OpenAI Scoops Instacart’s CEO, AI in the Courtroom & Off-Road Startups | E2123

Today’s show: Jason, Alex, and Lon break down OpenAI’s latest power move: hiring Instacart CEO Fidji Simo to lead its consumer apps. They also dive into the ethical storm brewing around an AI-generated victim statement used in court — is this the future of legal testimony? Plus, they explore how late-stage funding rounds like a “Series G” don’t automatically spell trouble anymore, and what *The Checklist Manifesto* can teach startup founders. Stick around for another Office Hours, where WhereToWheel gets a shot at the spotlight.

Zoox Crash Fallout, COATUE’s $1B Open Fund, and Office Hours with FusionAds | E2122

Today’s show: Jason, Lon & Alex discuss the day’s hottest tech and startup news. Zoox’s robotaxi crash and voluntary recall, COATUE’s innovative open-ended venture fund that could democratize private tech investing, the NSO Group's massive $167M fine for spyware abuse, Uber’s record-setting earnings and in-person work push, and a candid AI wake-up call from Fiverr’s CEO urging employees to embrace automation or fall behind. From regulatory shakeups to funding innovation and the rise of AI productivity, this episode captures the chaos and opportunity of tech in 2025.

Cursor’s $9B Round, AI-Powered Toys & CloudNuro’s SaaS Fix | E2121

Today’s show: Cursor’s explosive growth, hitting $200M in ARR and a massive $9B valuation. They also explore the buzz around Magical Toys’ new AI-powered dinosaur, where LLMs meet playtime. The conversation turns to “vibe coding” and how AI dev tools are changing the way product teams build. Plus, Jason shares stories from his Formula 1 poker table, Uber’s latest autonomous vehicle partnerships get analyzed, and we bring you highlights from our Founder Fridays pitch showdown, featuring Kippy from Sydney and MomSub from Chicago. Stick around to hear how Cloud Neuro is tackling SaaS sprawl.

Apple’s App Store Loss, AI Persuasion, and an Interview with Tyler Denk of Beehiiv | E2120

Today’s show: Jason, Lon, and Alex break down a loaded week in tech: Apple’s 27% App Store “link-out” fee gets shut down by a judge—unlocking margin for startups and slashing CAC; AI bots on Reddit’s r/ChangeMyView are now 6x more effective than humans at changing minds, signaling a seismic shift in online discourse; and Beehiiv CEO Tyler Denk joins to discuss building in public, rapid product iteration, and the irony of being critiqued like a market leader for innovating too fast. The big takeaway? AI is evolving fast, gatekeepers are falling, and founders who build through chaos are best positioned to win.

What's Next for AI Infrastructure with Amin Vahdat | AI Basics with Google Cloud

In this episode of AI Basics, Jason sits down with Amin Vahdat, VP of ML at Google Cloud, to unpack the mind-blowing infrastructure behind modern AI. They dive into how Google’s TPUs power massive queries, why 2025 is the “Year of Inference,” and how startups can now build what once felt impossible. From real-time agents to exponential speed gains, this is a look inside the AI engine that’s rewriting the future.

Bittensor’s Rise, Meta’s Llama Goes Cloud, & AI Now Writes Your Code | E2119

Today’s show: Jason, Alex, Lon and Special Guest Mark Jeffrey of Hash Rate, cover the explosive rise of Bittensor, a decentralized AI compute network some are calling the “third great coin” after Bitcoin and Ethereum, explore Meta’s bold move to host its open-source LLaMA models via partnerships with Groq and Cerebras—potentially setting the stage for a future AWS competitor—and unpack shocking revelations from the Wall Street Journal about Meta AI chatbots engaging in inappropriate conversations with underage users. Plus, we explore how AI is now writing up to 30% of code at major tech firms like Google and Microsoft, signaling a radical shift in how software gets built.

Meta’s Dangerous Chat, Protect AI & Founder Fridays Pitch Comp | E2118

Today’s show: we break down the wild story behind Meta’s AI chatbots going completely off the rails — including a bombshell WSJ exposé about bots flirting with minors. Then they cover Palo Alto Networks’ huge $500M+ acquisition of Protect AI, and sit down with the founder of Formulate, who’s building a robotic kitchen for chemicals and cosmetics. Plus, we get into some spicy takes on the secret group chats shaping tech behind the scenes, whether AI can clean up bad code faster than humans, and a Founder Fridays Texas showdown between Osprey and Wispr.

Discord’s Power Move, Slate’s Modular EVs & the “Act for Private Gain” | E2117

Today’s show: Jason, Alex, and Lon break down today’s top tech and startup stories — from Slate Auto’s customizable $25K EV truck to Discord’s major leadership shakeup ahead of a potential IPO. They also cover Uber’s self-driving push with Volkswagen, Perplexity AI’s aggressive growth moves, and why value-driven products are winning in a tough economy. Plus, Alex sits down with Tailscale CEO Avery Pennarun to unpack how they grew from 5K to 10K customers — and why fixing internet networking could spark the next huge wave of innovation.

Cursor’s $300M ARR, Uber’s FTC Battle, and Office Hours with GoShare | E2116

Today’s show: Jason, Alex and Lon unpack the FTC’s lawsuit against Uber and what it could mean for subscription UX, break down how AI startup Cursor is growing faster than almost any SaaS company in history, and discuss how dark patterns, consumer trust, and regulatory scrutiny are reshaping product design. They also touch on the future of big tech breakups, share insights from founder Office Hours with GoShare CEO Shaun Savage, highlighting the power of focus, capital, and customer obsession for startups navigating turbulent markets.

Robot Lifeguards, TapCheck’s Payday Play & Thalamus’s Wild Market Share | E2115

Today’s show: Jason and Lon break down the biggest stories in tech and startups this week: OpenAI’s new models are powerful but glitchy, Meta’s internal docs hint that Zuck knows the Facebook friends graph is toast, and fintech startup TapCheck might actually be doing some good. Plus, robot lifeguards and humanoid races — the wildest videos of the week and what they mean. Then, Alex sits down with Jason Reminick, founder of Thalamus, the platform that helps match medical residents to hospitals (with 85% market share!). They talk about becoming a Public Benefit Corp and how Thalamus is tackling the doctor shortage in the U.S.

LMArena Goes Startup, AI App Wars Begin, Scott Bair’s Design Playbook | E2114

In this episode, Jason and guests explore the rapid value accrual in the AI industry, highlighting the business models and benchmarking strategies of AI startups like LM Arena. They discuss milestone-based investing, early-stage funding, and the dynamics of high valuations and consumer AI pricing models. The conversation shifts to the rise of drone startups and the geopolitical implications of autonomous weapon systems. Additionally, the episode features a "Savage my startup" clinic, offering insights on branding, design, and effective website creation. The episode concludes with thoughts on productivity in remote work and the cultural aspects of brand missions.

AI Progress and Impact on Ecosystem Players with CapitalG’s Jill Chase | AI Basics with Google Cloud

In this episode of AI Basics, Jason sits down with CapitalG partner Jill Chase to break down how AI is reshaping the startup ecosystem — from founders to investors to incumbents. They cover how CapitalG (Alphabet’s independent growth fund) thinks about the AI stack, why speed alone isn’t enough for startups today, and how to build durable advantages in a world where anyone can copy your product. Jill shares insights from portfolio companies like Motif (next-gen CAD for architecture) and Abridge (AI-powered doctor’s scribe), plus how startups can use AI “in the business” (product) and “on the business” (ops, GTM, etc). They also explore the transition from copilots to agents — and what that means for the next wave of software. If you’re building or investing in AI, this is a must-watch.

Cuts CEO Talks Tariffs, Figma's IPO Buzz, and a Nerd Crawler Update | E2113

In this episode, we explore the impact of tariffs on ecommerce and CPG with insights from Lon Harris and Alex Wilhelm. We discuss Figma's potential IPO, Adobe's breakup fee, and Hammerspace's $100 million raise. Jason shares his experiences with Patreon and Substack, touches on Trump's legal issues, and Lyft's acquisition of FreeNow. We also dive into OpenAI's new social network and Google's Tmall ads shutdown. Steven Barelli's viral tweet sparks a discussion on tariff-induced costs, supply chain issues, and US manufacturing, ending with critiques of tariff policy communication and domestic job creation.

Vertical AI Innovations: Abacus LLM in Finance & Synthesia's Video Avatars | E2112

Alex interviews founders from Abacus and Synthesia—two companies leading the charge in vertical AI. Abacus is deploying on-prem LLMs to banks and insurers with a focus on data control, accuracy, and integration with legacy infrastructure. Synthesia just hit $100M ARR by helping 70% of the Fortune 100 turn internal documents into scalable AI video. If you're interested in how generative AI is moving from hype to real enterprise utility, this one's for you.

HuggingFace Buys Pollen Robotics, DHH & Bezos Founder Advice & a JCal Origin Story | E2111

Today’s show: In this episode, Jason, Alex, and Lon dive into Blue Origin’s all-female celeb spaceflight (yes, Katy Perry sang on reentry), Hugging Face’s unexpected move into robotics, and Jack Dorsey’s wild take that we should “delete all IP law.” Plus, they break down Figure AI’s eye-popping $39B valuation, the risks of SPVs, and what founders and investors can learn from the SPAC boom. As Jason puts it: “You just have to assume an 80% failure rate.”

Palantir's Fellowship, Coco Robots & Startup Office Hours | E2110

Today’s show: We dive into the latest tech and startup news — including Palantir’s bold new fellowship program that challenges the traditional college path, and DoorDash’s rollout of burrito-delivering Coco robots in LA and Chicago. We debut our new segment “Tips from the Trenches,” focused on how to land your first customers, and wrap up with two great Office Hours: BRX AI (self-healing AI agents) and InviteJet (calendar-based marketing). Plus, one founder’s wild story about a fake investor using an AI deepfake on Zoom. Don’t miss Jason’s tactical GTM advice and a reminder that if no one complains about your pricing, you’re probably too cheap.

70mph Drone Deliveries, 125% Tariffs & What $10M Exits Really Mean | E2109

Jason, Alex, and Lon talk about stories reshaping the startup world: 70mph drone deliveries are officially live in Dallas, with Zipline and Walmart promising groceries “as the crow flies” in under 5 minutes. Meanwhile, Trump slaps a 125% tariff on China and hints at a global economic shakeup — Jason warns founders to brace for layoffs and bankruptcies unless they’ve got a Plan B and C. Finally, a UK startup sells for $450M and VCs barely break even… but the founders walk with $20M. Jason explains how small exits create the most dangerous kind of founder: the one who never needs another check. Plus Office Hours with Orchestra CEO Sergie Poe.

Economic Chaos, More Pitch Madness & the Shopify AI Manifesto | E2108

This episode kicks off with the "cockroach strategy" for startups, focusing on resilience amid market chaos and tariffs. Founders receive advice on navigating economic uncertainty and the tech sector's tariff impacts. The gig economy's downturn resilience and Jason's optimistic outlook are highlighted. Discussions cover SignalFire's billion-dollar fund, substantial startup revenue, Krea’s $87 million raise, subscription model challenges, and AI pricing pressures. AI advancements, Shopify's AI workforce, and Founder Friday updates spotlight Creatant, Kippy, and Vidala Labs. Sunny from Menu Data shares insights on ethical data scraping, pricing, and growth plans.

Rippling Targets $16B, Market Chaos, TikTok Timeout, and Office Hours | E2107

Today’s show: Jason and Alex dive into the startup world’s latest chaos — from Nasdaq’s slide and Trump’s tariffs to Klarna’s IPO pause and Rippling’s $16B target. They break down what founders really need to know: tightening CIO budgets, longer sales cycles, but easier hiring. Plus, TikTok’s ban gets another delay (with Bezos possibly lurking?). In Office Hours, they chat with two sharp founders: Luke Belbina from PodEngine, who's building AI for podcasters and doubling revenue, and David Moscatelli from Abacus, who’s bringing secure, on-prem AI to banks and just hit $1M ARR. Don’t miss it! 👇

Spycraft in SaaS, Rabbit’s Comeback, and Startup Pitch Madness | E2106

In this episode, Jason Calacanis delves into the intriguing corporate espionage case involving Rippling and Deal, exploring its implications and the competitive dynamics in the tech sector, including Y Combinator connections. The conversation examines the legal and potential criminal aspects, while critiquing the spycraft involved. Board governance and Silicon Valley's culture of rule-breaking are also discussed. Later, Jesse Lyu from Rabbit joins to discuss his Y Combinator journey and Rabbit's new hardware product. The episode wraps up with Founder Friday pitch offs, offering critiques and insights into various startup pitches, including an AI-powered podcast app and a community for women in sports.