Founders in Arms

Immad Akhund and Rajat Suri

In this weekly series, fellow startup founders Immad Akhund (Mercury) and Rajat Suri (Presto, Lima, and Lyft) explore current events in the world of tech, startup, and policy, offering insights from their distinguished careers and an array of expert guests. YouTube: youtube.com/@FoundersInArms Substack: foundersinarms.substack.com Instagram: instagram.com/foundersinarms TikTok: tiktok.com/@foundersinarms_

  1. 3d ago

    Founders in Arms #101: Cursor, OpenRouter, and What's Next in AI

    This week, Immad and Raj sat down for a wide-ranging catch-up on the biggest stories in tech right now — from record-breaking acquisitions to what they're each giving AI access to in their own lives. The conversation kicks off with the OpenRouter-Stripe acquisition and Cursor's $60B deal, and what both say about investing in "obvious" ideas when the underlying trend is right. From there, Immad and Raj get into the economics of secondary markets (including Immad's own purchases of SpaceX and Anthropic shares pre-IPO), why staying private longer might be bad for retail investors, and the case for making it easier for smaller companies to go public. They also dig into consumer AI hardware — why simple, single-purpose devices like Pocket are breaking through where more complicated products haven't — and trade notes on what they've each connected their own AI assistants to, from email and calendars to health results and scheduled tasks. What you'll learn: Why "obvious" ideas can still be some of the best investments, if the trend is rightWhat's driving the OpenRouter-Stripe and Cursor acquisitions, and why they matter for developer toolsHow Immad and Raj think about the risks and opportunities in secondary marketsWhy Immad believes deep secondary liquidity could be bad for retail investors and the broader economyWhat's made simple, single-purpose AI hardware devices succeed where more ambitious ones have struggledHow Immad and Raj are using AI assistants in their own lives, from productivity to personal healthWhy "PMF doesn't exist anymore" in consumer products, according to a recent conversation Raj had with Character AI's CEOWhat it will take for AI to handle more complex, multi-step tasks like buying insuranceHow Anthropic and OpenAI's revenue numbers compare going into the back half of the year Timestamps: (00:47) Introduction (01:21) OpenRouter's acquisition by Stripe (02:18) Cursor's $60B deal and the case for "obvious" ideas (06:03) Why big exits justify high seed valuations (08:47) AI adoption is still low — why Immad is bullish on the next 5-10 years (12:56) Buying into SpaceX and Anthropic pre-IPO (15:17) The case against deep secondary markets (18:21) Why Pocket is winning in consumer AI hardware (20:02) Talking to Matic's robot vacuum (22:07) An idea for family video, and why photo frames haven't solved it (24:14) What Character AI's CEO said about PMF at a recent Tribe event (28:28) What Immad and Raj have given their AI assistants access to (33:08) Scheduled AI tasks, and why AI still can't do the last mile (35:59) Anthropic and OpenAI's latest revenue numbers (38:06) The debate over housing density and California's building laws

  2. Aug 14

    Building Brokerage 2.0: Direct Indexing and Tax Alpha with Mo Al Adham

    Mo Al Adham is the founder and CEO of Frec, a brokerage platform he describes as "brokerage 2.0" — building on core trading primitives to offer more sophisticated strategies like direct indexing, long-short direct indexing, and options overlays. Before Frec, Mo co-founded Twitvid, an early video-for-Twitter startup, and later spent five years at Twitter. He founded Frec in 2021 and launched the product in October 2023. What you'll learn: Why the $1-30M wealth segment — about 10 million US households — controls 40% of all investable wealth in the country, and why it's the fastest-growing segmentHow direct indexing creates "tax alpha" by harvesting capital losses, and why that's a deferral of taxes rather than an elimination of themHow a step-up in cost basis at death effectively forgives the deferred tax billThe concrete numbers: how much a $100k investment can harvest in losses via a classic direct index versus a long-short direct indexWhy long-term, sophisticated investors have proven far less fee-sensitive than the market assumesMo's path from Twitvid — an early video app built on top of Twitter — to five years working inside Twitter itselfHow a frustrating experience with a wealth manager who charged 1% fees for little added value planted the idea for FrecWhy Mo's six months of "top-down" market research largely failed, and why a "bottoms-up" approach — starting from what he actually cared about — led him to FrecWhy Frec had to resequence its roadmap when rising interest rates undercut its original plan to lead with a cheap line-of-credit productImmad's framework for company OKRs (which he calls "COR") and why he insists on including non-measurable resultsWhy Frec has deliberately stayed out of banking, unlike some robo-advisor competitorsMo and Immad's picks for financial products that should already be obsolete Chapters: (00:00) The $1-30M wealth segment and why it holds 40% of US investable wealth (01:03) Introducing Mo Al Adham and Frec, "brokerage 2.0" (02:07) Targeting sophisticated investors vs. democratizing access (03:12) Why long-term investors are stickier and less fee-sensitive than assumed (07:08) Tax alpha explained: deferral vs. elimination (09:20) How direct indexing lowers cost basis through loss harvesting (12:45) Long-short direct index and portfolio tilts (14:16) Mo's first startup, Twitvid, and getting outpaced by Twitter (16:29) The wealth manager experience that inspired Frec (19:49) Vetting the idea: six months of top-down research that failed (22:18) Switching to a bottoms-up approach and finding conviction (30:39) Immad's approach to OKRs, called "COR" (36:24) Frec's pivot from lending to investing as rates rose (52:16) Rapid fire: AI in fintech, obsolete products, and more

  3. Jul 10

    Ethics, Pivots, and the Future of Work: A Live Q&A with Vercel's Guillermo Rauch

    Guillermo Rauch is the co-founder and CEO of Vercel, the company behind Next.js, and previously created the widely-used Socket.io library. In this special episode, recorded live in front of an audience, Guillermo joins Immad Akhund and Raj Suri for an open Q&A covering pivots, ethics, investors, and the future of work in the age of AI. What you'll learn: The difference between a "lowercase p" pivot (refining focus) and an "uppercase P" pivot (starting over) — and how to know which one you needHow to build an ethical framework for operating in an industry full of shortcuts and noiseHow to extract real signal from investors without letting them drive your roadmapReal pivot stories from Presto (restaurant tablets to voice AI), Lyft (carpooling to peer-to-peer ride-hailing), and Mercury's early product-market-fit signalWhy blaming distribution is often easier than blaming the product — and why that's a trapHow founders can get their teams to think about prioritization the way they doHow Mercury created early demand by deliberately recruiting a broad, vocal set of seed investorsWhat "the future of work" looks like when your team's job shifts from producing outcomes directly to building the systems that produce themHow growing up outside Silicon Valley shaped each panelist's belief that they could build something from scratch Chapters: (0:00) Lowercase p vs. uppercase P pivots (1:05) Q&A begins (1:23) Building an ethical framework in Silicon Valley (4:38) Balancing customer signal vs. investor advice (9:53) Pivot stories: Presto, Lyft, and Mercury's obvious PMF moment (15:34) Why founders blame distribution instead of the product (16:08) Getting your team to think about prioritization like you do (18:21) How Mercury created early demand with 60 seed investors (19:48) The future of work: agents, harnesses, and factories of output (24:25) Growing up outside the Valley: mentors and self-belief (28:04) Closing

  4. Jun 26

    The New Rules of Startup Scale: Survival, TAM Illusions, and Opting into Excellence With Dan Teran

    Dan Teran is the co-founder and managing partner of Gutter Capital, an early-stage venture firm investing in vertical AI and marketplace businesses. He previously founded Managed by Q — an operating system for commercial spaces that grew to employ nearly 1,000 people, expanded nationally, and was acquired by WeWork in 2019. Dan joined WeWork as head of corporate development before leaving after a turbulent six months. He now runs Gutter Capital's third fund ($75M) and the Elbow Grease accelerator, sponsored by Mercury, which invests in early-stage founders in New York City. What you'll learn: How Managed by Q found extreme product-market fit in lower Manhattan — and why that made expansion harder, not easierWhy winning a market can be a trap when the TAM is smaller than you thoughtThe real story behind the WeWork acquisition: a three-year relationship, a theatric walkout, and why great exits are always principal-to-principalWhy over-capitalization was more ruinous to Managed by Q than any external factorHow to think about Series A benchmarks for non-AI companies today (2–3M ARR, renewals, one productive AE, 3x growth)Why AI-enabled services businesses can be great companies even if they're not venture-scale outcomesThe mismatch between what early-stage founders need to raise and what top VC funds are mandated to deployWhy founders should play the hype game — but stay ruthlessly honest with themselves about what game they're playingDan's take on Adam Neumann: what made him exceptional, where he fell short, and why Dan wouldn't bet against himThe "leaders eat last" philosophy — and why holding people to high standards and having their backs aren't in conflict Chapters: [00:00] The hype trap founders fall into [01:31] Managed by Q: founding story and early growth [02:39] Scaling nationally and selling to WeWork [04:17] The state of co-working and commercial real estate post-WeWork [07:18] In-person vs. remote — what actually matters pre-PMF [11:16] How the WeWork acquisition really happened [15:06] Realizing the TAM was smaller than expected [17:09] Raj's parallel experience at Presto [20:04] FOMO-driven investing and the AI diligence problem [22:04] Series A benchmarks for applied AI companies today [25:27] Why founders should aim for break-even before raising [28:56] The mismatch between venture fund mandates and founder needs [34:32] What Dan learned about fundraising after becoming an investor [37:30] Adam Neumann, WeWork, and Flow [39:30] Leadership, high standards, and the "leaders eat last" philosophy [42:12] Why founders learn the wrong lessons from Steve Jobs [47:31] FarmEvo: the drone ag company Dan flew to Karachi to diligence

  5. Jun 5

    Before Robots Were Cool: The 33-Year Journey of iRobot's Founder, Colin Angle

    Colin Angle spent 33 years building iRobot — bootstrapping for eight years without venture capital, surviving 15 failed business models, and ultimately launching Roomba in year 12. What followed was a decade of overcoming consumer skepticism, 70%+ global market share, a public offering on Nasdaq, and eventually a blocked acquisition by Amazon. Now he's back with a new company, Familiar Machines and Magic, building robots designed for human connection — priced to compete with the cost of owning a pet. What you'll learn: Why Colin believes iRobot would have failed with early VC accessHow iRobot funded itself for eight years through customer contracts instead of investorsThe sales tactic Colin used to get Fortune 500 CTOs to fund iRobot's R&DHow DoD mine-hunting algorithms and a Hasbro partnership became the technology inside RoombaThe wallet share framework for evaluating whether a consumer robot idea can actually workWhy adding features to a consumer robot often reduces perceived valueHow iRobot priced Roomba at $199 with a $42 BOM — and what that discipline requiredWhat it felt like to go public, and how everything changes when what you say can be monetizedThe full story behind the Amazon acquisition attempt and why the EU and FTC blocked itWhat Familiar Machines and Magic is building and why the pet economy is the target comp Chapters: 00:00 – Regulators celebrate blocked deals — what Colin saw on FTC examiners' doors 00:53 – Introducing Colin Angle, co-founder of iRobot and Familiar Machines and Magic 02:00 – The "if not us, who?" moment that started iRobot 03:54 – First business model: privately fund a moon mission, sell the movie rights 07:03 – Eight years without VC: "completely unfundable" 08:09 – The CTO sales tactic: present a problem half a step from their real one 09:00 – "Work for no profit, cancel anytime" — the deal structure they used five times 12:05 – Built for 10,000 units, sold 70,000 Roombas in three months 15:03 – "If I had VC early, iRobot would have failed" 18:40 – $199 retail, $42 BOM — the Roomba economics 20:31 – The wallet share framework: which consumer spend are you actually replacing? 32:39 – First interview as a public CEO: "My wife says Roomba doesn't work" 34:42 – The Amazon acquisition gets blocked — 15% market share and falling 42:09 – Familiar Machines and Magic: the new company and the original vision 46:12 – Building robots for human connection, not task automation

  6. May 29

    Guillermo Rauch at Founders in Arms Live: Simplicity, Focus, and the Bet That Built Vercel

    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 away Chapters: 00:00 – Managing your own psychology as a founder 00:51 – Welcome + live event intro 02:55 – Vercel's web stack vs. agent stack 04:04 – Guillermo's background and first exit to WordPress 05:15 – Spotting the waves: cloud and front end in 2013 08:49 – Everything is feedback; the pain discovery method 10:40 – Short-term pessimism, long-term optimism 13:14 – Opinions vs. ideas: the Jony Ive mental model 16:40 – Chapter 1: Finding focus — how Next.js became the wedge 21:03 – Why consensus is a red flag for startup ideas 21:40 – The MacBook moment: simplicity wins 25:37 – Chapter 2: Repeatability — e-commerce as the GTM unlock 29:30 – Chapter 3: Scaling the company as the product 34:41 – iPhone and AirPods: smart adjacencies to a strong core 38:41 – Brand permission: why Google keeps failing at social 40:18 – The SF culture divide: AI optimists vs. AI anxious 43:09 – The AI gentrification of San Francisco 49:05 – Being your own coach; founder loneliness and burnout 50:46 – What fundraising actually feels like

  7. May 22

    Building for Quality in a World of AI Slop with Linear's Karri Saarinen

    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 PMs In 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

  8. May 1

    WorkOS's Michael Grinich on Becoming the Enterprise Layer for AI's Biggest Companies

    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 software Chapters: (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

See All (111)

Ratings & Reviews

5
out of 5
2 Ratings

About

In this weekly series, fellow startup founders Immad Akhund (Mercury) and Rajat Suri (Presto, Lima, and Lyft) explore current events in the world of tech, startup, and policy, offering insights from their distinguished careers and an array of expert guests. YouTube: youtube.com/@FoundersInArms Substack: foundersinarms.substack.com Instagram: instagram.com/foundersinarms TikTok: tiktok.com/@foundersinarms_

Information

  • Creator
    Immad Akhund and Rajat Suri
  • Years Active
    2023 - 2026
  • Episodes
    111
  • Rating
    Explicit
  • Copyright
    © Copyright 2026 Immad Akhund and Rajat Suri
  • Show Website
    Founders in Arms

You Might Also Like