Robinhood Venture Fund, Polymarket adds earnings, and LAUNCH Accelerator 35 is here! | E2178

Today’s show: There are new LAUNCH Accelerator and Founder U cohorts this week, and Jason’s running down some of his favorite new startups. PLUS Alphabet is the latest member of the $3T club, why Eric Schmidt was SO RIGHT about remote work, Robinhood is opening up private companies to more investors, Polymarket adds earnings reports, how Jason wagered on The Emmys this year, and MORE!

All-In Summit Highlights, Schools Could Block Social Media, FTC Chatbot Investigation, and Zoox hits Vegas | E2177

Today’s show: On Friday’s TWiST, Jason, Alex, and Lon look back at some highlights from this week’s big All-In Summit in Los Angeles, including a fiery, no holds barred presentation from Palantir CEO Alex Karp, Elon Musk delving into the key challenges facing Optimus, and Tucker Carlson debating Mark Cuban on Ukraine. PLUS… why schools may start blocking social media apps, the FTC’s new investigation into social chatbots, AND omnidirectional Zoox robotaxis are headed to Las Vegas.

How Founders Are Building the Next Great Startups | Paid.ai, iTruckr & Tenax AI | E2175

Today’s show: In this TWiST founder triple-shot, Alex digs into the real-world rollout of AI agents: Paid.ai’s Manny Medina explains agent economics and value-based pricing, iTruckr’s Camilo Ramirez shows agents booking loads and coordinating drivers, and Tenax’s Elise Myrans demos computer vision + drones that score a single home’s wildfire/flood risk for smarter underwriting—plus live office-hours on winning enterprise pilots without getting stuck in PoC purgatory.

The Browser Wars heat up! PLUS, Khan on The Bulwark, rules for great domain names, and Polymarket returns | E2174

Today’s show: Jason heard Lina Khan on The Bulwark and got a little fired up. Plus Google doesn’t have to invest in Chrome… or basically do much of anything… Atlassian picked up not just any browser company but THE Browser Company… Follow-up thoughts on that MIT “companies aren’t using AI” study… AND Jason’s “two stock markets” theory. It’s a can’t-miss Friday TWiST.

Creative Structures w/ Becki DeGraw | Wilson Sonsini Startup Legal Basics

Today’s show: Wilson Sonsini Partner Becki DeGraw returns to Startup Legal Basics with Jason. This time, they dive into the *“have” companies* — the breakout startups with multiple term sheets, competitive valuations, and unusual deal terms. From founder voting proxies to mandatory follow-on investment clauses, Becki breaks down the creative “off-menu” structures showing up in today’s financings, and what founders and investors need to watch for. Whether you’re a founder navigating investor FOMO or a VC competing to get on the best cap tables, this conversation will give you insight into the new rules of the game.

Uber, Lucid & Nuro team up on robotaxis by 2026 | E2173

Today’s show: Jason and Alex are joined by Nuro’s Dave Ferguson to unpack the Lucid–Uber–Nuro deal aiming to launch fully driverless Gravity SUVs on Uber by 2026. They dig into why off-the-shelf sensors and Nvidia’s Thor chip drive costs down, how mapping 150 cities improves safety, and why lidar still matters for night and edge cases. Plus: lessons from Cruise’s collapse, how regulators think about safety multiples, and why autonomy could finally make rides cheaper than owning a car.

Jason’s Tesla Optimus prediction, Anthropic’s latest mega-raise and more | E2172

Today’s show: Find out why it’s important to “get curious,” and more deep founder insights on a new TWiST. Jason and Alex are back with a look at Robot vs. Human violence spilling out into the streets, Elon Musk’s vision for humanoid robots, and a reconsideration of Apple’s open-source AI models. Is the hardware giant not getting enough credit for its smaller-scale innovations? Plus Grok has another hit model, AND a chat with Scale Social founder Runbin Dong about the importance of knowing your worth.

KPop Demon Hunters breaks records, Grok speeds up, and an AI-powered browser deep dive | E2171

“KPop Demon Hunters” is one of the year’s biggest smashes… AFTER Sony sold it off to Netflix for cheap! Hear about what went wrong with one of the year’s worst deals… PLUS Grok is counting on SPEED to help it outpace rivals… How Rep. Ritchie Torres (D-NY) ran into trouble on the podcast circuit… Nvidia’s big earnings report, and why everyone is watching that company in particular SO closely… PLUS a new Polymarket predicting the future of OpenAI!

Market Update and Trends w/ Becki DeGraw | Wilson Sonsini Startup Legal Basics

Today's show: Wilson Sonsini Partner Becki DeGraw returns to Startup Legal Basics with Jason to break down what’s happening in today’s startup market. From excess dry powder on the VC side to companies struggling to “grow into” their valuations, Becki shares what founders need to know about deal terms, pay-to-play provisions, and the shift from the 2021 heyday to today’s more structured environment. • Why down rounds and structured deals are becoming more common • How “pay-to-play” works (and why it’s showing up so often now) • The psychology of VCs vs. founders during tough fundraises • What the M&A landscape really looks like in 2025 v Legal provisions investors are using to protect themselves in today’s talent wars Whether you’re a founder preparing for your next round or an investor navigating tougher terms, this conversation will help you understand the new realities of startup fundraising.

Google is Nano Banana, Apple AI plans & The Great H1B Visa Debate | E2170

Today’s show: On a brand-new TWiST, Jason and Alex are asking why there are SO MANY note-taking AI apps? Plus another death has been linked to ChatGPT… is it too easy to get past chatbot guardrails? Why Donald Trump Jr. is joining Polymarket…. How the US Navy could catch up with its international rivals… AND should Apple just buy a big AI company to help them catch up? All that PLUS a visit from Colin Russ, whose viral H1B Visa thread might just inspire Jason to reach out to his good friend, Vice President JD Vance. Check out the full episode!

xAI’s App Store lawsuit, Intel shares vs. grocery stores, and Netskope’s IPO | E2169

Today’s show: On an upbeat and optimistic new TWiST, Jason and Alex are debating why any new innovation or technology gets hit with a wave of bitter cynicism. PLUS Jason defends the government taking shares of Intel, explains the importance of interoperability, and predicts how AirBnB’s Joe Gebbia will upgrade the US government’s website design. All that PLUS thoughts on the Netskope IPO, Perplexity offering publishers actual revenue share, a deep dive on the new AI-based PAC, thoughts on open-source LLMs, and much much much more.

Do Kwon Guilty, Powell Pivot & OpenAI’s $12B Run Rate | E2168

Today’s show: Terra’s collapse, Powell’s pivot, and OpenAI’s explosive growth all collide in this TWiST deep dive. Do Kwon has pled guilty after Terra/Luna’s $60B implosion, Fed Chair Powell hints at a September rate cut, and OpenAI has officially crossed $1B in monthly revenue (on a $12B run rate). Jason and Alex unpack what this means for founders, LPs, and the next wave of AI + crypto. They also cover Canva’s $42B comeback, Anthropic’s doubled $10B fundraise, and the brewing battle between Figma & Canva. Plus: Uber, Nuro & Lucid’s $6B robotaxi push — and why drivers are already protesting in Wuhan & Boston. #Startups #Crypto #AI #VentureCapital #OpenAI #Anthropic #Canva #Figma #ThisWeekInStartups

Is Chalk.ai the ‘Next Databricks’? + Tollbit’s Bot Paywall for AI Agents | E2167

Today’s show: In this TWiST 500 double feature, Alex sits down with two breakout founders: Chalk’s Marc Freed-Finnegan & Tollbit’s Toshit Panigrahi! First, Chalk’s CEO Marc Freed-Finnegan is tackling one of AI’s biggest bottlenecks—data freshness. Instead of relying on stale batch jobs, Chalk delivers real-time pipelines for inference compute, automatically transpiling Python into C++/Rust so it can run blazing fast in production. Investors are calling it the ‘next Databricks’—and after hearing this convo, you’ll see why. Then, Tollbit’s CEO Toshit Panigrahi returns after raising a $24M Series A and signing up 1,400+ publishers. With RAG traffic exploding and robots.txt losing its teeth, their ‘bot paywall’ could reshape how AI agents pay for the content they consume. Are we heading for a Spotify moment for data licensing? A must-watch if you care about the economics of AI, from data pipelines to publisher monetization.

Scaling AI Photo Editing to 300M Users with Photoroom’s Matt Rouif | AI Basics with Google Cloud

In this AI Basics episode, Jason sits down with Matt Rouif, Co-founder & CEO of [Photoroom](https://www.photoroom.com/) — the AI photo editing app with 300M+ downloads and 5B images processed annually. They break down: - Why Photoroom built its own specialized AI models - How they grew from a scrappy startup to $50M+ in revenue - Lessons in product-led growth (from eBay sellers to DoorDash & Amazon) - Red-teaming, brand safety, and building trust in AI imagery - The future of personalized ads, content, and design This one is a masterclass for founders, operators, and builders. * Timestamps: (0:00) Matt Rouif joins Jason to discuss AI Basics. (0:45) Meet Matt Rouif: Photoroom’s $50M+ AI photo startup (3:15) Live demo: background removal + virtual try-on (7:40) From indie sellers to DoorDash & Amazon (12:20) The “Barbie Movie” API moment (17:05) Red-teaming AI: trust, safety & brand protection (22:10) Running a 100-person AI startup (26:30) The future of personalized ads (put *you* in the ad?)

Decart makes AI faster, Lume teaches lamps to fold laundry | E2166

We’re back with two insightful new TWiST founder interviews. First up: Dean Leitersdorf of Decart tells us about squeezing maximum productivity out of your GPUs. But it’s not all talk: he also shows us the incredible open world model that can magically transform live footage. THEN! Jason and Alex chat with Syncere AI founder Aaron Tan about Lume, his robotic lamp device that went viral for folding laundry. Hear why Aaron thinks the future of robotics is not necessarily humanoid, and all about his future plans for the Lume arms.

Meta’s “Sensual” AI Doc LEAKS, Opendoor’s dreams became memes +  OpenAI plans $1T data center spend | E2165

It’s a Friday TWiST and Jason and Alex are FIRED UP about this internal Meta doc laying out appropriate vs. inappropriate AI behavior… You won’t BELIEVE with what Zuck approves for 8-year-old users. PLUS… AI job displacement is HERE, at least in the Big Apple… Jason’s getting kind of paranoid about the surveillance state… AI remains frothier than ever through new Cohere and Cognition rounds… and why we’re dubious that Sam Altman REALLY plans to spend $1 trillion on OpenAI data centers. It’s all happening on a brand-new This Week in Startups. Give it a click!

The End of the ZIRP Era, and why recruiting is SO PAINFUL | E2164

We’re back with another all-star VC roundtable discussion. Joining Jason are Dave McClure of Practical VC, NVNG’s Grady Buchanan, and Tomasz Tunguz of Theory VC. Together, they’re having a deep insider discussion of the state of venture, secondary markets, running funds of funds, the legacy of Lina Khan, the difficulty of recruiting, and why the pendulum has potentially swung in founders’ favor.

GPT Psychosis is spreading, the NYT is Super-Doxxing Zuck, and Trump is wetting his beak on Chinese chip exports | E2163

Today’s show: On an all-new Monday TWiST, Lon joins Jason and Alex to talk about a whole bunch of stories at the intersection of tech, business, and pop culture. First up, is GPT Psychosis real? And if so, what are the warning signs that your loved ones have been ONESHOTTED. Then, why did Jason get so upset at the NY Times piece about Mark Zuckerberg’s Palo Alto compound? PLUS we’re discussing Trump’s export fees on AMD and Nvidia, Jason’s pitch for why the president should work more closely with Congress, a new tool in the search for rare-earth minerals, just how many self-driving trucks are on Chinese roads today, and much much more!

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!