell before they’re profitable, Polymarket asks who will be the next CEO of X and MUCH MUCH MORE. Join us for the longest-running and most in-depth podcast on Earth for startup founders.

# **Blitzhiring and the Complicated Case of Windsurf, OpenAI and Google | E2151** *

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 out in real-world startups.Plus Jason’s short- and medium-term predictions for AI’s impact on the job market, Tesla’s latest expansion of its Austin robotaxi service, Mistral giving the EU a real stake in the AI model race, a look back at the SnapStream live TV archiving service, AND an update on how much more time we have until all our servers are obsolete.All that and more on a brand new Monday edition of This Week in Startups.

Grok 4 Beats OpenAI + The $300 AI Agent Era | E2150

Today’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 why some companies are raising prices anyway. They also dive into the Missouri AG’s investigation into AI “bias,” the future of First Amendment protections for LLMs, and how autonomous vehicles are creating a new category: “autonomous commerce.” If you’re building with AI or betting on the future of tech, don’t miss this one.

Starlink + Tesla? $4T Nvidia? Perplexity Browser? Linda Yaccarino Steps Down? | E2149

On 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 flights, Linda Yaccarino steps down as X CEO, Waymo launches teen accounts, and maybe recording everything all the time has some disadvantages? Later, Tim Ranzetta joins to explain how his nonprofit is making personal finance mandatory in high schools. A must-watch for founders, investors, and anyone navigating the future of tech.

Startup Valuations, Biotech’s Crunch & AI’s Massive TAM | E2147

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 early-stage investing, with startups raising record-setting rounds adn chasing $100B+ markets. Meanwhile, biotech faces a “Great Depression” as public markets stay shut, putting added pressure on private capital. In healthcare, AI-powered virtual doctors promise to bring world-class medical advice to everyone, while fertility tech could revolutionize IVF by automating embryo handling and slashing costs. Hear our VC experts exclusive thoughts on these trends and much more!

The Grammarly–Superhuman Megadeal, plus TWiST 500 chats with LabelBox and Apptronik’s founders | E2146

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 they’re merging, how they plan to combine apps and AI agents, and what it means for the future of email and work. PLUS they reveal how Grammarly’s 40M+ daily users already rely on email—and why this deal is the key to building the ultimate communication assistant. Don’t miss this deep dive into one of the most exciting AI acquisitions yet!

Travis’ Uber Comeback, AGI’s Stakes, Meta’s $100M AI Hires & Prediction Market Gold Rush | E2144

In this episode of This Week in Startups, Jason Calacanis and Alex Wilhelm delve into the effects of tariff wars on car manufacturers and startups. They explore Travis Kalanick's potential return to Uber and discuss advancements in drone delivery with companies like DoorDash and Zipline. The conversation shifts to industry consolidation in the self-driving and food delivery sectors, followed by an overview of prediction markets with Kalshi and Polymarket. They examine investor roles in prediction markets, OpenAI-Microsoft dynamics, and strategies for startups inspired by major partnerships. The episode concludes with Meta's AI team expansion, talent acquisition, and the challenges of moving from academia to startups.

VC Roundtable: Recruiting Secrets, Second-Time Founders & Product-Market Fit Myths | E2143

In this episode of This Week in Startups, Jason Calacanis hosts Doug Leone and Gili Raanan. They explore recruiting strategies, integrating new team members, and Doug Leone's retirement journey. Gili Raanan discusses Wiz and balancing innovation with practical constraints. The conversation covers managing talent, equity splits, AI's impact on startup efficiency, company building speed, overfunding challenges, and venture capital compensation dynamics. The episode wraps up with insights into early-stage investment strategies and success predictors in venture capital.

The Strip Mining Era of LLMs—And Why It’s About to End | E2141

In this episode of This Week in Startups, Jason chats with Alex Wilhelm and Giram Taitana about AI and business. They discuss AI data sourcing, Meta's financial strategies, and Midjourney's video AI advancements. The conversation covers AI scraping's impact on content creators and the regulation debate. Giram shares insights into medical tourism, focusing on design's role in building trust. They also explore Doctours' fundraising and AI's influence on employment, highlighting new job roles and the gig economy. The episode wraps up with Tesla's robo taxi launch and its potential effects on urban transport.

From Drones to Dystopia: The Future of Jobs, Fires & Meta’s AI Land Grab | E2140

In this episode of This Week in Startups, Jason talks with Alex Wilhelm and Rishab Gupta about key tech and business issues. They discuss Andy Jassy's memo on labor, AI's role in workforce evolution, and challenges in job training for white-collar roles. They also examine the stock market's resilience amid changing media trends and strategic communication approaches. The episode explores future firefighting technology, AI's impact on insurance, and TikTok's implications for US-China relations. Rishab introduces Actuality's AI-driven RFP response platform, emphasizing its human-in-the-loop design and potential impact on the construction industry.

Meta, Scale, and the Future of AI Labeling: Did Zuck Just Kill a Category? | E2139

Meta just took a 49% stake in Scale AI, and the shockwaves are hitting the entire AI ecosystem. In this episode, Jason and Alex unpack the deal’s implications: Google ($150M customer!) and others are fleeing Scale, worried Meta will hoard its RLHF infrastructure and cut off competitors. Startups like Labelbox, Turing, and Handshake are already seeing a demand surge. Is this smart vertical integration or anti-competitive overreach? Jason shares tactical advice for founders on how to capitalize when incumbents stumble—hire ex-Scale talent, build “Scale AI alternative” SEO pages, and hit the podcast circuit. Don’t miss this deep dive into AI’s shifting power dynamics.