Founders in Arms

Guillermo Rauch, CEO of Vercel, joins Immad Akhund and Raj Suri at a live Founders in Arms event to break down the full arc of building one of the most widely used developer platforms in the world—from a contrarian bet that VCs said was already solved, to a multi-product company powering the future of the web.Guillermo walks through the three chapters of Vercel's growth: finding focus (trimming a portfolio of open source projects down to the one that had undeniable traction), building repeatability (anchoring go-to-market around customer-led ROI stories), and scaling the company itself as the product. Along the way, he shares how he thinks about feedback, why consensus is a red flag for startup ideas, how customer-led innovation beats internal roadmaps, and what "brand permission" has to do with why Google keeps failing at social.The conversation also gets into the current moment in SF—the AI supercycle, the anxiety around who gets left behind, and why Guillermo's answer to all of it is the same: product market fit solves most problems. Just stay focused on building.What you'll learn:Why Guillermo treats everything—including silence—as feedbackThe "pain discovery" method he uses to extract what's actually brokenHow Next.js started as a personal solution and became a wedge into the entire cloudWhy he deliberately ignores competitors when buildingThe three chapters of Vercel's growth and what drove each inflection pointHow customer-led innovation produced some of Vercel's biggest revenue linesWhy your second product has a higher bar than your firstThe iPhone and AirPods framework for thinking about adjacenciesWhat "brand permission" means and why it explains Google's failuresWhy consensus around an idea is a signal to walk awayChapters:00:00 – Managing your own psychology as a founder00:51 – Welcome + live event intro02:55 – Vercel's web stack vs. agent stack04:04 – Guillermo's background and first exit to WordPress05:15 – Spotting the waves: cloud and front end in 201308:49 – Everything is feedback; the pain discovery method10:40 – Short-term pessimism, long-term optimism13:14 – Opinions vs. ideas: the Jony Ive mental model16:40 – Chapter 1: Finding focus — how Next.js became the wedge21:03 – Why consensus is a red flag for startup ideas21:40 – The MacBook moment: simplicity wins25:37 – Chapter 2: Repeatability — e-commerce as the GTM unlock29:30 – Chapter 3: Scaling the company as the product34:41 – iPhone and AirPods: smart adjacencies to a strong core38:41 – Brand permission: why Google keeps failing at social40:18 – The SF culture divide: AI optimists vs. AI anxious43:09 – The AI gentrification of San Francisco49:05 – Being your own coach; founder loneliness and burnout50:46 – What fundraising actually feels like

Karri Saarinen is the co-founder and CEO of Linear, the product and issue tracking platform built for high-performing software teams. A designer by training — with stints at Airbnb and Coinbase — Karri took a different path to founding than most Silicon Valley CEOs. Linear has become one of the most beloved tools in the startup ecosystem, known for its speed, design quality, and now its deep integration with AI agents.What you'll learn:How Linear evolved from issue tracking to a full product-building system with AI agentsWhy speed and quality — not features — were Linear's winning strategy in a crowded marketHow Karri thinks about AI's role in design and why average startup design is getting worseWhy designers rarely become founders and whether AI will change thatThe "Quality Wednesday" ritual Linear uses to keep polish standards high at 120 peopleHow Linear's feature roast process catches blind spots before anything shipsWhat Linear borrowed from Coinbase's hiring playbook — and how work trials outperform interviewsHow Linear built an open agent platform and why it now hosts more agents than any tool in its categoryKarri's take on whether designers should write code — and where design thinking matters mostWhy Linear intentionally pushed PM thinking to engineers and designers instead of hiring traditional PMsIn this episode, we cover: (00:00) Why designers rarely become founders (00:53) Introducing Karri Saarinen and Linear (01:27) How Immad and Karri met 15 years ago (02:00) What Linear actually is — and where it's going (03:13) Mercury running compliance workflows on Linear (05:12) Immad's regret: not investing in Linear early (06:17) How Linear broke through a crowded market (08:08) Speed and quality as a product moat (09:26) Why Mercury and Linear win the same way (14:23) Linear's AI agent strategy and open platform (17:40) Coinbase and Ramp building custom agents on Linear (19:27) Linear's upcoming coding agent and PR review interface (21:31) Karri's background as a designer-CEO (23:33) Why designers don't start more companies (27:15) How AI is blurring the lines between design and engineering (31:03) What AI can't replace in design thinking (34:05) Bleeding roles without losing specialization (36:47) The AI slop problem in product features (37:02) Maintaining quality culture at 120 people (39:31) Quality Wednesdays explained (41:16) The feature roast process (44:18) How Linear collects user feedback (46:33) What Linear borrowed from Coinbase's culture (47:21) Work trials: how they work and why they're better (53:32) Why work trials benefit candidates too

Michael Grinich is the co-founder and CEO of WorkOS, the enterprise authentication and identity infrastructure used by Anthropic, OpenAI, Cursor, xAI, and hundreds of fast-growing companies. Before WorkOS, Michael dropped out of MIT, worked at Dropbox, and founded Nihilus — where a painful first experience with enterprise features planted the seed for everything that came next.In this episode, Immad Akhund and Raj Suri sit down with Michael to talk about the SaaS apocalypse thesis, how WorkOS quietly became the enterprise layer for AI's biggest companies, and what it actually takes to build for developers.What you'll learn:Why the SaaS apocalypse narrative gets it completely backwardsHow WorkOS became the default enterprise-ready layer for AI-native companiesThe Stripe parallel: why developer infrastructure compounds the same way payments didWhat a failed first startup taught Michael about idea validationHow keeping a daily idea notebook — volume, not quality — led to WorkOSWhy second-time founders approach conviction and validation completely differentlyThe do-or-die bond between developer tools and their customersHow Michael taught himself enterprise sales after starting as a purely technical founderWhy building for developers is the ultimate boss battle in techWhat AI getting to Renaissance-printing-press level actually means for softwareChapters:(00:00) The SaaS apocalypse thesis — and why Michael thinks it's wrong(01:09) Introducing Michael Grinich — MIT, Dropbox, and the road to WorkOS(05:14) The Stripe origin story and early MIT startup network(07:03) Drew Houston, Dropbox, and what convinced Michael to build(09:05) Founding Nihilus: three maxed credit cards and two days from missing rent(11:00) How to generate startup ideas: volume over quality, the notebook habit(14:05) Finding sticky ideas — the ones you keep coming back to(17:10) Why the energy behind an idea matters as much as the idea itself(20:16) What experience gives you: pattern recognition and a framework for new scenarios(24:05) The moment Michael saw the enterprise auth problem and knew it was real(27:02) How Anthropic, OpenAI, and Cursor ended up as WorkOS customers(31:16) Why WorkOS sits at the security and growth layer for AI companies(35:06) The ultimate boss battle: building developer tools for other developers(39:06) Why developer customers give the best product feedback — and why that's a gift(44:04) The SaaS apocalypse revisited — and what's actually happening to software(47:17) How AI compressed the timeline to enterprise-ready from months to a day(53:03) Tying company value to something durable through technology waves

In this candid one-on-one episode, Immad and Raj catch up on what's actually happening in tech right now — the AI narratives shifting under everyone's feet, which companies they'd bet on, and how they're thinking about building teams in an AI-native world.What you'll learn:Why Anthropic has taken the AI narrative from OpenAI — and whether that lead will holdImmad's take on whether he'd invest in OpenAI or Anthropic at $800B todayHow Anthropic is growing 3x in revenue in three months — and whether it's even possibleThe new engineering team model: fewer engineers, more autonomy, OKR-driven executionWhy design still matters — and why Mercury embeds designers directly into product teamsHow to time IPO investments: why Raj waits 3-4 months post-listing to buyWhat the SpaceX S-1 signals about the new AI hype cycleWhy Apple is undervalued (or not) — the edge computing argumentHow good Gemini's travel integration actually is (Raj tested it in Tokyo)Why AI real-time translation is still painfully clunky — and what the ideal experience looks likeWhere to find Immad and Raj:[00:00] Data centers in space: skeptical takes [01:02] Anthropic's moment: why the narrative has shifted [02:16] OpenAI vs. Anthropic at $800B: where would you invest? [04:12] Anthropic's 3x revenue growth in 3 months: how is that possible? [06:10] The future of engineering teams in an AI-native world [07:37] Design's role in product: why Mercury still embeds designers everywhere [13:44] SpaceX S-1 and the IPO watch list [14:37] Why post-IPO hype fades and when to actually buy [17:01] Gemini in Tokyo: surprisingly good travel integration [17:43] AI translation fails: what the phoneless experience actually needs [20:06] Apple's AI opportunity and the edge computing bet [22:07] Data centers in space: the only scenario it makes sense [24:19] Xai co-founder exodus and AI researcher retention

George Kailas is the CEO of Prospero AI, a platform helping retail investors make smarter decisions using simplified market signals and data-driven insights.In this episode, George joins Immad and Raj to break down one of the biggest debates in investing today: should you just buy ETFs, or can retail investors actually beat the market?They go deep into how modern markets really work, why retail investors are becoming more powerful than ever, and what most people get wrong about stock picking, AI tools, and “free” trading platforms.What you’ll learn:Why ETFs beat stock picking if you don’t have enough timeHow retail investors now make up a massive share of market movement The biggest mistake investors make: not knowing when to exit Why analyst ratings and price targets often can’t be trusted How platforms like Robinhood actually make money (and what it means for you) The shift from software → data as the real moat in AI Why AI stock-picking tools are dangerous in volatile markets The psychology of investing: why most people need to lose before they learnWhat we cover:00:00 Should You Pick Stocks or Just Buy ETFs? 00:50 Meet George Kailas (Prospero AI) 01:30 Beating the Market with Data Signals 02:15 From Mortgage Models to AI Founder 03:20 Why Data Will Matter More Than Software 04:20 Why People Don’t Trust Analyst Ratings Anymore05:00 Who Is Prospero Actually Built For? 05:45 Value Investing vs Modern Momentum 07:00 The Big Debate: ETFs vs Stock Picking 07:35 The 1-Hour Rule: When You Should NOT Pick Stocks 08:30 Retail Investors Are Driving the Market Now09:30 How to Actually Learn Investing (Without Losing Everything) 10:40 Why Exiting Trades Is the Hardest Skill 11:25 Are Public Markets Really Mispriced?11:55 Why Analyst Price Targets Can’t Be Trusted 13:05 Inside Prospero’s 10 Signals System 14:10 How They Simplify Complex Market Data 15:10 Risk Signals: When to Exit a Trade16:30 How Traders Use Options, Sentiment & Dark Pools 17:30 Are Apps Like Robinhood Good or Bad? 18:10 The Hidden Cost of “Free” Trades 19:30 Why Retail Investors Lose Power Through Brokers20:10 Better Alternatives to Robinhood 21:40 AI, Data, and the Future of Investing 23:00 Why Intent Data Could Change Everything24:40 AI, Layoffs & Wealth Inequality 26:00 The Rise of Crypto Traders & Risk Culture 27:10 Why Some Investors Need to Lose First 29:00 Why AI Tools Are Bad at Risk30:00 Mercury’s Investing Strategy (Simple ETFs) 31:30 Why They Avoid Complexity in Investing Products31:45 Fundraising Journey: From Angels to Crowdfunding 33:00 Lessons from Running a Crowdfund 34:10 When Crowdfunding Actually Works36:00 Mercury’s Acquisition Strategy Explained 38:00 Building an All-in-One Financial Platform41:00 George’s Founder Journey & Early Exit 42:30 From “Sharky” to Self-Aware Leader 43:30 How Meditation Changed His Leadership Style 45:00 Managing Teams: Autonomy, Mastery, Purpose47:00 Long-Term Vision for Prospero AI 49:30 Rapid Fire Begins 49:40 Founder He Admires (Jensen Huang) 50:40 Trends That Won’t Last 51:30 What He Changed His Mind About52:05 Closing Thoughts