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Tag: Founder Mode

  • Paul Graham and Jessica Livingston on Resilience at Y Combinator: Founder Mode, Cockroaches, Sticking to Your North Star, and Why AI and Climate Keep Them Up at Night

    For the very first episode of Disaster Proof, the conversation goes to a garage in Palo Alto to sit down with Paul Graham and Jessica Livingston, the founders of Y Combinator. They have backed thousands of companies, including many now working in the resilience space, and the discussion covers what makes startups durable, why adaptability beats expertise, how Brian Chesky stumbled into founder mode at Airbnb, why the best ideas grow out of a founder’s own life, and the two specific risks (AI and climate change) that Paul says are the only ones he treats as genuinely game over. You can watch the full conversation on YouTube here.

    TLDW

    Paul Graham and Jessica Livingston explain why constant change favors young, flexible founders, and why Y Combinator picks people over ideas precisely so its judgment never goes obsolete. They unpack adaptability as the trait they hunt for in interviews, the “founder mode” story behind Brian Chesky steering Airbnb through COVID, and the 2008 strategy of funding tough, close-to-revenue “cockroaches.” Paul argues a company survives turbulence by sticking to a North Star instead of acting as a weather vane in shifting moral fashions, using the biosphere tree that collapses without wind as his metaphor for resilience. They turn to climate and energy as the next great market, the difficulty of selling into utilities, the Gridware success story, fusion no longer being thirty years away, and the trap of guilt-based business models versus the reliable assumption that users are selfish, greedy, and lazy. The personal-resilience half covers surviving Twitter mobs, Paul’s obsessive essay process, raising kids by indulging curiosity and picking your battles, prepping by living among reasonable people, political polarization, and why AI and climate are the two things that keep them up at night.

    Thoughts

    The most useful idea in this conversation is also the most counterintuitive: a world that feels like it is ending is structurally good for the people least invested in how it used to work. Paul’s point to terrified founders is that change is only a threat if you have sunk costs in the old order. A young founder has been doing the current plan for two weeks, so a step-function shift in the landscape costs them almost nothing to abandon. The incumbents with elaborate machinery and a decade of assumptions are the ones who should be afraid. That reframes resilience away from defense and toward optionality. The resilient party is not the one with the thickest walls, it is the one with the least to unlearn.

    The founder mode discussion is worth sitting with because it quietly overturns a generation of management orthodoxy. The old rule was that a good CEO hires executives and gets out of their way, and that getting into the details is micromanaging. Brian Chesky’s COVID experience at Airbnb broke that rule under maximum pressure. With bankruptcy on the table and a travel company facing a world that stopped traveling, he went line by line through the business and told people what good looked like, then gave them freedom to execute against that standard while still demanding visibility. The interesting nuance is the permission structure. A crisis granted Chesky the license to be involved that normal operating conditions would have framed as meddling. The lesson is not “always be in the weeds,” it is that the founder’s deep understanding and disproportionate caring are assets you are wasting if you reflexively delegate them away.

    Paul’s North Star argument is the part most likely to age well. His claim is that companies fail at resilience when they behave like weather vanes, swinging with each gust of public moral fashion. He pairs it with the biosphere tree that grows weak and topples because it was never exposed to wind. Both metaphors point at the same thing: resilience is built by surviving stress while holding your shape, not by avoiding stress and not by reshaping yourself to whatever the crowd currently rewards. The carbon-credit companies he mentions are the cautionary case. They built their entire premise on a fashion (customer guilt about carbon) and went out of business when the wind changed direction. Durable businesses convert a permanent human motive into value, which is why he prefers the brutally honest assumption that the user is selfish, greedy, and lazy, and that your job is to build something that produces good outcomes anyway.

    The climate and energy section reframes a worthy cause as a market-timing bet rather than a moral appeal, and that is the more powerful version. The comparison to fintech in 2008 is the tell. Banking technology was a sleepy, unglamorous sector that venture investors avoided until a crisis cracked it open and made it one of the best categories of the following decade. The argument is that energy and the physical world are sitting at a similar precipice, made newly viable because hardware is starting to behave more like software (order components, assemble, do not build everything from scratch) and because AI’s hunger for power has made energy the binding constraint on the whole industry. The Gridware story crystallizes the founder lesson underneath all of it. The best founder for a hard physical problem was a lineman who worked the electric lines and lived through the fires. The idea grew authentically out of his life, which is the same pattern Jessica keeps returning to and the same advice they give for raising kids.

    Finally, the personal-resilience material is more practical than it first appears. Paul’s method for surviving a Twitter mob is pattern recognition: once it has happened twenty times, you know it ends in two days and they move on to the next target, so you wait it out instead of capitulating. His essay process is the same conviction-building engine applied to ideas. He goes sentence by sentence until there is no false statement left to attack, which is why his challenge to angry readers (“point out the incorrect statement”) almost never gets answered. The throughline across the company advice, the parenting advice, and the personal advice is identical. You build durable conviction not by sitting in a room thinking, but by working the problem until it is right, then refusing to be blown off course by people who never actually engaged with the substance.

    Key Takeaways

    • Experts are frequently wrong because they are experts in a previous version of the world, so Paul deliberately avoids permanent beliefs about the current state of technology.
    • Y Combinator picks startups by picking founders, not ideas, because the founders know more about the ideas than the investors do.
    • Living in England and visiting for each batch lets Paul arrive every quarter expecting the world to be different, which keeps his mind open instead of anchored.
    • A world of constant change feels bad but is actually good for a young, flexible founder who has only been on the current plan for two weeks and can switch easily.
    • Vibe coding went from kind-of-works to reliably works, and even experienced programmers now generate huge volumes of code with AI.
    • There is still a software business even with AI, because someone has to know what to tell the AI to write, and no company is going to write its own database from scratch.
    • The scenario Paul worries about is model companies spinning up agents to start all the startups themselves, removing the need for human founders.
    • The founder traits Jessica looks for are unchanged over the years: determined, flexible-minded, and willing to adapt.
    • In interviews you can spot rigid founders because they answer the question they prepared rather than the one they were asked, and the gears visibly grind when you redirect them.
    • A good adaptability signal is a founder who says “I haven’t thought about that, but here is how I would think about it” instead of freezing.
    • Founder mode, the term, came from Brian Chesky’s experience steering Airbnb through COVID, when bankruptcy was openly discussed in board meetings.
    • Ken Chenault, the former American Express CEO on Airbnb’s board, told Chesky the moment was ten times worse than 9/11 and could define the company.
    • Founder mode meant Chesky understood every line item, told people what good looked like, then gave them freedom to execute while still wanting to see it.
    • Founders see through the fog because they understand the company better than anyone and they care more than anyone, and combining understanding with caring lets them see more.
    • There is always some disaster at Y Combinator, the way a hospital always has someone coding, so a crisis is the normal operating environment, not an exception.
    • During the 2008 crash, YC kept funding because it is always a good time to start a startup, but focused on people close to making money and very tough founders they called cockroaches.
    • Airbnb was the ultimate cockroach, seemingly indestructible, which is exactly why they liked it during the meltdown.
    • YC rests on two axioms: startups matter, and founders are the most important ingredient in startups. As long as those hold, YC has room to exist.
    • Company values are usually written down a few years in, documenting principles that already existed rather than inventing new ones.
    • You cannot move with fashion; you have to stick to your North Star, especially during turbulent, noisy times.
    • Trees grown inside a biosphere fell over because they were never exposed to wind, so being blown around is a necessary part of becoming strong enough to stand.
    • What preserves YC most is that it is a fundamentally good idea: it gives lonely founders money, the right peers, and colleagues they would never otherwise have.
    • The measure of a good startup idea is revenue, and any other metric you care about matters only because it predicts revenue.
    • At the early stage you can afford to be virtuous and even tell founders to go back to college, because the power law means one startup in the batch will carry the returns.
    • Every startup has to find early adopters, who decide quickly, usually do not have much money, and tend to be sophisticated, which means utilities are rarely your first customer.
    • A company that ultimately sells to utilities should start by selling to something that says yes faster, like running a pilot on a single corporate campus.
    • Utilities are under so much stress from wildfire liability, renewables, EV charging, and AI demand that they are unusually willing to try new things out of necessity.
    • Gridware, founded by a former lineman who lived through major fires, is now backed by Sequoia with PG&E as a huge customer, an example of an idea growing out of the founder’s life.
    • The second-biggest chunk of YC startups after AI is hard tech and physical products, not because software is dead but because building physical things is getting more possible.
    • Energy is one of AI’s fundamental constraints; if Sam Altman could have two things for Christmas, they would be energy and GPUs.
    • Nobody says fusion is thirty years away anymore, and the old thirty-year number existed because it was far enough out to avoid demands for results but close enough to keep attention.
    • Energy and physical markets may be where fintech was in 2008, a sleepy sector about to be cracked open by crisis into a great decade.
    • Guilt is a fragile business model because fashions change what people feel guilty about, which is why carbon-credit companies collapsed when the winds shifted.
    • Assume the user is selfish, greedy, and lazy, then build something that causes good things to happen anyway, like clean power that is simply cheaper and more reliable.
    • To survive Twitter mobs, remember they move on in about two days, half are bots or people you would never talk to in real life, and you cannot become a weather vane for moral fashions.
    • You build conviction by working on and developing an idea, not by sitting in a room thinking, unless it is pure thought like math.
    • Paul writes essays sentence by sentence until nothing in them is false, which is why his challenge to point out an incorrect statement almost never gets answered.
    • The best startup ideas, and the best projects in life generally, grow authentically out of the founder’s own interests and experiences.
    • Their parenting philosophy is to give kids confidence and a stable base, indulge their curiosity, and encourage projects nobody told them to do.
    • You pick your battles with kids: put your foot down on cruelty, but accept defeat on things like food and screen time.
    • A useful interview question for anyone with an unusual experience is not “what was it like” but “how was it different than you expected,” which surfaces the genuinely novel detail.
    • In a time of turbulence, bet on an island full of reasonable people; the English may not be very dynamic, but they are reasonable.
    • The hope on political polarization is to build resilient institutions that act as a cage around any single leader, so that throwing the rattle makes no difference.
    • AI and climate change are the two things Paul worries about most because they are both potentially game over, like the Gulf Stream reversing and turning Europe into a frozen wasteland.

    Detailed Summary

    Staying an expert when the world keeps changing

    The conversation opens on Paul Graham’s essay “How to Be an Expert in a Changing World,” whose core point is that experts are often wrong because they are experts in a previous version of the world. Asked how he keeps his own beliefs from going obsolete when the landscape can shift in ninety days, Paul says he focuses on people. YC picks founders rather than ideas because the founders know the ideas better than any investor could. He deliberately holds no permanent beliefs about the current state of technology, and the rhythm of flying in from England for each batch helps: he arrives every quarter already expecting everything to be different. One quarter the story is everyone training open-source models, the next quarter it is Claude code and nobody bothers with open-source models because the frontier versions are better anyway. He comes in with a completely open mind. Jessica and Paul note that today’s founders are more frightened, asking what is even still true, but the message Paul gives them is that constant change favors the young and flexible. If you have only been executing a plan for two weeks, a disruption costs you nothing; you just switch.

    What adaptability looks like in a founder

    Jessica describes the founders she funds as determined, flexible-minded, and willing to adapt, and calls adaptability a key trait always, but especially in uncertain times. In interviews, the rigid applicants reveal themselves by answering the question they planned to answer rather than the one they were asked, and you can almost hear the gears grind when you redirect them. Paul does not let that slide; if they dodge, he just asks again. The positive signal is a founder who, faced with a question they have not considered, says “here is how I would think about it” and reasons live. Both point out that YC itself had to adapt, and that the company they funded the interviewer’s startup as in 2009 looked very different by the end. They funded him in May 2009, in the thick of the financial crisis, after he had quit his job in August 2008 and briefly felt he had made a terrible mistake.

    Founder mode and seeing through the fog

    Paul points to Brian Chesky as the defining example of weathering disaster, a story he explored on This Week in Startups. When COVID hit a travel company like Airbnb, the word bankruptcy was being used in board meetings, and Ken Chenault, the former American Express CEO on the board, warned it was ten times worse than 9/11. Chesky went into what would later be named founder mode, getting into every line item, understanding exactly what was needed, telling people what good looked like, and then giving them freedom to execute while still insisting on visibility. The crisis gave him permission to be the involved CEO he had always wanted to be, the kind of involvement that normal operating conditions would have labeled micromanaging. Paul argues founders see through fog that blinds everyone else for a simple, rational reason: they understand the company better than anyone because they have been there longest and thought of most of it, and they also care more than anyone. Combine deep understanding with deep caring and of course they see more.

    Cockroaches, the North Star, and the biosphere tree

    Returning to 2008, when YC was self-funded and unsure whether anyone would invest by March, they decided to keep going on the principle that it is always a good time to start a startup, but to fund people close to making money and very tough founders they called cockroaches, after the creatures that survive nuclear war. Airbnb was the ultimate cockroach. Paul frames YC’s longevity around two axioms (startups matter, founders are the most important ingredient) and around resilience built through stress. He tells the story of trees grown inside a biosphere that fell over because they were never exposed to wind, since being blown about is a necessary part of a tree becoming strong enough to support its own weight. YC has been blown around and is still standing, which is exactly what gave it practice. The companion idea is the North Star: you cannot move with fashion or act as a weather vane swinging with other people’s moral fashions, you have to hold your founding principles, which Paul eventually wrote down rather than let a 23-year-old new hire do it.

    Climate, energy, and selling into hard markets

    The interviewer’s own path (a curiosity about wildfire that grew from living in California, watching PG&E go bankrupt, a fire on his Mendocino property, volunteering as a firefighter) becomes the case for ideas that grow authentically out of a founder’s life. Climate is framed broadly as energy, the built environment, and transportation, essentially the physical world, and those are hard markets where the buyers are utilities, governments, real estate, and insurance. The advice is to find early adopters who decide quickly, which usually means not starting with a utility but with something like a single corporate campus that will say yes faster. Utilities, though, are under so much stress from wildfire liability, renewables, EV charging, and AI demand that they are increasingly willing to try new things. Gridware, founded by a former lineman who lived through major fires, is the proof point: backed by Sequoia, with PG&E as a major customer. Paul notes the second-biggest chunk of YC startups after AI is hard tech, not because software died but because building physical things is getting more possible, more like ordering and assembling components. Energy is the binding constraint on AI, fusion no longer feels thirty years away, and the bet is that energy and physical markets are where fintech was in 2008, about to be cracked open.

    Guilt versus greed as a business model

    On the question of whether climate companies should sell on guilt (recycle, pay more because it is sustainable), Paul is blunt that guilt is fragile because fashions change what you are supposed to feel guilty about. The carbon-credit companies thrived until buying carbon credits stopped being cool, then went out of business. A founder’s own concern for the world can drive great companies, but depending on a customer’s guilt is shallow. The durable move is to assume the user is selfish, greedy, and lazy, someone who just wants to eat pizza and watch Netflix, and to build something that produces good outcomes despite that. Clean power is the perfect example: nobody watching Netflix is upset that fusion powers their television, and if it is cheaper and more reliable, that is simply more Netflix and more money for pizza.

    Personal resilience, Twitter mobs, and the essay process

    On surviving public criticism, Paul’s method is pattern recognition: after twenty mobs you stop counting and know it will be over in two days when they move to the next topic, so you wait it out even though it genuinely feels miserable. Half of them are bots or people you would never talk to in real life, but the deeper point is that companies and people stay resilient by not succumbing to mobs and not becoming weather vanes for moral fashions. Conviction is built by working on an idea, not sitting in a room thinking about it, unless it is pure thought like math. His essays are the engine: he writes a version one, notices everything wrong, and fixes it sentence by sentence until there is no false statement left. He will read an entire book for a single sentence because he would be mortified to publish something false and, having no deadlines, has no excuse. That is why his standing challenge to angry readers, to point out one incorrect statement, almost never gets answered.

    Raising kids, prepping, and the things that keep them up at night

    Their parenting philosophy is to give kids confidence and a stable base, indulge curiosity, and encourage projects nobody assigned, like the living room overrun by one son’s Lego. They pick their battles: they put their foot down on cruelty but admit total defeat on food, devices, and screen time. Paul’s favorite question for anyone with an unusual experience is not “what was it like” but “how was it different than you expected,” which surfaces the genuinely novel detail, and the meta-version of that became the show’s recurring question to all guests. On prepping, they joke that living in the English countryside is itself a form of preparation, and that in turbulent times you should bet on an island full of reasonable people. The episode closes on what keeps them up at night: AI and climate change, the two things Paul treats as uniquely game over, illustrated by the prospect of the Gulf Stream reversing and leaving Europe, which sits as far north as Alaska, a frozen wasteland. Jessica notes her YC superhero name was Panic, and the conversation ends, after a detour through political polarization and a child who insisted for six months on being called SR-71 forecast 80 leaping leopard, on the admission that they manage screen time by being utterly defeated.

    Notable Quotes

    “If you’re a startup founder, a world where things are constantly changing is actually good for you. It feels bad, but you’re better off than anybody else.”

    Paul Graham, on why turbulence favors young, flexible founders

    “You can’t move with fashion. You have to stick to your North Star.”

    Paul Graham, on holding founding principles during noisy, turbulent times

    “There’s always some kind of disaster. It’s almost a rule of thumb at Y Combinator that there’s always some disaster going on, just like in a hospital. There’s always somebody who’s coding.”

    Paul Graham, on crisis as the normal operating environment for startups

    “The measure of a good startup idea is revenue, sure. Let’s not pretend companies are supposed to do something else.”

    Paul Graham, on how to judge whether an idea is actually good

    “Assume that the user is selfish and lazy, and make something. Selfish, greedy, and lazy. And make something that causes good things to happen despite that.”

    Paul Graham, on why guilt is a weak business model and greed is a source of energy

    “This is where the best startup ideas come from. They grow authentically out of the founders’ lives.”

    Jessica Livingston, on a wildfire curiosity turning into a company

    “Please point out the incorrect statement I’ve made in this essay. And no one ever does that.”

    Paul Graham, on writing essays sentence by sentence until nothing in them is false

    “AI and climate change have something in common. They’re the two big things I worry about the most, because they’re both game overs.”

    Paul Graham, on what keeps him up at night

    This is the first episode of Disaster Proof, a series exploring the people and technologies building resilience in an increasingly volatile world. You can watch the full conversation with Paul Graham and Jessica Livingston on YouTube here.

    Related Reading

  • Bill Ackman on Investment Strategy, What the Market Is Missing, and How AI Breaks Businesses

    Bill Ackman, founder and CEO of Pershing Square, joined the All-In Podcast for a conversation about how his investment approach has shifted toward permanent, long-term ownership, why he believes the highest-quality companies are being left behind by a market chasing the new new thing, and how AI is raising the risk of disruption for almost every business. He also lays out his plan to turn Howard Hughes into a Berkshire Hathaway-style compounding machine built on insurance. You can watch the full conversation here. Below is a structured breakdown of the ideas, the stories, and the frameworks he uses to underwrite a business.

    TLDW

    Ackman explains how his philosophy evolved from a smaller, more liquid activist toward concentrated, permanent ownership of durable, non-disruptible businesses, with much of his activism now playing out on X rather than in the boardroom. He tells the origin story of his first big trade, Wendy’s and the Tim Hortons spin-off, and explains why a large long-term shareholder on a board is an antidote to short-term markets. On AI, he argues that this is the greatest era in history to build a company, which means the risk of being disrupted has gone up enormously, and that the market is mispricing high-quality compounders like Microsoft, Meta, and Amazon while crowding into chips, semiconductors, and energy. He works through the SaaS question and why niche software is more at risk than platforms, how he underwrites SpaceX, xAI, OpenAI, Anthropic, and Palantir like late-stage venture bets using a people, opportunity, context, deal framework, and why founder-led companies have an edge in making radical calls. The back half covers his Howard Hughes plan to copy Buffett’s insurance-float model, the role of cost of capital and reflexivity in markets, the meme-stock era, going direct on social media, and the three different ways an investor can put money to work with Pershing Square.

    Thoughts

    The most useful idea in the interview is the way Ackman reframes disruption as the central investing problem of the AI era. His point is that the same forces making this the best time in history to start a company, meaning near-unlimited compute, capital, and talent, also raise the odds that any given incumbent gets disrupted. That reframes the word quality. It is no longer mostly about margins and moats. It becomes about non-disruptibility, which is a much higher bar than most quality investors were using a decade ago, and it is why he says most of his research time now goes into assessing that single risk.

    The what-the-market-is-missing thesis is classic contrarian Ackman. Arguing that Microsoft, Meta, and Amazon are the new old-fashioned, undervalued names while capital piles into semiconductors and energy is a direct echo of 2000, when Berkshire Hathaway bottomed precisely because money was chasing internet stocks. It is worth keeping in mind that he owns all three, so the call is also his book. The durable signal here is the framework, not the specific tickers: capital reliably chases the new new thing, and genuinely high-quality businesses get left behind during those rotations.

    The Howard Hughes plan is the most concrete bet in the conversation. Copying Buffett’s insurance-float playbook, short-term treasuries for policyholder money and equities for the surplus, onto a discounted real-estate holding company is elegant. The hard part is exactly what Ackman flags about insurance as an industry: the best investors go to hedge funds, not insurers, so most insurance companies only ever manage the liability side well. Pershing Square’s edge is that Ackman can both write the business and invest the float, which is the same reason it worked for Buffett. The framing of going from a four billion dollar company to a trillion over fifty years is a statement of intent, not a forecast, and should be read that way.

    Underneath all of it sits cost of capital and reflexivity. His observation that a higher stock price literally makes a company more valuable, because it lowers the cost of capital and creates acquisition currency, is the mechanism behind both Elon Musk’s empire and the meme-stock era he is wary of. Going direct on X is the same lever pointed at himself: communicate the vision, lower your own cost of capital, and make the bet easier for other people to place. It is a coherent worldview in which narrative and balance sheet continuously feed each other, and it explains a lot of his behavior over the last few years.

    Key Takeaways

    • The biggest change in Ackman’s approach over time is an appreciation for business quality, meaning long-term, durable, protected, non-disruptible growth as the most important factor.
    • He says he is as activist as ever, but more of it now happens on X than in the traditional corporate context.
    • His first big investment was Wendy’s, which owned Tim Hortons. The simple thesis was to buy Wendy’s, spin off Tim Hortons, and double the money.
    • Early on no one returned his calls, so he had Steve Schwarzman’s Blackstone write a fairness opinion, filed it publicly, and the company spun off Tim Hortons six weeks later. The CEO later thanked him after being fired with a large exit package.
    • Reputation compounds. Where Pershing Square once had to bang down the door, companies now sometimes tweet a welcome when it buys a stake.
    • A large long-term shareholder on a board is a counterweight to short-term markets, letting management test ideas privately and pursue initiatives that hurt the next few quarters of earnings.
    • Pershing Square owns Microsoft, Meta, and Amazon. Ackman argues you are either invested in AI directly or indirectly, or it is a threat, so you have to understand it.
    • The hardest and most important job for a concentrated investor is judging the risk of disruption, and that risk has risen dramatically.
    • This is the greatest era in history to build a business because of near-unlimited access to compute, capital, and talent, which is exactly why the probability of being disrupted has gone up enormously.
    • Markets bring their eye to the new new thing, currently chips, semiconductors, and energy, while high-quality companies get left behind.
    • He draws an analogy to 2000, when Berkshire Hathaway traded at one of its lowest valuations because everyone chased internet stocks. He sees a similar dynamic around Amazon, Meta, and Microsoft today.
    • On the SaaS question, he worries more about a Salesforce than a platform like Microsoft, because niche software charging high per-seat or per-year prices is most exposed, while low-priced platforms are safer.
    • Any software company today has to be as AI-enabled as possible, or risk losing the monopolistic pricing it once enjoyed.
    • His famous March 2020 CNBC appearance was an attempt to reach President Trump and argue for a short shutdown, paired with the view that stocks were incredibly cheap and worth buying.
    • He describes valuation as a tether on the market: when prices stretch too high they snap back, and when they get too cheap the same rubber band pulls valuations up. Calling that out publicly can trigger a psychological reset.
    • His recent bullish call came because stocks of really high-quality companies had gotten crazy cheap on fundamentals, meaning the present value of the cash they generate.
    • He underwrites high-multiple names like SpaceX as venture investments using a framework from business school: people, opportunity, context, deal.
    • On SpaceX, people and opportunity are one of one, the context is incredible, and Starlink plus near-monopoly low-cost launch make it strategically valuable. The complicated part is the deal, meaning the valuation. He invested via an SPV after Ron Baron’s nudge, and also invested in xAI.
    • He treats OpenAI, Anthropic, and Palantir as late-stage venture bets that have proven they can generate real revenue, and says OpenAI should do a better job communicating how it thinks about its enormous capital commitments.
    • Every CEO in America is asking how to use AI, how it applies to their business, and how it is a threat. It is top of mind and boards open every meeting with it.
    • He has not seen much enterprise AI success yet, citing a McKinsey study that 95 percent of enterprise initiatives fail and the rise of the forward deployed engineer as the hot role bridging promise and ROI. Pershing Square itself uses AI mainly for legal, compliance, and back-office work.
    • Founder-led companies have an advantage because founders have the authority and the economic stake to make radical calls, while the average S&P 500 CEO has a roughly three to four year tenure and is incentivized not to make mistakes.
    • He cites Mark Zuckerberg buying Instagram and WhatsApp as the kind of shocking-at-the-time calls that a founder with a track record can make.
    • Ben Graham’s enduring lesson is that a stock is an interest in a business, not a piece of paper, but Graham mostly invested in liquidations and cash-rich shells, and made most of his money on Geico.
    • Most of Buffett’s value at Berkshire came from owning insurance operations and focusing on the asset side of the balance sheet, not just the liability side.
    • Insurance is hard to copy because top investors do not go to work for insurers. Buffett owned half his company and was a great investor, which is why it worked.
    • Howard Hughes came out of the General Growth bankruptcy and owns master-planned cities like Summerlin, with 26,000 acres in the Las Vegas area, comparable to the Irvine Company that built roughly a hundred billion dollars of wealth for Donald Bren.
    • The plan is to reinvest the cash Howard Hughes generates into insurance, put policyholder float in short-term treasuries and the surplus in common stocks, and build a compounding machine over fifty years, buying it at roughly sixty cents on the dollar.
    • A company must earn a return above its cost of capital for the stock to rise. Elon Musk has kept his companies’ cost of capital extremely low, and a SpaceX IPO near a 1.75 trillion dollar valuation could be one of the lowest cost of equity capital transactions ever.
    • Markets have changed less because of Ackman and more because of figures like Ryan Cohen and GameStop, where a stock can trade well above its value on personality and an army of followers.
    • Higher valuations are reflexive: a rising stock price lowers cost of capital and creates currency to issue stock and acquire businesses, which is part of how Elon built Tesla.
    • There are three ways to invest with Pershing Square: the management company itself (a royalty on compounding assets with no capex), PSUS (a portfolio of best ideas trading at an 18 percent discount), and Howard Hughes (a bet on building the next Berkshire). A dollar invested 22 years ago became roughly 27 to 28 times net of fees.
    • Going direct on X, with 2.2 million followers, lets him communicate his vision and lower the friction for others to back his bets, even as his very long tweets have become a running meme.

    Detailed Summary

    From activist trades to permanent capital

    Ackman frames the evolution of his career as a steady move toward business quality. As a smaller, more liquid investor early on, he did not have to think as long-term. As Pershing Square became a bigger, more concentrated investor, durable growth became the dominant factor in every decision. He insists he is still as activist as ever, but a lot of that energy has shifted to X, where he can argue a position publicly rather than only inside a boardroom. The best investments, he notes, are the ones where you do not need to join the board and do anything at all.

    The Wendy’s and Tim Hortons origin story

    One of Pershing Square’s first investments was Wendy’s, which owned the Canadian coffee and donut chain Tim Hortons. The value of Tim Hortons alone was greater than the entire value of Wendy’s, so the idea was simple: buy Wendy’s, spin off Tim Hortons, and double the money. Ackman bought ten percent of the company and could not get the CEO to return a single call, so he had a contact at Blackstone, with Steve Schwarzman’s sign-off, write a fairness opinion on what Wendy’s would be worth after a spin-off, filed it publicly, and watched the spin-off happen six weeks later. The CEO eventually called back to thank him, having been fired but rewarded with a large exit package. Over the years that scrappy approach gave way to a reputation that now opens doors on its own.

    Why a long-term shareholder on the board matters

    The core problem of being a public company, in Ackman’s telling, is the short-term nature of markets and analysts, when a good business should be run in the context of years and even decades. A large, supportive shareholder on the board gives management a place to test ideas before exposing them to the public and a credible voice willing to back initiatives that hurt earnings for a few quarters. That is the value-add he believes a constructive activist can bring to a mature public company, as opposed to a startup where the best outcome is simply to own a great business and stay out of the way.

    AI and the rising risk of disruption

    For a concentrated, long-term investor, the most challenging task is judging the risk that two people from Stanford in a garage build something that destroys your thesis. Ackman argues that risk has climbed dramatically because this is the greatest era in history to build a company, with near-unlimited access to compute, capital, and talent. The paradox is that the conditions that make building easier also make incumbents more fragile, so the bulk of his research now centers on assessing how disruptible a business really is.

    What the market is missing

    Investors bring their attention to the new new thing, currently chips, semiconductors, and energy, which leaves high-quality companies behind. Ackman compares the moment to 2000, when Berkshire Hathaway traded at one of its lowest valuations ever because capital was chasing internet stocks. He sees an echo today in how Amazon, Meta, and Microsoft are treated as old-fashioned, and he considers them undervalued on fundamentals, where value is the present value of the cash a business generates over its life. His recent bullish call, like his March 2020 appearance, came because stocks of really high-quality companies had simply gotten too cheap.

    The SaaS question and AI-enabled software

    On the so-called SaaS apocalypse, Ackman says it is a company-by-company analysis. He worries more about something like Salesforce than about a low-priced platform. The companies most at risk are those that extracted near-monopolistic profits by charging a high annual price for a niche product, because AI lowers the barrier to replicating that functionality. A platform where the average customer pays a small amount per seat, like Microsoft, is far less exposed. The takeaway for any software company is to become as AI-enabled as it possibly can.

    Underwriting SpaceX, xAI, and the AI labs like venture

    For the highest-multiple private companies, Ackman uses a venture lens and a framework a business school professor taught him: people, opportunity, context, deal. SpaceX scores as one of one on people and opportunity, with an incredible context and a near-monopoly in low-cost launch through Starlink, which makes even Amazon a likely customer. The complicated variable is the deal, meaning the valuation, and he admits he has not done all the math, having invested through an SPV after Ron Baron encouraged him, along with a position in xAI. He treats OpenAI, Anthropic, and Palantir as late-stage venture bets that have proven real revenue, and argues OpenAI in particular should communicate more clearly how it justifies capital commitments that vastly exceed current revenue.

    Founder-led companies and the authority to act

    Ackman agrees that founder-led companies have a structural advantage in a fast-changing environment. The average S&P 500 CEO has a tenure of roughly three to four years, a small economic stake, and an incentive not to make a career-ending mistake. A founder is betting an entire life and reputation, has the authority of a major voting and economic position, and has usually made several hard, contrarian calls that turned out right. He points to Mark Zuckerberg’s acquisitions of Instagram and WhatsApp, which looked shocking at the time, as exactly the kind of decision a founder with a track record can make and a hired manager often cannot.

    Howard Hughes as Berkshire Hathaway 2.0

    Ackman points to a detailed financial history of Berkshire Hathaway showing that the vast majority of Buffett’s value creation came from owning insurance and focusing on the asset side of the balance sheet, not just the liability side. Insurance is hard to replicate because skilled investors join hedge funds rather than insurers, but Buffett owned half his company and was a great investor. Pershing Square is applying the same idea to Howard Hughes, a company created out of the General Growth bankruptcy that owns master-planned cities such as Summerlin, with 26,000 acres around Las Vegas, in the spirit of the Irvine Company that made Donald Bren roughly a hundred billion dollars. The plan is to reinvest the company’s cash into insurance, place policyholder float in short-term treasuries and the surplus in common stocks, avoid issuing stock the way Buffett did, and compound for fifty years, all bought at around sixty cents on the dollar.

    Cost of capital, reflexivity, and going direct

    A company only creates value when it earns above its cost of capital, which is why Howard Hughes, seen as a high-cost-of-capital real-estate business, has long traded at a discount, and why Ackman is repurposing its assets into a higher-returning model. He highlights how reflexive markets are: a higher stock price itself makes a company more valuable by lowering its cost of capital and creating currency to raise money and acquire businesses, a lever Elon Musk used to build Tesla. He attributes real market change less to himself and more to figures like Ryan Cohen and GameStop, where personality and a following can lift a stock far above its value. His own going-direct strategy on X, with 2.2 million followers and famously long posts, is the same mechanism applied to communicating a vision and lowering friction for investors. He closes by laying out three ways to invest with Pershing Square: the management company as a royalty on compounding assets, the PSUS portfolio trading at an 18 percent discount, and Howard Hughes as a bet on building the next Berkshire.

    Notable Quotes

    “The best investments are one where you don’t need to join the board and do anything.”

    Bill Ackman, on the kind of business he most wants to own

    “The probability of your being disrupted has gone up enormously.”

    Bill Ackman, on why assessing disruption risk now dominates his research

    “Valuation is like a tether on the market, right? When it gets too high, it’s like this rubber band that’s stretching and inevitably it bounces back.”

    Bill Ackman, on how prices revert at both extremes

    “People, opportunity, context, deal.”

    Bill Ackman, on the business school framework he uses to underwrite companies like SpaceX

    “Every CEO in America today is like, how do I use AI?”

    Bill Ackman, on AI as the top opportunity and threat in every boardroom

    “A closed mouth gathers no foot.”

    Bill Ackman, quoting the line a friend put next to his name in his high school yearbook

    “The increase in value of the company increases the value of the company, right? Because it lowers the cost of capital, it gives you more flexibility, gives you the ability to issue stock, raise capital, acquire other businesses.”

    Bill Ackman, on the reflexivity between stock price and corporate value

    “The company’s got like a $4 billion market cap and the goal is to build it into a trillion dollar thing over time compounding.”

    Bill Ackman, on his fifty-year plan for Howard Hughes

    Taken together, the conversation is a tour of how Ackman now thinks about quality, disruption, and compounding, and a preview of the Berkshire-style machine he wants to build out of Howard Hughes. Watch the full conversation here.

    Related Reading

  • Tobi Lütke on Uncapped Episode 50, Building Shopify in the AI Era, The Net Impact Memo, Six Week Cycles, and Why Software Was the Hidden Infrastructure of Our Time

    Tobi Lütke, the founder and CEO of Shopify, sits down with Jack Altman for Episode 50 of the Uncapped podcast for one of the most useful hours of operating wisdom you will hear from a sitting public company founder. The conversation moves from why Tobi still loves the work after twenty years, through the practical mechanics of running Shopify on six week review cycles, into the now famous AI memo he sent to the entire company, the rise of Claude Code style agents, what it means to spend tens of percent of revenue on AI tokens, why the modern web browser is a wonder of the world, and where small businesses actually fit in a world where the next Turing test might be “build me a million dollar business.” This is essential listening for any founder, operator, or investor trying to make sense of what 2026 actually requires.

    TLDW

    Tobi Lütke explains how he keeps loving his life’s work by pursuing what Paul Kapoa called “beautiful problems,” why “different” must always be the starting position because anything copied can only be marginally better, and why Silicon Valley’s last decade of orthodoxy has been bad for originality. He walks through his decision to send Shopify’s company wide AI memo and codify it into net impact performance reviews, the unlimited token policy for employees, why small three to five person teams are his bet, and how Parkinson’s Law and a six week review cycle force pace. He calls the doomer permanent underclass narrative completely absent from Shopify’s data, citing one new merchant getting their first sale every 36 seconds, and proposes “build me a million dollar business” as the real successor to the Turing test. He argues humanity has not stopped building wonders, we just built them all in software for thirty years, that the web browser is one of the most impressive engineering achievements ever made and could never get approved by a modern app store, and that the freed talent leaving software will rebuild the physical world. He shares his hiring philosophy, why he restarted the Shopify intern program at scale with Waterloo, his preference for public over private status, and ends with a short reading list anchored by Parkinson’s Law, Lessons of History, and a book called What Is Intelligence.

    Key Takeaways

    • Tobi’s recipe for life’s work is to find a beautiful problem worth occupying you for life, and accept that the solved problem will spawn delightful problem children to keep you engaged.
    • His simple model of success, “figure out what it costs and be willing to pay it,” with the price almost always being time, commitment, and discomfort rather than money.
    • He warns CEOs against collecting “barnacles” of aesthetic expectation, the statesman travel and baby kissing pattern, calling that lifestyle inefficient and personally miserable.
    • He invokes Kathy Sierra’s line “don’t make better cameras, make better photographers” as his core product philosophy, beautiful tools that induce more ambition and skill in the user.
    • Mediocre products feel like room temperature. Great products are forged in a furnace and require sustained heat from the team.
    • Shopify builds its own HR software internally because the available options are not what they want to use. Toolmaking is a stated cultural identity.
    • Originality is axiomatic. If you build the same thing as everyone else, you can only be marginally better. The starting position has to be “different,” and if you converge on the consensus answer through that path you have actually learned something.
    • Shopify has tried to eliminate the word “failure” internally, replacing it with “the successful discovery of something that didn’t work.”
    • Tobi says Silicon Valley spent the last decade declaring war on distinction, that the diversity push as practiced eradicated eccentricity, and that the inversion is now beginning. Companies should resemble islands of misfit toys, not convergence on a pre-ordained truth.
    • One of his most surprising career insights, when he visited the Valley as a Canadian outsider and asked founders how they ran their companies, he only ever received the highlight reel. Trying to clone what those founders described led him to invent practices the originals had never actually implemented.
    • The Shopify AI memo, sent company wide, made it explicit that two equally good engineers fifteen minutes earlier are no longer equivalent if one is fluent with AI tools and the other is not. This was codified into the company’s “net impact” performance review framework.
    • Tobi describes the “founder credibility bank” as the most underrated asset in a founder led company. Every onboarding deposits a little credibility, and the founder can spend it on hard change management that would otherwise take years of incremental culture work.
    • Shopify gives every employee an unlimited token policy for AI tools and displays token usage and departmental percentile on internal profiles. Token spend is tracked because it has to be allocated to opex, not because it is the target.
    • He confirms Shopify’s AI token spend is “extremely high” relative to revenue and notes that some private companies are now running token spend at many tens of percent of revenue, a level he thinks cannot persist at every stage but makes sense right now because the tokens are buying so much leverage.
    • Shopify is on track to 10x its annual token consumption and 3x its GPU footprint, and those two curves do not converge anywhere good for price relief.
    • His bet on team design is small, three to five people, which has always been Shopify’s bias. AI agents now handle the customer research summarization role that previously required a dedicated team member, raising every individual to a “seven out of ten on every scale.”
    • Parkinson’s Law (the book, 60 pages, 1960s edition) is his single most recommended management book. He owns multiple original print runs and gives copies to executives. “Work expands to the time allocated.”
    • Shopify runs on a six week review cycle. The first warning sign that a team has slipped into quarterly pacing is seeing “H1” or “H2” used in a PowerPoint. He now thinks six weeks is too slow and is actively trying to figure out what replaces it.
    • The “permanent underclass” doom narrative simply does not appear anywhere in Shopify’s data. New entrepreneurs are reporting that AI has finally fixed computers for them, expanding their businesses and letting them hire.
    • A new merchant gets their first Shopify sale every 36 seconds. Every reduction in onboarding friction produces a measurable jump in completed businesses.
    • Tobi proposes “go make me a million dollars” as the natural successor to the Turing test, an end to end test of acting in the real world, marketing, prioritizing, shipping, and producing something people will pay for.
    • Shopify Collective lets aspiring entrepreneurs sell other manufacturers’ products if their skill is marketing rather than making. Print on demand, additive manufacturing, contract manufacturing, CNC, 3D printing, and humanoid robotics are all pulling the cost of “make the product yourself” toward the floor.
    • The reason American infrastructure feels stagnant for thirty years is that the infrastructure humanity actually needed was digital. The web browser, Linux, Google, social networks, and Shopify itself are wonders that dwarf a refinery in complexity but are invisible by nature.
    • Tobi calls the modern web browser one of the wonders of the world. Font rendering alone is a Turing complete system. No app store on earth would approve the browser today if it did not already exist, because the pitch (“we download untrusted code from strangers and run it on your machine to reconfigure your computer for them”) sounds insane.
    • The next chapter is the brightest software engineers being freed by AI to build the physical infrastructure that has been deferred for a generation.
    • He prefers to predict the future by collecting many data points and matching them to super linear, linear, or sublinear curves. The current AI horizon is the hardest period of his career to forecast because the time horizons are so short.
    • Programming is overhyped as the locus of AI value. The bigger story is using the programming harness, the file system, tools, and memory files of products like Claude Code, to drag every other domain into the programming domain where the models are strongest.
    • The underhyped frontier is enterprise deployment. Most companies are still asking “help me do the thing I already did, slightly better,” instead of “if AI had existed since Alan Turing, how would I have designed this job from scratch.”
    • Tobi restarted the Shopify intern program at scale, partnered closely with the University of Waterloo, and explicitly frames interns as both students and teachers because they are AI native in a way the rest of the company is still catching up to.
    • He briefly believed AI would tilt the value of work toward early career talent with maximum fluid intelligence, then revised when he watched how much creative “steering” the best programmers were quietly contributing inside the AI loop. Good people are still good.
    • His recruiting philosophy is “build a company worth looking for” rather than selling candidates. Better to actually be healthier than to look healthier in photographs.
    • Tobi is a vocal defender of being a public company. Shopify IPO’d at a $1.5 billion valuation and has roughly 100x’d in public markets, which means an enormous number of retail investors have shared in the upside that recent unicorns reserve for insiders.
    • His framing of money, “money is how you vote for what you want.” Buying a product or buying a share is a vote for the thing existing.
    • His current reading recommendations, Parkinson’s Law, Lessons of History, and a book called What Is Intelligence that reframes biology around prediction.
    • He reads at night because his wife sleeps early and he does not need much sleep. He loves the Kindle precisely because it cannot do anything else, a “wonderful single purpose device.”

    Detailed Summary

    Why Tobi Still Loves the Work After Twenty Years

    The interview opens with Jack Altman asking how Tobi avoids the founder fade that hits most public company CEOs after a decade. Tobi answers from a place that is half psychology and half pedagogy. He has a hard time learning anything he has not first experienced as a problem worth solving, which is why he could not internalize school mathematics until he discovered that Wolfenstein 3D was essentially live trigonometry. That pattern, find a beautiful problem and let it drag you into the discipline, has carried him through twenty years of Shopify. He quotes Paul Kapoa on the idea that the luckiest people find a problem that occupies them for a lifetime and, if they are unfortunate enough to solve it, get rewarded with “delightful problem children” that keep the work alive.

    Barnacles, Statesmen, and the Aesthetic Trap of Being a CEO

    He admits he is not naturally calm, and that he initially fell into the trap of trying to perform the CEO aesthetic, the statesman, the global travel, the baby kissing. He found it inefficient and personally miserable. The shift came from reading Kathy Sierra and adopting her line about not making better cameras but making better photographers. Shopify exists, in his framing, to be a beautiful tool that induces ambition in the merchant. Mediocre products feel like room temperature, and great products are forged in a furnace. The job of leadership is to keep supplying the heat.

    Different First, Convergence Second, Failure as Successful Discovery

    Asked whether he prefers originality or quality, Tobi is unequivocal. The starting position must be different. If you copy the consensus answer, you are bounded to a few percentage points of variance from it. If you start different and converge on the consensus, you have learned something. If you start different and the experiment gets worse, you have learned something even more valuable, which is that one of your assumptions about the world was wrong. He calls null results in science “massively underrated” and notes that Shopify has tried to remove the word “failure” from the internal vocabulary, substituting “the successful discovery of something that didn’t work.”

    Why Silicon Valley Lost Its Originality

    Jack pushes on the herd mentality he has felt in the Bay Area, and Tobi is direct. He thinks Silicon Valley “declared war on distinction” for a decade, with the diversity conversation as practiced effectively eradicating eccentricity. He prefers the metaphor of “an island of misfit toys,” and says the inversion is now beginning. He also relays one of the most useful career lessons he has shared, that during his visits to the Valley as an outsider asking founders how they ran their companies, he only ever received the highlight reel. He went home and engineered a “Shopify version” of what he thought he had heard, and only years later realized that he had often built more rigorous versions of things the originals had never actually implemented.

    The AI Memo, Net Impact Reviews, and the Founder Credibility Bank

    Tobi was one of the first Fortune class CEOs to send a company wide memo saying that AI fluency was now a baseline expectation. He walks through the decision. Two engineers who were equally productive fifteen minutes ago are no longer equivalent the moment one of them adopts the new tools. The kind thing to do is to make that explicit. Shopify codified it into “net impact” performance reviews, where the question is not how much code you wrote but how much net impact you produced for the company and the mission. He gives every employee an unlimited token policy and tracks usage at the profile level, including percentile within department. The spend is tracked because it has to be allocated to opex, not because the number itself is the target.

    He introduces the concept of the “founder credibility bank,” which may be the single most quotable idea in the interview. Every time a new employee onboards and hears how the company was created, a small deposit of credibility is made into a virtual account that only the founder can draw on. Founders can spend that balance on hard change management, the kind of pace step change that would otherwise require years of small cultural nudging. The AI memo was a deliberate withdrawal from that account, and the speed of adoption that followed has been, in his telling, remarkable.

    Tokens, Opex, and the Limits of Spend as Revenue

    Jack presses on the financial reality of AI tokens. Tobi confirms that Shopify’s token spend is “extremely high” relative to revenue, and that the leverage they are buying makes the spend a no brainer at the current stage of the curve. He concedes that private companies running token spend at “many tens of percent of revenue” cannot sustain that ratio forever, but he is not worried for Shopify because the tokens are clearly productive and Shopify is a profitable public company with the balance sheet to lean in. He expects to 10x token consumption and 3x GPUs every year for now, and notes that the curves do not converge in a direction that lowers prices. He has high faith in markets to find clearing prices.

    Small Teams, Parkinson’s Law, and the Six Week Cycle

    On team architecture, Tobi has always preferred three to five person teams and says AI has finally made that feasible across the board. Roles that previously required a dedicated specialist, customer research summarization being the canonical example, are now handled by the “agentic harness” routing summarized customer feedback into every team. Everyone is a “seven out of ten on every scale” by default. He spends serious time on pace, which he treats as the single most important variable to control. His most recommended book is Parkinson’s Law, a 60 page volume from the 1960s that he gives to every executive. “Work expands to the time allocated.” He runs the company on a six week review cycle and treats the appearance of “H1” or “H2” in a PowerPoint as a hard warning sign that a team has drifted into quarterly thinking. He now believes six weeks is too long and is actively redesigning the cycle.

    There Is No Permanent Underclass in the Shopify Data

    Jack raises the cultural fear that AI is creating a permanent young underclass with no career ladder. Tobi simply does not see it in Shopify’s data. The merchants are reporting the opposite, that AI has finally fixed computers for non technical small business owners and is unlocking hiring. He cites the statistic that a new merchant gets their first sale on Shopify every 36 seconds, and that every reduction in onboarding friction produces a measurable jump in completed businesses. Every form of friction is a hurdle that someone considers giving up at. AI has removed more of those hurdles in two years than any platform shift before it.

    A New Turing Test, “Build Me a Million Dollar Business”

    Tobi nominates a successor to the Turing test, which he points out the field already sailed past with surprisingly little fanfare. The real test is “go make me a million dollars.” It requires acting in the real world, marketing, prioritization, shipping, sourcing, building inventory, and convincing strangers to vote for the product with a real million dollars of their own. He believes we are getting there. Shopify already supports the path through Shopify Collective, the discovery layer for manufacturers willing to white label their products, and print on demand, contract manufacturing, additive manufacturing, CNC, 3D printing, and humanoid robotics are all collapsing the cost of physically producing a product. Shopify’s stated ambition is to be the vessel for AI to run all of the non product parts of the business so that the only thing the human needs to show up with is the product itself.

    Software Was the Hidden Infrastructure of the Last Thirty Years

    The most original argument in the episode is about why American infrastructure has appeared to stagnate for a generation. Tobi rejects the standard story. Humanity has not stopped building wonders, it has built every one of them in software. The web browser, Linux, Google, the social networks, and Shopify itself are projects whose complexity dwarfs a refinery or a dam, and they were built by global volunteer networks and by companies the public underestimates because the work is invisible. The browser in particular he calls a wonder of the world. He notes that font rendering alone is a Turing complete system, that no modern app store would approve the browser if it did not already exist, and that the basic pitch of “we will download untrusted code from strangers and reconfigure your computer for them” should sound insane but does not because we are used to it. The implication for the next twenty years is that all of the talent that flowed into software is now being freed by AI to rebuild the physical infrastructure that has been quietly deferred.

    Predicting AI Two Years Out, Overhype and Underhype

    Jack asks whether a CEO should try to forecast AI two years ahead or operate six months at a time. Tobi is firmly in the forecasting camp and admits his friends would laugh because predicting the future from many data points and curve types is his predominant obsession. He says the AI memo was slightly too early, and that is exactly the point, because a memo that arrives late costs the company its head start. He flags two specific market level mis estimations. The first is that the labs over invest in programming because programming is their internal problem, and people then over generalize a model’s coding ability to other domains where it is not yet as strong. The second is that almost everyone is under deploying AI in their actual companies, still asking “help me do my old job better” instead of “if AI had existed since Alan Turing, how would I have designed this job from scratch.” That second framing is, in his view, where the next decade of value lives.

    Hiring, Interns as Teachers, and Why Good People Are Still Good

    Tobi briefly believed AI would tilt the value of labor toward early career fluid intelligence, since interns adopted the new tools faster than veterans. He revised that view once the coding harnesses matured. The best programmers, it turned out, were quietly contributing enormous amounts of creative steering inside the AI loop, work that does not show up in the diff but that no junior with no domain pattern matching can replicate. Good people are still good. Shopify has massively scaled its intern program with the University of Waterloo, and explicitly treats interns as both students and teachers because they bring AI nativeness the rest of the company still has to catch up to. On recruiting, Tobi’s philosophy is to build a company worth looking for. The metaphor he uses is health, that companies waste energy trying to look healthy in photos when they should be doing the work to actually be healthier.

    Public Company Defense and the Reading List

    Tobi pushes back on the modern preference for staying private. Shopify went public at $1.5 billion and is now over $100 billion, which means an enormous number of retail investors got to participate in the upside. He treats money as a voting mechanism. Buying a product is a vote for the product. Buying a share is a vote for the company. He is comfortable with the diligence and quarterly scrutiny of public markets because both make him a better operator. He closes with a short reading list, Parkinson’s Law (60 pages, 1960s edition, owned in original print runs and gifted to executives), Lessons of History, and a book called What Is Intelligence that reexplains biology from a prediction first perspective. He reads at night while his wife sleeps, on a Kindle, which he loves precisely because it cannot do anything else.

    Thoughts

    The single most useful idea Tobi puts on the table is the “founder credibility bank.” It explains, in one clean image, why founder led companies move so much faster than the same company would after a transition. The credibility is not personal magnetism, it is the structural slot the founder occupies in the org chart, and every onboarded employee makes a small deposit into it as they hear the founding story. Most founders never realize the account exists, or spend it on cosmetic decisions, and then are surprised when the well runs dry. Tobi’s discipline is the opposite. He saves the balance for moments of forced change and spends it confidently when the moment arrives, the AI memo being the obvious recent case. Any CEO reading this transcript should be making a list of the changes they have been postponing and asking whether they are operating with a fuller credibility account than they have been willing to admit.

    The token spend conversation is the most interesting strategic disclosure. A profitable public company at scale openly says it likes the tokens it is buying, is on track to 10x annual token consumption and 3x GPU footprint, and is comfortable with private peers spending tens of percent of revenue on inference. That is not the language of a market that is about to compress. It is the language of a leverage trade that is still in its early innings, and it is one of the cleanest statements you will get from a public CEO about why the AI capex story is not a bubble for the buyer. Whether it is a bubble for the seller is a separate question, but on the demand side, this interview is a load bearing data point.

    The argument that “software was the hidden infrastructure of the last thirty years” is the kind of reframe that should make policy people uncomfortable. The standard narrative that America stopped building anything ambitious since the Hoover Dam is true only if you refuse to count Chrome, Linux, AWS, Shopify, and every social graph that connects three billion people in real time. Tobi’s claim that the browser would not be approved by a modern app store is a particularly sharp gut check. The implication is not nostalgic. It is forward looking. The same talent that built the digital wonders is being freed by AI to redirect toward houses, transport, energy, and care, and the next decade will be measured by how much of that redirection actually lands.

    The “build me a million dollar business” framing as a Turing test successor is the kind of measurable goal that AI labs and policy makers should be writing down. It is end to end. It includes physical world action, marketing, sourcing, prioritization, and customer validation that no in domain benchmark can fake. Shopify is the obvious substrate for the first crossing of that threshold, and the existence of Shopify Collective, print on demand pipelines, and contract manufacturing networks means a credible attempt is already much closer than the public conversation acknowledges. The first end to end autonomous Shopify business that clears a million dollars will be a more legible AGI moment than any benchmark a lab can publish.

    The smaller thread on Silicon Valley orthodoxy is worth pulling on. Tobi’s claim that the diversity conversation as practiced eradicated distinction is unfashionable but observable inside many tech companies, where the people most likely to do unusual work are the most likely to leave. His preferred metaphor of “an island of misfit toys” is closer to what made the Valley work in earlier decades than the current consensus aesthetic. The fact that a Canadian outsider, geographically removed from the dominant social pressure, runs the most valuable Canadian technology company in history is probably not a coincidence.

    Watch the full conversation here on YouTube.

  • 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.