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  • Jonathan Ross on Groq’s $20 Billion NVIDIA Deal, Faster Inference, and Why Asking the Right Questions Wins the AI Age

    Jonathan Ross, the founder of Groq and the inventor of Google’s Tensor Processing Unit (TPU), sits down with David Senra (host of the Founders podcast) to walk through Groq’s roughly $20 billion partnership with NVIDIA and the decade of near-death struggle that preceded it. You can watch the full conversation here. Ross, now a senior executive at NVIDIA following the deal, is unusually candid about being one of the world’s worst leaders when he started, about coming three weeks from running out of money, and about the single contrarian bet (that faster inference would make AI both faster and smarter) that almost everyone, including his own engineers, told him was pointless.

    TLDW

    Ross explains the structure of the NVIDIA deal (a call to Jensen Huang about buying 100,000 GPUs turned, in three weeks, into NVIDIA’s largest deal by nearly 3x) and why pairing Groq’s LPU with the GPU defeats the many different bottlenecks inside an LLM the way you would use both 18-wheelers and delivery vans in a logistics network. He unpacks the AlphaGo moment that revealed faster inference makes models smarter, the shift from the information age (answering questions) to the AI age (asking the right questions), and a leadership philosophy built on autonomy, one brutally clear priority (25 million tokens per second on a challenge coin), and giving people the fewest constraints so they can surprise you. He shares hard-won lessons from Jensen and NVIDIA (the least political large org he has seen, no secret one-on-ones), his concepts of reality quotient and the dominant game, return on luck and the GitHub opportunity he let his team talk him out of, intentional leadership (“I intend to do this”), the Grok bonds that traded salary for equity and saved the company, hiring for negatives instead of positives, loss bias and manufactured discontent, and a closing case for radical optimism: code is becoming free, software creation is being democratized like literacy, and education should stop teaching kids to answer questions and start teaching them to ask.

    Thoughts

    The technical spine of this interview is a genuinely counterintuitive claim: you can make a model smarter by making it faster. Ross’s proof is the AlphaGo anecdote, where the exact same model, ported from GPUs to his TPU, saw its ELO jump by hundreds of points and beat the world champion, because more compute per unit of time let it search deeper and surface moves like the famous Move 37 that were too far down the tree to find otherwise. Once you internalize that inference speed is not a convenience but a capability multiplier, the entire Groq thesis, and the logic of the NVIDIA deal, snaps into focus. The industry spent years treating fast inference as a nice-to-have. Ross treated it as the whole game, and was nearly alone in doing so for a very long time.

    The most transferable material is the leadership arc, precisely because Ross is willing to say he was bad at it. His core insight is that there is no single correct way to lead, any more than there is one way to invest, and the founder’s first job is to know which way is true to them. Ross is a delegator who hires autonomous people and gives them a single, poetically compressed objective, then gets out of the way. The reason that matters is subtle: if you over-constrain the goal, your team can never surprise you with a better answer than the one you already had, which means they can never actually innovate. The Kelly Johnson line Senra offers (“extreme performance often comes from one brutally clear priority”) is the same idea from the Skunk Works side. A challenge coin that reads “25 million tokens per second” is not a slogan, it is a mechanism that lets every engineer connect their work to one dominant game.

    Two ideas deserve to be lifted out and used directly. The first is intentional leadership, borrowed from David Marquet’s submarine turnaround: replace “should I do this?” with “I intend to do this.” Asking for opinions invites pessimism and hands your most timid people a veto. Declaring intent still lets someone shout “the hatch is open” when it truly matters, but it stops the reflexive no. Ross traces years of stalled progress to the simple error of asking instead of declaring. The second is his inversion of hiring: hire for negatives, not positives. Growing talent means showing people the path, so you emphasize positives. Selecting talent means screening people out, so you hunt for the disqualifying negatives, because one person’s negative trait infects the whole team. Most founders, Ross included for years, are clever enough to talk themselves into any candidate. A versioned “people spec” and a deliberate loss-averse posture are the antidote.

    The Grok bonds story is the emotional center and a small masterpiece of change management. Facing a layoff list that would have killed the company (because the people slated to be cut were exactly the ones needed to make the product work at all), Ross instead asked the team to trade salary for equity, framed with World War II war-bond imagery. Eighty percent participated, half went to statutory minimum wage, and attrition actually fell. His phrase for why is “put everyone’s hands on the steering wheel.” Passengers fear a windy road, drivers feel in control. It is a reminder that morale under existential stress is often a function of agency, not comfort, and that the Phil Knight move of converting employee sacrifice into ownership is a recurring pattern in company survival stories for a reason.

    Where the conversation turns almost spiritual is manufactured discontent. Ross observes that the entrepreneurs in a room of successful people were the least happy with their wealth, and that this very dissatisfaction was the fuel that kept them building. His own current discontent is stark and worth sitting with: the world does not have enough compute, and if it takes an extra year to cure cancer or slow aging because of that shortage, he considers it his fault. Whether or not you accept the moral weight he assigns himself, the mechanism is instructive. Edwin Land wrote “300 people died today” on the whiteboard while inventing anti-glare technology. A concrete, human cost attached to delay is a far more durable motivator than a revenue target. Paired with his closing optimism about code becoming free and software creation democratizing like literacy, it makes for one of the more clear-eyed and yet hopeful founder conversations in recent memory.

    Key Takeaways

    • The NVIDIA deal began as a request to buy about 100,000 GPUs; Jensen saw what Groq had built pairing GPUs and LPUs and decided to make it available to all NVIDIA customers, closing what Ross calls the firm’s biggest deal by nearly 3x in roughly three weeks from first call to wired money.
    • GPUs and LPUs are complementary: inside an LLM’s decoder layer, the GPU is better at the compute-bound attention portion and the LPU is better at the memory-throughput-bound weights, so combining them defeats bottlenecks across the whole performance curve, like using both 18-wheelers and last-mile vans.
    • As AI increasingly talks to AI, speed dominates, because agents kick off other agents and compound; a human tolerates a one-second wait, but AI is just sitting there idle.
    • Agentic micro payments will make the number of payments skyrocket, but payments infrastructure is not yet built for AI operating inside an allocated budget.
    • Ross prototypes cutting-edge ideas as personal hobby projects first, then brings them to work; his personalized “daily brief” evolved from long text into headlines he can interrogate with follow-up questions, like the game of 20 questions.
    • The information age rewarded answering questions; the AI age rewards asking the right ones, as everyone shifts from individual contributor to leader of AI, and good leaders ask the question no one else did.
    • There is no single right way to lead, just as there are many ways to invest; the founder’s job is to know themselves and pick the leadership form that is true to them (inspiration versus fear, control versus delegation).
    • Ross was, by his own account, one of the world’s worst leaders at the start, which cost Groq three to four years; his fix was to define one goal simple enough to fit on a challenge coin: 25 million tokens per second.
    • The fewer constraints you give a person (or an AI agent), the more freedom they have to surprise you with a better solution; over-constraining the goal makes real innovation impossible.
    • Lessons from Jensen and NVIDIA: it is the least political large organization Ross has seen, Jensen never runs secret one-on-ones (tell everyone at once, copy everyone on email), and the whole strategy reduces to “what does the customer actually need?”
    • Jensen manages around 60 direct reports, each smarter than him in their own domain, which he offers as the model for orchestrating AI agents that may be smarter than you.
    • Asking a sharp question that makes an expert say “I didn’t think of that” is a universal founder skill (it appears in every Bezos book) and can be honed.
    • Confidence, not competence, was Ross’s early bottleneck: shadowing a leader of 2,000 people, he realized he would have made the same decisions, and acting with confidence made people follow his direction without changing the decisions themselves.
    • The better and more creative your people, the harder they are to manage; running 450 highly creative scientists felt more like managing 5,000.
    • Reality quotient (RQ), distinct from IQ, is the ability to recognize reality and, in its extreme form, to choose the dominant game; MySpace optimized accounts signed up while Facebook optimized monthly active users and won.
    • The first principle of change management is to make it feel like it is not a change; people who seem fine with change are usually anchored to something that did not change.
    • Return on luck (from Jim Collins): the most successful companies do not get more lucky breaks, they seize the ones they get; Ross let his team talk him out of powering GitHub’s LLMs on Groq chips, then vowed never again.
    • People adopt fast inference only when they experience it personally; an Anthropic demo three months before ChatGPT drew no reaction because the answers were not the audience’s own, and Groq later went viral off a fast-LLM video posted on X.
    • Great innovators often experience a problem before others do; the future is already here, just not evenly distributed, and Ross saw fast inference’s value first because of AlphaGo.
    • Intentional leadership (from David Marquet’s USS Santa Fe turnaround): say “I intend to do this” instead of asking for an opinion, which stops reflexive pessimism while still letting people flag a real problem.
    • Grok bonds: three weeks from running out of money, Ross swapped a layoff for a war-bond-style salary-for-equity exchange; 80% participated, about half took statutory minimum wage, and it bought roughly two months of runway.
    • “Put everyone’s hands on the steering wheel”: participation in saving the company cut attrition to under 10% during the crisis, echoing Phil Knight converting employee loans into Nike equity.
    • West Coast VCs behave like lemmings (one pass triggers all passes), while East Coast VCs run independent analysis; the herd missed what became NVIDIA’s biggest deal ever, a live example of the Keynesian beauty contest.
    • For the first time, top startups are not starved for cash, so putting in more money is no longer an advantage even though investors still behave as if it is.
    • Hiring flip: move from hiring for positives (how you grow talent) to hiring for negatives (how you select talent), because one negative trait poisons the team; write a versioned “people spec” like a product spec.
    • Loss bias (a loss feels roughly six times more painful than an equal gain) can be a hiring signal: Ross looks for people who “book the win early,” treating any missed improvement as a loss.
    • Poetic design (maximum meaning in minimal expression, “every word matters”) was a positive on the people spec; its negative is maximalist, cluttered design.
    • Michael Jordan manufactured pressure by taunting opponents so a loss would be humiliating, forcing superhuman performance (per his trainer Tim Grover), a deliberate version of throwing your keys over the fence.
    • Manufactured discontent (David Ogilvy’s “divine discontent”): the best entrepreneurs never rest on wins; the least happy people with their wealth were the ones who kept building.
    • Ross’s discontent today is the world’s lack of compute; he treats every delayed medical breakthrough as partly his responsibility, the way Edwin Land wrote a daily death count on the whiteboard while fighting headlight glare.
    • Software has run on “code rationing” because code was expensive to write, enforced by “no engineers”; as the marginal cost of code approaches zero, you just implement, experience, and re-implement.
    • AI democratizes software creation like the alphabet democratized literacy: Ross’s executive assistant now builds working apps, and individual founders with taste but no coding background will create valuable companies.
    • Education should be revamped around asking questions and solving real community problems; if a kid can look up or prompt the answer, the assignment taught nothing, but making them ask the right questions to get AI to solve a real problem does.

    Detailed Summary

    The $20 Billion NVIDIA Deal and Why LPUs and GPUs Belong Together

    The deal’s most striking feature is speed: the idea was first floated on a call roughly three weeks before the money was in the bank. Groq had been integrating GPUs and LPUs and went to Jensen Huang wanting to buy about 100,000 GPUs to deploy themselves. Jensen saw the combined system and decided it should be offered to all of NVIDIA’s customers. The technical logic is that processing an LLM token involves many matrix multiplies with different bottlenecks, some compute-constrained (better on the GPU, especially the attention portion) and some memory-throughput-constrained (better on the LPU, applying the trained weights). There is no single perfect architecture, so putting the two together defeats bottlenecks across the whole curve. Ross adds that as AI talks to AI, speed becomes everything, because agents spawn agents and compound exponentially.

    Asking Questions, Daily Briefs, and the Shift to Leading AI

    Ross builds cutting-edge tools as personal hobby projects before bringing them to work, including a personalized “daily brief” that functions like a presidential daily brief. He redesigned it from long text into headlines he can interrogate, because interactivity, like 20 questions, distills straight to what you actually care about. This grounds one of his signature ideas: success in the information age meant answering questions, but success in the AI age means asking the right questions. As people move from individual contributors to leaders of AI, the skill that matters is the leader’s skill of asking the question everyone else missed or was afraid to raise, since the question you ask determines the output you get.

    Knowing Your Leadership Style and the Challenge Coin

    Ross frames leadership like investing: the first principle is simply having followers, but there are infinite valid styles. New founders fail by copying advice that is not true to them. Ross is a natural delegator (he has not held a driver’s license since his teens because he would rather think than control the car) who hires unusually autonomous people. Early on this backfired badly, because he entrusted people who needed direction, and he calls himself one of the world’s worst early leaders, a gap that cost Groq years. His breakthrough was distilling the mission onto a challenge coin reading “25 million tokens per second,” which let everyone connect their work to one dominant game. He references David Marquet’s Turn the Ship Around later, but the coin embodies Kelly Johnson’s Skunk Works principle that extreme performance comes from one brutally clear priority, plus the rule that fewer constraints give people more room to surprise you, turning a team from Superman into the Avengers.

    Lessons from Jensen: Killing Politics and Serving the Customer

    Working at NVIDIA taught Ross how much further he could have pushed lessons he half-learned at Groq. NVIDIA is, in his experience, the least political large organization anywhere, and a big reason is that Jensen never tells different people different things in private one-on-ones. When you address a room, everyone hears the same message; separate conversations breed side cliques. Ross’s practical rules: hold big meetings for anything you want a group to know, and copy everyone on email so no one can route politics through you. The other Jensen lesson is to stop playing 3D chess and just ask what the customer needs, tell them only what you believe and can support, and refuse to sell them something they do not need. Senra notes he has covered roughly 19 ideas from The Nvidia Way on his Founders podcast, and Jensen’s line that he already manages 60 reports smarter than him is the template for managing AI agents.

    Reality Quotient, the Dominant Game, and Change Management

    Groq hired for reality quotient, not just IQ, because plenty of very smart people construct elaborate stories disconnected from reality. In its extreme form, RQ is the ability to choose the dominant game, the way Facebook’s focus on monthly active users beat MySpace’s focus on accounts signed up. The founder’s job is to help everyone connect their activity to that dominant game (for Groq, tokens per second), then manage the change. Ross’s first principle of change management is to make it feel like it is not a change: nobody likes change, and people who tolerate it well are usually focused on something that stayed constant. If your team is anchored to the dominant goal, a new tactic does not feel like change; if they are anchored to a narrow task, it does.

    Return on Luck, the AlphaGo Insight, and the GitHub Miss

    From Jim Collins’s Great by Choice, Ross took the idea that winners seize luck better, not that they get more of it. He experienced it first-hand with AlphaGo: after a DeepMind team asked whether his TPU was as fast as rumored (he said yes, Ghostbusters-style), porting the identical model from GPUs to TPUs pushed its ELO from around 3,200 to roughly 3,900 and it crushed the world champion. As Thinking Fast and Slow by Daniel Kahneman frames it, more compute lets the model virtually play out more moves and occasionally find a better second-best line, which is how the famous Move 37 surfaced. Faster thinking is smarter thinking. Yet Ross also let his own engineers talk him out of powering GitHub’s LLMs on Groq chips, twice, because they focused on why it could not be done rather than why it could. He eventually did the math himself, hit the numbers, and learned to stop inviting that pessimism.

    Selling Speed and Intentional Leadership

    Customers could not grasp fast inference until they felt it. Ross recalls an Anthropic demo three months before ChatGPT that drew no reaction, because seeing someone else’s answer appear is not magical, but getting your own question answered instantly is. So Groq simply put fast inference online, and it went viral after someone posted a video of a blazing-fast LLM on X (Ross noticed his own demo slowing in Norway because usage had skyrocketed). The deeper fix for internal resistance came from Turn the Ship Around, David Marquet’s account of turning the USS Santa Fe from worst to best in nuclear readiness by replacing command-and-control with intentional leadership. Saying “I intend to do this” rather than “should I?” stops people from reflexively supplying negative opinions, while still letting someone shout “the hatch is open” when there is a genuine problem.

    Grok Bonds: Three Weeks From Zero

    With three weeks of cash left and a layoff list on the table, Ross realized the cuts targeted exactly the people needed to finish an unprecedented compiler and reach the critical mass where the product would even work. Layoffs would not save the company; only reducing burn without losing people could. So Groq held an all-hands, put up World War II war-bond imagery, and launched “Grok bonds,” an exchange of salary for equity. Ross expected heavy attrition; instead 80% participated and about half dropped to statutory minimum wage, real pain for engineers used to six-figure salaries. It bought closer to two months of runway. His framing, “put everyone’s hands on the steering wheel,” explains why attrition actually fell below 10%: drivers feel more in control than passengers, and it echoes Phil Knight in Shoe Dog converting employee loans into Nike equity on the edge of collapse.

    Hiring for Negatives, Loss Bias, and Manufactured Discontent

    Ross was good at spotting smart, talented people but kept hiring ones who caused organizational problems, because he could always talk himself into a candidate. Watching a sharp head of HR screen people out, he realized he had been hiring wrong: growing talent means showing positives, but selecting talent means hunting for disqualifying negatives, since one bad trait spreads to the whole team. He formalized a versioned “people spec” with positives like return on luck and poetic design, each paired with a negative. He also hired for loss bias, the fact that a loss feels roughly six times more painful than an equal gain, seeking people who “book the win early.” That competitive, pressure-seeking wiring links to Michael Jordan manufacturing humiliation stakes (per Tim Grover in Relentless) and to David Ogilvy’s divine discontent. Ross’s own manufactured discontent today is the world’s shortage of compute, which he frames in life-and-death terms.

    The Optimistic Close: Free Code and Universal Software Literacy

    Ross ends on aggressive optimism. Software has long run on “code rationing” because code was expensive to write, policed by “no engineers” whose job is to say no. As the marginal cost of code approaches zero, the workflow flips to implement, experience, then re-implement. More important is accessibility: just as alphabets and universal education turned reading and writing from a scribe’s monopoly into a question of quality, AI is making software creation universal. His executive assistant now builds working apps, and a wave of individual founders with taste but no coding background will create valuable companies. The corollary for education is to stop teaching kids to answer questions and start teaching them to ask, revamping curricula around real community problems where the point is asking the right questions to get AI to solve something that matters.

    Notable Quotes

    “Success in the information age was about being able to answer questions. Success in the AI age will be about being able to ask the right questions.”

    Jonathan Ross, on the fundamental shift AI creates

    “The fewer constraints that you give someone, the more freedom they have to solve the problem, and the more freedom they have to surprise you with the solution.”

    Jonathan Ross, on leading creative teams

    “Being able to think faster makes you think smarter.”

    Jonathan Ross, on why faster inference produces more capable models

    “There are plenty of really smart people who wouldn’t recognize reality if it tapped them on the shoulder.”

    Jonathan Ross, defining reality quotient versus IQ

    “If you express intentional leadership, you say, ‘I intend to do this.’ People don’t tend to offer their opinion, but if it’s very wrong and there’s a reason, they will push back.”

    Jonathan Ross, on the lesson from Turn the Ship Around

    “When people are passengers in a car, they’re more nervous about a windy road or a scary road. But when they’re the driver, they feel more in control.”

    Jonathan Ross, on why Grok bonds kept the team together

    “The biggest flip in my hiring was when I went from looking for positives, which is what you do when you’re trying to grow talent, to looking for negatives, which is what you do when you’re trying to select talent.”

    Jonathan Ross, on inverting his approach to hiring

    “If it takes us an extra year to cure cancer because we don’t have enough compute, that’s my fault.”

    Jonathan Ross, on the discontent that drives him today

    Watch the full conversation between Jonathan Ross and David Senra here on YouTube.

    Related Reading

    • Groq the company Ross founded and the LPU behind the fast-inference story and the NVIDIA partnership.
    • AlphaGo versus Lee Sedol (Wikipedia) the match, including Move 37, that showed Ross how much faster hardware raises a model’s capability.
    • The Keynesian Beauty Contest (Wikipedia) the dynamic Ross uses to explain why West Coast VCs herded past what became NVIDIA’s biggest deal.
    • Zero to One by Peter Thiel, the source of the first-principles thinking Ross applied to the contrarian bet on fast inference.
    • Founders podcast by David Senra the host’s biography-driven show, source of the Jensen, Michael Jordan, and Edwin Land ideas referenced throughout.

  • Brian Chesky on AI Founder Mode, the 11-Star Experience, and Reinventing Airbnb for the Age of AI

    Airbnb CEO Brian Chesky sits down with Patrick O’Shaughnessy on Invest Like The Best to talk about the next evolution of company building: AI Founder Mode. He covers the shift from founder to CEO, the lessons he learned from Steve Jobs through Hiroki Asai, why consumer AI is the next great frontier, and how he plans to change the atomic unit of Airbnb from a home to a person.

    TLDW

    Brian Chesky believes the next era of company building belongs to founders who refuse to delegate the soul of their company. He coined Founder Mode with Paul Graham after the pandemic forced him to take Airbnb back into his own hands. Now he is shaping what comes next: AI Founder Mode, where leaders work with on-demand context, fewer layers of management, asynchronous communication, and a new generation of hybrid manager-makers. He shares why most software companies have not been touched by AI yet, why consumer AI is about to explode, and why he is rebuilding Airbnb around people, not homes. The conversation also touches on the 11-Star Experience exercise, the power of small teams, why recruiting is the most important job a CEO has, and why every adult is still an artist underneath.

    Key Takeaways

    • Founder Mode is not micromanagement, it is having a steering wheel. Chesky woke up in 2019 feeling like the car had no steering wheel. After the pandemic, he reviewed every detail for two to three years before delegating again. Start hands-on and give ground grudgingly, not the other way around.
    • AI Founder Mode is even more intense. With AI, leaders can be in significantly more details because almost everything is on demand. Expect fewer layers of management, mostly asynchronous work, and the death of the pure people manager.
    • Two types of leaders will not survive AI. Pure people managers who only do one-on-ones, and rigid people who refuse to evolve. Everyone needs to be a hybrid manager-IC who can still touch the work.
    • Manage people through the work, not through meetings. Frank Lloyd Wright did it. Johnny Ive does it. You are not anyone’s therapist.
    • Consumer AI is the next great prize. 159 of the last 175 Y Combinator companies were enterprise. Almost every app on your home screen has not changed since AI arrived. That changes in the next 12 to 24 months.
    • Why consumer AI is hard. No proven business model, mature distribution, trend-chasing investor culture, and the simple fact that consumer is more hits-driven and requires excellence in design, marketing, culture, and press, not just technology and sales.
    • Project Hawaii is the new operating model. A 10 to 12 person Navy SEAL team, hands-on coaching from the CEO, crawl-walk-run-fly. The first project added roughly $200 million in year one and $400 to $500 million in year two.
    • Make the problem as small as possible. Airbnb spent 16 years failing to launch a second hit because it kept trying to scale globally on day one. Now: pilot in one city, expand to 10, then industrialize.
    • It is better to have 100 people love you than a million people sort of like you. Paul Buchheit shipped Gmail only after 100 Googlers loved it. The sample size of intense love is enough to predict mass adoption.
    • The 11-Star Experience is an imagination exercise. Push to absurdity (Elon takes you to space) so a 6 or 7-star experience suddenly seems normal. The gap between 5 and 6 stars is the gap between you and your competitor.
    • Simplicity is distillation, not subtraction. Hiroki Asai, Steve Jobs’s longtime creative director, taught Chesky that great design distills something to its essence. First principles is a design term too.
    • The score takes care of itself. Bill Walsh and John Wooden both taught that you do not focus on winning, you focus on making every input perfect. Wooden spent his first hour with new players teaching them how to put on socks.
    • Industrial design is the original product management. There are no PMs in industrial design. The designer is the PM, working alongside engineers and program managers to design through user journeys.
    • Recruiting is the CEO’s number one job. The more time you spend recruiting, the less time you spend managing, because great people self-manage. Build pipelines, not searches. Start with results, work backwards to people.
    • Co-hire the top 200 people, not just the executive team. Most CEOs hire executives and let them hire their teams. Chesky considers that fatal because most executives cannot hire well without help.
    • Bodybuilding is a metaphor for leadership. If you can change your body, you can change your life. Progressive overload, 1 percent a day, is how compounding works. Start with biology before therapy.
    • Founder-led companies build the deepest moats. Disney is still selling Walt’s playbook 60 years after he died. Apple is still selling Steve’s iPhone. The longer founders stay in founder mode, the more the company can endure when they leave.
    • Software is hyper fast fashion. Hardware ages well. Buildings get patina. Software always looks dated 10 years later. What endures is the community, the brand, the principles, the mission, and the network effect.
    • Apps are dying. Agents are coming. Chesky says we should let go of our attachment to apps because they are not what the future looks like.
    • Airbnb’s atomic unit is changing from a home to a person. Chesky wants to build the most authenticated identity on the internet, the richest preference library, a real-world social graph, and a membership program. Then expand to 50 to 70 verticals on top of that identity.
    • AI shifts attention from consumption to creation. Social media gave you a paintbrush only for opinions. AI gives everyone a real paintbrush and canvas. We are heading into a creative renaissance.
    • Founders are expeditionaries, not visionaries. They put one foot in front of the other and call it a vision later.
    • Detach from accolades. Chesky describes adulation as a cup with a hole in the bottom. Status is a drug. The path to durable creative work is doing it because you love it, the way Walt Disney, Da Vinci, Van Gogh, and Steve Jobs did until the very end.
    • The kindest gift is belief. The best way to activate a person’s potential is to see something in them they do not yet see in themselves.

    Detailed Summary

    From Industrial Design to the CEO Chair

    Chesky studied industrial design at the Rhode Island School of Design. He chose it on instinct after a department head told him industrial designers design everything from a toothbrush to a spaceship. He grew up enchanted by the Reebok Pump, the Game Boy, the Nintendo, and eventually by the late 1990s golden age of Apple. Raymond Loewy, the man who designed Air Force One and an enormous catalog of mid-century consumer products, became a touchstone, but Johnny Ive was the real hero.

    What he loved about industrial design was that it is technical, commercial, and empathetic. A building can win an architecture award and never be leased. A piece of industrial design that does not sell is a failure. So you have to think about manufacturing, distribution, marketing, and most importantly, user journeys. There are no product managers in industrial design. The designer is the PM. That training, he says, prepared him directly for the role of CEO.

    The Pandemic and the Birth of Founder Mode

    Chesky says no one is born a good CEO. People are born good founders. The job of CEO is counterintuitive in almost every direction. Founders are taught to learn by doing, but a CEO who learns by trial and error wastes years unwinding the empires of misfit hires.

    By 2019 he was running a 7,000 person company he no longer recognized. He felt he was driving a car without a steering wheel. He had a dream that he had left Airbnb for ten years and come back to find it had become a giant political bureaucracy. Then he realized he had been there the whole time. The pandemic hit and Airbnb lost 80 percent of its business in eight weeks. He shifted from peacetime to wartime, took control of every detail, worked 100-hour weeks, and reviewed everything for two to three years.

    The vision was never to micromanage forever. The vision was: I need to know what is going on before I can empower anyone. Hire people, audit their work, and only then give ground grudgingly. Most founders do the opposite, which is why they end up with executives building empires they later have to dismantle.

    AI Founder Mode

    Chesky says AI Founder Mode will be even more intense than Founder Mode because nearly everything will be on demand. He used to live in 35 hours of meetings a week to gather information, the same way Steve Jobs ran Apple. He held weekly, biweekly, monthly, and quarterly group reviews with the full chain of command in one room, anyone could speak, and he made the final call after listening last.

    In the AI era, that culture shifts from meetings to asynchronous work. He expects fewer layers of management. He cites the Catholic Church as a 2,000-year-old institution with only four layers and asks why most companies need seven, eight, or nine. Pure people managers will not survive. Every manager will have to be a hybrid IC, an engineer who still codes, a lawyer who still reads case law, a designer who still designs. You manage through the work, not through one-on-ones.

    He is also bullish that AI tooling will become consumer-grade simple very soon. The current tools, including Claude Code and Cowork, are not yet intuitive to the average person, but the economic incentive will force that to change.

    Why Consumer AI Is the Next Great Frontier

    Chesky points out that 159 of the last 175 Y Combinator companies were enterprise. Almost every consumer app on your phone, including Airbnb, has not fundamentally changed since the arrival of AI. He gives four reasons: investors feared ChatGPT would kill consumer companies; consumer AI has no proven business model because subscriptions hit a local max against free Claude and Gemini, ads are off the table for most labs, and e-commerce has been shut down via third-party app removals; distribution is mature; and Silicon Valley culture, while branded as rebellious, is in practice trend-following.

    The deeper reason is simply that consumer is harder. It is hits-driven, requires great design, marketing, culture, press, and you cannot easily start by selling to your dorm-mates the way enterprise YC startups sell to other YC startups. The prize is bigger. The risk is bigger. He predicts a consumer AI renaissance over the next 12 to 24 months.

    Project Hawaii and the Magic of Small Teams

    Inside Airbnb, Chesky tested a new operating model called Project Hawaii. He took 10 to 12 people, designers, engineers, product, and data scientists, treated them like a startup inside the company, and pointed them at one problem: improving the guest funnel. The system is crawl, walk, run, fly. First fix bugs, then add features, then re-imagine flows, then completely reinvent.

    The first team delivered roughly $200 million of internal revenue in year one and $400 to $500 million the next year, eventually contributing more than 600 basis points of conversion improvement on a base of $134 billion in gross sales. Then they took the same system to pricing, then to other problems, then to launching new businesses like Services and Experiences.

    The guiding lesson: make the problem as small as possible. Airbnb launched in one city, New York. Uber in San Francisco. DoorDash in Palo Alto. When Chesky launched Services and Experiences in 100 cities at once last year, it did not work. The fix was to dominate one city, expand to 10, then industrialize. Peter Thiel said it cleanly: better to have a monopoly of a tiny market than a small share of a big market.

    Underneath that is a Paul Buchheit insight Chesky calls the best advice he ever got. It is better to have 100 people love you than a million people sort of like you. Buchheit refused to ship Gmail until 100 Googlers loved it, and that took two years. Once 100 people loved it, 100 million people did.

    The Hiroki Asai Lessons: Simplicity and Craft

    Hiroki Asai, Steve Jobs’s quietly legendary creative director, taught Chesky two principles. The first is that simplicity is not removing things, simplicity is distillation, understanding something so deeply that you can express its essence. Steve Jobs called design the fundamental soul of a man-made creation that reveals itself through subsequent layers. Elon Musk’s first principles thinking is the same idea applied to physics.

    The second is craft. How you do anything is how you do everything. Chesky cites Bill Walsh’s The Score Takes Care of Itself and John Wooden’s first hour with UCLA players, an hour spent teaching them how to put on their socks. Walsh said the way you tucked your jersey was one of 10,000 details that decided whether you won. The lesson is to focus on getting every input right. The output follows.

    The 11-Star Experience

    The 11-Star Experience is one of Chesky’s most copied frameworks. Most Airbnb stays get five stars because anything else means something went wrong. So Chesky asked: what would six stars look like? Your favorite wine on the table, fruit, snacks, a handwritten card. Seven stars? A limousine at the airport and the surfboard waiting for you because they know you surf. Eight stars? An elephant and a parade in your honor. Nine stars, the Beatles arrive in 1964 with 5,000 screaming fans. Ten stars, Elon Musk takes you to space.

    The point is the absurdity. By imagining the impossible, six and seven star experiences stop seeming crazy. The gap between five and six stars is the gap between you and your competitor. If you can industrialize a sixth star, you may have product-market fit. The exercise also restarts your imagination, which Patrick noted has atrophied for many people in the era of consumption-only social media.

    AI as a Canvas for Creativity

    Chesky frames AI as the ultimate platform shift, the ultimate creative expression, and possibly the greatest invention in human history. Social media made us mostly consumers and gave creators only opinion-shaped tools. AI gives everyone a paintbrush. He believes far more people are creative than we recognize because most have never had craftsmanship or tools to express what is in their heads. Pablo Picasso said all children are born artists; the problem is to remain one as you grow up. Chesky thinks every adult is still an artist underneath.

    The Next Chapter of Airbnb

    Chesky describes four phases of the CEO journey: get to product-market fit, scale to hyper-growth, become a real profitable public company, and finally reinvent. Airbnb’s stock has been flat because the core idea is saturating. He is now squarely in phase four, with three priorities.

    First, change the atomic unit from a home to a person. He wants Airbnb to build the most authenticated identity on the internet, the richest preference library, a real-world social graph, and a membership program. Proof of personhood, he says, will be enormously valuable in the AI age. Second, industrialize the new-business engine to support 50 to 70 verticals (homes, experiences, services, eventually flights, and more) all built on top of that personal atomic unit. Third, navigate the AI transition without breaking the existing business or the livelihoods of hosts. He is also exploring sandbox apps that imagine a radically different Airbnb, the answer to “what is after Airbnb?”

    What Endures in the Age of AI

    Chesky is direct that software does not endure. Look at any software from 10 years ago and it looks dated. Hardware ages better. Buildings develop patina. Paris endures. So if you want to build something lasting, you cannot bet on the app. You have to bet on the community, the brand, the mission, the principles, the identity, and the network effect. Apps are going away, replaced by agents. Founders attached to apps need to let go.

    Founder-Led Moats: Disney and the Ham Sandwich Paradox

    Chesky reconciles Warren Buffett’s “buy a company a ham sandwich could run” with the venture capital truth that a founder’s ceiling is the company’s ceiling. The reconciliation is Disney. Most people cannot name a Paramount, Warner Brothers, Universal, or MGM film off the top of their head, but everyone can name Disney films. Walt Disney was a founder in founder mode for so long that he created enough IP and momentum that the company has been running on his playbook for 60 years after his death. Apple is similar with Steve Jobs and the iPhone.

    The counterintuitive lesson: if you want a company to last 100 years, do not delegate early to make it independent of you. Stay in founder mode for as long as possible so you can institutionalize the magic deeply enough that it endures after you. Tech is the industry of change, so founder mode matters even more there than in chocolate or insurance.

    Bodybuilding as Leadership Training

    Chesky was a 135-pound late bloomer who told his friends he would compete at the national level in bodybuilding by 19. He did. Two lessons came out of it. First, if you can change your body, you can change your life. Start with biology before therapy. Second, you cannot get in shape in one day. Progressive overload, discipline, consistency, and roughly 1 percent a day compound into massive gains. The visible feedback loop in bodybuilding taught him to break invisible problems (like the quality of a leadership team) into observable, measurable proxies (like the quality of the room at a twice-yearly roadmap review of the top 100 people).

    Recruiting as the CEO’s Number One Job

    Sam Altman told a 27-year-old Chesky he would spend 50 percent of his time on hiring. Chesky did not, and considers that his biggest mistake. He now starts and ends every day with his recruiter and spends two to three hours a day on hiring. The more time you spend recruiting, the less time you have to spend managing because great people self-manage.

    His system is pipeline recruiting, not search recruiting. He never starts with a search firm. He constantly meets the best people in their fields, asks each one to introduce him to the next two or three best, and builds a rolling rolodex. He starts with results, finds an ad he loves, and works backwards to the team that made it. He builds little mafias of top talent inside the company. He is the co-hiring manager for the top 200 people at Airbnb, not just executives, because most executives cannot hire well without help.

    Activating Talent and the Power of Belief

    You cannot teach motivation. You can only give people a problem and see if they have agency. The way to activate someone, Chesky says, is to show them potential they cannot yet see in themselves. He cites John Wooden, who said the secret to coaching was that he saw potential in players they did not see in themselves. People will climb mountains for that.

    The kindest gift anyone gave Chesky, he says, was belief. A high school art teacher named Miss Williams told his parents he was going to be a famous artist. He never became one, but the belief gave him the confidence to choose art school and to choose to be happy. Michael Seibel and the Justin.tv founders believed in him. Paul Graham made an exception to fund a non-engineer with what he thought was a bad idea. His co-founders Joe and Nate believed in him when he had no business being a CEO. The biggest gift you can give back, he says, is belief in others.

    Detaching from the Scoreboard

    Chesky describes adulation as a cup with a hole in the bottom. Status keeps draining out and you keep needing more to feel the same. The day Airbnb went public at a $100 billion valuation should have been one of the best days of his life. The next morning he put on sweatpants for a Zoom meeting and felt nothing. That triggered a re-evaluation. He stopped seeking accolades and started focusing on intrinsic work. He cites Rick Rubin: an artist is an artist when they make for themselves. He cites Vice President Obama, who told him to focus on what you want to do, not who you want to be.

    His four heroes are Leonardo da Vinci, Vincent Van Gogh, Walt Disney, and Steve Jobs. All four were working until the last week or day of their lives. Da Vinci carried the Mona Lisa with him until he died. Van Gogh sold one painting in his life. Disney was imagining theme parks in the ceiling tiles of his hospital room. Chesky says his motivation is the motivation of an artist. He calls being a CEO of a public company at his scale “almost a glitch in the system” that gave him one of the largest design canvases in human history.

    Thoughts

    What stands out about this conversation is how clearly Chesky has decoupled identity from outcome. He frames himself first as a designer, second as a CEO, and considers the resources he commands as a kind of accidental fortune for an industrial designer to be sitting on. That self-image is what lets him talk about disrupting Airbnb, killing the app paradigm, and changing the atomic unit of the company without flinching. Most public-company CEOs cannot afford that posture.

    The framework worth stealing is Project Hawaii. The pattern of taking a 10-person elite team, putting them under direct CEO coaching, and running them through crawl-walk-run-fly is a near-universal answer to the problem of innovation inside a large company. It works because it removes abstraction layers, creates direct contact with reality, and gives the founder a way to teach muscle memory before delegating. Anyone running a team of any size can borrow the pattern: pick one problem, staff it small, work with it weekly, then let go gradually. The golf-instructor analogy of teaching muscle memory before bad habits set in might be the most important management metaphor of the year.

    His prediction about consumer AI is the most economically interesting part of the talk. The fact that 159 of 175 recent YC companies are enterprise is a startling concentration. If he is right that the next 12 to 24 months bring a consumer renaissance, the opening is enormous. The hard part is what he names directly: there is no proven business model for consumer AI yet. Subscriptions cap out against free incumbents, ads are off-limits for the labs, and e-commerce has been throttled. Solving the business model is probably more valuable than building the next great consumer interface.

    The deeper philosophical thread, that AI is the transition from consumption to creation, is one that anyone building tools for makers should hold close. The 11-Star Experience also reads differently in the AI era. It used to be a thought exercise constrained by what you could plausibly build. AI compresses the gap between imagination and execution to minutes, sometimes seconds. The question is no longer “what is the most absurd version of this experience?” but “which six and seven star experiences can I now industrialize that were unthinkable a year ago?” The exercise has become operational.

    Finally, the meta-lesson on founder-led moats is worth taking seriously. The instinct in venture capital and at most public-company boards is to professionalize early. Chesky’s argument is the opposite: the longer the founder stays in founder mode, the deeper the IP and the longer the company endures after they leave. Disney is the proof. Apple is the proof. Whether Airbnb will be is the open question, and it is the question Chesky is using AI Founder Mode to answer.